#------------------------------------------------------------------------------
#$Date: 2022-11-17 12:14:49 +0200 (Thu, 17 Nov 2022) $
#$Revision: 279359 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106139.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_8106139
loop_
_publ_author_name
'Han, Xue-Feng'
'Yang, Qing-Wen'
'Yang, Miao'
'Wu, Wei-Na'
_publ_section_title
;
 Crystal structure of
 {5,5′-((propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4
 N,N′,N′′,N′′′}zinc(II),
 C23H30N4O4Cu
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              319
_journal_page_last               320
_journal_paper_doi               10.1515/ncrs-2017-0315
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C23 H30 Cu N4 O4'
_chemical_formula_weight         490.05
_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                95.766(7)
_cell_angle_beta                 98.007(7)
_cell_angle_gamma                101.595(13)
_cell_formula_units_Z            2
_cell_length_a                   7.746(6)
_cell_length_b                   12.344(9)
_cell_length_c                   12.655(9)
_cell_measurement_temperature    296(2)
_cell_volume                     1163.4(15)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0657
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12470
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         1.639
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5310
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0801P)²+0.3106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1616
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4099
_reflns_number_total             5310
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0315_suppl.cif
_cod_data_source_block           z
_cod_database_code               8106139
_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   0.829
_shelx_estimated_absorpt_t_max   0.868
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 0.52283(5) 0.51864(3) 0.26879(3) 0.03900(16) Uani 1 1 d . . . . .
O1 O -0.0819(4) 0.1584(2) 0.0234(2) 0.0561(7) Uani 1 1 d . . . . .
O2 O -0.0996(5) 0.2388(3) -0.1273(3) 0.0801(10) Uani 1 1 d . . . . .
O3 O 0.7828(7) 0.0999(3) 0.3772(3) 0.1045(14) Uani 1 1 d . . . . .
O4 O 0.7967(5) 0.1575(3) 0.5516(3) 0.0808(10) Uani 1 1 d D . . . .
N1 N 0.3297(4) 0.4329(2) 0.1560(2) 0.0398(6) Uani 1 1 d . . . . .
N2 N 0.5055(4) 0.6401(2) 0.1799(3) 0.0480(7) Uani 1 1 d . . . . .
N3 N 0.6472(4) 0.6234(2) 0.3979(2) 0.0437(7) Uani 1 1 d . . . . .
N4 N 0.6320(4) 0.4110(2) 0.3439(2) 0.0398(6) Uani 1 1 d . . . . .
C1 C -0.2559(7) -0.0151(4) 0.0457(4) 0.0745(13) Uani 1 1 d . . . . .
H1B H -0.346541 -0.078398 0.010909 0.112 Uiso 1 1 calc R U . . .
H1C H -0.295498 0.019143 0.106708 0.112 Uiso 1 1 calc R U . . .
H1A H -0.148002 -0.039018 0.069256 0.112 Uiso 1 1 calc R U . . .
C2 C -0.2213(6) 0.0666(4) -0.0311(4) 0.0703(12) Uani 1 1 d . . . . .
H2A H -0.184334 0.032270 -0.094075 0.084 Uiso 1 1 calc R U . . .
H2B H -0.328770 0.092661 -0.054224 0.084 Uiso 1 1 calc R U . . .
C3 C -0.0289(5) 0.2417(3) -0.0355(3) 0.0476(8) Uani 1 1 d . . . . .
C4 C 0.1158(4) 0.3298(3) 0.0242(3) 0.0390(7) Uani 1 1 d . . . . .
C5 C 0.1845(4) 0.4302(3) -0.0156(3) 0.0407(7) Uani 1 1 d . . . . .
C6 C 0.3126(4) 0.4915(3) 0.0675(3) 0.0375(7) Uani 1 1 d . . . . .
C7 C 0.2081(4) 0.3355(3) 0.1305(3) 0.0381(7) Uani 1 1 d . . . . .
