Construction of Benzo[a]carbazole Derivatives via Diels-Alder Reaction of Arynes with Vinylindoles
Wu, Lijun; Huang, Hui; Dang, Pan; Liang, Yun; Pi, Shaofeng; RSC Adv.  (2015) –; doi:10.1039/C5RA11025D

data_7221610
_publ_section_title
;
 Construction of Benzo[a]carbazole Derivatives via Diels-Alder Reaction of
 Arynes with Vinylindoles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA11025D
_journal_year                    2015
_chemical_formula_moiety         'C23 H16 N2 O2'
_chemical_formula_sum            'C23 H16 N2 O2'
_chemical_formula_weight         352.38
_chemical_name_systematic        11-benzyl-5-nitro-11H-benzo[a]carbazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-04-13 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.323(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7929(3)
_cell_length_b                   14.5941(5)
_cell_length_c                   10.6740(5)
_cell_measurement_reflns_used    3363
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      73.1770
_cell_measurement_theta_min      4.3030
_cell_volume                     870.32(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.9789
_diffrn_measurement_details
;
  1 omega -118.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -77.0000    0.0000 100

  2 omega  -65.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  178.0000 -150.0000 25

  3 omega  -30.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056   38.0000  120.0000 64

  4 omega  -32.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6056  -57.0000 -150.0000 102

  5 omega    4.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6056  -99.0000  120.0000 76

  6 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000  -60.0000 101

  7 omega   37.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  -90.0000 53

  8 omega   38.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -45.0000   30.0000 26

  9 omega   71.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775 -125.0000  120.0000 51

 10 omega   30.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000 -120.0000 74

 11 omega   33.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775 -125.0000  120.0000 25

 12 omega   50.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -77.0000  -60.0000 90

 13 omega   33.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -45.0000   60.0000 51

 14 omega   78.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000   60.0000 76

 15 omega   54.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  120.0000 36

 16 omega   39.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -45.0000 -120.0000 37

 17 omega   94.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000  -60.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0456715000
_diffrn_orient_matrix_UB_12      -0.0033202000
_diffrn_orient_matrix_UB_13      -0.1356650000
_diffrn_orient_matrix_UB_21      -0.1753493000
_diffrn_orient_matrix_UB_22      -0.0810383000
_diffrn_orient_matrix_UB_23      -0.0370648000
_diffrn_orient_matrix_UB_31      -0.2080063000
_diffrn_orient_matrix_UB_32      0.0675312000
_diffrn_orient_matrix_UB_33      -0.0511110000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4998
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.558
_diffrn_reflns_theta_min         4.295
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2662
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0846
_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^)+(0.1298P)^2^+1.9272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2608
_refine_ls_wR_factor_ref         0.2617
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.713
_reflns_Friedel_fraction_max     0.728
_reflns_number_gt                2609
_reflns_number_total             2662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra11025d2.cif
_cod_data_source_block           exp_5009
_cod_database_code               7221610
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C20 H17 N'
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'