 
data_cu_ZZX652Cu2_0m 
  
_audit_creation_method            'SHELXL-2019/3' 
_shelx_SHELXL_version_number      '2019/3' 
_chemical_formula_moiety          'C20 H18 N2 O' 
_chemical_formula_sum             'C20 H18 N2 O' 
_chemical_formula_weight          302.36 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   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       monoclinic 
_space_group_IT_number            5 
_space_group_name_H-M_alt         'C 2' 
_space_group_name_Hall            'C 2y' 
  
_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, y, -z' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z' 
  
_cell_length_a                    17.4943(12) 
_cell_length_b                    7.3922(5) 
_cell_length_c                    12.5448(8) 
_cell_angle_alpha                 90 
_cell_angle_beta                  103.709(2) 
_cell_angle_gamma                 90 
_cell_volume                      1576.09(18) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     108(2) 
_cell_measurement_reflns_used     9911 
_cell_measurement_theta_min       3.625 
_cell_measurement_theta_max       68.516 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_diffrn     1.274 
_exptl_crystal_F_000              640 
_exptl_crystal_size_max           0.320 
_exptl_crystal_size_mid           0.240 
_exptl_crystal_size_min           0.160 
_exptl_absorpt_coefficient_mu     0.624 
_shelx_estimated_absorpt_T_min    0.825 
_shelx_estimated_absorpt_T_max    0.907 
_exptl_absorpt_correction_type   numerical 
_exptl_absorpt_correction_T_min  0.7772 
_exptl_absorpt_correction_T_max  1.0000 
_exptl_absorpt_process_details 
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
; 
_diffrn_ambient_temperature       108(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'sealed X-ray tube' 
_diffrn_measurement_device        'κ-geometry diffractometer'
_diffrn_measurement_device_type   'Bruker D8 Venture dual source kappa CPAD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector                  CPAD
_diffrn_detector_area_resol_mean  7.41       
_diffrn_detector_dtime            0
_diffrn_detector_type             'Bruker Photon III C7'
_diffrn_reflns_number             11966 
_diffrn_reflns_av_unetI/netI      0.0304 
_diffrn_reflns_av_R_equivalents   0.0313 
_diffrn_reflns_limit_h_min        -21 
_diffrn_reflns_limit_h_max        20 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          3.627 
_diffrn_reflns_theta_max          68.742 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.988 
_diffrn_measured_fraction_theta_full  0.990 
_diffrn_reflns_Laue_measured_fraction_max    0.988 
_diffrn_reflns_Laue_measured_fraction_full   0.990 
_diffrn_reflns_point_group_measured_fraction_max   0.966 
_diffrn_reflns_point_group_measured_fraction_full  0.968 
_reflns_number_total              2821 
_reflns_number_gt                 2779 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.804 
_reflns_Friedel_fraction_max      0.940 
_reflns_Friedel_fraction_full     0.943 
  
