#------------------------------------------------------------------------------
#$Date: 2019-11-02 05:51:48 +0200 (Sat, 02 Nov 2019) $
#$Revision: 220753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/74/4127484.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_4127484
loop_
_publ_author_name
'Kawakita, Kento'
'Beaumier, Evan P.'
'Kakiuchi, Yuya'
'Tsurugi, Hayato'
'Tonks, Ian A.'
'Mashima, Kazushi'
_publ_section_title
;
 Bis(imido)vanadium(V)-Catalyzed [2+2+1] Coupling of Alkynes and
 Azobenzenes Giving Multisubstituted Pyrroles.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4194
_journal_page_last               4198
_journal_paper_doi               10.1021/jacs.8b13390
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C18 H28 Cl N2 P2 V'
_chemical_formula_sum            'C18 H28 Cl N2 P2 V'
_chemical_formula_weight         420.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 131.204(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   17.735(10)
_cell_length_b                   12.563(6)
_cell_length_c                   13.175(8)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.10
_cell_volume                     2209(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25134
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_min         3.053
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880.00
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details
;
 Flack x determined using 1719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5071
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0181P)²+1.1960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0592
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4298
_reflns_number_total             5071
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja8b13390_si_002.cif
_cod_data_source_block           complex7
_cod_database_code               4127484
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+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
V1 V 0.500000 0.72148(5) 0.500000 0.01318(19) Uani 1 2 d S T P
V2 V 0.500000 0.47230(5) 0.000000 0.01380(18) Uani 1 2 d S T P
CL1 Cl 0.500000 0.91463(8) 0.500000 0.0169(3) Uani 1 2 d S T P
CL2 Cl 0.500000 0.66486(8) 0.000000 0.0164(3) Uani 1 2 d S T P
P1 P 0.55515(7) 0.74706(7) 0.37295(9) 0.01827(19) Uani 1 1 d . . .
P2 P 0.32066(6) 0.49428(7) -0.11944(8) 0.01806(19) Uani 1 1 d . . .
N1 N 0.6021(2) 0.6455(2) 0.6182(3) 0.0182(6) Uani 1 1 d . . .
N2 N 0.5171(2) 0.3963(2) 0.1205(3) 0.0197(6) Uani 1 1 d . . .
C1 C 0.6630(2) 0.5572(3) 0.6852(3) 0.0195(7) Uani 1 1 d . . .
C2 C 0.6243(3) 0.4603(3) 0.6858(4) 0.0255(8) Uani 1 1 d . . .
H2 H 0.554620 0.453992 0.637406 0.031 Uiso 1 1 calc R U .
C3 C 0.6867(3) 0.3734(3) 0.7562(4) 0.0330(10) Uani 1 1 d . . .
H3 H 0.659631 0.308370 0.756666 0.040 Uiso 1 1 calc R U .
C4 C 0.7886(3) 0.3812(3) 0.8260(4) 0.0354(10) Uani 1 1 d . . .
H4 H 0.831374 0.321839 0.874831 0.043 Uiso 1 1 calc R U .
C5 C 0.8271(3) 0.4755(3) 0.8239(4) 0.0388(10) Uani 1 1 d . . .
H5 H 0.896468 0.480427 0.869995 0.047 Uiso 1 1 calc R U .
C6 C 0.7662(3) 0.5631(3) 0.7557(4) 0.0316(9) Uani 1 1 d . . .
H6 H 0.794165 0.627888 0.756444 0.038 Uiso 1 1 calc R U .
C7 C 0.6705(3) 0.8215(4) 0.4582(4) 0.0372(10) Uani 1 1 d . . .
H7A H 0.663460 0.892096 0.482731 0.045 Uiso 1 1 calc R U .
H7B H 0.725906 0.783357 0.539929 0.045 Uiso 1 1 calc R U .
H7C H 0.684502 0.829206 0.397931 0.045 Uiso 1 1 calc R U .
C8 C 0.4687(3) 0.8141(3) 0.2110(3) 0.0288(8) Uani 1 1 d . . .
H8A H 0.403000 0.779462 0.156263 0.035 Uiso 1 1 calc R U .
H8B H 0.462221 0.888857 0.225382 0.035 Uiso 1 1 calc R U .
H8C H 0.494350 0.810047 0.164160 0.035 Uiso 1 1 calc R U .
