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_1518386
_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 ad
_chemical_formula_moiety         'C24 H33 N2 O5.I'
_chemical_formula_sum            'C24 H33 I N2 O5'
_chemical_formula_weight         556.42
_chemical_name_common            vernavosine
_chemical_temperature_decomposition_gt 491
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 102.195(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4239(2)
_cell_length_b                   8.4186(2)
_cell_length_c                   14.8476(3)
_cell_measurement_reflns_used    3200
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.67
_cell_volume                     1273.54(5)
_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-2014/6 (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 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12548
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         28.049
_diffrn_reflns_theta_min         1.403
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.292
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.479
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.180
_refine_ls_abs_structure_details
;
 Flack x determined using 2010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5945
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0475P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                5076
_reflns_number_total             5945
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503072g_si_003.cif
_cod_data_source_block           Vernavosine
_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 '>491
dec' was changed to '491' - 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               1518386
_shelxl_version_number           2014/6
_shelx_res_checksum              83884
_shelx_hkl_checksum              8857