#------------------------------------------------------------------------------
#$Date: 2024-07-05 19:55:35 +0200 (Fri 05 de Jul de 2024) $
#$Revision: 293246 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/99/7159903.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_7159903
loop_
_publ_author_name
'Bora, Surjya Kumar'
'Biswas, Subhamoy'
'Behera, Bipin Kumar'
'Saikia, Anil K.'
_publ_section_title
;
 Stereoselective synthesis of gem-dihalopiperidines via the
 halo-aza-Prins cyclization reaction: access to piperidin-4-ones and
 pyridines.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3893
_journal_page_last               3903
_journal_paper_doi               10.1039/d4ob00338a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C18 H18 Br Cl2 N O2 S'
_chemical_formula_weight         463.20
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2hp74l
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-12-14 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.195(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.812(2)
_cell_length_b                   15.310(3)
_cell_length_c                   11.343(2)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.29
_cell_volume                     1899.3(6)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            62323
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.244
_diffrn_reflns_theta_min         2.289
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       Block
_exptl_crystal_F_000             936
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.4346
_refine_diff_density_max         1.287
_refine_diff_density_min         -1.557
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0596
_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)+(0.1146P)²+4.8817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3813
_reflns_number_total             4681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00338a3.cif
_cod_data_source_block           surjya_NTs_0ma_a
_cod_depositor_comments          'Adding full bibliography for 7159903.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159903
_shelx_shelxl_version_number     2019/1
_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.
;
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 -0.10224(5) 0.80364(4) 0.17899(5) 0.0565(2) Uani 1 1 d . . . . .
Cl1 Cl 0.13476(11) 0.82213(7) 0.40426(12) 0.0437(3) Uani 1 1 d . . . . .
Cl2 Cl 0.30805(18) 0.42564(11) -0.07157(14) 0.0706(5) Uani 1 1 d . . . . .
S1 S 0.25048(8) 0.51181(6) 0.52229(9) 0.0290(2) Uani 1 1 d . . . . .
O1 O 0.1877(3) 0.4718(2) 0.5942(3) 0.0416(7) Uani 1 1 d . . . . .
O2 O 0.3056(3) 0.45782(19) 0.4560(3) 0.0385(7) Uani 1 1 d . . . . .
N1 N 0.1483(3) 0.5757(2) 0.4150(3) 0.0261(6) Uani 1 1 d . . . . .
C1 C 0.3635(3) 0.5829(3) 0.6234(4) 0.0298(7) Uani 1 1 d . . . . .
C2 C 0.3525(4) 0.6165(3) 0.7321(4) 0.0353(8) Uani 1 1 d . . . . .
H2 H 0.288337 0.599120 0.755325 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4381(4) 0.6761(3) 0.8057(4) 0.0415(10) Uani 1 1 d . . . . .
H3 H 0.430298 0.699392 0.877950 0.050 Uiso 1 1 calc R U . . .
C4 C 0.5360(4) 0.7020(3) 0.7732(5) 0.0404(10) Uani 1 1 d . . . . .
C5 C 0.5459(4) 0.6661(3) 0.6653(5) 0.0420(10) Uani 1 1 d . . . . .
H5 H 0.610664 0.682751 0.642515 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4616(4) 0.6062(3) 0.5907(4) 0.0360(8) Uani 1 1 d . . . . .
H6 H 0.470407 0.581822 0.519611 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6295(5) 0.7672(4) 0.8523(6) 0.0601(15) Uani 1 1 d . . . . .
H7A H 0.707003 0.755026 0.846631 0.090 Uiso 1 1 calc R U . . .
H7B H 0.637353 0.763109 0.939530 0.090 Uiso 1 1 calc R U . . .
H7C H 0.603730 0.825135 0.821228 0.090 Uiso 1 1 calc R U . . .
C8 C 0.1946(3) 0.6249(2) 0.3282(3) 0.0279(7) Uani 1 1 d . . . . .
H8 H 0.264683 0.660927 0.378926 0.034 Uiso 1 1 calc R U . . .
C9 C 0.0922(4) 0.6840(3) 0.2384(4) 0.0328(8) Uani 1 1 d . . . . .
H9A H 0.126852 0.721607 0.191884 0.039 Uiso 1 1 calc R U . . .
H9B H 0.031215 0.647406 0.176822 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0296(4) 0.7404(3) 0.3046(4) 0.0319(8) Uani 1 1 d . . . . .
C11 C -0.0193(4) 0.6837(3) 0.3827(4) 0.0360(9) Uani 1 1 d . . . . .
