Crystal structure of akuammicine, an indole alkaloid from <i>Catharanthus roseus</i>.
Yahyazadeh, Mahdi; Jerz, Gerold; Selmar, Dirk; Winterhalter, Peter; Jones, Peter G.; Acta crystallographica. Section E, Crystallographic communications 73 (2017) 1658–1661; doi:10.1107/S2056989017014529

data_2311471
_publ_section_title
;
 Crystal structure of akuammicine, an indole alkaloid from <i>Catharanthus
 roseus</i>.
;
_journal_coeditor_code           DX2001
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1658
_journal_page_last               1661
_journal_paper_doi               10.1107/S2056989017014529
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C20 H22 N2 O2'
_chemical_formula_moiety         'C20 H22 N2 O2'
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.39
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                104.696(6)
_cell_angle_beta                 92.637(6)
_cell_angle_gamma                94.548(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4750(7)
_cell_length_b                   7.7067(6)
_cell_length_c                   14.6585(9)
_cell_measurement_reflns_used    13753
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8160
_cell_measurement_theta_min      5.9140
_cell_volume                     812.33(11)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Atlas Nova'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40686
_diffrn_reflns_theta_full        75.000
_diffrn_reflns_theta_max         76.255
_diffrn_reflns_theta_min         5.952
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.200
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2335 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.10(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6159
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.0943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                5741
_reflns_number_total             6159
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            dx2001sup1.cif
_cod_data_source_block           I
_cod_database_code               2311471
_shelx_estimated_absorpt_t_min   0.905
_shelx_estimated_absorpt_t_max   0.980
_shelx_hkl_checksum              56410
_shelx_res_checksum              789