#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:03:09 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257727 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/92/7059275.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_7059275
loop_
_publ_author_name
'Basu, Pallabita'
'Hazra, Chiranjit'
'Baiju, Thekke V.'
'Namboothiri, Irishi N. N.'
_publ_section_title
;
 Synthesis of tetrahydrothiopyrano[2,3-b]indoles via [3+3] annulation of
 nitroallylic acetates with indoline-2-thiones
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1389
_journal_page_last               1399
_journal_paper_doi               10.1039/C9NJ04754A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H15 Br N2 O2 S'
_chemical_formula_sum            'C18 H15 Br N2 O2 S'
_chemical_formula_weight         403.29
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_audit_update_record
;
2018-11-09 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.6557(7)
_cell_length_b                   29.6557(7)
_cell_length_c                   9.9045(3)
_cell_measurement_reflns_used    12972
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.1920
_cell_measurement_theta_min      2.2060
_cell_volume                     7543.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  70.00   0.50   16.00    --  -20.00  72.00  36.00  252
  2  ω    -25.00   5.00   0.50   16.00    --  -20.00   0.00  36.00   60
  3  ω   -109.50  14.00   0.50   16.00    --  -20.00 -72.00  36.00  247
  4  ω    -36.00  -6.00   0.50   16.00    --  -20.00  72.00 -36.00   60
  5  ω   -110.00 -13.00   0.50   16.00    --  -20.00 -72.00-108.00  194
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0217503000
_diffrn_orient_matrix_UB_12      -0.0228381000
_diffrn_orient_matrix_UB_13      0.0258594000
_diffrn_orient_matrix_UB_21      0.0120635000
_diffrn_orient_matrix_UB_22      -0.0146495000
_diffrn_orient_matrix_UB_23      -0.0177696000
_diffrn_orient_matrix_UB_31      0.0120570000
_diffrn_orient_matrix_UB_32      0.0051372000
_diffrn_orient_matrix_UB_33      0.0643415000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19509
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.983
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_min         2.204
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
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    1.598
_exptl_crystal_description       needle
_exptl_crystal_F_000             3672
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0279
_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)+(0.0307P)²+18.5528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2678
_reflns_number_total             2950
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04754a2.cif
_cod_data_source_block           INN-PB-86C-1_mo
_cod_depositor_comments          'Adding full bibliography for 7059275.cif.'
_cod_original_cell_volume        7543.6(4)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7059275
_chemical_oxdiff_formula         'C18 H15 Br N2 O2 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.
;
_reflns_odcompleteness_completeness 94.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.10
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C2(H2), C10(H10), C5(H5), C11(H11), C13(H13), C12(H12)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.548
_oxdiff_exptl_absorpt_empirical_full_min 0.667
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
Br1 Br 0.57593(2) 0.32405(2) 0.71767(2) 0.02703(9) Uani 1 1 d .
S1 S 0.54866(2) 0.55980(2) 0.34143(6) 0.02655(15) Uani 1 1 d .
O1 O 0.65560(7) 0.57145(7) 0.1258(2) 0.0380(5) Uani 1 1 d .
N1 N 0.48009(7) 0.48148(7) 0.17613(19) 0.0218(4) Uani 1 1 d .
C3 C 0.55099(9) 0.42247(9) 0.4734(2) 0.0217(5) Uani 1 1 d .
H3 H 0.5250 0.4310 0.4621 0.026 Uiso 1 1 calc R
C6 C 0.62752(9) 0.39587(9) 0.5048(2) 0.0230(5) Uani 1 1 d .
H6 H 0.6530 0.3866 0.5153 0.028 Uiso 1 1 calc R
C1 C 0.58400(9) 0.37432(8) 0.5865(2) 0.0217(5) Uani 1 1 d .
C2 C 0.54559(9) 0.38743(9) 0.5728(2) 0.0223(5) Uani 1 1 d .
H2 H 0.5167 0.3730 0.6294 0.027 Uiso 1 1 calc R
C10 C 0.52225(9) 0.39307(8) 0.0744(2) 0.0239(5) Uani 1 1 d .
H10 H 0.5511 0.3894 0.0904 0.029 Uiso 1 1 calc R
C8 C 0.55121(8) 0.47536(8) 0.2237(2) 0.0199(5) Uani 1 1 d .
C16 C 0.52656(8) 0.50320(9) 0.2452(2) 0.0208(5) Uani 1 1 d .
C5 C 0.63265(8) 0.43141(8) 0.4071(2) 0.0202(5) Uani 1 1 d .
