#------------------------------------------------------------------------------
#$Date: 2023-01-06 11:54:26 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/20/7062073.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_7062073
loop_
_publ_author_name
'Mangali, Rofin'
'Muthusamy, Sengodagounder'
_publ_section_title
;
 BF3·OEt2 catalyzed S--H insertion reactions of α-diazo imidamides
 and enolizable thioamides under metal-free conditions
;
_journal_issue                   48
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              23173
_journal_page_last               23178
_journal_paper_doi               10.1039/D2NJ04964C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C26 H27 N5 O2 S2, 3.5[H2O]'
_chemical_formula_sum            'C27 H35 N5 O7.5 S2'
_chemical_formula_weight         613.72
_chemical_name_systematic        'Substituted indole'
_chemical_properties_physical    Moisture-sensitive
_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   mixed
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-06-19 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                97.380(3)
_cell_angle_beta                 112.378(2)
_cell_angle_gamma                103.183(3)
_cell_formula_units_Z            2
_cell_length_a                   11.3439(9)
_cell_length_b                   11.8482(9)
_cell_length_c                   12.3204(9)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.7149
_cell_measurement_theta_min      2.2571
_cell_volume                     1447.6(2)
_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      301.78
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            40102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.284
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and hexane'
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0385
_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)+(0.0475P)²+0.4998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4019
_reflns_number_total             5111
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj04964c2.cif
_cod_data_source_block           smrm121_0m_a
_cod_depositor_comments          'Adding full bibliography for 7062073.cif.'
_cod_original_cell_volume        1447.62(19)
_cod_original_formula_sum        'C27 H35 N5 O7.50 S2'
_cod_database_code               7062073
_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   0.973
_shelx_estimated_absorpt_t_min   0.951
_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 Aromatic/amide H refined with riding coordinates:
 N5(H5), C2(H2A), C3(H3), C4(H4), C5(H5A), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
S1 S 0.47260(5) 0.39999(4) 0.17405(5) 0.04309(15) Uani 1 1 d . . . . .
S2 S 0.06287(5) 0.25986(5) -0.02836(5) 0.04869(16) Uani 1 1 d . . . . .
O1 O -0.00629(16) 0.32772(15) -0.10279(14) 0.0648(5) Uani 1 1 d . . . . .
O2 O -0.00396(16) 0.13964(14) -0.03628(16) 0.0641(4) Uani 1 1 d . . . . .
N1 N 0.25288(16) 0.07858(14) -0.03121(14) 0.0410(4) Uani 1 1 d . . . . .
N2 N 0.18808(18) 0.25581(16) -0.06407(15) 0.0427(4) Uani 1 1 d . . . . .
N3 N 0.66976(17) 0.55953(14) 0.15481(15) 0.0455(4) Uani 1 1 d . . . . .
N4 N 0.63821(17) 0.62551(15) 0.23669(15) 0.0463(4) Uani 1 1 d . . . . .
N5 N 0.61198(18) 0.36920(15) 0.04417(16) 0.0485(4) Uani 1 1 d . . . . .
H5 H 0.562851 0.296208 0.023880 0.058 Uiso 1 1 calc R . . . .
C1 C 0.3567(2) 0.04765(17) 0.04892(17) 0.0401(5) Uani 1 1 d . . . . .
C2 C 0.3744(2) -0.06435(19) 0.0553(2) 0.0506(5) Uani 1 1 d . . . . .
H2A H 0.311733 -0.133192 -0.000821 0.061 Uiso 1 1 calc R . . . .
C3 C 0.4869(3) -0.0692(2) 0.1470(2) 0.0570(6) Uani 1 1 d . . . . .
H3 H 0.500833 -0.142907 0.153453 0.068 Uiso 1 1 calc R . . . .
C4 C 0.5815(2) 0.0335(2) 0.2310(2) 0.0567(6) Uani 1 1 d . . . . .
H4 H 0.656922 0.026989 0.292665 0.068 Uiso 1 1 calc R . . . .
C5 C 0.5655(2) 0.1442(2) 0.22448(19) 0.0489(5) Uani 1 1 d . . . . .
H5A H 0.629395 0.212408 0.280741 0.059 Uiso 1 1 calc R . . . .
C6 C 0.45194(19) 0.15231(17) 0.13206(17) 0.0395(4) Uani 1 1 d . . . . .
