Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C22H31N5O4S2
Li, Xin-Hong; Qin, Zhao-Xian; Cao, Sheng-Li; Zeitschrift für Kristallographie - New Crystal Structures 233 (2018) 133–135; doi:10.1515/ncrs-2017-0219

data_8106074
_publ_section_title
;
 Crystal structure of tert-butyl
 (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate,
 C22H31N5O4S2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              133
_journal_page_last               135
_journal_paper_doi               10.1515/ncrs-2017-0219
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C22 H31 N5 O4 S2'
_chemical_formula_sum            'C22 H31 N5 O4 S2'
_chemical_formula_weight         493.64
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                72.7900(10)
_cell_angle_beta                 82.3010(10)
_cell_angle_gamma                71.0800(10)
_cell_formula_units_Z            2
_cell_length_a                   9.03660(10)
_cell_length_b                   10.3253(2)
_cell_length_c                   14.9997(2)
_cell_measurement_reflns_used    8180
_cell_measurement_temperature    271.2(2)
_cell_measurement_theta_max      73.2590
_cell_measurement_theta_min      5.1730
_cell_volume                     1263.54(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      271.2(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.986
_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    -89.00  34.00   0.50    0.50    --    0.00 -57.00  60.00  246
  2  \w    -89.00  34.00   0.50    0.50    --    0.00 -57.00-180.00  246
  3  \w    -34.00  89.00   0.50    0.50    --    0.00  57.00   0.00  246
  4  \w    -89.00  36.00   0.50    0.50    --    0.00 -72.00   0.00  250
  5  \w      7.00 133.00   0.50    0.78    --   96.60 -72.00  30.00  252
  6  \w      7.00 186.00   0.50    0.78    --   96.60 -15.00  90.00  358
  7  \w     10.00 126.00   0.50    0.78    --   96.60 -45.00 -60.00  232
  8  \w      8.00  79.00   0.50    0.78    --   96.60 -61.00 120.00  142
  9  \w      7.00 128.00   0.50    0.78    --   96.60 -72.00-180.00  242
 10  \w     80.00 132.00   0.50    0.78    --   96.60 -72.00 -60.00  104
 11  \w     93.00 121.00   0.50    0.78    --   96.60 -45.00  60.00   56
 12  \w     62.00  88.00   0.50    0.78    --   96.60  61.00 120.00   52
 13  \w    106.00 174.00   0.50    0.78    --   96.60  61.00 120.00  136
 14  \w     28.00 114.00   0.50    0.78    --   96.60 -72.00 -90.00  172
 15  \w      7.00  32.00   0.50    0.78    --   96.60 -45.00  60.00   50
 16  \w     75.00 120.00   0.50    0.78    --   96.60 -72.00-150.00   90
 17  \w     24.00  50.00   0.50    0.78    --   96.60 -72.00  90.00   52
 18  \w     79.00 125.00   0.50    0.78    --   96.60 -72.00  90.00   92
 19  \w     26.00 142.00   0.50    0.78    --   96.60 -30.00 150.00  232
 20  \w     93.00 127.00   0.50    0.78    --   96.60 -72.00 120.00   68
 21  \w     10.00  37.00   0.50    0.78    --   96.60 -72.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0535933000
_diffrn_orient_matrix_UB_12      -0.0207254000
_diffrn_orient_matrix_UB_13      0.0978817000
_diffrn_orient_matrix_UB_21      -0.0183572000
_diffrn_orient_matrix_UB_22      0.1599859000
_diffrn_orient_matrix_UB_23      -0.0236792000
_diffrn_orient_matrix_UB_31      -0.1712506000
_diffrn_orient_matrix_UB_32      0.0282288000
_diffrn_orient_matrix_UB_33      0.0379413000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13898
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.701
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.3918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3901
_reflns_number_total             4400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2017-0219_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106074
_chemical_oxdiff_formula         'C12 H10 N2 S2'
_reflns_odcompleteness_completeness 98.52
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B)
2.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5A), C7(H7A), C8(H8A)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.807
_oxdiff_exptl_absorpt_empirical_full_min 0.765