Criofolinine and vernavosine, new pentacyclic indole alkaloids incorporating pyrroloazepine and pyridopyrimidine moieties derived from a common yohimbine precursor.
Nge, Choy-Eng; Gan, Chew-Yan; Lim, Kuan-Hon; Ting, Kang-Nee; Low, Yun-Yee; Kam, Toh-Seok; Organic letters 16 (2014) 6330–6333; doi:10.1021/ol503072g

data_1518387
_publ_section_title
;
 Criofolinine and vernavosine, new pentacyclic indole alkaloids
 incorporating pyrroloazepine and pyridopyrimidine moieties derived from a
 common yohimbine precursor.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6330
_journal_page_last               6333
_journal_paper_doi               10.1021/ol503072g
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H22 N2 O6'
_chemical_formula_sum            'C21 H22 N2 O6'
_chemical_formula_weight         398.40
_chemical_name_common            criofolinine
_chemical_temperature_decomposition_gt 463
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7249(5)
_cell_length_b                   12.1181(6)
_cell_length_c                   29.2040(13)
_cell_measurement_reflns_used    3586
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.39
_cell_measurement_theta_min      2.54
_cell_volume                     3795.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ' \w scans'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            33170
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         2.023
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       Block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         7804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1440
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5848
_reflns_number_total             7804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503072g_si_002.cif
_cod_data_source_block           Criofolinine
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified 'more than' ('>') a certain temperature. The value '>463
dec' was changed to '463' - it should be numeric and without a unit
designator.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 1518386--1518387.cif.
;
_cod_database_code               1518387
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014/6
_shelx_res_checksum              29516
_shelx_hkl_checksum              10692