# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_RS-revised

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C13 H10 N2 O4 '
_chemical_formula_moiety         'C13 H10 N2 O4 '
_chemical_formula_weight         258.23
_chemical_melting_point          ?

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z

#------------------------------------------------------------------------------

_cell_length_a                   8.3156(3)
_cell_length_b                   9.9732(4)
_cell_length_c                   14.5740(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.762(2)
_cell_angle_gamma                90.0000
_cell_volume                     1178.81(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7535
_cell_measurement_theta_min      4.4
_cell_measurement_theta_max      68.2
_cell_measurement_temperature    93.1

#------------------------------------------------------------------------------

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536.00
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.963

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku VariMax RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            12229
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_theta_max         68.25
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        68.25
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_ambient_temperature      93.1

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2122
_reflns_number_gt                1530
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1212
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2122
_refine_ls_number_parameters     173
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0596P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.0000
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================

# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.38781(16) 0.44137(12) 0.36954(10) 0.0418(4) Uani 1.00 1 d . . .
O2 O 0.53914(17) 0.05596(12) 0.24160(10) 0.0410(4) Uani 1.00 1 d . . .
O3 O 0.41030(15) 0.42300(12) 0.15938(9) 0.0348(3) Uani 1.00 1 d . . .
O4 O -0.13441(16) 0.38435(12) 0.03562(10) 0.0394(3) Uani 1.00 1 d . . .
N1 N 0.4192(2) 0.24004(14) 0.29688(12) 0.0330(4) Uani 1.00 1 d . . .
N2 N 0.13674(18) 0.40211(13) 0.10034(11) 0.0297(4) Uani 1.00 1 d . . .
H2N H 0.1425 0.4669 0.0602 0.036 Uiso 1.00 1 c R . .
C1 C 0.4718(2) 0.34512(18) 0.35945(14) 0.0329(4) Uani 1.00 1 d . . .
C2 C 0.6455(2) 0.31558(18) 0.40705(14) 0.0315(4) Uani 1.00 1 d . . .
C3 C 0.7551(2) 0.38455(19) 0.47490(14) 0.0361(5) Uani 1.00 1 d . . .
H3 H 0.7249 0.4659 0.5005 0.043 Uiso 1.00 1 c R . .
C4 C 0.9126(2) 0.3303(2) 0.50484(15) 0.0407(5) Uani 1.00 1 d . . .
H4 H 0.9915 0.3758 0.5516 0.049 Uiso 1.00 1 c R . .
C5 C 0.9561(2) 0.2112(2) 0.46749(14) 0.0396(5) Uani 1.00 1 d . . .
H5 H 1.0641 0.1764 0.4893 0.047 Uiso 1.00 1 c R . .
C6 C 0.8442(2) 0.14159(19) 0.39862(14) 0.0343(5) Uani 1.00 1 d . . .
H6 H 0.8733 0.0597 0.3731 0.041 Uiso 1.00 1 c R . .
C7 C 0.6898(2) 0.19667(18) 0.36918(13) 0.0309(4) Uani 1.00 1 d . . .
C8 C 0.5480(2) 0.14990(19) 0.29523(14) 0.0319(4) Uani 1.00 1 d . . .
C9 C 0.2718(2) 0.24380(18) 0.22179(15) 0.0348(5) Uani 1.00 1 d . . .
H9 H 0.2732 0.1620 0.1823 0.042 Uiso 1.00 1 c R . .
C10 C 0.2822(2) 0.36463(18) 0.16027(14) 0.0304(4) Uani 1.00 1 d . . .
C11 C -0.0169(2) 0.34803(17) 0.09717(14) 0.0314(4) Uani 1.00 1 d . . .
C12 C -0.0315(2) 0.24494(17) 0.16986(15) 0.0341(5) Uani 1.00 1 d . . .
H12A H -0.0411 0.1553 0.1399 0.041 Uiso 1.00 1 c R . .
H12B H -0.1344 0.2618 0.1916 0.041 Uiso 1.00 1 c R . .
C13 C 0.1108(2) 0.24274(19) 0.25434(15) 0.0389(5) Uani 1.00 1 d . . .
H13A H 0.1045 0.1612 0.2922 0.047 Uiso 1.00 1 c R . .
H13B H 0.1051 0.3221 0.2943 0.047 Uiso 1.00 1 c R . .



