#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:08:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180530 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/99/7219929.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_7219929
loop_
_publ_author_name
'Harsanyi, Antal'
'Sandford, Graham'
_publ_section_title
;
 Fluorine gas for life science syntheses: green metrics to assess
 selective direct fluorination for the synthesis of 2-fluoromalonate
 esters
;
_journal_issue                   5
_journal_name_full               'Green Chem.'
_journal_page_first              3000
_journal_paper_doi               10.1039/C5GC00402K
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C5 H7 F O4'
_chemical_formula_sum            'C5 H7 F O4'
_chemical_formula_weight         150.11
_chemical_melting_point          303
_chemical_name_systematic
;
 dimethyl fluoromalonate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-01
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.777(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1459(4)
_cell_length_b                   10.5542(6)
_cell_length_c                   9.5004(5)
_cell_measurement_reflns_used    2404
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.76
_cell_measurement_theta_min      2.89
_cell_volume                     614.91(6)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7142
_diffrn_reflns_theta_full        29.49
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           10.0
_diffrn_source_power             0.3
_diffrn_source_target            Mo
_diffrn_source_voltage           30.0
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   none
_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    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0568
_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/[σ²(Fo²)+(0.1100P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1716
_reflns_number_gt                1301
_reflns_number_total             1712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5gc00402k2.cif
_cod_data_source_block           14srv135
_cod_depositor_comments          'Adding full bibliography for 7219929.cif.'
_cod_database_code               7219929
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
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_calc_flag
F1 F 1.23299(16) 0.38083(10) 0.24195(11) 0.0263(3) Uani 1 d
O1 O 1.05161(19) 0.58112(12) 0.35083(13) 0.0245(3) Uani 1 d
O2 O 0.71963(19) 0.49064(11) 0.32754(13) 0.0229(3) Uani 1 d
O3 O 1.0357(2) 0.35715(12) -0.01198(13) 0.0245(3) Uani 1 d
O4 O 0.7056(2) 0.35366(12) 0.07919(13) 0.0230(3) Uani 1 d
C1 C 1.0087(3) 0.37700(16) 0.23927(17) 0.0197(4) Uani 1 d
C2 C 0.9315(3) 0.49633(15) 0.31151(16) 0.0198(4) Uani 1 d
C3 C 0.6262(3) 0.60123(17) 0.39241(19) 0.0244(4) Uani 1 d
C4 C 0.9215(3) 0.36190(14) 0.08522(17) 0.0190(4) Uani 1 d
C5 C 0.5995(3) 0.34460(19) -0.06192(19) 0.0257(4) Uani 1 d
H1 H 0.971(3) 0.303(2) 0.291(2) 0.022(5) Uiso 1 d
H3A H 0.687(4) 0.605(2) 0.487(3) 0.028(6) Uiso 1 d
H3B H 0.473(4) 0.585(2) 0.392(2) 0.027(5) Uiso 1 d
H3C H 0.656(3) 0.674(2) 0.339(2) 0.018(5) Uiso 1 d
H5A H 0.629(3) 0.266(2) -0.096(2) 0.021(5) Uiso 1 d
H5B H 0.450(4) 0.3529(19) -0.053(2) 0.022(5) Uiso 1 d
H5C H 0.645(4) 0.412(3) -0.123(3) 0.038(6) Uiso 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C2 O2 C3 115.55(13)
C4 O4 C5 115.48(13)
F1 C1 C2 107.93(13)
F1 C1 C4 107.89(13)
F1 C1 H1 106.9(12)
C2 C1 C4 114.58(13)
C2 C1 H1 110.1(12)
C4 C1 H1 109.1(13)
O1 C2 O2 125.89(15)
O1 C2 C1 123.46(15)
O2 C2 C1 110.62(13)
O2 C3 H3A 106.8(14)
O2 C3 H3B 105.7(14)
O2 C3 H3C 109.1(13)
H3A C3 H3B 109.6(19)
H3A C3 H3C 113.6(18)
H3B C3 H3C 111.7(19)
O3 C4 O4 126.81(15)
O3 C4 C1 123.70(15)
O4 C4 C1 109.49(14)
O4 C5 H5A 107.5(13)
O4 C5 H5B 107.1(14)
O4 C5 H5C 112.0(15)
H5A C5 H5B 109.8(18)
H5A C5 H5C 112(2)
H5B C5 H5C 108.1(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.3775(18)
O1 C2 1.204(2)
O2 C2 1.3226(19)
O2 C3 1.456(2)
O3 C4 1.197(2)
O4 C4 1.3272(19)
O4 C5 1.455(2)
C1 C2 1.525(2)
C1 C4 1.533(2)
C1 H1 0.96(2)
C3 H3A 0.95(2)
C3 H3B 0.96(2)
C3 H3C 0.94(2)
C5 H5A 0.91(2)
C5 H5B 0.93(2)
C5 H5C 0.97(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
F1 C1 C2 O1 5.8(2)
F1 C1 C2 O2 -172.34(12)
F1 C1 C4 O3 -1.2(2)
F1 C1 C4 O4 177.96(12)
C2 C1 C4 O3 118.98(17)
C2 C1 C4 O4 -61.81(17)
C3 O2 C2 O1 3.3(2)
C3 O2 C2 C1 -178.51(13)
C4 C1 C2 O1 -114.35(18)
C4 C1 C2 O2 67.46(17)
C5 O4 C4 O3 -3.4(2)
C5 O4 C4 C1 177.39(14)
