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_7156163
_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         'C23 H16 N4 O2'
_chemical_formula_sum            'C23 H16 N4 O2'
_chemical_formula_weight         380.40
_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             2016-09-15
_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                97.848(6)
_cell_angle_beta                 104.222(6)
_cell_angle_gamma                108.609(6)
_cell_formula_units_Z            2
_cell_length_a                   8.3973(8)
_cell_length_b                   8.5161(9)
_cell_length_c                   14.1035(13)
_cell_measurement_reflns_used    3477
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.60
_cell_volume                     900.83(16)
_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 0.989
_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_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16596
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.102
_diffrn_reflns_theta_min         1.532
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1413 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.7480.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     275
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0617P)^2^+0.2521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3070
_reflns_number_total             4340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00154e2.cif
_cod_data_source_block           9d
_cod_depositor_comments
'Adding full bibliography for 7156162--7156163.cif.'
_cod_database_code               7156163
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 C3-C2 \\sim C3A-C2A \\sim C6-C1A \\sim C6-C1
 with sigma of 0.01
 C2A-C1A \\sim C2-C1
 with sigma of 0.01
 C5-C4 \\sim C5-C4A \\sim C4A-C3A \\sim C4-C3 \\sim C3-C2 \\sim C3A-C2A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C4A \\sim C3A \\sim C1A \\sim C2A \\sim
C22A \\sim C22 \\sim C23A \\sim C23 \\sim N4A \\sim N4 \\sim C21A \\sim C21
\\sim N3A \\sim N3: within 2A with sigma of 0.003 and sigma for terminal atoms
of 0.006
4. Others
 Fixed Sof: N3(0.68973) H3A(0.68973) H3B(0.68973) N4(0.68973) C1(0.68973)
 C2(0.68973) C3(0.68973) H3C(0.68973) H3D(0.68973) C4(0.68973) H4A(0.68973)
 H4B(0.68973) C21(0.68973) C22(0.68973) C23(0.68973) C4A(0.31027) H4AA(0.31027)
 H4AB(0.31027) C3A(0.31027) H3AA(0.31027) H3AB(0.31027) C22A(0.31027)
 C21A(0.31027) N3A(0.31027) H3AC(0.31027) H3AD(0.31027) C23A(0.31027)
 N4A(0.31027) C1A(0.31027) C2A(0.31027)
5.a Rotating group:
 N3(H3A,H3B), N3A(H3AC,H3AD)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3C,H3D), C4(H4A,H4B), C4A(H4AA,H4AB), C3A(H3AA,H3AB)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_shelx_res_checksum              18253
_olex2_submission_special_instructions 'No special instructions were received'