#------------------------------------------------------------------------------
#$Date: 2021-03-06 08:22:41 +0200 (Sat, 06 Mar 2021) $
#$Revision: 262795 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243776.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_2243776
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         'C19 H23 Br N2 O5 S'
_chemical_formula_sum            'C19 H23 Br N2 O5 S'
_chemical_formula_weight         471.36
_chemical_name_common
;
6-(4-bromo-1-tosylpyrrol-2-yl)-4,4-dimethyl-5-nitrohexan-2-one
;
_chemical_name_systematic
;
6-(4-bromo-1-tosylpyrrol-2-yl)-4,4-dimethyl-5-nitrohexan-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.0550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7375(2)
_cell_length_b                   15.9728(3)
_cell_length_c                   16.7621(3)
_cell_measurement_reflns_used    9692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      46.08
_cell_measurement_theta_min      2.75
_cell_volume                     2068.68(8)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            226885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         46.515
_diffrn_reflns_theta_min         1.762
_exptl_absorpt_coefficient_mu    2.120
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.614
_exptl_crystal_size_mid          0.558
_exptl_crystal_size_min          0.546
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.719
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         18433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0366P)²+0.3750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                15578
_reflns_number_total             18433
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2036sup1.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243776
_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   0.356
_shelx_estimated_absorpt_t_max   0.391
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.22008(2) 0.57357(2) 0.01021(2) 0.01695(2) Uani d 1 . .
N N1 0.17070(6) 0.42535(3) 0.20251(3) 0.01145(6) Uani d 1 . .
C C3 0.37857(7) 0.44721(3) 0.11798(3) 0.01261(7) Uani d 1 . .
H H3 0.483498 0.444262 0.091152 0.015 Uiso calc 1 . .
N N8 0.44371(8) 0.23904(3) 0.11422(3) 0.01693(8) Uani d 1 . .
C C2 0.33880(7) 0.40180(3) 0.18381(3) 0.01093(6) Uani d 1 . .
C C4 0.23457(7) 0.49959(3) 0.09697(3) 0.01208(7) Uani d 1 . .
O O9 0.57359(9) 0.27017(4) 0.08769(4) 0.02494(10) Uani d 1 . .
C C5 0.10853(7) 0.48676(3) 0.14928(3) 0.01247(7) Uani d 1 . .
H H5 -0.000347 0.514227 0.149476 0.015 Uiso calc 1 . .
C C6 0.45096(7) 0.33876(3) 0.22754(3) 0.01219(7) Uani d 1 . .
H H6A 0.434437 0.344148 0.285479 0.015 Uiso calc 1 . .
H H6B 0.573549 0.351849 0.218744 0.015 Uiso calc 1 . .
C C7 0.41499(7) 0.24784(3) 0.20244(3) 0.01148(7) Uani d 1 . .
H H7 0.290618 0.235381 0.210853 0.014 Uiso calc 1 . .
O O10 0.33578(10) 0.19916(4) 0.07358(3) 0.02730(12) Uani d 1 . .
C C11 0.52787(7) 0.18170(3) 0.24936(3) 0.01285(7) Uani d 1 . .
C C12 0.51170(9) 0.09560(4) 0.20840(4) 0.01678(9) Uani d 1 . .
H H12A 0.566845 0.052934 0.243202 0.025 Uiso calc 1 . .
H H12B 0.568869 0.097269 0.157640 0.025 Uiso calc 1 . .
H H12C 0.389085 0.081793 0.198271 0.025 Uiso calc 1 . .
C C13 0.71998(8) 0.20658(4) 0.25676(5) 0.01915(10) Uani d 1 . .
H H13A 0.786783 0.161943 0.284110 0.029 Uiso calc 1 . .
H H13B 0.732997 0.258568 0.287538 0.029 Uiso calc 1 . .
H H13C 0.762620 0.215080 0.203347 0.029 Uiso calc 1 . .
C C14 0.46432(8) 0.17737(4) 0.33473(3) 0.01491(8) Uani d 1 . .
H H14A 0.542953 0.139094 0.365724 0.018 Uiso calc 1 . .
H H14B 0.479873 0.233710 0.358656 0.018 Uiso calc 1 . .
C C15 0.28132(9) 0.14997(4) 0.34817(4) 0.01594(8) Uani d 1 . .
O O16 0.18406(7) 0.12067(4) 0.29612(3) 0.02047(8) Uani d 1 . .
C C17 0.22683(13) 0.16059(6) 0.43234(5) 0.02768(15) Uani d 1 . .
H H17A 0.322919 0.145112 0.469905 0.042 Uiso calc 1 . .
H H17B 0.127148 0.124460 0.440913 0.042 Uiso calc 1 . .
H H17C 0.194909 0.219124 0.441078 0.042 Uiso calc 1 . .
S S18 0.05660(2) 0.39646(2) 0.28052(2) 0.01139(2) Uani d 1 . .
