 
data_56
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C22 H24 Cu N6 O6' 
_chemical_formula_sum 
 'C22 H24 Cu N6 O6' 
_chemical_formula_weight          532.01 
  
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       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
  
_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+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    11.2026(2) 
_cell_length_b                    7.77280(10) 
_cell_length_c                    13.5209(2) 
_cell_angle_alpha                 90 
_cell_angle_beta                  103.0985(18) 
_cell_angle_gamma                 90 
_cell_volume                      1146.71(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     7201 
_cell_measurement_theta_min       4.6140 
_cell_measurement_theta_max       73.6200 
  
_exptl_crystal_description        blocks 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.541 
_exptl_crystal_F_000              550 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.176 
_exptl_crystal_size_mid           0.055 
_exptl_crystal_size_min           0.045 
_exptl_absorpt_coefficient_mu     1.801 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.763 
_exptl_absorpt_correction_T_max   0.928 
_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             16106 
_diffrn_reflns_av_unetI/netI      0.0245 
_diffrn_reflns_av_R_equivalents   0.0455 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          4.640 
_diffrn_reflns_theta_max          73.817 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.994 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    0.994 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   0.994 
_diffrn_reflns_point_group_measured_fraction_full  1.000 
_reflns_number_total              2304 
_reflns_number_gt                 1995 
_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)+(0.0495P)²+0.6973P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          2304 
_refine_ls_number_parameters      165 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0392 
_refine_ls_R_factor_gt            0.0325 
_refine_ls_wR_factor_ref          0.0909 
_refine_ls_wR_factor_gt           0.0853 
_refine_ls_goodness_of_fit_ref    1.043 
_refine_ls_restrained_S_all       1.042 
_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 
Cu1 Cu 0.500000 0.500000 0.000000 0.01850(13) Uani 1 2 d S . P . . 
N1 N 0.30830(16) 1.0329(2) 0.12538(14) 0.0273(4) Uani 1 1 d . . . . . 
N2 N 0.40098(15) 0.98698(19) 0.07851(12) 0.0219(3) Uani 1 1 d D . . . . 
H2 H 0.4420(5) 1.0728(5) 0.0563(5) 0.044(8) Uiso 1 1 d D . . . . 
C3 C 0.39834(17) 0.8173(2) 0.05313(13) 0.0190(4) Uani 1 1 d . . . . . 
O3 O 0.47739(13) 0.75182(16) 0.00731(10) 0.0226(3) Uani 1 1 d . . . . . 
C4 C 0.29790(17) 0.7483(2) 0.08633(14) 0.0218(4) Uani 1 1 d . . . . . 
C5 C 0.24883(19) 0.8891(3) 0.13045(15) 0.0257(4) Uani 1 1 d . . . . . 
H5A H 0.180205 0.880269 0.160506 0.031 Uiso 1 1 calc R U . . . 
C6 C 0.25397(17) 0.5744(2) 0.07076(13) 0.0206(4) Uani 1 1 d . . . . . 
O6 O 0.30004(13) 0.46088(17) 0.02874(10) 0.0239(3) Uani 1 1 d . . . . . 
O7 O 0.15275(12) 0.54674(18) 0.10667(10) 0.0246(3) Uani 1 1 d . . . . . 
