#------------------------------------------------------------------------------
#$Date: 2022-03-22 01:14:23 +0200 (Tue, 22 Mar 2022) $
#$Revision: 273877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/66/1566670.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_1566670
loop_
_publ_author_name
'Nguyen, Vu T.'
'Haug, Graham C.'
'Nguyen, Viet D.'
'Vuong, Ngan T. H.'
'Karki, Guna B.'
'Arman, Hadi'
'Larionov, Oleg V.'
_publ_section_title
;
 Functional Group Divergence and the Structural Basis of Acridine
 Photocatalysis Revealed by Direct Decarboxysulfonylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00789D
_journal_year                    2022
_chemical_formula_moiety         'C15 H20 Cl N O3 S'
_chemical_formula_sum            'C15 H20 Cl N O3 S'
_chemical_formula_weight         329.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                89.487(2)
_cell_angle_beta                 85.132(2)
_cell_angle_gamma                82.136(2)
_cell_formula_units_Z            2
_cell_length_a                   5.01880(10)
_cell_length_b                   9.6241(2)
_cell_length_c                   16.1198(4)
_cell_measurement_reflns_used    7974
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.2340
_cell_measurement_theta_min      2.7280
_cell_volume                     768.50(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  95.00   0.50    0.05    --   46.62-125.00 152.00  122
  2  ω     34.00 111.00   0.50    0.05    --  106.69-125.00 152.00  154
  3  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00   0.00  134
  4  ω     45.00 126.00   0.50    0.05    --  106.69-145.00 -15.00  162
  5  ω     45.00 107.00   0.50    0.05    --   46.62-145.00 -15.00  124
  6  ω     34.00 111.00   0.50    0.05    --  106.69-125.00-120.00  154
  7  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00-150.00  134
  8  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 -30.00  142
  9  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00   0.00  142
 10  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 11  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00 150.00  134
 12  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
 13  ω    101.00 178.00   0.50    0.05    --  106.69  77.00-150.00  154
 14  ω     95.00 178.00   0.50    0.05    --  106.69 125.00-129.00  166
 15  ω     91.00 178.00   0.50    0.05    --  106.69  30.00-180.00  174
 16  ω     81.00 170.00   0.50    0.05    --  106.69 145.00  37.00  178
 17  ω    101.00 178.00   0.50    0.05    --  106.69  77.00  90.00  154
 18  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00   0.00   70
 19  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00  30.00   70
 20  ω    -71.00 -15.00   0.50    0.05    --  -88.50  61.00  90.00  112
 21  ω   -101.00 -23.00   0.50    0.05    --  -46.62 145.00  37.00  156
 22  ω    -86.00 -15.00   0.50    0.05    --  -88.50 125.00-129.00  142
 23  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-180.00   70
 24  ω    -86.00 -13.00   0.50    0.05    --  -46.62 125.00-129.00  146
 25  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 -60.00  176
 26  ω   -119.00 -60.00   0.50    0.05    --  -46.62-145.00 -15.00  118
 27  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 120.00   72
 28  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 150.00   72
 29  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 120.00  176
 30  ω   -119.00 -73.00   0.50    0.05    --  -46.62-125.00 152.00   92
 31  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-120.00   72
 32  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-180.00   72
 33  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00-150.00  176
 34  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 -90.00   72
 35  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 -90.00  176
 36  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00  30.00  176
 37  ω   -120.00 -52.00   0.50    0.05    --  -46.62 -37.00  60.00  136
 38  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00  60.00   72
 39  ω   -152.00 -60.00   0.50    0.05    --  -88.50-145.00 -15.00  184
 40  ω   -160.00 -91.00   0.50    0.05    --  -88.50 -61.00  30.00  138
 41  ω   -160.00-100.00   0.50    0.05    --  -88.50 -94.00   0.00  120
 42  ω   -163.00 -73.00   0.50    0.05    --  -88.50 -30.00-150.00  180
 43  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-180.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0131563000
_diffrn_orient_matrix_UB_12      -0.0240891000
_diffrn_orient_matrix_UB_13      -0.0938319000
_diffrn_orient_matrix_UB_21      0.0956847000
_diffrn_orient_matrix_UB_22      0.1433082000
_diffrn_orient_matrix_UB_23      -0.0187491000
_diffrn_orient_matrix_UB_31      0.2956050000
_diffrn_orient_matrix_UB_32      -0.0706753000
_diffrn_orient_matrix_UB_33      -0.0066266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14635
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.472
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.554
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2859
_reflns_number_total             3083
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd124
_cod_database_code               1566670
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Cl'
_chemical_oxdiff_usercomment     VNY138-13
_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.
