#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/64/7056417.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_7056417
loop_
_publ_author_name
'Laha, Joydev K.'
'Sharma, Shubhra'
'Bhimpuria, Rohan A.'
'Dayal, Neetu'
'Dubey, Gurudutt'
'Bharatam, Prasad. V.'
_publ_section_title
;
 Integration of Oxidative Arylation with Sulfonyl Migration: One-Pot
 Tandem Synthesis of Densely Functionalized (NH)-Pyrroles
;
_journal_issue                   17
_journal_name_full               'New J. Chem.'
_journal_page_first              8791
_journal_page_last               8803
_journal_paper_doi               10.1039/C7NJ01709J
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C19 H17 N O4 S'
_chemical_formula_weight         355.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-15 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                94.087(5)
_cell_angle_beta                 91.473(5)
_cell_angle_gamma                92.143(5)
_cell_formula_units_Z            2
_cell_length_a                   6.559(5)
_cell_length_b                   8.777(5)
_cell_length_c                   15.493(5)
_cell_measurement_reflns_used    4076
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.3
_cell_volume                     888.7(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11725
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_min         2.328
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7010
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0521P)²+0.2976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2674
_reflns_number_total             4076
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj01709j2.cif
_cod_data_source_block           shelx
_cod_database_code               7056417
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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.
;
#END Tags that were not found in dictionaries
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
S1 S 0.29223(9) -0.00866(6) 0.24529(4) 0.04933(19) Uani 1 1 d . .
O2 O 0.3939(3) 0.13490(16) 0.27232(12) 0.0647(5) Uani 1 1 d . .
O4 O 0.8403(3) -0.16215(18) 0.49917(11) 0.0626(5) Uani 1 1 d . .
N1 N 0.3849(3) -0.33480(19) 0.39884(11) 0.0436(4) Uani 1 1 d . .
H1 H 0.3674 -0.4235 0.4184 0.052 Uiso 1 1 calc R U
O1 O 0.0781(2) -0.01084(17) 0.22480(12) 0.0614(5) Uani 1 1 d . .
C7 C 0.0964(3) -0.3748(2) 0.29517(13) 0.0387(5) Uani 1 1 d . .
O3 O 0.6986(3) -0.3892(2) 0.52167(12) 0.0756(6) Uani 1 1 d . .
C1 C 0.2653(3) -0.2794(2) 0.33666(13) 0.0398(5) Uani 1 1 d . .
C13 C 0.4161(3) -0.0884(2) 0.15457(15) 0.0491(5) Uani 1 1 d . .
C5 C 0.6955(4) -0.2699(3) 0.48795(14) 0.0505(6) Uani 1 1 d . .
C2 C 0.3450(3) -0.1317(2) 0.32555(14) 0.0435(5) Uani 1 1 d . .
C12 C 0.1204(3) -0.5301(2) 0.27657(14) 0.0473(5) Uani 1 1 d . .
H12 H 0.2451 -0.5723 0.2885 0.057 Uiso 1 1 calc R U
C14 C 0.6148(4) -0.0408(3) 0.13998(18) 0.0620(7) Uani 1 1 d . .
H14 H 0.6805 0.0352 0.1766 0.074 Uiso 1 1 calc R U
C18 C 0.3187(4) -0.2006(3) 0.10005(17) 0.0618(7) Uani 1 1 d . .
H18 H 0.1849 -0.2325 0.1095 0.074 Uiso 1 1 calc R U
C9 C -0.2484(4) -0.4075(3) 0.23940(17) 0.0600(6) Uani 1 1 d . .
H9 H -0.3727 -0.3658 0.2263 0.072 Uiso 1 1 calc R U
C8 C -0.0911(3) -0.3146(2) 0.27558(16) 0.0517(6) Uani 1 1 d . .
H8 H -0.1101 -0.2107 0.2871 0.062 Uiso 1 1 calc R U
C4 C 0.5376(3) -0.2304(2) 0.42634(14) 0.0456(5) Uani 1 1 d . .
C6 C 1.0119(4) -0.1926(3) 0.55531(18) 0.0757(8) Uani 1 1 d . .
