#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:55:58 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234318 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/61/4036154.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_4036154
loop_
_publ_author_name
'Debnath, Sudarshan'
'Mondal, Shovan'
_publ_section_title
;
 One-pot Sonogashira coupling-cyclization toward regioselective synthesis
 of benzosultams.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3940
_journal_page_last               3948
_journal_paper_doi               10.1021/acs.joc.5b00274
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C20 H14 N2 O4 S'
_chemical_formula_weight         378.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 114.145(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.7389(10)
_cell_length_b                   8.0887(3)
_cell_length_c                   21.7176(9)
_cell_measurement_temperature    296(2)
_cell_volume                     3965.6(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            59359
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         1.804
_exptl_absorpt_coefficient_mu    0.190
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             1568
_refine_diff_density_max         2.399
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.544
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.544
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.1039
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.3104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3189
_refine_ls_wR_factor_ref         0.3388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3492
_reflns_number_total             4550
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5b00274_si_002.cif
_cod_data_source_block           SMSD1oaa_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036154
_shelx_shelxl_version_number     2014/7
_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S001 S 0.31031(4) 0.85249(12) 0.14781(5) 0.0348(4) Uani 1 1 d
O002 O 0.32865(14) 0.8378(4) 0.09366(15) 0.0500(8) Uani 1 1 d
O003 O 0.31010(13) 1.0115(3) 0.17557(16) 0.0465(8) Uani 1 1 d
N004 N 0.35414(14) 0.7352(4) 0.21146(15) 0.0329(7) Uani 1 1 d
C1 C 0.43383(17) 0.8023(5) 0.3474(2) 0.0397(9) Uani 1 1 d
C006 C 0.38582(16) 0.6013(5) 0.19917(19) 0.0324(8) Uani 1 1 d
C007 C 0.38237(17) 0.7092(5) 0.33278(19) 0.0345(8) Uani 1 1 d
O008 O 0.5090(2) 0.2298(6) 0.1327(3) 0.0914(15) Uani 1 1 d
C009 C 0.27650(18) 0.7084(5) 0.2504(2) 0.0377(9) Uani 1 1 d
C00A C 0.22990(17) 0.7057(5) 0.18264(19) 0.0357(9) Uani 1 1 d
C00B C 0.33417(16) 0.7153(5) 0.26463(18) 0.0314(8) Uani 1 1 d
C00C C 0.24206(17) 0.7607(5) 0.1281(2) 0.0355(9) Uani 1 1 d
C00D C 0.4780(2) 0.8041(6) 0.4131(2) 0.0520(12) Uani 1 1 d
N2 N 0.4733(2) 0.2017(6) 0.1560(3) 0.0717(13) Uani 1 1 d
C00F C 0.4569(2) 0.5001(6) 0.1588(2) 0.0482(11) Uani 1 1 d
C00G C 0.42798(19) 0.6297(5) 0.1731(2) 0.0425(10) Uani 1 1 d
C00H C 0.4433(2) 0.3426(6) 0.1717(3) 0.0498(11) Uani 1 1 d
C00I C 0.1319(2) 0.6368(7) 0.1019(3) 0.0569(13) Uani 1 1 d
C00J C 0.37388(19) 0.4405(5) 0.2124(2) 0.0448(10) Uani 1 1 d
C00K C 0.17355(19) 0.6462(6) 0.1676(2) 0.0488(11) Uani 1 1 d
C00L C 0.2011(2) 0.7503(6) 0.0612(2) 0.0474(11) Uani 1 1 d
C00M C 0.2971(3) 0.5997(8) 0.5362(3) 0.0768(19) Uani 1 1 d
C00N C 0.1453(2) 0.6869(7) 0.0485(3) 0.0577(13) Uani 1 1 d
C00O C 0.3762(2) 0.6168(7) 0.3838(2) 0.0536(12) Uani 1 1 d
C00P C 0.4706(2) 0.7136(7) 0.4630(2) 0.0611(14) Uani 1 1 d
C00Q C 0.4032(2) 0.3096(6) 0.1990(3) 0.0537(12) Uani 1 1 d
C00R C 0.4201(3) 0.6198(8) 0.4475(3) 0.0710(16) Uani 1 1 d
O1 O 0.4629(4) 0.0647(6) 0.1694(5) 0.152(3) Uani 1 1 d
C00T C 0.2416(4) 0.6344(10) 0.5558(4) 0.120(4) Uani 1 1 d
C00U C 0.3114(5) 0.7222(15) 0.4903(7) 0.154(5) Uani 1 1 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 0.0000 0.0000 '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_3
O003 S001 O002 118.8(2) .