C9 C 0.5809(3) 0.6202(3) 0.3351(4) 0.0282(9) Uani 1 1 d . . .
H9A H 0.521817 0.574132 0.288364 0.034 Uiso 1 1 calc R U .
H9B H 0.596603 0.631867 0.277304 0.034 Uiso 1 1 calc R U .
H9C H 0.638007 0.586018 0.419302 0.034 Uiso 1 1 calc R U .
C10 C 0.5204(2) 0.3090(3) 0.1874(3) 0.0190(7) Uani 1 1 d . . .
C11 C 0.5653(2) 0.3163(3) 0.3235(3) 0.0244(7) Uani 1 1 d . . .
H11 H 0.594855 0.381382 0.370929 0.029 Uiso 1 1 calc R U .
C12 C 0.5665(3) 0.2289(3) 0.3886(4) 0.0353(10) Uani 1 1 d . . .
H12 H 0.596852 0.234929 0.480481 0.042 Uiso 1 1 calc R U .
C13 C 0.5246(3) 0.1330(3) 0.3226(4) 0.0346(10) Uani 1 1 d . . .
H13 H 0.526234 0.073440 0.368447 0.042 Uiso 1 1 calc R U .
C14 C 0.4799(3) 0.1251(3) 0.1880(5) 0.0332(10) Uani 1 1 d . . .
H14 H 0.450703 0.059662 0.141264 0.040 Uiso 1 1 calc R U .
C15 C 0.4778(3) 0.2116(3) 0.1219(4) 0.0259(8) Uani 1 1 d . . .
H15 H 0.446639 0.204859 0.029785 0.031 Uiso 1 1 calc R U .
C16 C 0.2431(2) 0.5684(3) -0.2766(3) 0.0280(8) Uani 1 1 d . . .
H16A H 0.251897 0.539669 -0.337349 0.034 Uiso 1 1 calc R U .
H16B H 0.172580 0.562113 -0.319119 0.034 Uiso 1 1 calc R U .
H16C H 0.262841 0.643557 -0.258232 0.034 Uiso 1 1 calc R U .
C17 C 0.2944(3) 0.5582(4) -0.0226(4) 0.0386(10) Uani 1 1 d . . .
H17A H 0.333196 0.523615 0.065694 0.046 Uiso 1 1 calc R U .
H17B H 0.312959 0.633599 -0.010005 0.046 Uiso 1 1 calc R U .
H17C H 0.222698 0.552155 -0.070892 0.046 Uiso 1 1 calc R U .
C18 C 0.2580(3) 0.3662(3) -0.1664(4) 0.0350(10) Uani 1 1 d . . .
H18A H 0.268783 0.326226 -0.219788 0.042 Uiso 1 1 calc R U .
H18B H 0.285371 0.325948 -0.084779 0.042 Uiso 1 1 calc R U .
H18C H 0.185992 0.377327 -0.220062 0.042 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
V V 0.3005 0.5294
;
International Tables for Crystallography
(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 V1 N1 111.81(19) 2_656 .
N1 V1 CL1 124.09(10) 2_656 .
N1 V1 CL1 124.09(10) . .
N1 V1 P1 96.37(11) 2_656 .
N1 V1 P1 92.06(11) . .
CL1 V1 P1 82.47(3) . .
N1 V1 P1 92.06(11) 2_656 2_656
N1 V1 P1 96.37(11) . 2_656
CL1 V1 P1 82.47(3) . 2_656
P1 V1 P1 164.94(5) . 2_656
N2 V2 N2 111.7(2) 2_655 .
N2 V2 CL2 124.17(10) 2_655 .
N2 V2 CL2 124.17(10) . .
N2 V2 P2 91.17(10) 2_655 2_655
N2 V2 P2 96.06(10) . 2_655
CL2 V2 P2 83.57(3) . 2_655
N2 V2 P2 96.06(10) 2_655 .
N2 V2 P2 91.17(10) . .
CL2 V2 P2 83.57(3) . .
P2 V2 P2 167.14(5) 2_655 .
C7 P1 C9 103.7(2) . .
C7 P1 C8 102.89(19) . .
C9 P1 C8 104.76(18) . .
C7 P1 V1 116.04(13) . .
C9 P1 V1 110.93(13) . .
C8 P1 V1 117.04(13) . .
C17 P2 C16 102.9(2) . .
C17 P2 C18 104.4(2) . .
C16 P2 C18 103.41(18) . .
