#------------------------------------------------------------------------------
#$Date: 2021-10-05 13:01:06 +0300 (Tue, 05 Oct 2021) $
#$Revision: 269566 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038954.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_4038954
loop_
_publ_author_name
'Vasin, V.A.'
'Bolusheva, I.Yu.'
'Razin, V.V.'
'Kapkaeva, S.R.'
'Petrov, P.S.'
'Somov, N.V.'
_publ_section_title
;
 Methyl (Z)-3-Bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate: Synthesis
 and Reactions with Dimethyl Malonate and Methyl Acetoacetate
;
_journal_issue                   3
_journal_name_full
;
 Russian Journal of Organic Chemistry
;
_journal_page_first              299
_journal_page_last               306
_journal_paper_doi               10.1134/S1070428016030015
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C16 H18 O8 S'
_chemical_formula_weight         370.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2015-06-24T13:24:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                103.273(4)
_cell_angle_beta                 98.200(4)
_cell_angle_gamma                114.451(5)
_cell_formula_units_Z            2
_cell_length_a                   8.5960(4)
_cell_length_b                   8.8154(4)
_cell_length_c                   13.5747(6)
_cell_measurement_reflns_used    6405
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.692
_cell_measurement_theta_min      4.282
_cell_volume                     877.98(8)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0302
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0257625
_diffrn_orient_matrix_UB_12      0.0703347
_diffrn_orient_matrix_UB_13      0.0468555
_diffrn_orient_matrix_UB_21      -0.0713079
_diffrn_orient_matrix_UB_22      0.0148152
_diffrn_orient_matrix_UB_23      -0.0202629
_diffrn_orient_matrix_UB_31      -0.0557222
_diffrn_orient_matrix_UB_32      -0.0594923
_diffrn_orient_matrix_UB_33      0.0223514
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17516
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         3.455
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.2304
_exptl_crystal_size_mid          0.1349
_exptl_crystal_size_min          0.0942
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0582P)²+0.1932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0
_reflns_number_gt                4197
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tmpc1szkg3b
_cod_data_source_block           499pr40
_cod_database_code               4038954
loop_
_symmetry_equiv_pos_as_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
C1 C 0.89674(19) 0.14117(18) 0.07470(12) 0.0351(3) Uani 1 1 d . . . . .
C2 C 1.0777(2) 0.2074(2) 0.11501(13) 0.0433(3) Uani 1 1 d . . . . .
C3 C 1.1928(2) 0.3065(2) 0.06617(14) 0.0458(4) Uani 1 1 d . . . . .
C4 C 1.1308(2) 0.3421(2) -0.02101(13) 0.0410(3) Uani 1 1 d . . . . .
C5 C 0.9484(2) 0.2722(2) -0.06044(15) 0.0485(4) Uani 1 1 d . . . . .
C6 C 0.8306(2) 0.1714(2) -0.01372(14) 0.0450(4) Uani 1 1 d . . . . .
C7 C 1.2583(3) 0.4524(3) -0.07186(19) 0.0577(5) Uani 1 1 d . . . . .
C8 C 0.69986(19) 0.17696(18) 0.21405(12) 0.0346(3) Uani 1 1 d . . . . .
C9 C 0.80958(19) 0.28198(19) 0.32481(12) 0.0366(3) Uani 1 1 d . . . . .
C10 C 0.62129(18) 0.14334(18) 0.30526(11) 0.0335(3) Uani 1 1 d . . . . .
C11 C 0.5948(2) -0.0160(2) 0.33870(12) 0.0390(3) Uani 1 1 d . . . . .
C12 C 0.4013(5) -0.3131(3) 0.3091(3) 0.0829(8) Uani 1 1 d . . . . .
C13 C 0.48822(19) 0.2109(2) 0.31937(12) 0.0369(3) Uani 1 1 d . . . . .
C14 C 0.2839(3) 0.2228(4) 0.4157(2) 0.0601(5) Uani 1 1 d . . . . .
C15 C 0.8612(2) 0.4730(2) 0.37273(13) 0.0418(3) Uani 1 1 d . . . . .
C16 C 1.0019(4) 0.7567(3) 0.3580(2) 0.0795(8) Uani 1 1 d D . . . .
O1 O 0.58792(15) -0.11117(15) 0.06027(10) 0.0532(3) Uani 1 1 d . . . . .
O2 O 0.84097(17) -0.03263(16) 0.20899(10) 0.0500(3) Uani 1 1 d . . . . .
O3 O 0.44336(17) -0.15440(15) 0.28010(10) 0.0523(3) Uani 1 1 d . . . . .
