
data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Dr Yoshihiko Yamamoto'
_publ_contact_author_address     
;
Department of Applied Chemistry, Graduate School of Engineering
Nagoya University
Chikusa
Nagoya
464-8603
JAPAN
;

_publ_contact_author_email       YAMAMOTO@APCHEM.NAGOYA-U.AC.JP

_publ_section_title              
;
Synthesis of benzo-fused lactams and lactones via
Ru(II)-catalyzed cycloaddition of amide- and ester-tethered a,w-diynes
with terminal alkynes: Electronic directing effect of internal
conjugated carbonyl group
;
loop_
_publ_author_name
'Yoshihiko Yamamoto'
'Jun-ichi Ishii'
'Kenji Itoh'
'Keisuke Kinpara'
'Hisao Nishiyama'
'Tomoaki Saigoku'

data_ykin31
_database_code_depnum_ccdc_archive 'CCDC 224127'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O'
_chemical_formula_weight         299.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3987(6)
_cell_length_b                   5.7449(4)
_cell_length_c                   15.9653(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.7740(10)
_cell_angle_gamma                90.00
_cell_volume                     770.25(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.8
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.518165
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5753
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         29.14
_reflns_number_total             3608
_reflns_number_gt                3456
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1515P)²+0.1588P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.4(15)
_refine_ls_number_reflns         3608
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   0.719
_refine_ls_restrained_S_all      0.719
_refine_ls_shift/su_max          0.077
_refine_ls_shift/su_mean         0.012

