Arboridinine, a Pentacyclic Indole Alkaloid with a New Cage Carbon-Nitrogen Skeleton Derived from a Pericine Precursor.
Wong, Suet-Pick; Gan, Chew-Yan; Lim, Kuan-Hon; Ting, Kang-Nee; Low, Yun-Yee; Kam, Toh-Seok; Organic letters 17 (2015) 3628–3631; doi:10.1021/acs.orglett.5b01757

data_1555112
_publ_section_title
;
 Arboridinine, a Pentacyclic Indole Alkaloid with a New Cage
 Carbon-Nitrogen Skeleton Derived from a Pericine Precursor.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3628
_journal_page_last               3631
_journal_paper_doi               10.1021/acs.orglett.5b01757
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.38
_chemical_melting_point          463.5(5)
_chemical_name_common            Arboridinine
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4987(2)
_cell_length_b                   12.2482(3)
_cell_length_c                   16.8063(3)
_cell_measurement_reflns_used    20464
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.7860
_cell_measurement_theta_min      3.9730
_cell_volume                     1543.58(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'SuperNova, Dual, Atlas'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36099
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         34.956
_diffrn_reflns_theta_min         2.940
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4500
_exptl_crystal_size_mid          0.3800
_exptl_crystal_size_min          0.2500
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         6449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0511P)^2^+0.1952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                6229
_reflns_number_total             6449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01757_si_002.cif
_cod_data_source_block           exp_5771_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '463-464' was changed to
'463.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1555112
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              85114
_shelx_hkl_checksum              82166