;
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.538
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C8(H8A,H8B), C13(H13A,H13B), C9(H9A,H9B), C11(H11A,H11B),
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C14(H14), C2(H2)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.743
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 1.29108(8) 0.08561(4) 0.70567(2) 0.01878(12) Uani 1 1 d . . . . .
Cl1 Cl -0.35633(8) 0.30700(4) 0.02985(2) 0.02364(12) Uani 1 1 d . . . . .
O3 O 1.4890(2) -0.02547(12) 0.66924(8) 0.0258(3) Uani 1 1 d . . . . .
O1 O 0.3682(2) 0.56813(12) 0.30473(8) 0.0239(3) Uani 1 1 d . . . . .
O2 O 1.0367(2) 0.04602(13) 0.73893(8) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.5094(3) 0.34107(15) 0.32986(9) 0.0198(3) Uani 1 1 d . . . . .
C7 C 0.3664(3) 0.44256(17) 0.28850(10) 0.0187(3) Uani 1 1 d . . . . .
C6 C -0.0404(3) 0.23780(17) 0.15535(11) 0.0206(3) Uani 1 1 d . . . . .
H6 H -0.086307 0.145917 0.150114 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1288(3) 0.26675(17) 0.21512(10) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.198755 0.194293 0.250897 0.023 Uiso 1 1 calc R U . . .
C3 C 0.0941(3) 0.50623(18) 0.16925(11) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.141379 0.597985 0.173692 0.025 Uiso 1 1 calc R U . . .
C12 C 1.2239(3) 0.21944(17) 0.63106(11) 0.0204(3) Uani 1 1 d . . . . .
H12A H 1.106676 0.300356 0.658129 0.025 Uiso 1 1 calc R U . . .
H12B H 1.395502 0.251664 0.609394 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1962(3) 0.40190(17) 0.22276(10) 0.0182(3) Uani 1 1 d . . . . .
C14 C 1.4477(4) 0.08091(18) 0.86217(11) 0.0240(4) Uani 1 1 d . . . . .
H14 H 1.596680 0.008935 0.864479 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6796(3) 0.37711(17) 0.39318(10) 0.0197(3) Uani 1 1 d . . . . .
H8A H 0.568946 0.440519 0.434696 0.024 Uiso 1 1 calc R U . . .
H8B H 0.822677 0.428129 0.366681 0.024 Uiso 1 1 calc R U . . .
C13 C 1.4331(3) 0.17088(17) 0.78603(11) 0.0214(3) Uani 1 1 d . . . . .
H13A H 1.616562 0.189972 0.766034 0.026 Uiso 1 1 calc R U . . .
H13B H 1.320722 0.261715 0.799997 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8096(3) 0.24854(17) 0.43729(10) 0.0204(3) Uani 1 1 d . . . . .
H9A H 0.928199 0.187132 0.396514 0.025 Uiso 1 1 calc R U . . .
H9B H 0.667620 0.194944 0.461931 0.025 Uiso 1 1 calc R U . . .
C1 C -0.1411(3) 0.34405(18) 0.10366(10) 0.0194(3) Uani 1 1 d . . . . .
C2 C -0.0752(3) 0.47903(18) 0.10957(11) 0.0221(4) Uani 1 1 d . . . . .
H2 H -0.144780 0.551108 0.073475 0.027 Uiso 1 1 calc R U . . .
C11 C 1.0857(3) 0.16747(17) 0.55886(11) 0.0211(3) Uani 1 1 d . . . . .
