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_1558127
_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         'C33 H37 N O'
_chemical_formula_sum            'C33 H37 N O'
_chemical_formula_weight         463.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-02
_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                81.166(6)
_cell_angle_beta                 67.584(6)
_cell_angle_gamma                72.381(7)
_cell_formula_units_Z            2
_cell_length_a                   10.7051(8)
_cell_length_b                   10.9218(9)
_cell_length_c                   12.9779(4)
_cell_measurement_reflns_used    7996
_cell_measurement_temperature    197(130)
_cell_measurement_theta_max      26.1930
_cell_measurement_theta_min      2.1300
_cell_volume                     1335.66(17)
_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      N~2~
_diffrn_ambient_temperature      197(130)
_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 0.999
_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     -6.00  45.00   0.50    2.80    --   16.22  30.00  30.00  102
  2  \w     51.00  77.00   0.50    2.80    --   16.22  30.00  30.00   52
  3  \w     15.00  55.00   0.50    2.80    --  -14.97  45.00  60.00   80
  4  \w    -27.00   9.00   0.50    2.80    --  -14.97  45.00  60.00   72
  5  \w    -57.00 -19.00   0.50    2.80    --  -14.97 108.00   1.00   76
  6  \w    -16.00  46.00   0.50    2.80    --   16.22 -77.00  90.00  124
  7  \w     21.00  62.00   0.50    2.80    --   16.22-125.00  30.00   82
  8  \w     18.00  44.00   0.50    2.80    --   16.22 -94.00 -60.00   52
  9  \w     -3.00  61.00   0.50    2.80    --   16.22-108.00 -95.00  128
 10  \w     -7.00  44.00   0.50    2.80    --   16.22 -61.00-120.00  102
 11  \w     -4.00  30.00   0.50    2.80    --   16.22 -45.00-120.00   68
 12  \w    -42.00 -16.00   0.50    2.80    --  -14.97  61.00-150.00   52
 13  \w     27.00  54.00   0.50    2.80    --  -14.97  61.00-150.00   54
 14  \w    -39.00 -13.00   0.50    2.80    --   16.22 130.00-136.68   52
 15  \w    -75.00 -50.00   0.50    2.80    --  -14.97 -30.00 -90.00   50
 16  \w    -46.00   6.00   0.50    2.80    --  -14.97 -30.00 -90.00  104
 17  \w    -37.00 -10.00   0.50    2.80    --   16.22 -94.00 -60.00   54
 18  \w    -57.00  41.00   0.50    2.80    --   16.22 -30.00   0.00  196
 19  \w    -34.00  20.00   0.50    2.80    --  -14.97 -94.00  90.00  108
 20  \w    -31.00  24.00   0.50    2.80    --   16.22 -45.00 150.00  110
 21  \w    -53.00  43.00   0.50    2.80    --   16.22 -61.00 150.00  192
 22  \w    -84.00 -24.00   0.50    2.80    --  -14.97 -30.00  60.00  120
 23  \w    -66.00 -31.00   0.50    2.80    --  -14.97 125.00   0.00   70
 24  \w    -61.00 -36.00   0.50    2.80    --  -14.97 125.00 120.00   50
 25  \w    -49.00 -21.00   0.50    2.80    --   16.22 -61.00-120.00   56
;
_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      -0.0133500000
_diffrn_orient_matrix_UB_12      -0.0276029000
_diffrn_orient_matrix_UB_13      -0.0394740000
_diffrn_orient_matrix_UB_21      -0.0280420000
_diffrn_orient_matrix_UB_22      -0.0443062000
_diffrn_orient_matrix_UB_23      0.0419558000
_diffrn_orient_matrix_UB_31      -0.0675848000
_diffrn_orient_matrix_UB_32      0.0438951000
_diffrn_orient_matrix_UB_33      0.0135446000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16862
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.958
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83269
_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    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0841
_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^)+(0.1621P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2515
_refine_ls_wR_factor_ref         0.2861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2928
_reflns_number_total             4712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01373k4.cif
_cod_data_source_block           aks47
_cod_depositor_comments
'Adding full bibliography for 1558127--1558129.cif.'
_cod_database_code               1558127
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.16
_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,H00E), C00N(H00G,H00H), C00P(H00J,H00K), C00R(H00N,
 H00P), C00T(H00R,H00T), C00V(H00X,H00Y), C00W(H00Z,H)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00D(H00D), C00F(H00F), C00I(H00I), C00L(H00L), C00M(H00M),
 C00O(H00O), C00Q(H00Q), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00U(H00U,H00V,H00W), C00X(H00,HA,HB), C00Y(H0AA,HC,HD), C00Z(H1AA,HE,HF)
;
_shelx_res_checksum              61464
_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 1.543
_oxdiff_exptl_absorpt_empirical_full_min 0.501