 
data_54
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C24 H22 Cu N4 O6' 
_chemical_formula_sum 
 'C24 H22 Cu N4 O6' 
_chemical_formula_weight          525.99 
  
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' 
 'Cu'  'Cu'  -1.9646   0.5888 
 '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       triclinic 
_space_group_IT_number            2 
_space_group_name_H-M_alt         'P -1' 
_space_group_name_Hall            '-P 1' 
  
_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' 
  
_cell_length_a                    7.3453(5) 
_cell_length_b                    12.1217(8) 
_cell_length_c                    14.3414(12) 
_cell_angle_alpha                 110.961(7) 
_cell_angle_beta                  99.156(6) 
_cell_angle_gamma                 90.661(5) 
_cell_volume                      1173.99(16) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     2307 
_cell_measurement_theta_min       6.1040 
_cell_measurement_theta_max       73.4840 
  
_exptl_crystal_description        tablets 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.488 
_exptl_crystal_F_000              542 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.346 
_exptl_crystal_size_mid           0.184 
_exptl_crystal_size_min           0.040 
_exptl_absorpt_coefficient_mu     1.731 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.685 
_exptl_absorpt_correction_T_max   0.935 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'Enhance Ultra (Cu) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur PX Ultra A' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  10.4115 
_diffrn_reflns_number             6939 
_diffrn_reflns_av_unetI/netI      0.0579 
_diffrn_reflns_av_R_equivalents   0.0360 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          3.916 
_diffrn_reflns_theta_max          73.719 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.940 
_diffrn_measured_fraction_theta_full  0.983 
_diffrn_reflns_Laue_measured_fraction_max    0.940 
_diffrn_reflns_Laue_measured_fraction_full   0.983 
_diffrn_reflns_point_group_measured_fraction_max   0.940 
_diffrn_reflns_point_group_measured_fraction_full  0.983 
_reflns_number_total              4468 
_reflns_number_gt                 3168 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_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        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_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)+(0.0478P)²+0.3538P] 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_number_reflns          4468 
_refine_ls_number_parameters      321 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0706 
_refine_ls_R_factor_gt            0.0433 
