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_1558129
_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         'C41 H45 N O'
_chemical_formula_sum            'C41 H45 N O'
_chemical_formula_weight         567.78
_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
_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                90
_cell_angle_beta                 94.419(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.001(3)
_cell_length_b                   10.5247(15)
_cell_length_c                   22.239(4)
_cell_measurement_reflns_used    6592
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      2.50
_cell_volume                     3500.7(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      223.12
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1248
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            54795
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.366
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1187 before and 0.0609 after correction. The Ratio of minimum to maximum transmission is 0.8480. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_description       needle
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1690
_refine_ls_R_factor_gt           0.0893
_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^)+(0.0979P)^2^+3.3179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3200
_reflns_number_total             6175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01373k4.cif
_cod_data_source_block           aks162a_0m_a
_cod_depositor_comments
'Adding full bibliography for 1558127--1558129.cif.'
_cod_original_cell_volume        3500.6(9)
_cod_database_code               1558129
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.988
_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:
 C00V(H00A,H00B), C00X(H00C,H00E), C00Y(H00L,H00O), C011(H01D,H01E)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q),
 C00T(H00T)
2.c Idealised Me refined as rotating group:
 C00Z(H00R,H00S,H00U), C010(H01A,H01B,H01C), C012(H01F,H01G,H01H), C013(H01I,
 H01J,H01K), C014(H01L,H01M,H01N), C015(H01O,H01P,H01Q), C016(H01R,H01S,H01T),
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              28141
_olex2_submission_special_instructions 'No special instructions were received'