_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 APEX5 v2023-9.2 (Bruker AXS, 2023)' 
_computing_cell_refinement        'Bruker APEX5 v2023-9.2 (Bruker AXS, 2023)' 
_computing_data_reduction         'Bruker SAINT v8.40B (Bruker AXS, 2023)' 
_computing_structure_solution     'Bruker APEX5 v2023-9.2 (Bruker AXS, 2023)' 
_computing_structure_refinement   'SHELXL-2019/2 (Sheldrick, 2019)' 
_computing_molecular_graphics     'Bruker APEX5 v2023-9.2 (Bruker AXS, 2023)' 
_computing_publication_material   'CIFTAB v2014/2 (Sheldrick, 2014)' 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0487P)²+0.3852P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    diffmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2019/2 (Sheldrick 2019)' 
_refine_ls_extinction_coef        0.0032(5) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1234 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    0.02(9) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          2821 
_refine_ls_number_parameters      210 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0329 
_refine_ls_R_factor_gt            0.0317 
_refine_ls_wR_factor_ref          0.0771 
_refine_ls_wR_factor_gt           0.0765 
_refine_ls_goodness_of_fit_ref    1.078 
_refine_ls_restrained_S_all       1.078 
_refine_ls_shift/su_max           0.000 
_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 
C1 C 0.54108(10) 0.5598(3) 0.23473(13) 0.0197(4) Uani 1 1 d . . . . . 
C2 C 0.51856(11) 0.7581(3) 0.21217(14) 0.0215(4) Uani 1 1 d . . . . . 
C3 C 0.42796(11) 0.7302(3) 0.16384(14) 0.0198(4) Uani 1 1 d . . . . . 
H3A H 0.397316 0.842969 0.144301 0.024 Uiso 1 1 calc R U . . . 
H3B H 0.414186 0.637694 0.105362 0.024 Uiso 1 1 calc R U . . . 
C4 C 0.43282(10) 0.6592(2) 0.28253(14) 0.0182(4) Uani 1 1 d . . . . . 
C5 C 0.49554(11) 0.8081(3) 0.32142(15) 0.0216(4) Uani 1 1 d . . . . . 
H5A H 0.535815 0.778756 0.389058 0.026 Uiso 1 1 calc R U . . . 
H5B H 0.474212 0.931722 0.323687 0.026 Uiso 1 1 calc R U . . . 
C6 C 0.56994(12) 0.8716(3) 0.15839(17) 0.0273(4) Uani 1 1 d . . . . . 
H6A H 0.622983 0.878284 0.206305 0.041 Uiso 1 1 calc R U . . . 
H6B H 0.547844 0.993656 0.145570 0.041 Uiso 1 1 calc R U . . . 
H6C H 0.572543 0.816828 0.088182 0.041 Uiso 1 1 calc R U . . . 
C7 C 0.36485(10) 0.6350(2) 0.33337(14) 0.0184(4) Uani 1 1 d . . . . . 
C8 C 0.29055(11) 0.6960(2) 0.27925(14) 0.0197(4) Uani 1 1 d . . . . . 
H8 H 0.283254 0.750082 0.208850 0.024 Uiso 1 1 calc R U . . . 
C9 C 0.22725(11) 0.6789(2) 0.32667(14) 0.0210(4) Uani 1 1 d . . . . . 
H9 H 0.176694 0.720599 0.288977 0.025 Uiso 1 1 calc R U . . . 
C10 C 0.23797(11) 0.5998(2) 0.43046(14) 0.0211(4) Uani 1 1 d . . . . . 
C11 C 0.31245(11) 0.5423(2) 0.48693(14) 0.0214(4) Uani 1 1 d . . . . . 
H11 H 0.320065 0.491643 0.558283 0.026 Uiso 1 1 calc R U . . . 
C12 C 0.37512(11) 0.5596(3) 0.43816(14) 0.0202(4) Uani 1 1 d . . . . . 
H12 H 0.425866 0.519705 0.476279 0.024 Uiso 1 1 calc R U . . . 
C13 C 0.17159(11) 0.5790(3) 0.47808(14) 0.0227(4) Uani 1 1 d . . . . . 
C14 C 0.46324(11) 0.3096(2) 0.28887(14) 0.0197(4) Uani 1 1 d . . . . . 
H14A H 0.447199 0.285206 0.358061 0.024 Uiso 1 1 calc R U . . . 
H14B H 0.509764 0.233410 0.288776 0.024 Uiso 1 1 calc R U . . . 
C15 C 0.39676(11) 0.2528(2) 0.19338(14) 0.0186(4) Uani 1 1 d . . . . . 
C16 C 0.32563(11) 0.1925(3) 0.21166(15) 0.0219(4) Uani 1 1 d . . . . . 
H16 H 0.317516 0.194492 0.283889 0.026 Uiso 1 1 calc R U . . . 
C17 C 0.26627(11) 0.1293(3) 0.12547(15) 0.0238(4) Uani 1 1 d . . . . . 
H17 H 0.218111 0.087360 0.139020 0.029 Uiso 1 1 calc R U . . . 
C18 C 0.27755(11) 0.1275(3) 0.01947(15) 0.0240(4) Uani 1 1 d . . . . . 
H18 H 0.237567 0.082172 -0.039433 0.029 Uiso 1 1 calc R U . . . 
C19 C 0.34757(11) 0.1923(3) 0.00001(15) 0.0237(4) Uani 1 1 d . . . . . 
H19 H 0.354917 0.194162 -0.072630 0.028 Uiso 1 1 calc R U . . . 
C20 C 0.40657(11) 0.2541(3) 0.08607(15) 0.0219(4) Uani 1 1 d . . . . . 
H20 H 0.454311 0.297834 0.072079 0.026 Uiso 1 1 calc R U . . . 
N1 N 0.48617(9) 0.4988(2) 0.28790(11) 0.0184(3) Uani 1 1 d . . . . . 
N2 N 0.11735(10) 0.5644(3) 0.51455(13) 0.0301(4) Uani 1 1 d . . . . . 
O1 O 0.59340(8) 0.47265(19) 0.20891(11) 0.0262(3) Uani 1 1 d . . . . . 
  