_refine_ls_wR_factor_ref          0.1213 
_refine_ls_wR_factor_gt           0.0997 
_refine_ls_goodness_of_fit_ref    1.055 
_refine_ls_restrained_S_all       1.055 
_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 
Cu1A Cu 0.500000 0.000000 0.500000 0.02947(18) Uani 1 2 d S . P . . 
N1A N 0.2919(4) 0.3961(2) 0.5030(2) 0.0334(6) Uani 1 1 d . . . . . 
N2A N 0.3120(4) 0.2844(2) 0.4315(2) 0.0278(6) Uani 1 1 d . . . . . 
C3A C 0.3621(4) 0.2048(3) 0.4779(2) 0.0264(7) Uani 1 1 d . . . . . 
O3A O 0.3887(3) 0.09726(18) 0.42897(17) 0.0314(5) Uani 1 1 d . . . . . 
C4A C 0.3758(4) 0.2682(3) 0.5819(2) 0.0282(7) Uani 1 1 d . . . . . 
C5A C 0.3298(5) 0.3838(3) 0.5908(3) 0.0331(7) Uani 1 1 d . . . . . 
H5A H 0.326687 0.445870 0.653707 0.040 Uiso 1 1 calc R U . . . 
C6A C 0.3117(4) 0.2713(3) 0.3296(2) 0.0286(7) Uani 1 1 d . . . . . 
C7A C 0.3315(5) 0.3720(3) 0.3052(3) 0.0352(8) Uani 1 1 d . . . . . 
H7A H 0.342352 0.448627 0.356588 0.042 Uiso 1 1 calc R U . . . 
C8A C 0.3351(5) 0.3594(4) 0.2060(3) 0.0443(9) Uani 1 1 d . . . . . 
H8A H 0.349853 0.427969 0.189631 0.053 Uiso 1 1 calc R U . . . 
C9A C 0.3177(5) 0.2489(4) 0.1302(3) 0.0449(9) Uani 1 1 d . . . . . 
H9A H 0.320029 0.241055 0.062091 0.054 Uiso 1 1 calc R U . . . 
C10A C 0.2969(5) 0.1501(3) 0.1549(3) 0.0436(9) Uani 1 1 d . . . . . 
H10A H 0.285253 0.073681 0.103089 0.052 Uiso 1 1 calc R U . . . 
C11A C 0.2926(5) 0.1601(3) 0.2533(3) 0.0385(8) Uani 1 1 d . . . . . 
H11A H 0.276574 0.091058 0.268801 0.046 Uiso 1 1 calc R U . . . 
C12A C 0.4298(4) 0.2180(3) 0.6569(2) 0.0290(7) Uani 1 1 d . . . . . 
O12A O 0.4738(3) 0.11389(18) 0.63731(17) 0.0304(5) Uani 1 1 d . . . . . 
O13A O 0.4348(3) 0.29072(19) 0.75203(17) 0.0333(5) Uani 1 1 d . . . . . 
C14A C 0.4995(5) 0.2446(3) 0.8305(3) 0.0360(8) Uani 1 1 d . . . . . 
H14A H 0.618094 0.208160 0.819835 0.043 Uiso 1 1 calc R U . . . 
H14B H 0.407809 0.183699 0.829896 0.043 Uiso 1 1 calc R U . . . 
C15A C 0.5249(6) 0.3474(3) 0.9294(3) 0.0465(9) Uani 1 1 d . . . . . 
H15A H 0.568564 0.320034 0.985041 0.070 Uiso 1 1 calc R U . . . 
H15B H 0.406632 0.382724 0.938861 0.070 Uiso 1 1 calc R U . . . 
H15C H 0.616091 0.406847 0.929000 0.070 Uiso 1 1 calc R U . . . 
Cu1B Cu 1.000000 0.500000 0.500000 0.02896(18) Uani 1 2 d S . P . . 
N1B N 0.8025(4) 0.1035(2) 0.5046(2) 0.0362(7) Uani 1 1 d . . . . . 
N2B N 0.8542(4) 0.2186(2) 0.5742(2) 0.0307(6) Uani 1 1 d . . . . . 
C3B C 0.8751(4) 0.2964(3) 0.5263(2) 0.0264(7) Uani 1 1 d . . . . . 
O3B O 0.9192(3) 0.40693(18) 0.57266(17) 0.0311(5) Uani 1 1 d . . . . . 
C4B C 0.8376(4) 0.2288(3) 0.4223(2) 0.0290(7) Uani 1 1 d . . . . . 
C5B C 0.7932(5) 0.1118(3) 0.4155(3) 0.0354(8) Uani 1 1 d . . . . . 
