#------------------------------------------------------------------------------
#$Date: 2022-11-05 05:44:00 +0200 (Sat, 05 Nov 2022) $
#$Revision: 278950 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/09/7130957.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_7130957
loop_
_publ_author_name
'Sharma, Alpa'
'Kour, Harpreet'
'Kour, Jaspreet'
'Kamal, ?'
'Sawant, Sanghapal D.'
_publ_section_title
;
 Visible-light-promoted iron-catalyzed C-H functionalization of
 1,4-naphthoquinones via oxidative coupling with sulfoximines.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11312
_journal_page_last               11315
_journal_paper_doi               10.1039/d2cc03319d
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C17 H12 N2 O5 S'
_chemical_formula_sum            'C17 H12 N2 O5 S'
_chemical_formula_weight         356.35
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-08-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.04.25 svn.r3594 for OlexSys, GUI svn.r5751)
;
_audit_update_record
;
2022-08-03 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.565(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.173(3)
_cell_length_b                   5.3337(15)
_cell_length_c                   25.755(7)
_cell_measurement_reflns_used    8464
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.51
_cell_volume                     1527.6(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      108.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            43547
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.7313
_exptl_absorpt_correction_T_min  0.6265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1584 before and 0.1125 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic greenish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0397P)²+1.0782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                3479
_reflns_number_total             3797
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc03319d2.cif
_cod_data_source_block           5n
_cod_database_code               7130957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S001 S 0.49351(3) -0.04357(6) 0.396688(13) 0.01619(10) Uani 1 d . . .
O002 O 0.32146(9) 0.54857(19) 0.46590(4) 0.0187(2) Uani 1 d . . .
O003 O 0.44212(10) -0.2405(2) 0.36262(4) 0.0217(2) Uani 1 d . . .
O004 O 0.11091(10) 0.6570(2) 0.50980(4) 0.0262(2) Uani 1 d . . .
O005 O 0.15487(10) 0.3567(2) 0.26967(4) 0.0262(2) Uani 1 d . . .
O006 O 0.15191(11) 1.0484(2) 0.49695(5) 0.0293(3) Uani 1 d . . .
N9 N 0.12559(11) 0.8359(2) 0.48167(5) 0.0198(2) Uani 1 d . . .
N008 N 0.41004(11) 0.1409(2) 0.42323(5) 0.0184(2) Uani 1 d . . .
C009 C 0.27224(12) 0.4831(3) 0.42417(5) 0.0153(3) Uani 1 d . . .
C00A C 0.32185(12) 0.2705(3) 0.39383(5) 0.0159(3) Uani 1 d . . .
C00B C 0.16514(12) 0.6196(3) 0.39896(5) 0.0158(3) Uani 1 d . . .
C00C C 0.13100(12) 0.5884(3) 0.34569(5) 0.0170(3) Uani 1 d . . .
C00D C 0.10328(12) 0.8011(3) 0.42483(5) 0.0179(3) Uani 1 d . . .
C00E C 0.59486(12) 0.1291(3) 0.36155(6) 0.0184(3) Uani 1 d . . .
C00F C 0.27954(13) 0.2335(3) 0.34321(5) 0.0184(3) Uani 1 d . . .
H00F H 0.3117 0.0989 0.3248 0.022 Uiso 1 calc . . R
C00G C 0.18822(13) 0.3886(3) 0.31608(5) 0.0182(3) Uani 1 d . . .
C00H C 0.01541(13) 0.9530(3) 0.39979(6) 0.0217(3) Uani 1 d . . .
H00H H -0.0237 1.0768 0.4186 0.026 Uiso 1 calc . . R
C00I C 0.04235(13) 0.7378(3) 0.31983(6) 0.0213(3) Uani 1 d . . .
H00I H 0.0207 0.7142 0.2836 0.026 Uiso 1 calc . . R
C00J C 0.58702(14) 0.1057(3) 0.30773(6) 0.0247(3) Uani 1 d . . .
H00J H 0.5317 -0.0081 0.2901 0.030 Uiso 1 calc . . R
C00K C 0.58054(13) -0.1714(3) 0.45032(6) 0.0213(3) Uani 1 d . . .
H00A H 0.5316 -0.2887 0.4685 0.032 Uiso 1 calc . . GR
H00B H 0.6094 -0.0366 0.4742 0.032 Uiso 1 calc . . GR
H00C H 0.6494 -0.2605 0.4383 0.032 Uiso 1 calc . . GR
C00L C 0.67730(14) 0.2881(3) 0.38838(6) 0.0237(3) Uani 1 d . . .
H00L H 0.6822 0.2995 0.4253 0.028 Uiso 1 calc . . R
C00M C -0.01464(14) 0.9209(3) 0.34653(6) 0.0234(3) Uani 1 d . . .
H00M H -0.0742 1.0243 0.3285 0.028 Uiso 1 calc . . R
C00N C 0.74320(15) 0.4148(3) 0.30621(7) 0.0318(4) Uani 1 d . . .