O O19 -0.11952(6) 0.41232(3) 0.25512(3) 0.01581(7) Uani d 1 . .
O O20 0.11448(7) 0.31396(3) 0.30178(3) 0.01737(7) Uani d 1 . .
C C21 0.11675(7) 0.46504(3) 0.35854(3) 0.01230(7) Uani d 1 . .
C C22 0.04515(8) 0.54520(4) 0.35859(4) 0.01510(8) Uani d 1 . .
H H22 -0.032923 0.562991 0.316297 0.018 Uiso calc 1 . .
C C23 0.09053(9) 0.59848(4) 0.42186(4) 0.01861(9) Uani d 1 . .
H H23 0.043057 0.653310 0.422446 0.022 Uiso calc 1 . .
C C24 0.20469(9) 0.57294(4) 0.48466(4) 0.01888(10) Uani d 1 . .
C C25 0.27117(9) 0.49166(5) 0.48363(4) 0.01981(10) Uani d 1 . .
H H25 0.346580 0.473194 0.526648 0.024 Uiso calc 1 . .
C C26 0.22901(8) 0.43731(4) 0.42083(4) 0.01686(9) Uani d 1 . .
H H26 0.275760 0.382327 0.420358 0.020 Uiso calc 1 . .
C C27 0.25660(13) 0.63236(6) 0.55124(5) 0.02910(16) Uani d 1 . .
H H27A 0.286189 0.600523 0.600043 0.044 Uiso calc 1 . .
H H27B 0.160185 0.670287 0.560580 0.044 Uiso calc 1 . .
H H27C 0.357263 0.665022 0.536490 0.044 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 0.0033 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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C2 . . 109.72(4) ?
C5 N1 S18 . . 120.89(4) ?
C2 N1 S18 . . 129.11(4) ?
C2 C3 C4 . . 107.72(5) ?
C2 C3 H3 . . 126.1 ?
C4 C3 H3 . . 126.1 ?
O9 N8 O10 . . 123.76(6) ?
O9 N8 C7 . . 118.87(6) ?
O10 N8 C7 . . 117.35(6) ?
C3 C2 N1 . . 106.76(4) ?
C3 C2 C6 . . 127.03(5) ?
N1 C2 C6 . . 126.21(5) ?
C5 C4 C3 . . 109.30(5) ?
C5 C4 Br1 . . 125.45(4) ?
C3 C4 Br1 . . 125.24(4) ?
C4 C5 N1 . . 106.47(5) ?
C4 C5 H5 . . 126.8 ?
N1 C5 H5 . . 126.8 ?
C2 C6 C7 . . 114.27(4) ?
C2 C6 H6A . . 108.7 ?
C7 C6 H6A . . 108.7 ?
C2 C6 H6B . . 108.7 ?
C7 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
N8 C7 C6 . . 108.79(4) ?
N8 C7 C11 . . 108.84(4) ?
C6 C7 C11 . . 114.54(4) ?
N8 C7 H7 . . 108.2 ?
C6 C7 H7 . . 108.2 ?
C11 C7 H7 . . 108.2 ?
C13 C11 C12 . . 108.80(5) ?
C13 C11 C14 . . 106.98(5) ?
C12 C11 C14 . . 110.62(5) ?
C13 C11 C7 . . 112.29(5) ?
C12 C11 C7 . . 110.53(4) ?
C14 C11 C7 . . 107.56(4) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C15 C14 C11 . . 120.01(5) ?
C15 C14 H14A . . 107.3 ?
C11 C14 H14A . . 107.3 ?
C15 C14 H14B . . 107.3 ?
C11 C14 H14B . . 107.3 ?
H14A C14 H14B . . 106.9 ?
O16 C15 C17 . . 121.55(6) ?
O16 C15 C14 . . 123.66(6) ?
C17 C15 C14 . . 114.78(6) ?
C15 C17 H17A . . 109.5 ?
C15 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C15 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O19 S18 O20 . . 121.24(3) ?
O19 S18 N1 . . 104.58(3) ?
O20 S18 N1 . . 106.03(3) ?
O19 S18 C21 . . 108.85(3) ?
O20 S18 C21 . . 108.86(3) ?
N1 S18 C21 . . 106.24(2) ?
C26 C21 C22 . . 121.51(5) ?
C26 C21 S18 . . 119.41(5) ?
C22 C21 S18 . . 119.02(4) ?
C23 C22 C21 . . 118.56(6) ?
C23 C22 H22 . . 120.7 ?
C21 C22 H22 . . 120.7 ?
C22 C23 C24 . . 121.30(6) ?
C22 C23 H23 . . 119.4 ?
C24 C23 H23 . . 119.4 ?
C25 C24 C23 . . 118.69(6) ?
C25 C24 C27 . . 120.79(7) ?
C23 C24 C27 . . 120.51(7) ?
C26 C25 C24 . . 121.21(6) ?
C26 C25 H25 . . 119.4 ?
C24 C25 H25 . . 119.4 ?
C25 C26 C21 . . 118.72(6) ?