H5B H 0.760382 0.046639 0.353175 0.042 Uiso 1 1 calc R U . . . 
C6B C 0.9066(4) 0.2372(3) 0.6785(2) 0.0300(7) Uani 1 1 d . . . . . 
C7B C 0.9366(5) 0.1395(3) 0.7071(3) 0.0422(9) Uani 1 1 d . . . . . 
H7B H 0.920805 0.061639 0.657298 0.051 Uiso 1 1 calc R U . . . 
C8B C 0.9895(5) 0.1569(4) 0.8085(3) 0.0506(10) Uani 1 1 d . . . . . 
H8B H 1.009997 0.090427 0.828150 0.061 Uiso 1 1 calc R U . . . 
C9B C 1.0130(5) 0.2693(4) 0.8817(3) 0.0508(10) Uani 1 1 d . . . . . 
H9B H 1.048429 0.280285 0.951229 0.061 Uiso 1 1 calc R U . . . 
C10B C 0.9843(6) 0.3660(4) 0.8527(3) 0.0496(10) Uani 1 1 d . . . . . 
H10B H 1.003210 0.443725 0.902729 0.060 Uiso 1 1 calc R U . . . 
C11B C 0.9285(5) 0.3508(3) 0.7518(3) 0.0397(8) Uani 1 1 d . . . . . 
H11B H 0.905334 0.417424 0.732785 0.048 Uiso 1 1 calc R U . . . 
C12B C 0.8470(4) 0.2755(3) 0.3456(2) 0.0278(7) Uani 1 1 d . . . . . 
O12B O 0.8936(3) 0.38145(18) 0.36258(17) 0.0311(5) Uani 1 1 d . . . . . 
O13B O 0.8036(3) 0.19882(19) 0.25096(17) 0.0345(5) Uani 1 1 d . . . . . 
C14B C 0.8214(5) 0.2426(3) 0.1707(3) 0.0362(8) Uani 1 1 d . . . . . 
H14C H 0.947203 0.280192 0.181559 0.043 Uiso 1 1 calc R U . . . 
H14D H 0.730615 0.301972 0.169234 0.043 Uiso 1 1 calc R U . . . 
C15B C 0.7850(6) 0.1368(3) 0.0725(3) 0.0477(10) Uani 1 1 d . . . . . 
H15D H 0.799246 0.162074 0.016119 0.071 Uiso 1 1 calc R U . . . 
H15E H 0.658889 0.101927 0.061739 0.071 Uiso 1 1 calc R U . . . 
H15F H 0.873436 0.077830 0.075769 0.071 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 
Cu1A O3A 1.927(2) . ? 
Cu1A O3A 1.927(2) 2_656 ? 
Cu1A O12A 2.001(2) . ? 
Cu1A O12A 2.001(2) 2_656 ? 
Cu1A N1B 2.519(3) 2_656 ? 
Cu1A N1B 2.519(3) . ? 
N1A C5A 1.307(4) . ? 
N1A N2A 1.402(4) . ? 
N2A C3A 1.379(4) . ? 
N2A C6A 1.411(4) . ? 
C3A O3A 1.275(4) . ? 
C3A C4A 1.398(4) . ? 
C4A C5A 1.410(4) . ? 
C4A C12A 1.423(4) . ? 
C6A C11A 1.389(5) . ? 
C6A C7A 1.396(4) . ? 
C7A C8A 1.381(5) . ? 
C8A C9A 1.379(6) . ? 
C9A C10A 1.379(5) . ? 
C10A C11A 1.378(5) . ? 
C12A O12A 1.249(4) . ? 
C12A O13A 1.328(4) . ? 
O13A C14A 1.447(4) . ? 
C14A C15A 1.499(5) . ? 
Cu1B O3B 1.932(2) 2_766 ? 
Cu1B O3B 1.932(2) . ? 
Cu1B O12B 2.004(2) . ? 
Cu1B O12B 2.004(2) 2_766 ? 
Cu1B N1A 2.501(3) 1_655 ? 
Cu1B N1A 2.501(3) 2_666 ? 
N1B C5B 1.309(4) . ? 
N1B N2B 1.400(4) . ? 
N2B C3B 1.371(4) . ? 
N2B C6B 1.418(4) . ? 
C3B O3B 1.275(4) . ? 
C3B C4B 1.401(4) . ? 
C4B C12B 1.416(4) . ? 
C4B C5B 1.417(4) . ? 
C6B C11B 1.390(5) . ? 
C6B C7B 1.394(5) . ? 
C7B C8B 1.382(5) . ? 
C8B C9B 1.379(6) . ? 
C9B C10B 1.384(6) . ? 
C10B C11B 1.384(5) . ? 
C12B O12B 1.251(4) . ? 
C12B O13B 1.327(4) . ? 
O13B C14B 1.452(4) . ? 
C14B C15B 1.510(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 
O3A Cu1A O3A 180.0 . 2_656 ? 
