Convenient approach to polyoxygenated dibenzo[c,e]pyrrolo[1,2-a]azepines from donor–acceptor cyclopropanes
Boichenko, Maksim A.; Ivanova, Olga A.; Andreev, Ivan A.; Chagarovskiy, Alexey O.; Levina, Irina I.; Rybakov, Victor B.; Skvortsov, Dmitriy A.; Trushkov, Igor V.; Organic Chemistry Frontiers 5 (2018) 2829–; doi:10.1039/C8QO00742J

data_1554399
_publ_section_title
;
 Convenient approach to polyoxygenated dibenzo[c,e]pyrrolo[1,2-a]azepines
 from donor--acceptor cyclopropanes
;
_journal_issue                   19
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2829
_journal_paper_doi               10.1039/C8QO00742J
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C22 H25 N O6'
_chemical_formula_sum            'C22 H25 N O6'
_chemical_formula_weight         399.43
_chemical_melting_point_gt       ????
_chemical_melting_point_lt       ????
_chemical_name_systematic
7,8,10,11,12-Pentamethoxy-1,2,5,13b-tetrahydrodibenzo[c,e]pyrrolo[1,2-a]azepin-3-one
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1zsm8n
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-05-02 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.801(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7969(3)
_cell_length_b                   8.7827(2)
_cell_length_c                   14.6012(4)
_cell_measurement_reflns_used    20894
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      72.943
_cell_measurement_theta_min      5.768
_cell_volume                     1967.28(8)
_computing_cell_refinement       '<i>X--AREA</i>      (STOE & CIE, 2015)'
_computing_data_collection       '<i>X--AREA</i>      (STOE & CIE, 2015)'
_computing_data_reduction        '<i>X--AREA</i>      (STOE & CIE, 2015)'
_computing_molecular_graphics    '<i>Ortep--3</i>     (Farrugia,   1997)'
_computing_publication_material  '<i>WinGX</i>        (Farrugia,   1999)'
_computing_structure_refinement  '<i>SHELXL--2013</i> (Sheldrick,  2013)'
_computing_structure_solution    '<i>SHELXS97</i>     (Sheldrick,  2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
'65 runs, 1715 frames, detector distance = 42 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20894
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         72.943
_diffrn_reflns_theta_min         5.768
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.9220
_exptl_absorpt_correction_T_min  0.8420
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_preparation       'ethyl acetate : petroleum ether, 1:1'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0604P)^2^+0.2843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3289
_reflns_number_total             3889
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00742j2.cif
_cod_data_source_block           olga1807
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554399
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.855
_exptl_absorpt_factor_mur        0.081
_shelxl_version_number           2013-4
_shelx_res_checksum              20719