#------------------------------------------------------------------------------
#$Date: 2022-08-31 00:57:16 +0300 (Wed, 31 Aug 2022) $
#$Revision: 277468 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130619.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_7130619
loop_
_publ_author_name
'Saha, Shuvendu'
'Maji, Modhu Sudan'
_publ_section_title
;
 Cp*Co(III)-catalyzed thiocarbamate directed C−H
 aminocarbonyl-ation, amination, and cascade annulation of pyrroles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03992C
_journal_year                    2022
_chemical_formula_moiety         'C14 H15 N3 O S'
_chemical_formula_sum            'C14 H15 N3 O S'
_chemical_formula_weight         273.35
_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_date             2021-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-02 deposited with the CCDC.	2022-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                91.97(2)
_cell_angle_beta                 97.090(12)
_cell_angle_gamma                103.993(18)
_cell_formula_units_Z            4
_cell_length_a                   9.831(4)
_cell_length_b                   9.988(7)
_cell_length_c                   14.908(7)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.666
_cell_measurement_theta_min      2.396
_cell_volume                     1406.4(13)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27171
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.747
_diffrn_reflns_theta_min         2.396
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1199 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.9494.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0473
_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)+(0.0634P)²+0.6768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4573
_reflns_number_total             5968
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03992c2.cif
_cod_data_source_block           SSH-778
_cod_original_cell_volume        1406.3(13)
_cod_database_code               7130619
_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_max   0.990
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N2(H2), C4(H4), C18(H18), C11(H11), C21(H21), C17(H17), C25(H25),
 C16(H16), C7(H7), C9(H9), C8(H8), C2(H2A), C3(H3), C10(H10), C22(H22),
 C23(H23), C24(H24)
;
_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
S2 S -0.12992(7) 0.73861(6) 0.51051(4) 0.05693(18) Uani 1 1 d . . . . .
S1 S 0.37021(7) 0.42897(6) 0.81870(4) 0.05888(19) Uani 1 1 d . . . . .
N1 N 0.52681(19) 0.68911(18) 0.84922(11) 0.0449(4) Uani 1 1 d . . . . .
O2 O 0.2984(2) 0.79417(19) 0.59166(13) 0.0687(5) Uani 1 1 d . . . . .
N4 N 0.03542(18) 0.84397(18) 0.66525(11) 0.0443(4) Uani 1 1 d . . . . .
N5 N 0.18458(19) 0.96052(18) 0.55945(12) 0.0473(4) Uani 1 1 d . . . . .
H5 H 0.166794 1.020180 0.520359 0.057 Uiso 1 1 calc R . . . .
O1 O 0.77844(19) 0.5722(2) 0.82841(12) 0.0684(5) Uani 1 1 d . . . . .
N3 N 0.48858(19) 0.6008(2) 0.70126(12) 0.0487(4) Uani 1 1 d . . . . .
N2 N 0.66877(19) 0.57655(19) 0.95248(12) 0.0487(4) Uani 1 1 d . . . . .
H2 H 0.647992 0.537295 1.002666 0.058 Uiso 1 1 calc R . . . .
N6 N -0.0240(2) 0.60695(19) 0.64332(14) 0.0530(5) Uani 1 1 d . . . . .
C26 C -0.0363(2) 0.7244(2) 0.60873(14) 0.0429(4) Uani 1 1 d . . . . .
C6 C 0.8066(2) 0.4077(2) 0.93594(14) 0.0466(5) Uani 1 1 d . . . . .
C12 C 0.4658(2) 0.5751(2) 0.78554(13) 0.0435(5) Uani 1 1 d . . . . .
C20 C 0.3017(2) 0.8746(2) 0.44406(15) 0.0465(5) Uani 1 1 d . . . . .
C15 C 0.1307(2) 0.9593(2) 0.64221(15) 0.0459(5) Uani 1 1 d . . . . .
C19 C 0.2633(2) 0.8729(2) 0.53742(16) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.6169(2) 0.6906(2) 0.92882(14) 0.0477(5) Uani 1 1 d . . . . .
C5 C 0.7506(2) 0.5240(2) 0.90037(14) 0.0490(5) Uani 1 1 d . . . . .
C4 C 0.4983(3) 0.8178(2) 0.84339(16) 0.0544(5) Uani 1 1 d . . . . .
H4 H 0.440090 0.845213 0.795377 0.065 Uiso 1 1 calc R . . . .
C18 C 0.0049(3) 0.8700(3) 0.75146(15) 0.0544(5) Uani 1 1 d . . . . .
H18 H -0.056911 0.807897 0.784088 0.065 Uiso 1 1 calc R . . . .
C11 C 0.7505(3) 0.3254(3) 1.00182(17) 0.0590(6) Uani 1 1 d . . . . .
H11 H 0.669174 0.339602 1.025360 0.071 Uiso 1 1 calc R . . . .
