#------------------------------------------------------------------------------
#$Date: 2021-03-06 08:22:41 +0200 (Sat, 06 Mar 2021) $
#$Revision: 262795 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243775.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243775
loop_
_publ_author_name
'Kingsbury, Christopher J.'
'Sample, Harry C.'
'Senge, Mathias O.'
_publ_section_title
;
 Crystal structures of 4-bromo-2-formyl-1-tosyl-1H-pyrrole,
 (E)-4-bromo-2-(2-nitrovinyl)-1-tosyl-1H-pyrrole and
 6-(4-bromo-1-tosylpyrrol-2-yl)-4,4-dimethyl-5-nitrohexan-2-one
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              341
_journal_page_last               345
_journal_paper_doi               10.1107/S2056989021002280
_journal_volume                  77
_journal_year                    2021
_chemical_formula_moiety         'C13 H11 Br N2 O4 S'
_chemical_formula_sum            'C13 H11 Br N2 O4 S'
_chemical_formula_weight         371.21
_chemical_name_common            (E)-4-bromo-2-(2-nitrovinyl)-1-tosyl-1H-pyrrole
_chemical_name_systematic        (E)-4-bromo-2-(2-nitrovinyl)-1-tosyl-1H-pyrrole
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                83.423(3)
_cell_angle_beta                 80.393(3)
_cell_angle_gamma                85.693(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8904(4)
_cell_length_b                   8.3224(4)
_cell_length_c                   12.8763(7)
_cell_measurement_reflns_used    4853
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.50
_cell_volume                     722.06(7)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'shelXle (Hübschle, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7190
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         3.500
_exptl_absorpt_coefficient_mu    5.403
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.627
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0491
_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)+(0.1118P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1423
_reflns_number_gt                2378
_reflns_number_total             2617
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2036sup1.cif
_cod_data_source_block           2
_cod_database_code               2243775
_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   0.672
_shelx_estimated_absorpt_t_max   0.948
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.78111(5) 0.59378(4) 0.35381(3) 0.0425(2) Uani d 1 . .
N N1 0.6292(5) 0.7256(3) 0.6502(2) 0.0384(6) Uani d 1 . .
C C2 0.4649(5) 0.7946(4) 0.6072(3) 0.0358(7) Uani d 1 . .
C C3 0.4914(5) 0.7634(4) 0.5026(3) 0.0392(7) Uani d 1 . .
H H3 0.405169 0.797263 0.452898 0.047 Uiso calc 1 . .
C C4 0.6723(5) 0.6710(4) 0.4840(3) 0.0388(7) Uani d 1 . .
C C5 0.7544(6) 0.6478(4) 0.5740(3) 0.0397(7) Uani d 1 . .
H H5 0.875264 0.589067 0.582710 0.048 Uiso calc 1 . .
C C6 0.3020(5) 0.8827(4) 0.6651(3) 0.0381(7) Uani d 1 . .
H H6 0.306219 0.898197 0.736623 0.046 Uiso calc 1 . .
C C7 0.1474(6) 0.9425(5) 0.6225(3) 0.0437(8) Uani d 1 . .
H H7 0.141618 0.927123 0.551082 0.052 Uiso calc 1 . .
N N8 -0.0128(5) 1.0308(4) 0.6821(3) 0.0447(7) Uani d 1 . .
O O9 -0.0096(4) 1.0452(4) 0.7764(2) 0.0499(6) Uani d 1 . .
O O10 -0.1458(5) 1.0858(5) 0.6356(3) 0.0706(10) Uani d 1 . .
S S11 0.66335(12) 0.69881(8) 0.77875(6) 0.0366(2) Uani d 1 . .
O O12 0.5680(4) 0.8370(3) 0.8260(2) 0.0435(6) Uani d 1 . .
O O13 0.8708(4) 0.6635(3) 0.7737(2) 0.0429(6) Uani d 1 . .
C C14 0.5375(5) 0.5261(4) 0.8327(2) 0.0338(6) Uani d 1 . .
C C15 0.3465(6) 0.5434(4) 0.8867(3) 0.0469(8) Uani d 1 . .
H H15 0.283748 0.647790 0.895024 0.056 Uiso calc 1 . .
C C16 0.2498(6) 0.4049(5) 0.9280(3) 0.0503(9) Uani d 1 . .
H H16 0.118816 0.415207 0.964877 0.060 Uiso calc 1 . .
C C17 0.3389(6) 0.2510(4) 0.9171(3) 0.0408(7) Uani d 1 . .
C C18 0.5283(5) 0.2385(4) 0.8610(3) 0.0395(7) Uani d 1 . .
H H18 0.589695 0.134135 0.851045 0.047 Uiso calc 1 . .
C C19 0.6306(5) 0.3744(4) 0.8189(3) 0.0386(7) Uani d 1 . .
H H19 0.761277 0.364040 0.781580 0.046 Uiso calc 1 . .
C C20 0.2280(6) 0.1045(4) 0.9648(3) 0.0480(9) Uani d 1 . .
H H20A 0.123086 0.091657 0.924079 0.072 Uiso calc 1 . .
H H20B 0.169992 0.118266 1.038312 0.072 Uiso calc 1 . .
H H20C 0.318724 0.007925 0.963164 0.072 Uiso calc 1 . .
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'
Br Br -0.6763 1.2805 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C2 . . 109.1(3) ?
C5 N1 S11 . . 120.8(2) ?
C2 N1 S11 . . 129.0(2) ?
C3 C2 N1 . . 107.6(3) ?
C3 C2 C6 . . 128.1(3) ?
N1 C2 C6 . . 124.2(3) ?
C2 C3 C4 . . 106.5(3) ?
C2 C3 H3 . . 126.8 ?
