# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_6273

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 F N2 O5'
_chemical_formula_weight         268.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8225(6)
_cell_length_b                   8.6115(9)
_cell_length_c                   10.7203(12)
_cell_angle_alpha                67.906(10)
_cell_angle_beta                 86.057(8)
_cell_angle_gamma                78.308(8)
_cell_volume                     571.46(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    1192
_cell_measurement_theta_min      4.4330
_cell_measurement_theta_max      64.7560

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7989
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3293
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.45
_diffrn_reflns_theta_max         62.94
_reflns_number_total             1808
_reflns_number_gt                1387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0687P)²+0.0355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1808
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
N1 N 0.1213(3) 0.2884(2) 0.62119(18) 0.0225(4) Uani 1 1 d . . .
F1 F 0.3539(2) -0.12438(15) 0.84625(14) 0.0383(4) Uani 1 1 d . . .
O2 O 0.2544(2) 0.51082(18) 0.47665(15) 0.0273(4) Uani 1 1 d . . .
O1 O -0.0215(2) 0.07212(19) 0.76358(16) 0.0313(4) Uani 1 1 d . . .
N2 N 0.4630(3) 0.2682(2) 0.60408(19) 0.0256(5) Uani 1 1 d . . .
C4 C 0.3332(3) 0.0356(3) 0.7537(2) 0.0264(5) Uani 1 1 d . . .
C2 C 0.2784(3) 0.3638(3) 0.5626(2) 0.0224(5) Uani 1 1 d . . .
C3 C 0.4906(3) 0.1053(3) 0.6993(2) 0.0272(5) Uani 1 1 d . . .
H3A H 0.6194 0.0439 0.7256 0.033 Uiso 1 1 calc R . .
C1 C 0.1315(3) 0.1261(3) 0.7180(2) 0.0240(5) Uani 1 1 d . . .
H2 H 0.567(4) 0.326(3) 0.569(3) 0.053(8) Uiso 1 1 d . . .
H1 H -0.002(4) 0.355(3) 0.593(3) 0.042(7) Uiso 1 1 d . . .
O3 O -0.2224(2) -0.1269(2) 0.95668(17) 0.0398(5) Uani 1 1 d . . .
H3 H -0.1214 -0.0924 0.9206 0.060 Uiso 1 1 calc R . .
C8 C -0.0860(3) -0.6102(3) 1.2503(2) 0.0259(5) Uani 1 1 d . . .
O5 O -0.1848(2) -0.84788(19) 1.42293(16) 0.0342(4) Uani 1 1 d . . .
O4 O 0.1419(2) -0.84906(19) 1.38619(16) 0.0323(4) Uani 1 1 d . . .
H4 H 0.1502 -0.9445 1.4450 0.049 Uiso 1 1 calc R . .
C5 C -0.1700(3) -0.2862(3) 1.0504(2) 0.0290(6) Uani 1 1 d . . .
C11 C -0.0476(3) -0.7781(3) 1.3589(2) 0.0268(5) Uani 1 1 d . . .
C10 C -0.3257(4) -0.3677(3) 1.1136(2) 0.0311(6) Uani 1 1 d . . .
H10 H -0.4577 -0.3142 1.0893 0.037 Uiso 1 1 calc R . .
C7 C 0.0689(3) -0.5268(3) 1.1847(2) 0.0281(5) Uani 1 1 d . . .
H7 H 0.2012 -0.5803 1.2081 0.034 Uiso 1 1 calc R . .
C9 C -0.2836(3) -0.5284(3) 1.2128(2) 0.0294(6) Uani 1 1 d . . .
H9 H -0.3880 -0.5830 1.2552 0.035 Uiso 1 1 calc R . .
C6 C 0.0277(3) -0.3658(3) 1.0853(2) 0.0295(6) Uani 1 1 d . . .
H6 H 0.1315 -0.3111 1.0421 0.035 Uiso 1 1 calc R . .