O003 S001 N004 106.16(17) .
O002 S001 N004 108.57(18) .
O003 S001 C00C 108.73(19) .
O002 S001 C00C 111.50(19) .
N004 S001 C00C 101.52(17) .
C006 N004 C00B 117.5(3) .
C006 N004 S001 120.0(3) .
C00B N004 S001 114.2(2) .
C00D C1 C007 119.7(4) .
C00J C006 C00G 119.7(4) .
C00J C006 N004 119.6(3) .
C00G C006 N004 120.7(3) .
C00O C007 C1 119.6(4) .
C00O C007 C00B 120.6(4) .
C1 C007 C00B 119.8(3) .
C00B C009 C00A 124.6(4) .
C00K C00A C00C 117.0(4) .
C00K C00A C009 123.4(4) .
C00C C00A C009 119.6(3) .
C009 C00B N004 120.4(3) .
C009 C00B C007 125.6(3) .
N004 C00B C007 114.0(3) .
C00L C00C C00A 123.0(4) .
C00L C00C S001 120.3(3) .
C00A C00C S001 116.7(3) .
C00P C00D C1 119.7(4) .
O1 N2 O008 122.9(5) .
O1 N2 C00H 118.6(5) .
O008 N2 C00H 118.5(5) .
C00G C00F C00H 117.9(4) .
C00F C00G C006 120.7(4) .
C00Q C00H C00F 123.2(4) .
C00Q C00H N2 118.1(4) .
C00F C00H N2 118.6(4) .
C00K C00I C00N 120.9(4) .
C00Q C00J C006 120.0(4) .
C00I C00K C00A 121.2(4) .
C00N C00L C00C 118.0(4) .
C00U C00M C00T 120.0(5) .
C00L C00N C00I 119.9(4) .
C00R C00O C007 119.6(5) .
C00R C00P C00D 119.9(4) .
C00H C00Q C00J 118.5(4) .
C00O C00R C00P 121.5(5) .
C00M C00T C00U 119.2(6) 7_566
C00M C00U C00T 118.9(6) 7_566
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S001 O003 1.422(3) .
S001 O002 1.428(3) .
S001 N004 1.662(3) .
S001 C00C 1.730(4) .
N004 C006 1.424(5) .
N004 C00B 1.439(5) .
C1 C00D 1.399(6) .
C1 C007 1.399(6) .
C006 C00J 1.390(5) .
C006 C00G 1.395(5) .
C007 C00O 1.396(6) .
C007 C00B 1.473(5) .
O008 N2 1.205(6) .
C009 C00B 1.332(6) .
C009 C00A 1.452(5) .
C00A C00K 1.382(6) .
C00A C00C 1.409(6) .
C00C C00L 1.392(6) .
C00D C00P 1.381(7) .
N2 O1 1.200(7) .
N2 C00H 1.475(6) .
C00F C00G 1.374(6) .
C00F C00H 1.376(7) .
C00H C00Q 1.372(7) .
C00I C00K 1.380(7) .
C00I C00N 1.391(7) .
C00J C00Q 1.380(6) .
C00L C00N 1.390(7) .
C00M C00U 1.545(15) .
C00M C00T 1.619(13) .
C00O C00R 1.366(7) .
C00P C00R 1.381(8) .
C00T C00U 1.731(15) 7_566
C00U C00T 1.731(15) 7_566