H00N H 0.7931 0.5165 0.2870 0.038 Uiso 1 calc . . R
C00O C 0.75251(16) 0.4303(3) 0.36027(7) 0.0306(4) Uani 1 d . . .
H00O H 0.8104 0.5384 0.3780 0.037 Uiso 1 calc . . R
C00P C 0.66200(15) 0.2528(3) 0.28011(7) 0.0302(4) Uani 1 d . . .
H00P H 0.6572 0.2415 0.2432 0.036 Uiso 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'
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
O003 S001 N008 120.25(7) . . ?
O003 S001 C00E 107.57(7) . . ?
O003 S001 C00K 110.66(7) . . ?
N008 S001 C00E 109.54(7) . . ?
N008 S001 C00K 102.13(7) . . ?
C00K S001 C00E 105.78(7) . . ?
O004 N9 O006 125.08(13) . . ?
O004 N9 C00D 118.22(12) . . ?
O006 N9 C00D 116.60(12) . . ?
C00A N008 S001 120.32(10) . . ?
O002 C009 C00A 121.16(12) . . ?
O002 C009 C00B 121.39(13) . . ?
C00B C009 C00A 117.33(12) . . ?
N008 C00A C009 111.87(11) . . ?
C00F C00A N008 128.49(13) . . ?
C00F C00A C009 119.61(12) . . ?
C00C C00B C009 119.94(12) . . ?
C00D C00B C009 122.91(12) . . ?
C00D C00B C00C 116.78(12) . . ?
C00B C00C C00G 119.85(12) . . ?
C00I C00C C00B 121.06(13) . . ?
C00I C00C C00G 119.09(12) . . ?
C00B C00D N9 121.20(12) . . ?
C00H C00D N9 115.70(12) . . ?
C00H C00D C00B 123.06(13) . . ?
C00J C00E S001 118.80(12) . . ?
C00J C00E C00L 121.88(14) . . ?
C00L C00E S001 119.29(11) . . ?
C00A C00F H00F 118.4 . . ?
C00A C00F C00G 123.15(13) . . ?
C00G C00F H00F 118.4 . . ?
O005 C00G C00C 119.48(13) . . ?
O005 C00G C00F 121.74(13) . . ?
C00F C00G C00C 118.77(12) . . ?
C00D C00H H00H 120.7 . . ?
C00D C00H C00M 118.70(14) . . ?
C00M C00H H00H 120.7 . . ?
C00C C00I H00I 119.8 . . ?
C00M C00I C00C 120.47(13) . . ?
C00M C00I H00I 119.8 . . ?
C00E C00J H00J 120.7 . . ?
C00E C00J C00P 118.51(15) . . ?
C00P C00J H00J 120.7 . . ?
S001 C00K H00A 109.5 . . ?
S001 C00K H00B 109.5 . . ?
S001 C00K H00C 109.5 . . ?
H00A C00K H00B 109.5 . . ?
H00A C00K H00C 109.5 . . ?
H00B C00K H00C 109.5 . . ?
C00E C00L H00L 120.6 . . ?
C00E C00L C00O 118.75(15) . . ?
C00O C00L H00L 120.6 . . ?
C00H C00M H00M 120.1 . . ?
C00I C00M C00H 119.88(13) . . ?
C00I C00M H00M 120.1 . . ?
C00O C00N H00N 119.7 . . ?
C00P C00N H00N 119.7 . . ?
C00P C00N C00O 120.52(15) . . ?
C00L C00O C00N 120.04(16) . . ?
C00L C00O H00O 120.0 . . ?
C00N C00O H00O 120.0 . . ?
C00J C00P H00P 119.9 . . ?
C00N C00P C00J 120.25(16) . . ?
C00N C00P H00P 119.9 . . ?
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
S001 O003 1.4508(11) . ?
S001 N008 1.5586(12) . ?
S001 C00E 1.7744(15) . ?
S001 C00K 1.7485(15) . ?
O002 C009 1.2104(17) . ?
O004 N9 1.2186(17) . ?
O005 C00G 1.2290(17) . ?
O006 N9 1.2262(17) . ?
N9 C00D 1.4726(18) . ?
N008 C00A 1.3701(17) . ?
C009 C00A 1.5125(19) . ?
C009 C00B 1.4943(19) . ?
C00A C00F 1.3573(19) . ?
C00B C00C 1.3980(19) . ?
C00B C00D 1.3956(19) . ?
C00C C00G 1.4900(19) . ?
C00C C00I 1.390(2) . ?
C00D C00H 1.383(2) . ?
C00E C00J 1.386(2) . ?
C00E C00L 1.386(2) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.4406(19) . ?
C00H H00H 0.9500 . ?
C00H C00M 1.391(2) . ?
C00I H00I 0.9500 . ?
C00I C00M 1.384(2) . ?
C00J H00J 0.9500 . ?
C00J C00P 1.392(2) . ?
C00K H00A 0.9800 . ?
C00K H00B 0.9800 . ?
C00K H00C 0.9800 . ?
C00L H00L 0.9500 . ?
C00L C00O 1.387(2) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00O 1.389(3) . ?
C00N C00P 1.379(3) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