H11A H -0.081590 0.644979 0.326916 0.043 Uiso 1 1 calc R U . . .
H11B H -0.056830 0.720052 0.427890 0.043 Uiso 1 1 calc R U . . .
C12 C 0.0818(4) 0.6302(3) 0.4771(4) 0.0354(8) Uani 1 1 d . . . . .
H12A H 0.139399 0.669118 0.538065 0.042 Uiso 1 1 calc R U . . .
H12B H 0.047209 0.592368 0.523499 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2306(3) 0.5666(2) 0.2394(4) 0.0297(7) Uani 1 1 d . . . . .
C14 C 0.1541(4) 0.5004(3) 0.1696(4) 0.0367(8) Uani 1 1 d . . . . .
H14 H 0.085050 0.485850 0.186002 0.044 Uiso 1 1 calc R U . . .
C15 C 0.1786(5) 0.4559(3) 0.0766(4) 0.0438(10) Uani 1 1 d . . . . .
H15 H 0.126907 0.411587 0.030442 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2820(5) 0.4782(3) 0.0527(4) 0.0433(10) Uani 1 1 d . . . . .
C17 C 0.3606(5) 0.5416(3) 0.1218(5) 0.0455(10) Uani 1 1 d . . . . .
H17 H 0.430533 0.554926 0.106278 0.055 Uiso 1 1 calc R U . . .
C18 C 0.3346(4) 0.5858(3) 0.2156(4) 0.0388(9) Uani 1 1 d . . . . .
H18 H 0.387776 0.628879 0.263154 0.047 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'
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 O1 119.3(2) . . ?
O2 S1 N1 107.64(17) . . ?
O1 S1 N1 106.19(18) . . ?
O2 S1 C1 108.35(19) . . ?
O1 S1 C1 108.72(19) . . ?
N1 S1 C1 105.86(17) . . ?
C12 N1 C8 114.7(3) . . ?
C12 N1 S1 110.4(2) . . ?
C8 N1 S1 115.5(2) . . ?
C2 C1 C6 120.6(4) . . ?
C2 C1 S1 120.2(3) . . ?
C6 C1 S1 119.2(3) . . ?
C3 C2 C1 119.2(4) . . ?
C2 C3 C4 121.1(4) . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 C7 120.0(5) . . ?
C3 C4 C7 121.6(5) . . ?
C6 C5 C4 121.3(4) . . ?
C5 C6 C1 119.3(4) . . ?
N1 C8 C13 113.7(3) . . ?
N1 C8 C9 109.7(3) . . ?
C13 C8 C9 104.6(3) . . ?
C10 C9 C8 114.6(3) . . ?
C11 C10 C9 109.5(3) . . ?
C11 C10 Cl1 110.8(3) . . ?
C9 C10 Cl1 110.7(3) . . ?
C11 C10 Br1 110.1(3) . . ?
C9 C10 Br1 109.3(3) . . ?
Cl1 C10 Br1 106.5(2) . . ?
C10 C11 C12 110.8(3) . . ?
N1 C12 C11 112.6(3) . . ?
C18 C13 C14 118.5(4) . . ?
C18 C13 C8 119.6(3) . . ?
C14 C13 C8 121.5(4) . . ?
C15 C14 C13 121.3(4) . . ?
C14 C15 C16 118.9(4) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 Cl2 120.1(4) . . ?
C15 C16 Cl2 118.6(4) . . ?
C16 C17 C18 119.1(4) . . ?
C13 C18 C17 121.0(4) . . ?
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 C10 1.928(4) . ?
Cl1 C10 1.824(4) . ?
Cl2 C16 1.748(5) . ?
S1 O2 1.429(3) . ?
S1 O1 1.430(3) . ?
S1 N1 1.669(3) . ?
S1 C1 1.767(4) . ?
N1 C12 1.493(5) . ?
N1 C8 1.498(5) . ?
C1 C2 1.387(6) . ?
C1 C6 1.390(6) . ?
C2 C3 1.384(6) . ?
C3 C4 1.397(7) . ?
C4 C5 1.386(7) . ?
C4 C7 1.509(6) . ?
C5 C6 1.383(6) . ?
C8 C13 1.522(5) . ?
C8 C9 1.546(5) . ?
C9 C10 1.508(5) . ?
C10 C11 1.503(6) . ?
C11 C12 1.509(5) . ?
C13 C18 1.385(6) . ?
C13 C14 1.389(6) . ?
C14 C15 1.375(6) . ?
C15 C16 1.390(7) . ?
C16 C17 1.367(7) . ?
C17 C18 1.390(6) . ?