#==============================================================================

_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'

#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C1 1.215(2) yes . .
O2 C8 1.212(2) yes . .
O3 C10 1.216(2) yes . .
O4 C11 1.226(2) yes . .
N1 C1 1.395(2) yes . .
N1 C8 1.403(2) yes . .
N1 C9 1.452(2) yes . .
N2 C10 1.378(2) yes . .
N2 C11 1.378(2) yes . .
C1 C2 1.487(2) yes . .
C2 C3 1.372(2) yes . .
C2 C7 1.392(2) yes . .
C3 C4 1.395(2) yes . .
C4 C5 1.388(3) yes . .
C5 C6 1.393(2) yes . .
C6 C7 1.375(2) yes . .
C7 C8 1.486(2) yes . .
C9 C10 1.516(2) yes . .
C9 C13 1.517(3) yes . .
C11 C12 1.500(2) yes . .
C12 C13 1.507(2) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C8 111.25(14) yes . . .
C1 N1 C9 124.33(14) yes . . .
C8 N1 C9 121.61(15) yes . . .
C10 N2 C11 126.35(15) yes . . .
O1 C1 N1 124.56(16) yes . . .
O1 C1 C2 128.69(16) yes . . .
N1 C1 C2 106.75(15) yes . . .
C1 C2 C3 131.21(17) yes . . .
C1 C2 C7 107.40(15) yes . . .
C3 C2 C7 121.39(17) yes . . .
C2 C3 C4 117.35(18) yes . . .
C3 C4 C5 121.13(17) yes . . .
C4 C5 C6 121.25(18) yes . . .
C5 C6 C7 117.03(18) yes . . .
C2 C7 C6 121.85(16) yes . . .
C2 C7 C8 108.52(15) yes . . .
C6 C7 C8 129.61(17) yes . . .
O2 C8 N1 124.66(16) yes . . .
O2 C8 C7 129.48(17) yes . . .
N1 C8 C7 105.85(15) yes . . .
N1 C9 C10 108.51(14) yes . . .
N1 C9 C13 114.88(18) yes . . .
C10 C9 C13 111.12(15) yes . . .
O3 C10 N2 120.77(16) yes . . .
O3 C10 C9 123.46(15) yes . . .
N2 C10 C9 115.70(15) yes . . .
O4 C11 N2 119.46(17) yes . . .
O4 C11 C12 122.94(17) yes . . .
N2 C11 C12 117.59(15) yes . . .
C11 C12 C13 114.56(15) yes . . .
C9 C13 C12 109.41(18) yes . . .

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N(2) H(2N) O(4) . . 3_565 2.9061(19) 0.880 2.028 175.1 no

#===END========================================================================


_database_code_depnum_ccdc_archive 'CCDC 1009508'
#######################################################################
#
#                 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_tori2-offline

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H9 N2 O4'
_chemical_formula_moiety         'C13 H9 N2 O4'
_chemical_formula_weight         257.23
_chemical_melting_point          ?
_chemical_absolute_configuration ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.3745(4)
_cell_length_b                   10.0838(5)
_cell_length_c                   14.5833(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.496(3)
_cell_angle_gamma                90.0000
_cell_volume                     1197.50(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7928
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532.00
_exptl_absorpt_coefficient_mu    0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.017
_exptl_absorpt_correction_T_max  0.912

