#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245179.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_7245179
loop_
_publ_author_name
'Hao, Xiujia'
'Li, Xinyu'
'Li, Haitao'
'Zhang, Xin'
'Liu, Xiaozhi'
'Guo, Fang'
_publ_section_title
;
 Mechanosynthesis of polymeric and binuclear copper complexes via
 dehydrochlorination and their application in solvent-free C--S bond
 cross-coupling
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00624C
_journal_year                    2022
_chemical_formula_moiety         'Cl4 Cu, Cl, C15 H17 N4'
_chemical_formula_sum            'C15 H17 Cl5 Cu N4'
_chemical_formula_weight         494.11
_chemical_melting_point          365.2(13)
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-08 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                104.664(7)
_cell_angle_beta                 110.573(7)
_cell_angle_gamma                110.692(8)
_cell_formula_units_Z            2
_cell_length_a                   10.502(2)
_cell_length_b                   10.560(3)
_cell_length_c                   11.248(3)
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.313
_cell_measurement_theta_min      3.069
_cell_volume                     985.9(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17315
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         3.069
_exptl_absorpt_coefficient_mu    1.792
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1074 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.6833.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       needle
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0296
_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)+(0.0295P)²+0.7515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4441
_reflns_number_total             4802
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00624c2.cif
_cod_data_source_block           20190408_2a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '363.95-366.55' was changed
to '365.2(13)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

2025-04-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H34 Cl10 Cu2 N8'
_cod_original_formula_weight         988.23
_cod_original_formula_moiety         '2(Cl4 Cu), 2(Cl), 2(C15 H17 N4)'
_cod_original_formula_units_Z            1
_cod_database_code               7245179
_shelx_shelxl_version_number     2014/7
_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_max   0.841
_shelx_estimated_absorpt_t_min   0.827
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C1(H1), C2(H2), C12(H12), C6(H6), C13(H13), C9(H9), C7(H7), C8(H8),
 C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cu01 Cu 1.16103(2) 1.22162(2) 0.90793(2) 0.02704(7) Uani 1 1 d . . . . .
Cl3 Cl 1.10472(6) 1.36181(5) 1.05166(5) 0.03749(11) Uani 1 1 d . . . . .
Cl2 Cl 0.96989(5) 1.16100(5) 0.69513(5) 0.03715(11) Uani 1 1 d . . . . .
Cl5 Cl 0.72217(5) 0.39476(5) 0.48574(5) 0.03977(11) Uani 1 1 d . . . . .
Cl4 Cl 1.22096(7) 1.09207(6) 1.02446(5) 0.04237(12) Uani 1 1 d . . . . .
Cl1 Cl 1.35408(7) 1.27951(8) 0.85692(6) 0.05371(16) Uani 1 1 d . . . . .
N1 N 0.66501(17) 0.69450(17) 0.48183(16) 0.0277(3) Uani 1 1 d . . . . .
N2 N 0.91123(17) 0.78566(16) 0.61037(15) 0.0262(3) Uani 1 1 d . . . . .
N4 N 0.33764(18) 0.7011(2) 0.22796(17) 0.0335(3) Uani 1 1 d . . . . .
N3 N 1.05359(18) 0.62033(17) 0.70043(17) 0.0298(3) Uani 1 1 d . . . . .
C3 C 0.8499(2) 0.7941(2) 0.70032(19) 0.0308(4) Uani 1 1 d . . . . .
H3A H 0.9047 0.8324 0.7978 0.037 Uiso 1 1 calc R . . . .
C11 C 0.47984(18) 0.74978(18) 0.33273(17) 0.0242(3) Uani 1 1 d . . . . .
C1 C 0.7973(2) 0.7255(2) 0.47867(19) 0.0280(3) Uani 1 1 d . . . . .
H1 H 0.8085 0.7083 0.3986 0.034 Uiso 1 1 calc R . . . .
C2 C 0.6954(2) 0.7364(2) 0.6198(2) 0.0310(4) Uani 1 1 d . . . . .
H2 H 0.6230 0.7265 0.6511 0.037 Uiso 1 1 calc R . . . .
C12 C 0.5821(2) 0.90065(19) 0.40323(19) 0.0297(3) Uani 1 1 d . . . . .
H12 H 0.6808 0.9370 0.4772 0.036 Uiso 1 1 calc R . . . .
C5 C 1.14348(19) 0.76209(18) 0.72936(17) 0.0256(3) Uani 1 1 d . . . . .
C4 C 1.0754(2) 0.8380(2) 0.6508(2) 0.0306(3) Uani 1 1 d . . . . .
H4A H 1.1343 0.9454 0.7094 0.037 Uiso 1 1 calc R . . . .
H4B H 1.0861 0.8204 0.5668 0.037 Uiso 1 1 calc R . . . .
C10 C 0.5130(2) 0.62987(19) 0.3597(2) 0.0305(3) Uani 1 1 d . . . . .
H10A H 0.4331 0.5669 0.3750 0.037 Uiso 1 1 calc R . . . .
H10B H 0.5097 0.5673 0.2777 0.037 Uiso 1 1 calc R . . . .
