 
data_a 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C18 H25 N3 O2' 
_chemical_formula_sum             'C18 H25 N3 O2' 
_chemical_formula_weight          315.41 
 
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    'P 21/n'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    5.7118(2) 
_cell_length_b                    25.8049(10) 
_cell_length_c                    11.8905(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  94.801(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1746.4(1) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     140(2) 
_cell_measurement_reflns_used       1785 
_cell_measurement_theta_min       2.3
_cell_measurement_theta_max       27.8
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colorless
_exptl_crystal_size_max           0.38 
_exptl_crystal_size_mid           0.26 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.200 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              680 
_exptl_absorpt_coefficient_mu     0.079 
_exptl_absorpt_correction_type    None
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_diffrn_ambient_temperature       140(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   'Bruker SMART APEX diffractometer'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0
_diffrn_reflns_number             9482 
_diffrn_reflns_av_R_equivalents   0.0895 
_diffrn_reflns_av_sigmaI/netI     0.1243 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -33 
_diffrn_reflns_limit_k_max        33 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          1.58 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              3981 
_reflns_number_gt                 2189 
_reflns_threshold_expression      I>2σ(I) 
 
_computing_data_collection        'APEX2 software (Bruker, 2008)'
_computing_cell_refinement        'SAINT (Bruker, 2008)'
_computing_data_reduction         SAINT
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'X-Seed (Barbour, 2001)' 
_computing_publication_material   'publCIF (Westrip, 2009)'
 
_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)+(0.1145P)²+0.5103P] 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      SHELXL 
_refine_ls_extinction_coef        0.006(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3981 
_refine_ls_number_parameters      220 
_refine_ls_number_restraints      3 
_refine_ls_R_factor_all           0.1449 
_refine_ls_R_factor_gt            0.0806 
_refine_ls_wR_factor_ref          0.2388 
_refine_ls_wR_factor_gt           0.1985 
_refine_ls_goodness_of_fit_ref    1.037 
_refine_ls_restrained_S_all       1.037 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.001
 
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 
O1 O -0.1002(4) 0.25586(9) 0.5930(2) 0.0276(6) Uani 1 1 d . . . 
O2 O -0.1762(4) 0.30179(9) 0.9009(2) 0.0250(6) Uani 1 1 d . . . 
N1 N 0.1722(5) 0.19283(10) 0.6263(2) 0.0195(6) Uani 1 1 d D . . 
H1 H 0.222(6) 0.1989(12) 0.5593(16) 0.023 Uiso 1 1 d D . . 
N2 N 0.2638(4) 0.20469(10) 0.8632(2) 0.0170(6) Uani 1 1 d D . . 
H2 H 0.333(6) 0.2070(12) 0.9318(14) 0.020 Uiso 1 1 d D . . 
N3 N 0.1876(5) 0.30586(10) 0.8391(2) 0.0212(6) Uani 1 1 d D . . 
H3 H 0.305(4) 0.2855(11) 0.825(3) 0.025 Uiso 1 1 d D . . 
C1 C 0.2837(5) 0.15287(12) 0.6927(3) 0.0186(7) Uani 1 1 d . . . 
C2 C 0.3718(6) 0.11016(13) 0.6401(3) 0.0241(8) Uani 1 1 d . . . 
H2A H 0.3432 0.1064 0.5606 0.029 Uiso 1 1 calc R . . 
C3 C 0.5011(6) 0.07270(14) 0.7015(3) 0.0275(8) Uani 1 1 d . . . 
H3A H 0.5645 0.0442 0.6637 0.033 Uiso 1 1 calc R . . 
C4 C 0.5385(6) 0.07677(13) 0.8184(3) 0.0242(8) Uani 1 1 d . . . 
C5 C 0.4436(6) 0.11873(12) 0.8708(3) 0.0201(7) Uani 1 1 d . . . 
H5 H 0.4624 0.1210 0.9508 0.024 Uiso 1 1 calc R . . 
C6 C 0.3209(5) 0.15799(12) 0.8100(3) 0.0170(7) Uani 1 1 d . . . 
C7 C 0.6898(8) 0.03781(14) 0.8858(3) 0.0374(10) Uani 1 1 d . . . 
H7A H 0.6907 0.0050 0.8441 0.056 Uiso 1 1 calc R . . 
H7B H 0.6262 0.0320 0.9588 0.056 Uiso 1 1 calc R . . 
H7C H 0.8506 0.0511 0.8981 0.056 Uiso 1 1 calc R . . 
C8 C 0.0165(5) 0.22066(12) 0.8679(3) 0.0175(7) Uani 1 1 d . . . 
C9 C -0.1261(6) 0.20390(12) 0.7589(3) 0.0188(7) Uani 1 1 d . . . 
H9A H -0.1424 0.1657 0.7591 0.023 Uiso 1 1 calc R . . 
H9B H -0.2856 0.2190 0.7579 0.023 Uiso 1 1 calc R . . 
C10 C -0.0176(6) 0.22013(13) 0.6529(3) 0.0195(7) Uani 1 1 d . . . 
C11 C -0.0879(6) 0.19730(12) 0.9707(3) 0.0215(7) Uani 1 1 d . . . 
H11A H -0.0873 0.1594 0.9649 0.032 Uiso 1 1 calc R . . 
H11B H -0.2497 0.2095 0.9736 0.032 Uiso 1 1 calc R . . 
H11C H 0.0062 0.2080 1.0395 0.032 Uiso 1 1 calc R . . 
C12 C 0.0047(6) 0.28003(12) 0.8725(3) 0.0184(7) Uani 1 1 d . . . 
C13 C 0.1996(6) 0.36175(13) 0.8312(3) 0.0218(7) Uani 1 1 d . . . 
H13 H 0.0358 0.3757 0.8249 0.026 Uiso 1 1 calc R . . 
C14 C 0.3318(7) 0.38503(13) 0.9362(3) 0.0289(8) Uani 1 1 d . . . 
H14A H 0.2515 0.3753 1.0037 0.035 Uiso 1 1 calc R . . 
H14B H 0.4931 0.3707 0.9450 0.035 Uiso 1 1 calc R . . 
C15 C 0.3440(8) 0.44361(14) 0.9279(3) 0.0375(10) Uani 1 1 d . . . 
H15A H 0.1833 0.4582 0.9252 0.045 Uiso 1 1 calc R . . 
H15B H 0.4346 0.4575 0.9959 0.045 Uiso 1 1 calc R . . 
C16 C 0.4597(8) 0.46015(15) 0.8237(4) 0.0400(10) Uani 1 1 d . . . 
H16A H 0.6263 0.4492 0.8307 0.048 Uiso 1 1 calc R . . 
H16B H 0.4554 0.4984 0.8175 0.048 Uiso 1 1 calc R . . 
C17 C 0.3359(9) 0.43651(15) 0.7179(4) 0.0435(11) Uani 1 1 d . . . 
H17A H 0.1760 0.4514 0.7054 0.052 Uiso 1 1 calc R . . 
H17B H 0.4230 0.4456 0.6521 0.052 Uiso 1 1 calc R . . 
C18 C 0.3180(8) 0.37793(14) 0.7262(3) 0.0338(9) Uani 1 1 d . . . 
H18A H 0.4774 0.3627 0.7290 0.041 Uiso 1 1 calc R . . 
H18B H 0.2263 0.3644 0.6581 0.041 Uiso 1 1 calc R . . 
 
