
# ol991229q.cif

data_global

_publ_contact_letter
;
Dear Sir,

The following CIF file which contains three structures is associated with
the manuscript named "Control of Crystal Architecture: New Hydrogen Bonded
Donor-Acceptor Pairs between Dipyridylacetylenes and
2,5-Dichloro-3,6-dihydroxy-1,4-benzoquinone" by Md. Badruz Zaman, Masaaki
Tomura, and Yoshiro Yamashita  (Institute for Molecular Science, Okazaki,
Japan), which was submitted to Organic Letters (ol991229q) on November
1999.

Yours Sincerely,
;

_publ_contact_author               
;
     Dr. Md. Badruz Zaman
     Research Center for Molecular Materials
     Institute for Molecular Science
     Myodaiji, Okazaki, Aichi 444-8585, Japan
;
_publ_contact_author_phone         '+81-564-55-7486'
_publ_contact_author_fax           '+81-564-53-5728'
_publ_contact_author_email          zaman@ims.ac.jp

_publ_requested_journal            'Organic Letters'

loop_
_publ_author_name
 'Zaman, Md. Badruz'               #<--'Last name, first name'
 'Tomura, Masaaki'
 'Yamashita, Yoshiro'
_journal_name_full                 'Organic Letters'
_journal_volume                    '?'
_journal_page_first                '?'
_journal_page_last                 '?'
_journal_year                      '?'
_ccdc_journal_depnumber            '?'


#------------------------------------------------------------------------------

data_1

_chemical_name_systematic
;
complex of 2,2'-dipyridylacetylene and
2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone
;
_chemical_name_common              '[2][1]'
_chemical_formula_moiety           'C12 H8 N2, C6 H2 Cl2 O4'
_chemical_formula_sum              'C18 H10 Cl2 N2 O4'
_chemical_formula_weight            389.18
_chemical_melting_point             ?

_ccdc_compound_id                  '?'
_ccdc_biological_activity          '?'
_ccdc_polymorph                    '?'
_ccdc_chemdiag_type                '?'

_exptl_crystal_density_diffrn       1.600
_exptl_crystal_colour              'brown'

_diffrn_radiation_type             'Cu K\a'            
_diffrn_measurement_device         'EnrafNonius CAD4 diffractometer'
_ccdc_temp_data_collection          296
_ccdc_ls_R_squared                  0.0673
_refine_ls_abs_structure_details   '?'
_ccdc_disorder                     'none'
_ccdc_comments                     '?'

_cell_length_a                         3.8406(4)
_cell_length_b                         10.9748(14)
_cell_length_c                         11.1523(11)
_cell_angle_alpha                      59.665(9)
_cell_angle_beta                       84.586(9)
_cell_angle_gamma                      86.875(10)
_cell_volume                           403.89(8)
_cell_formula_units_Z                  1
_symmetry_cell_setting                 triclinic
_symmetry_space_group_name_H-M        'P -1'
_symmetry_Int_Tables_number            2
_refine_ls_R_factor_obs                0.0673
_refine_ls_wR_factor_obs               0.1397
_refine_ls_goodness_of_fit_obs         1.104

#------------------------------------------------------------------------------

loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Cl1 Cl 0.3000(6) 0.0283(2) 0.2177(2) 0.0454(6) Uani 1 d . . 
O1 O 0.1844(17) -0.2199(5) 0.5045(5) 0.049(2) Uani 1 d . . 
O2 O 0.6171(16) 0.2420(5) 0.2614(5) 0.047(2) Uani 1 d . . 
N1 N -0.0954(17) -0.5236(6) 0.2805(6) 0.034(2) Uani 1 d . . 
C1 C -0.2033(21) -0.4264(7) 0.3192(7) 0.034(2) Uani 1 d . . 
C2 C -0.1136(25) -0.2873(9) 0.2349(8) 0.046(2) Uani 1 d . . 
C3 C 0.0680(23) -0.2433(8) 0.1082(8) 0.046(2) Uani 1 d . . 
C4 C 0.1638(24) -0.3430(8) 0.0687(8) 0.046(2) Uani 1 d . . 
C5 C 0.0815(22) -0.4811(8) 0.1595(8) 0.041(2) Uani 1 d . . 
C6 C -0.4084(21) -0.4774(8) 0.4472(7) 0.034(2) Uani 1 d . . 
C7 C 0.3346(22) -0.1133(7) 0.4962(7) 0.035(2) Uani 1 d . . 
C8 C 0.4031(20) 0.0108(7) 0.3722(7) 0.028(2) Uani 1 d . . 
C9 C 0.5602(22) 0.1297(7) 0.3681(7) 0.033(2) Uani 1 d . . 
H1 H 0.1502(288) -0.3245(110) 0.6164(111) 0.116(39) Uiso 1 d . . 
H2 H -0.1731(231) -0.2167(86) 0.2549(84) 0.062(28) Uiso 1 d . . 
H3 H 0.1252(200) -0.1340(76) 0.0314(76) 0.054(24) Uiso 1 d . . 
H4 H 0.3004(164) -0.3094(59) -0.0251(62) 0.019(16) Uiso 1 d . . 
H5 H 0.1392(219) -0.5602(84) 0.1289(85) 0.071(28) Uiso 1 d . . 


loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Cl1 C8  1.717(7)  . ?
O1  C7  1.290(8)  . ?
O1  H1  1.20(11)  . ?
O2  C9  1.217(8)  . ?
N1  C5  1.313(9)  . ?
N1  C1  1.370(8)  . ?
C1  C2  1.371(10) . ?
C1  C6  1.415(9)  . ?
C2  C3  1.369(11) . ?
C2  H2  0.92(8)   . ?
C3  C4  1.393(11) . ?
C3  H3  1.08(7)   . ?
C4  C5  1.365(10) . ?
C4  H4  1.02(6)   . ?
C5  H5  1.09(8)   . ?
C6  C6  1.191(14) 2_446 ?
C7  C8  1.380(8)  . ?
C7  C9  1.523(10) 2_656 ?
C8  C9  1.445(9)  . ?
C9  C7  1.523(10) 2_656 ?

loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C7 O1 H1 117.7(48) . . ?
C5 N1 C1 119.3(7) . . ?
N1 C1 C2 120.1(7) . . ?
N1 C1 C6 116.7(6) . . ?
C2 C1 C6 123.2(7) . . ?
C3 C2 C1 120.3(8) . . ?
C3 C2 H2 114.8(53) . . ?
C1 C2 H2 124.8(54) . . ?
C2 C3 C4 118.6(8) . . ?
C2 C3 H3 124.7(39) . . ?
C4 C3 H3 116.5(39) . . ?
C5 C4 C3 118.6(8) . . ?
C5 C4 H4 123.4(34) . . ?
C3 C4 H4 118.0(33) . . ?
N1 C5 C4 123.0(8) . . ?
N1 C5 H5 116.6(44) . . ?
C4 C5 H5 120.1(44) . . ?
C6 C6 C1 177.1(11) 2_446 . ?
O1 C7 C8 123.2(7) . . ?
O1 C7 C9 116.8(6) . 2_656 ?
C8 C7 C9 120.0(7) . 2_656 ?
C7 C8 C9 121.4(6) . . ?
C7 C8 Cl1 120.5(6) . . ?
C9 C8 Cl1 118.1(5) . . ?
O2 C9 C8 123.4(7) . . ?
O2 C9 C7 118.1(7) . 2_656 ?
C8 C9 C7 118.5(6) . 2_656 ?

loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
 C5 N1 C1 C2 -2.8(11) . . . . ?
 C5 N1 C1 C6 176.8(8) . . . . ?
 N1 C1 C2 C3 3.5(13) . . . . ?
 C6 C1 C2 C3 -176.1(9) . . . . ?
 C1 C2 C3 C4 -1.1(14) . . . . ?
 C2 C3 C4 C5 -1.9(14) . . . . ?
 C1 N1 C5 C4 -0.2(13) . . . . ?
 C3 C4 C5 N1 2.6(14) . . . . ?
 N1 C1 C6 C6 -57.4(219) . . . 2_446 ?
 C2 C1 C6 C6 122.2(214) . . . 2_446 ?
 O1 C7 C8 C9 177.7(7) . . . . ?
 C9 C7 C8 C9 -2.8(12) 2_656 . . . ?
 O1 C7 C8 Cl1 -1.9(11) . . . . ?
 C9 C7 C8 Cl1 177.6(6) 2_656 . . . ?
 C7 C8 C9 O2 -178.2(8) . . . . ?
 Cl1 C8 C9 O2 1.4(10) . . . . ?
 C7 C8 C9 C7 2.7(12) . . . 2_656 ?
 Cl1 C8 C9 C7 -177.7(6) . . . 2_656 ?
 