O4 O 0.69564(19) -0.01537(18) 0.40893(11) 0.0621(4) Uani 1 1 d . . . . .
O5 O 0.40577(17) 0.15604(16) 0.38869(10) 0.0494(3) Uani 1 1 d . . . . .
O6 O 0.46768(19) 0.3080(2) 0.27644(12) 0.0618(4) Uani 1 1 d . . . . .
O7 O 0.8357(2) 0.53041(18) 0.45461(13) 0.0724(4) Uani 1 1 d . . . . .
O8 O 0.9446(2) 0.56810(15) 0.31763(10) 0.0591(4) Uani 1 1 d . . . . .
S1 S 0.74945(5) 0.01948(5) 0.13748(3) 0.03794(11) Uani 1 1 d . . . . .
H1 H 1.122(3) 0.183(3) 0.1762(16) 0.056(5) Uiso 1 1 d . . . . .
H2 H 1.314(3) 0.353(3) 0.0955(15) 0.053(5) Uiso 1 1 d . . . . .
H3 H 0.900(3) 0.294(3) -0.1216(18) 0.067(6) Uiso 1 1 d . . . . .
H4 H 0.705(3) 0.129(3) -0.0446(16) 0.058(6) Uiso 1 1 d . . . . .
H5 H 1.352(4) 0.559(4) -0.019(2) 0.101(9) Uiso 1 1 d . . . . .
H6 H 1.197(4) 0.494(4) -0.118(2) 0.091(8) Uiso 1 1 d . . . . .
H7 H 1.316(4) 0.395(4) -0.104(2) 0.104(10) Uiso 1 1 d . . . . .
H8 H 0.652(2) 0.230(2) 0.1724(14) 0.039(4) Uiso 1 1 d . . . . .
H9 H 0.895(2) 0.251(2) 0.3516(14) 0.043(5) Uiso 1 1 d . . . . .
H10 H 0.494(4) -0.345(4) 0.294(2) 0.099(10) Uiso 1 1 d . . . . .
H11 H 0.288(4) -0.396(4) 0.264(2) 0.099(9) Uiso 1 1 d . . . . .
H12 H 0.394(5) -0.287(5) 0.380(3) 0.135(14) Uiso 1 1 d . . . . .
H13 H 0.248(4) 0.187(4) 0.472(2) 0.100(9) Uiso 1 1 d . . . . .
H14 H 0.335(4) 0.337(4) 0.428(2) 0.095(9) Uiso 1 1 d . . . . .
H15 H 0.183(4) 0.181(4) 0.355(3) 0.108(10) Uiso 1 1 d . . . . .
H16 H 1.075(3) 0.789(4) 0.4251(15) 0.128(7) Uiso 1 1 d D . . . .
H17 H 0.903(3) 0.777(5) 0.360(2) 0.128(7) Uiso 1 1 d D . . . .
H18 H 1.064(3) 0.802(4) 0.312(2) 0.128(7) Uiso 1 1 d 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 -10 1 0.053
8 -7 12 0.0643
11 1 -2 0.1059
0 -1 18 0.0561
6 7 -9 0.1086
-3 -9 -1 0.0852
-10 4 12 0.0791
-8 11 2 0.0943
-10 10 -2 0.0787
-9 3 -9 0.0257
0 0 -18 0.031
0 11 -1 0.1025
-1 11 -11 0.0792
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
C6 C1 C2 120.83(14) . . ?
C6 C1 S1 119.53(11) . . ?
C2 C1 S1 119.63(12) . . ?
C1 C2 C3 119.13(15) . . ?
C1 C2 H1 120.1(12) . . ?
C3 C2 H1 120.8(12) . . ?
C4 C3 C2 121.36(15) . . ?
C4 C3 H2 120.7(12) . . ?
C2 C3 H2 117.9(12) . . ?
C3 C4 C5 118.20(15) . . ?
C3 C4 C7 120.51(16) . . ?
C5 C4 C7 121.29(17) . . ?
C6 C5 C4 121.55(16) . . ?
C6 C5 H3 118.0(13) . . ?
C4 C5 H3 120.5(13) . . ?
C1 C6 C5 118.90(15) . . ?
C1 C6 H4 124.0(12) . . ?
C5 C6 H4 117.1(12) . . ?
C4 C7 H5 109.8(17) . . ?
C4 C7 H6 109.7(16) . . ?
H5 C7 H6 105(2) . . ?
C4 C7 H7 111.6(18) . . ?
H5 C7 H7 105(2) . . ?
H6 C7 H7 115(2) . . ?
C9 C8 C10 59.93(10) . . ?
C9 C8 S1 119.79(11) . . ?
