#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:19:02 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257598 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239953.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_7239953
loop_
_publ_author_name
'Largeron, Martine'
'Deschamps, Patrick'
'Hammad, Karim'
'Fleury, Maurice-Bernard'
_publ_section_title
;
 A dual biomimetic process for the selective aerobic oxidative coupling of
 primary amines using pyrogallol as a precatalyst. Isolation of the [5 +
 2] cycloaddition redox intermediates
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1894
_journal_page_last               1905
_journal_paper_doi               10.1039/C9GC03992A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_chemical_name_systematic        2-cyclopropyl-1-phenyl-1H-benzoimidazole
_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
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-02-04 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                103.3680(10)
_cell_angle_beta                 111.3160(10)
_cell_angle_gamma                90.2670(10)
_cell_formula_units_Z            4
_cell_length_a                   10.3880(4)
_cell_length_b                   10.8621(4)
_cell_length_c                   11.9356(4)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      59.0
_cell_measurement_theta_min      4.11
_cell_volume                     1214.77(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS ICMMO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29618
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        59.042
_diffrn_reflns_theta_max         59.042
_diffrn_reflns_theta_min         4.106
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_correction_T_min  0.8840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_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)+(0.0380P)²+0.4114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3328
_reflns_number_total             3491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc03992a2.cif
_cod_data_source_block           25d
_cod_depositor_comments
;Adding full bibliography for 7239951--7239953.cif.

 Adding full bibliography for 7239951--7239953.cif.
;
_cod_database_code               7239953
_shelx_shelxl_version_number     2016/6
_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   0.886
_shelx_estimated_absorpt_t_max   0.943
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
N1 N 0.61439(10) 0.85980(9) 0.27240(9) 0.0148(2) Uani 1 1 d . . . . .
C2 C 0.71118(12) 0.80988(11) 0.36103(11) 0.0151(3) Uani 1 1 d . . . . .
N3 N 0.83975(10) 0.84198(9) 0.37617(9) 0.0163(2) Uani 1 1 d . . . . .
C3A C 0.82883(12) 0.91664(11) 0.29338(11) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.93141(13) 0.97648(11) 0.26943(12) 0.0181(3) Uani 1 1 d . . . . .
H4 H 1.026919 0.969273 0.312295 0.022 Uiso 1 1 calc R U . . .
C5 C 0.89015(13) 1.04690(11) 0.18121(11) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.958853 1.088180 0.163733 0.023 Uiso 1 1 calc R U . . .
C6 C 0.74996(13) 1.05869(11) 0.11731(11) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.725217 1.107351 0.057206 0.021 Uiso 1 1 calc R U . . .
C7 C 0.64682(13) 1.00032(11) 0.14058(11) 0.0164(3) Uani 1 1 d . . . . .
H7 H 0.551388 1.008425 0.098394 0.020 Uiso 1 1 calc R U . . .
C7A C 0.68936(12) 0.92949(11) 0.22835(11) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.46626(12) 0.84989(11) 0.23241(11) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.40151(12) 0.95968(12) 0.25360(11) 0.0173(3) Uani 1 1 d . . . . .
H9 H 0.455194 1.039004 0.297585 0.021 Uiso 1 1 calc R U . . .
C10 C 0.25818(13) 0.95229(12) 0.21001(11) 0.0188(3) Uani 1 1 d . . . . .
H10 H 0.213014 1.026987 0.223536 0.023 Uiso 1 1 calc R U . . .
C11 C 0.18001(13) 0.83615(12) 0.14657(11) 0.0177(3) Uani 1 1 d . . . . .
H11 H 0.081535 0.831354 0.117324 0.021 Uiso 1 1 calc R U . . .
C12 C 0.24549(13) 0.72723(12) 0.12587(11) 0.0185(3) Uani 1 1 d . . . . .
H12 H 0.191855 0.647798 0.082396 0.022 Uiso 1 1 calc R U . . .
C13 C 0.38893(12) 0.73392(12) 0.16842(11) 0.0173(3) Uani 1 1 d . . . . .
H13 H 0.434012 0.659405 0.153796 0.021 Uiso 1 1 calc R U . . .
C14 C 0.67062(13) 0.73308(11) 0.43119(11) 0.0177(3) Uani 1 1 d . . . . .
H14 H 0.568834 0.712424 0.407678 0.021 Uiso 1 1 calc R U . . .
C15 C 0.76464(13) 0.63463(12) 0.47690(12) 0.0214(3) Uani 1 1 d . . . . .
H15A H 0.720648 0.554727 0.479280 0.028 Uiso 1 1 calc R U . . .
H15B H 0.848333 0.624967 0.455650 0.028 Uiso 1 1 calc R U . . .
C16 C 0.76154(14) 0.75327(12) 0.56716(12) 0.0226(3) Uani 1 1 d . . . . .
H16A H 0.843275 0.817158 0.601818 0.029 Uiso 1 1 calc R U . . .