#===END

data_2

_chemical_name_systematic
;
complex of 3,3'-dipyridylacetylene and
2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone
;
_chemical_name_common              '[3]2+[1]2-[H2O]3.38'
_chemical_formula_moiety           'C12 H10 N2 2+, C6 Cl2 O4 2-, 3.38(H2 O)'
_chemical_formula_sum              'C18 H16.76 Cl2 N2 O7.38'
_chemical_formula_weight            450.09
_chemical_melting_point             ?

_ccdc_compound_id                  '?'
_ccdc_biological_activity          '?'
_ccdc_polymorph                    '?'
_ccdc_chemdiag_type                '?'

_exptl_crystal_density_diffrn       1.567
_exptl_crystal_colour              'brown'

_diffrn_radiation_type             'Mo K\a'            
_diffrn_measurement_device         'Rigaku AFC7R diffractometer'
_ccdc_temp_data_collection          296
_ccdc_ls_R_squared                  0.0475
_refine_ls_abs_structure_details   '?'
_ccdc_disorder                     'none'
_ccdc_comments                     '?'

_cell_length_a                         9.913(2)
_cell_length_b                         12.752(2)
_cell_length_c                         3.8630(9)
_cell_angle_alpha                      92.79(2)
_cell_angle_beta                       98.669(19)
_cell_angle_gamma                      84.595(19)
_cell_volume                           480.32(18)
_cell_formula_units_Z                  1
_symmetry_cell_setting                 triclinic
_symmetry_space_group_name_H-M        'P -1'
_symmetry_Int_Tables_number            2
_refine_ls_R_factor_obs                0.0475
_refine_ls_wR_factor_obs               0.1180
_refine_ls_goodness_of_fit_obs         0.942

#------------------------------------------------------------------------------

loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cl1 Cl 0.59376(11) 0.21924(8) 0.3247(3) 0.0436(3) Uani 1 1 d . . . 
O1 O 0.7422(3) 0.0045(2) 0.4158(8) 0.0465(8) Uani 1 1 d . . . 
O2 O 0.6602(3) -0.1799(2) 0.1626(8) 0.0411(7) Uani 1 1 d . . . 
N1 N -0.1190(4) 0.8068(3) -0.3537(10) 0.0407(9) Uani 1 1 d . . . 
C1 C -0.0021(4) 0.6558(3) -0.0900(10) 0.0336(9) Uani 1 1 d . . . 
C2 C -0.1136(4) 0.7048(3) -0.2979(11) 0.0378(10) Uani 1 1 d . . . 
C3 C -0.0193(5) 0.8654(3) -0.2111(12) 0.0415(10) Uani 1 1 d . . . 
C4 C 0.0930(5) 0.8214(3) -0.0011(12) 0.0411(10) Uani 1 1 d . . . 
C5 C 0.1038(4) 0.7151(3) 0.0592(11) 0.0366(9) Uani 1 1 d . . . 
C6 C 0.0003(5) 0.5451(3) -0.0291(12) 0.0440(10) Uani 1 1 d . . . 
C7 C 0.5421(4) 0.0989(3) 0.1480(10) 0.0331(9) Uani 1 1 d . . . 
C8 C 0.6289(4) 0.0075(3) 0.2288(10) 0.0326(9) Uani 1 1 d . . . 
C9 C 0.5811(4) -0.0983(3) 0.0736(10) 0.0324(9) Uani 1 1 d . . . 
O3 O 0.6272(5) -0.3993(4) 0.1865(19) 0.147(4) Uani 1.000(14) 1 d . . . 
O4 O 0.3556(6) 0.5346(5) 0.321(2) 0.108(4) Uani 0.690(13) 1 d P . . 
H1 H -0.187(6) 0.833(5) -0.509(17) 0.10(2) Uiso 1 1 d . . . 
H2 H -0.187(4) 0.670(3) -0.424(11) 0.041(12) Uiso 1 1 d . . . 
H3 H -0.029(5) 0.936(4) -0.275(13) 0.072(17) Uiso 1 1 d . . . 
H4 H 0.153(4) 0.859(3) 0.080(10) 0.027(10) Uiso 1 1 d . . . 
H5 H 0.176(5) 0.686(4) 0.230(14) 0.066(15) Uiso 1 1 d . . . 


loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Cl1 C7 1.739(4) . ? 
O1 C8 1.239(4) . ? 
O2 C9 1.270(4) . ? 
N1 C2 1.323(5) . ? 
N1 C3 1.332(6) . ? 
N1 H1 0.88(6) . ? 
C1 C2 1.382(5) . ? 
C1 C5 1.389(5) . ? 
C1 C6 1.440(5) . ? 
C2 H2 0.95(4) . ? 
C3 C4 1.366(6) . ? 
C3 H3 0.94(5) . ? 
C4 C5 1.379(6) . ? 
C4 H4 0.81(4) . ? 
C5 H5 0.95(5) . ? 
C6 C6 1.183(8) 2_565 ? 
C7 C9 1.382(5) 2_655 ? 
C7 C8 1.401(5) . ? 
C8 C9 1.536(5) . ? 
C9 C7 1.382(5) 2_655 ? 

loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 N1 C3 121.7(4) . . ? 
C2 N1 H1 117(4) . . ? 
C3 N1 H1 121(4) . . ? 
C2 C1 C5 119.0(4) . . ? 
C2 C1 C6 119.2(4) . . ? 
C5 C1 C6 121.8(4) . . ? 
N1 C2 C1 120.3(4) . . ? 
N1 C2 H2 115(3) . . ? 
C1 C2 H2 125(3) . . ? 
N1 C3 C4 120.6(4) . . ? 
N1 C3 H3 116(3) . . ? 
C4 C3 H3 123(3) . . ? 
C3 C4 C5 119.6(4) . . ? 
C3 C4 H4 119(3) . . ? 
C5 C4 H4 121(3) . . ? 
C4 C5 C1 118.8(4) . . ? 
C4 C5 H5 119(3) . . ? 
C1 C5 H5 121(3) . . ? 
C6 C6 C1 177.9(7) 2_565 . ? 
C9 C7 C8 123.0(3) 2_655 . ? 
C9 C7 Cl1 118.4(3) 2_655 . ? 
C8 C7 Cl1 118.6(3) . . ? 
O1 C8 C7 125.3(4) . . ? 
O1 C8 C9 116.7(4) . . ? 
C7 C8 C9 118.0(3) . . ? 
O2 C9 C7 124.9(4) . 2_655 ? 
O2 C9 C8 116.2(3) . . ? 
C7 C9 C8 119.0(3) 2_655 . ? 

loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C3 N1 C2 C1 -0.6(7) . . . . ? 
C5 C1 C2 N1 0.1(6) . . . . ? 
C6 C1 C2 N1 179.0(4) . . . . ? 
C2 N1 C3 C4 0.1(7) . . . . ? 
N1 C3 C4 C5 1.0(7) . . . . ? 
C3 C4 C5 C1 -1.5(7) . . . . ? 
C2 C1 C5 C4 1.0(6) . . . . ? 
C6 C1 C5 C4 -178.0(4) . . . . ? 
C2 C1 C6 C6 -83(18) . . . 2_565 ? 
C5 C1 C6 C6 96(17) . . . 2_565 ? 
C9 C7 C8 O1 177.4(4) 2_655 . . . ? 
Cl1 C7 C8 O1 -0.8(6) . . . . ? 
C9 C7 C8 C9 -2.4(7) 2_655 . . . ? 
Cl1 C7 C8 C9 179.4(3) . . . . ? 
O1 C8 C9 O2 2.6(6) . . . . ? 
C7 C8 C9 O2 -177.6(4) . . . . ? 
O1 C8 C9 C7 -177.5(4) . . . 2_655 ? 
C7 C8 C9 C7 2.3(6) . . . 2_655 ? 

#===END

data_3

_chemical_name_systematic
;
complex of 4,4'-dipyridylacetylene and
2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone
;
_chemical_name_common              '[4]+[1]-'
_chemical_formula_moiety           'C12 H9 N2, C6 H1 Cl2 O4'
_chemical_formula_sum              'C18 H10 Cl2 N2 O4'
_chemical_formula_weight            389.18
_chemical_melting_point             ?

_ccdc_compound_id                  '?'
_ccdc_biological_activity          '?'
_ccdc_polymorph                    '?'
_ccdc_chemdiag_type                '?'