C10 C8 S1 120.02(10) . . ?
C9 C8 H8 119.5(10) . . ?
C10 C8 H8 115.8(10) . . ?
S1 C8 H8 112.4(10) . . ?
C8 C9 C15 123.08(14) . . ?
C8 C9 C10 60.88(9) . . ?
C15 C9 C10 120.38(12) . . ?
C8 C9 H9 116.4(11) . . ?
C15 C9 H9 112.8(11) . . ?
C10 C9 H9 113.7(11) . . ?
C13 C10 C9 115.63(12) . . ?
C13 C10 C11 116.53(12) . . ?
C9 C10 C11 117.29(12) . . ?
C13 C10 C8 113.71(12) . . ?
C9 C10 C8 59.19(10) . . ?
C11 C10 C8 122.14(12) . . ?
O4 C11 O3 125.14(14) . . ?
O4 C11 C10 124.26(15) . . ?
O3 C11 C10 110.59(13) . . ?
O3 C12 H10 104.1(18) . . ?
O3 C12 H11 105.2(18) . . ?
H10 C12 H11 112(3) . . ?
O3 C12 H12 108(2) . . ?
H10 C12 H12 117(3) . . ?
H11 C12 H12 109(3) . . ?
O6 C13 O5 125.14(14) . . ?
O6 C13 C10 123.73(13) . . ?
O5 C13 C10 111.04(12) . . ?
O5 C14 H13 107.3(18) . . ?
O5 C14 H14 109.2(19) . . ?
H13 C14 H14 115(3) . . ?
O5 C14 H15 111.2(18) . . ?
H13 C14 H15 112(2) . . ?
H14 C14 H15 102(2) . . ?
O7 C15 O8 124.91(15) . . ?
O7 C15 C9 123.05(16) . . ?
O8 C15 C9 111.95(13) . . ?
O8 C16 H16 103(2) . . ?
O8 C16 H17 110(2) . . ?
H16 C16 H17 112.8(13) . . ?
O8 C16 H18 104(2) . . ?
H16 C16 H18 113.2(13) . . ?
H17 C16 H18 113.4(13) . . ?
C11 O3 C12 114.95(17) . . ?
C13 O5 C14 116.67(14) . . ?
C15 O8 C16 116.33(15) . . ?
O2 S1 O1 119.49(8) . . ?
O2 S1 C1 109.51(7) . . ?
O1 S1 C1 109.15(7) . . ?
O2 S1 C8 107.26(7) . . ?
O1 S1 C8 107.16(7) . . ?
C1 S1 C8 102.96(7) . . ?
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
C1 C6 1.383(2) . ?
C1 C2 1.385(2) . ?
C1 S1 1.7560(15) . ?
C2 C3 1.385(2) . ?
C2 H1 0.97(2) . ?
C3 C4 1.383(2) . ?
C3 H2 0.93(2) . ?
C4 C5 1.390(2) . ?
C4 C7 1.505(2) . ?
C5 C6 1.384(2) . ?
C5 H3 0.97(2) . ?
C6 H4 0.98(2) . ?
C7 H5 0.97(3) . ?
C7 H6 0.99(3) . ?
C7 H7 0.93(3) . ?
C8 C9 1.497(2) . ?
C8 C10 1.5226(19) . ?
C8 S1 1.7729(14) . ?
C8 H8 0.957(18) . ?
C9 C15 1.500(2) . ?
C9 C10 1.508(2) . ?
C9 H9 0.935(19) . ?
C10 C13 1.5081(19) . ?
C10 C11 1.5127(19) . ?
C11 O4 1.1907(19) . ?
C11 O3 1.3269(19) . ?
C12 O3 1.455(2) . ?
C12 H10 0.98(3) . ?
C12 H11 0.95(3) . ?
C12 H12 0.96(4) . ?
C13 O6 1.1948(19) . ?
C13 O5 1.3181(18) . ?
C14 O5 1.449(2) . ?
C14 H13 0.93(3) . ?
C14 H14 0.88(3) . ?
C14 H15 0.98(3) . ?
C15 O7 1.201(2) . ?
C15 O8 1.311(2) . ?
C16 O8 1.460(2) . ?
C16 H16 0.935(17) . ?
C16 H17 0.936(17) . ?
C16 H18 0.932(17) . ?
O1 S1 1.4352(12) . ?
O2 S1 1.4347(13) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H4 O1 0.98(2) 2.43(2) 3.353(2) 157.9(17) 2_655
C14 H13 O4 0.93(3) 2.58(3) 3.344(3) 140(2) 2_656
C16 H16 O4 0.935(17) 2.52(2) 3.376(3) 152(3) 2_766
