Chemical Equivalent of Arene Monooxygenases: Dearomative Synthesis of Arene Oxides and Oxepines.
Siddiqi, Zohaib; Wertjes, William C.; Sarlah, David; Journal of the American Chemical Society 142 (2020) 10125–10131; doi:10.1021/jacs.0c02724

data_4134937
_publ_section_title
;
 Chemical Equivalent of Arene Monooxygenases: Dearomative Synthesis of
 Arene Oxides and Oxepines.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10125
_journal_page_last               10131
_journal_paper_doi               10.1021/jacs.0c02724
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C10 H8 O'
_chemical_formula_sum            'C10 H8 O'
_chemical_formula_weight         144.16
_chemical_name_systematic        benzo[d]oxepine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.3054(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8858(2)
_cell_length_b                   6.0451(2)
_cell_length_c                   8.4347(3)
_cell_measurement_reflns_used    6743
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.243
_cell_measurement_theta_min      4.289
_cell_volume                     366.45(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_type            'charge integrated pixel array'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8457
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.270
_diffrn_reflns_theta_min         4.289
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1154 before and 0.0378 after correction. The Ratio of minimum to maximum transmission is 0.9511. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             152
_exptl_crystal_recrystallization_method
'Crystallized from methanol by slow evaporation'
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         901
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0469P)^2^+0.1052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                870
_reflns_number_total             901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02724_si_002.cif
_cod_data_source_block           14
_cod_depositor_comments
;Adding full bibliography for 4134935--4134938.cif.

 Adding full bibliography for 4134935--4134938.cif.
;
_cod_database_code               4134937
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C3-C2 = C10-C11
 1.317 with sigma of 0.02
 O1-C2 \\sim O1-C11
 with sigma of 0.01
 C3-C2 \\sim C10-C11
 with sigma of 0.01
 C5-C4 \\sim C9-C4 \\sim C9-C8 \\sim C8-C7 \\sim C7-C6 \\sim C6-C5
 with sigma of 0.01
 C4-C3 \\sim C9-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C5)
Uanis(C3) = Uanis(C8)
4. Rigid body (RIGU) restrains
 O1, C2, C3, C4, C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5) C4(0.5) C5(0.5) H5(0.5)
 C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) C10(0.5) H10(0.5)
 C11(0.5) H11(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
;
_shelx_res_checksum              32845
_shelx_hkl_checksum              58683
_olex2_date_sample_data_collection 2019-04-08
_olex2_date_sample_submission    2019-04-05
_olex2_exptl_crystal_mounting_method
'Mounted using Krytox oil on a Cryo-Loop with (5 -2 1) face roughly perpendicular to the spindle axis'
_olex2_submission_original_sample_id D64U
_olex2_submission_special_instructions 'No special instructions were received'