_exptl_crystal_density_diffrn       1.599
_exptl_crystal_colour              'brown'

_diffrn_radiation_type             'Cu K\a'            
_diffrn_measurement_device         'EnrafNonius CAD4 diffractometer'
_ccdc_temp_data_collection          296
_ccdc_ls_R_squared                  0.0558
_refine_ls_abs_structure_details   '?'
_ccdc_disorder                     'none'
_ccdc_comments                     '?'

_cell_length_a                         12.7990(15)
_cell_length_b                         6.6870(13)
_cell_length_c                         18.925(3)
_cell_angle_alpha                      90.00
_cell_angle_beta                       93.641(10)
_cell_angle_gamma                      90.00
_cell_volume                           1616.4(4)
_cell_formula_units_Z                  4
_symmetry_cell_setting                 monoclinic
_symmetry_space_group_name_H-M        'P 21/n'
_symmetry_Int_Tables_number            14
_refine_ls_R_factor_obs                0.0558
_refine_ls_wR_factor_obs               0.1357
_refine_ls_goodness_of_fit_obs         0.979

#------------------------------------------------------------------------------

loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Cl1 Cl -0.40078(11) 0.8368(3) 0.02065(8) 0.0416(4) Uani 1 d . . 
Cl2 Cl 0.09062(10) 0.7348(2) 0.06396(7) 0.0380(4) Uani 1 d . . 
O1 O -0.2721(3) 0.8178(7) 0.1569(2) 0.0412(11) Uani 1 d . . 
O2 O -0.0636(3) 0.7793(8) 0.1719(2) 0.0504(13) Uani 1 d . . 
O3 O -0.2436(3) 0.8067(7) -0.0895(2) 0.0406(11) Uani 1 d . . 
O4 O -0.0356(3) 0.7576(7) -0.0723(2) 0.0386(10) Uani 1 d . . 
N1 N -0.4021(4) 0.2652(8) -0.2932(2) 0.0428(13) Uani 1 d . . 
N2 N -0.2940(4) 0.3245(8) 0.2108(2) 0.0399(12) Uani 1 d . . 
C1 C -0.4277(6) 0.1192(12) -0.2509(3) 0.050(2) Uani 1 d . . 
C2 C -0.4108(6) 0.1283(11) -0.1774(3) 0.049(2) Uani 1 d . . 
C3 C -0.3646(4) 0.2991(9) -0.1476(3) 0.0333(13) Uani 1 d . . 
C4 C -0.3361(5) 0.4496(11) -0.1923(3) 0.046(2) Uani 1 d . . 
C5 C -0.3570(5) 0.4266(12) -0.2648(3) 0.049(2) Uani 1 d . . 
C6 C -0.3449(5) 0.3161(10) -0.0719(3) 0.0377(14) Uani 1 d . . 
C7 C -0.3312(4) 0.3255(9) -0.0094(3) 0.0353(13) Uani 1 d . . 
C8 C -0.3175(4) 0.3300(9) 0.0663(3) 0.0334(13) Uani 1 d . . 
C9 C -0.4026(5) 0.3579(11) 0.1066(3) 0.045(2) Uani 1 d . . 
C10 C -0.3892(5) 0.3564(12) 0.1788(3) 0.047(2) Uani 1 d . . 
C11 C -0.2108(5) 0.3000(10) 0.1731(3) 0.0384(15) Uani 1 d . . 
C12 C -0.2194(5) 0.3007(10) 0.1010(3) 0.0372(14) Uani 1 d . . 
C13 C -0.2667(4) 0.8117(9) 0.0328(3) 0.0309(13) Uani 1 d . . 
C14 C -0.2224(4) 0.8063(8) 0.1008(3) 0.0286(12) Uani 1 d . . 
C15 C -0.1032(4) 0.7830(9) 0.1116(3) 0.0313(13) Uani 1 d . . 
C16 C -0.0433(4) 0.7641(8) 0.0508(3) 0.0289(12) Uani 1 d . . 
C17 C -0.0893(4) 0.7720(8) -0.0166(3) 0.0276(12) Uani 1 d . . 
C18 C -0.2077(4) 0.7984(8) -0.0278(3) 0.0290(12) Uani 1 d . . 
H2A H -0.2868(64) 0.3177(126) 0.2645(46) 0.099(30) Uiso 1 d . . 
H4A H -0.0737(74) 0.7639(133) -0.1200(52) 0.120(36) Uiso 1 d . . 
H1 H -0.4544(55) -0.0105(110) -0.2729(38) 0.069(23) Uiso 1 d . . 
H2 H -0.4303(54) 0.0170(105) -0.1450(36) 0.064(22) Uiso 1 d . . 
H4 H -0.3102(46) 0.5692(93) -0.1732(30) 0.043(18) Uiso 1 d . . 
H5 H -0.3392(48) 0.5394(98) -0.2923(33) 0.051(20) Uiso 1 d . . 
H9 H -0.4749(58) 0.3753(118) 0.0878(38) 0.085(26) Uiso 1 d . . 
H10 H -0.4480(61) 0.3508(118) 0.2063(41) 0.084(28) Uiso 1 d . . 
H11 H -0.1415(46) 0.2670(85) 0.2007(29) 0.039(16) Uiso 1 d . . 
H12 H -0.1616(50) 0.2864(91) 0.0782(34) 0.048(19) Uiso 1 d . . 


loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Cl1 C13 1.725(5) . ? 
Cl2 C16 1.727(5) . ? 
O1 C14 1.275(6) . ? 
O2 C15 1.220(6) . ? 
O3 C18 1.228(6) . ? 
O4 C17 1.297(6) . ? 
O4 H4A 1.00(10) . ? 
N1 C1 1.317(8) . ? 
N1 C5 1.322(8) . ? 
N2 C11 1.327(8) . ? 
N2 C10 1.343(8) . ? 
N2 H2A 1.02(9) . ? 
C1 C2 1.394(8) . ? 
C1 H1 1.01(7) . ? 
C2 C3 1.389(9) . ? 
C2 H2 1.01(7) . ? 
C3 C4 1.377(8) . ? 
C3 C6 1.444(7) . ? 
C4 C5 1.390(8) . ? 
C4 H4 0.93(6) . ? 
C5 H5 0.95(6) . ? 
C6 C7 1.186(7) . ? 
C7 C8 1.433(7) . ? 
C8 C9 1.381(8) . ? 
C8 C12 1.393(8) . ? 
C9 C10 1.368(8) . ? 
C9 H9 0.98(7) . ? 
C10 H10 0.94(8) . ? 
C11 C12 1.363(8) . ? 
C11 H11 1.02(6) . ? 
C12 H12 0.88(6) . ? 
C13 C14 1.374(7) . ? 
C13 C18 1.416(7) . ? 
C14 C15 1.534(7) . ? 
C15 C16 1.429(7) . ? 
C16 C17 1.372(6) . ? 
C17 C18 1.527(7) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C17 O4 H4A 118.6(54) . . ? 
C1 N1 C5 118.5(5) . . ? 
C11 N2 C10 120.9(5) . . ? 
C11 N2 H2A 120.5(47) . . ? 
C10 N2 H2A 118.6(47) . . ? 
N1 C1 C2 123.0(7) . . ? 
N1 C1 H1 118.4(42) . . ? 
C2 C1 H1 118.4(42) . . ? 
C3 C2 C1 118.4(6) . . ? 
C3 C2 H2 118.4(39) . . ? 
C1 C2 H2 123.2(40) . . ? 
C4 C3 C2 118.3(5) . . ? 
C4 C3 C6 121.0(6) . . ? 
C2 C3 C6 120.7(5) . . ? 
C3 C4 C5 118.9(6) . . ? 
C3 C4 H4 119.5(37) . . ? 
C5 C4 H4 121.3(37) . . ? 
N1 C5 C4 122.9(6) . . ? 
N1 C5 H5 122.6(39) . . ? 
C4 C5 H5 114.5(39) . . ? 
C7 C6 C3 177.8(7) . . ? 
C6 C7 C8 177.6(7) . . ? 
C9 C8 C12 118.6(5) . . ? 
C9 C8 C7 120.2(5) . . ? 
C12 C8 C7 121.2(5) . . ? 
C10 C9 C8 119.9(6) . . ? 
C10 C9 H9 114.9(44) . . ? 
C8 C9 H9 125.3(44) . . ? 
N2 C10 C9 120.2(6) . . ? 
N2 C10 H10 118.7(49) . . ? 
C9 C10 H10 119.9(49) . . ? 
N2 C11 C12 121.4(5) . . ? 
N2 C11 H11 116.9(31) . . ? 
C12 C11 H11 121.5(32) . . ? 
C11 C12 C8 119.0(6) . . ? 
C11 C12 H12 118.1(42) . . ? 
C8 C12 H12 122.9(42) . . ? 
C14 C13 C18 123.2(5) . . ? 
C14 C13 Cl1 118.4(4) . . ? 
C18 C13 Cl1 118.4(4) . . ? 
O1 C14 C13 125.5(5) . . ? 
O1 C14 C15 116.1(4) . . ? 