H5 H 0.6620 0.4463 0.3521 0.024 Uiso 1 1 calc R
C7 C 0.60174(8) 0.48574(9) 0.2839(2) 0.0219(5) Uani 1 1 d .
H7 H 0.6235 0.4844 0.2112 0.026 Uiso 1 1 calc R
N2 N 0.65897(8) 0.58259(8) 0.2455(3) 0.0349(5) Uani 1 1 d .
C4 C 0.59452(8) 0.44526(8) 0.3900(2) 0.0197(5) Uani 1 1 d .
C18 C 0.63142(9) 0.54002(9) 0.3498(2) 0.0266(5) Uani 1 1 d .
H18 H 0.6582 0.5404 0.4086 0.032 Uiso 1 1 calc R
C15 C 0.44410(9) 0.50144(10) 0.1736(2) 0.0275(5) Uani 1 1 d .
H15A H 0.4230 0.4904 0.2535 0.041 Uiso 1 1 calc GR
H15B H 0.4222 0.4883 0.0953 0.041 Uiso 1 1 calc GR
H15C H 0.4634 0.5388 0.1702 0.041 Uiso 1 1 calc GR
C9 C 0.51813(8) 0.43329(8) 0.1358(2) 0.0205(5) Uani 1 1 d .
O2 O 0.68452(9) 0.62669(8) 0.2894(3) 0.0660(7) Uani 1 1 d .
C11 C 0.48301(10) 0.35891(9) -0.0102(3) 0.0308(6) Uani 1 1 d .
H11 H 0.4857 0.3323 -0.0520 0.037 Uiso 1 1 calc R
C13 C 0.43393(9) 0.40339(9) 0.0243(2) 0.0279(5) Uani 1 1 d .
H13 H 0.4048 0.4066 0.0080 0.033 Uiso 1 1 calc R
C17 C 0.59760(9) 0.55355(9) 0.4362(2) 0.0278(5) Uani 1 1 d .
H17A H 0.6198 0.5861 0.4827 0.033 Uiso 1 1 calc R
H17B H 0.5804 0.5267 0.5043 0.033 Uiso 1 1 calc R
C14 C 0.47392(9) 0.43821(9) 0.1086(2) 0.0220(5) Uani 1 1 d .
C12 C 0.43911(10) 0.36398(10) -0.0339(3) 0.0326(6) Uani 1 1 d .
H12 H 0.4129 0.3402 -0.0902 0.039 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'
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
C16 S1 C17 96.85(11)
C16 N1 C15 125.74(19)
C14 N1 C16 108.25(18)
C14 N1 C15 126.00(19)
C2 C3 H3 119.3
C2 C3 C4 121.3(2)
C4 C3 H3 119.3
C1 C6 H6 120.5
C1 C6 C5 119.0(2)
C5 C6 H6 120.5
C6 C1 Br1 119.08(17)
C6 C1 C2 121.6(2)
C2 C1 Br1 119.31(17)
C3 C2 C1 118.7(2)
C3 C2 H2 120.7
C1 C2 H2 120.7
C9 C10 H10 120.3
C11 C10 H10 120.3
C11 C10 C9 119.3(2)
C16 C8 C7 126.7(2)
C16 C8 C9 106.30(19)
C9 C8 C7 127.0(2)
N1 C16 S1 121.83(16)
C8 C16 S1 127.47(18)
C8 C16 N1 110.7(2)
C6 C5 H5 119.5
C6 C5 C4 120.9(2)
C4 C5 H5 119.5
C8 C7 H7 108.0
C8 C7 C4 112.35(18)
C8 C7 C18 111.99(18)
C4 C7 H7 108.0
C4 C7 C18 108.21(18)
C18 C7 H7 108.0
O1 N2 C18 120.0(2)
O2 N2 O1 124.0(2)
O2 N2 C18 116.0(2)
C3 C4 C5 118.5(2)
C3 C4 C7 121.47(19)
C5 C4 C7 120.0(2)
C7 C18 H18 107.4
N2 C18 C7 111.7(2)
N2 C18 H18 107.4
N2 C18 C17 108.45(19)
C17 C18 C7 114.03(19)
C17 C18 H18 107.4
N1 C15 H15A 109.5
N1 C15 H15B 109.5
N1 C15 H15C 109.5
H15A C15 H15B 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C10 C9 C8 133.9(2)
C10 C9 C14 119.0(2)
C14 C9 C8 106.98(19)
