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_4134938
_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         'C9 H9 N3 O3'
_chemical_formula_sum            'C9 H9 N3 O3'
_chemical_formula_weight         207.19
_chemical_name_systematic
(1aR*,2S*,8R*,8aS*)-5-methyl-1a,2,8,8a-tetrahydro-4H-2,8-ethenooxireno[2,3-d][1,2,4]triazolo[1,2-a]pyridazine-4,6(5H)-dione
_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
_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                 98.206(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5594(7)
_cell_length_b                   15.3365(14)
_cell_length_c                   7.7117(7)
_cell_measurement_reflns_used    5557
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.509
_cell_measurement_theta_min      2.981
_cell_volume                     884.90(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEXII CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  Mo_ApexII
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12250
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.538
_diffrn_reflns_theta_min         3.773
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens fine-focus sealed tube'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0417 before and 0.0349 after correction. The Ratio of minimum to maximum transmission is 0.9282. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.453
_exptl_crystal_size_min          0.302
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0821P)^2^+0.1637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1306
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             2701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02724_si_005.cif
_cod_data_source_block           dm62w_0m
_cod_depositor_comments
;Adding full bibliography for 4134935--4134938.cif.

 Adding full bibliography for 4134935--4134938.cif.
;
_cod_database_code               4134938
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.939
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              43095
_shelx_hkl_checksum              80946
_olex2_date_sample_data_collection 2019-07-18
_olex2_date_sample_submission    2019-07-17
_olex2_exptl_crystal_mounting_method
'Mounted using Paratone-N oil on a Cryo-Loop with (2 2 1) face roughly perpendicular to the spindle axis'
_olex2_submission_original_sample_id D62W
_olex2_submission_special_instructions 'No special instructions were received'