A new strategy for the synthesis of diverse benzo[a]carbazoles via a divergent catalytic Michael reaction.
Kripalaya Ratheesh, Arya; Sparkes, Hazel A.; Prasad, Karnam Jayarampillai Rajendra; Organic & biomolecular chemistry 16 (2018) 2527–2540; doi:10.1039/C8OB00154E

data_7156162
_publ_section_title
;
 A new strategy for the synthesis of diverse benzo[a]carbazoles via a
 divergent catalytic Michael reaction.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2527
_journal_page_last               2540
_journal_paper_doi               10.1039/C8OB00154E
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H18 N4 O2'
_chemical_formula_sum            'C24 H18 N4 O2'
_chemical_formula_weight         394.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-05-03 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                72.299(4)
_cell_angle_beta                 87.366(4)
_cell_angle_gamma                72.955(5)
_cell_formula_units_Z            2
_cell_length_a                   8.7409(5)
_cell_length_b                   9.6037(6)
_cell_length_c                   12.1665(7)
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.744
_cell_measurement_theta_min      2.329
_cell_volume                     929.18(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         1.759
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0666 before and 0.0485 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0725 before and 0.0532 after correction.
 The Ratio of minimum to maximum transmission is 0.90.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 24553 reflections, Rint = 0.0713
 (7063 with I > 3sig(I), Rint = 0.0393)
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.189
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0429P)^2^+0.4336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2861
_reflns_number_total             3785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00154e2.cif
_cod_data_source_block           9b
_cod_depositor_comments
'Adding full bibliography for 7156162--7156163.cif.'
_cod_original_cell_volume        929.19(10)
_cod_database_code               7156162
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6697(14) 0.3303(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C3(H3C,H3D), C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              30170
_olex2_submission_special_instructions 'No special instructions were received'