#------------------------------------------------------------------------------
#$Date: 2023-09-08 01:56:23 +0300 (Fri, 08 Sep 2023) $
#$Revision: 286269 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/39/7713912.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_7713912
loop_
_publ_author_name
'Arruri, Sathyanarayana'
'Réveret, François'
'Jouffret, Laurent'
'Boyer, Damien'
'Chadeyron, Genevieve'
'Cisnetti, Federico'
_publ_section_title
;
 Polymeric copper(I)--NHC complexes with bulky bidentate (N^C) ligands:
 synthesis and solid-state luminescence
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01669B
_journal_year                    2023
_chemical_formula_sum            'C21 H25 Br Cu N3 O'
_chemical_formula_weight         478.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-29 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.637(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5159(16)
_cell_length_b                   9.8890(11)
_cell_length_c                   14.8049(16)
_cell_measurement_reflns_used    1870
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      26.7864
_cell_measurement_theta_min      2.5043
_cell_volume                     2124.3(4)
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_collection       APEX2
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            81002
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.595
_diffrn_reflns_theta_min         2.753
_diffrn_source                   molybdene
_exptl_absorpt_coefficient_mu    2.924
_exptl_absorpt_correction_T_max  0.7325
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.149
_refine_diff_density_max         1.070
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         6476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0313
_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)+(0.0370P)²+1.3533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5126
_reflns_number_total             6476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01669b2.cif
_cod_data_source_block           2023_CX37_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7713912
_shelx_shelxl_version_number     2018/3
_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   0.598
_shelx_estimated_absorpt_t_max   0.670
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'
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
Cu Cu 0.36645(2) 0.43428(2) 0.32247(2) 0.02052(6) Uani 1 1 d . . . . .
Br1 Br 0.33846(2) 0.51327(2) 0.46886(2) 0.03533(7) Uani 1 1 d . . . . .
O1 O -0.07724(10) 0.39141(14) 0.16264(10) 0.0302(3) Uani 1 1 d . . . . .
N1 N 0.27588(10) 0.60827(15) 0.18177(10) 0.0194(3) Uani 1 1 d . . . . .
N2 N 0.39522(11) 0.50873(16) 0.13378(11) 0.0227(3) Uani 1 1 d . . . . .
N3 N 0.07121(10) 0.74848(15) 0.16319(10) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.34242(12) 0.51850(17) 0.20771(12) 0.0197(3) Uani 1 1 d . . . . .
C2 C 0.28767(13) 0.6548(2) 0.09461(13) 0.0261(4) Uani 1 1 d . . . . .
H2 H 0.250125 0.718458 0.062688 0.031 Uiso 1 1 calc R U . . .
C3 C 0.36291(14) 0.5918(2) 0.06409(13) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.388809 0.602101 0.006285 0.034 Uiso 1 1 calc R U . . .
C4 C 0.20325(12) 0.65242(18) 0.24189(12) 0.0208(3) Uani 1 1 d . . . . .
H4A H 0.213028 0.748820 0.257435 0.025 Uiso 1 1 calc R U . . .
H4B H 0.207685 0.599497 0.298611 0.025 Uiso 1 1 calc R U . . .
C5 C 0.10799(12) 0.63531(17) 0.19981(12) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.06155(13) 0.51181(18) 0.19955(13) 0.0235(4) Uani 1 1 d . . . . .
C7 C -0.02672(13) 0.50895(18) 0.15996(13) 0.0229(4) Uani 1 1 d . . . . .
C8 C -0.06605(13) 0.6245(2) 0.12167(13) 0.0259(4) Uani 1 1 d . . . . .
C9 C -0.01336(13) 0.74167(19) 0.12529(13) 0.0245(4) Uani 1 1 d . . . . .
H9 H -0.038902 0.821644 0.099326 0.029 Uiso 1 1 calc R U . . .
C10 C 0.10251(16) 0.3863(2) 0.24215(19) 0.0414(6) Uani 1 1 d . . . . .
H10A H 0.055091 0.338554 0.275550 0.062 Uiso 1 1 calc R U . . .
H10B H 0.153353 0.411598 0.283738 0.062 Uiso 1 1 calc R U . . .
H10C H 0.125734 0.327009 0.194877 0.062 Uiso 1 1 calc R U . . .
C11 C -0.16179(16) 0.6255(3) 0.07976(18) 0.0433(6) Uani 1 1 d . . . . .
H11A H -0.182415 0.719093 0.071340 0.065 Uiso 1 1 calc R U . . .
H11B H -0.203912 0.578222 0.119591 0.065 Uiso 1 1 calc R U . . .
H11C H -0.161362 0.579684 0.021061 0.065 Uiso 1 1 calc R U . . .
