data_global
#data_New_Global_Publ_Block



_publ_contact_author_address
;
Department of Chemistry
Durham University
South Rd
Durham
DH1 3LE
UK
;
_publ_contact_author_email        d.s.yufit@durham.ac.uk
_publ_contact_author_name         'Dmitry Yufit'
_publ_contact_author_phone        ?

_publ_requested_journal           'Beilstein JOC'
_publ_section_title
;
Syntheses of fluoro-oxindole and 2-fluoro-2arylacetic acid derivatives
from diethyl 2-fluoromalonate ester
;

_publ_contact_letter
;
The CIF file contains data for the structures 3,6a and 7 from
the paper 

"Syntheses of fluoro-oxindole and 2-fluoro-2arylacetic acid derivatives
from diethyl 2-fluoromalonate ester"

by A.Harsanyi, G.Sandford, D.S.Yufit and J.A.K.Howard. 

The paper will be submitted to Beilstein Journal of Organic Chemistry shortly. 
;
loop_
_publ_author_name
_publ_author_address
'Harsanyi, Antal'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
'Sandford,Graham'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
'Yufit, Dmitry S.'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
'Howard, Judith A.K.'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
#==END

data_3_12srv156
_audit_creation_date              2012-08-22
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.08.15 svn.r2450, GUI svn.r4314)
;
_chemical_name_common             ?
_chemical_name_systematic
;
Diethyl 2-fluoro-2-(2-nitrophenyl)-malonate
;
_chemical_formula_moiety          'C13 H14 F N O6'
_chemical_formula_sum             'C13 H14 F N O6'
_chemical_formula_weight          299.25
_chemical_melting_point           ?
_chemical_oxdiff_formula          'C13 H14 F1 N1 O6'
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'
 'N' 'N' 0.0061 0.0033 '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       'triclinic'
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x, -y, -z'

_cell_length_a                    7.6353(11)
_cell_length_b                    8.0212(17)
_cell_length_c                    12.559(3)
_cell_angle_alpha                 88.846(19)
_cell_angle_beta                  76.201(17)
_cell_angle_gamma                 66.218(17)
_cell_volume                      681.0(2)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     718
_cell_measurement_temperature     120
_cell_measurement_theta_max       32.4547
_cell_measurement_theta_min       2.7796
_exptl_absorpt_coefficient_mu     0.125
_exptl_absorpt_correction_T_max   0.994
_exptl_absorpt_correction_T_min   0.969
_exptl_absorpt_correction_type    analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_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     1.459
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        plate
_exptl_crystal_F_000              312
_exptl_crystal_size_max           0.33
_exptl_crystal_size_mid           0.2277
_exptl_crystal_size_min           0.0459
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents   0.0675
_diffrn_reflns_av_unetI/netI      0.1136
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_number             5758
_diffrn_reflns_theta_full         28.00
_diffrn_reflns_theta_max          28.00
_diffrn_reflns_theta_min          2.79
_diffrn_ambient_temperature       120
_diffrn_detector                  CCD
_diffrn_detector_area_resol_mean  16.1511
_diffrn_detector_type             Sapphire3
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9952
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -83.00  -34.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429 -179.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429   38.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega  -91.00   31.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429    0.0000    0.0000 122

