#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:06:57 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268520 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/84/7128474.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_7128474
loop_
_publ_author_name
'Kodama, Yuki'
'Imai, Saki'
'Fujimoto, Junko'
'Sato, Kohei'
'Mase, Nobuyuki'
'Narumi, Tetsuo'
_publ_section_title
;
 Stereoselective synthesis of highly functionalized
 (Z)-chloroalkene dipeptide isosteres containing an
 α,α-disubstituted amino acid.
;
_journal_issue                   56
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6915
_journal_page_last               6918
_journal_paper_doi               10.1039/d1cc02952e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C14 H17 Br Cl N O4 S'
_chemical_formula_sum            'C14 H17 Br Cl N O4 S'
_chemical_formula_weight         410.71
_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     dual
_audit_creation_date             2019-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.055(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5794(9)
_cell_length_b                   8.0509(19)
_cell_length_c                   33.122(6)
_cell_measurement_reflns_used    2068
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.6530
_cell_measurement_theta_min      3.0690
_cell_volume                     1754.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Rigaku Mercury area detector'
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 120.00   1.00    8.00    --   30.00  54.00   0.00  180
  2  ω    -60.00 114.00   1.00    8.00    --   30.00  54.00 120.00  174
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1055717000
_diffrn_orient_matrix_UB_12      -0.0175931000
_diffrn_orient_matrix_UB_13      0.0010955000
_diffrn_orient_matrix_UB_21      0.0078460000
_diffrn_orient_matrix_UB_22      -0.0087131000
_diffrn_orient_matrix_UB_23      0.0211500000
_diffrn_orient_matrix_UB_31      -0.0207576000
_diffrn_orient_matrix_UB_32      0.0861680000
_diffrn_orient_matrix_UB_33      0.0023866000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            9634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.604
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0857
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0884P)²+6.4801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2556
_reflns_number_total             3193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02952e2.cif
_cod_data_source_block           sim_up
_cod_depositor_comments
'Adding full bibliography for 7128471--7128475.cif.'
_cod_database_code               7128474
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H18 Br Cl2 N O4 S'
_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   0.353
_shelx_estimated_absorpt_t_min   0.228
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.802(3)
 0.198(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C6(H6)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.646
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_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
Br1 Br 0.9827(2) 0.83040(18) 0.57486(3) 0.0895(5) Uani 1 1 d . . . . .
S1 S 0.7258(3) 0.8285(3) 0.32926(6) 0.0411(5) Uani 1 1 d . . . . .
Cl1 Cl 0.5348(4) 0.4420(3) 0.40513(7) 0.0610(6) Uani 1 1 d . . . . .
O4 O 0.9776(9) 0.4254(9) 0.33355(18) 0.0534(15) Uani 1 1 d . . . . .
O2 O 0.7962(8) 0.7268(8) 0.29640(18) 0.0483(15) Uani 1 1 d . . . . .
O1 O 0.8483(9) 0.9676(9) 0.3409(2) 0.0595(18) Uani 1 1 d . . . . .
O3 O 0.6502(10) 0.3666(10) 0.3185(2) 0.0624(18) Uani 1 1 d . . . . .
N1 N 0.6976(9) 0.7178(9) 0.37222(19) 0.0384(15) Uani 1 1 d . . . . .
C1 C 0.8949(12) 0.6944(11) 0.4388(2) 0.0433(19) Uani 1 1 d . . . . .
C11 C 0.4651(11) 0.8910(10) 0.3197(2) 0.0371(16) Uani 1 1 d . . . . .
C8 C 0.7239(11) 0.5383(11) 0.3759(2) 0.0422(19) Uani 1 1 d . . . . .
C7 C 0.8766(12) 0.6529(11) 0.3948(3) 0.044(2) Uani 1 1 d . . . . .
H7 H 1.004887 0.660628 0.379877 0.053 Uiso 1 1 calc R . . . .
C9 C 0.7750(13) 0.4372(11) 0.3388(3) 0.0458(19) Uani 1 1 d . . . . .
C5 C 1.1084(15) 0.7108(13) 0.4978(3) 0.056(2) Uani 1 1 d . . . . .
H5 H 1.235047 0.696924 0.509883 0.067 Uiso 1 1 calc R . . . .
C12 C 0.3393(12) 0.7306(12) 0.3143(3) 0.055(2) Uani 1 1 d . . . . .
H12A H 0.406298 0.658620 0.295448 0.083 Uiso 1 1 calc GR . . . .
H12B H 0.206554 0.758225 0.304338 0.083 Uiso 1 1 calc GR . . . .
H12C H 0.326938 0.675242 0.339877 0.083 Uiso 1 1 calc GR . . . .
C4 C 0.9460(16) 0.7720(13) 0.5199(3) 0.057(2) Uani 1 1 d . . . . .
