1-(1-Hydroxyethyl)-7,8-dihydroindolo[2,3-<i>a</i>]pyridine[3,4-<i>g</i>]quinolizin-5(13<i>H</i>)-one (angustoline) monohydrate from <i>Nauclea subdita</i> (Rubiaceae)
Liew, Sook Yee; Mukhtar, Mat Ropi; Awang, Khalijah; Mustafa, Mohd Rais; Ng, Seik Weng; Acta Crystallographica Section E 67 (2011) o1727–o1728; doi:10.1107/S1600536811022768

data_2230935
_publ_section_title
;
 1-(1-Hydroxyethyl)-7,8-dihydroindolo[2,3-<i>a</i>]pyridine[3,4-<i>g</i>]quinolizin-5(13<i>H</i>)-one
 (angustoline) monohydrate from <i>Nauclea subdita</i> (Rubiaceae)
;
_journal_coeditor_code           XU5242
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1727
_journal_page_last               o1728
_journal_paper_doi               10.1107/S1600536811022768
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C20 H17 N3 O2, H2 O'
_chemical_formula_sum            'C20 H19 N3 O3'
_chemical_formula_weight         349.38
_chemical_name_common            'angustoline monohydrate'
_chemical_name_systematic
;
1-(1-Hydroxyethyl)-7,8-dihydroindolo[2,3-<i>a</i>]pyridine[3,4-
<i>g</i>]quinolizin-5(13<i>H</i>)-one monohydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.117(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8350(3)
_cell_length_b                   6.7002(2)
_cell_length_c                   14.7347(4)
_cell_measurement_reflns_used    3352
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0299
_cell_measurement_theta_min      3.0770
_cell_volume                     849.48(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Agilent SuperNova Dual with an Atlas detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6453
_diffrn_reflns_theta_full        74.20
_diffrn_reflns_theta_max         74.20
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.8034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.225
_refine_ls_abs_structure_details 'Flack (1983), 1395 Friedel pairs'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.0395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                3015
_reflns_number_total             3252
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            xu5242.cif
_cod_data_source_block           I
_cod_original_cell_volume        849.48(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2230935
_cod_database_fobs_code          2230935