H11A H 0.936069 0.116722 0.580855 0.025 Uiso 1 1 calc R U . . .
H11B H 1.216703 0.101459 0.524062 0.025 Uiso 1 1 calc R U . . .
C10 C 0.9753(3) 0.29103(17) 0.50584(10) 0.0203(3) Uani 1 1 d . . . . .
H10A H 1.128155 0.335766 0.480026 0.024 Uiso 1 1 calc R U . . .
H10B H 0.860729 0.361449 0.542398 0.024 Uiso 1 1 calc R U . . .
C15 C 1.2654(4) 0.0964(2) 0.92580(12) 0.0291(4) Uani 1 1 d . . . . .
H15A H 1.277(4) 0.038(2) 0.9764(15) 0.035 Uiso 1 1 d . U . . .
H1 H 0.516(5) 0.257(3) 0.3167(14) 0.035 Uiso 1 1 d . U . . .
H15B H 1.112(5) 0.165(2) 0.9259(14) 0.035 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 4 0.0854
3 2 -2 0.0640
0 6 -4 0.0882
-3 -3 3 0.0476
3 -2 0 0.0972
0 -3 -9 0.0331
-3 2 1 0.0510
0 3 10 0.0227
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
O3 S1 C12 109.61(8) . . ?
O3 S1 C13 109.55(8) . . ?
O2 S1 O3 116.63(8) . . ?
O2 S1 C12 107.96(8) . . ?
O2 S1 C13 108.49(8) . . ?
C12 S1 C13 103.83(8) . . ?
C7 N1 C8 120.08(14) . . ?
O1 C7 N1 121.24(15) . . ?
O1 C7 C4 119.99(14) . . ?
N1 C7 C4 118.76(14) . . ?
C1 C6 C5 119.34(15) . . ?
C6 C5 C4 120.30(15) . . ?
C2 C3 C4 121.31(16) . . ?
C11 C12 S1 111.39(11) . . ?
C5 C4 C7 123.24(15) . . ?
C3 C4 C7 117.69(14) . . ?
C3 C4 C5 119.03(15) . . ?
C15 C14 C13 123.31(17) . . ?
N1 C8 C9 112.27(13) . . ?
C14 C13 S1 110.49(12) . . ?
C8 C9 C10 110.68(13) . . ?
C6 C1 Cl1 118.91(13) . . ?
C6 C1 C2 121.46(15) . . ?
C2 C1 Cl1 119.63(13) . . ?
C3 C2 C1 118.56(15) . . ?
C12 C11 C10 110.22(13) . . ?
C11 C10 C9 113.15(13) . . ?
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
S1 O3 1.4476(13) . ?
S1 O2 1.4407(13) . ?
S1 C12 1.7723(17) . ?
S1 C13 1.7877(17) . ?
Cl1 C1 1.7438(16) . ?
O1 C7 1.240(2) . ?
N1 C7 1.338(2) . ?
N1 C8 1.458(2) . ?
C7 C4 1.503(2) . ?
C6 C5 1.391(2) . ?
C6 C1 1.382(2) . ?
C5 C4 1.397(2) . ?
C3 C4 1.391(2) . ?
C3 C2 1.386(2) . ?
C12 C11 1.526(2) . ?
C14 C13 1.497(2) . ?
C14 C15 1.311(3) . ?
C8 C9 1.518(2) . ?
C9 C10 1.529(2) . ?
C1 C2 1.390(2) . ?
C11 C10 1.528(2) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.3743 -5.6990 3.5739 -0.2030 -0.8479 0.4897
3.0406 1.8582 -2.4648 0.1465 0.6034 0.7838
0.0489 5.7779 -3.7993 0.2167 0.9039 -0.3687
-2.9100 -2.5229 2.8459 -0.1680 -0.6933 -0.7008
2.9120 -1.9699 0.0095 0.0082 -0.0038 1.0000
0.0457 -2.8130 -9.2497 0.9351 -0.2253 0.2736
-2.7620 2.2934 1.4039 -0.1506 0.0381 -0.9879
0.3191 2.6446 9.5115 -0.9604 0.2312 -0.1556