  
_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 O1 1.224(2) . ? 
C1 N1 1.369(2) . ? 
C1 C2 1.527(3) . ? 
C2 C6 1.501(3) . ? 
C2 C5 1.562(3) . ? 
C2 C3 1.571(3) . ? 
C3 C4 1.562(2) . ? 
C4 C7 1.487(2) . ? 
C4 N1 1.501(2) . ? 
C4 C5 1.549(3) . ? 
C7 C8 1.391(3) . ? 
C7 C12 1.400(2) . ? 
C8 C9 1.382(3) . ? 
C9 C10 1.399(3) . ? 
C10 C11 1.394(3) . ? 
C10 C13 1.435(2) . ? 
C11 C12 1.382(3) . ? 
C13 N2 1.152(3) . ? 
C14 N1 1.456(2) . ? 
C14 C15 1.518(2) . ? 
C15 C16 1.391(3) . ? 
C15 C20 1.397(2) . ? 
C16 C17 1.391(3) . ? 
C17 C18 1.390(3) . ? 
C18 C19 1.390(3) . ? 
C19 C20 1.382(3) . ? 
  
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 
O1 C1 N1 127.64(17) . . ? 
O1 C1 C2 129.23(17) . . ? 
N1 C1 C2 103.08(15) . . ? 
C6 C2 C1 117.65(16) . . ? 
C6 C2 C5 124.64(17) . . ? 
C1 C2 C5 99.99(14) . . ? 
C6 C2 C3 123.83(16) . . ? 
C1 C2 C3 97.93(14) . . ? 
C5 C2 C3 85.60(13) . . ? 
C4 C3 C2 81.62(13) . . ? 
C7 C4 N1 115.98(14) . . ? 
C7 C4 C5 121.93(15) . . ? 
N1 C4 C5 99.25(14) . . ? 
C7 C4 C3 125.50(14) . . ? 
N1 C4 C3 101.60(13) . . ? 
C5 C4 C3 86.32(13) . . ? 
C4 C5 C2 82.31(13) . . ? 
C8 C7 C12 118.98(17) . . ? 
C8 C7 C4 120.09(15) . . ? 
C12 C7 C4 120.85(15) . . ? 
C9 C8 C7 120.78(16) . . ? 
C8 C9 C10 119.65(16) . . ? 
C11 C10 C9 120.25(16) . . ? 
C11 C10 C13 120.46(16) . . ? 
C9 C10 C13 119.29(16) . . ? 
C12 C11 C10 119.39(16) . . ? 
C11 C12 C7 120.92(17) . . ? 
N2 C13 C10 178.6(2) . . ? 
N1 C14 C15 114.84(14) . . ? 
C16 C15 C20 118.68(16) . . ? 
C16 C15 C14 120.44(15) . . ? 
C20 C15 C14 120.84(16) . . ? 
C17 C16 C15 120.80(17) . . ? 
C18 C17 C16 119.85(17) . . ? 
C19 C18 C17 119.72(17) . . ? 
C20 C19 C18 120.18(16) . . ? 
C19 C20 C15 120.73(17) . . ? 
C1 N1 C14 123.15(15) . . ? 
C1 N1 C4 102.64(14) . . ? 
C14 N1 C4 126.14(14) . . ? 
  
