Electrochemically Selective Double C(sp2)-X (X=S/Se, N) Bonds Formation of One Carbon
Guan, Zhipeng; Zhu, Shuxiang; Yang, Yankai; Liu, Yanlong; Wang, Siyuan; Bu, Faxiang; Cong, Hengjiang; Alhumade, Hesham; Zhang, Heng; Lei, Aiwen; Chemical Science  (2021) –; doi:10.1039/D1SC04475C

data_1564792
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -39.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  256
  2  \w    -39.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  256
  3  \w    -34.00  94.00   0.50    0.50    --    5.00  75.00  60.00  256
  4  \w    -29.00  94.00   0.50    0.50    --    5.00  57.00-180.00  246
  5  \w   -145.00 -21.00   0.50    0.50    --  -56.00 -66.00  93.02  248
  6  \w   -149.00 -22.00   0.50    0.50    --  -60.00 -73.00 -61.83  254
  7  \w   -153.00 -25.00   0.50    0.50    --  -64.00 -75.00  18.19  256
  8  \w   -153.00 -26.00   0.50    0.50    --  -64.00 -73.00 -94.20  254
  9  \w   -157.00 -31.00   0.50    0.50    --  -68.00 -72.00-147.00  252
 10  \w   -161.00 -33.00   0.50    0.50    --  -72.00 -74.00  80.13  256
 11  \w   -161.00 -33.00   0.50    0.50    --  -72.00 -74.00 110.00  256
 12  \w   -165.00 -37.00   0.50    0.50    --  -76.00 -75.00 -86.83  256
 13  \w   -165.00 -39.00   0.50    0.50    --  -76.00 -72.00 164.75  252
 14  \w   -165.00 -37.00   0.50    0.50    --  -76.00 -75.00 -86.83  256
 15  \w   -169.00 -42.00   0.50    0.50    --  -80.00 -73.00-117.28  254
 16  \w   -173.00 -48.00   0.50    0.50    --  -84.50 -70.00 -61.45  250
 17  \w   -123.00   4.00   0.50    0.50    --  -84.50  75.00  90.00  254
 18  \w   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00  30.00  254
 19  \w   -123.00   4.00   0.50    0.50    --  -84.50  75.00-150.00  254
 20  \w   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00 120.00  254
 21  \w   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00  90.00  254
 22  \w   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00-150.00  254
 23  \w   -173.00 -51.00   0.50    0.50    --  -84.50 -57.00-150.00  244
 24  \w   -123.00   4.00   0.50    0.50    --  -84.50  75.00 150.00  254
 25  \w   -123.00   4.00   0.50    0.50    --  -84.50  75.00   0.00  254
 26  \w   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00-180.00  254
 27  \w   -123.00   4.00   0.50    0.50    --  -84.50  75.00 -60.00  254
 28  \w   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00   0.00  254
 29  \w   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00  60.00  254
 30  \w    -39.00  89.00   0.50    0.50    --    0.00  38.00-180.00  256
 31  \w    -39.00  89.00   0.50    0.50    --    0.00  38.00 120.00  256
 32  \w   -161.00 -33.00   0.50    0.50    --  -72.00 -75.00-163.62  256
 33  \w   -173.00 -46.00   0.50    0.50    --  -84.50 -75.00 -30.00  254
 34  \w   -123.00   4.00   0.50    0.50    --  -84.50  75.00 -90.00  254
 35  \w   -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 \w-scans and \phi-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/[\s^2^(Fo^2^)+(0.0471P)^2^+0.1057P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              30617
_shelx_hkl_checksum              10018
_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