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
N1 0.0171(10) 0.0221(10) 0.0258(10) -0.0056(9) 0.0000(8) -0.0048(8)
F1 0.0349(8) 0.0228(7) 0.0438(9) 0.0041(6) -0.0054(6) -0.0066(6)
O2 0.0205(8) 0.0250(9) 0.0291(9) -0.0009(8) -0.0009(6) -0.0063(7)
O1 0.0250(9) 0.0298(9) 0.0355(10) -0.0053(8) 0.0009(7) -0.0111(7)
N2 0.0179(10) 0.0249(10) 0.0290(11) -0.0042(9) 0.0010(8) -0.0047(8)
C4 0.0277(13) 0.0188(11) 0.0272(12) -0.0026(10) -0.0030(10) -0.0031(10)
C2 0.0195(11) 0.0238(12) 0.0228(12) -0.0068(10) 0.0010(9) -0.0058(9)
C3 0.0228(12) 0.0231(12) 0.0302(13) -0.0046(10) -0.0011(10) -0.0017(10)
C1 0.0235(12) 0.0235(12) 0.0251(12) -0.0073(10) 0.0006(9) -0.0086(10)
O3 0.0337(10) 0.0348(10) 0.0356(10) 0.0057(8) -0.0004(8) -0.0093(8)
C8 0.0306(13) 0.0239(12) 0.0242(12) -0.0088(10) 0.0010(10) -0.0074(10)
O5 0.0325(9) 0.0280(9) 0.0345(10) -0.0042(8) 0.0046(8) -0.0052(7)
O4 0.0299(9) 0.0259(9) 0.0358(10) -0.0061(8) -0.0006(7) -0.0037(7)
C5 0.0324(13) 0.0292(13) 0.0237(12) -0.0065(11) 0.0006(10) -0.0085(10)
C11 0.0297(13) 0.0255(12) 0.0271(13) -0.0122(11) 0.0034(10) -0.0057(10)
C10 0.0280(13) 0.0328(13) 0.0281(13) -0.0061(11) -0.0011(10) -0.0059(10)
C7 0.0264(12) 0.0296(12) 0.0298(13) -0.0139(11) 0.0016(10) -0.0037(10)
C9 0.0273(13) 0.0319(13) 0.0278(13) -0.0080(11) 0.0030(10) -0.0097(10)
C6 0.0307(13) 0.0324(13) 0.0256(13) -0.0081(11) 0.0041(10) -0.0135(11)

_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
N1 C2 1.359(3) . ?
N1 C1 1.384(3) . ?
N1 H1 0.92(3) . ?
F1 C4 1.347(2) . ?
O2 C2 1.240(2) . ?
O1 C1 1.224(2) . ?
N2 C2 1.358(3) . ?
N2 C3 1.374(3) . ?
N2 H2 0.93(3) . ?
C4 C3 1.328(3) . ?
C4 C1 1.436(3) . ?
C3 H3A 0.9300 . ?
O3 C5 1.354(3) . ?
O3 H3 0.8200 . ?
C8 C9 1.397(3) . ?
C8 C7 1.398(3) . ?
C8 C11 1.462(3) . ?
O5 C11 1.240(3) . ?
O4 C11 1.314(3) . ?
O4 H4 0.8200 . ?
C5 C10 1.387(3) . ?
C5 C6 1.390(3) . ?
C10 C9 1.380(3) . ?
C10 H10 0.9300 . ?
C7 C6 1.381(3) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C6 H6 0.9300 . ?

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 N1 C1 126.64(19) . . ?
C2 N1 H1 114.8(15) . . ?
C1 N1 H1 118.5(15) . . ?
C2 N2 C3 122.42(19) . . ?
C2 N2 H2 114.1(17) . . ?
C3 N2 H2 123.2(17) . . ?
C3 C4 F1 121.8(2) . . ?
C3 C4 C1 122.2(2) . . ?
F1 C4 C1 116.01(18) . . ?
O2 C2 N2 122.15(19) . . ?
O2 C2 N1 122.03(19) . . ?
N2 C2 N1 115.83(19) . . ?
C4 C3 N2 120.0(2) . . ?
C4 C3 H3A 120.0 . . ?
N2 C3 H3A 120.0 . . ?
O1 C1 N1 120.59(19) . . ?
O1 C1 C4 126.4(2) . . ?
N1 C1 C4 112.97(18) . . ?
C5 O3 H3 109.5 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 C11 119.2(2) . . ?
C7 C8 C11 122.0(2) . . ?
C11 O4 H4 109.5 . . ?
O3 C5 C10 116.5(2) . . ?
O3 C5 C6 123.0(2) . . ?
C10 C5 C6 120.5(2) . . ?
O5 C11 O4 122.1(2) . . ?
O5 C11 C8 122.2(2) . . ?
O4 C11 C8 115.71(19) . . ?
C9 C10 C5 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?

