Harnessing the benzyne insertion consequence to enable π-extended pyrido-acridine and quinazolino-phenanthridine.
Ghosh, Swarnali; Das, Dwaipayan; Mandal, Rahul Dev; Das, Asish R.; Organic & biomolecular chemistry 22 (2024) 5591–5602; doi:10.1039/d4ob00533c

data_7159967
_publ_section_title
;
 Harnessing the benzyne insertion consequence to enable &#x3c0;-extended
 pyrido-acridine and quinazolino-phenanthridine.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5591
_journal_page_last               5602
_journal_paper_doi               10.1039/d4ob00533c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H14 Cl2 N4'
_chemical_formula_sum            'C20 H14 Cl2 N4'
_chemical_formula_weight         381.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-12-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-12-18 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.50(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.70(4)
_cell_length_b                   6.71(2)
_cell_length_c                   22.55(4)
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      66.47
_cell_measurement_theta_min      3.91
_cell_volume                     4036(15)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      295.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1397
_diffrn_reflns_av_unetI/netI     0.1197
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            55384
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.967
_diffrn_reflns_theta_min         6.805
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.969
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.3258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1662 before and 0.1095 after correction.
The Ratio of minimum to maximum transmission is 0.5577.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.0068(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1630
_refine_ls_R_factor_gt           0.0978
_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^)+(0.1858P)^2^+2.3718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2548
_refine_ls_wR_factor_ref         0.2683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2821
_reflns_number_total             3542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00533c2.cif
_cod_data_source_block           sg_4f_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159966--7159967.cif.'
_cod_original_cell_volume        4036(16)
_cod_database_code               7159967
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.797
_shelx_estimated_absorpt_t_min   0.548
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C00P) = Uanis(C00O)
Uanis(C00O) = Uanis(C00Q)
3.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
3.b X=CH2 refined with riding coordinates:
 N006(H00A,H00B)
;
_shelx_res_checksum              9493
_olex2_submission_special_instructions 'No special instructions were received'