#------------------------------------------------------------------------------
#$Date: 2021-10-02 01:15:17 +0300 (Sat, 02 Oct 2021) $
#$Revision: 269438 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564792.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_1564792
loop_
_publ_author_name
'Guan, Zhipeng'
'Zhu, Shuxiang'
'Yang, Yankai'
'Liu, Yanlong'
'Wang, Siyuan'
'Bu, Faxiang'
'Cong, Hengjiang'
'Alhumade, Hesham'
'Zhang, Heng'
'Lei, Aiwen'
_publ_section_title
;
 Electrochemically Selective Double C(sp2)-X (X=S/Se, N) Bonds Formation
 of One Carbon
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04475C
_journal_year                    2021
_chemical_formula_moiety         'C17 H15 Cl N4 O2 S'
_chemical_formula_sum            'C17 H15 Cl N4 O2 S'
_chemical_formula_weight         374.84
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc27r9r2
_audit_creation_date             2021-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-16 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                102.235(2)
_cell_angle_beta                 107.273(2)
_cell_angle_gamma                99.656(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7386(2)
_cell_length_b                   11.0939(2)
_cell_length_c                   11.2012(3)
_cell_measurement_reflns_used    12503
_cell_measurement_temperature    297.46(12)
_cell_measurement_theta_max      65.1090
_cell_measurement_theta_min      4.1360
_cell_volume                     869.57(4)
_computing_cell_refinement
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.46(12)
_diffrn_detector                 'Hybrid Pixel Counting (HPC) detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HyPix-6000HE'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  256
  2  ω    -39.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  256
  3  ω    -34.00  94.00   0.50    0.50    --    5.00  75.00  60.00  256
  4  ω    -29.00  94.00   0.50    0.50    --    5.00  57.00-180.00  246
  5  ω   -145.00 -21.00   0.50    0.50    --  -56.00 -66.00  93.02  248
  6  ω   -149.00 -22.00   0.50    0.50    --  -60.00 -73.00 -61.83  254
  7  ω   -153.00 -25.00   0.50    0.50    --  -64.00 -75.00  18.19  256
  8  ω   -153.00 -26.00   0.50    0.50    --  -64.00 -73.00 -94.20  254
  9  ω   -157.00 -31.00   0.50    0.50    --  -68.00 -72.00-147.00  252
 10  ω   -161.00 -33.00   0.50    0.50    --  -72.00 -74.00  80.13  256
 11  ω   -161.00 -33.00   0.50    0.50    --  -72.00 -74.00 110.00  256
 12  ω   -165.00 -37.00   0.50    0.50    --  -76.00 -75.00 -86.83  256
 13  ω   -165.00 -39.00   0.50    0.50    --  -76.00 -72.00 164.75  252
 14  ω   -165.00 -37.00   0.50    0.50    --  -76.00 -75.00 -86.83  256
 15  ω   -169.00 -42.00   0.50    0.50    --  -80.00 -73.00-117.28  254
 16  ω   -173.00 -48.00   0.50    0.50    --  -84.50 -70.00 -61.45  250
 17  ω   -123.00   4.00   0.50    0.50    --  -84.50  75.00  90.00  254
 18  ω   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00  30.00  254
 19  ω   -123.00   4.00   0.50    0.50    --  -84.50  75.00-150.00  254
 20  ω   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00 120.00  254
 21  ω   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00  90.00  254
 22  ω   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00-150.00  254
 23  ω   -173.00 -51.00   0.50    0.50    --  -84.50 -57.00-150.00  244
 24  ω   -123.00   4.00   0.50    0.50    --  -84.50  75.00 150.00  254
 25  ω   -123.00   4.00   0.50    0.50    --  -84.50  75.00   0.00  254
 26  ω   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00-180.00  254
 27  ω   -123.00   4.00   0.50    0.50    --  -84.50  75.00 -60.00  254
 28  ω   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00   0.00  254
 29  ω   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00  60.00  254
 30  ω    -39.00  89.00   0.50    0.50    --    0.00  38.00-180.00  256
 31  ω    -39.00  89.00   0.50    0.50    --    0.00  38.00 120.00  256
 32  ω   -161.00 -33.00   0.50    0.50    --  -72.00 -75.00-163.62  256
 33  ω   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00 -30.00  254
 34  ω   -123.00   4.00   0.50    0.50    --  -84.50  75.00 -90.00  254
 35  ω   -173.00 -50.00   0.50    0.50    --  -84.50 -48.00 112.78  246
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'profile data from ω-scans and φ-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1055895000
_diffrn_orient_matrix_UB_12      0.1055410000
_diffrn_orient_matrix_UB_13      0.0109926000
_diffrn_orient_matrix_UB_21      0.0994118000
_diffrn_orient_matrix_UB_22      0.0641410000
_diffrn_orient_matrix_UB_23      -0.0791621000
_diffrn_orient_matrix_UB_31      -0.1589285000
_diffrn_orient_matrix_UB_32      -0.0790640000
_diffrn_orient_matrix_UB_33      -0.1268670000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'VariMax VHF'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27579
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        65.646
_diffrn_reflns_theta_max         65.646
_diffrn_reflns_theta_min         4.208
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    3.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0312
_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)+(0.0471P)²+0.1057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2438
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04475c2.cif
_cod_data_source_block           zhushuxiang-zsx-c1-20210405-rt
_cod_database_code               1564792
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O S Cl'
_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   0.882
_shelx_estimated_absorpt_t_min   0.782
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17), C7(H7), C10(H10), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 1.425
_oxdiff_exptl_absorpt_empirical_full_min 0.783
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 0.07494(6) 0.18032(4) 0.50609(5) 0.06526(16) Uani 1 1 d . . . . .