C21 C 0.2187(3) 0.9092(3) 0.37099(17) 0.0605(6) Uani 1 1 d . . . . .
H21 H 0.136687 0.939577 0.379987 0.073 Uiso 1 1 calc R . . . .
C17 C 0.0789(3) 0.9994(3) 0.78068(17) 0.0645(7) Uani 1 1 d . . . . .
H17 H 0.076753 1.045169 0.837235 0.077 Uiso 1 1 calc R . . . .
C25 C 0.4213(3) 0.8314(3) 0.42929(18) 0.0616(6) Uani 1 1 d . . . . .
H25 H 0.478913 0.807341 0.478999 0.074 Uiso 1 1 calc R . . . .
C16 C 0.1602(3) 1.0554(3) 0.71271(18) 0.0610(6) Uani 1 1 d . . . . .
H16 H 0.223819 1.144214 0.715969 0.073 Uiso 1 1 calc R . . . .
C7 C 0.9230(3) 0.3818(3) 0.90191(17) 0.0608(6) Uani 1 1 d . . . . .
H7 H 0.961081 0.435348 0.855253 0.073 Uiso 1 1 calc R . . . .
C14 C 0.4138(3) 0.5043(3) 0.62571(16) 0.0707(7) Uani 1 1 d . . . . .
H14A H 0.443791 0.539871 0.568968 0.106 Uiso 1 1 calc R . . . .
H14B H 0.435577 0.414348 0.633627 0.106 Uiso 1 1 calc R . . . .
H14C H 0.311695 0.493580 0.623634 0.106 Uiso 1 1 calc R . . . .
C13 C 0.5977(3) 0.7172(3) 0.67711(17) 0.0639(7) Uani 1 1 d . . . . .
H13A H 0.594703 0.715087 0.611109 0.096 Uiso 1 1 calc R . . . .
H13B H 0.580265 0.804352 0.699067 0.096 Uiso 1 1 calc R . . . .
H13C H 0.691078 0.710001 0.705025 0.096 Uiso 1 1 calc R . . . .
C9 C 0.9295(3) 0.2008(3) 1.0001(2) 0.0686(7) Uani 1 1 d . . . . .
H9 H 0.971950 0.130553 1.022677 0.082 Uiso 1 1 calc R . . . .
C8 C 0.9852(3) 0.2798(3) 0.9344(2) 0.0673(7) Uani 1 1 d . . . . .
H8 H 1.066292 0.264769 0.911012 0.081 Uiso 1 1 calc R . . . .
C2 C 0.6428(3) 0.8184(3) 0.97135(17) 0.0634(6) Uani 1 1 d . . . . .
H2A H 0.701484 0.849176 1.027379 0.076 Uiso 1 1 calc R . . . .
C27 C 0.0858(3) 0.5995(3) 0.7172(2) 0.0738(8) Uani 1 1 d . . . . .
H27A H 0.075469 0.503084 0.732139 0.111 Uiso 1 1 calc R . . . .
H27B H 0.179212 0.635518 0.698492 0.111 Uiso 1 1 calc R . . . .
H27C H 0.076489 0.654953 0.770591 0.111 Uiso 1 1 calc R . . . .
C3 C 0.5676(3) 0.8976(3) 0.91796(18) 0.0649(7) Uani 1 1 d . . . . .
H3 H 0.565919 0.990672 0.931950 0.078 Uiso 1 1 calc R . . . .
C10 C 0.8126(3) 0.2224(3) 1.0335(2) 0.0707(7) Uani 1 1 d . . . . .
H10 H 0.773605 0.166457 1.078869 0.085 Uiso 1 1 calc R . . . .
C28 C -0.1153(3) 0.4744(3) 0.6044(2) 0.0787(8) Uani 1 1 d . . . . .
H28A H -0.091039 0.399420 0.638646 0.118 Uiso 1 1 calc R . . . .
H28B H -0.214381 0.473973 0.607575 0.118 Uiso 1 1 calc R . . . .
H28C H -0.101625 0.460990 0.541049 0.118 Uiso 1 1 calc R . . . .
C22 C 0.2556(4) 0.8994(3) 0.28444(19) 0.0756(8) Uani 1 1 d . . . . .
H22 H 0.198409 0.923354 0.234466 0.091 Uiso 1 1 calc R . . . .
C23 C 0.3731(4) 0.8557(3) 0.2703(2) 0.0754(8) Uani 1 1 d . . . . .
H23 H 0.396442 0.847795 0.210659 0.090 Uiso 1 1 calc R . . . .
C24 C 0.4577(3) 0.8230(3) 0.3430(2) 0.0742(8) Uani 1 1 d . . . . .
H24 H 0.540788 0.794818 0.333724 0.089 Uiso 1 1 calc R . . . .
