#------------------------------------------------------------------------------
#$Date: 2022-11-28 10:25:57 +0200 (Mon, 28 Nov 2022) $
#$Revision: 279585 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106264.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106264
loop_
_publ_author_name
'Duan, Wei-Guo'
'Guo, Yi-Peng'
'Lin, Long'
'Wu, Wei-Na'
_publ_section_title
;
 Crystal structure of
 bis-(N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-3-hydroxybenzohydrazide-κ2
 O,N)copper(II) -- dimethylformamide (1/2), C40H50N8O10Cu
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              691
_journal_page_last               692
_journal_paper_doi               10.1515/ncrs-2018-0018
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C40 H50 Cu N8 O10'
_chemical_formula_weight         866.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                104.949(2)
_cell_angle_beta                 104.049(2)
_cell_angle_gamma                99.538(2)
_cell_formula_units_Z            1
_cell_length_a                   6.8237(9)
_cell_length_b                   12.9229(17)
_cell_length_c                   13.3275(18)
_cell_measurement_reflns_used    1364
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.58
_cell_measurement_theta_min      3.11
_cell_volume                     1068.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5702
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         1.658
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             455
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0584P)²+0.5285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2778
_reflns_number_total             3747
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0018_suppl.cif
_cod_data_source_block           z
_cod_database_code               8106264
_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. 
;
_shelx_estimated_absorpt_t_min   0.879
_shelx_estimated_absorpt_t_max   0.898
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 1.000000 0.500000 0.000000 0.0476(2) Uani 1 2 d S . P . .
O1 O 0.8905(5) 0.1187(2) 0.2604(2) 0.0776(8) Uani 1 1 d . . . . .
H1B H 0.849800 0.084257 0.298261 0.116 Uiso 1 1 calc R U . . .
O2 O 0.9427(4) 0.40078(18) 0.07822(18) 0.0530(6) Uani 1 1 d . . . . .
O3 O 0.1448(4) 0.7726(2) 0.2918(2) 0.0793(8) Uani 1 1 d . . . . .
O4 O 0.2821(4) 0.6268(2) 0.2928(2) 0.0646(7) Uani 1 1 d . . . . .
O5 O 0.2396(4) -0.0059(2) 0.6170(2) 0.0749(8) Uani 1 1 d . . . . .
N1 N 0.7235(4) 0.5099(2) 0.1258(2) 0.0473(7) Uani 1 1 d . . . . .
N2 N 0.8059(4) 0.5662(2) 0.0629(2) 0.0473(7) Uani 1 1 d . . . . .
N3 N 0.5015(4) 0.6659(2) 0.1603(2) 0.0487(7) Uani 1 1 d . . . . .
H3A H 0.512050 0.607331 0.178387 0.058 Uiso 1 1 calc R U . . .
N4 N 0.2398(4) 0.1341(2) 0.5467(2) 0.0556(7) Uani 1 1 d . . . . .
C1 C 0.7859(6) 0.1982(3) 0.2540(3) 0.0552(9) Uani 1 1 d . . . . .
C2 C 0.8399(5) 0.2685(3) 0.1970(3) 0.0501(8) Uani 1 1 d . . . . .
H2A H 0.944850 0.259578 0.164595 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7400(5) 0.3517(3) 0.1877(3) 0.0488(8) Uani 1 1 d . . . . .
C4 C 0.5812(7) 0.3639(3) 0.2349(3) 0.0698(11) Uani 1 1 d . . . . .
H4A H 0.512540 0.419565 0.229250 0.084 Uiso 1 1 calc R U . . .
C5 C 0.5268(8) 0.2932(3) 0.2898(4) 0.0842(14) Uani 1 1 d . . . . .
H5B H 0.418140 0.300306 0.319809 0.101 Uiso 1 1 calc R U . . .
C6 C 0.6295(7) 0.2118(3) 0.3017(3) 0.0721(11) Uani 1 1 d . . . . .