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
C3 N2 C2 O2 180.0(2) . . . . ?
C3 N2 C2 N1 0.0(3) . . . . ?
C1 N1 C2 O2 -179.7(2) . . . . ?
C1 N1 C2 N2 0.3(3) . . . . ?
F1 C4 C3 N2 179.28(19) . . . . ?
C1 C4 C3 N2 -1.0(4) . . . . ?
C2 N2 C3 C4 0.4(3) . . . . ?
C2 N1 C1 O1 179.9(2) . . . . ?
C2 N1 C1 C4 -0.8(3) . . . . ?
C3 C4 C1 O1 -179.6(2) . . . . ?
F1 C4 C1 O1 0.2(3) . . . . ?
C3 C4 C1 N1 1.2(3) . . . . ?
F1 C4 C1 N1 -179.09(18) . . . . ?
C9 C8 C11 O5 -3.0(3) . . . . ?
C7 C8 C11 O5 175.5(2) . . . . ?
C9 C8 C11 O4 178.3(2) . . . . ?
C7 C8 C11 O4 -3.3(3) . . . . ?
O3 C5 C10 C9 -178.2(2) . . . . ?
C6 C5 C10 C9 0.6(4) . . . . ?
C9 C8 C7 C6 0.6(3) . . . . ?
C11 C8 C7 C6 -177.9(2) . . . . ?
C5 C10 C9 C8 0.0(4) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C11 C8 C9 C10 178.0(2) . . . . ?
C8 C7 C6 C5 -0.1(3) . . . . ?
O3 C5 C6 C7 178.2(2) . . . . ?
C10 C5 C6 C7 -0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.93(3) 1.94(3) 2.847(2) 164(2) 2_666
N1 H1 O2 0.92(3) 1.89(3) 2.805(2) 176(2) 2_566
O3 H3 O1 0.82 1.94 2.645(2) 144.3 .
O4 H4 O5 0.82 1.80 2.615(2) 176.1 2_538

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        62.94
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 983683'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_4224

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 F N2 O5'
_chemical_formula_weight         268.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0356(3)
_cell_length_b                   14.9022(13)
_cell_length_c                   10.2665(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.418(4)
_cell_angle_gamma                90.00
_cell_volume                     1061.90(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.02(11)
_cell_measurement_reflns_used    837
_cell_measurement_theta_min      2.9629
_cell_measurement_theta_max      65.2715

_exptl_crystal_description       colorless
_exptl_crystal_colour            needle
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  0.881
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.02(11)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3520
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.28
_diffrn_reflns_theta_max         62.95
_reflns_number_total             1715
_reflns_number_gt                1044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0958P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1690
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