#__ type_ start__ end____ width___ exp.time_
  4 omega   27.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -130.0000 -148.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega   61.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  179.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   62.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  179.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -130.0000   31.0000 57
;
_diffrn_measurement_device        '3-circle diffractometer'
_diffrn_measurement_device_type   'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method        ω-scan
_diffrn_orient_matrix_UB_11       -0.0282942000
_diffrn_orient_matrix_UB_12       -0.0700124000
_diffrn_orient_matrix_UB_13       0.0222959000
_diffrn_orient_matrix_UB_21       0.0119822000
_diffrn_orient_matrix_UB_22       -0.0351533000
_diffrn_orient_matrix_UB_23       -0.0538796000
_diffrn_orient_matrix_UB_31       0.1002970000
_diffrn_orient_matrix_UB_32       -0.0571800000
_diffrn_orient_matrix_UB_33       -0.0026464000
_diffrn_radiation_collimation     monochromator
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength      0.7107
_diffrn_radiation_xray_symbol     Mo
_diffrn_source                    'Enhance (Mo) X-ray Source'
_diffrn_source_type               'sealed tube'
_diffrn_standards_decay_%         ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_number          ?
_reflns_number_gt                 1811
_reflns_number_total              3284
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      30.44
_reflns_threshold_expression      >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max          0.311
_refine_diff_density_min          -0.360
_refine_diff_density_rms          0.078
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.014
_refine_ls_hydrogen_treatment     refall
_refine_ls_matrix_type            full
_refine_ls_number_parameters      246
_refine_ls_number_reflns          3284
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1339
_refine_ls_R_factor_gt            0.0733
_refine_ls_restrained_S_all       1.014
_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)+(0.0660P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1489
_refine_ls_wR_factor_ref          0.1932
_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. 
;
_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_symmetry_multiplicity
  _atom_site_calc_flag
  _atom_site_refinement_flags
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 F1 F 0.3019(2) 0.2055(2) 0.25418(16) 0.0340(5) Uani 1 1 d . . .
 O1 O 0.0971(3) 0.4935(3) 0.1558(2) 0.0407(6) Uani 1 1 d . . .
 O2 O 0.3075(5) 0.4789(4) 0.0043(3) 0.0736(10) Uani 1 1 d . . .
 O3 O 0.3403(3) -0.1246(3) 0.3130(2) 0.0397(6) Uani 1 1 d . . .
 O4 O 0.0143(3) -0.0382(3) 0.32825(18) 0.0302(5) Uani 1 1 d . . .
 O5 O -0.0689(3) 0.3865(3) 0.37737(19) 0.0330(6) Uani 1 1 d . . .
 O6 O -0.1800(3) 0.3146(3) 0.24137(17) 0.0264(5) Uani 1 1 d . . .
 N1 N 0.2077(4) 0.4148(4) 0.0685(3) 0.0382(7) Uani 1 1 d . . .
 C1 C 0.1949(4) 0.1126(4) 0.1130(2) 0.0220(6) Uani 1 1 d . . .
 C2 C 0.2228(4) 0.2327(4) 0.0351(3) 0.0287(7) Uani 1 1 d . . .
 C3 C 0.2625(4) 0.1921(5) -0.0766(3) 0.0354(8) Uani 1 1 d . . .
 C4 C 0.2742(4) 0.0255(5) -0.1150(3) 0.0322(8) Uani 1 1 d . . .
 C5 C 0.2513(4) -0.0972(5) -0.0407(3) 0.0301(8) Uani 1 1 d . . .
 C6 C 0.2145(4) -0.0564(4) 0.0711(3) 0.0253(7) Uani 1 1 d . . .
 C7 C 0.1583(4) 0.1516(4) 0.2347(3) 0.0253(7) Uani 1 1 d . . .
 C8 C 0.1860(5) -0.0221(4) 0.2970(3) 0.0279(7) Uani 1 1 d . . .
 C9 C 0.0160(6) -0.1981(5) 0.3873(3) 0.0358(8) Uani 1 1 d . . .
 C10 C -0.1941(6) -0.1731(6) 0.4309(4) 0.0427(9) Uani 1 1 d . . .
 C11 C -0.0429(4) 0.3024(4) 0.2936(3) 0.0256(7) Uani 1 1 d . . .
 C12 C -0.3832(5) 0.4406(5) 0.2971(3) 0.0329(8) Uani 1 1 d . . .
 C13 C -0.4752(5) 0.3526(5) 0.3870(3) 0.0330(8) Uani 1 1 d . . .
 H3 H 0.282(5) 0.283(6) -0.131(3) 0.052(11) Uiso 1 1 d . . .
 H4 H 0.297(4) 0.006(4) -0.194(3) 0.023(8) Uiso 1 1 d . . .
 H5 H 0.273(5) -0.220(5) -0.064(3) 0.036(10) Uiso 1 1 d . . .
 H6 H 0.201(5) -0.148(5) 0.122(3) 0.035(9) Uiso 1 1 d . . .
 H9A H 0.094(5) -0.221(5) 0.445(3) 0.036(9) Uiso 1 1 d . . .
 H9B H 0.103(5) -0.310(5) 0.327(3) 0.040(10) Uiso 1 1 d . . .
 H10A H -0.266(5) -0.162(5) 0.371(3) 0.052(12) Uiso 1 1 d . . .
 H10B H -0.287(6) -0.062(6) 0.483(3) 0.067(13) Uiso 1 1 d . . .
 H10C H -0.183(6) -0.289(7) 0.472(4) 0.076(14) Uiso 1 1 d . . .
 H12A H -0.440(4) 0.463(4) 0.240(3) 0.027(9) Uiso 1 1 d . . .
 H12B H -0.378(4) 0.553(5) 0.322(3) 0.032(9) Uiso 1 1 d . . .
 H13A H -0.624(6) 0.432(5) 0.420(3) 0.055(11) Uiso 1 1 d . . .
 H13B H -0.404(6) 0.308(6) 0.443(3) 0.066(13) Uiso 1 1 d . . .
 H13C H -0.469(6) 0.232(6) 0.361(3) 0.066(13) Uiso 1 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 0.0237(9) 0.0354(11) 0.0516(13) -0.0071(9) -0.0158(8) -0.0170(8)
 O1 0.0429(14) 0.0290(13) 0.0562(18) -0.0027(12) -0.0091(12) -0.0222(11)
 O2 0.092(2) 0.0486(18) 0.087(3) 0.0082(17) 0.0106(18) -0.0543(17)
 O3 0.0348(13) 0.0327(14) 0.0486(16) 0.0007(12) -0.0162(11) -0.0076(10)
 O4 0.0335(12) 0.0232(11) 0.0361(14) 0.0037(10) -0.0098(9) -0.0134(9)
 O5 0.0349(12) 0.0300(13) 0.0372(14) -0.0077(11) -0.0094(10) -0.0160(10)
 O6 0.0207(10) 0.0254(11) 0.0335(13) -0.0049(10) -0.0097(9) -0.0079(8)
 N1 0.0355(16) 0.0308(16) 0.055(2) 0.0069(15) -0.0091(14) -0.0215(13)
 C1 0.0211(14) 0.0229(15) 0.0293(17) -0.0004(13) -0.0100(11) -0.0140(11)
 C2 0.0212(15) 0.0270(17) 0.041(2) 0.0008(14) -0.0082(13) -0.0126(12)
 C3 0.0256(17) 0.041(2) 0.040(2) 0.0097(17) -0.0071(14) -0.0145(15)
 C4 0.0219(16) 0.041(2) 0.031(2) -0.0038(16) -0.0040(13) -0.0113(14)
 C5 0.0253(16) 0.0333(19) 0.034(2) -0.0091(16) -0.0061(13) -0.0149(14)
 C6 0.0226(15) 0.0240(16) 0.0327(19) -0.0035(14) -0.0046(12) -0.0141(12)
 C7 0.0213(14) 0.0259(16) 0.0374(19) -0.0048(14) -0.0130(12) -0.0151(12)
 C8 0.0308(17) 0.0240(16) 0.0290(18) -0.0029(13) -0.0113(13) -0.0090(13)
 C9 0.054(2) 0.0216(17) 0.034(2) 0.0022(15) -0.0088(16) -0.0184(15)
 C10 0.053(2) 0.036(2) 0.049(3) 0.006(2) -0.0128(19) -0.0289(19)
 C11 0.0276(16) 0.0212(15) 0.0326(18) -0.0028(14) -0.0095(13) -0.0131(12)
 C12 0.0262(17) 0.0293(19) 0.041(2) -0.0048(16) -0.0117(15) -0.0074(14)
 C13 0.0232(17) 0.0317(19) 0.045(2) -0.0097(17) -0.0063(14) -0.0126(14)