H6A H 0.593700 0.166229 0.341575 0.086 Uiso 1 1 calc R U . . .
C7 C 0.8059(5) 0.4250(3) 0.1266(2) 0.0450(7) Uani 1 1 d . . . . .
C8 C 0.7487(5) 0.6545(3) 0.0534(2) 0.0485(8) Uani 1 1 d . . . . .
H8A H 0.808270 0.689189 0.011151 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6072(5) 0.7064(3) 0.0987(3) 0.0491(8) Uani 1 1 d . . . . .
C10 C 0.5470(6) 0.8014(3) 0.0872(3) 0.0521(8) Uani 1 1 d . . . . .
C11 C 0.4008(6) 0.8178(3) 0.1430(3) 0.0547(9) Uani 1 1 d . . . . .
C12 C 0.3758(5) 0.7331(3) 0.1887(3) 0.0508(8) Uani 1 1 d . . . . .
C13 C 0.6296(6) 0.8747(3) 0.0283(3) 0.0669(10) Uani 1 1 d . . . . .
H13A H 0.562447 0.934621 0.032360 0.100 Uiso 1 1 calc R U . . .
H13B H 0.777124 0.903502 0.061368 0.100 Uiso 1 1 calc R U . . .
H13C H 0.602206 0.832719 -0.046617 0.100 Uiso 1 1 calc R U . . .
C14 C 0.2889(7) 0.9089(3) 0.1510(4) 0.0770(12) Uani 1 1 d . . . . .
H14A H 0.334958 0.956395 0.112160 0.116 Uiso 1 1 calc R U . . .
H14B H 0.141621 0.877769 0.119799 0.116 Uiso 1 1 calc R U . . .
H14C H 0.318591 0.950859 0.226060 0.116 Uiso 1 1 calc R U . . .
C15 C 0.2543(6) 0.7157(3) 0.2616(3) 0.0585(9) Uani 1 1 d . . . . .
C16 C 0.1776(6) 0.6043(4) 0.3703(3) 0.0716(11) Uani 1 1 d . . . . .
H16A H 0.027731 0.585877 0.337727 0.086 Uiso 1 1 calc R U . . .
H16B H 0.215738 0.668773 0.434099 0.086 Uiso 1 1 calc R U . . .
C17 C 0.2424(7) 0.5108(4) 0.4011(4) 0.0950(15) Uani 1 1 d . . . . .
H17A H 0.175266 0.494100 0.452480 0.142 Uiso 1 1 calc R U . . .
H17B H 0.203503 0.447365 0.337419 0.142 Uiso 1 1 calc R U . . .
H17C H 0.390742 0.529922 0.433398 0.142 Uiso 1 1 calc R U . . .
C18 C 0.1934(7) 0.2401(3) 0.5521(4) 0.0776(12) Uani 1 1 d . . . . .
H18A H 0.226998 0.263997 0.494456 0.116 Uiso 1 1 calc R U . . .
H18B H 0.047935 0.233755 0.544329 0.116 Uiso 1 1 calc R U . . .
H18C H 0.274473 0.293087 0.620992 0.116 Uiso 1 1 calc R U . . .
C19 C 0.3166(7) 0.0817(4) 0.4598(4) 0.0892(15) Uani 1 1 d . . . . .
H19A H 0.331837 0.129083 0.415859 0.134 Uiso 1 1 calc R U . . .
H19B H 0.449238 0.068471 0.490112 0.134 Uiso 1 1 calc R U . . .
H19C H 0.219781 0.012839 0.415660 0.134 Uiso 1 1 calc R U . . .
C20 C 0.2073(5) 0.0837(3) 0.6171(3) 0.0583(9) Uani 1 1 d . . . . .
H20 H 0.155428 0.119374 0.671227 0.070 Uiso 1 1 calc R U . . .
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'
Cu Cu 0.3201 1.2651 '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'
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
O2 Cu1 O2 180.0 2_765 .
