#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/98/2009820.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_2009820
loop_
_publ_author_name
'Sehgal, V.'
'Singh, P.'
'Dandia, A.'
'Bohra, R.'
_publ_section_title
;
 A spiro-indole derivative, C₁₆H₁₀ClFN₂O₂S
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1156
_journal_page_last               1159
_journal_paper_doi               10.1107/S0108270193012697
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C16 H10 Cl F N2 O2 S'
_chemical_formula_weight         348.79
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           'Frenz (1985)'
_cell_angle_alpha                90
_cell_angle_beta                 95.79(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2520(10)
_cell_length_b                   8.158(3)
_cell_length_c                   15.388(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      12
_cell_measurement_theta_min      5
_cell_volume                     1530.2(6)
_diffrn_measurement_device       Enraf-Nonius
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.081
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3100
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  30
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       Plates
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.213
_refine_diff_density_min         0.151
_refine_ls_extinction_method     none
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     248
_refine_ls_number_reflns         1627
_refine_ls_R_factor_obs          0.042
_refine_ls_shift/esd_max         0.06
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/σ(F²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.045
_reflns_number_observed          1627
_reflns_number_total             2913
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            ab1096.cif
_cod_data_source_block           ab1096_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/\s(F^2^)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s(F^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1530.2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C16 H10 Cl1 F1 N2 O2 S1'
_cod_database_code               2009820
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
Cl 1.10254(7) .23620(10) .57025(8)
S .65200(7) -.01730(10) .49155(6)
F .8638(3) .6476(3) .1675(2)
O(1) .4959(2) .3027(3) .4375(2)
O(2) .6215(2) -.0037(3) .2414(2)
N(1) .6393(2) .4193(3) .5244(2)
N(2) .6843(2) .1596(3) .3552(2)
C(1) .9662(3) .2997(5) .5564(2)
C(2) .9359(3) .4382(5) .5987(2)
C(3) .8276(3) .4867(4) .5922(2)
C(4) .7524(3) .3945(4) .5414(2)
C(5) .7831(2) .2573(4) .4975(2)
C(6) .8908(2) .2075(4) .5045(2)
C(7) .5913(3) .3081(4) .4683(2)
C(8) .6825(2) .1842(4) .4484(2)
C(9) .5902(3) -.0841(5) .3873(2)
C(10) .6324(3) .0247(4) .3187(2)
C(11) .7275(3) .2862(4) .3038(2)
C(12) .8316(3) .2690(4) .2785(2)
C(13) .8771(3) .3903(5) .2312(2)
C(14) .8165(4) .5249(5) .2120(2)
C(15) .7128(4) .5476(5) .2334(3)
C(16) .6666(3) .4244(5) .2803(2)
H(1) .605(2) .493(3) .542(2)
H(2) .992(3) .502(4) .634(2)
H(3) .807(2) .567(4) .620(2)
H(6) .915(2) .114(4) .476(2)
H(9a) .601(3) -.191(4) .374(2)
H(9b) .514(3) -.061(4) .385(2)
H(12) .871(2) .167(4) .296(2)
H(13) .950(3) .382(4) .212(2)
H(15) .677(3) .633(4) .218(2)
H(16) .593(2) .429(4) .294(2)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(8) S C(9) 91.8(2) yes
C(4) N(1) C(7) 112.5(3) yes
C(8) N(2) C(10) 117.8(3) yes
C(8) N(2) C(11) 119.2(2) yes
C(10) N(2) C(11) 122.6(3) yes
Cl C(1) C(2) 119.3(3) yes
Cl C(1) C(6) 119.1(3) yes
C(2) C(1) C(6) 121.7(4) no
C(1) C(2) C(3) 120.4(3) no
C(2) C(3) C(4) 118.1(3) no
N(1) C(4) C(3) 128.6(4) yes
N(1) C(4) C(5) 109.9(3) yes
S C(8) N(2) 105.0(2) yes
S C(8) C(5) 111.3(3) yes
S C(8) C(7) 109.6(3) yes
N(2) C(8) C(5) 117.3(2) yes
N(2) C(8) C(7) 111.5(2) yes
C(5) C(8) C(7) 102.2(2) yes
S C(9) C(10) 107.8(2) yes
O(2) C(10) N(2) 124.2(3) yes
O(2) C(10) C(9) 124.5(3) yes
N(2) C(10) C(9) 111.4(3) yes
N(2) C(11) C(12) 119.1(3) yes
N(2) C(11) C(16) 120.9(3) yes
C(3) C(4) C(5) 121.6(3) no
C(4) C(5) C(6) 120.6(3) no
C(4) C(5) C(8) 108.5(3) yes
C(6) C(5) C(8) 130.9(3) yes
C(1) C(6) C(5) 117.8(4) no
O(1) C(7) N(1) 127.9(3) yes
O(1) C(7) C(8) 125.4(3) yes
N(1) C(7) C(8) 106.7(2) yes
C(12) C(11) C(16) 120.1(3) no
C(11) C(12) C(13) 120.7(3) no
C(12) C(13) C(14) 117.3(4) no
F C(14) C(13) 117.0(4) yes
F C(14) C(15) 118.3(4) yes
C(13) C(14) C(15) 124.7(4) no
C(14) C(15) C(16) 117.8(4) no
C(11) C(16) C(15) 119.3(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C(1) 1.741(3) yes
S C(8) 1.825(3) yes
S C(9) 1.788(4) yes
F C(14) 1.374(5) yes
O(1) C(7) 1.217(4) yes
O(2) C(10) 1.206(4) yes
N(1) C(4) 1.399(4) yes
N(1) C(7) 1.347(5) yes
N(1) H(1) 0.80(3) no
N(2) C(8) 1.451(4) yes
N(2) C(10) 1.363(4) yes
N(2) C(11) 1.434(5) yes
C(1) C(2) 1.373(5) no
C(1) C(6) 1.383(4) no
C(2) C(3) 1.379(5) no
C(2) H(2) 0.99(3) no
C(3) C(4) 1.371(5) no
C(3) H(3) 0.84(3) no
C(4) C(5) 1.379(4) no
C(5) C(6) 1.374(4) no
C(5) C(8) 1.504(4) yes
C(6) H(6) 0.94(3) no
C(7) C(8) 1.561(4) yes
C(9) C(10) 1.510(6) yes
C(9) H(9a) 0.91(3) no
C(9) H(9b) 0.95(3) no
C(11) C(12) 1.378(5) no
C(11) C(16) 1.379(5) no
C(12) C(13) 1.379(5) no
C(12) H(12) 0.99(3) no
C(13) C(14) 1.341(6) no
C(13) H(13) 0.97(3) no
C(14) C(15) 1.358(6) no
C(15) C(16) 1.391(6) no
C(15) H(15) 0.85(4) no
C(16) H(16) 0.96(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057204