H16B H 0.715579 0.746912 0.625450 0.029 Uiso 1 1 calc R U . . .
N17 N 0.10832(10) 0.52280(9) 0.26459(9) 0.0147(2) Uani 1 1 d . . . . .
C18 C 0.20530(12) 0.61631(11) 0.35626(11) 0.0150(3) Uani 1 1 d . . . . .
N19 N 0.33385(10) 0.59166(9) 0.37286(9) 0.0161(2) Uani 1 1 d . . . . .
C19A C 0.32274(12) 0.47630(11) 0.28823(11) 0.0153(3) Uani 1 1 d . . . . .
C20 C 0.42556(13) 0.40468(12) 0.26537(12) 0.0188(3) Uani 1 1 d . . . . .
H20 H 0.521133 0.433286 0.310198 0.023 Uiso 1 1 calc R U . . .
C21 C 0.38438(13) 0.29062(12) 0.17543(12) 0.0202(3) Uani 1 1 d . . . . .
H21 H 0.453174 0.240509 0.158878 0.024 Uiso 1 1 calc R U . . .
C22 C 0.24413(13) 0.24720(12) 0.10826(11) 0.0193(3) Uani 1 1 d . . . . .
H22 H 0.219506 0.168592 0.046998 0.023 Uiso 1 1 calc R U . . .
C23 C 0.14071(13) 0.31724(11) 0.12985(11) 0.0170(3) Uani 1 1 d . . . . .
H23 H 0.045203 0.288462 0.084904 0.020 Uiso 1 1 calc R U . . .
C23A C 0.18298(12) 0.43126(11) 0.22004(11) 0.0144(3) Uani 1 1 d . . . . .
C24 C -0.04004(12) 0.51290(11) 0.22355(11) 0.0148(3) Uani 1 1 d . . . . .
C25 C -0.11537(13) 0.59776(11) 0.16099(11) 0.0180(3) Uani 1 1 d . . . . .
H25 H -0.068740 0.665054 0.147520 0.022 Uiso 1 1 calc R U . . .
C26 C -0.25894(13) 0.58398(12) 0.11823(11) 0.0195(3) Uani 1 1 d . . . . .
H26 H -0.310989 0.642590 0.076243 0.023 Uiso 1 1 calc R U . . .
C27 C -0.32679(13) 0.48487(12) 0.13659(11) 0.0188(3) Uani 1 1 d . . . . .
H27 H -0.425339 0.475023 0.106626 0.023 Uiso 1 1 calc R U . . .
C28 C -0.25046(13) 0.39992(12) 0.19887(11) 0.0195(3) Uani 1 1 d . . . . .
H28 H -0.297125 0.331873 0.211264 0.023 Uiso 1 1 calc R U . . .
C29 C -0.10730(13) 0.41370(11) 0.24288(11) 0.0179(3) Uani 1 1 d . . . . .
H29 H -0.055239 0.355859 0.286009 0.021 Uiso 1 1 calc R U . . .
C30 C 0.16500(13) 0.72747(11) 0.42770(11) 0.0176(3) Uani 1 1 d . . . . .
H30 H 0.063374 0.737005 0.402292 0.021 Uiso 1 1 calc R U . . .
C31 C 0.25275(14) 0.77265(12) 0.56498(12) 0.0230(3) Uani 1 1 d . . . . .
H31A H 0.204972 0.807168 0.622036 0.030 Uiso 1 1 calc R U . . .
H31B H 0.332572 0.724997 0.599603 0.030 Uiso 1 1 calc R U . . .
C32 C 0.26163(13) 0.84861(12) 0.47880(11) 0.0206(3) Uani 1 1 d . . . . .
H32A H 0.347034 0.848104 0.460123 0.027 Uiso 1 1 calc R U . . .
H32B H 0.219458 0.930260 0.482551 0.027 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 0.0181 0.0091 '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 0.0311 0.0180 '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
C2 N1 C7A 106.38(9) . . ?
C2 N1 C8 129.61(10) . . ?
C7A N1 C8 123.98(10) . . ?
N3 C2 N1 112.74(10) . . ?
N3 C2 C14 125.06(11) . . ?
N1 C2 C14 122.17(10) . . ?
C2 N3 C3A 105.23(10) . . ?
N3 C3A C7A 110.30(10) . . ?
N3 C3A C4 130.46(11) . . ?
C7A C3A C4 119.24(11) . . ?
C5 C4 C3A 118.13(11) . . ?
C5 C4 H4 120.9 . . ?
C3A C4 H4 120.9 . . ?
C4 C5 C6 121.71(11) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 120.83(11) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C7A C7 C6 116.90(11) . . ?
C7A C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C7 C7A N1 131.47(11) . . ?
C7 C7A C3A 123.19(11) . . ?
N1 C7A C3A 105.35(10) . . ?
C13 C8 C9 120.76(11) . . ?
