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_4134936
_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         'C13 H8 Cl F3 N4 O3, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C13.5 H9 Cl2 F3 N4 O3'
_chemical_formula_weight         403.15
_chemical_name_systematic
(5R*,11S*,12S*,14R*)-4-chloro-8-methyl-2-(trifluoromethyl)-5,11-dihydro-7H-11,5-[2,3]epoxirenopyrido[2,3-d][1,2,4]triazolo[1,2-a]pyridazine-7,9(8H)-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_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                 119.6990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.6871(11)
_cell_length_b                   6.8296(3)
_cell_length_c                   21.0493(9)
_cell_measurement_reflns_used    69154
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      28.323
_cell_measurement_theta_min      3.131
_cell_volume                     3082.8(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  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_type            'charge integrated pixel array'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  DUO_PhotonII_Mo
_diffrn_measurement_method       'profile data from \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  0.0364
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            100114
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.337
_diffrn_reflns_theta_min         3.130
_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    0.479
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.9091.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_description       prism
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.709
_exptl_crystal_size_mid          0.614
_exptl_crystal_size_min          0.567
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+4.2149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3673
_reflns_number_total             3825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02724_si_003.cif
_cod_data_source_block           ed27a_0m_2
_cod_depositor_comments
;Adding full bibliography for 4134935--4134938.cif.

 Adding full bibliography for 4134935--4134938.cif.
;
_cod_original_formula_sum        'C13.50 H9 Cl2 F3 N4 O3'
_cod_database_code               4134936
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.773
_shelx_estimated_absorpt_t_min   0.727
_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. Restrained distances
 Cl2-C30 \\sim C30-Cl3
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim Cl3 \\sim C30: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Fixed Sof: Cl2(0.5) Cl3(0.5) C30(0.5) H30A(0.5) H30B(0.5)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              58216
_shelx_hkl_checksum              65852
_olex2_date_sample_data_collection 2019-12-17
_olex2_date_sample_submission    2019-12-16
_olex2_exptl_crystal_mounting_method
'Mounted using Paratone-N oil on a Cryo-Loop with (7 1 -7) face roughly perpendicular to the spindle axis'
_olex2_submission_original_sample_id D27A
_olex2_submission_special_instructions 'No special instructions were received'