Metal-Catalyzed Domino Synthesis of Benzophenanthridines and 6 H-Naphtho[2,3- c]-chromenes.
Chakraborty, Baitan; Jalal, Swapnadeep; Paul, Kartick; Kundal, Sandip; Jana, Umasish; The Journal of organic chemistry 83 (2018) 8139–8149; doi:10.1021/acs.joc.8b00924

data_4035606
_publ_section_title
;
 Metal-Catalyzed Domino Synthesis of Benzophenanthridines and 6
 H-Naphtho[2,3- c]-chromenes.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8139
_journal_page_last               8149
_journal_paper_doi               10.1021/acs.joc.8b00924
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C31 H25 N O2 S'
_chemical_formula_sum            'C31 H25 N O2 S'
_chemical_formula_weight         475.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.624(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5870(10)
_cell_length_b                   9.8447(9)
_cell_length_c                   21.773(2)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      1.8
_cell_volume                     2413.8(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.662
_diffrn_reflns_theta_min         1.838
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0687P)^2^+0.5056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4436
_reflns_number_total             5548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00924_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4035606
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. 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
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C28(H28), C9(H9), C7(H7), C23(H23), C2(H2), C13(H13), C31(H31),
 C24(H24), C30(H30), C6(H6), C3(H3), C27(H27), C29(H29), C10(H10), C26(H26),
 C25(H25)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              56656
_shelx_hkl_checksum              28566
_olex2_submission_special_instructions 'No special instructions were received'