C4 C3 H3 . . 126.8 ?
C5 C4 C3 . . 109.6(3) ?
C5 C4 Br1 . . 125.7(3) ?
C3 C4 Br1 . . 124.7(3) ?
C4 C5 N1 . . 107.2(3) ?
C4 C5 H5 . . 126.4 ?
N1 C5 H5 . . 126.4 ?
C7 C6 C2 . . 122.4(4) ?
C7 C6 H6 . . 118.8 ?
C2 C6 H6 . . 118.8 ?
C6 C7 N8 . . 121.2(4) ?
C6 C7 H7 . . 119.4 ?
N8 C7 H7 . . 119.4 ?
O10 N8 O9 . . 123.7(3) ?
O10 N8 C7 . . 116.7(3) ?
O9 N8 C7 . . 119.6(3) ?
O12 S11 O13 . . 121.14(15) ?
O12 S11 N1 . . 106.10(14) ?
O13 S11 N1 . . 104.39(15) ?
O12 S11 C14 . . 109.60(15) ?
O13 S11 C14 . . 109.53(15) ?
N1 S11 C14 . . 104.67(14) ?
C15 C14 C19 . . 121.5(3) ?
C15 C14 S11 . . 119.5(2) ?
C19 C14 S11 . . 119.0(3) ?
C16 C15 C14 . . 118.3(3) ?
C16 C15 H15 . . 120.8 ?
C14 C15 H15 . . 120.8 ?
C15 C16 C17 . . 121.9(4) ?
C15 C16 H16 . . 119.1 ?
C17 C16 H16 . . 119.1 ?
C18 C17 C16 . . 118.1(3) ?
C18 C17 C20 . . 122.2(3) ?
C16 C17 C20 . . 119.7(3) ?
C17 C18 C19 . . 121.7(3) ?
C17 C18 H18 . . 119.1 ?
C19 C18 H18 . . 119.1 ?
C18 C19 C14 . . 118.4(3) ?
C18 C19 H19 . . 120.8 ?
C14 C19 H19 . . 120.8 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4 . 1.881(3) ?
N1 C5 . 1.381(4) ?
N1 C2 . 1.399(4) ?
N1 S11 . 1.698(3) ?
C2 C3 . 1.381(5) ?
C2 C6 . 1.441(5) ?
C3 C4 . 1.414(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.361(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.318(6) ?
C6 H6 . 0.9500 ?
C7 N8 . 1.439(5) ?
C7 H7 . 0.9500 ?
N8 O10 . 1.210(5) ?
N8 O9 . 1.237(4) ?
S11 O12 . 1.428(2) ?
S11 O13 . 1.430(3) ?
S11 C14 . 1.748(3) ?
C14 C15 . 1.387(5) ?
C14 C19 . 1.389(4) ?
C15 C16 . 1.383(6) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.390(5) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.385(5) ?
C17 C20 . 1.503(5) ?
C18 C19 . 1.386(5) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 O10 2_576 0.95 2.37 3.297(5) 165.8 yes
C7 H7 O10 2_576 0.95 2.41 3.360(5) 173.8 yes
C6 H6 O12 . 0.95 2.29 2.963(4) 126.9 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 C3 . . . . -1.8(3) ?
S11 N1 C2 C3 . . . . -169.3(2) ?
C5 N1 C2 C6 . . . . 178.8(3) ?
S11 N1 C2 C6 . . . . 11.2(5) ?
N1 C2 C3 C4 . . . . 1.4(3) ?
C6 C2 C3 C4 . . . . -179.2(3) ?
C2 C3 C4 C5 . . . . -0.5(4) ?
C2 C3 C4 Br1 . . . . 179.7(2) ?
C3 C4 C5 N1 . . . . -0.5(4) ?
Br1 C4 C5 N1 . . . . 179.2(2) ?
C2 N1 C5 C4 . . . . 1.4(4) ?
S11 N1 C5 C4 . . . . 170.2(2) ?
C3 C2 C6 C7 . . . . 2.4(6) ?
N1 C2 C6 C7 . . . . -178.3(3) ?
C2 C6 C7 N8 . . . . -179.7(3) ?
C6 C7 N8 O10 . . . . 177.7(4) ?
C6 C7 N8 O9 . . . . -3.0(6) ?
C5 N1 S11 O12 . . . . 157.4(3) ?
C2 N1 S11 O12 . . . . -36.3(3) ?
C5 N1 S11 O13 . . . . 28.4(3) ?
C2 N1 S11 O13 . . . . -165.3(3) ?
C5 N1 S11 C14 . . . . -86.7(3) ?
C2 N1 S11 C14 . . . . 79.6(3) ?
O12 S11 C14 C15 . . . . 17.3(3) ?
O13 S11 C14 C15 . . . . 152.4(3) ?
N1 S11 C14 C15 . . . . -96.2(3) ?
O12 S11 C14 C19 . . . . -163.7(3) ?
O13 S11 C14 C19 . . . . -28.6(3) ?
N1 S11 C14 C19 . . . . 82.9(3) ?
C19 C14 C15 C16 . . . . 0.6(6) ?
S11 C14 C15 C16 . . . . 179.6(3) ?
C14 C15 C16 C17 . . . . 0.3(7) ?
C15 C16 C17 C18 . . . . -1.5(6) ?
C15 C16 C17 C20 . . . . 179.2(4) ?
C16 C17 C18 C19 . . . . 1.9(6) ?
C20 C17 C18 C19 . . . . -178.8(3) ?
C17 C18 C19 C14 . . . . -1.0(5) ?
C15 C14 C19 C18 . . . . -0.2(5) ?
S11 C14 C19 C18 . . . . -179.2(3) ?

_cod_database_fobs_code 2243775
