The crystal structure of N′,N″,2-tris((E)-5-chloro-2-hydroxybenzylidene)hydrazine-1-carbohydrazonhydrazide hydrochloride – methanol (1/3), C25H30Cl4N6O6
Zhan, An; Liu, E.; Jian, Fangfang; Liang, Tongling; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 903–905; doi:10.1515/ncrs-2022-0308

data_8107247
_publ_section_title
;
 The crystal structure of
 N&#x2032;,N&#x2033;,2-tris((E)-5-chloro-2-hydroxybenzylidene)hydrazine-1-carbohydrazonhydrazide
 hydrochloride -- methanol (1/3), C25H30Cl4N6O6
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              903
_journal_page_last               905
_journal_paper_doi               10.1515/ncrs-2022-0308
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C22 H18 Cl3 N6 O3, Cl, 3(C H4 O)'
_chemical_formula_sum            'C25 H30 Cl4 N6 O6'
_chemical_formula_weight         652.35
_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
_cell_angle_alpha                106.929(2)
_cell_angle_beta                 99.753(2)
_cell_angle_gamma                98.675(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2652(2)
_cell_length_b                   11.7642(3)
_cell_length_c                   14.6692(4)
_cell_measurement_reflns_used    14961
_cell_measurement_temperature    170.01(11)
_cell_measurement_theta_max      76.9750
_cell_measurement_theta_min      3.1940
_cell_volume                     1473.15(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_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     26.00 110.00   0.50    0.08    --   47.70  74.00 -10.00  168
  2  \w     89.00 178.00   0.50    0.10    --  107.36  74.00 -10.00  178
  3  \w     94.00 175.00   0.50    0.10    --  107.36  57.00 -60.00  162
  4  \w     94.00 177.00   0.50    0.10    --  107.36  38.00 -90.00  166
  5  \w     24.00  78.00   0.50    0.08    --   47.70-125.00  90.00  108
  6  \w     24.00  62.00   0.50    0.08    --   47.70-125.00 -90.00   76
  7  \w     69.00  94.00   0.50    0.08    --   47.70-125.00 -90.00   50
  8  \w     39.00  67.00   0.50    0.08    --   47.70 -74.00-138.00   56
  9  \w    -19.00  25.00   0.50    0.08    --   47.70 -74.00-138.00   88
 10  \w    -16.00  42.00   0.50    0.08    --   47.70 -38.00-120.00  116
 11  \w     79.00 111.00   0.50    0.10    --  107.36-125.00 -30.00   64
 12  \w     36.00  90.00   0.50    0.10    --  107.36 -99.00  60.00  108
 13  \w     45.00  75.00   0.50    0.10    --  107.36-125.00 -30.00   60
 14  \w     35.00 106.00   0.50    0.10    --  107.36 -99.00 150.00  142
 15  \w     69.00 106.00   0.50    0.10    --  107.36 -99.00 -30.00   74
 16  \w     49.00 105.00   0.50    0.10    --  107.36 -99.00-120.00  112
 17  \w     36.00  70.00   0.50    0.10    --  107.36 -99.00-150.00   68
 18  \w     81.00 106.00   0.50    0.10    --  107.36 -99.00-180.00   50
 19  \w     56.00  82.00   0.50    0.10    --  107.36 -74.00-138.00   52
 20  \w     36.00  69.00   0.50    0.10    --  107.36 -57.00 -60.00   66
 21  \w     38.00  68.00   0.50    0.10    --  107.36 -57.00 150.00   60
 22  \w   -120.00 -88.00   0.50    0.08    --  -47.70-125.00 -30.00   64
 23  \w   -118.00 -27.00   0.50    0.08    --  -47.70 -74.00-138.00  182
 24  \w   -145.00 -91.00   0.50    0.10    -- -104.50 -74.00-138.00  108
 25  \w   -166.00-122.00   0.50    0.10    -- -104.50-125.00 -60.00   88
 26  \w   -105.00 -79.00   0.50    0.10    -- -104.50-125.00 -60.00   52
 27  \w   -174.00 -98.00   0.50    0.10    -- -104.50 -38.00  90.00  152
 28  \w   -171.00-142.00   0.50    0.10    -- -104.50 -19.00   0.00   58
 29  \w   -138.00 -96.00   0.50    0.10    -- -104.50 -19.00   0.00   84
 30  \w    -66.00 -37.00   0.50    0.10    -- -104.50  77.00  60.00   58
 31  \w   -102.00 -71.00   0.50    0.10    -- -104.50  77.00  60.00   62
 32  \w    -92.00 -32.00   0.50    0.10    -- -104.50  74.00 -10.00  120
 33  \w    -80.00 -54.00   0.50    0.10    -- -104.50  77.00 -60.00   52
 34  \w    -62.00 -34.00   0.50    0.10    -- -104.50  57.00-150.00   56
 35  \w    -62.00 -32.00   0.50    0.10    -- -104.50  57.00-180.00   60
 36  \w    -34.00  -8.00   0.50    0.08    --  -47.70  74.00 -10.00   52
 37  \w    -60.00 -35.00   0.50    0.10    -- -104.50  57.00  90.00   50
 38  \w    -62.00 -37.00   0.50    0.10    -- -104.50  57.00 120.00   50
 39  \w    -59.00 -33.00   0.50    0.10    -- -104.50  57.00 150.00   52
 40  \w   -129.00 -66.00   0.50    0.10    -- -104.50 149.00  42.32  126
 41  \w   -110.00 -84.00   0.50    0.10    -- -104.50 125.00   0.00   52
 42  \w    -57.00 -32.00   0.50    0.10    -- -104.50 125.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1703675000
_diffrn_orient_matrix_UB_12      -0.0504120000
_diffrn_orient_matrix_UB_13      -0.0247039000
_diffrn_orient_matrix_UB_21      0.0177337000
_diffrn_orient_matrix_UB_22      -0.0454027000
_diffrn_orient_matrix_UB_23      0.0889201000
_diffrn_orient_matrix_UB_31      -0.0216183000
_diffrn_orient_matrix_UB_32      0.1225522000
_diffrn_orient_matrix_UB_33      0.0646523000
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18336
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.347
_diffrn_reflns_theta_min         3.232
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light pink'
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5986
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0468P)^2^+0.4012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5692
_reflns_number_total             5986
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0308_suppl.cif
_cod_data_source_block           tx10365_auto
_cod_database_code               8107247
_chemical_oxdiff_formula         CHNOClFMn
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O6 \\sim C25 \\sim O6A \\sim C25A: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 1.7A
3. Others
 Sof(O6A)=Sof(H6AA)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(O6)=Sof(H6A)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), N3(H3A), N5(H5), C2(H2A), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11),
 C13(H13), C14(H14), C16(H16), C18(H18), C20(H20), C21(H21)
4.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C25A(H25D,H25E,
 H25F)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4A), O5(H5A), O6(H6A), O6A(H6AA)
;
_shelx_res_checksum              64094
_shelx_hkl_checksum              27617
_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.778