_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 C7 1.401(3) . ?
 O1 N1 1.212(4) . ?
 O2 N1 1.225(4) . ?
 O3 C8 1.196(4) . ?
 O4 C8 1.334(4) . ?
 O4 C9 1.465(4) . ?
 O5 C11 1.193(3) . ?
 O6 C11 1.334(3) . ?
 O6 C12 1.471(4) . ?
 N1 C2 1.479(4) . ?
 C1 C2 1.400(4) . ?
 C1 C6 1.402(4) . ?
 C1 C7 1.503(4) . ?
 C2 C3 1.379(5) . ?
 C3 C4 1.391(5) . ?
 C3 H3 1.02(4) . ?
 C4 C5 1.376(5) . ?
 C4 H4 0.96(3) . ?
 C5 C6 1.383(5) . ?
 C5 H5 0.97(4) . ?
 C6 H6 0.98(4) . ?
 C7 C8 1.547(4) . ?
 C7 C11 1.538(4) . ?
 C9 C10 1.496(5) . ?
 C9 H9A 1.01(3) . ?
 C9 H9B 1.06(3) . ?
 C10 H10A 1.01(4) . ?
 C10 H10B 1.00(4) . ?
 C10 H10C 1.04(5) . ?
 C12 C13 1.502(5) . ?
 C12 H12A 0.90(3) . ?
 C12 H12B 0.98(3) . ?
 C13 H13A 1.03(4) . ?
 C13 H13B 0.97(4) . ?
 C13 H13C 1.00(5) . ?

