Remote C-H Hydroxylation by an α-Ketoglutarate-Dependent Dioxygenase Enables Efficient Chemoenzymatic Synthesis of Manzacidin C and Proline Analogs.
Zwick, Christian R.; Renata, Hans; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b12918

data_4127033
_publ_section_title
;
 Remote C-H Hydroxylation by an \a-Ketoglutarate-Dependent Dioxygenase
 Enables Efficient Chemoenzymatic Synthesis of Manzacidin C and Proline
 Analogs.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12918
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-04-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3991(7)
_cell_length_b                   5.7528(4)
_cell_length_c                   13.4124(9)
_cell_measurement_reflns_used    9510
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.129
_cell_measurement_theta_min      3.304
_cell_volume                     877.22(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14892
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.706
_diffrn_reflns_theta_min         3.304
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.5210
_exptl_absorpt_correction_T_min  0.3862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1483 before and 0.0817 after correction. The Ratio of minimum to maximum transmission is 0.7413. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       Needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0682P)^2^+0.0953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                2815
_reflns_number_total             3094
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b12918_si_002.cif
_cod_data_source_block           Renata02
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4127033
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.758
_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
 N1-H1
 0.95 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              95988
_shelx_hkl_checksum              61714
_olex2_submission_special_instructions 'No special instructions were received'