C8 C 0.1285(5) 0.4666(3) -0.1220(3) 0.0493(8) Uani 1 1 d . . . . .
H8A H 0.155598 0.417937 -0.178534 0.074 Uiso 1 1 calc R U . . .
H8B H 0.191704 0.541634 -0.123305 0.074 Uiso 1 1 calc R U . . .
H8C H 0.002358 0.463403 -0.132527 0.074 Uiso 1 1 calc R U . . .
C9 C 0.1787(6) 0.2566(3) 0.2115(3) 0.0525(9) Uani 1 1 d . . . . .
H9A H 0.269417 0.281107 0.273996 0.079 Uiso 1 1 calc R U . . .
H9B H 0.184540 0.183255 0.180928 0.079 Uiso 1 1 calc R U . . .
H9C H 0.063336 0.254550 0.231828 0.079 Uiso 1 1 calc R U . . .
C10 C 0.4089(5) 0.6052(3) 0.0865(3) 0.0444(8) Uani 1 1 d . . . . .
H10 H 0.402254 0.652080 0.033722 0.053 Uiso 1 1 calc R U . . .
C11 C 0.5866(7) 0.7590(3) 0.2090(3) 0.0729(13) Uani 1 1 d D . . . .
H11A H 0.491730 0.798797 0.215127 0.087 Uiso 0.721(11) 1 calc R U P A 1
H11B H 0.645486 0.784742 0.150467 0.087 Uiso 0.721(11) 1 calc R U P A 1
H11C H 0.522523 0.801686 0.163575 0.087 Uiso 0.279(11) 1 calc R U P A 2
H11D H 0.709387 0.772895 0.196546 0.087 Uiso 0.279(11) 1 calc R U P A 2
C12 C 0.7173(8) 0.7896(4) 0.3096(4) 0.063(2) Uani 0.721(11) 1 d D . P A 1
H12A H 0.746445 0.870375 0.324823 0.076 Uiso 0.721(11) 1 calc R U P A 1
H12B H 0.825535 0.766775 0.295590 0.076 Uiso 0.721(11) 1 calc R U P A 1
C12A C 0.5823(18) 0.7960(9) 0.3232(5) 0.055(5) Uani 0.279(11) 1 d D . P A 2
H12C H 0.633526 0.875524 0.336605 0.066 Uiso 0.279(11) 1 calc R U P A 2
H12D H 0.457603 0.786575 0.331264 0.066 Uiso 0.279(11) 1 calc R U P A 2
C13 C 0.6702(6) 0.7450(3) 0.4103(3) 0.0617(11) Uani 1 1 d D . . . .
H13A H 0.764287 0.778241 0.470452 0.074 Uiso 0.721(11) 1 calc R U P A 1
H13B H 0.560500 0.764841 0.425765 0.074 Uiso 0.721(11) 1 calc R U P A 1
H13C H 0.797300 0.777206 0.420707 0.074 Uiso 0.279(11) 1 calc R U P A 2
H13D H 0.628002 0.767291 0.476085 0.074 Uiso 0.279(11) 1 calc R U P A 2
C14 C 0.7157(5) 0.5735(3) 0.4733(3) 0.0437(8) Uani 1 1 d . . . . .
H14 H 0.769580 0.612310 0.540455 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7055(4) 0.4567(3) 0.4495(3) 0.0396(7) Uani 1 1 d . . . . .
C16 C 0.7705(5) 0.3801(3) 0.5073(3) 0.0433(8) Uani 1 1 d . . . . .
C17 C 0.7412(5) 0.2822(3) 0.4313(3) 0.0455(8) Uani 1 1 d . . . . .
C18 C 0.6567(5) 0.3058(3) 0.3317(3) 0.0418(7) Uani 1 1 d . . . . .
C19 C 0.8600(6) 0.4010(4) 0.6228(3) 0.0566(10) Uani 1 1 d . . . . .
H19A H 0.976269 0.384026 0.627497 0.085 Uiso 1 1 calc R U . . .