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
 C8 O4 C9 116.6(2) . . ?
 C11 O6 C12 115.1(2) . . ?
 O1 N1 O2 123.6(3) . . ?
 O1 N1 C2 119.2(3) . . ?
 O2 N1 C2 117.2(3) . . ?
 C2 C1 C6 116.1(3) . . ?
 C2 C1 C7 123.8(3) . . ?
 C6 C1 C7 120.0(3) . . ?
 C1 C2 N1 121.5(3) . . ?
 C3 C2 N1 115.6(3) . . ?
 C3 C2 C1 123.0(3) . . ?
 C2 C3 C4 119.3(3) . . ?
 C2 C3 H3 121(2) . . ?
 C4 C3 H3 120(2) . . ?
 C3 C4 H4 116(2) . . ?
 C5 C4 C3 119.2(3) . . ?
 C5 C4 H4 125(2) . . ?
 C4 C5 C6 121.1(3) . . ?
 C4 C5 H5 122(2) . . ?
 C6 C5 H5 117(2) . . ?
 C1 C6 H6 120(2) . . ?
 C5 C6 C1 121.3(3) . . ?
 C5 C6 H6 119(2) . . ?
 F1 C7 C1 109.1(2) . . ?
 F1 C7 C8 104.5(2) . . ?
 F1 C7 C11 106.1(2) . . ?
 C1 C7 C8 112.0(2) . . ?
 C1 C7 C11 116.7(2) . . ?
 C11 C7 C8 107.5(2) . . ?
 O3 C8 O4 126.4(3) . . ?
 O3 C8 C7 123.9(3) . . ?
 O4 C8 C7 109.8(2) . . ?
 O4 C9 C10 107.7(3) . . ?
 O4 C9 H9A 112(2) . . ?
 O4 C9 H9B 103(2) . . ?
 C10 C9 H9A 114(2) . . ?
 C10 C9 H9B 114.8(19) . . ?
 H9A C9 H9B 104(3) . . ?
 C9 C10 H10A 113(2) . . ?
 C9 C10 H10B 118(3) . . ?
 C9 C10 H10C 104(2) . . ?
 H10A C10 H10B 102(3) . . ?
 H10A C10 H10C 111(3) . . ?
 H10B C10 H10C 109(3) . . ?
 O5 C11 O6 126.6(3) . . ?
 O5 C11 C7 123.0(3) . . ?
 O6 C11 C7 110.3(2) . . ?
 O6 C12 C13 111.2(3) . . ?
 O6 C12 H12A 101(2) . . ?
 O6 C12 H12B 107.4(18) . . ?
 C13 C12 H12A 113(2) . . ?
 C13 C12 H12B 114(2) . . ?
 H12A C12 H12B 109(3) . . ?
 C12 C13 H13A 112(2) . . ?
 C12 C13 H13B 115(3) . . ?
 C12 C13 H13C 113(2) . . ?
 H13A C13 H13B 112(3) . . ?
 H13A C13 H13C 105(3) . . ?
 H13B C13 H13C 97(3) . . ?

loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 0 0 1 0.0229 0.0005 -0.0022 1.0002 0.0224 -0.0538 -0.0025
 0 0 -1 0.0229 -0.0005 0.0022 -1.0002 -0.0224 0.0538 0.0025
 1 0 0 0.1042 0.9984 0.0036 -0.0132 -0.0288 0.0125 0.1000
 -1 0 0 0.1042 -0.9984 -0.0036 0.0132 0.0288 -0.0125 -0.1000
 5 11 2 0.1604 4.9954 10.9877 2.0593 -0.8647 -0.4374 -0.1327
 -5 -11 -2 0.1504 -4.9954 -10.9877 -2.0593 0.8647 0.4374 0.1327
 6 -6 2 0.1214 5.9899 -5.9684 1.8534 0.2897 0.1817 0.9371
 -8 -10 -4 0.1558 -7.9913 -9.9966 -4.0089 0.8366 0.4717 -0.2193

#==END
data_6a_12srv157
_audit_creation_date              2012-08-23
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.08.15 svn.r2450, GUI svn.r4314)
;

_chemical_name_common             ?
_chemical_name_systematic
;
Methyl 2-fluoro-2-(2-nitrophenyl)acetate
;
_chemical_formula_moiety          'C9 H8 F N O4'
_chemical_formula_sum             'C9 H8 F N O4'
_chemical_formula_weight          213.16
_chemical_absolute_configuration  unk
_chemical_melting_point           ?
_chemical_oxdiff_formula          'C9 H8 F1 N1 O4'
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'
 'N' 'N' 0.0061 0.0033 '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       'orthorhombic'
_space_group_IT_number            33
_space_group_name_H-M_alt         'P n a 21'
_space_group_name_Hall            'P 2c -2n'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x, -y, z+1/2'
 3 '-x+1/2, y+1/2, z+1/2'
 4 'x+1/2, -y+1/2, z'

