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_1554398
_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_absolute_configuration unk
_chemical_formula_moiety         'C23 H29 N O7'
_chemical_formula_sum            'C23 H29 N O7'
_chemical_formula_weight         431.47
_chemical_melting_point_gt       408
_chemical_melting_point_lt       409
_chemical_name_systematic
;
1-(3,4,5-trimethoxybenzyl)-5-(3,4,5-trimethoxyphenyl)pyrrolidin-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1q4l4l
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-05-03 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.471(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0556(3)
_cell_length_b                   15.3824(5)
_cell_length_c                   10.7866(5)
_cell_measurement_reflns_used    8566
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      72.794
_cell_measurement_theta_min      5.192
_cell_volume                     1110.38(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 0.993
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
 34 runs, 1132 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     1.54186
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8566
_diffrn_reflns_point_group_measured_fraction_full 0.585
_diffrn_reflns_point_group_measured_fraction_max 0.571
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         72.794
_diffrn_reflns_theta_min         5.192
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  0.9240
_exptl_absorpt_correction_T_min  0.8909
_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    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_preparation       CH~3~OH
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.0239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.164
_reflns_Friedel_fraction_full    0.174
_reflns_Friedel_fraction_max     0.161
_reflns_number_gt                2453
_reflns_number_total             2533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00742j2.cif
_cod_data_source_block           OLGA1703
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               1554398
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.858
_exptl_absorpt_factor_mur        0.079
_shelxl_version_number           2013-4
_shelx_res_checksum              55718