The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
Li, Jun-Jie; Dong, Fang-Yun; Zou, Qi-Wen; Feng, Yin; Yang, Yu-Tao; Su, Kai-Xuan; Huang, Yong-Fu; Jiang, Xu-Hong; Cheng, Xing-An; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 1047–1049; doi:10.1515/ncrs-2021-0197

data_8104662
_publ_section_title
;
 The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine,
 C19H25N5O
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1047
_journal_page_last               1049
_journal_paper_doi               10.1515/ncrs-2021-0197
_journal_volume                  236
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H25 N5 O'
_chemical_formula_sum            'C19 H25 N5 O'
_chemical_formula_weight         339.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 94.2600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0600(2)
_cell_length_b                   5.39920(10)
_cell_length_c                   19.8514(2)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2520
_cell_measurement_theta_min      3.6830
_cell_volume                     1716.58(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9892
_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     -8.00  29.00   0.50    1.00    --    0.00 -82.00 -30.00   74
  2  \w    -42.00  -2.00   0.50    1.00    --    0.00 -77.00 -90.00   80
  3  \w    -11.00  46.00   0.50    1.00    --    0.00  38.00-180.00  114
  4  \w    -26.00  31.00   0.50    1.00    --    0.00 -82.00  30.00  114
  5  \w     52.00  81.00   0.50    1.00    --    0.00  38.00-180.00   58
  6  \w    -33.00  17.00   0.50    1.00    --    0.00 -82.00 120.00  100
  7  \w     70.00  97.00   0.50    5.80    --   95.80  68.00-121.72   54
  8  \w    116.00 185.00   0.50    5.80    --   95.80  72.00-142.09  138
  9  \w     73.00 109.00   0.50    5.80    --   95.80  56.00-114.69   72
 10  \w     72.00  98.00   0.50    5.80    --   95.80  62.00-157.49   52
 11  \w     85.00 134.00   0.50    5.80    --   95.80  15.00   0.00   98
 12  \w    141.00 185.00   0.50    5.80    --   95.80  15.00   0.00   88
 13  \w     11.00 118.00   0.50    5.80    --   95.80 -61.00-150.00  214
 14  \w     72.00  98.00   0.50    5.80    --   95.80  61.00 150.00   52
 15  \w     68.00  95.00   0.50    5.80    --   95.80  72.00-110.97   54
 16  \w     68.00  94.00   0.50    5.80    --   95.80  72.00-142.09   52
 17  \w     77.00 117.00   0.50    5.80    --   95.80  45.00 150.00   80
 18  \w    151.00 178.00   0.50    5.80    --   95.80  30.00-120.00   54
 19  \w    144.00 181.00   0.50    5.80    --   95.80  45.00 150.00   74
 20  \w    116.00 185.00   0.50    5.80    --   95.80  72.00-161.43  138
 21  \w     78.00 105.00   0.50    5.80    --   95.80  45.00-180.00   54
 22  \w    128.00 185.00   0.50    5.80    --   95.80  45.00-180.00  114
 23  \w      7.00  67.00   0.50    5.80    --   95.80 -77.00 -30.00  120
 24  \w     91.00 116.00   0.50    5.80    --   95.80 -77.00 -30.00   50
 25  \w     33.00 121.00   0.50    5.80    --   95.80 -77.00-150.00  176
 26  \w    137.00 182.00   0.50    5.80    --   95.80  82.00-120.00   90
 27  \w     73.00  98.00   0.50    5.80    --   95.80  61.00-180.00   50
 28  \w     76.00 102.00   0.50    5.80    --   95.80  45.00-120.00   52
 29  \w     72.00  99.00   0.50    5.80    --   95.80  61.00-150.00   54
 30  \w     74.00 109.00   0.50    5.80    --   95.80  61.00 -90.00   70
 31  \w     68.00  94.00   0.50    5.80    --   95.80  72.00-161.43   52
 32  \w    160.00 185.00   0.50    5.80    --   95.80  56.00-114.69   50
 33  \w     80.00 113.00   0.50    5.80    --   95.80  30.00-150.00   66
 34  \w     80.00 105.00   0.50    5.80    --   95.80  30.00-120.00   50
 35  \w     77.00 104.00   0.50    5.80    --   95.80  41.00-157.58   54
 36  \w     98.00 125.00   0.50    5.80    --   95.80  45.00 -90.00   54
 37  \w     73.00 100.00   0.50    5.80    --   95.80  57.00-164.96   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0903471000
_diffrn_orient_matrix_UB_12      0.0894385000
_diffrn_orient_matrix_UB_13      -0.0162691000
_diffrn_orient_matrix_UB_21      0.0205373000
_diffrn_orient_matrix_UB_22      0.0616970000
_diffrn_orient_matrix_UB_23      -0.0726987000
_diffrn_orient_matrix_UB_31      -0.0258223000
_diffrn_orient_matrix_UB_32      -0.2638539000
_diffrn_orient_matrix_UB_33      -0.0225093000
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19482
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.403
_diffrn_reflns_theta_min         2.759
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6659
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0451P)^2^+0.2308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                6104
_reflns_number_total             6659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0197_suppl.cif
_cod_data_source_block           4cnpyr_collect
_cod_database_code               8104662
_chemical_oxdiff_formula         'C82 H106 N14 O4 '
_diffrn_oxdiff_ac3_digest_frames
;
018729cac7ace14aca237cc416a51bfd15000280987
;
_diffrn_oxdiff_ac3_digest_hkl
;
0170b4c05bb500ec8d2be2c321a223dd915ef9
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C12A(H), C12(H12), C10A(HA), C10(H10), C6A(HD), C4(H4), C6(H6), C4A(HI),
 C5(H5), C5A(HR)
1.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B), C3A(HB,HC), C7(H7A,H7B), C13A(HE,HF), C7A(HJ,
 HK), C15A(HL,HM), C11A(HN,HO), C1(H1A,H1B), C2(H2A,H2B), C1A(HP,HQ), C9(H9A,
 H9B), C8(H8A,H8B), C9A(HS,HT), C15(H15A,H15B), C2A(HU,HV), C8A(HW,HX), C3(H3A,
 H3B)
1.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C16A(HG), C18A(HH)
;
_shelx_res_checksum              14617
_shelx_hkl_checksum              4733
_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 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.604