_cell_length_a                    7.2946(7)
_cell_length_b                    16.473(2)
_cell_length_c                    7.7761(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      934.4(2)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     757
_cell_measurement_temperature     120
_cell_measurement_theta_max       32.3602
_cell_measurement_theta_min       2.6140
_exptl_absorpt_coefficient_mu     0.133
_exptl_absorpt_correction_T_max   0.999
_exptl_absorpt_correction_T_min   0.989
_exptl_absorpt_correction_type    analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_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     1.515
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        plate
_exptl_crystal_F_000              440
_exptl_crystal_size_max           0.4553
_exptl_crystal_size_mid           0.1647
_exptl_crystal_size_min           0.0329
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents   0.0839
_diffrn_reflns_av_unetI/netI      0.0843
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_number             4548
_diffrn_reflns_theta_full         27.99
_diffrn_reflns_theta_max          27.99
_diffrn_reflns_theta_min          2.90
_diffrn_ambient_temperature       120
_diffrn_detector                  CCD
_diffrn_detector_area_resol_mean  16.1511
_diffrn_detector_type             Sapphire3
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9881
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00  -71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -38.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -58.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429   19.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega  -72.00  -25.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  124.0000  -73.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -99.00  -19.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -19.0000  -60.0000 80
;
_diffrn_measurement_device        '3-circle diffractometer'
_diffrn_measurement_device_type   'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method        ω-scan
_diffrn_orient_matrix_UB_11       -0.0191723000
_diffrn_orient_matrix_UB_12       -0.0169070000
_diffrn_orient_matrix_UB_13       0.0818825000
_diffrn_orient_matrix_UB_21       0.0017476000
_diffrn_orient_matrix_UB_22       0.0393599000
_diffrn_orient_matrix_UB_23       0.0370129000
_diffrn_orient_matrix_UB_31       -0.0953117000
_diffrn_orient_matrix_UB_32       0.0041977000
_diffrn_orient_matrix_UB_33       -0.0158623000
_diffrn_radiation_collimation     monochromator
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength      0.7107
_diffrn_radiation_xray_symbol     Mo
_diffrn_source                    'Enhance (Mo) X-ray Source'
_diffrn_source_type               'sealed tube'
_diffrn_standards_decay_%         ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_number          ?
_reflns_number_gt                 874
_reflns_number_total              1207
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      30.44
_reflns_threshold_expression      >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max          0.341
_refine_diff_density_min          -0.299
_refine_diff_density_rms          0.072
_refine_ls_abs_structure_details  'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0(2)
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.096
_refine_ls_hydrogen_treatment     refall
_refine_ls_matrix_type            full
_refine_ls_number_parameters      168
_refine_ls_number_reflns          1207
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0860
_refine_ls_R_factor_gt            0.0534
_refine_ls_restrained_S_all       1.095
_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)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1065
_refine_ls_wR_factor_ref          0.1266
_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. 
;
_atom_sites_solution_hydrogens    difmap
_atom_sites_solution_primary      iterative
_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_symmetry_multiplicity
  _atom_site_calc_flag
  _atom_site_refinement_flags
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 F1 F -0.0948(3) 0.54214(16) 0.5006(4) 0.0304(7) Uani 1 1 d . . .
 O1 O 0.1291(4) 0.6194(2) 0.2703(5) 0.0337(8) Uani 1 1 d . . .
 O2 O -0.0611(5) 0.7204(2) 0.2400(5) 0.0467(10) Uani 1 1 d . . .
 O3 O 0.2015(4) 0.45331(19) 0.4317(4) 0.0304(8) Uani 1 1 d . . .
 O4 O 0.3607(4) 0.5140(2) 0.6415(5) 0.0319(8) Uani 1 1 d . . .
 N1 N 0.0447(5) 0.6783(2) 0.3274(5) 0.0295(9) Uani 1 1 d . . .
 C1 C 0.0922(5) 0.6428(3) 0.6353(6) 0.0211(9) Uani 1 1 d . . .
 C2 C 0.0776(6) 0.7012(3) 0.5063(6) 0.0244(10) Uani 1 1 d . . .
 C3 C 0.0926(6) 0.7840(3) 0.5406(8) 0.0302(12) Uani 1 1 d . . .
 C4 C 0.1348(6) 0.8089(3) 0.7053(7) 0.0310(11) Uani 1 1 d . . .
 C5 C 0.1567(6) 0.7518(3) 0.8337(8) 0.0321(11) Uani 1 1 d . . .
 C6 C 0.1320(6) 0.6695(3) 0.8007(7) 0.0277(11) Uani 1 1 d . . .
 C7 C 0.0556(6) 0.5538(3) 0.6101(6) 0.0223(10) Uani 1 1 d . . .
 C8 C 0.2121(6) 0.5017(3) 0.5461(6) 0.0223(9) Uani 1 1 d . . .
 C9 C 0.5143(7) 0.4604(3) 0.6032(8) 0.0353(13) Uani 1 1 d . . .
 H3 H 0.075(8) 0.815(3) 0.438(9) 0.053(18) Uiso 1 1 d . . .
 H4 H 0.133(7) 0.865(4) 0.749(8) 0.049(16) Uiso 1 1 d . . .
 H6 H 0.130(6) 0.632(3) 0.900(8) 0.038(16) Uiso 1 1 d . . .
 H7 H 0.018(6) 0.533(3) 0.718(7) 0.021(13) Uiso 1 1 d . . .
 H9A H 0.546(7) 0.469(3) 0.471(8) 0.040(15) Uiso 1 1 d . . .
 H9B H 0.490(10) 0.394(4) 0.623(11) 0.08(2) Uiso 1 1 d . . .
 H9C H 0.608(7) 0.476(3) 0.689(8) 0.034(15) Uiso 1 1 d . . .
 H5 H 0.175(5) 0.770(3) 0.954(7) 0.017(11) Uiso 1 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 0.0192(12) 0.0336(15) 0.0384(17) -0.0050(13) -0.0037(12) -0.0008(11)
 O1 0.0389(18) 0.0307(18) 0.031(2) -0.0056(15) 0.0087(17) 0.0059(14)
 O2 0.058(2) 0.046(2) 0.036(2) 0.005(2) -0.014(2) 0.0205(19)
 O3 0.0268(16) 0.0336(18) 0.031(2) -0.0093(17) -0.0024(16) 0.0048(13)
 O4 0.0197(15) 0.0363(18) 0.040(2) -0.0085(17) -0.0096(17) 0.0064(13)
 N1 0.034(2) 0.031(2) 0.023(2) 0.0011(19) 0.0024(19) -0.0012(17)
 C1 0.0105(19) 0.024(2) 0.029(3) -0.0048(19) 0.0015(18) 0.0019(16)
 C2 0.018(2) 0.031(2) 0.024(2) -0.004(2) 0.0023(19) 0.0006(17)
 C3 0.022(2) 0.029(2) 0.039(3) -0.001(3) 0.008(2) 0.000(2)
 C4 0.025(2) 0.028(2) 0.040(3) -0.009(2) 0.003(2) 0.0004(19)
 C5 0.024(2) 0.042(3) 0.030(3) -0.016(2) 0.002(2) -0.0006(19)
 C6 0.020(2) 0.035(3) 0.028(3) -0.005(2) 0.003(2) -0.0005(18)
 C7 0.018(2) 0.028(2) 0.021(3) -0.001(2) -0.0025(19) -0.0008(17)
 C8 0.020(2) 0.026(2) 0.021(2) -0.002(2) -0.0034(19) -0.0003(17)
 C9 0.021(2) 0.040(3) 0.044(4) -0.009(3) -0.001(2) 0.009(2)

