Sustainable synthesis of enantiopure fluorolactam derivatives by a selective direct fluorination – amidase strategy
Willis, Nicky J.; Fisher, Craig A.; Alder, Catherine M.; Harsanyi, Antal; Shukla, Lena; Adams, Joseph P.; Sandford, Graham; Green Chem. 18 (2016) 1313–; doi:10.1039/C5GC02209F

data_7222916
_publ_section_title
;
 Sustainable synthesis of enantiopure fluorolactam derivatives by a
 selective direct fluorination -- amidase strategy
;
_journal_issue                   5
_journal_name_full               'Green Chem.'
_journal_page_first              1313
_journal_paper_doi               10.1039/C5GC02209F
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H10 F N O3'
_chemical_formula_sum            'C7 H10 F N O3'
_chemical_formula_weight         175.16
_chemical_melting_point          388.6(5)
_chemical_name_systematic
;
(S)-methyl 3-fluoro-2-oxopiperidine-3-carboxylate 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_audit_update_record
;
2015-05-20 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3404(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5224(4)
_cell_length_b                   10.3050(5)
_cell_length_c                   9.1442(4)
_cell_measurement_reflns_used    8801
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.47
_cell_measurement_theta_min      4.29
_cell_volume                     803.06(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7399
_diffrn_reflns_theta_full        72.46
_diffrn_reflns_theta_max         72.46
_diffrn_reflns_theta_min         4.84
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1189 before and 0.0931 after correction.
The Ratio of minimum to maximum transmission is 0.8291.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                2829
_reflns_number_total             2833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5gc02209f6.cif
_cod_data_source_block           2b_14srv257
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '115-116 C' was changed to '388.6(5)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7222916--7222921.cif.
;
_cod_database_code               7222916
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
;