H6A H 1.1075 -0.1068 0.5587 0.114 Uiso 1 1 calc R U
H6B H 0.9643 -0.2092 0.6121 0.114 Uiso 1 1 calc R U
H6C H 1.0774 -0.2821 0.5323 0.114 Uiso 1 1 calc R U
C3 C 0.5149(3) -0.1035(2) 0.38171(14) 0.0478(5) Uani 1 1 d . .
H3 H 0.5972 -0.0145 0.3875 0.057 Uiso 1 1 calc R U
C11 C -0.0392(4) -0.6225(3) 0.24061(15) 0.0565(6) Uani 1 1 d . .
H11 H -0.0216 -0.7264 0.2287 0.068 Uiso 1 1 calc R U
C16 C 0.6216(5) -0.2203(4) 0.01568(18) 0.0728(8) Uani 1 1 d . .
C10 C -0.2242(4) -0.5615(3) 0.22240(17) 0.0604(6) Uani 1 1 d . .
H10 H -0.3321 -0.6240 0.1988 0.072 Uiso 1 1 calc R U
C17 C 0.4225(5) -0.2650(3) 0.03125(18) 0.0765(8) Uani 1 1 d . .
H17 H 0.3568 -0.3406 -0.0057 0.092 Uiso 1 1 calc R U
C15 C 0.7140(4) -0.1067(3) 0.0710(2) 0.0743(8) Uani 1 1 d . .
H15 H 0.8473 -0.0740 0.0611 0.089 Uiso 1 1 calc R U
C19 C 0.7355(6) -0.2929(4) -0.0585(2) 0.1100(13) Uani 1 1 d . .
H19A H 0.6484 -0.3691 -0.0900 0.165 Uiso 1 1 calc R U
H19B H 0.7765 -0.2161 -0.0964 0.165 Uiso 1 1 calc R U
H19C H 0.8541 -0.3398 -0.0366 0.165 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 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
O1 S1 O2 118.46(10)
O1 S1 C2 110.99(10)
O2 S1 C2 106.35(11)
O1 S1 C13 108.06(11)
O2 S1 C13 108.20(11)
C2 S1 C13 103.79(10)
C5 O4 C6 116.69(18)
C1 N1 C4 110.83(17)
C12 C7 C8 118.38(19)
C12 C7 C1 119.84(18)
C8 C7 C1 121.76(18)
N1 C1 C2 105.82(18)
N1 C1 C7 120.20(17)
C2 C1 C7 133.95(18)
C18 C13 C14 120.3(3)
C18 C13 S1 120.4(2)
C14 C13 S1 119.28(19)
O3 C5 O4 123.7(2)
O3 C5 C4 124.5(2)
O4 C5 C4 111.73(19)
C3 C2 C1 108.11(18)
C3 C2 S1 120.72(16)
C1 C2 S1 130.04(17)
C11 C12 C7 120.6(2)
C15 C14 C13 119.3(3)
C13 C18 C17 119.1(3)
C8 C9 C10 120.8(2)
C9 C8 C7 120.4(2)
C3 C4 N1 107.81(18)
C3 C4 C5 131.5(2)
N1 C4 C5 120.55(19)
C4 C3 C2 107.41(18)
C10 C11 C12 120.3(2)
C15 C16 C17 117.8(3)
C15 C16 C19 120.7(3)
C17 C16 C19 121.5(3)
C9 C10 C11 119.5(2)
C18 C17 C16 121.7(3)
C14 C15 C16 121.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4310(19)
S1 O2 1.4337(17)
S1 C2 1.740(2)
S1 C13 1.757(3)
O4 C5 1.314(3)
O4 C6 1.449(3)
N1 C1 1.355(3)
N1 C4 1.370(3)
C7 C12 1.389(3)
C7 C8 1.392(3)
C7 C1 1.469(3)
O3 C5 1.204(3)
C1 C2 1.404(3)
C13 C18 1.378(3)
C13 C14 1.383(3)
C5 C4 1.458(3)
C2 C3 1.400(3)
C12 C11 1.381(3)
C14 C15 1.370(4)
C18 C17 1.378(4)
C9 C8 1.373(3)
C9 C10 1.374(3)
C4 C3 1.363(3)
C11 C10 1.375(3)
C16 C15 1.378(4)
C16 C17 1.382(4)
C16 C19 1.504(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139177986
