# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14srv135
_database_code_depnum_ccdc_archive 'CCDC 1050160'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;
_audit_creation_date             2014-05-01
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 dimethyl fluoromalonate
;
_chemical_formula_moiety         'C5 H7 F O4'
_chemical_formula_sum            'C5 H7 F O4'
_chemical_formula_weight         150.11
_chemical_melting_point          303
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   6.1459(4)
_cell_length_b                   10.5542(6)
_cell_length_c                   9.5004(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.777(2)
_cell_angle_gamma                90.00
_cell_volume                     614.91(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2404
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.76
_cell_measurement_theta_min      2.89
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_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_meas      .
_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
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 3 sets of ω scans each set at different φ 
 angles and each scan (3 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_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_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_source                   'fine-focus sealed tube'
_diffrn_source_current           10.0
_diffrn_source_power             0.3
_diffrn_source_target            Mo
_diffrn_source_voltage           30.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1301
_reflns_number_total             1712
_reflns_threshold_expression     >2sigma(I)
_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)'
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       ?
_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_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.045
_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
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0173(5) 0.0314(6) 0.0300(6) -0.0045(4) 0.0000(4) 0.0036(4)
O1 0.0233(6) 0.0230(6) 0.0272(6) -0.0033(5) 0.0011(5) -0.0032(5)
O2 0.0188(6) 0.0226(6) 0.0277(6) -0.0048(5) 0.0037(5) -0.0002(4)
O3 0.0238(6) 0.0260(7) 0.0240(6) -0.0001(5) 0.0045(5) 0.0004(5)
O4 0.0188(6) 0.0295(7) 0.0207(6) -0.0002(5) 0.0009(4) -0.0016(4)
C1 0.0168(8) 0.0207(8) 0.0214(8) 0.0005(6) 0.0008(6) 0.0003(6)
C2 0.0198(8) 0.0202(8) 0.0196(7) 0.0016(6) 0.0015(6) 0.0011(6)
C3 0.0231(8) 0.0230(8) 0.0272(9) -0.0044(7) 0.0028(7) 0.0038(7)
C4 0.0186(8) 0.0153(7) 0.0231(8) 0.0011(6) 0.0007(6) 0.0001(5)
C5 0.0217(8) 0.0319(9) 0.0232(8) -0.0016(7) -0.0017(6) -0.0011(7)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_iucr_refine_instructions_details 
;
TITL 14srv135 in P21/c #14
CELL 0.71073 6.1459 10.5542 9.5004 90 93.777 90
ZERR 4 0.0004 0.0006 0.0005 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z

SFAC C H O F
UNIT 20 28 16 4


L.S. 9
PLAN  5
TEMP 120
REM reset to P21/c #14
BOND $h
CONF 
fmap 2 53
acta 
OMIT -2 59
REM <HKL>D:/Struc/14S/14srv135/14srv135.hkl</HKL>
WGHT 0.11 0.14
FVAR 0.40914

F1    4     1.23299  0.38083  0.24195  11.00000  0.01729  0.03140  0.02998 =
 -0.00447  0.00002  0.00359 
O1    3     1.05161  0.58112  0.35083  11.00000  0.02327  0.02304  0.02724 =
 -0.00326  0.00108 -0.00321 
O2    3     0.71963  0.49064  0.32754  11.00000  0.01884  0.02260  0.02767 =
 -0.00484  0.00368 -0.00024 
O3    3     1.03566  0.35715 -0.01198  11.00000  0.02385  0.02605  0.02403 =
 -0.00008  0.00447  0.00039 
O4    3     0.70560  0.35366  0.07919  11.00000  0.01879  0.02948  0.02066 =
 -0.00016  0.00092 -0.00164 
C1    1     1.00871  0.37700  0.23927  11.00000  0.01683  0.02074  0.02144 =
 0.00048  0.00080  0.00026 
C2    1     0.93155  0.49633  0.31151  11.00000  0.01975  0.02017  0.01965 =
 0.00164  0.00151  0.00107 
C3    1     0.62619  0.60123  0.39241  11.00000  0.02307  0.02301  0.02721 =
 -0.00445  0.00278  0.00378 
C4    1     0.92150  0.36190  0.08522  11.00000  0.01860  0.01528  0.02305 =
 0.00109  0.00066  0.00008 
C5    1     0.59950  0.34460 -0.06192  11.00000  0.02169  0.03188  0.02315 =
 -0.00164 -0.00174 -0.00108 
H1    2     0.97077  0.30332  0.29135  11.00000  0.02225 
H3a   2     0.68688  0.60452  0.48732  11.00000  0.02812 
H3b   2     0.47269  0.58501  0.39181  11.00000  0.02652 
H3c   2     0.65613  0.67351  0.33935  11.00000  0.01776 
H5a   2     0.62909  0.26636 -0.09604  11.00000  0.02097 
H5b   2     0.44960  0.35287 -0.05296  11.00000  0.02208 
H5c   2     0.64499  0.41182 -0.12312  11.00000  0.03835 
HKLF 4
END

;
