 
data_cu_d8v191195_0m 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C12 H15 N O' 
_chemical_formula_weight          189.25 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            19 
_space_group_name_H-M_alt         'P 21 21 21' 
_space_group_name_Hall            'P 2ac 2ab' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
  
_cell_length_a                    7.8115(3) 
_cell_length_b                    9.4031(4) 
_cell_length_c                    14.7571(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      1083.94(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     6498 
_cell_measurement_theta_min       9.405 
_cell_measurement_theta_max       139.737 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.160 
_exptl_crystal_F_000              408 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.180 
_exptl_crystal_size_mid           0.160 
_exptl_crystal_size_min           0.130 
_exptl_absorpt_coefficient_mu     0.578 
_shelx_estimated_absorpt_T_min    0.903 
_shelx_estimated_absorpt_T_max    0.929 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5889 
_exptl_absorpt_correction_T_max   0.7456 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             9219 
_diffrn_reflns_av_unetI/netI      0.0251 
_diffrn_reflns_av_R_equivalents   0.0350 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          5.579 
_diffrn_reflns_theta_max          67.464 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.976 
_diffrn_measured_fraction_theta_full  0.973 
_diffrn_reflns_Laue_measured_fraction_max    0.976 
_diffrn_reflns_Laue_measured_fraction_full   0.973 
_diffrn_reflns_point_group_measured_fraction_max   0.979 
_diffrn_reflns_point_group_measured_fraction_full  0.975 
_reflns_number_total              1906 
_reflns_number_gt                 1844 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.700 
_reflns_Friedel_fraction_max      0.982 
_reflns_Friedel_fraction_full     0.979 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 ? 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0601P)²+0.0514P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 738 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
; 
_refine_ls_abs_structure_Flack    0.06(11) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          1906 
_refine_ls_number_parameters      129 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0368 
_refine_ls_R_factor_gt            0.0357 
_refine_ls_wR_factor_ref          0.1010 
_refine_ls_wR_factor_gt           0.0999 
_refine_ls_goodness_of_fit_ref    1.079 
_refine_ls_restrained_S_all       1.079 
_refine_ls_shift/su_max           0.005 
_refine_ls_shift/su_mean          0.000 
  
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_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.8092(2) 0.25538(16) 0.60345(11) 0.0777(5) Uani 1 1 d . . . . . 
N1 N 0.5592(2) 0.35824(17) 0.63897(11) 0.0649(4) Uani 1 1 d . . . . . 
C1 C 0.9161(3) 0.5943(2) 0.62183(14) 0.0670(5) Uani 1 1 d . . . . . 
H1 H 0.9538 0.5006 0.6198 0.080 Uiso 1 1 calc R U . . . 
C2 C 0.9703(3) 0.6821(2) 0.69097(16) 0.0770(6) Uani 1 1 d . . . . . 
H2 H 1.0415 0.6461 0.7359 0.092 Uiso 1 1 calc R U . . . 
C3 C 0.9207(3) 0.8214(2) 0.69422(16) 0.0784(6) Uani 1 1 d . . . . . 
H3 H 0.9593 0.8804 0.7405 0.094 Uiso 1 1 calc R U . . . 
C4 C 0.8138(3) 0.8732(2) 0.62868(18) 0.0783(6) Uani 1 1 d . . . . . 
H4 H 0.7802 0.9680 0.6303 0.094 Uiso 1 1 calc R U . . . 
C5 C 0.7551(3) 0.7856(2) 0.55997(16) 0.0658(5) Uani 1 1 d . . . . . 
H5 H 0.6808 0.8219 0.5165 0.079 Uiso 1 1 calc R U . . . 
C6 C 0.8057(2) 0.64432(19) 0.55509(12) 0.0557(4) Uani 1 1 d . . . . . 
C7 C 0.7419(3) 0.5553(2) 0.47901(14) 0.0674(5) Uani 1 1 d . . . . . 
H7 H 0.6781 0.6088 0.4332 0.081 Uiso 1 1 calc R U . . . 
C8 C 0.8404(4) 0.4323(3) 0.44131(17) 0.0848(7) Uani 1 1 d . . . . . 
H8A H 0.8396 0.4192 0.3761 0.102 Uiso 1 1 calc R U . . . 
H8B H 0.9474 0.4074 0.4707 0.102 Uiso 1 1 calc R U . . . 
C9 C 0.6794(3) 0.4026(2) 0.49123(13) 0.0685(5) Uani 1 1 d . . . . . 
H9 H 0.5815 0.3752 0.4536 0.082 Uiso 1 1 calc R U . . . 
C10 C 0.6886(3) 0.33260(18) 0.58165(13) 0.0594(5) Uani 1 1 d . . . . . 
C11 C 0.4137(3) 0.4471(3) 0.61660(19) 0.0875(7) Uani 1 1 d . . . . . 
H11A H 0.4499 0.5228 0.5774 0.131 Uiso 1 1 calc R U . . . 
H11B H 0.3664 0.4866 0.6711 0.131 Uiso 1 1 calc R U . . . 
H11C H 0.3283 0.3910 0.5865 0.131 Uiso 1 1 calc R U . . . 
C12 C 0.5624(4) 0.2944(3) 0.72844(16) 0.0897(7) Uani 1 1 d . . . . . 
H12A H 0.6428 0.2172 0.7291 0.135 Uiso 1 1 calc R U . . . 
H12B H 0.4504 0.2593 0.7432 0.135 Uiso 1 1 calc R U . . . 
H12C H 0.5961 0.3646 0.7722 0.135 Uiso 1 1 calc R U . . . 
  
