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#$Date: 2024-01-06 08:48:44 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288718 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/03/1570383.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.
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data_1570383
loop_
_publ_author_name
'Jin, Xiaodong'
'Lin, Yongjie'
'Davies, Robert P.'
_publ_section_title
;
 On the mechanism of benzimidazole synthesis via copper-catalysed
 intramolecular N-arylation
;
_journal_issue                   24
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              7181
_journal_page_last               7189
_journal_paper_doi               10.1039/D3CY00767G
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C30 H28 Cu2 F2 N6'
_chemical_formula_sum            'C30 H28 Cu2 F2 N6'
_chemical_formula_weight         637.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-16 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3777(6)
_cell_length_b                   14.5390(5)
_cell_length_c                   10.7488(4)
_cell_measurement_reflns_used    1581
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.8630
_cell_measurement_theta_min      2.7590
_cell_volume                     2715.73(17)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.810
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.810
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6013
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.208
_diffrn_reflns_theta_min         2.356
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET) 
(compiled Mar 28 2014,12:25:20) 
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_crystal_colour            Red
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       needles
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0412
_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)+(0.0528P)²+1.2372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2262
_reflns_number_total             2815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cy00767g2.cif
_cod_data_source_block           1d-phen
_cod_depositor_comments
'Adding full bibliography for 1570378--1570383.cif.'
_cod_original_cell_volume        2715.71(17)
_cod_database_code               1570383
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
Cu1 Cu 0.65347(3) 0.750000 0.64684(5) 0.01988(16) Uani 1 2 d S T P . .
Cu2 Cu 0.60473(3) 0.750000 0.42264(5) 0.01954(16) Uani 1 2 d S T P . .
N1 N 0.61441(14) 0.62112(16) 0.6328(2) 0.0203(6) Uani 1 1 d . . . . .
C2 C 0.60753(16) 0.5754(2) 0.5287(3) 0.0212(7) Uani 1 1 d . . . . .
N3 N 0.60776(14) 0.62220(16) 0.4201(2) 0.0206(5) Uani 1 1 d . . . . .
C4 C 0.6025(2) 0.5712(2) 0.7495(3) 0.0322(8) Uani 1 1 d . . . . .
H4A H 0.620623 0.608833 0.819204 0.048 Uiso 1 1 calc R U . . .
H4B H 0.631282 0.513292 0.747306 0.048 Uiso 1 1 calc R U . . .
H4C H 0.547544 0.558126 0.760011 0.048 Uiso 1 1 calc R U . . .
C5 C 0.59533(19) 0.4722(2) 0.5275(3) 0.0297(8) Uani 1 1 d . . . . .
H5A H 0.642312 0.441407 0.555943 0.045 Uiso 1 1 calc R U . . .
H5B H 0.583149 0.452101 0.442767 0.045 Uiso 1 1 calc R U . . .
H5C H 0.552640 0.456383 0.583125 0.045 Uiso 1 1 calc R U . . .
C6 C 0.61817(18) 0.57848(19) 0.3049(3) 0.0229(7) Uani 1 1 d . . . . .
C7 C 0.5691(2) 0.5970(2) 0.2050(3) 0.0298(7) Uani 1 1 d . . . . .
H7A H 0.527027 0.637607 0.218042 0.036 Uiso 0.429(5) 1 calc R U P A 2
F1 F 0.50947(19) 0.6510(2) 0.2260(3) 0.0402(12) Uani 0.571(5) 1 d . U P A 1
C8 C 0.5788(2) 0.5591(2) 0.0884(3) 0.0368(9) Uani 1 1 d . . . . .
H8A H 0.543634 0.573396 0.023515 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6395(2) 0.5005(2) 0.0661(4) 0.0406(9) Uani 1 1 d . . . . .
H9A H 0.646235 0.473807 -0.013781 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6907(2) 0.4809(2) 0.1615(4) 0.0377(9) Uani 1 1 d . . . . .