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 0.1538(3) 0.52043(19) 0.10424(19) 0.0621(8) Uani 1 1 d . . .
O5 O 0.1807(4) 1.1178(3) 0.1924(2) 0.0682(10) Uani 1 1 d . . .
O1 O 0.3663(3) 0.5547(3) 0.3498(2) 0.0641(10) Uani 1 1 d . . .
O3 O 0.2066(4) 0.6952(3) 0.1496(3) 0.0733(11) Uani 1 1 d . . .
N2 N 0.2211(4) 0.3009(3) 0.2432(3) 0.0535(11) Uani 1 1 d . . .
O4 O 0.3497(4) 1.0833(3) 0.3901(2) 0.0702(11) Uani 1 1 d . . .
H4 H 0.3324 1.1366 0.4045 0.105 Uiso 1 1 calc R . .
O2 O 0.3634(3) 0.2561(3) 0.4479(2) 0.0692(10) Uani 1 1 d . . .
N1 N 0.3598(4) 0.4048(4) 0.3975(3) 0.0638(14) Uani 1 1 d . . .
C8 C 0.2467(4) 0.9639(4) 0.2453(3) 0.0592(15) Uani 1 1 d . . .
C4 C 0.2088(5) 0.4527(4) 0.1890(3) 0.0547(13) Uani 1 1 d . . .
C3 C 0.1656(5) 0.3685(4) 0.1549(3) 0.0551(13) Uani 1 1 d . . .
H3A H 0.0978 0.3554 0.0715 0.066 Uiso 1 1 calc R . .
C10 C 0.1563(5) 0.8457(5) 0.0887(4) 0.0673(16) Uani 1 1 d . . .
H10 H 0.1029 0.8269 0.0042 0.081 Uiso 1 1 calc R . .
C5 C 0.2245(5) 0.7834(5) 0.1856(4) 0.0608(15) Uani 1 1 d . . .
C1 C 0.3155(5) 0.4778(4) 0.3142(3) 0.0595(15) Uani 1 1 d . . .
C9 C 0.1687(5) 0.9355(4) 0.1194(4) 0.0615(15) Uani 1 1 d . . .
H9 H 0.1242 0.9777 0.0549 0.074 Uiso 1 1 calc R . .
C11 C 0.2540(4) 1.0615(4) 0.2724(4) 0.0630(16) Uani 1 1 d . . .
C2 C 0.3164(5) 0.3161(4) 0.3669(3) 0.0605(15) Uani 1 1 d . . .
C6 C 0.3047(5) 0.8102(4) 0.3115(3) 0.0596(15) Uani 1 1 d . . .
H6 H 0.3509 0.7679 0.3755 0.071 Uiso 1 1 calc R . .
C7 C 0.3154(5) 0.9014(4) 0.3411(4) 0.0597(15) Uani 1 1 d . . .
H7 H 0.3688 0.9203 0.4255 0.072 Uiso 1 1 calc R . .
H1 H 0.423(7) 0.417(3) 0.469(5) 0.081(16) Uiso 1 1 d . . .
H3 H 0.258(9) 0.662(5) 0.216(6) 0.11(2) Uiso 1 1 d . . .
H2 H 0.198(5) 0.245(3) 0.215(4) 0.029(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 0.0373(11) 0.118(2) 0.0289(11) -0.0074(12) -0.0023(8) 0.0050(12)
O5 0.0400(14) 0.129(3) 0.0342(15) 0.0223(15) 0.0008(11) 0.0225(16)
O1 0.0259(13) 0.141(3) 0.0257(14) -0.0138(16) 0.0038(10) 0.0025(16)
O3 0.0443(16) 0.139(4) 0.0363(16) 0.013(2) 0.0057(12) -0.0036(19)
N2 0.0223(14) 0.114(4) 0.0236(16) -0.0012(19) 0.0031(11) 0.0040(18)
O4 0.0369(14) 0.142(3) 0.0304(15) 0.0247(15) 0.0016(11) 0.0093(17)
O2 0.0341(13) 0.147(3) 0.0252(14) 0.0099(15) 0.0002(10) 0.0096(16)
N1 0.0210(15) 0.151(5) 0.0186(17) -0.008(2) 0.0020(12) 0.0043(19)
C8 0.0186(17) 0.129(5) 0.031(2) 0.025(2) 0.0081(14) 0.011(2)
C4 0.0210(16) 0.125(5) 0.0178(17) -0.004(2) 0.0025(13) 0.008(2)
C3 0.0177(16) 0.128(5) 0.0188(17) -0.003(2) 0.0016(12) 0.007(2)
C10 0.0197(18) 0.159(6) 0.0239(19) 0.020(2) 0.0043(13) 0.000(2)
C5 0.0229(18) 0.129(5) 0.031(2) 0.013(2) 0.0077(14) 0.000(2)
C1 0.0169(17) 0.143(5) 0.0193(19) -0.009(2) 0.0056(13) 0.003(2)
C9 0.0182(17) 0.135(5) 0.032(2) 0.028(2) 0.0056(14) 0.008(2)
C11 0.0193(17) 0.144(6) 0.0267(19) 0.026(2) 0.0065(13) 0.014(2)
C2 0.0168(17) 0.142(5) 0.0228(19) -0.001(2) 0.0042(13) 0.008(2)
C6 0.0219(18) 0.129(5) 0.029(2) 0.020(2) 0.0060(14) 0.004(2)
C7 0.0201(17) 0.134(5) 0.0261(19) 0.022(2) 0.0062(13) 0.006(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 C4 1.348(5) . ?
O5 C11 1.228(5) . ?
O1 C1 1.238(6) . ?
O3 C5 1.366(6) . ?
O3 H3 0.87(7) . ?
N2 C2 1.355(5) . ?
N2 C3 1.368(6) . ?
N2 H2 0.89(4) . ?
O4 C11 1.325(5) . ?
O4 H4 0.8200 . ?
O2 C2 1.230(6) . ?
N1 C2 1.382(6) . ?
N1 C1 1.386(7) . ?
N1 H1 0.81(5) . ?
C8 C7 1.384(6) . ?
C8 C9 1.385(6) . ?
C8 C11 1.479(7) . ?
C4 C3 1.324(7) . ?
C4 C1 1.428(5) . ?
C3 H3A 0.9300 . ?
C10 C9 1.375(7) . ?
C10 C5 1.388(7) . ?
C10 H10 0.9300 . ?
C5 C6 1.382(6) . ?
C9 H9 0.9300 . ?
C6 C7 1.391(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?