C17 P2 V2 115.03(13) . .
C16 P2 V2 118.40(12) . .
C18 P2 V2 111.15(14) . .
C1 N1 V1 160.8(2) . .
C10 N2 V2 161.2(3) . .
N1 C1 C2 121.4(3) . .
N1 C1 C6 120.5(3) . .
C2 C1 C6 118.2(3) . .
C3 C2 C1 120.7(3) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 120.3(4) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 119.5(3) . .
C5 C4 H4 120.2 . .
C3 C4 H4 120.2 . .
C4 C5 C6 120.9(3) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C5 C6 C1 120.5(3) . .
C5 C6 H6 119.8 . .
C1 C6 H6 119.8 . .
P1 C7 H7A 109.5 . .
P1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
P1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
P1 C8 H8A 109.5 . .
P1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
P1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
P1 C9 H9A 109.5 . .
P1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
P1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N2 C10 C15 121.5(3) . .
N2 C10 C11 120.8(3) . .
C15 C10 C11 117.7(3) . .
C12 C11 C10 120.2(4) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C13 C12 C11 121.3(4) . .
C13 C12 H12 119.4 . .
C11 C12 H12 119.4 . .
C12 C13 C14 118.9(4) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
C15 C14 C13 120.3(4) . .
C15 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
C14 C15 C10 121.5(4) . .
C14 C15 H15 119.2 . .
C10 C15 H15 119.2 . .
P2 C16 H16A 109.5 . .
P2 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
P2 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
P2 C17 H17A 109.5 . .
P2 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
P2 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
P2 C18 H18A 109.5 . .
P2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
P2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
V1 N1 1.702(3) 2_656
V1 N1 1.702(3) .
V1 CL1 2.4265(17) .
V1 P1 2.4533(14) .
V1 P1 2.4534(14) 2_656
V2 N2 1.700(3) 2_655
V2 N2 1.700(3) .
V2 CL2 2.4191(17) .
V2 P2 2.4646(18) 2_655
V2 P2 2.4646(18) .
P1 C7 1.815(4) .
P1 C9 1.816(4) .
P1 C8 1.817(4) .
P2 C17 1.810(4) .
P2 C16 1.815(4) .
P2 C18 1.817(4) .
N1 C1 1.387(4) .
N2 C10 1.383(4) .
C1 C2 1.399(5) .
C1 C6 1.406(5) .
C2 C3 1.387(5) .
C2 H2 0.9500 .
C3 C4 1.390(6) .
C3 H3 0.9500 .
C4 C5 1.377(6) .
C4 H4 0.9500 .
C5 C6 1.381(5) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C15 1.398(5) .
C10 C11 1.406(5) .
C11 C12 1.385(5) .
C11 H11 0.9500 .
C12 C13 1.381(6) .
C12 H12 0.9500 .
C13 C14 1.390(6) .
C13 H13 0.9500 .
C14 C15 1.376(5) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 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
N1 V1 N1 C1 5.6(7) 2_656
CL1 V1 N1 C1 -174.4(7) .
P1 V1 N1 C1 -92.1(7) .
P1 V1 N1 C1 100.4(7) 2_656
N2 V2 N2 C10 -12.0(7) 2_655
CL2 V2 N2 C10 168.0(7) .
P2 V2 N2 C10 -105.7(7) 2_655
P2 V2 N2 C10 85.0(7) .
V1 N1 C1 C2 -35.5(9) .
V1 N1 C1 C6 145.0(6) .
N1 C1 C2 C3 -178.3(3) .
C6 C1 C2 C3 1.2(5) .
C1 C2 C3 C4 -0.8(6) .
C2 C3 C4 C5 -0.5(6) .
C3 C4 C5 C6 1.4(6) .
C4 C5 C6 C1 -0.9(6) .
N1 C1 C6 C5 179.2(3) .
C2 C1 C6 C5 -0.4(5) .
V2 N2 C10 C15 -11.0(9) .
V2 N2 C10 C11 170.3(6) .
N2 C10 C11 C12 178.8(3) .
C15 C10 C11 C12 0.1(5) .
C10 C11 C12 C13 0.3(5) .
C11 C12 C13 C14 -0.4(6) .
C12 C13 C14 C15 0.1(6) .
C13 C14 C15 C10 0.3(6) .
N2 C10 C15 C14 -179.1(3) .
C11 C10 C15 C14 -0.4(5) .