H19B H 0.789333 0.354458 0.664364 0.085 Uiso 1 1 calc R U . . .
H19C H 0.871817 0.477952 0.650375 0.085 Uiso 1 1 calc R U . . .
C20 C 0.6122(6) 0.2342(3) 0.2252(3) 0.0580(10) Uani 1 1 d . . . . .
H20A H 0.541423 0.267680 0.174982 0.087 Uiso 1 1 calc R U . . .
H20B H 0.546081 0.161697 0.233051 0.087 Uiso 1 1 calc R U . . .
H20C H 0.720488 0.227201 0.199003 0.087 Uiso 1 1 calc R U . . .
C21 C 0.7753(6) 0.1715(4) 0.4471(4) 0.0628(11) Uani 1 1 d . . . . .
C22 C 0.8274(9) 0.0514(4) 0.5749(6) 0.111(2) Uani 1 1 d D . . . .
H22A H 0.952239 0.058600 0.604320 0.134 Uiso 1 1 calc R U . . .
H22B H 0.799019 -0.000951 0.509240 0.134 Uiso 1 1 calc R U . . .
C23 C 0.7161(16) 0.0102(6) 0.6521(8) 0.189(5) Uani 1 1 d D . . . .
H23A H 0.592478 -0.000566 0.621179 0.283 Uiso 1 1 calc R U . . .
H23B H 0.741720 0.063499 0.716022 0.283 Uiso 1 1 calc R U . . .
H23C H 0.740590 -0.059486 0.670179 0.283 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
N1 Cu1 N4 107.44(12) . .
N1 Cu1 N3 160.35(12) . .
N4 Cu1 N3 83.19(12) . .
N1 Cu1 N2 82.94(12) . .
N4 Cu1 N2 158.18(13) . .
N3 Cu1 N2 92.99(13) . .
C3 O1 C2 116.1(3) . .
C21 O4 C22 115.9(4) . .
C7 N1 C6 106.8(3) . .
C7 N1 Cu1 143.1(2) . .
C6 N1 Cu1 110.1(2) . .
C10 N2 C11 119.5(3) . .
C10 N2 Cu1 112.8(2) . .
C11 N2 Cu1 127.6(3) . .
C14 N3 C13 121.4(3) . .
C14 N3 Cu1 112.5(2) . .
C13 N3 Cu1 126.0(3) . .
C18 N4 C15 106.8(3) . .
C18 N4 Cu1 142.8(2) . .
C15 N4 Cu1 110.3(2) . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1A 109.5 . .
H1B C1 H1A 109.5 . .
H1C C1 H1A 109.5 . .
O1 C2 C1 107.5(4) . .
O1 C2 H2A 110.2 . .
C1 C2 H2A 110.2 . .
O1 C2 H2B 110.2 . .
C1 C2 H2B 110.2 . .
H2A C2 H2B 108.5 . .
O2 C3 O1 121.1(3) . .
O2 C3 C4 126.0(4) . .
O1 C3 C4 112.9(3) . .
C5 C4 C7 107.6(3) . .
C5 C4 C3 124.0(3) . .
C7 C4 C3 128.3(3) . .
C6 C5 C4 105.1(3) . .
C6 C5 C8 126.3(3) . .
C4 C5 C8 128.6(3) . .
C5 C6 N1 111.3(3) . .
C5 C6 C10 133.3(3) . .
N1 C6 C10 114.7(3) . .
N1 C7 C4 109.2(3) . .
N1 C7 C9 120.8(3) . .
C4 C7 C9 129.8(3) . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N2 C10 C6 117.4(3) . .
N2 C10 H10 121.3 . .
C6 C10 H10 121.3 . .
N2 C11 C12 116.1(4) . .
N2 C11 C12A 111.1(6) . .
N2 C11 H11A 108.3 . .
C12 C11 H11A 108.3 . .
N2 C11 H11B 108.3 . .
C12 C11 H11B 108.3 . .
H11A C11 H11B 107.4 . .