H10A H 0.733062 0.441032 0.147207 0.045 Uiso 1 1 calc R U . . .
C11 C 0.67959(19) 0.5200(2) 0.2776(3) 0.0318(8) Uani 1 1 d . . . . .
H11A H 0.715448 0.506265 0.341730 0.038 Uiso 0.571(5) 1 calc R U P A 1
F1' F 0.7286(3) 0.5018(3) 0.3660(5) 0.0449(16) Uiso 0.429(5) 1 d . U P A 2
N21 N 0.7717(2) 0.750000 0.5871(4) 0.0273(9) Uani 1 2 d S T P . .
C22 C 0.7982(3) 0.750000 0.4715(5) 0.0371(12) Uani 1 2 d S T P . .
H22A H 0.761873 0.750000 0.405512 0.044 Uiso 1 2 calc R U P . .
C23 C 0.8761(3) 0.750000 0.4407(6) 0.0509(16) Uani 1 2 d S T P . .
H23A H 0.892062 0.750000 0.356142 0.061 Uiso 1 2 calc R U P . .
C24 C 0.9285(3) 0.750000 0.5341(7) 0.0522(17) Uani 1 2 d S T P . .
H24A H 0.981952 0.750000 0.515567 0.063 Uiso 1 2 calc R U P . .
C25 C 0.9037(3) 0.750000 0.6571(6) 0.0427(15) Uani 1 2 d S T P . .
C26 C 0.9551(3) 0.750000 0.7602(8) 0.0569(19) Uani 1 2 d S T P . .
H26A H 1.009010 0.750000 0.745245 0.068 Uiso 1 2 calc R U P . .
C27 C 0.9293(3) 0.750000 0.8781(8) 0.0556(19) Uani 1 2 d S T P . .
H27A H 0.965334 0.750000 0.944603 0.067 Uiso 1 2 calc R U P . .
C28 C 0.8481(3) 0.750000 0.9057(6) 0.0406(14) Uani 1 2 d S T P . .
C29 C 0.8180(4) 0.750000 1.0257(6) 0.0558(18) Uani 1 2 d S T P . .
H29A H 0.851853 0.750000 1.095089 0.067 Uiso 1 2 calc R U P . .
C30 C 0.7402(4) 0.750000 1.0448(5) 0.0496(16) Uani 1 2 d S T P . .
H30A H 0.719170 0.750000 1.126364 0.059 Uiso 1 2 calc R U P . .
C31 C 0.6926(3) 0.750000 0.9399(5) 0.0366(12) Uani 1 2 d S T P . .
H31A H 0.638496 0.750000 0.952882 0.044 Uiso 1 2 calc R U P . .
N32 N 0.7177(2) 0.750000 0.8239(4) 0.0287(9) Uani 1 2 d S T P . .
C33 C 0.7954(3) 0.750000 0.8066(5) 0.0301(12) Uani 1 2 d S T P . .
C34 C 0.8241(3) 0.750000 0.6805(5) 0.0301(12) Uani 1 2 d S T P . .
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'
F F 0.0171 0.0103 '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
N1 Cu1 N1 139.27(14) . 7_575 ?
N1 Cu1 N21 107.56(7) . . ?
N1 Cu1 N21 107.56(7) 7_575 . ?
N1 Cu1 N32 103.71(8) . . ?
N1 Cu1 N32 103.71(8) 7_575 . ?
N21 Cu1 N32 76.97(15) . . ?
N1 Cu1 Cu2 79.39(7) . . ?
N1 Cu1 Cu2 79.39(7) 7_575 . ?
N21 Cu1 Cu2 92.02(11) . . ?
N32 Cu1 Cu2 168.99(11) . . ?
N3 Cu2 N3 176.32(15) . 7_575 ?
N3 Cu2 Cu1 90.27(8) . . ?
N3 Cu2 Cu1 90.27(8) 7_575 . ?