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            11473
_diffrn_reflns_av_R_equivalents  0.2427
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_full        68.21
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3768
_reflns_number_gt                1226
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2100
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3768
_refine_ls_number_parameters     343
_refine_ls_goodness_of_fit_ref   0.706
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.390
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.1540(6) 0.6800(6) -0.0945(4) 0.0464(16) Uani 1.0 2 d . . .
O2 O 0.8688(7) 0.8653(7) 0.7121(4) 0.0575(19) Uani 1.0 2 d . . .
O3 O -0.3931(7) 0.6403(7) -0.2049(4) 0.0552(18) Uani 1.0 2 d . . .
O4 O 0.3261(6) 0.8049(6) 0.5873(4) 0.0457(15) Uani 1.0 2 d . . .
O5 O 0.1522(6) 0.6985(6) 0.1180(4) 0.0464(16) Uani 1.0 2 d . . .
O6 O 0.2680(7) 1.1297(7) 0.4996(4) 0.0559(18) Uani 1.0 2 d . . .
O7 O 0.2840(6) 0.3113(6) -0.0112(4) 0.0471(16) Uani 1.0 2 d . . .
O8 O 0.2836(7) 0.7341(7) 0.3445(4) 0.0553(19) Uani 1.0 2 d . . .
N9 N 0.1744(7) 0.4957(7) 0.0449(4) 0.0358(17) Uani 1.0 2 d . . .
N10 N -0.1201(7) 0.6575(8) -0.1458(4) 0.0402(18) Uani 1.0 2 d . . .
N11 N 0.5988(7) 0.8371(8) 0.6462(4) 0.0414(19) Uani 1.0 2 d . . .
N12 N 0.3204(7) 0.9353(8) 0.4240(5) 0.0414(18) Uani 1.0 2 d . . .
C13 C -0.2718(10) 0.6044(9) -0.1451(6) 0.042(3) Uani 1.0 2 d . . .
C14 C 0.0307(9) 0.6218(9) -0.0897(5) 0.038(2) Uani 1.0 2 d . . .
C15 C 0.0663(10) 0.9057(9) 0.3248(6) 0.045(3) Uani 1.0 2 d . . .
C16 C 0.4423(9) 0.4499(10) 0.1173(6) 0.042(3) Uani 1.0 2 d . . .
C17 C -0.2122(9) 1.0594(11) 0.2868(6) 0.049(3) Uani 1.0 2 d . . .
C18 C 0.2292(11) 0.8403(11) 0.3606(6) 0.052(3) Uani 1.0 2 d . . .
C19 C 0.0224(9) 0.4995(9) -0.0270(5) 0.035(2) Uani 1.0 2 d . . .
C20 C 0.7112(10) 0.4522(12) 0.2201(6) 0.059(3) Uani 1.0 2 d . . .
C21 C 0.4564(9) 0.8451(10) 0.5753(6) 0.044(3) Uani 1.0 2 d . . .
C22 C 0.6066(9) 1.0090(10) 0.4956(6) 0.051(3) Uani 1.0 2 d . . .
C23 C 0.7540(10) 0.8818(9) 0.6440(6) 0.044(3) Uani 1.0 2 d . . .
C24 C -0.2779(9) 0.5034(10) -0.0735(5) 0.044(3) Uani 1.0 2 d . . .
C25 C -0.0659(10) 0.8597(10) 0.2585(5) 0.049(3) Uani 1.0 2 d . . .
C26 C 0.2225(10) 1.0413(10) 0.4385(7) 0.050(3) Uani 1.0 2 d . . .
C27 C 0.4056(9) 0.5677(10) 0.1581(6) 0.044(3) Uani 1.0 2 d . . .
C28 C -0.2079(10) 0.9410(11) 0.2386(6) 0.054(3) Uani 1.0 2 d . . .
C29 C 0.0634(9) 1.0213(11) 0.3729(6) 0.049(3) Uani 1.0 2 d . . .
C30 C 0.4800(9) 0.8947(9) 0.4822(5) 0.044(3) Uani 1.0 2 d . . .
C31 C 0.5968(9) 0.3869(10) 0.1483(6) 0.051(3) Uani 1.0 2 d . . .
C32 C 0.7698(10) 0.9564(10) 0.5553(6) 0.049(3) Uani 1.0 2 d . . .
C33 C -0.1286(8) 0.5067(10) 0.0122(5) 0.046(3) Uani 1.0 2 d . . .