C8 C 0.1063(2) 0.3715(3) 0.09837(17) 0.0286(4) Uani 1 1 d . . . . . 
H8A H 0.171137 0.290979 0.132499 0.034 Uiso 1 1 calc R U . . . 
H8B H 0.079958 0.337932 0.026072 0.034 Uiso 1 1 calc R U . . . 
C9 C -0.0007(2) 0.3650(3) 0.14828(17) 0.0330(5) Uani 1 1 d . . . . . 
H9A H -0.065423 0.442008 0.112429 0.049 Uiso 1 1 calc R U . . . 
H9B H 0.025902 0.401580 0.219230 0.049 Uiso 1 1 calc R U . . . 
H9C H -0.032212 0.247064 0.145712 0.049 Uiso 1 1 calc R U . . . 
N11 N 0.56637(15) 0.48246(19) 0.15244(12) 0.0211(3) Uani 1 1 d . . . . . 
C12 C 0.51616(18) 0.3760(2) 0.20996(15) 0.0229(4) Uani 1 1 d . . . . . 
H12A H 0.443615 0.315461 0.179067 0.028 Uiso 1 1 calc R U . . . 
C13 C 0.5657(2) 0.3509(3) 0.31224(16) 0.0280(4) Uani 1 1 d . . . . . 
H13A H 0.527403 0.275150 0.350746 0.034 Uiso 1 1 calc R U . . . 
C14 C 0.6720(2) 0.4379(3) 0.35782(15) 0.0316(5) Uani 1 1 d . . . . . 
H14A H 0.707847 0.422960 0.427995 0.038 Uiso 1 1 calc R U . . . 
C15 C 0.7246(2) 0.5466(3) 0.29918(17) 0.0342(5) Uani 1 1 d . . . . . 
H15A H 0.797551 0.607642 0.328222 0.041 Uiso 1 1 calc R U . . . 
C16 C 0.66917(19) 0.5652(3) 0.19713(16) 0.0286(4) Uani 1 1 d . . . . . 
H16A H 0.705882 0.640192 0.157109 0.034 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 
Cu1 O3 1.9790(13) . ? 
Cu1 O3 1.9790(13) 3_665 ? 
Cu1 N11 2.0310(16) . ? 
Cu1 N11 2.0311(16) 3_665 ? 
Cu1 O6 2.3783(13) . ? 
Cu1 O6 2.3783(13) 3_665 ? 
N1 C5 1.311(3) . ? 
N1 N2 1.380(2) . ? 
N2 C3 1.361(2) . ? 
C3 O3 1.295(2) . ? 
C3 C4 1.409(3) . ? 
C4 C5 1.416(3) . ? 
C4 C6 1.438(3) . ? 
C6 O6 1.225(2) . ? 
C6 O7 1.348(2) . ? 
O7 C8 1.453(2) . ? 
C8 C9 1.504(3) . ? 
N11 C16 1.338(3) . ? 
N11 C12 1.343(2) . ? 
C12 C13 1.382(3) . ? 
C13 C14 1.387(3) . ? 
C14 C15 1.379(3) . ? 
C15 C16 1.386(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 
O3 Cu1 O3 180.0 . 3_665 ? 
O3 Cu1 N11 92.14(6) . . ? 
O3 Cu1 N11 87.86(6) 3_665 . ? 
O3 Cu1 N11 87.86(6) . 3_665 ? 
O3 Cu1 N11 92.14(6) 3_665 3_665 ? 
N11 Cu1 N11 180.0 . 3_665 ? 
O3 Cu1 O6 88.99(5) . . ? 
O3 Cu1 O6 91.01(5) 3_665 . ? 
N11 Cu1 O6 88.13(6) . . ? 
N11 Cu1 O6 91.87(6) 3_665 . ? 
O3 Cu1 O6 91.01(5) . 3_665 ? 
O3 Cu1 O6 88.99(5) 3_665 3_665 ? 
N11 Cu1 O6 91.87(6) . 3_665 ? 
N11 Cu1 O6 88.13(6) 3_665 3_665 ? 
O6 Cu1 O6 180.0 . 3_665 ? 
C5 N1 N2 104.34(15) . . ? 
C3 N2 N1 112.99(15) . . ? 
O3 C3 N2 121.57(16) . . ? 
O3 C3 C4 133.25(17) . . ? 
N2 C3 C4 105.18(15) . . ? 
C3 O3 Cu1 121.47(11) . . ? 
C3 C4 C5 104.74(16) . . ? 
C3 C4 C6 125.67(17) . . ? 
C5 C4 C6 129.48(18) . . ? 
N1 C5 C4 112.74(17) . . ? 
O6 C6 O7 121.98(17) . . ? 
O6 C6 C4 125.37(17) . . ? 
O7 C6 C4 112.64(16) . . ? 
C6 O6 Cu1 119.69(12) . . ? 
C6 O7 C8 115.92(15) . . ? 
O7 C8 C9 107.75(16) . . ? 
C16 N11 C12 117.73(17) . . ? 
C16 N11 Cu1 120.38(13) . . ? 
C12 N11 Cu1 121.60(13) . . ? 
N11 C12 C13 122.73(18) . . ? 
C12 C13 C14 119.02(19) . . ? 
C15 C14 C13 118.63(19) . . ? 
C14 C15 C16 118.9(2) . . ? 
N11 C16 C15 123.00(19) . . ? 
  
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 
 _geom_hbond_publ_flag 
N2 H2 O3  0.9000(1) 1.940(2) 2.836(2) 173.4(7) 3_675 yes 
  
_refine_diff_density_max    0.315 
_refine_diff_density_min   -0.387 
_refine_diff_density_rms    0.064 
  
  
  
#===END