 
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 
O1 C10 1.234(4) . ? 
O2 C12 1.247(4) . ? 
N1 C10 1.352(4) . ? 
N1 C1 1.417(4) . ? 
N2 C6 1.412(4) . ? 
N2 C8 1.477(4) . ? 
N3 C12 1.327(4) . ? 
N3 C13 1.447(4) . ? 
C1 C2 1.383(5) . ? 
C1 C6 1.399(4) . ? 
C2 C3 1.387(5) . ? 
C3 C4 1.392(5) . ? 
C4 C5 1.382(5) . ? 
C4 C7 1.511(5) . ? 
C5 C6 1.398(4) . ? 
C8 C11 1.528(4) . ? 
C8 C12 1.535(5) . ? 
C8 C9 1.534(4) . ? 
C9 C10 1.510(5) . ? 
C13 C14 1.526(5) . ? 
C13 C18 1.528(5) . ? 
C14 C15 1.517(5) . ? 
C15 C16 1.514(6) . ? 
C16 C17 1.518(6) . ? 
C17 C18 1.519(5) . ? 
 
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 
C10 N1 C1 125.5(3) . . ? 
C6 N2 C8 120.8(2) . . ? 
C12 N3 C13 124.2(3) . . ? 
C2 C1 C6 119.7(3) . . ? 
C2 C1 N1 119.4(3) . . ? 
C6 C1 N1 120.7(3) . . ? 
C1 C2 C3 121.0(3) . . ? 
C2 C3 C4 120.3(3) . . ? 
C5 C4 C3 118.4(3) . . ? 
C5 C4 C7 120.7(3) . . ? 
C3 C4 C7 120.8(3) . . ? 
C4 C5 C6 122.2(3) . . ? 
C5 C6 C1 118.3(3) . . ? 
C5 C6 N2 120.8(3) . . ? 
C1 C6 N2 120.4(3) . . ? 
N2 C8 C11 111.0(3) . . ? 
N2 C8 C12 108.9(3) . . ? 
C11 C8 C12 110.2(3) . . ? 
N2 C8 C9 109.3(2) . . ? 
C11 C8 C9 110.4(3) . . ? 
C12 C8 C9 106.8(3) . . ? 
C10 C9 C8 113.7(3) . . ? 
O1 C10 N1 122.0(3) . . ? 
O1 C10 C9 121.7(3) . . ? 
N1 C10 C9 116.4(3) . . ? 
O2 C12 N3 123.1(3) . . ? 
O2 C12 C8 119.9(3) . . ? 
N3 C12 C8 116.9(3) . . ? 
N3 C13 C14 111.2(3) . . ? 
N3 C13 C18 110.6(3) . . ? 
C14 C13 C18 109.8(3) . . ? 
C15 C14 C13 111.2(3) . . ? 
C16 C15 C14 111.1(3) . . ? 
C15 C16 C17 111.1(3) . . ? 
C18 C17 C16 112.1(3) . . ? 
C17 C18 C13 111.2(3) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N1 H1 O2  0.88(1) 2.02(1) 2.888(3) 169(3) 4_665 
N2 H2 O1  0.88(1) 2.15(2) 2.959(3) 153(3) 4_666 
 
_diffrn_measured_fraction_theta_max    0.989 
_diffrn_reflns_theta_full              27.50 
_diffrn_measured_fraction_theta_full   0.989 
_refine_diff_density_max    0.559 
_refine_diff_density_min   -0.319 
_refine_diff_density_rms    0.084 