C7 C 0.40262(19) 0.24942(17) 0.09827(17) 0.0384(4) Uani 1 1 d . . . . .
C8 C 0.28114(19) 0.20007(16) -0.00018(17) 0.0379(4) Uani 1 1 d . . . . .
C9 C 0.59496(19) 0.44882(17) 0.11896(17) 0.0396(4) Uani 1 1 d . . . . .
C10 C 0.7263(2) 0.72364(18) 0.29835(18) 0.0472(5) Uani 1 1 d . . . . .
H10 H 0.802257 0.745460 0.284100 0.057 Uiso 1 1 calc R . . . .
C11 C 0.7146(2) 0.80439(18) 0.39089(18) 0.0440(5) Uani 1 1 d . . . . .
C12 C 0.8247(2) 0.8998(2) 0.4678(2) 0.0586(6) Uani 1 1 d . . . . .
H12 H 0.902964 0.913191 0.456809 0.070 Uiso 1 1 calc R . . . .
C13 C 0.8206(2) 0.9752(2) 0.5602(2) 0.0632(7) Uani 1 1 d . . . . .
H13 H 0.896512 1.038090 0.610809 0.076 Uiso 1 1 calc R . . . .
C14 C 0.7070(2) 0.9594(2) 0.5791(2) 0.0568(6) Uani 1 1 d . . . . .
C15 C 0.5965(2) 0.8651(2) 0.5010(2) 0.0598(6) Uani 1 1 d . . . . .
H15 H 0.517799 0.853019 0.511105 0.072 Uiso 1 1 calc R . . . .
C16 C 0.5994(2) 0.7886(2) 0.40877(19) 0.0517(5) Uani 1 1 d . . . . .
H16 H 0.523328 0.725799 0.358137 0.062 Uiso 1 1 calc R . . . .
C17 C 0.7037(3) 1.0411(3) 0.6812(3) 0.0875(9) Uani 1 1 d . . . . .
H17A H 0.743458 1.122534 0.683204 0.131 Uiso 1 1 calc GR . . . .
H17B H 0.752821 1.023469 0.756381 0.131 Uiso 1 1 calc GR . . . .
H17C H 0.612646 1.029572 0.669349 0.131 Uiso 1 1 calc GR . . . .
C18 C 0.1331(2) 0.3377(2) 0.12367(19) 0.0470(5) Uani 1 1 d . . . . .
C19 C 0.1875(2) 0.2809(2) 0.2134(2) 0.0563(6) Uani 1 1 d . . . . .
H19 H 0.180713 0.200483 0.193956 0.068 Uiso 1 1 calc R . . . .
C20 C 0.2518(3) 0.3455(3) 0.3319(2) 0.0658(7) Uani 1 1 d . . . . .
H20 H 0.289466 0.307873 0.392261 0.079 Uiso 1 1 calc R . . . .
C21 C 0.2620(2) 0.4649(3) 0.3636(2) 0.0667(7) Uani 1 1 d . . . . .
C22 C 0.2024(2) 0.5183(2) 0.2719(2) 0.0623(6) Uani 1 1 d . . . . .
H22 H 0.205606 0.597786 0.291310 0.075 Uiso 1 1 calc R . . . .
C23 C 0.1387(2) 0.4555(2) 0.1529(2) 0.0529(6) Uani 1 1 d . . . . .
H23 H 0.099465 0.492524 0.092500 0.064 Uiso 1 1 calc R . . . .
C24 C 0.3349(3) 0.5347(3) 0.4932(2) 0.0991(11) Uani 1 1 d . . . . .
H24A H 0.279885 0.576784 0.512826 0.149 Uiso 1 1 calc GR . . . .
H24B H 0.416847 0.590889 0.504620 0.149 Uiso 1 1 calc GR . . . .
H24C H 0.354420 0.481009 0.544983 0.149 Uiso 1 1 calc GR . . . .
C25 C 0.1401(2) -0.00478(19) -0.13648(19) 0.0547(6) Uani 1 1 d . . . . .
H25A H 0.092330 0.038978 -0.188430 0.082 Uiso 1 1 calc GR . . . .
H25B H 0.081394 -0.054368 -0.110632 0.082 Uiso 1 1 calc GR . . . .
H25C H 0.172403 -0.053837 -0.179708 0.082 Uiso 1 1 calc GR . . . .
C26 C 0.7090(3) 0.3999(2) -0.0043(2) 0.0620(6) Uani 1 1 d . . . . .
