Formation of Cyclohepta[b]indole Scaffolds via Heck Cyclization: A Strategy for Structural Analogues of Ervatamine Group of Indole Alkaloid.
Goswami, Progyashree; Borah, Arun Jyoti; Phukan, Prodeep; The Journal of organic chemistry 80 (2014) 438–; doi:10.1021/jo502443a

data_4030286
_publ_section_title
;
 Formation of Cyclohepta[b]indole Scaffolds via Heck Cyclization: A
 Strategy for Structural Analogues of Ervatamine Group of Indole Alkaloid.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              438
_journal_paper_doi               10.1021/jo502443a
_journal_volume                  80
_journal_year                    2014
_chemical_formula_sum            'C24 H22 Br N O3'
_chemical_formula_weight         452.34
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.9222(14)
_cell_length_b                   10.4851(8)
_cell_length_c                   23.796(2)
_cell_measurement_reflns_used    5169
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.70
_cell_measurement_theta_min      3.21
_cell_volume                     4222.1(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16635
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    1.972
_exptl_absorpt_correction_T_max  0.6181
_exptl_absorpt_correction_T_min  0.5453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.362(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         7022
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1217P)^2^+0.4550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                5373
_reflns_number_total             7022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502443a_si_004.cif
_cod_data_source_block           platon
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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

 Adding full bibliography for 4030286--4030288.cif.
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_cod_original_sg_symbol_H-M      'Pca21 '
_cod_database_code               4030286