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
C1 C 0.2718(2) 0.9190(3) 0.38698(10) 0.0394(4) Uani 1 1 d . . .
H1 H 0.3358 1.0279 0.4144 0.047 Uiso 1 1 calc R . .
C2 C 0.23028(19) 0.9553(3) 0.30327(10) 0.0404(4) Uani 1 1 d . . .
H2 H 0.2658 1.0863 0.2749 0.048 Uiso 1 1 calc R . .
C3 C 0.13476(15) 0.7915(3) 0.26321(8) 0.0284(3) Uani 1 1 d . . .
C4 C 0.07161(15) 0.7877(3) 0.17522(9) 0.0312(3) Uani 1 1 d . . .
C5 C -0.0160(2) 0.4474(3) 0.24574(10) 0.0399(4) Uani 1 1 d . . .
H5A H 0.0310 0.2949 0.2377 0.048 Uiso 1 1 calc R . .
H5B H -0.1238 0.4290 0.2658 0.048 Uiso 1 1 calc R . .
C6 C 0.08343(15) 0.5938(2) 0.30518(9) 0.0293(3) Uani 1 1 d . . .
C7 C 0.12387(17) 0.5571(3) 0.38915(9) 0.0328(3) Uani 1 1 d . . .
H7 H 0.0880 0.4251 0.4169 0.039 Uiso 1 1 calc R . .
C8 C 0.21946(15) 0.7213(2) 0.43152(8) 0.0266(3) Uani 1 1 d . . .
C9 C 0.26785(15) 0.6901(3) 0.52172(9) 0.0274(3) Uani 1 1 d . . .
C10 C 0.3669(2) 0.8515(3) 0.56255(11) 0.0417(4) Uani 1 1 d . . .
H10 H 0.4018 0.9814 0.5333 0.050 Uiso 1 1 calc R . .
C11 C 0.4147(2) 0.8224(4) 0.64607(11) 0.0450(4) Uani 1 1 d . . .
H11 H 0.4808 0.9321 0.6715 0.054 Uiso 1 1 calc R . .
C12 C 0.36431(17) 0.6318(3) 0.69085(9) 0.0380(3) Uani 1 1 d . . .
H12 H 0.3954 0.6126 0.7466 0.046 Uiso 1 1 calc R . .
C13 C 0.2666(2) 0.4687(4) 0.65181(11) 0.0484(4) Uani 1 1 d . . .
H13 H 0.2331 0.3386 0.6814 0.058 Uiso 1 1 calc R . .
C14 C 0.2179(2) 0.4981(4) 0.56825(11) 0.0453(4) Uani 1 1 d . . .
H14 H 0.1513 0.3881 0.5433 0.054 Uiso 1 1 calc R . .
C15 C -0.08571(17) 0.4986(3) 0.09090(9) 0.0369(3) Uani 1 1 d . . .
H15A H -0.0317 0.3572 0.0740 0.044 Uiso 1 1 calc R . .
H15B H -0.0717 0.6133 0.0470 0.044 Uiso 1 1 calc R . .
C16 C -0.26205(15) 0.4483(3) 0.10021(8) 0.0284(3) Uani 1 1 d . . .
C17 C -0.36181(17) 0.6125(3) 0.13739(9) 0.0337(3) Uani 1 1 d . . .
H17 H -0.3193 0.7515 0.1575 0.040 Uiso 1 1 calc R . .
C18 C -0.52436(19) 0.5693(3) 0.14458(10) 0.0411(4) Uani 1 1 d . . .
H18 H -0.5898 0.6798 0.1691 0.049 Uiso 1 1 calc R . .
C19 C -0.58930(18) 0.3608(4) 0.11509(10) 0.0412(4) Uani 1 1 d . . .
H19 H -0.6976 0.3316 0.1203 0.049 Uiso 1 1 calc R . .
C20 C -0.49072(19) 0.1964(3) 0.07774(10) 0.0386(3) Uani 1 1 d . . .
H20 H -0.5336 0.0578 0.0575 0.046 Uiso 1 1 calc R . .
C21 C -0.32755(18) 0.2397(3) 0.07069(9) 0.0331(3) Uani 1 1 d . . .
H21 H -0.2622 0.1289 0.0462 0.040 Uiso 1 1 calc R . .
N1 N -0.01306(15) 0.5848(3) 0.16845(8) 0.0345(3) Uani 1 1 d . . .
O1 O 0.09042(16) 0.9337(3) 0.12026(8) 0.0475(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0420(7) 0.0401(9) 0.0358(7) 0.0033(7) -0.0059(5) -0.0179(6)
C2 0.0449(8) 0.0398(8) 0.0363(7) 0.0088(7) -0.0044(6) -0.0193(7)
C3 0.0234(5) 0.0310(7) 0.0307(6) 0.0026(6) 0.0014(4) -0.0031(5)
C4 0.0242(5) 0.0380(8) 0.0314(6) 0.0004(6) 0.0015(4) -0.0035(5)
C5 0.0486(8) 0.0350(8) 0.0359(7) 0.0029(7) -0.0087(6) -0.0158(6)
C6 0.0280(6) 0.0259(6) 0.0340(6) -0.0003(5) -0.0011(4) -0.0035(5)
C7 0.0372(6) 0.0263(7) 0.0348(7) 0.0029(6) -0.0020(5) -0.0061(5)
C8 0.0218(5) 0.0279(6) 0.0302(6) -0.0008(5) 0.0013(4) 0.0002(4)
C9 0.0229(5) 0.0287(6) 0.0305(6) -0.0004(5) 0.0028(4) 0.0037(4)
C10 0.0513(9) 0.0362(8) 0.0373(7) 0.0024(7) -0.0068(6) -0.0085(7)
C11 0.0524(9) 0.0450(10) 0.0374(8) -0.0039(7) -0.0088(6) -0.0060(7)
C12 0.0342(7) 0.0504(10) 0.0293(6) -0.0003(7) 0.0009(5) 0.0067(6)
C13 0.0553(9) 0.0530(11) 0.0369(8) 0.0117(8) -0.0008(7) -0.0129(9)
C14 0.0504(9) 0.0487(10) 0.0367(7) 0.0069(7) -0.0045(6) -0.0200(8)
C15 0.0313(6) 0.0482(9) 0.0313(6) -0.0069(6) 0.0006(5) -0.0053(6)
C16 0.0303(6) 0.0295(6) 0.0254(5) -0.0013(5) -0.0026(4) -0.0005(5)
C17 0.0378(7) 0.0295(7) 0.0337(6) -0.0040(6) -0.0014(5) 0.0010(5)
C18 0.0358(7) 0.0470(9) 0.0405(7) 0.0010(7) 0.0031(6) 0.0101(7)
C19 0.0290(6) 0.0553(10) 0.0393(7) 0.0109(7) -0.0029(5) -0.0034(6)
C20 0.0433(8) 0.0348(8) 0.0372(7) 0.0046(6) -0.0103(6) -0.0106(6)
C21 0.0386(7) 0.0292(7) 0.0314(6) -0.0039(6) -0.0040(5) 0.0004(5)
N1 0.0325(5) 0.0384(7) 0.0324(6) -0.0003(5) -0.0029(4) -0.0083(5)
O1 0.0547(7) 0.0521(8) 0.0357(5) 0.0116(6) -0.0047(5) -0.0167(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.392(2) . ?
C1 C8 1.413(2) . ?
C2 C3 1.387(2) . ?
C3 C6 1.3903(18) . ?
C3 C4 1.4951(18) . ?
C4 O1 1.2256(19) . ?
C4 N1 1.369(2) . ?
C5 N1 1.465(2) . ?
C5 C6 1.511(2) . ?
C6 C7 1.395(2) . ?
C7 C8 1.4062(18) . ?
C8 C9 1.5018(17) . ?
C9 C14 1.398(2) . ?
C9 C10 1.401(2) . ?
C10 C11 1.397(2) . ?
C11 C12 1.378(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.400(2) . ?
C15 N1 1.4595(19) . ?
C15 C16 1.5182(19) . ?
C16 C21 1.398(2) . ?
C16 C17 1.3991(19) . ?
C17 C18 1.394(2) . ?
C18 C19 1.395(3) . ?
C19 C20 1.395(3) . ?
C20 C21 1.399(2) . ?

