Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement.
Hu, Fangdong; Liu, Huanhuan; Jia, Jiong; Ma, Chen; Organic & biomolecular chemistry 14 (2016) 11076–11079; doi:10.1039/c6ob02098d

data_7155358
_publ_section_title
;
 Transition-metal-free synthesis of indole-fused
 dibenzo[b,f][1,4]oxazepines via Smiles rearrangement.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11076
_journal_page_last               11079
_journal_paper_doi               10.1039/c6ob02098d
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C21 H12 N2 O'
_chemical_formula_sum            'C21 H12 N2 O'
_chemical_formula_weight         296.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-07-22 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.495(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.672(2)
_cell_length_b                   7.6389(14)
_cell_length_c                   36.525(7)
_cell_measurement_reflns_used    3349
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.516
_cell_measurement_theta_min      2.724
_cell_volume                     2974.8(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            14903
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.721
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1185
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+0.6334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3418
_reflns_number_total             5149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02098d2.cif
_cod_data_source_block           p
_cod_depositor_comments
;
         Adding full bibliography for 7155358.cif.

2017-10-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C21 H12 N2 O)'
_cod_original_formula_sum        'C42 H0.25 N4 O2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     592.71
_cod_database_code               7155358
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C21(H21), C31(H31), C30(H30), C29(H29), C28(H28),
  C27(H27), C42(H42), C39(H39), C38(H38), C34(H34), C35(H35), C36(H36), C37(H37)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'