C12 C -0.06844(19) 0.3087(2) 0.08339(17) 0.0449(6) Uani 1 1 d . . . . .
H12A H -0.110495 0.231429 0.086629 0.067 Uiso 1 1 calc R U . . .
H12B H -0.004898 0.275951 0.080145 0.067 Uiso 1 1 calc R U . . .
H12C H -0.083933 0.362354 0.029418 0.067 Uiso 1 1 calc R U . . .
C13 C 0.46987(13) 0.41289(19) 0.13013(13) 0.0236(4) Uani 1 1 d . . . . .
C14 C 0.45449(14) 0.2897(2) 0.08612(13) 0.0271(4) Uani 1 1 d . . . . .
C15 C 0.52353(16) 0.1929(2) 0.09271(15) 0.0362(5) Uani 1 1 d . . . . .
H15 H 0.514392 0.108456 0.063237 0.043 Uiso 1 1 calc R U . . .
C16 C 0.60532(16) 0.2153(3) 0.14083(15) 0.0397(6) Uani 1 1 d . . . . .
C17 C 0.61913(15) 0.3402(3) 0.18045(15) 0.0403(6) Uani 1 1 d . . . . .
H17 H 0.676189 0.357895 0.211207 0.048 Uiso 1 1 calc R U . . .
C18 C 0.55220(14) 0.4412(2) 0.17688(14) 0.0315(4) Uani 1 1 d . . . . .
C19 C 0.56781(17) 0.5743(3) 0.2244(2) 0.0517(7) Uani 1 1 d . . . . .
H19A H 0.546195 0.648186 0.185139 0.078 Uiso 1 1 calc R U . . .
H19B H 0.633734 0.585764 0.238434 0.078 Uiso 1 1 calc R U . . .
H19C H 0.533665 0.575413 0.280552 0.078 Uiso 1 1 calc R U . . .
C20 C 0.36619(16) 0.2626(3) 0.03328(17) 0.0413(5) Uani 1 1 d . . . . .
H20A H 0.313689 0.291513 0.068721 0.062 Uiso 1 1 calc R U . . .
H20B H 0.361076 0.165677 0.020423 0.062 Uiso 1 1 calc R U . . .
H20C H 0.366354 0.313125 -0.023675 0.062 Uiso 1 1 calc R U . . .
C21 C 0.6768(2) 0.1045(3) 0.1500(2) 0.0633(9) Uani 1 1 d . . . . .
H21A H 0.650549 0.027144 0.181704 0.095 Uiso 1 1 calc R U . . .
H21B H 0.730655 0.138379 0.184376 0.095 Uiso 1 1 calc R U . . .
H21C H 0.695471 0.076020 0.089794 0.095 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'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C1 Cu N3 123.27(7) . 2_545 ?
C1 Cu Br1 129.92(5) . . ?
N3 Cu Br1 106.79(4) 2_545 . ?
C7 O1 C12 113.39(16) . . ?
C1 N1 C2 111.98(15) . . ?
C1 N1 C4 122.73(15) . . ?
C2 N1 C4 125.25(15) . . ?
C1 N2 C3 111.72(15) . . ?
C1 N2 C13 121.29(15) . . ?
C3 N2 C13 126.78(16) . . ?
C9 N3 C5 118.40(15) . . ?
C9 N3 Cu 118.98(12) . 2 ?
C5 N3 Cu 122.18(12) . 2 ?
N2 C1 N1 103.40(15) . . ?
N2 C1 Cu 126.27(13) . . ?
N1 C1 Cu 130.14(13) . . ?
C3 C2 N1 106.39(16) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C2 C3 N2 106.50(17) . . ?
C2 C3 H3 126.8 . . ?
N2 C3 H3 126.8 . . ?
N1 C4 C5 112.47(14) . . ?
N1 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N3 C5 C6 122.70(16) . . ?
N3 C5 C4 114.88(15) . . ?
C6 C5 C4 122.42(16) . . ?
C7 C6 C5 117.21(16) . . ?
C7 C6 C10 120.41(17) . . ?
C5 C6 C10 122.36(17) . . ?
O1 C7 C8 119.54(17) . . ?
O1 C7 C6 119.30(17) . . ?
C8 C7 C6 121.09(16) . . ?
C9 C8 C7 116.78(17) . . ?
C9 C8 C11 120.76(18) . . ?
C7 C8 C11 122.44(18) . . ?
N3 C9 C8 123.81(17) . . ?
N3 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.05(18) . . ?
C18 C13 N2 118.99(18) . . ?
C14 C13 N2 118.73(17) . . ?
C15 C14 C13 117.62(19) . . ?
C15 C14 C20 121.1(2) . . ?
C13 C14 C20 121.31(19) . . ?