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 C1 C8 121.84(13) . . ?
C3 C2 C1 118.49(14) . . ?
C2 C3 C6 120.87(13) . . ?
C2 C3 C4 129.71(13) . . ?
C6 C3 C4 109.42(12) . . ?
O1 C4 N1 126.73(14) . . ?
O1 C4 C3 127.96(14) . . ?
N1 C4 C3 105.31(12) . . ?
N1 C5 C6 102.32(12) . . ?
C3 C6 C7 120.93(13) . . ?
C3 C6 C5 108.93(13) . . ?
C7 C6 C5 130.14(13) . . ?
C6 C7 C8 119.39(13) . . ?
C7 C8 C1 118.47(12) . . ?
C7 C8 C9 121.78(12) . . ?
C1 C8 C9 119.74(12) . . ?
C14 C9 C10 117.11(13) . . ?
C14 C9 C8 121.63(13) . . ?
C10 C9 C8 121.25(13) . . ?
C11 C10 C9 121.75(16) . . ?
C12 C11 C10 120.26(16) . . ?
C11 C12 C13 119.18(14) . . ?
C12 C13 C14 120.64(17) . . ?
C9 C14 C13 121.06(16) . . ?
N1 C15 C16 112.26(11) . . ?
C21 C16 C17 119.07(12) . . ?
C21 C16 C15 120.66(13) . . ?
C17 C16 C15 120.26(13) . . ?
C18 C17 C16 120.51(15) . . ?
C17 C18 C19 120.27(15) . . ?
C20 C19 C18 119.59(14) . . ?
C19 C20 C21 120.12(15) . . ?
C20 C21 C16 120.44(14) . . ?
C4 N1 C5 114.01(12) . . ?
C4 N1 C15 124.53(13) . . ?
C5 N1 C15 121.32(14) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.074