O3A Cu1A O12A 94.59(9) . . ? 
O3A Cu1A O12A 85.41(9) 2_656 . ? 
O3A Cu1A O12A 85.41(9) . 2_656 ? 
O3A Cu1A O12A 94.59(9) 2_656 2_656 ? 
O12A Cu1A O12A 180.0 . 2_656 ? 
O3A Cu1A N1B 94.44(10) . 2_656 ? 
O3A Cu1A N1B 85.56(10) 2_656 2_656 ? 
O12A Cu1A N1B 87.63(9) . 2_656 ? 
O12A Cu1A N1B 92.37(9) 2_656 2_656 ? 
O3A Cu1A N1B 85.56(10) . . ? 
O3A Cu1A N1B 94.44(10) 2_656 . ? 
O12A Cu1A N1B 92.37(9) . . ? 
O12A Cu1A N1B 87.63(9) 2_656 . ? 
N1B Cu1A N1B 180.0 2_656 . ? 
C5A N1A N2A 104.9(3) . . ? 
C3A N2A N1A 111.2(3) . . ? 
C3A N2A C6A 128.1(3) . . ? 
N1A N2A C6A 119.7(2) . . ? 
O3A C3A N2A 123.0(3) . . ? 
O3A C3A C4A 131.3(3) . . ? 
N2A C3A C4A 105.7(3) . . ? 
C3A O3A Cu1A 120.2(2) . . ? 
C3A C4A C5A 105.6(3) . . ? 
C3A C4A C12A 123.2(3) . . ? 
C5A C4A C12A 131.2(3) . . ? 
N1A C5A C4A 112.7(3) . . ? 
C11A C6A C7A 119.4(3) . . ? 
C11A C6A N2A 121.2(3) . . ? 
C7A C6A N2A 119.5(3) . . ? 
C8A C7A C6A 119.6(3) . . ? 
C9A C8A C7A 121.0(3) . . ? 
C10A C9A C8A 119.0(4) . . ? 
C11A C10A C9A 121.2(4) . . ? 
C10A C11A C6A 119.8(3) . . ? 
O12A C12A O13A 120.9(3) . . ? 
O12A C12A C4A 123.8(3) . . ? 
O13A C12A C4A 115.3(3) . . ? 
C12A O12A Cu1A 125.4(2) . . ? 
C12A O13A C14A 116.7(2) . . ? 
O13A C14A C15A 106.7(3) . . ? 
O3B Cu1B O3B 180.0 2_766 . ? 
O3B Cu1B O12B 85.49(9) 2_766 . ? 
O3B Cu1B O12B 94.51(9) . . ? 
O3B Cu1B O12B 94.51(9) 2_766 2_766 ? 
O3B Cu1B O12B 85.49(9) . 2_766 ? 
O12B Cu1B O12B 180.0 . 2_766 ? 
O3B Cu1B N1A 85.88(10) 2_766 2_666 ? 
O3B Cu1B N1A 94.12(10) . 2_666 ? 
O12B Cu1B N1A 88.69(9) . 2_666 ? 
O12B Cu1B N1A 91.31(9) 2_766 2_666 ? 
O3B Cu1B N1A 94.12(10) 2_766 1_655 ? 
O3B Cu1B N1A 85.88(10) . 1_655 ? 
O12B Cu1B N1A 91.31(9) . 1_655 ? 
O12B Cu1B N1A 88.69(9) 2_766 1_655 ? 
N1A Cu1B N1A 180.0 2_666 1_655 ? 
C5B N1B N2B 104.9(3) . . ? 
C5B N1B Cu1A 106.1(2) . . ? 
N2B N1B Cu1A 120.3(2) . . ? 
C3B N2B N1B 111.6(3) . . ? 
C3B N2B C6B 128.3(3) . . ? 
N1B N2B C6B 119.2(3) . . ? 
O3B C3B N2B 123.9(3) . . ? 
O3B C3B C4B 130.3(3) . . ? 
N2B C3B C4B 105.8(3) . . ? 
C3B O3B Cu1B 119.7(2) . . ? 
C3B C4B C12B 124.0(3) . . ? 
C3B C4B C5B 105.3(3) . . ? 
C12B C4B C5B 130.7(3) . . ? 
N1B C5B C4B 112.5(3) . . ? 
C11B C6B C7B 120.0(3) . . ? 
C11B C6B N2B 120.9(3) . . ? 
C7B C6B N2B 119.0(3) . . ? 
C8B C7B C6B 119.4(4) . . ? 
C9B C8B C7B 121.0(4) . . ? 
C8B C9B C10B 119.4(4) . . ? 
C11B C10B C9B 120.7(4) . . ? 
C10B C11B C6B 119.5(3) . . ? 
O12B C12B O13B 120.1(3) . . ? 
O12B C12B C4B 124.1(3) . . ? 
O13B C12B C4B 115.8(3) . . ? 
C12B O12B Cu1B 124.1(2) . . ? 
C12B O13B C14B 117.1(2) . . ? 
O13B C14B C15B 106.7(3) . . ? 
  
_refine_diff_density_max    0.455 
_refine_diff_density_min   -0.368 
_refine_diff_density_rms    0.070 
  
  
  
#===END