Cl1 Cl 0.83476(7) 0.06442(5) 0.77829(6) 0.08305(19) Uani 1 1 d . . . . .
O1 O 0.55583(17) 0.63678(10) 0.77957(13) 0.0666(3) Uani 1 1 d . . . . .
O2 O 0.34627(18) 0.66025(11) 0.60456(13) 0.0719(4) Uani 1 1 d . . . . .
N2 N 0.00809(18) 0.28545(12) 0.30933(14) 0.0573(4) Uani 1 1 d . . . . .
N1 N 0.25634(19) 0.40822(12) 0.48386(15) 0.0587(4) Uani 1 1 d . . . . .
N3 N -0.0954(2) 0.16556(13) 0.23128(17) 0.0687(4) Uani 1 1 d . . . . .
N4 N -0.1967(2) 0.17526(14) 0.12119(18) 0.0754(4) Uani 1 1 d . . . . .
C12 C 0.2958(2) 0.15578(14) 0.58413(17) 0.0529(4) Uani 1 1 d . . . . .
C13 C 0.4440(2) 0.17584(15) 0.53843(17) 0.0563(4) Uani 1 1 d . . . . .
H13 H 0.4309 0.2072 0.4664 0.068 Uiso 1 1 calc R . . . .
C15 C 0.6268(2) 0.10003(14) 0.70424(18) 0.0584(4) Uani 1 1 d . . . . .
C3 C 0.4218(2) 0.59434(16) 0.66413(18) 0.0564(4) Uani 1 1 d . . . . .
C5 C 0.1319(2) 0.30509(15) 0.43703(17) 0.0555(4) Uani 1 1 d . . . . .
C6 C -0.0319(2) 0.37443(15) 0.24305(17) 0.0562(4) Uani 1 1 d . . . . .
C14 C 0.6099(2) 0.14938(15) 0.59966(18) 0.0585(4) Uani 1 1 d . . . . .
H14 H 0.7100 0.1648 0.5705 0.070 Uiso 1 1 calc R . . . .
C4 C 0.3776(2) 0.45060(14) 0.61827(17) 0.0599(4) Uani 1 1 d . . . . .
H4A H 0.4922 0.4230 0.6269 0.072 Uiso 1 1 calc R . . . .
H4B H 0.3168 0.4140 0.6712 0.072 Uiso 1 1 calc R . . . .
C16 C 0.4800(3) 0.07664(16) 0.74921(18) 0.0637(5) Uani 1 1 d . . . . .
H16 H 0.4923 0.0419 0.8191 0.076 Uiso 1 1 calc R . . . .
C11 C -0.1630(3) 0.30363(16) 0.12359(19) 0.0636(5) Uani 1 1 d . . . . .
C17 C 0.3146(2) 0.10548(15) 0.68907(18) 0.0599(4) Uani 1 1 d . . . . .
H17 H 0.2154 0.0910 0.7192 0.072 Uiso 1 1 calc R . . . .
C7 C 0.0267(3) 0.50712(16) 0.2752(2) 0.0661(5) Uani 1 1 d . . . . .
H7 H 0.1145 0.5552 0.3553 0.079 Uiso 1 1 calc R . . . .
C2 C 0.6160(3) 0.77485(16) 0.8332(2) 0.0747(5) Uani 1 1 d . . . . .