N2 C11 H11C 109.4 . .
C12A C11 H11C 109.4 . .
N2 C11 H11D 109.4 . .
C12A C11 H11D 109.4 . .
H11C C11 H11D 108.0 . .
C11 C12 C13 119.6(4) . .
C11 C12 H12A 107.4 . .
C13 C12 H12A 107.4 . .
C11 C12 H12B 107.4 . .
C13 C12 H12B 107.4 . .
H12A C12 H12B 107.0 . .
C13 C12A C11 121.0(6) . .
C13 C12A H12C 107.1 . .
C11 C12A H12C 107.1 . .
C13 C12A H12D 107.1 . .
C11 C12A H12D 107.1 . .
H12C C12A H12D 106.8 . .
N3 C13 C12A 118.5(6) . .
N3 C13 C12 110.5(3) . .
N3 C13 H13A 109.6 . .
C12 C13 H13A 109.6 . .
N3 C13 H13B 109.6 . .
C12 C13 H13B 109.6 . .
H13A C13 H13B 108.1 . .
N3 C13 H13C 107.7 . .
C12A C13 H13C 107.7 . .
N3 C13 H13D 107.7 . .
C12A C13 H13D 107.7 . .
H13C C13 H13D 107.1 . .
N3 C14 C15 117.6(3) . .
N3 C14 H14 121.2 . .
C15 C14 H14 121.2 . .
C16 C15 N4 111.9(3) . .
C16 C15 C14 132.8(3) . .
N4 C15 C14 114.9(3) . .
C15 C16 C17 104.4(3) . .
C15 C16 C19 126.3(3) . .
C17 C16 C19 129.2(3) . .
C18 C17 C16 107.6(3) . .
C18 C17 C21 122.8(4) . .
C16 C17 C21 129.5(4) . .
N4 C18 C17 109.2(3) . .
N4 C18 C20 122.3(3) . .
C17 C18 C20 128.3(3) . .
C16 C19 H19A 109.5 . .
C16 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C16 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
O3 C21 O4 122.3(4) . .
O3 C21 C17 125.9(4) . .
O4 C21 C17 111.8(4) . .
O4 C22 C23 109.5(5) . .
O4 C22 H22A 109.8 . .
C23 C22 H22A 109.8 . .
O4 C22 H22B 109.8 . .
C23 C22 H22B 109.8 . .
H22A C22 H22B 108.2 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.965(3) .
Cu1 N4 1.965(3) .
Cu1 N3 1.977(3) .
Cu1 N2 1.977(3) .
O1 C3 1.361(5) .
O1 C2 1.438(5) .
O2 C3 1.208(5) .
O3 C21 1.203(6) .
O4 C21 1.342(6) .
O4 C22 1.429(4) .
N1 C7 1.349(4) .
N1 C6 1.399(4) .
N2 C10 1.289(5) .
N2 C11 1.463(5) .
N3 C14 1.297(5) .
N3 C13 1.464(4) .
N4 C18 1.347(4) .
N4 C15 1.392(4) .
C1 C2 1.482(6) .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C1 H1A 0.9600 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.456(5) .
C4 C5 1.416(5) .
C4 C7 1.421(5) .
C5 C6 1.382(5) .
C5 C8 1.497(5) .
C6 C10 1.430(5) .
C7 C9 1.493(5) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10 0.9300 .
C11 C12 1.477(4) .
C11 C12A 1.479(5) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 H11C 0.9700 .
C11 H11D 0.9700 .
C12 C13 1.500(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12A C13 1.476(5) .
C12A H12C 0.9700 .
C12A H12D 0.9700 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 H13C 0.9700 .
C13 H13D 0.9700 .
C14 C15 1.427(5) .
C14 H14 0.9300 .
C15 C16 1.382(5) .
C16 C17 1.426(5) .
C16 C19 1.501(5) .
C17 C18 1.422(5) .
C17 C21 1.471(5) .
C18 C20 1.491(5) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C22 C23 1.455(5) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