C25 C26 H26 . . 120.6 ?
C21 C26 H26 . . 120.6 ?
C24 C27 H27A . . 109.5 ?
C24 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C24 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 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 . 1.8727(5) ?
N1 C5 . 1.3942(7) ?
N1 C2 . 1.4054(7) ?
N1 S18 . 1.6808(5) ?
C3 C2 . 1.3692(7) ?
C3 C4 . 1.4226(8) ?
C3 H3 . 0.9500 ?
N8 O9 . 1.2258(9) ?
N8 O10 . 1.2275(8) ?
N8 C7 . 1.5135(7) ?
C2 C6 . 1.4954(7) ?
C4 C5 . 1.3613(8) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.5333(7) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C11 . 1.5571(7) ?
C7 H7 . 1.0000 ?
C11 C13 . 1.5372(8) ?
C11 C12 . 1.5392(8) ?
C11 C14 . 1.5392(8) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 C15 . 1.5103(9) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 O16 . 1.2150(8) ?
C15 C17 . 1.5036(10) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
S18 O19 . 1.4285(5) ?
S18 O20 . 1.4307(5) ?
S18 C21 . 1.7499(6) ?
C21 C26 . 1.3944(8) ?
C21 C22 . 1.3951(8) ?
C22 C23 . 1.3902(9) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.3984(10) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.3970(11) ?
C24 C27 . 1.5033(10) ?
C25 C26 . 1.3898(10) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 C3 C2 N1 . . . . 0.72(6) ?
C4 C3 C2 C6 . . . . -179.65(5) ?
C5 N1 C2 C3 . . . . -1.40(6) ?
S18 N1 C2 C3 . . . . -175.24(4) ?
C5 N1 C2 C6 . . . . 178.97(5) ?
S18 N1 C2 C6 . . . . 5.13(8) ?
C2 C3 C4 C5 . . . . 0.21(7) ?
C2 C3 C4 Br1 . . . . -179.12(4) ?
C3 C4 C5 N1 . . . . -1.05(6) ?
Br1 C4 C5 N1 . . . . 178.27(4) ?
C2 N1 C5 C4 . . . . 1.52(6) ?
S18 N1 C5 C4 . . . . 175.95(4) ?
C3 C2 C6 C7 . . . . -96.18(6) ?
N1 C2 C6 C7 . . . . 83.39(7) ?
O9 N8 C7 C6 . . . . 45.57(7) ?
O10 N8 C7 C6 . . . . -135.92(6) ?
O9 N8 C7 C11 . . . . -79.85(6) ?
O10 N8 C7 C11 . . . . 98.66(6) ?
C2 C6 C7 N8 . . . . 59.57(6) ?
C2 C6 C7 C11 . . . . -178.41(5) ?
N8 C7 C11 C13 . . . . 76.03(6) ?
C6 C7 C11 C13 . . . . -45.96(7) ?
N8 C7 C11 C12 . . . . -45.66(6) ?
C6 C7 C11 C12 . . . . -167.66(5) ?
N8 C7 C11 C14 . . . . -166.52(4) ?
C6 C7 C11 C14 . . . . 71.48(6) ?
C13 C11 C14 C15 . . . . -176.89(5) ?
C12 C11 C14 C15 . . . . -58.53(7) ?
C7 C11 C14 C15 . . . . 62.27(6) ?
C11 C14 C15 O16 . . . . 9.44(9) ?
C11 C14 C15 C17 . . . . -171.28(6) ?
C5 N1 S18 O19 . . . . 27.62(5) ?
C2 N1 S18 O19 . . . . -159.14(5) ?
C5 N1 S18 O20 . . . . 156.84(5) ?
C2 N1 S18 O20 . . . . -29.92(6) ?
C5 N1 S18 C21 . . . . -87.44(5) ?
C2 N1 S18 C21 . . . . 85.80(5) ?
O19 S18 C21 C26 . . . . 144.02(5) ?
O20 S18 C21 C26 . . . . 9.94(6) ?
N1 S18 C21 C26 . . . . -103.86(5) ?
O19 S18 C21 C22 . . . . -33.26(5) ?
O20 S18 C21 C22 . . . . -167.34(5) ?
N1 S18 C21 C22 . . . . 78.86(5) ?
C26 C21 C22 C23 . . . . 1.22(9) ?
S18 C21 C22 C23 . . . . 178.44(5) ?
C21 C22 C23 C24 . . . . -0.29(10) ?
C22 C23 C24 C25 . . . . -1.06(10) ?
C22 C23 C24 C27 . . . . 178.05(6) ?
C23 C24 C25 C26 . . . . 1.54(10) ?
C27 C24 C25 C26 . . . . -177.57(7) ?
C24 C25 C26 C21 . . . . -0.65(10) ?
C22 C21 C26 C25 . . . . -0.76(9) ?
S18 C21 C26 C25 . . . . -177.96(5) ?

_cod_database_fobs_code 2243776
