The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine, C18H26ClN4O
Jing-Min, Ye; Hui-Qing, He; Xu-Hong, Jiang; Zhan-Mei, Liu; Xing-An, Cheng; Zhao-Chang, He; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 785–786; doi:10.1515/ncrs-2019-0105

data_8105850
_publ_section_title
;
 The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine,
 C18H26ClN4O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              785
_journal_page_last               786
_journal_paper_doi               10.1515/ncrs-2019-0105
_journal_volume                  234
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H26 Cl N4 O'
_chemical_formula_sum            'C18 H26 Cl N4 O'
_chemical_formula_weight         349.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.34760(10)
_cell_length_b                   14.4068(2)
_cell_length_c                   22.3285(4)
_cell_measurement_reflns_used    5817
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4050
_cell_measurement_theta_min      3.9850
_cell_volume                     1720.23(5)
_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 (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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    -13.00  31.00   0.50    1.81    --    0.00 -82.00-120.00   88
  2  \w    -26.00  31.00   0.50    1.81    --    0.00 -82.00 -30.00  114
  3  \w    -25.00   0.00   0.50    1.81    --    0.00 -82.00-180.00   50
  4  \w     24.00  88.00   0.50    7.23    --   94.60 -30.00 -60.00  128
  5  \w     16.00 112.00   0.50    7.23    --   94.60 -45.00-120.00  192
  6  \w     13.00  44.00   0.50    7.23    --   94.60 -77.00  60.00   62
  7  \w      5.00 118.00   0.50    7.23    --   94.60 -61.00  30.00  226
  8  \w     85.00 122.00   0.50    7.23    --   94.60 -77.00  60.00   74
  9  \w     93.00 177.00   0.50    7.23    --   94.60  30.00 -30.00  168
 10  \w      8.00 100.00   0.50    7.23    --   94.60 -82.00  30.00  184
;
_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      0.1495921000
_diffrn_orient_matrix_UB_12      -0.0913326000
_diffrn_orient_matrix_UB_13      -0.0005996000
_diffrn_orient_matrix_UB_21      -0.2440032000
_diffrn_orient_matrix_UB_22      -0.0549812000
_diffrn_orient_matrix_UB_23      -0.0092820000
_diffrn_orient_matrix_UB_31      0.0317690000
_diffrn_orient_matrix_UB_32      0.0083389000
_diffrn_orient_matrix_UB_33      -0.0683973000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8559
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.857
_diffrn_reflns_theta_min         3.651
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81975
_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            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0372
_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^)+(0.0540P)^2^+0.3800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                3196
_reflns_number_total             3374
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0105_suppl.cif
_cod_data_source_block           a
_cod_database_code               8105850
_chemical_oxdiff_formula         'C88 H108 Cl4 O4 '
_reflns_odcompleteness_completeness 99.78
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6), C11(H11), C7(H7), C13(H13), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C18(H18A,H18B), C12(H12A,H12B), C8(H8A,H8B), C10(H10A,H10B),
 C9(H9A,H9B), C3(H3A,H3B), C2(H2A,H2B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N24(H24), C20(H20), C23(H23)
;
_shelx_res_checksum              80287
_shelx_hkl_checksum              94522
_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 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.626