C34 C 0.6742(10) 0.5712(11) 0.2593(6) 0.059(3) Uani 1.0 2 d . . .
C35 C -0.0774(10) 1.1011(10) 0.3540(6) 0.050(3) Uani 1.0 2 d . . .
C36 C 0.2992(10) 0.4057(10) 0.0428(6) 0.040(3) Uani 1.0 2 d . . .
C37 C 0.5187(9) 0.6304(10) 0.2279(5) 0.049(3) Uani 1.0 2 d . . .
C38 C 0.2329(9) 0.6044(9) 0.1083(6) 0.035(2) Uani 1.0 2 d . . .
H10 H -0.1193 0.7215 -0.1867 0.0482 Uiso 1.0 2 calc R . .
H11 H 0.5892 0.7990 0.6990 0.0497 Uiso 1.0 2 calc R . .
H17 H -0.3090 1.1119 0.2733 0.0584 Uiso 1.0 2 calc R . .
H20 H 0.8169 0.4141 0.2425 0.0703 Uiso 1.0 2 calc R . .
H22A H 0.6211 1.0398 0.4336 0.0610 Uiso 1.0 2 calc R . .
H22B H 0.5680 1.0847 0.5279 0.0610 Uiso 1.0 2 calc R . .
H24A H -0.2841 0.4147 -0.1032 0.0528 Uiso 1.0 2 calc R . .
H24B H -0.3794 0.5163 -0.0508 0.0528 Uiso 1.0 2 calc R . .
H25 H -0.0626 0.7773 0.2274 0.0582 Uiso 1.0 2 calc R . .
H28 H -0.3013 0.9144 0.1917 0.0643 Uiso 1.0 2 calc R . .
H31 H 0.6216 0.3053 0.1221 0.0610 Uiso 1.0 2 calc R . .
H32A H 0.8194 0.8964 0.5159 0.0593 Uiso 1.0 2 calc R . .
H32B H 0.8458 1.0320 0.5742 0.0593 Uiso 1.0 2 calc R . .
H33A H -0.1286 0.5895 0.0485 0.0550 Uiso 1.0 2 calc R . .
H33B H -0.1322 0.4304 0.0544 0.0550 Uiso 1.0 2 calc R . .
H34 H 0.7546 0.6127 0.3076 0.0713 Uiso 1.0 2 calc R . .
H35 H -0.0798 1.1821 0.3869 0.0598 Uiso 1.0 2 calc R . .
H37 H 0.4928 0.7115 0.2543 0.0583 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C14 1.203(10) yes . .
O2 C23 1.222(9) yes . .
O3 C13 1.229(9) yes . .
O4 C21 1.215(10) yes . .
O5 C38 1.193(11) yes . .
O6 C26 1.255(12) yes . .
O7 C36 1.223(11) yes . .
O8 C18 1.207(13) yes . .
N9 C19 1.449(8) yes . .
N9 C36 1.390(11) yes . .
N9 C38 1.444(11) yes . .
N10 C13 1.381(11) yes . .
N10 C14 1.383(9) yes . .
N11 C21 1.387(9) yes . .
N11 C23 1.384(11) yes . .
N12 C18 1.424(12) yes . .
N12 C26 1.392(13) yes . .
N12 C30 1.465(9) yes . .
C13 C24 1.468(13) yes . .
C14 C19 1.546(12) yes . .
C15 C18 1.495(12) yes . .
C15 C25 1.370(11) yes . .
C15 C29 1.364(14) yes . .
C16 C27 1.394(13) yes . .
C16 C31 1.417(11) yes . .
C16 C36 1.486(10) yes . .
C17 C28 1.390(15) yes . .
C17 C35 1.377(11) yes . .
C19 C33 1.506(11) yes . .
C20 C31 1.407(11) yes . .
C20 C34 1.395(15) yes . .
C21 C30 1.502(12) yes . .
C22 C30 1.547(12) yes . .
C22 C32 1.533(11) yes . .
C23 C32 1.529(13) yes . .
C24 C33 1.548(9) yes . .
C25 C28 1.418(13) yes . .
C26 C29 1.461(10) yes . .
C27 C37 1.373(11) yes . .
C27 C38 1.505(10) yes . .
C29 C35 1.401(12) yes . .
C34 C37 1.408(12) yes . .
N10 H10 0.880 no . .
N11 H11 0.880 no . .
C17 H17 0.950 no . .
C20 H20 0.950 no . .
C22 H22A 0.990 no . .
C22 H22B 0.990 no . .
C24 H24A 0.990 no . .
C24 H24B 0.990 no . .
C25 H25 0.950 no . .
C28 H28 0.950 no . .
C31 H31 0.950 no . .
C32 H32A 0.990 no . .
C32 H32B 0.990 no . .