C13 C8 N1 120.40(10) . . ?
C9 C8 N1 118.77(10) . . ?
C8 C9 C10 119.31(11) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.24(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.03(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.11(11) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 119.55(11) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C2 C14 C15 117.89(11) . . ?
C2 C14 C16 117.16(10) . . ?
C15 C14 C16 58.77(8) . . ?
C2 C14 H14 116.8 . . ?
C15 C14 H14 116.8 . . ?
C16 C14 H14 116.8 . . ?
C16 C15 C14 60.68(8) . . ?
C16 C15 H15A 117.7 . . ?
C14 C15 H15A 117.7 . . ?
C16 C15 H15B 117.7 . . ?
C14 C15 H15B 117.7 . . ?
H15A C15 H15B 114.8 . . ?
C15 C16 C14 60.55(8) . . ?
C15 C16 H16A 117.7 . . ?
C14 C16 H16A 117.7 . . ?
C15 C16 H16B 117.7 . . ?
C14 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
C18 N17 C23A 106.48(9) . . ?
C18 N17 C24 129.25(10) . . ?
C23A N17 C24 124.20(10) . . ?
N19 C18 N17 112.68(10) . . ?
N19 C18 C30 125.07(11) . . ?
N17 C18 C30 122.22(10) . . ?
C18 N19 C19A 105.30(10) . . ?
N19 C19A C23A 110.35(10) . . ?
N19 C19A C20 130.30(11) . . ?
C23A C19A C20 119.35(11) . . ?
C21 C20 C19A 118.06(12) . . ?
C21 C20 H20 121.0 . . ?
C19A C20 H20 121.0 . . ?
C20 C21 C22 121.74(11) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 120.91(12) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C23A C23 C22 116.92(11) . . ?
C23A C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
C23 C23A N17 131.79(11) . . ?
C23 C23A C19A 123.03(11) . . ?
N17 C23A C19A 105.19(10) . . ?
C25 C24 C29 120.59(11) . . ?
C25 C24 N17 120.50(10) . . ?
C29 C24 N17 118.86(10) . . ?
C24 C25 C26 119.66(11) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 120.08(11) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 119.86(11) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C29 120.43(11) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C24 C29 C28 119.37(11) . . ?
C24 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C18 C30 C32 117.94(10) . . ?
C18 C30 C31 117.25(10) . . ?
C32 C30 C31 58.83(8) . . ?
C18 C30 H30 116.8 . . ?
C32 C30 H30 116.8 . . ?
C31 C30 H30 116.8 . . ?
C32 C31 C30 60.45(8) . . ?
C32 C31 H31A 117.7 . . ?
C30 C31 H31A 117.7 . . ?
C32 C31 H31B 117.7 . . ?
C30 C31 H31B 117.7 . . ?
H31A C31 H31B 114.8 . . ?
C31 C32 C30 60.72(8) . . ?
C31 C32 H32A 117.7 . . ?
C30 C32 H32A 117.7 . . ?
C31 C32 H32B 117.7 . . ?
C30 C32 H32B 117.7 . . ?
H32A C32 H32B 114.8 . . ?
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
N1 C2 1.3860(15) . ?
N1 C7A 1.3900(15) . ?
N1 C8 1.4310(15) . ?
C2 N3 1.3149(16) . ?
C2 C14 1.4667(17) . ?
N3 C3A 1.3917(16) . ?
C3A C7A 1.3983(17) . ?
C3A C4 1.3931(17) . ?
C4 C5 1.3873(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3994(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3851(18) . ?
C6 H6 0.9500 . ?
C7 C7A 1.3871(17) . ?
C7 H7 0.9500 . ?
C8 C13 1.3839(17) . ?
C8 C9 1.3893(17) . ?
C9 C10 1.3822(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3878(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3848(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3840(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.5123(17) . ?
C14 C16 1.5142(18) . ?
C14 H14 1.0000 . ?
C15 C16 1.4852(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C18 1.3852(16) . ?
N17 C23A 1.3912(15) . ?
N17 C24 1.4325(15) . ?
C18 N19 1.3152(15) . ?
C18 C30 1.4657(17) . ?
N19 C19A 1.3901(16) . ?
C19A C23A 1.3999(17) . ?
C19A C20 1.3936(17) . ?
C20 C21 1.3843(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.3991(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.3847(18) . ?
C22 H22 0.9500 . ?
C23 C23A 1.3857(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3855(17) . ?
C24 C29 1.3884(17) . ?
C25 C26 1.3843(17) . ?
C25 H25 0.9500 . ?
C26 C27 1.3849(18) . ?
C26 H26 0.9500 . ?
C27 C28 1.3886(18) . ?
C27 H27 0.9500 . ?
C28 C29 1.3797(17) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C32 1.5107(17) . ?
C30 C31 1.5148(18) . ?
C30 H30 1.0000 . ?
C31 C32 1.4858(18) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
