The Hofmann reaction involving annulation of o-(pyridin-2-yl)aryl amides selectively and rapidly leads to potential photocatalytically active 6H-pyrido[1,2-c]quinazolin-6-one derivatives
Gao, Wenjing; Wan, Yameng; Zhang, Zhiguo; Wu, Hao; Liu, Tongxin; Zhang, Guisheng; Green Chemistry 22 (2020) 7955–7961; doi:10.1039/D0GC02777D

data_7241334
_publ_section_title
;
 The Hofmann reaction involving annulation of o-(pyridin-2-yl)aryl amides
 selectively and rapidly leads to potential photocatalytically active
 6H-pyrido[1,2-c]quinazolin-6-one derivatives
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              7955
_journal_page_last               7961
_journal_paper_doi               10.1039/D0GC02777D
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'B F4, C13 H11 N2 O'
_chemical_formula_sum            'C13 H11 B F4 N2 O'
_chemical_formula_weight         298.05
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2020-09-25 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3539(5)
_cell_length_b                   10.9951(6)
_cell_length_c                   11.0590(7)
_cell_measurement_reflns_used    2014
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1500
_cell_measurement_theta_min      3.9270
_cell_volume                     1258.98(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     12.00  71.00   1.00    6.01    --   16.13-144.00-147.00   59
  2  \w    -42.00 -17.00   1.00    6.01    --  -16.83  88.00  25.00   25
  3  \w     11.00  82.00   1.00    6.01    --   16.13  57.00  90.00   71
  4  \w     39.00  89.00   1.00    6.01    --   16.13-178.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0349422000
_diffrn_orient_matrix_UB_12      0.0491456000
_diffrn_orient_matrix_UB_13      0.0256366000
_diffrn_orient_matrix_UB_21      -0.0587772000
_diffrn_orient_matrix_UB_22      -0.0311732000
_diffrn_orient_matrix_UB_23      -0.0110560000
_diffrn_orient_matrix_UB_31      0.0042309000
_diffrn_orient_matrix_UB_32      -0.0277764000
_diffrn_orient_matrix_UB_33      0.0577637000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4515
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.115
_diffrn_reflns_theta_max         25.115
_diffrn_reflns_theta_min         3.271
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0443
_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^)+(0.1032P)^2^+0.3901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1345
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.761
_reflns_Friedel_fraction_max     0.761
_reflns_number_gt                1768
_reflns_number_total             1997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02777d2.cif
_cod_data_source_block           wym-20200924
_cod_depositor_comments          'Adding full bibliography for 7241334.cif.'
_cod_database_code               7241334
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1 B1'
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.955
_diffrn_oxdiff_digest_frames
;
011e637b5571e001d81ace50f91e8b8f63000303fe2
;
_diffrn_oxdiff_digest_hkl
;
014164ec5542d789307844a326e2cc208b9d64
;
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C15(H15), C10(H10), C16(H16), C8(H8), C11(H11), C9(H9)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              71676
_olex2_date_sample_data_collection 2020-09-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.551