C6 C 1.2995(2) 0.8331(2) 0.8259(2) 0.0353(4) Uani 1 1 d . . . . .
H6 H 1.3634 0.9331 0.8500 0.042 Uiso 1 1 calc R . . . .
C13 C 0.5378(3) 0.9987(2) 0.3637(2) 0.0399(4) Uani 1 1 d . . . . .
H13 H 0.6069 1.1013 0.4110 0.048 Uiso 1 1 calc R . . . .
C9 C 1.1091(3) 0.5437(2) 0.7613(2) 0.0408(4) Uani 1 1 d . . . . .
H9 H 1.0420 0.4458 0.7400 0.049 Uiso 1 1 calc R . . . .
C7 C 1.3606(2) 0.7554(3) 0.8866(2) 0.0436(5) Uani 1 1 d . . . . .
H7 H 1.4667 0.8017 0.9490 0.052 Uiso 1 1 calc R . . . .
C8 C 1.2645(3) 0.6095(3) 0.8547(3) 0.0466(5) Uani 1 1 d . . . . .
H8 H 1.3043 0.5563 0.8959 0.056 Uiso 1 1 calc R . . . .
C14 C 0.3917(3) 0.9444(3) 0.2546(3) 0.0479(5) Uani 1 1 d . . . . .
H14 H 0.3615 1.0095 0.2265 0.057 Uiso 1 1 calc R . . . .
C15 C 0.2916(3) 0.7935(3) 0.1880(2) 0.0467(5) Uani 1 1 d . . . . .
H15 H 0.1917 0.7550 0.1150 0.056 Uiso 1 1 calc R . . . .
H3 H 0.957(3) 0.573(3) 0.640(3) 0.044(7) Uiso 1 1 d . . . . .
H4 H 0.277(3) 0.613(3) 0.189(3) 0.054(8) Uiso 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
Cl2 Cu01 Cl3 100.15(3) . . ?
Cl4 Cu01 Cl3 100.33(3) . . ?
Cl4 Cu01 Cl2 134.52(3) . . ?
Cl4 Cu01 Cl1 97.89(3) . . ?
Cl1 Cu01 Cl3 132.93(3) . . ?
Cl1 Cu01 Cl2 97.07(3) . . ?
C1 N1 C2 109.07(15) . . ?
C1 N1 C10 125.29(15) . . ?
C2 N1 C10 125.63(15) . . ?
C3 N2 C4 126.27(15) . . ?
C1 N2 C3 109.31(15) . . ?
C1 N2 C4 124.40(15) . . ?
C11 N4 H4 118(2) . . ?
C15 N4 C11 122.90(18) . . ?
C15 N4 H4 119(2) . . ?
C5 N3 C9 122.61(17) . . ?
C5 N3 H3 120.8(17) . . ?
C9 N3 H3 116.6(17) . . ?
N2 C3 H3A 126.6 . . ?
C2 C3 N2 106.76(16) . . ?
C2 C3 H3A 126.6 . . ?
N4 C11 C12 118.73(16) . . ?
N4 C11 C10 115.55(15) . . ?
C12 C11 C10 125.71(15) . . ?
N1 C1 N2 107.88(15) . . ?
N1 C1 H1 126.1 . . ?
N2 C1 H1 126.1 . . ?
N1 C2 H2 126.5 . . ?
C3 C2 N1 106.99(16) . . ?
C3 C2 H2 126.5 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.58(17) . . ?
C13 C12 H12 120.2 . . ?
N3 C5 C4 119.72(15) . . ?
N3 C5 C6 118.83(17) . . ?
C6 C5 C4 121.36(16) . . ?
N2 C4 C5 113.07(14) . . ?
N2 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N1 C10 C11 111.19(14) . . ?
N1 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.74(19) . . ?
C7 C6 H6 120.1 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.01(19) . . ?
C14 C13 H13 120.0 . . ?
N3 C9 H9 119.9 . . ?
N3 C9 C8 120.10(19) . . ?
C8 C9 H9 119.9 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.89(19) . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 118.76(19) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.90(19) . . ?
C15 C14 H14 120.5 . . ?
N4 C15 C14 119.85(19) . . ?
N4 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
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
Cu01 Cl3 2.2878(6) . ?
Cu01 Cl2 2.2601(7) . ?
Cu01 Cl4 2.2185(6) . ?
Cu01 Cl1 2.2209(7) . ?
N1 C1 1.326(2) . ?
N1 C2 1.382(2) . ?
N1 C10 1.455(2) . ?
N2 C3 1.378(2) . ?
N2 C1 1.330(2) . ?
N2 C4 1.460(2) . ?
N4 C11 1.341(2) . ?
N4 C15 1.338(3) . ?
N4 H4 0.81(3) . ?
N3 C5 1.333(2) . ?
N3 C9 1.340(2) . ?
N3 H3 0.86(3) . ?
C3 H3A 0.9300 . ?
C3 C2 1.347(3) . ?
C11 C12 1.369(2) . ?
C11 C10 1.499(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C5 C4 1.501(2) . ?
C5 C6 1.377(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.365(4) . ?
C15 H15 0.9300 . ?