  
_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 
O1 C10 1.232(2) . ? 
N1 C10 1.340(3) . ? 
N1 C11 1.449(3) . ? 
N1 C12 1.451(3) . ? 
C1 C2 1.379(3) . ? 
C1 C6 1.391(3) . ? 
C1 H1 0.9300 . ? 
C2 C3 1.367(4) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.367(3) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.385(3) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.388(3) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.486(3) . ? 
C7 C8 1.496(3) . ? 
C7 C9 1.527(3) . ? 
C7 H7 0.9800 . ? 
C8 C9 1.484(3) . ? 
C8 H8A 0.9700 . ? 
C8 H8B 0.9700 . ? 
C9 C10 1.489(3) . ? 
C9 H9 0.9800 . ? 
C11 H11A 0.9600 . ? 
C11 H11B 0.9600 . ? 
C11 H11C 0.9600 . ? 
C12 H12A 0.9600 . ? 
C12 H12B 0.9600 . ? 
C12 H12C 0.9600 . ? 
  
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 C11 123.49(19) . . ? 
C10 N1 C12 119.17(18) . . ? 
C11 N1 C12 117.3(2) . . ? 
C2 C1 C6 120.78(19) . . ? 
C2 C1 H1 119.6 . . ? 
C6 C1 H1 119.6 . . ? 
C3 C2 C1 120.8(2) . . ? 
C3 C2 H2 119.6 . . ? 
C1 C2 H2 119.6 . . ? 
C2 C3 C4 119.3(2) . . ? 
C2 C3 H3 120.3 . . ? 
C4 C3 H3 120.3 . . ? 
C3 C4 C5 120.56(19) . . ? 
C3 C4 H4 119.7 . . ? 
C5 C4 H4 119.7 . . ? 
C4 C5 C6 120.9(2) . . ? 
C4 C5 H5 119.6 . . ? 
C6 C5 H5 119.6 . . ? 
C5 C6 C1 117.60(19) . . ? 
C5 C6 C7 118.89(18) . . ? 
C1 C6 C7 123.51(17) . . ? 
C6 C7 C8 122.97(19) . . ? 
C6 C7 C9 123.19(17) . . ? 
C8 C7 C9 58.77(15) . . ? 
C6 C7 H7 113.7 . . ? 
C8 C7 H7 113.7 . . ? 
C9 C7 H7 113.7 . . ? 
C9 C8 C7 61.66(15) . . ? 
C9 C8 H8A 117.6 . . ? 
C7 C8 H8A 117.6 . . ? 
C9 C8 H8B 117.6 . . ? 
C7 C8 H8B 117.6 . . ? 
H8A C8 H8B 114.7 . . ? 
C8 C9 C10 119.2(2) . . ? 
C8 C9 C7 59.57(15) . . ? 
C10 C9 C7 120.37(16) . . ? 
C8 C9 H9 115.4 . . ? 
C10 C9 H9 115.4 . . ? 
C7 C9 H9 115.4 . . ? 
O1 C10 N1 121.20(19) . . ? 
O1 C10 C9 122.06(19) . . ? 
N1 C10 C9 116.73(17) . . ? 
N1 C11 H11A 109.5 . . ? 
N1 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
N1 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
N1 C12 H12A 109.5 . . ? 
N1 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
N1 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
  
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 
C6 C1 C2 C3 -1.8(4) . . . . ? 
C1 C2 C3 C4 1.0(4) . . . . ? 
C2 C3 C4 C5 0.5(3) . . . . ? 
C3 C4 C5 C6 -1.2(3) . . . . ? 
C4 C5 C6 C1 0.4(3) . . . . ? 
C4 C5 C6 C7 -178.79(19) . . . . ? 
C2 C1 C6 C5 1.1(3) . . . . ? 
C2 C1 C6 C7 -179.8(2) . . . . ? 
C5 C6 C7 C8 151.0(2) . . . . ? 
C1 C6 C7 C8 -28.1(3) . . . . ? 
C5 C6 C7 C9 -137.3(2) . . . . ? 
C1 C6 C7 C9 43.6(3) . . . . ? 
C6 C7 C8 C9 111.7(2) . . . . ? 
C7 C8 C9 C10 -110.1(2) . . . . ? 
C6 C7 C9 C8 -111.3(2) . . . . ? 
C6 C7 C9 C10 -3.2(3) . . . . ? 
C8 C7 C9 C10 108.1(2) . . . . ? 
C11 N1 C10 O1 -179.47(19) . . . . ? 
C12 N1 C10 O1 0.4(3) . . . . ? 
C11 N1 C10 C9 0.9(3) . . . . ? 
C12 N1 C10 C9 -179.2(2) . . . . ? 
C8 C9 C10 O1 -25.8(3) . . . . ? 
C7 C9 C10 O1 -95.7(2) . . . . ? 
C8 C9 C10 N1 153.78(19) . . . . ? 
C7 C9 C10 N1 84.0(2) . . . . ? 
  
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 
C9 H9 O1  0.98 2.60 3.538(3) 161.4 4_456 
  
_refine_diff_density_max    0.092 
_refine_diff_density_min   -0.092 
_refine_diff_density_rms    0.022 
  
_shelxl_version_number 2013-4 
  
  
  