C33 H33A 0.990 no . .
C33 H33B 0.990 no . .
C34 H34 0.950 no . .
C35 H35 0.950 no . .
C37 H37 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C19 N9 C36 122.7(7) yes . . .
C19 N9 C38 123.5(7) yes . . .
C36 N9 C38 111.4(6) yes . . .
C13 N10 C14 127.5(7) yes . . .
C21 N11 C23 127.8(7) yes . . .
C18 N12 C26 111.7(7) yes . . .
C18 N12 C30 117.8(8) yes . . .
C26 N12 C30 128.1(7) yes . . .
O3 C13 N10 119.3(8) yes . . .
O3 C13 C24 123.3(8) yes . . .
N10 C13 C24 117.3(7) yes . . .
O1 C14 N10 121.1(8) yes . . .
O1 C14 C19 125.5(7) yes . . .
N10 C14 C19 113.4(7) yes . . .
C18 C15 C25 128.2(9) yes . . .
C18 C15 C29 108.8(7) yes . . .
C25 C15 C29 123.0(8) yes . . .
C27 C16 C31 121.5(7) yes . . .
C27 C16 C36 110.3(7) yes . . .
C31 C16 C36 128.2(9) yes . . .
C28 C17 C35 120.6(8) yes . . .
O8 C18 N12 123.6(8) yes . . .
O8 C18 C15 132.7(8) yes . . .
N12 C18 C15 103.7(8) yes . . .
N9 C19 C14 107.2(6) yes . . .
N9 C19 C33 113.6(6) yes . . .
C14 C19 C33 110.1(7) yes . . .
C31 C20 C34 122.0(8) yes . . .
O4 C21 N11 121.2(8) yes . . .
O4 C21 C30 123.6(7) yes . . .
N11 C21 C30 115.0(7) yes . . .
C30 C22 C32 107.9(8) yes . . .
O2 C23 N11 120.1(8) yes . . .
O2 C23 C32 123.2(8) yes . . .
N11 C23 C32 116.6(7) yes . . .
C13 C24 C33 113.8(7) yes . . .
C15 C25 C28 116.7(9) yes . . .
O6 C26 N12 124.1(7) yes . . .
O6 C26 C29 129.9(9) yes . . .
N12 C26 C29 105.9(8) yes . . .
C16 C27 C37 121.7(8) yes . . .
C16 C27 C38 106.6(7) yes . . .
C37 C27 C38 131.6(9) yes . . .
C17 C28 C25 120.8(7) yes . . .
C15 C29 C26 109.4(8) yes . . .
C15 C29 C35 120.3(7) yes . . .
C26 C29 C35 130.3(9) yes . . .
N12 C30 C21 108.8(7) yes . . .
N12 C30 C22 111.8(7) yes . . .
C21 C30 C22 111.4(7) yes . . .
C16 C31 C20 116.1(9) yes . . .
C22 C32 C23 114.1(7) yes . . .
C19 C33 C24 106.5(6) yes . . .
C20 C34 C37 120.6(8) yes . . .
C17 C35 C29 118.5(9) yes . . .
O7 C36 N9 123.8(7) yes . . .
O7 C36 C16 130.5(8) yes . . .
N9 C36 C16 105.7(7) yes . . .
C27 C37 C34 118.1(9) yes . . .
O5 C38 N9 124.3(6) yes . . .
O5 C38 C27 130.2(8) yes . . .
N9 C38 C27 105.5(7) yes . . .
C13 N10 H10 116.232 no . . .
C14 N10 H10 116.235 no . . .
C21 N11 H11 116.119 no . . .
C23 N11 H11 116.123 no . . .
C28 C17 H17 119.709 no . . .
C35 C17 H17 119.696 no . . .
C31 C20 H20 119.014 no . . .
C34 C20 H20 119.019 no . . .
C30 C22 H22A 110.114 no . . .
C30 C22 H22B 110.115 no . . .
C32 C22 H22A 110.112 no . . .
C32 C22 H22B 110.118 no . . .
H22A C22 H22B 108.433 no . . .
C13 C24 H24A 108.804 no . . .
C13 C24 H24B 108.795 no . . .
C33 C24 H24A 108.798 no . . .
C33 C24 H24B 108.797 no . . .
H24A C24 H24B 107.670 no . . .
C15 C25 H25 121.635 no . . .
C28 C25 H25 121.636 no . . .
C17 C28 H28 119.585 no . . .
C25 C28 H28 119.589 no . . .
C16 C31 H31 121.952 no . . .
C20 C31 H31 121.951 no . . .