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
C5 O3 H3 110(5) . . ?
C2 N2 C3 122.8(5) . . ?
C2 N2 H2 120(2) . . ?
C3 N2 H2 117(2) . . ?
C11 O4 H4 109.5 . . ?
C2 N1 C1 126.2(4) . . ?
C2 N1 H1 119(4) . . ?
C1 N1 H1 115(4) . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 C11 122.1(4) . . ?
C9 C8 C11 118.2(4) . . ?
C3 C4 F1 120.6(3) . . ?
C3 C4 C1 123.4(5) . . ?
F1 C4 C1 116.0(5) . . ?
C4 C3 N2 119.6(4) . . ?
C4 C3 H3A 120.2 . . ?
N2 C3 H3A 120.2 . . ?
C9 C10 C5 119.0(5) . . ?
C9 C10 H10 120.5 . . ?
C5 C10 H10 120.5 . . ?
O3 C5 C6 122.5(5) . . ?
O3 C5 C10 116.3(4) . . ?
C6 C5 C10 121.2(6) . . ?
O1 C1 N1 121.2(4) . . ?
O1 C1 C4 126.3(5) . . ?
N1 C1 C4 112.4(5) . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
O5 C11 O4 122.5(6) . . ?
O5 C11 C8 123.3(4) . . ?
O4 C11 C8 114.2(4) . . ?
O2 C2 N2 123.3(6) . . ?
O2 C2 N1 121.2(4) . . ?
N2 C2 N1 115.5(5) . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?

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 C4 C3 N2 -179.3(3) . . . . ?
C1 C4 C3 N2 1.3(5) . . . . ?
C2 N2 C3 C4 1.4(5) . . . . ?
C9 C10 C5 O3 179.4(3) . . . . ?
C9 C10 C5 C6 -0.2(5) . . . . ?
C2 N1 C1 O1 -177.7(3) . . . . ?
C2 N1 C1 C4 2.4(5) . . . . ?
C3 C4 C1 O1 177.2(3) . . . . ?
F1 C4 C1 O1 -2.3(5) . . . . ?
C3 C4 C1 N1 -3.0(5) . . . . ?
F1 C4 C1 N1 177.5(2) . . . . ?
C5 C10 C9 C8 -0.5(5) . . . . ?
C7 C8 C9 C10 0.8(5) . . . . ?
C11 C8 C9 C10 -179.3(3) . . . . ?
C7 C8 C11 O5 -174.1(3) . . . . ?
C9 C8 C11 O5 6.0(5) . . . . ?
C7 C8 C11 O4 7.0(5) . . . . ?
C9 C8 C11 O4 -172.9(3) . . . . ?
C3 N2 C2 O2 178.5(3) . . . . ?
C3 N2 C2 N1 -2.0(5) . . . . ?
C1 N1 C2 O2 179.5(3) . . . . ?
C1 N1 C2 N2 -0.1(5) . . . . ?
O3 C5 C6 C7 -179.1(3) . . . . ?
C10 C5 C6 C7 0.5(5) . . . . ?
C9 C8 C7 C6 -0.5(5) . . . . ?
C11 C8 C7 C6 179.7(3) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O2 0.82 1.84 2.640(5) 164.8 1_565
N1 H1 O1 0.81(5) 2.22(5) 3.029(4) 171(5) 3_666
N2 H2 O5 0.89(4) 1.91(4) 2.784(6) 167(4) 1_545
O3 H3 O1 0.87(7) 2.16(7) 3.019(5) 168(6) .

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        62.95
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 983684'