H26A H 0.713630 0.328364 -0.046752 0.093 Uiso 1 1 calc GR . . . .
H26B H 0.795102 0.441899 0.060574 0.093 Uiso 1 1 calc GR . . . .
H26C H 0.683063 0.449834 -0.058948 0.093 Uiso 1 1 calc GR . . . .
H2 H 0.221(2) 0.316(2) -0.079(2) 0.055(7) Uiso 1 1 d . . . . .
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
C7 S1 C9 101.67(9) . . ?
O1 S2 N2 105.16(10) . . ?
O1 S2 C18 109.36(10) . . ?
O2 S2 O1 120.44(10) . . ?
O2 S2 N2 106.53(10) . . ?
O2 S2 C18 107.66(10) . . ?
N2 S2 C18 106.94(9) . . ?
C1 N1 C25 124.56(17) . . ?
C8 N1 C1 108.17(16) . . ?
C8 N1 C25 127.04(17) . . ?
S2 N2 H2 114.5(17) . . ?
C8 N2 S2 119.07(14) . . ?
C8 N2 H2 114.2(17) . . ?
C9 N3 N4 110.68(17) . . ?
C10 N4 N3 114.32(18) . . ?
C9 N5 H5 118.5 . . ?
C9 N5 C26 122.91(18) . . ?
C26 N5 H5 118.5 . . ?
N1 C1 C2 129.97(19) . . ?
N1 C1 C6 108.42(17) . . ?
C2 C1 C6 121.61(19) . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2A 121.2 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5A 120.7 . . ?
C4 C5 C6 118.7(2) . . ?
C6 C5 H5A 120.7 . . ?
C1 C6 C7 106.61(17) . . ?
C5 C6 C1 119.40(19) . . ?
C5 C6 C7 133.99(19) . . ?
C6 C7 S1 127.51(15) . . ?
C8 C7 S1 125.65(15) . . ?
C8 C7 C6 106.58(17) . . ?
N1 C8 N2 120.23(17) . . ?
N1 C8 C7 110.21(17) . . ?
C7 C8 N2 129.51(18) . . ?
N3 C9 S1 120.51(16) . . ?
N3 C9 N5 120.60(19) . . ?
N5 C9 S1 118.84(14) . . ?
N4 C10 H10 118.5 . . ?
N4 C10 C11 123.0(2) . . ?
C11 C10 H10 118.5 . . ?
C12 C11 C10 119.1(2) . . ?
C16 C11 C10 123.22(19) . . ?
C16 C11 C12 117.6(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 117.2(2) . . ?
C13 C14 C17 121.1(2) . . ?
C15 C14 C17 121.7(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 H15 119.0 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 S2 119.31(18) . . ?
C23 C18 S2 120.15(16) . . ?
C23 C18 C19 120.5(2) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.9(2) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 H20 119.1 . . ?
C19 C20 C21 121.8(2) . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C22 117.9(2) . . ?
C20 C21 C24 121.1(3) . . ?
C22 C21 C24 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.5 . . ?
C18 C23 H23 120.1 . . ?
C22 C23 C18 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N5 C26 H26A 109.5 . . ?
N5 C26 H26B 109.5 . . ?
N5 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
S1 C7 1.7454(19) . ?
S1 C9 1.782(2) . ?
S2 O1 1.4255(15) . ?
S2 O2 1.4243(16) . ?
S2 N2 1.6477(19) . ?
S2 C18 1.755(2) . ?
N1 C1 1.378(2) . ?
N1 C8 1.370(2) . ?
N1 C25 1.458(3) . ?
N2 C8 1.410(3) . ?
N2 H2 0.80(2) . ?
N3 N4 1.399(2) . ?
N3 C9 1.301(2) . ?
N4 C10 1.262(3) . ?
N5 H5 0.8600 . ?
N5 C9 1.331(3) . ?
N5 C26 1.440(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.405(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.364(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(3) . ?
C5 H5A 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C7 1.432(3) . ?
C7 C8 1.375(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.458(3) . ?
C11 C12 1.384(3) . ?
C11 C16 1.382(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(3) . ?
C14 C15 1.382(3) . ?
C14 C17 1.504(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.385(3) . ?
C18 C23 1.377(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(4) . ?
C21 C22 1.389(3) . ?
C21 C24 1.504(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(3) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 268.7 75.7 '3.5 H2O'
