Steviamine, a new class of indolizidine alkaloid [(1<i>R</i>,2<i>S</i>,3<i>R</i>,5<i>R</i>,8a<i>R</i>)-3-hydroxymethyl-5-methyloctahydroindolizine-1,2-diol hydrobromide]
Thompson, Amber L.; Michalik, Agnieszka; Nash, Robert J.; Wilson, Francis X.; van Well, Renate; Johnson, Peter; Fleet, George W. J.; Yu, Chu-Yi; Hu, Xiang-Guo; Cooper, Richard I.; Watkin, David J.; Acta Crystallographica Section E 65 (2009) o2904–o2905; doi:10.1107/S1600536809043827

data_2223902
_publ_section_title
;Steviamine, a new class of indolizidine alkaloid
 [(1<i>R</i>,2<i>S</i>,3<i>R</i>,5<i>R</i>,8a<i>R</i>)-3-hydroxymethyl-5-methyloctahydroindolizine-1,2-diol
 hydrobromide]
;
_journal_coeditor_code           LH2918
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2904
_journal_page_last               o2905
_journal_paper_doi               10.1107/S1600536809043827
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H20 N1 +, Br -'
_chemical_formula_sum            'C10 H20 Br N'
_chemical_formula_weight         282.18
_chemical_name_common            Steviamine
_chemical_name_systematic
;
(1<i>R</i>,2<i>S</i>,3<i>R</i>,5<i>R</i>,8a<i>R</i>)-3-Hydroxymethyl-5-
methyloctahydroindolizine-1,2-diol hydrobromide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.46160(10)
_cell_length_b                   8.87620(10)
_cell_length_c                   15.8270(2)
_cell_measurement_reflns_used    1544
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1188.72(2)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin <i>et al.</i>,  1996)'
_computing_publication_material  'CRYSTALS (Betteridge <i>et al.</i>,  2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge <i>et al.</i>,  2003)'
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>,  1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2675
_diffrn_reflns_theta_full        26.353
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_min         5.101
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.447
_exptl_absorpt_correction_T_max  0.41
_exptl_absorpt_correction_T_min  0.20
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.52
_refine_ls_abs_structure_details 'Flack (1983), 1102 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.002(10)
_refine_ls_extinction_coef       75(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.001023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 0.86P], where P=[max(Fo^2^,0) + 2Fc^2^]/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0522
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0522
_reflns_number_gt                2484
_reflns_number_total             2658
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            lh2918.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_symmetry_cell_setting' value
'Orthorhombic' changed to 'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C10 H20 N1 Br'
_cod_database_code               2223902
_cod_database_fobs_code          2223902