C2 N1 C4 117.9(3) . . ?
C2 N1 Cu1 125.0(2) . . ?
C4 N1 Cu1 116.6(2) . . ?
N1 C2 N3 118.9(3) . . ?
N1 C2 C5 121.6(3) . . ?
N3 C2 C5 119.5(3) . . ?
C2 N3 C6 122.3(2) . . ?
C2 N3 Cu2 119.4(2) . . ?
C6 N3 Cu2 118.02(19) . . ?
C11 C6 C7 115.0(3) . . ?
C11 C6 N3 124.1(3) . . ?
C7 C6 N3 120.8(3) . . ?
F1 C7 C8 119.2(3) . . ?
F1 C7 C6 117.6(3) . . ?
C8 C7 C6 123.1(3) . . ?
C9 C8 C7 119.9(3) . . ?
C8 C9 C10 119.4(3) . . ?
C11 C10 C9 119.5(3) . . ?
F1' C11 C10 118.9(4) . . ?
F1' C11 C6 118.0(4) . . ?
C10 C11 C6 123.1(3) . . ?
C22 N21 C34 117.5(4) . . ?
C22 N21 Cu1 127.7(3) . . ?
C34 N21 Cu1 114.8(3) . . ?
N21 C22 C23 124.1(5) . . ?
C24 C23 C22 118.4(6) . . ?
C23 C24 C25 119.7(5) . . ?
C24 C25 C34 118.4(5) . . ?
C24 C25 C26 123.1(5) . . ?
C34 C25 C26 118.6(6) . . ?
C27 C26 C25 121.6(5) . . ?
C26 C27 C28 121.3(5) . . ?
C29 C28 C33 117.3(5) . . ?
C29 C28 C27 123.9(5) . . ?
C33 C28 C27 118.8(6) . . ?
C30 C29 C28 120.7(5) . . ?
C29 C30 C31 117.6(6) . . ?
N32 C31 C30 124.4(5) . . ?
C31 N32 C33 117.2(4) . . ?
C31 N32 Cu1 130.3(3) . . ?
C33 N32 Cu1 112.5(3) . . ?
N32 C33 C28 122.8(5) . . ?
N32 C33 C34 118.0(4) . . ?
C28 C33 C34 119.2(5) . . ?
N21 C34 C25 121.9(5) . . ?
N21 C34 C33 117.6(4) . . ?
C25 C34 C33 120.5(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
Cu1 N1 1.999(2) . ?
Cu1 N1 1.999(2) 7_575 ?
Cu1 N21 2.153(4) . ?
Cu1 N32 2.206(4) . ?
Cu1 Cu2 2.5543(7) . ?
Cu2 N3 1.859(2) . ?
Cu2 N3 1.859(2) 7_575 ?
N1 C2 1.307(4) . ?
N1 C4 1.464(4) . ?
C2 N3 1.352(4) . ?
C2 C5 1.515(4) . ?
N3 C6 1.403(4) . ?
C6 C11 1.396(5) . ?
C6 C7 1.397(5) . ?
C7 F1 1.319(5) . ?
C7 C8 1.380(5) . ?
C8 C9 1.376(5) . ?
C9 C10 1.387(5) . ?
C10 C11 1.385(5) . ?
C11 F1' 1.303(6) . ?
N21 C22 1.325(6) . ?
N21 C34 1.355(6) . ?
C22 C23 1.392(7) . ?
C23 C24 1.356(9) . ?
C24 C25 1.391(9) . ?
C25 C34 1.406(7) . ?
C25 C26 1.423(9) . ?
C26 C27 1.345(9) . ?
C27 C28 1.443(9) . ?
C28 C29 1.392(9) . ?
C28 C33 1.404(7) . ?
C29 C30 1.368(9) . ?
C30 C31 1.398(7) . ?
C31 N32 1.320(6) . ?
N32 C33 1.364(6) . ?
C33 C34 1.444(7) . ?
