A unified approach to benzo[<i>c</i>]phenanthridines <i>via</i> the cascade dual-annulation/formylation of 2-alkynyl/alkenylbenzonitriles.
Verma, Shalini; Kumar, Manoj; Verma, Akhilesh K.; Chemical communications (Cambridge, England) 59 (2023) 3723–3726; doi:10.1039/d3cc00197k

data_7131354
_publ_section_title
;
 A unified approach to benzo[<i>c</i>]phenanthridines <i>via</i> the
 cascade dual-annulation/formylation of 2-alkynyl/alkenylbenzonitriles.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3723
_journal_page_last               3726
_journal_paper_doi               10.1039/d3cc00197k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C27 H24 N2 O4'
_chemical_formula_sum            'C27 H24 N2 O4'
_chemical_formula_weight         881.01
_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_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-01 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                72.328(6)
_cell_angle_beta                 81.715(5)
_cell_angle_gamma                77.874(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9461(5)
_cell_length_b                   11.7904(8)
_cell_length_c                   12.9458(8)
_cell_measurement_reflns_used    2292
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.7670
_cell_measurement_theta_min      3.7050
_cell_volume                     1125.63(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9328
_diffrn_measured_fraction_theta_max 0.9628
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -39.00  12.00   1.00    2.50    --  -14.36 -77.00  90.00   51
  2  \w    -75.00   1.00   1.00    2.50    --  -14.36 -38.00 -60.00   76
  3  \w     -5.00  37.00   1.00    2.50    --  -14.36  77.00 -60.00   42
  4  \w    -72.00   7.00   1.00    2.50    --  -14.36 -19.00   0.00   79
  5  \w      1.00  30.00   1.00    2.50    --   18.43  77.00 -30.00   29
  6  \w     11.00  88.00   1.00    2.50    --   18.43  38.00-150.00   77
  7  \w     28.00  80.00   1.00    2.50    --   18.43-138.00 -14.00   52
  8  \w      5.00  78.00   1.00    2.50    --   18.43  57.00 -90.00   73
  9  \w    -13.00  57.00   1.00    2.50    --   18.43 -99.00-150.00   70
 10  \w    -20.00  56.00   1.00    2.50    --   18.43 -99.00  60.00   76
 11  \w    -46.00  23.00   1.00    2.50    --   18.43 -38.00  90.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0164233000
_diffrn_orient_matrix_UB_12      0.0320225000
_diffrn_orient_matrix_UB_13      -0.0553887000
_diffrn_orient_matrix_UB_21      -0.0185343000
_diffrn_orient_matrix_UB_22      -0.0481158000
_diffrn_orient_matrix_UB_23      -0.0161388000
_diffrn_orient_matrix_UB_31      -0.0882334000
_diffrn_orient_matrix_UB_32      0.0278197000
_diffrn_orient_matrix_UB_33      -0.0017500000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.1283
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17117
_diffrn_reflns_theta_full        29.6545
_diffrn_reflns_theta_max         29.65
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.2996
_exptl_crystal_description       white
_exptl_crystal_F_000             464.2341
_refine_diff_density_max         0.5551
_refine_diff_density_min         -0.5501
_refine_diff_density_rms         0.1273
_refine_ls_d_res_high            0.7182
_refine_ls_d_res_low             6.1604
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0276
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0276
_refine_ls_R_factor_all          0.1762
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0584P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1904
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              16
_reflns_limit_k_min              -15
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2361
_reflns_number_total             5488
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc00197k2.cif
_cod_data_source_block           SV-949B
_cod_depositor_comments
;
         Adding full bibliography for 7131354.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18 H16 N1.333 O2.667'
_cod_original_formula_weight         293.67
_cod_original_formula_moiety         '0.67(C27 H24 N2 O4)'
_cod_original_formula_units_Z            3
_cod_database_code               7131354
_chemical_oxdiff_formula         'C16 H19 N2 O4'
_chemical_oxdiff_usercomment     08-010-2019
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00a,H00b)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00U(H00U), C00T(H00T), C00L(H00L), C00G(H00G), C00O(H00O),
 C00S(H00S), C00M(H00M), C00P(H00P), C00H(H00H), C00J(H00J), N002(H002)
2.d Idealised Me refined as rotating group:
 C00W(H00k,H00n,H00q), C00V(H00c,H00e,H00f), C00X(H00r,H00v,H00w)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.074
_oxdiff_exptl_absorpt_empirical_full_min 0.917