O2 Cu1 N2 81.69(9) 2_765 2_765
O2 Cu1 N2 98.31(9) . 2_765
O2 Cu1 N2 98.31(9) 2_765 .
O2 Cu1 N2 81.69(9) . .
N2 Cu1 N2 180.0 2_765 .
C1 O1 H1B 109.5 . .
C7 O2 Cu1 111.13(19) . .
C15 O4 C16 116.3(3) . .
C7 N1 N2 108.5(2) . .
C8 N2 N1 118.6(3) . .
C8 N2 Cu1 127.3(2) . .
N1 N2 Cu1 114.04(18) . .
C9 N3 C12 109.1(3) . .
C9 N3 H3A 125.5 . .
C12 N3 H3A 125.5 . .
C20 N4 C19 119.8(3) . .
C20 N4 C18 121.3(3) . .
C19 N4 C18 118.9(3) . .
O1 C1 C6 122.8(3) . .
O1 C1 C2 117.9(3) . .
C6 C1 C2 119.2(3) . .
C3 C2 C1 120.9(3) . .
C3 C2 H2A 119.6 . .
C1 C2 H2A 119.6 . .
C2 C3 C4 119.5(3) . .
C2 C3 C7 118.4(3) . .
C4 C3 C7 122.1(3) . .
C5 C4 C3 119.3(4) . .
C5 C4 H4A 120.3 . .
C3 C4 H4A 120.3 . .
C4 C5 C6 121.5(4) . .
C4 C5 H5B 119.3 . .
C6 C5 H5B 119.3 . .
C5 C6 C1 119.6(3) . .
C5 C6 H6A 120.2 . .
C1 C6 H6A 120.2 . .
O2 C7 N1 124.6(3) . .
O2 C7 C3 117.1(3) . .
N1 C7 C3 118.3(3) . .
N2 C8 C9 129.2(3) . .
N2 C8 H8A 115.4 . .
C9 C8 H8A 115.4 . .
N3 C9 C10 108.1(3) . .
N3 C9 C8 123.6(3) . .
C10 C9 C8 128.3(3) . .
C9 C10 C11 107.5(3) . .
C9 C10 C13 126.1(3) . .
C11 C10 C13 126.4(3) . .
C12 C11 C10 107.2(3) . .
C12 C11 C14 126.4(4) . .
C10 C11 C14 126.4(3) . .
N3 C12 C11 108.2(3) . .
N3 C12 C15 121.9(3) . .
C11 C12 C15 129.8(3) . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O3 C15 O4 123.5(4) . .
O3 C15 C12 125.4(4) . .
O4 C15 C12 111.1(3) . .
O4 C16 C17 107.7(3) . .
O4 C16 H16A 110.2 . .
C17 C16 H16A 110.2 . .
O4 C16 H16B 110.2 . .
C17 C16 H16B 110.2 . .
H16A C16 H16B 108.5 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N4 C18 H18A 109.5 . .
N4 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N4 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N4 C19 H19A 109.5 . .
N4 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
N4 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O5 C20 N4 125.1(4) . .
O5 C20 H20 117.4 . .
N4 C20 H20 117.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.899(2) 2_765
Cu1 O2 1.899(2) .
Cu1 N2 1.932(3) 2_765
Cu1 N2 1.932(3) .
O1 C1 1.353(4) .
O1 H1B 0.8200 .
O2 C7 1.292(4) .
O3 C15 1.198(4) .
O4 C15 1.344(4) .
O4 C16 1.450(4) .
O5 C20 1.214(4) .
N1 C7 1.315(4) .
N1 N2 1.399(3) .
N2 C8 1.292(4) .
N3 C9 1.360(4) .
N3 C12 1.367(4) .
N3 H3A 0.8600 .
N4 C20 1.312(4) .
N4 C19 1.443(5) .
N4 C18 1.444(4) .
C1 C6 1.382(5) .
C1 C2 1.385(4) .