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'
S S 0.1246 0.1234 '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 N1 C12 127.19(18) . . ?
C4 N1 C12 124.23(18) . . ?
C4 N1 C1 108.49(18) . . ?
C15 N4 C26 127.56(18) . . ?
C15 N4 C18 108.50(18) . . ?
C18 N4 C26 123.46(18) . . ?
C15 N5 H5 118.8 . . ?
C19 N5 H5 118.8 . . ?
C19 N5 C15 122.31(18) . . ?
C12 N3 C14 120.8(2) . . ?
C12 N3 C13 124.09(19) . . ?
C14 N3 C13 114.9(2) . . ?
C1 N2 H2 119.0 . . ?
C5 N2 H2 119.0 . . ?
C5 N2 C1 122.09(19) . . ?
C26 N6 C27 123.1(2) . . ?
C26 N6 C28 120.9(2) . . ?
C27 N6 C28 115.8(2) . . ?
N4 C26 S2 120.42(15) . . ?
N6 C26 S2 125.63(17) . . ?
N6 C26 N4 113.91(19) . . ?
C11 C6 C5 123.9(2) . . ?
C7 C6 C5 117.9(2) . . ?
C7 C6 C11 118.2(2) . . ?
N1 C12 S1 120.17(15) . . ?
N3 C12 S1 126.01(17) . . ?
N3 C12 N1 113.76(19) . . ?
C21 C20 C19 122.8(2) . . ?
C21 C20 C25 119.0(2) . . ?
C25 C20 C19 118.1(2) . . ?
N4 C15 N5 121.04(18) . . ?
C16 C15 N4 108.0(2) . . ?
C16 C15 N5 130.9(2) . . ?
O2 C19 N5 121.3(2) . . ?
O2 C19 C20 121.7(2) . . ?
N5 C19 C20 117.05(18) . . ?
N1 C1 N2 122.11(19) . . ?
C2 C1 N1 107.4(2) . . ?
C2 C1 N2 130.5(2) . . ?
O1 C5 N2 121.4(2) . . ?
O1 C5 C6 121.8(2) . . ?
N2 C5 C6 116.84(19) . . ?
N1 C4 H4 126.0 . . ?
C3 C4 N1 108.0(2) . . ?
C3 C4 H4 126.0 . . ?
N4 C18 H18 126.2 . . ?
C17 C18 N4 107.6(2) . . ?
C17 C18 H18 126.2 . . ?
C6 C11 H11 119.9 . . ?
C6 C11 C10 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C18 C17 H17 125.9 . . ?
C18 C17 C16 108.3(2) . . ?
C16 C17 H17 125.9 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.7(3) . . ?
C24 C25 H25 119.6 . . ?
C15 C16 C17 107.5(2) . . ?
C15 C16 H16 126.2 . . ?
C17 C16 H16 126.2 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C1 C2 H2A 125.9 . . ?
C1 C2 C3 108.2(2) . . ?
C3 C2 H2A 125.9 . . ?
N6 C27 H27A 109.5 . . ?
N6 C27 H27B 109.5 . . ?
N6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C4 C3 C2 107.9(2) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.7 . . ?
N6 C28 H28A 109.5 . . ?
N6 C28 H28B 109.5 . . ?
N6 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.7(3) . . ?
C24 C23 H23 120.2 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24 120.0 . . ?
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
S2 C26 1.660(2) . ?
S1 C12 1.661(2) . ?
N1 C12 1.418(3) . ?
N1 C1 1.388(3) . ?
N1 C4 1.384(3) . ?
O2 C19 1.223(3) . ?
N4 C26 1.418(3) . ?
N4 C15 1.381(3) . ?
N4 C18 1.385(3) . ?
N5 H5 0.8800 . ?
N5 C15 1.401(3) . ?
N5 C19 1.358(3) . ?
O1 C5 1.225(3) . ?
N3 C12 1.326(3) . ?
N3 C14 1.455(3) . ?
N3 C13 1.468(3) . ?
N2 H2 0.8800 . ?
N2 C1 1.395(3) . ?
N2 C5 1.362(3) . ?
N6 C26 1.323(3) . ?
N6 C27 1.461(3) . ?
N6 C28 1.462(3) . ?
C6 C5 1.489(3) . ?
C6 C11 1.384(3) . ?
C6 C7 1.382(3) . ?
C20 C19 1.486(3) . ?
C20 C21 1.384(3) . ?
C20 C25 1.385(3) . ?
C15 C16 1.353(3) . ?
C1 C2 1.358(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.351(4) . ?
C18 H18 0.9500 . ?
C18 C17 1.348(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.414(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.382(4) . ?
C16 H16 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.381(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C8 1.364(4) . ?
C9 C10 1.368(4) . ?
C8 H8 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.409(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.366(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(4) . ?
C24 H24 0.9500 . ?
