Nigellidine-4-O-sulfite, the first sulfated indazole-type alkaloid from the seeds of Nigella sativa
Ali, Zulfiqar; Ferreira, Daneel; Carvalho, Paulo; Avery, Mitchell A.; Khan, Ikhlas A.; Journal of natural products 71 (2008) 1111–1112; doi:10.1021/np800172x

data_1504460
_publ_section_title
;
 Nigellidine-4-O-sulfite, the first sulfated indazole-type alkaloid from
 the seeds of Nigella sativa
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1111
_journal_page_last               1112
_journal_paper_doi               10.1021/np800172x
_journal_volume                  71
_journal_year                    2008
_chemical_compound_source        'Extracted from Nigella sativa Linn.'
_chemical_formula_moiety         'C18 H18 N2 O5 S'
_chemical_formula_sum            'C18 H18 N2 O5 S'
_chemical_formula_weight         374.40
_chemical_name_common            'Nigellidine sulphate'
_chemical_name_systematic
;
11-(4-hydroxyphenyl)-3-methyl-6,7,8,9-tetrahydropyridazino
[1,2-a]indazol-10-ium-1-yl sulfate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2008-02-13 # Formatted by publCIF
;
_cell_angle_alpha                73.781(2)
_cell_angle_beta                 68.704(3)
_cell_angle_gamma                72.799(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6602(4)
_cell_length_b                   10.0129(4)
_cell_length_c                   10.7964(4)
_cell_measurement_reflns_used    6032
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.95
_cell_measurement_theta_min      4.48
_cell_volume                     817.57(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7785
_diffrn_reflns_theta_full        69.37
_diffrn_reflns_theta_max         69.37
_diffrn_reflns_theta_min         4.71
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFF Cu 2 K90'
_exptl_absorpt_coefficient_mu    2.071
_exptl_absorpt_correction_T_max  0.8197
_exptl_absorpt_correction_T_min  0.6048
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blades
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method
;
'The title compound was dissolved in Chloroform, Methanol and Water (65:35:10),
and crystals formed after more Methanol was added'
;
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.5065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                2632
_reflns_number_total             2792
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np800172x-file003.cif
_cod_data_source_block           zns7_92_1a
_cod_database_code               1504460