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_4134935
_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 H10 Cl N3 O3'
_chemical_formula_sum            'C13 H10 Cl N3 O3'
_chemical_formula_weight         291.69
_chemical_name_systematic
(5S*,10R*,12R*,14S*)-6-chloro-2-methyl-5,10-dihydro-1H-5,10-[2,3]epoxireno[1,2,4]triazolo[1,2-b]phthalazine-1,3(2H)-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.8955(2)
_cell_length_b                   15.5594(4)
_cell_length_c                   21.9079(6)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      2.779
_cell_volume                     2350.50(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_type            'charge integrated pixel array'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0470
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27140
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_min         2.618
_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    0.337
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0847 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.8773.
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    1.649
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 'Rerystallized from hot ethanol'
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     756
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0294P)^2^+1.8961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2534
_reflns_number_total             2925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02724_si_004.cif
_cod_data_source_block           mo_dd03s_0m
_cod_depositor_comments
;Adding full bibliography for 4134935--4134938.cif.

 Adding full bibliography for 4134935--4134938.cif.
;
_cod_database_code               4134935
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.911
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1B-C6B \\sim Cl1A-C6A
 with sigma of 0.01
 O1B-C2B \\sim O1A-C3A \\sim O1B-C3B \\sim O1A-C2A
 with sigma of 0.01
 O3B-C11B \\sim O3A-C12A \\sim O2B-C12B \\sim O2A-C11A
 with sigma of 0.01
 C8B-C7B \\sim C8A-C7A
 with sigma of 0.01
 C8B-C9B \\sim C6A-C7A \\sim C6B-C7B \\sim C8A-C9A
 with sigma of 0.01
 N3B-C13B \\sim N3A-C13A
 with sigma of 0.01
 C9B-C10B \\sim C6A-C5A \\sim C6B-C5B \\sim C9A-C10A
 with sigma of 0.01
 N2B-N1B \\sim N1A-N2A
 with sigma of 0.01
 C10B-C5B \\sim C10A-C5A
 with sigma of 0.01
 N2B-C11B \\sim N2A-C12A \\sim N1B-C12B \\sim N1A-C11A
 with sigma of 0.01
 C10B-C1B \\sim C4A-C5A \\sim C4B-C5B \\sim C10A-C1A
 with sigma of 0.01
 N3B-C11B \\sim N3A-C12A \\sim N3B-C12B \\sim N3A-C11A
 with sigma of 0.01
 N2B-C1B \\sim N2A-C4A \\sim N1B-C4B \\sim N1A-C1A
 with sigma of 0.01
 C2B-C3B \\sim C2A-C3A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
Uanis(C13B) = Uanis(C13A)
4. Others
 Sof(Cl1B)=Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(N1B)=Sof(N2B)=Sof(N3B)=Sof(C1B)=
 Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=
 Sof(C6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=
 Sof(C11B)=Sof(C12B)=Sof(C13B)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(Cl1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(N1A)=Sof(N2A)=Sof(N3A)=Sof(C1A)=
 Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=
 Sof(C11A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Free rotating group:
 Cl1B(O1B,O2B,O3B,N1B,N2B,N3B,C1B,C2B,C3B,C4B,C5B,C6B,C7B,C8B,C9B,C10B,C11B,
 C12B,C13B)
5.b Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B)
5.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C7B(H7B), C8B(H8B), C9B(H9B)
5.d Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F)
;
_shelx_res_checksum              3905
_shelx_hkl_checksum              60730
_olex2_date_sample_data_collection 2018-12-10
_olex2_date_sample_submission    2018-12-07
_olex2_exptl_crystal_mounting_method
'Mounted using Paratone-N oil on a Cryo-Loop with (0 3 2) face roughly perpendicular to the spindle axis'
_olex2_submission_original_sample_id D03S
_olex2_submission_special_instructions 'No special instructions were received'