#------------------------------------------------------------------------------
#$Date: 2018-01-17 01:38:42 +0200 (Wed, 17 Jan 2018) $
#$Revision: 205272 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/70/4127034.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4127034
loop_
_publ_author_name
'Zwick, Christian R.'
'Renata, Hans'
_publ_section_title
;
 Remote C-H Hydroxylation by an α-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         'C11 H19 N O4'
_chemical_formula_sum            'C11 H19 N O4'
_chemical_formula_weight         229.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-04-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.820(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0473(9)
_cell_length_b                   5.6470(3)
_cell_length_c                   12.1602(6)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.359
_cell_measurement_theta_min      3.636
_cell_volume                     1238.66(11)
_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 Platinum135 CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Platinum135'
_diffrn_measurement_method       'ω and φ 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  0.0460
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17486
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.355
_diffrn_reflns_theta_min         3.637
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.2196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1071 before and 0.0697 after correction. The Ratio of minimum to maximum transmission is 0.6862. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       Plank
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.405
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0269
_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/[σ²(Fo²)+(0.0332P)²+0.3831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                2152
_reflns_number_total             2213
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12918_si_003.cif
_cod_data_source_block           Renata03
_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               4127034
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.745
_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), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.70966(7) 0.3863(3) 0.37877(12) 0.0369(3) Uani 1 1 d .
O2 O 0.65508(7) 0.6463(3) 0.26996(10) 0.0297(3) Uani 1 1 d .
O3 O 0.56014(7) 0.3742(3) 0.63064(10) 0.0327(3) Uani 1 1 d .
O4 O 0.66317(6) 0.4472(2) 0.73937(10) 0.0261(3) Uani 1 1 d .
N1 N 0.65793(9) 0.5845(3) 0.56954(13) 0.0311(4) Uani 1 1 d D
H1 H 0.7000(11) 0.654(4) 0.5908(18) 0.032(6) Uiso 1 1 d D
C1 C 0.66754(10) 0.5516(3) 0.37023(15) 0.0262(4) Uani 1 1 d .
C2 C 0.62286(9) 0.6454(4) 0.46536(14) 0.0259(4) Uani 1 1 d .
H2 H 0.574206 0.560590 0.461761 0.031 Uiso 1 1 calc R
C3 C 0.60545(10) 0.9081(4) 0.45470(15) 0.0303(4) Uani 1 1 d .
H3A H 0.570288 0.956143 0.511438 0.036 Uiso 1 1 calc R
H3B H 0.651399 1.002294 0.465212 0.036 Uiso 1 1 calc R
C4 C 0.57147(10) 0.9518(4) 0.34063(16) 0.0310(4) Uani 1 1 d .
H4A H 0.525975 0.855363 0.330325 0.037 Uiso 1 1 calc R
H4B H 0.557538 1.120733 0.333064 0.037 Uiso 1 1 calc R
C5 C 0.62579(10) 0.8878(4) 0.25400(15) 0.0279(4) Uani 1 1 d .
H5 H 0.668107 1.002133 0.258463 0.033 Uiso 1 1 calc R
C6 C 0.59241(11) 0.8926(5) 0.13851(16) 0.0370(5) Uani 1 1 d .
H6A H 0.629472 0.840199 0.086587 0.055 Uiso 1 1 calc GR
H6B H 0.576637 1.054254 0.120094 0.055 Uiso 1 1 calc GR
H6C H 0.549466 0.786445 0.133920 0.055 Uiso 1 1 calc GR
C7 C 0.62123(10) 0.4601(3) 0.64529(14) 0.0246(4) Uani 1 1 d .
C8 C 0.63778(10) 0.3067(3) 0.83247(15) 0.0248(4) Uani 1 1 d .
C9 C 0.56441(10) 0.3991(4) 0.87261(16) 0.0316(4) Uani 1 1 d .
H9A H 0.568523 0.569317 0.887162 0.047 Uiso 1 1 calc GR
H9B H 0.551900 0.316428 0.940415 0.047 Uiso 1 1 calc GR
H9C H 0.525431 0.371077 0.816148 0.047 Uiso 1 1 calc GR
C10 C 0.63482(12) 0.0469(4) 0.80145(18) 0.0346(5) Uani 1 1 d .
H10A H 0.595192 0.021483 0.745737 0.052 Uiso 1 1 calc GR
H10B H 0.624952 -0.047981 0.866848 0.052 Uiso 1 1 calc GR
H10C H 0.682403 -0.000703 0.771704 0.052 Uiso 1 1 calc GR
C11 C 0.69873(10) 0.3519(4) 0.91915(16) 0.0340(5) Uani 1 1 d .
H11A H 0.745436 0.284616 0.894521 0.051 Uiso 1 1 calc GR
H11B H 0.685434 0.277371 0.988576 0.051 Uiso 1 1 calc GR
H11C H 0.704617 0.522852 0.930197 0.051 Uiso 1 1 calc GR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O2 C5 122.46(15)
C7 O4 C8 120.08(13)
C2 N1 H1 120.0(15)
C7 N1 H1 117.8(15)
C7 N1 C2 120.91(15)
O1 C1 O2 118.22(17)
O1 C1 C2 123.38(17)
O2 C1 C2 118.21(16)
N1 C2 C1 110.85(16)
N1 C2 H2 106.5
N1 C2 C3 113.09(17)
C1 C2 H2 106.5
C3 C2 C1 112.75(15)
C3 C2 H2 106.5
C2 C3 H3A 110.1
C2 C3 H3B 110.1
H3A C3 H3B 108.4
C4 C3 C2 108.22(16)
C4 C3 H3A 110.1
C4 C3 H3B 110.1
C3 C4 H4A 109.6
C3 C4 H4B 109.6
H4A C4 H4B 108.1
C5 C4 C3 110.31(15)
C5 C4 H4A 109.6
C5 C4 H4B 109.6
O2 C5 C4 111.64(15)
O2 C5 H5 108.7
O2 C5 C6 105.64(16)
C4 C5 H5 108.7
C4 C5 C6 113.38(15)
C6 C5 H5 108.7
C5 C6 H6A 109.5
C5 C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6B 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
O3 C7 O4 125.74(16)
O3 C7 N1 124.89(16)
N1 C7 O4 109.37(14)
O4 C8 C9 111.04(15)
O4 C8 C10 109.92(15)
O4 C8 C11 101.95(14)
C9 C8 C11 109.79(16)
C10 C8 C9 112.87(17)
C10 C8 C11 110.75(17)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C11 H11A 109.5
C8 C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.207(2)
O2 C1 1.344(2)
O2 C5 1.474(2)
O3 C7 1.212(2)
O4 C7 1.354(2)
O4 C8 1.468(2)
N1 H1 0.886(19)
N1 C2 1.440(2)
N1 C7 1.349(2)
C1 C2 1.526(3)
C2 H2 1.0000
C2 C3 1.521(3)
C3 H3A 0.9900
C3 H3B 0.9900
C3 C4 1.519(3)
C4 H4A 0.9900
C4 H4B 0.9900
C4 C5 1.506(3)
C5 H5 1.0000
C5 C6 1.511(3)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C8 C9 1.518(3)
C8 C10 1.515(3)
C8 C11 1.521(2)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.886(19) 2.12(2) 2.986(2) 167(2) 4_656