C10 C 1.0414(17) 0.3391(14) 0.2969(3) 0.070(3) Uani 1 1 d . . . . .
H10A H 1.000668 0.402426 0.273666 0.105 Uiso 1 1 calc GR . . . .
H10B H 0.978853 0.231473 0.295904 0.105 Uiso 1 1 calc GR . . . .
H10C H 1.186512 0.326865 0.296940 0.105 Uiso 1 1 calc GR . . . .
C2 C 0.7351(14) 0.7599(14) 0.4605(3) 0.057(2) Uani 1 1 d . . . . .
H2 H 0.609233 0.774938 0.448251 0.069 Uiso 1 1 calc R . . . .
C3 C 0.7625(18) 0.8041(16) 0.5016(3) 0.068(3) Uani 1 1 d . . . . .
H3 H 0.657701 0.854182 0.515922 0.082 Uiso 1 1 calc R . . . .
C13 C 0.4720(15) 0.9910(13) 0.2805(3) 0.058(2) Uani 1 1 d . . . . .
H13A H 0.567718 1.080287 0.283249 0.087 Uiso 1 1 calc GR . . . .
H13B H 0.339577 1.035666 0.274913 0.087 Uiso 1 1 calc GR . . . .
H13C H 0.512862 0.919957 0.258689 0.087 Uiso 1 1 calc GR . . . .
C14 C 0.3886(15) 0.9946(14) 0.3550(3) 0.062(3) Uani 1 1 d . . . . .
H14A H 0.409449 0.934689 0.379731 0.093 Uiso 1 1 calc GR . . . .
H14B H 0.246295 1.016764 0.351561 0.093 Uiso 1 1 calc GR . . . .
H14C H 0.461899 1.097639 0.356018 0.093 Uiso 1 1 calc GR . . . .
C6 C 1.0792(14) 0.6703(13) 0.4574(3) 0.054(2) Uani 1 1 d . . . . .
H6 H 1.186587 0.626003 0.442683 0.065 Uiso 1 1 calc R . . . .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O2 S1 N1 111.9(4) . . ?
O2 S1 C11 109.3(4) . . ?
O1 S1 O2 117.9(4) . . ?
O1 S1 N1 104.3(4) . . ?
O1 S1 C11 111.2(4) . . ?
N1 S1 C11 100.9(3) . . ?
C9 O4 C10 115.1(8) . . ?
C8 N1 S1 125.4(5) . . ?
C8 N1 C7 61.1(5) . . ?
C7 N1 S1 121.4(5) . . ?
C2 C1 C7 122.2(8) . . ?
C6 C1 C7 118.4(7) . . ?
C6 C1 C2 119.5(8) . . ?
C12 C11 S1 107.1(6) . . ?
C13 C11 S1 105.4(6) . . ?
C13 C11 C12 111.1(8) . . ?
C14 C11 S1 109.3(6) . . ?
C14 C11 C12 111.6(7) . . ?
C14 C11 C13 112.0(8) . . ?
N1 C8 Cl1 113.5(5) . . ?
N1 C8 C7 60.3(5) . . ?
N1 C8 C9 119.4(7) . . ?
C7 C8 Cl1 121.0(6) . . ?
C7 C8 C9 121.4(7) . . ?
C9 C8 Cl1 111.6(6) . . ?
N1 C7 C1 118.1(7) . . ?
N1 C7 C8 58.5(5) . . ?
C1 C7 C8 126.6(7) . . ?
O4 C9 C8 111.2(8) . . ?
O3 C9 O4 124.8(8) . . ?
O3 C9 C8 123.7(8) . . ?
C4 C5 C6 119.0(9) . . ?
C5 C4 Br1 119.8(8) . . ?
C3 C4 Br1 119.2(7) . . ?
C3 C4 C5 120.8(9) . . ?
C1 C2 C3 120.1(9) . . ?
C4 C3 C2 119.2(9) . . ?
C1 C6 C5 121.4(8) . . ?
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
Br1 C4 1.896(9) . ?
S1 O2 1.439(6) . ?
S1 O1 1.433(7) . ?
S1 N1 1.689(7) . ?
S1 C11 1.815(8) . ?
Cl1 C8 1.758(8) . ?
O4 C9 1.348(10) . ?
O4 C10 1.461(11) . ?
O3 C9 1.203(11) . ?
N1 C8 1.461(11) . ?
N1 C7 1.489(10) . ?
C1 C7 1.500(12) . ?
C1 C2 1.380(12) . ?
C1 C6 1.374(12) . ?
C11 C12 1.544(11) . ?
C11 C13 1.528(11) . ?
C11 C14 1.523(12) . ?
C8 C7 1.500(13) . ?
C8 C9 1.513(12) . ?
C5 C4 1.385(13) . ?
C5 C6 1.392(13) . ?
C4 C3 1.376(15) . ?
C2 C3 1.416(14) . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.802(3)
2 0.198(3)