C10 C11 H11 119.7
C10 C11 C12 120.7(2)
C12 C11 H11 119.7
C14 C13 H13 121.2
C12 C13 H13 121.2
C12 C13 C14 117.7(2)
S1 C17 H17A 108.8
S1 C17 H17B 108.8
C18 C17 S1 113.78(17)
C18 C17 H17A 108.8
C18 C17 H17B 108.8
H17A C17 H17B 107.7
N1 C14 C9 107.79(19)
N1 C14 C13 130.5(2)
C13 C14 C9 121.7(2)
C11 C12 H12 119.2
C13 C12 C11 121.6(2)
C13 C12 H12 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.900(2)
S1 C16 1.748(2)
S1 C17 1.814(2)
O1 N2 1.222(3)
N1 C16 1.376(3)
N1 C15 1.457(3)
N1 C14 1.376(3)
C3 H3 0.9300
C3 C2 1.381(3)
C3 C4 1.391(3)
C6 H6 0.9300
C6 C1 1.380(3)
C6 C5 1.382(3)
C1 C2 1.382(3)
C2 H2 0.9300
C10 H10 0.9300
C10 C9 1.398(3)
C10 C11 1.380(3)
C8 C16 1.366(3)
C8 C7 1.495(3)
C8 C9 1.433(3)
C5 H5 0.9300
C5 C4 1.393(3)
C7 H7 0.9800
C7 C4 1.527(3)
C7 C18 1.541(3)
N2 C18 1.515(3)
N2 O2 1.217(3)
C18 H18 0.9800
C18 C17 1.517(3)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C9 C14 1.416(3)
C11 H11 0.9300
C11 C12 1.403(4)
C13 H13 0.9300
C13 C14 1.395(3)
C13 C12 1.379(4)
C17 H17A 0.9700
C17 H17B 0.9700
C12 H12 0.9300
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
Br1 C1 C2 C3 -177.43(16)
O1 N2 C18 C7 0.3(3)
O1 N2 C18 C17 -126.2(2)
C6 C1 C2 C3 0.9(3)
C6 C5 C4 C3 0.0(3)
C6 C5 C4 C7 178.3(2)
C1 C6 C5 C4 -0.4(3)
C2 C3 C4 C5 1.0(3)
C2 C3 C4 C7 -177.4(2)
C10 C9 C14 N1 -177.66(19)
C10 C9 C14 C13 1.3(3)
C10 C11 C12 C13 1.0(4)
C8 C7 C4 C3 -34.2(3)
C8 C7 C4 C5 147.5(2)
C8 C7 C18 N2 -78.5(2)
C8 C7 C18 C17 44.9(3)
C8 C9 C14 N1 0.4(2)
C8 C9 C14 C13 179.4(2)
C16 S1 C17 C18 46.12(19)
C16 N1 C14 C9 -0.5(2)
C16 N1 C14 C13 -179.4(2)
C16 C8 C7 C4 108.4(2)
C16 C8 C7 C18 -13.6(3)
C16 C8 C9 C10 177.5(2)
C16 C8 C9 C14 -0.1(2)
C5 C6 C1 Br1 178.32(16)
C5 C6 C1 C2 0.0(3)
C7 C8 C16 S1 3.3(3)
C7 C8 C16 N1 -178.2(2)
C7 C8 C9 C10 -4.4(4)
C7 C8 C9 C14 177.9(2)
C7 C18 C17 S1 -65.6(2)
N2 C18 C17 S1 59.6(2)
C4 C3 C2 C1 -1.4(3)
C4 C7 C18 N2 157.12(18)
C4 C7 C18 C17 -79.5(2)
C18 C7 C4 C3 90.0(2)
C18 C7 C4 C5 -88.3(2)
C15 N1 C16 S1 -0.2(3)
C15 N1 C16 C8 -178.7(2)
C15 N1 C14 C9 178.6(2)
C15 N1 C14 C13 -0.2(4)
C9 C10 C11 C12 -0.6(3)
C9 C8 C16 S1 -178.60(17)
C9 C8 C16 N1 -0.2(2)
C9 C8 C7 C4 -69.3(3)
C9 C8 C7 C18 168.7(2)
O2 N2 C18 C7 -178.2(2)
O2 N2 C18 C17 55.3(3)
C11 C10 C9 C8 -178.0(2)
C11 C10 C9 C14 -0.6(3)
C17 S1 C16 N1 164.15(19)
C17 S1 C16 C8 -17.6(2)
C14 N1 C16 S1 178.95(16)
C14 N1 C16 C8 0.4(2)
C14 C13 C12 C11 -0.2(4)
C12 C13 C14 N1 177.8(2)
C12 C13 C14 C9 -0.9(3)