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 
O1 C1 C2 C6 -5.2(3) . . . . ? 
N1 C1 C2 C6 177.06(16) . . . . ? 
O1 C1 C2 C5 -143.30(19) . . . . ? 
N1 C1 C2 C5 39.00(16) . . . . ? 
O1 C1 C2 C3 129.80(19) . . . . ? 
N1 C1 C2 C3 -47.90(16) . . . . ? 
C6 C2 C3 C4 -165.09(19) . . . . ? 
C1 C2 C3 C4 63.80(13) . . . . ? 
C5 C2 C3 C4 -35.70(12) . . . . ? 
C2 C3 C4 C7 163.23(17) . . . . ? 
C2 C3 C4 N1 -62.70(14) . . . . ? 
C2 C3 C4 C5 35.99(13) . . . . ? 
C7 C4 C5 C2 -166.36(16) . . . . ? 
N1 C4 C5 C2 65.01(13) . . . . ? 
C3 C4 C5 C2 -36.16(12) . . . . ? 
C6 C2 C5 C4 164.69(19) . . . . ? 
C1 C2 C5 C4 -61.33(14) . . . . ? 
C3 C2 C5 C4 35.97(12) . . . . ? 
N1 C4 C7 C8 -135.80(16) . . . . ? 
C5 C4 C7 C8 103.26(19) . . . . ? 
C3 C4 C7 C8 -7.3(3) . . . . ? 
N1 C4 C7 C12 47.5(2) . . . . ? 
C5 C4 C7 C12 -73.5(2) . . . . ? 
C3 C4 C7 C12 175.96(17) . . . . ? 
C12 C7 C8 C9 -1.5(3) . . . . ? 
C4 C7 C8 C9 -178.28(16) . . . . ? 
C7 C8 C9 C10 0.2(3) . . . . ? 
C8 C9 C10 C11 1.5(3) . . . . ? 
C8 C9 C10 C13 -178.66(17) . . . . ? 
C9 C10 C11 C12 -1.8(3) . . . . ? 
C13 C10 C11 C12 178.35(17) . . . . ? 
C10 C11 C12 C7 0.4(3) . . . . ? 
C8 C7 C12 C11 1.2(3) . . . . ? 
C4 C7 C12 C11 177.95(16) . . . . ? 
N1 C14 C15 C16 -117.04(18) . . . . ? 
N1 C14 C15 C20 65.2(2) . . . . ? 
C20 C15 C16 C17 2.0(3) . . . . ? 
C14 C15 C16 C17 -175.82(17) . . . . ? 
C15 C16 C17 C18 -0.6(3) . . . . ? 
C16 C17 C18 C19 -1.3(3) . . . . ? 
C17 C18 C19 C20 1.6(3) . . . . ? 
C18 C19 C20 C15 -0.2(3) . . . . ? 
C16 C15 C20 C19 -1.6(3) . . . . ? 
C14 C15 C20 C19 176.18(17) . . . . ? 
O1 C1 N1 C14 -22.5(3) . . . . ? 
C2 C1 N1 C14 155.25(15) . . . . ? 
O1 C1 N1 C4 -172.77(17) . . . . ? 
C2 C1 N1 C4 4.98(16) . . . . ? 
C15 C14 N1 C1 -87.9(2) . . . . ? 
C15 C14 N1 C4 55.3(2) . . . . ? 
C7 C4 N1 C1 179.33(14) . . . . ? 
C5 C4 N1 C1 -48.19(15) . . . . ? 
C3 C4 N1 C1 39.92(16) . . . . ? 
C7 C4 N1 C14 30.3(2) . . . . ? 
C5 C4 N1 C14 162.75(15) . . . . ? 
C3 C4 N1 C14 -109.14(17) . . . . ? 
  
_refine_diff_density_max    0.274 
_refine_diff_density_min   -0.206 
_refine_diff_density_rms    0.075 
  
  
  