_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 C7 1.401(5) . ?
 O1 N1 1.233(5) . ?
 O2 N1 1.240(5) . ?
 O3 C8 1.197(5) . ?
 O4 C8 1.329(5) . ?
 O4 C9 1.457(6) . ?
 N1 C2 1.461(6) . ?
 C1 C2 1.394(7) . ?
 C1 C6 1.390(7) . ?
 C1 C7 1.503(6) . ?
 C2 C3 1.393(6) . ?
 C3 C4 1.380(8) . ?
 C3 H3 0.95(7) . ?
 C4 C5 1.382(8) . ?
 C4 H4 0.98(6) . ?
 C5 C6 1.391(7) . ?
 C5 H5 0.99(5) . ?
 C6 H6 0.99(5) . ?
 C7 C8 1.513(6) . ?
 C7 H7 0.95(5) . ?
 C9 H9A 1.06(6) . ?
 C9 H9B 1.12(7) . ?
 C9 H9C 0.99(6) . ?

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
 C8 O4 C9 114.9(4) . . ?
 O1 N1 O2 123.6(4) . . ?
 O1 N1 C2 117.6(4) . . ?
 O2 N1 C2 118.7(4) . . ?
 C2 C1 C7 124.5(4) . . ?
 C6 C1 C2 117.6(4) . . ?
 C6 C1 C7 117.8(4) . . ?
 C1 C2 N1 121.3(4) . . ?
 C3 C2 N1 116.6(4) . . ?
 C3 C2 C1 122.1(5) . . ?
 C2 C3 H3 111(4) . . ?
 C4 C3 C2 119.1(5) . . ?
 C4 C3 H3 130(4) . . ?
 C3 C4 C5 119.6(5) . . ?
 C3 C4 H4 127(4) . . ?
 C5 C4 H4 113(4) . . ?
 C4 C5 C6 121.0(5) . . ?
 C4 C5 H5 119(3) . . ?
 C6 C5 H5 119(3) . . ?
 C1 C6 C5 120.4(5) . . ?
 C1 C6 H6 121(3) . . ?
 C5 C6 H6 118(3) . . ?
 F1 C7 C1 110.6(3) . . ?
 F1 C7 C8 108.3(4) . . ?
 F1 C7 H7 106(3) . . ?
 C1 C7 C8 117.5(3) . . ?
 C1 C7 H7 106(3) . . ?
 C8 C7 H7 108(3) . . ?
 O3 C8 O4 124.7(4) . . ?
 O3 C8 C7 125.0(4) . . ?
 O4 C8 C7 110.2(4) . . ?
 O4 C9 H9A 107(3) . . ?
 O4 C9 H9B 116(4) . . ?
 O4 C9 H9C 103(3) . . ?
 H9A C9 H9B 107(5) . . ?
 H9A C9 H9C 118(4) . . ?
 H9B C9 H9C 106(5) . . ?

loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 0 0 -1 0.2275 -0.0005 0.0063 -1.0005 -0.0820 -0.0368 0.0159
 0 0 1 0.2275 0.0005 -0.0063 1.0005 0.0820 0.0368 -0.0159
 -1 0 0 0.0824 -0.9995 -0.0010 -0.0001 0.0192 -0.0018 0.0953
 1 0 0 0.0824 0.9995 0.0010 0.0001 -0.0192 0.0018 -0.0953
 0 1 0 0.0165 -0.0004 0.9993 0.0002 -0.0169 0.0393 0.0042
 0 -1 0 0.0165 0.0004 -0.9993 -0.0002 0.0169 -0.0393 -0.0042

#==END

data_7_12srv159
_audit_creation_date              2012-08-23
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.08.15 svn.r2450, GUI svn.r4314)
;

_chemical_name_common             ?
_chemical_name_systematic         2-fluoromethyl-3-nitropyridine
_chemical_formula_moiety          'C6 H5 F N2 O2'
_chemical_formula_sum             'C6 H5 F N2 O2'
_chemical_formula_weight          156.12
_chemical_melting_point           ?
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'
 'N' 'N' 0.0061 0.0033 '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                    5.6568(3)
_cell_length_b                    15.4823(9)
_cell_length_c                    7.1654(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.767(2)
_cell_angle_gamma                 90.00
_cell_volume                      623.18(6)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     3154
_cell_measurement_temperature     120
_cell_measurement_theta_max       30.89
_cell_measurement_theta_min       2.63
_exptl_absorpt_coefficient_mu     0.146
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_correction_T_min   0.2991
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0452 before and 0.0319 after correction.
The Ratio of minimum to maximum transmission is 0.2991.
The λ/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     1.664
_exptl_crystal_density_meas       .
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        irregular
_exptl_crystal_F_000              320
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.19
_exptl_crystal_size_min           0.12
_exptl_special_details
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (5 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents   0.0376
_diffrn_reflns_av_unetI/netI      0.0315
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_number             10239
_diffrn_reflns_theta_full         29.50
_diffrn_reflns_theta_max          29.50
_diffrn_reflns_theta_min          2.63
_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   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_xray_symbol     K-L~3~
_diffrn_source                    'sealed X-ray tube'
_diffrn_source_current            5.0
_diffrn_source_power              0.1
_diffrn_source_target             Mo
_diffrn_source_type               'sealed X-ray tube'
_diffrn_source_voltage            20.0
_diffrn_standards_decay_%         ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_number          ?
_reflns_number_gt                 1374
_reflns_number_total              1735
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max          0.459
_refine_diff_density_min          -0.318
_refine_diff_density_rms          0.069
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.036
_refine_ls_hydrogen_treatment     refall
_refine_ls_matrix_type            full
_refine_ls_number_parameters      120
_refine_ls_number_reflns          1735
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0587
_refine_ls_R_factor_gt            0.0462
_refine_ls_restrained_S_all       1.036
_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)+(0.0750P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1217
_refine_ls_wR_factor_ref          0.1347
_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. 
;
_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_symmetry_multiplicity
  _atom_site_calc_flag
  _atom_site_refinement_flags
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 F1 F 0.44149(15) 0.40173(5) 0.07319(14) 0.0289(3) Uani 1 1 d . . .
 O1 O 1.08128(19) 0.48458(6) 0.30370(17) 0.0297(3) Uani 1 1 d . . .
 O2 O 1.32849(19) 0.41123(7) 0.49608(16) 0.0279(3) Uani 1 1 d . . .
 N1 N 0.6812(2) 0.26565(7) 0.17431(16) 0.0185(3) Uani 1 1 d . . .
 N2 N 1.1544(2) 0.41623(7) 0.37717(17) 0.0202(3) Uani 1 1 d . . .
 C1 C 0.6704(2) 0.42164(9) 0.1554(2) 0.0206(3) Uani 1 1 d . . .
 C2 C 0.7981(2) 0.33936(8) 0.21971(17) 0.0162(3) Uani 1 1 d . . .
 C3 C 1.0266(2) 0.33677(8) 0.32031(18) 0.0165(3) Uani 1 1 d . . .
 C4 C 1.1387(2) 0.25926(8) 0.37126(18) 0.0174(3) Uani 1 1 d . . .
 C5 C 1.0159(2) 0.18412(8) 0.31917(19) 0.0186(3) Uani 1 1 d . . .
 C6 C 0.7888(2) 0.19071(8) 0.22391(18) 0.0193(3) Uani 1 1 d . . .
 H1A H 0.751(3) 0.4520(11) 0.063(2) 0.017(4) Uiso 1 1 d . . .
 H1B H 0.653(3) 0.4601(12) 0.259(3) 0.026(4) Uiso 1 1 d . . .
 H4 H 1.296(4) 0.2577(12) 0.439(3) 0.031(5) Uiso 1 1 d . . .
 H5 H 1.088(3) 0.1268(12) 0.345(3) 0.024(4) Uiso 1 1 d . . .
 H6 H 0.696(3) 0.1365(12) 0.187(3) 0.025(4) Uiso 1 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 0.0202(4) 0.0238(4) 0.0388(5) 0.0001(3) -0.0124(4) 0.0025(3)
 O1 0.0270(6) 0.0165(5) 0.0434(7) 0.0033(4) -0.0055(5) -0.0004(4)
 O2 0.0221(5) 0.0251(5) 0.0332(6) -0.0024(4) -0.0106(4) -0.0033(4)
 N1 0.0172(5) 0.0179(5) 0.0198(5) -0.0001(4) -0.0008(4) -0.0011(4)
 N2 0.0169(5) 0.0173(5) 0.0257(6) -0.0009(4) -0.0014(4) -0.0008(4)
 C1 0.0175(6) 0.0180(6) 0.0247(7) 0.0010(5) -0.0042(5) 0.0007(5)
 C2 0.0155(6) 0.0169(6) 0.0157(6) 0.0005(4) -0.0005(4) 0.0001(4)
 C3 0.0163(6) 0.0150(6) 0.0174(6) -0.0008(4) -0.0009(4) -0.0017(4)
 C4 0.0161(6) 0.0179(6) 0.0177(6) 0.0007(4) -0.0004(4) 0.0007(4)
 C5 0.0201(6) 0.0162(6) 0.0190(6) 0.0003(5) -0.0005(5) 0.0018(5)
 C6 0.0202(6) 0.0174(6) 0.0194(6) 0.0002(5) -0.0018(5) -0.0021(5)