C16 C15 C14 122.2(2) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C17 C16 C15 118.3(2) . . ?
C17 C16 C21 121.3(2) . . ?
C15 C16 C21 120.4(3) . . ?
C16 C17 C18 122.2(2) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 117.5(2) . . ?
C13 C18 C19 121.6(2) . . ?
C17 C18 C19 120.9(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
Cu C1 1.9152(18) . ?
Cu N3 2.0565(15) 2_545 ?
Cu Br1 2.3500(4) . ?
O1 C7 1.376(2) . ?
O1 C12 1.439(3) . ?
N1 C1 1.359(2) . ?
N1 C2 1.385(2) . ?
N1 C4 1.466(2) . ?
N2 C1 1.357(2) . ?
N2 C3 1.390(2) . ?
N2 C13 1.442(2) . ?
N3 C9 1.337(2) . ?
N3 C5 1.347(2) . ?
C2 C3 1.346(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.510(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.395(2) . ?
C6 C7 1.394(3) . ?
C6 C10 1.507(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.389(3) . ?
C8 C11 1.506(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.392(3) . ?
C13 C14 1.396(3) . ?
C14 C15 1.387(3) . ?
C14 C20 1.506(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(4) . ?
C16 C21 1.513(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.506(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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
_geom_torsion_publ_flag
C3 N2 C1 N1 0.8(2) . . . . ?
C13 N2 C1 N1 -174.30(16) . . . . ?
C3 N2 C1 Cu -174.60(14) . . . . ?
C13 N2 C1 Cu 10.3(3) . . . . ?
C2 N1 C1 N2 -0.9(2) . . . . ?
C4 N1 C1 N2 -178.72(15) . . . . ?
C2 N1 C1 Cu 174.21(14) . . . . ?
C4 N1 C1 Cu -3.6(3) . . . . ?
C1 N1 C2 C3 0.7(2) . . . . ?
C4 N1 C2 C3 178.47(17) . . . . ?
N1 C2 C3 N2 -0.2(2) . . . . ?
C1 N2 C3 C2 -0.4(2) . . . . ?
C13 N2 C3 C2 174.38(18) . . . . ?
C1 N1 C4 C5 -127.37(17) . . . . ?
C2 N1 C4 C5 55.1(2) . . . . ?
C9 N3 C5 C6 0.1(3) . . . . ?
Cu N3 C5 C6 172.42(14) 2 . . . ?
C9 N3 C5 C4 -179.44(15) . . . . ?
Cu N3 C5 C4 -7.2(2) 2 . . . ?
N1 C4 C5 N3 -98.64(18) . . . . ?
N1 C4 C5 C6 81.8(2) . . . . ?
N3 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 178.98(16) . . . . ?
N3 C5 C6 C10 -178.9(2) . . . . ?
C4 C5 C6 C10 0.7(3) . . . . ?
C12 O1 C7 C8 88.9(2) . . . . ?
C12 O1 C7 C6 -94.2(2) . . . . ?
C5 C6 C7 O1 -176.33(16) . . . . ?
C10 C6 C7 O1 2.0(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C10 C6 C7 C8 178.9(2) . . . . ?
O1 C7 C8 C9 176.69(17) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
O1 C7 C8 C11 -2.0(3) . . . . ?
C6 C7 C8 C11 -179.0(2) . . . . ?
C5 N3 C9 C8 0.3(3) . . . . ?
Cu N3 C9 C8 -172.27(15) 2 . . . ?
C7 C8 C9 N3 -0.2(3) . . . . ?
C11 C8 C9 N3 178.5(2) . . . . ?
C1 N2 C13 C18 -76.8(2) . . . . ?
C3 N2 C13 C18 108.9(2) . . . . ?
C1 N2 C13 C14 97.8(2) . . . . ?
C3 N2 C13 C14 -76.4(2) . . . . ?
C18 C13 C14 C15 2.0(3) . . . . ?
N2 C13 C14 C15 -172.48(17) . . . . ?
C18 C13 C14 C20 -178.0(2) . . . . ?
N2 C13 C14 C20 7.6(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C20 C14 C15 C16 180.0(2) . . . . ?
C14 C15 C16 C17 -2.4(3) . . . . ?
C14 C15 C16 C21 177.0(2) . . . . ?
C15 C16 C17 C18 2.9(3) . . . . ?
C21 C16 C17 C18 -176.5(2) . . . . ?
C14 C13 C18 C17 -1.5(3) . . . . ?
N2 C13 C18 C17 172.93(18) . . . . ?
C14 C13 C18 C19 -179.8(2) . . . . ?
N2 C13 C18 C19 -5.3(3) . . . . ?
C16 C17 C18 C13 -1.0(3) . . . . ?
C16 C17 C18 C19 177.2(2) . . . . ?