C13 C14 C15 118.4(5) . . ? 
O2 C15 C16 122.6(5) . . ? 
O2 C15 C14 118.6(5) . . ? 
C16 C15 C14 118.8(4) . . ? 
C17 C16 C15 121.7(5) . . ? 
C17 C16 Cl2 120.1(4) . . ? 
C15 C16 Cl2 118.2(4) . . ? 
O4 C17 C16 122.3(5) . . ? 
O4 C17 C18 117.9(4) . . ? 
C16 C17 C18 119.8(4) . . ? 
O3 C18 C13 125.5(5) . . ? 
O3 C18 C17 116.4(5) . . ? 
C13 C18 C17 118.1(4) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
 C5 N1 C1 C2 0.9(11) . . . . ? 
 N1 C1 C2 C3 -0.1(11) . . . . ? 
 C1 C2 C3 C4 -1.1(10) . . . . ? 
 C1 C2 C3 C6 -179.8(6) . . . . ? 
 C2 C3 C4 C5 1.5(10) . . . . ? 
 C6 C3 C4 C5 -179.8(6) . . . . ? 
 C1 N1 C5 C4 -0.5(11) . . . . ? 
 C3 C4 C5 N1 -0.8(11) . . . . ? 
 C4 C3 C6 C7 158.0(170) . . . . ? 
 C2 C3 C6 C7 -23.4(175) . . . . ? 
 C3 C6 C7 C8 9.8(307) . . . . ? 
 C6 C7 C8 C9 -60.7(158) . . . . ? 
 C6 C7 C8 C12 117.4(155) . . . . ? 
 C12 C8 C9 C10 0.0(11) . . . . ? 
 C7 C8 C9 C10 178.2(7) . . . . ? 
 C11 N2 C10 C9 2.1(11) . . . . ? 
 C8 C9 C10 N2 -1.2(12) . . . . ? 
 C10 N2 C11 C12 -1.8(10) . . . . ? 
 N2 C11 C12 C8 0.7(10) . . . . ? 
 C9 C8 C12 C11 0.2(10) . . . . ? 
 C7 C8 C12 C11 -177.9(6) . . . . ? 
 C18 C13 C14 O1 180.0(6) . . . . ? 
 Cl1 C13 C14 O1 0.2(9) . . . . ? 
 C18 C13 C14 C15 -0.5(9) . . . . ? 
 Cl1 C13 C14 C15 179.7(4) . . . . ? 
 O1 C14 C15 O2 -0.8(8) . . . . ? 
 C13 C14 C15 O2 179.6(6) . . . . ? 
 O1 C14 C15 C16 178.4(5) . . . . ? 
 C13 C14 C15 C16 -1.2(8) . . . . ? 
 O2 C15 C16 C17 -178.9(6) . . . . ? 
 C14 C15 C16 C17 1.9(9) . . . . ? 
 O2 C15 C16 Cl2 0.0(9) . . . . ? 
 C14 C15 C16 Cl2 -179.2(4) . . . . ? 
 C15 C16 C17 O4 179.1(5) . . . . ? 
 Cl2 C16 C17 O4 0.2(8) . . . . ? 
 C15 C16 C17 C18 -1.0(9) . . . . ? 
 Cl2 C16 C17 C18 -179.9(4) . . . . ? 
 C14 C13 C18 O3 -178.4(6) . . . . ? 
 Cl1 C13 C18 O3 1.4(9) . . . . ? 
 C14 C13 C18 C17 1.4(8) . . . . ? 
 Cl1 C13 C18 C17 -178.8(4) . . . . ? 
 O4 C17 C18 O3 -0.9(8) . . . . ? 
 C16 C17 C18 O3 179.2(5) . . . . ? 
 O4 C17 C18 C13 179.2(5) . . . . ? 
 C16 C17 C18 C13 -0.7(8) . . . . ? 

#===END