_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 1.3928(15) . ?
 O1 N2 1.2315(15) . ?
 O2 N2 1.2266(16) . ?
 N1 C2 1.3396(16) . ?
 N1 C6 1.3384(17) . ?
 N2 C3 1.4603(16) . ?
 C1 C2 1.5093(17) . ?
 C1 H1A 0.970(17) . ?
 C1 H1B 0.968(19) . ?
 C2 C3 1.4043(17) . ?
 C3 C4 1.3859(17) . ?
 C4 C5 1.3835(18) . ?
 C4 H4 0.96(2) . ?
 C5 C6 1.3860(18) . ?
 C5 H5 0.986(19) . ?
 C6 H6 1.008(19) . ?

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
 C6 N1 C2 118.57(11) . . ?
 O1 N2 C3 118.32(11) . . ?
 O2 N2 O1 123.57(11) . . ?
 O2 N2 C3 118.11(11) . . ?
 F1 C1 C2 109.26(11) . . ?
 F1 C1 H1A 108.0(10) . . ?
 F1 C1 H1B 106.7(12) . . ?
 C2 C1 H1A 111.7(10) . . ?
 C2 C1 H1B 111.9(11) . . ?
 H1A C1 H1B 109.0(15) . . ?
 N1 C2 C1 116.12(11) . . ?
 N1 C2 C3 119.89(11) . . ?
 C3 C2 C1 123.98(11) . . ?
 C2 C3 N2 120.97(11) . . ?
 C4 C3 N2 117.38(11) . . ?
 C4 C3 C2 121.64(11) . . ?
 C3 C4 H4 121.5(11) . . ?
 C5 C4 C3 117.23(12) . . ?
 C5 C4 H4 121.3(11) . . ?
 C4 C5 C6 118.53(12) . . ?
 C4 C5 H5 121.5(11) . . ?
 C6 C5 H5 120.0(11) . . ?
 N1 C6 C5 124.09(12) . . ?
 N1 C6 H6 116.5(11) . . ?
 C5 C6 H6 119.4(11) . . ?
