Minimising conformational bias in fluoroprolines through vicinal difluorination.
Hofman, Gert-Jan; Ottoy, Emile; Light, Mark E.; Kieffer, Bruno; Kuprov, Ilya; Martins, Jose C.; Sinnaeve, Davy; Linclau, Bruno; Chemical communications (Cambridge, England) 54 (2018) 5118–5121; doi:10.1039/c8cc01493k

data_7121515
_publ_section_title
;
 Minimising conformational bias in fluoroprolines through vicinal
 difluorination.
;
_journal_issue                   40
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5118
_journal_page_last               5121
_journal_paper_doi               10.1039/c8cc01493k
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H21 F2 N O4'
_chemical_formula_sum            'C17 H21 F2 N O4'
_chemical_formula_weight         341.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_audit_update_record
;
2017-02-07 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3962(3)
_cell_length_b                   10.8390(3)
_cell_length_c                   33.4374(9)
_cell_measurement_reflns_used    6173
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.9330
_cell_measurement_theta_min      3.9500
_cell_volume                     3405.45(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -108.00  11.00   1.00   20.00    --  -19.00 -57.00-150.00  119
  2  \w     10.00  53.00   1.00   20.00    --  -19.00  57.00-120.00   43
  3  \w   -106.00  38.00   1.00   20.00    --  -19.00 -19.00-150.00  144
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0248158000
_diffrn_orient_matrix_UB_12      -0.0341070000
_diffrn_orient_matrix_UB_13      0.0167118000
_diffrn_orient_matrix_UB_21      0.0159396000
_diffrn_orient_matrix_UB_22      0.0558461000
_diffrn_orient_matrix_UB_23      0.0100979000
_diffrn_orient_matrix_UB_31      -0.0694624000
_diffrn_orient_matrix_UB_32      0.0006130000
_diffrn_orient_matrix_UB_33      0.0083064000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            24677
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         3.760
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       rod
_exptl_crystal_F_000             1440
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         8447
_refine_ls_number_restraints     367
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0703
_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^)+(0.0377P)^2^+0.5474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                6864
_reflns_number_total             8447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01493k2.cif
_cod_data_source_block           2017sot0006_k1_100k
_cod_depositor_comments          'Adding full bibliography for 7121515.cif.'
_cod_database_code               7121515
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C17H21F2N1O4
_chemical_oxdiff_usercomment     GJH-7985-56
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C102(H102), C103(H103), C104(H104), C202(H202), C203(H203), C204(H204)
3.b Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B), C106(H10C,H10D), C201(H20A,H20B), C206(H20C,H20D)
3.c Aromatic/amide H refined with riding coordinates:
 C108(H108), C109(H109), C110(H110), C111(H111), C112(H112), C208(H208),
 C209(H209), C210(H210), C211(H211), C212(H212)
3.d Idealised Me refined as rotating group:
 C115(H11A,H11B,H11C), C116(H11D,H11E,H11F), C117(H11G,H11H,H11I), C215(H21A,
 H21B,H21C), C216(H21D,H21E,H21F), C217(H21G,H21H,H21I)
;
_olex2_date_sample_submission    2017-01-31
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder silicon oil'
_olex2_submission_original_sample_id GJH-7985-56
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.659