C2 C3 1.381(4) .
C2 H2A 0.9300 .
C3 C4 1.390(5) .
C3 C7 1.483(4) .
C4 C5 1.368(5) .
C4 H4A 0.9300 .
C5 C6 1.379(6) .
C5 H5B 0.9300 .
C6 H6A 0.9300 .
C8 C9 1.427(4) .
C8 H8A 0.9300 .
C9 C10 1.390(4) .
C10 C11 1.394(5) .
C10 C13 1.501(5) .
C11 C12 1.389(5) .
C11 C14 1.501(5) .
C12 C15 1.458(5) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C16 C17 1.473(6) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20 0.9300 .
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
O1 H1B O5 0.82 1.84 2.661(4) 179.4 2_656 yes
N3 H3A N1 0.86 2.19 2.728(4) 120.4 . yes
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
N2 Cu1 O2 C7 -177.6(2) 2_765 . . .
N2 Cu1 O2 C7 2.4(2) . . . .
C7 N1 N2 C8 -178.4(3) . . . .
C7 N1 N2 Cu1 1.0(3) . . . .
O1 C1 C2 C3 -179.7(3) . . . .
C6 C1 C2 C3 0.2(5) . . . .
C1 C2 C3 C4 -0.9(5) . . . .
C1 C2 C3 C7 179.5(3) . . . .
C2 C3 C4 C5 0.0(6) . . . .
C7 C3 C4 C5 179.6(4) . . . .
C3 C4 C5 C6 1.6(7) . . . .
C4 C5 C6 C1 -2.4(7) . . . .
O1 C1 C6 C5 -178.7(4) . . . .
C2 C1 C6 C5 1.4(6) . . . .
Cu1 O2 C7 N1 -2.8(4) . . . .
Cu1 O2 C7 C3 177.8(2) . . . .
N2 N1 C7 O2 1.2(4) . . . .
N2 N1 C7 C3 -179.4(3) . . . .
C2 C3 C7 O2 5.3(5) . . . .
C4 C3 C7 O2 -174.3(3) . . . .
C2 C3 C7 N1 -174.2(3) . . . .
C4 C3 C7 N1 6.2(5) . . . .
N1 N2 C8 C9 -0.3(5) . . . .
Cu1 N2 C8 C9 -179.7(3) . . . .
C12 N3 C9 C10 -0.2(4) . . . .
C12 N3 C9 C8 -178.6(3) . . . .
N2 C8 C9 N3 -1.8(6) . . . .
N2 C8 C9 C10 -179.7(3) . . . .
N3 C9 C10 C11 -0.3(4) . . . .
C8 C9 C10 C11 177.9(3) . . . .
N3 C9 C10 C13 178.1(3) . . . .
C8 C9 C10 C13 -3.7(6) . . . .
C9 C10 C11 C12 0.7(4) . . . .
C13 C10 C11 C12 -177.7(3) . . . .
C9 C10 C11 C14 -178.6(3) . . . .
C13 C10 C11 C14 3.1(6) . . . .
C9 N3 C12 C11 0.7(4) . . . .
C9 N3 C12 C15 -175.4(3) . . . .
C10 C11 C12 N3 -0.8(4) . . . .
C14 C11 C12 N3 178.4(3) . . . .
C10 C11 C12 C15 174.8(3) . . . .
C14 C11 C12 C15 -6.0(6) . . . .
C16 O4 C15 O3 -2.5(5) . . . .
C16 O4 C15 C12 176.8(3) . . . .
N3 C12 C15 O3 178.3(3) . . . .
C11 C12 C15 O3 3.2(6) . . . .
N3 C12 C15 O4 -1.0(5) . . . .
C11 C12 C15 O4 -176.1(3) . . . .
C15 O4 C16 C17 -175.0(3) . . . .
C19 N4 C20 O5 1.1(6) . . . .
C18 N4 C20 O5 179.0(4) . . . .