H2A H 0.5082 0.8097 0.8290 0.090 Uiso 1 1 calc R . . . .
H2B H 0.6816 0.8118 0.7829 0.090 Uiso 1 1 calc R . . . .
C10 C -0.2419(3) 0.3606(2) 0.0292(2) 0.0770(5) Uani 1 1 d . . . . .
H10 H -0.3289 0.3128 -0.0513 0.092 Uiso 1 1 calc R . . . .
C8 C -0.0537(3) 0.56151(19) 0.1812(2) 0.0777(6) Uani 1 1 d . . . . .
H8 H -0.0190 0.6496 0.1985 0.093 Uiso 1 1 calc R . . . .
C1 C 0.7396(4) 0.8060(2) 0.9687(2) 0.0955(7) Uani 1 1 d . . . . .
H1A H 0.8469 0.7723 0.9721 0.143 Uiso 1 1 calc GR . . . .
H1B H 0.6739 0.7693 1.0180 0.143 Uiso 1 1 calc GR . . . .
H1C H 0.7791 0.8967 1.0047 0.143 Uiso 1 1 calc GR . . . .
C9 C -0.1858(3) 0.4909(2) 0.0601(2) 0.0816(6) Uani 1 1 d . . . . .
H9 H -0.2363 0.5328 -0.0004 0.098 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 0.0181 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_
_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
C12 S1 C5 102.85(7) . . ?
C3 O1 C2 115.61(14) . . ?
N3 N2 C5 121.93(13) . . ?
C6 N2 N3 109.51(14) . . ?
C6 N2 C5 128.56(13) . . ?
C5 N1 C4 122.68(15) . . ?
N4 N3 N2 108.96(14) . . ?
N3 N4 C11 108.52(15) . . ?
C13 C12 S1 122.75(13) . . ?
C17 C12 S1 117.51(12) . . ?
C17 C12 C13 119.56(16) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.14(16) . . ?
C14 C13 H13 119.9 . . ?
C14 C15 Cl1 119.07(13) . . ?
C14 C15 C16 121.16(17) . . ?
C16 C15 Cl1 119.75(14) . . ?
O1 C3 C4 110.08(15) . . ?
O2 C3 O1 124.95(16) . . ?
O2 C3 C4 124.97(17) . . ?
N2 C5 S1 112.78(11) . . ?
N1 C5 S1 131.37(15) . . ?
N1 C5 N2 115.78(15) . . ?
N2 C6 C11 104.23(14) . . ?
N2 C6 C7 133.90(17) . . ?
C11 C6 C7 121.83(17) . . ?
C13 C14 C15 119.61(15) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
N1 C4 C3 108.98(14) . . ?
N1 C4 H4A 109.9 . . ?
N1 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.14(17) . . ?
C17 C16 H16 120.4 . . ?
C6 C11 N4 108.77(17) . . ?
C6 C11 C10 121.67(17) . . ?
C10 C11 N4 129.54(18) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.35(16) . . ?
C16 C17 H17 119.8 . . ?
C6 C7 H7 122.2 . . ?
C8 C7 C6 115.60(19) . . ?
C8 C7 H7 122.2 . . ?
O1 C2 H2A 109.9 . . ?
O1 C2 H2B 109.9 . . ?
O1 C2 C1 109.04(17) . . ?
H2A C2 H2B 108.3 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C11 C10 H10 121.6 . . ?
C9 C10 C11 116.89(19) . . ?
C9 C10 H10 121.6 . . ?
C7 C8 H8 118.5 . . ?
C7 C8 C9 123.02(19) . . ?
C9 C8 H8 118.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
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 C12 1.7688(17) . ?
S1 C5 1.7777(17) . ?
Cl1 C15 1.7304(17) . ?
O1 C3 1.323(2) . ?
O1 C2 1.459(2) . ?
O2 C3 1.200(2) . ?
N2 N3 1.3817(18) . ?
N2 C5 1.413(2) . ?
N2 C6 1.378(2) . ?
N1 C5 1.260(2) . ?
N1 C4 1.443(2) . ?
N3 N4 1.287(2) . ?
N4 C11 1.397(2) . ?
C12 C13 1.392(2) . ?
C12 C17 1.385(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(2) . ?
C15 C14 1.376(3) . ?
C15 C16 1.381(2) . ?
C3 C4 1.513(2) . ?
C6 C11 1.385(3) . ?
C6 C7 1.399(2) . ?
C14 H14 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.383(2) . ?
C11 C10 1.385(3) . ?
C17 H17 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.366(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.463(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.398(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C9 H9 0.9300 . ?
