Double annulation of ortho- and peri-C‒H bonds of fused (hetero)arenes to unusual oxepino-pyridines
Shankar, Majji; Rit, Raja K.; Sau, Somratan; Mukherjee, Kallol; Gandon, Vincent; Sahoo, Akhila K.; Chemical Science 11 (2020) 10770–10777; doi:10.1039/D0SC01373K

data_1558128
_publ_section_title
;
 Double annulation of ortho- and peri-C--H bonds of fused (hetero)arenes
 to unusual oxepino-pyridines
;
_journal_issue                   39
_journal_name_full               'Chemical Science'
_journal_page_first              10770
_journal_page_last               10777
_journal_paper_doi               10.1039/D0SC01373K
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C28 H23 Cl N O2'
_chemical_formula_sum            'C28.48 H23 Cl N O2'
_chemical_formula_weight         446.72
_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     dual
_audit_creation_date             2020-01-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2020-01-22 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.961(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5781(4)
_cell_length_b                   9.3138(3)
_cell_length_c                   18.8307(6)
_cell_measurement_reflns_used    9463
_cell_measurement_temperature    295.5(4)
_cell_measurement_theta_max      26.0260
_cell_measurement_theta_min      2.1630
_cell_volume                     2547.21(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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_environment      air
_diffrn_ambient_temperature      295.5(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.957
_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    -62.00   1.00   0.50    8.76    --  -14.97 -45.00 -30.00  126
  2  \w     42.00  68.00   0.50    8.76    --   16.22-150.00  54.00   52
  3  \w    -10.00  34.00   0.50    8.76    --   16.22 -30.00  90.00   88
  4  \w    -34.00  -5.00   0.50    8.76    --  -14.97 -94.00  90.00   58
  5  \w    -57.00 -27.00   0.50    8.76    --   16.22 -30.00  90.00   60
  6  \w    -84.00  -1.00   0.50    8.76    --  -14.97 -61.00  60.00  166
  7  \w    -89.00 -17.00   0.50    8.76    --  -14.97 -30.00 -30.00  144
  8  \w    -57.00 -32.00   0.50    8.76    --  -14.97 122.00 -61.00   50
  9  \w     14.00  39.00   0.50    8.76    --   16.22-122.00-143.00   50
 10  \w    -27.00  22.00   0.50    8.76    --  -14.97 -94.00-150.00   98
 11  \w    -25.00  53.00   0.50    8.76    --   16.22 -94.00-150.00  156
 12  \w    -69.00 -35.00   0.50    8.76    --  -14.97 125.00 -30.00   68
 13  \w    -77.00 -51.00   0.50    8.76    --  -14.97 150.00 100.00   52
 14  \w      3.00  30.00   0.50    8.76    --   16.22  61.00 120.00   54
 15  \w     50.00  85.00   0.50    8.76    --   16.22  61.00 120.00   70
 16  \w     10.00  35.00   0.50    8.76    --   16.22 -45.00 150.00   50
 17  \w    -53.00 -26.00   0.50    8.76    --   16.22 -45.00 150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0076420000
_diffrn_orient_matrix_UB_12      -0.0165585000
_diffrn_orient_matrix_UB_13      -0.0368081000
_diffrn_orient_matrix_UB_21      0.0068517000
_diffrn_orient_matrix_UB_22      -0.0739236000
_diffrn_orient_matrix_UB_23      0.0078368000
_diffrn_orient_matrix_UB_31      -0.0477329000
_diffrn_orient_matrix_UB_32      -0.0079548000
_diffrn_orient_matrix_UB_33      0.0036727000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22700
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.970
_diffrn_reflns_theta_min         2.171
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0863
_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^)+(0.1615P)^2^+0.6908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2665
_refine_ls_wR_factor_ref         0.3098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3016
_reflns_number_total             5299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01373k4.cif
_cod_data_source_block           aks43
_cod_depositor_comments
'Adding full bibliography for 1558127--1558129.cif.'
_cod_database_code               1558128
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.62
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00B), C00K(H00C,H00D), C00M(H00E,H00F), C00O(H00L,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00G(H00G), C00H(H00H)
2.c Idealised Me refined as rotating group:
 C00N(H00I,H00J,H00K), C00P(H00N,H00O,H00P), C00U(H00Q,H00R,H00S), C00V(H00T,
 H00U,H00V)
;
_shelx_res_checksum              22218
_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 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.462