C22 C32 H32A 108.725 no . . .
C22 C32 H32B 108.730 no . . .
C23 C32 H32A 108.725 no . . .
C23 C32 H32B 108.728 no . . .
H32A C32 H32B 107.629 no . . .
C19 C33 H33A 110.421 no . . .
C19 C33 H33B 110.414 no . . .
C24 C33 H33A 110.423 no . . .
C24 C33 H33B 110.416 no . . .
H33A C33 H33B 108.623 no . . .
C20 C34 H34 119.702 no . . .
C37 C34 H34 119.698 no . . .
C17 C35 H35 120.739 no . . .
C29 C35 H35 120.745 no . . .
C27 C37 H37 120.944 no . . .
C34 C37 H37 120.951 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C19 N9 C36 O7 -10.4(13) no . . . .
C19 N9 C36 C16 169.9(6) no . . . .
C36 N9 C19 C14 -105.2(8) no . . . .
C36 N9 C19 C33 132.9(8) no . . . .
C19 N9 C38 O5 12.2(12) no . . . .
C19 N9 C38 C27 -170.2(6) no . . . .
C38 N9 C19 C14 55.9(9) no . . . .
C38 N9 C19 C33 -66.0(10) no . . . .
C36 N9 C38 O5 175.2(8) no . . . .
C36 N9 C38 C27 -7.3(8) no . . . .
C38 N9 C36 O7 -173.6(8) no . . . .
C38 N9 C36 C16 6.8(9) no . . . .
C13 N10 C14 O1 -176.8(8) no . . . .
C13 N10 C14 C19 6.0(11) no . . . .
C14 N10 C13 O3 -174.3(7) no . . . .
C14 N10 C13 C24 3.8(12) no . . . .
C21 N11 C23 O2 -178.8(8) no . . . .
C21 N11 C23 C32 4.0(13) no . . . .
C23 N11 C21 O4 -178.0(8) no . . . .
C23 N11 C21 C30 7.3(13) no . . . .
C18 N12 C26 O6 171.0(9) no . . . .
C18 N12 C26 C29 -6.5(10) no . . . .
C26 N12 C18 O8 -172.5(9) no . . . .
C26 N12 C18 C15 7.8(9) no . . . .
C18 N12 C30 C21 -93.3(8) no . . . .
C18 N12 C30 C22 143.3(7) no . . . .
C30 N12 C18 O8 -8.7(13) no . . . .
C30 N12 C18 C15 171.5(6) no . . . .
C26 N12 C30 C21 67.4(11) no . . . .
C26 N12 C30 C22 -56.0(11) no . . . .
C30 N12 C26 O6 9.3(15) no . . . .
C30 N12 C26 C29 -168.2(7) no . . . .
O3 C13 C24 C33 -161.0(8) no . . . .
N10 C13 C24 C33 20.9(11) no . . . .
O1 C14 C19 N9 18.4(11) no . . . .
O1 C14 C19 C33 142.5(8) no . . . .
N10 C14 C19 N9 -164.5(6) no . . . .
N10 C14 C19 C33 -40.4(9) no . . . .
C18 C15 C25 C28 178.8(8) no . . . .
C25 C15 C18 O8 -2.8(17) no . . . .
C25 C15 C18 N12 176.9(9) no . . . .
C18 C15 C29 C26 2.5(10) no . . . .
C18 C15 C29 C35 -178.8(7) no . . . .
C29 C15 C18 O8 174.2(10) no . . . .
C29 C15 C18 N12 -6.1(10) no . . . .
C25 C15 C29 C26 179.6(8) no . . . .
C25 C15 C29 C35 -1.7(14) no . . . .
C29 C15 C25 C28 2.3(13) no . . . .
C27 C16 C31 C20 -1.9(12) no . . . .
C31 C16 C27 C37 2.1(13) no . . . .
C31 C16 C27 C38 -179.7(7) no . . . .
C27 C16 C36 O7 176.8(9) no . . . .
C27 C16 C36 N9 -3.6(10) no . . . .
C36 C16 C27 C37 -178.9(7) no . . . .
C36 C16 C27 C38 -0.8(10) no . . . .
C31 C16 C36 O7 -4.4(16) no . . . .
C31 C16 C36 N9 175.3(8) no . . . .
C36 C16 C31 C20 179.4(8) no . . . .
C28 C17 C35 C29 -0.3(13) no . . . .
C35 C17 C28 C25 1.0(13) no . . . .
N9 C19 C33 C24 -177.4(7) no . . . .
C14 C19 C33 C24 62.3(8) no . . . .
C31 C20 C34 C37 0.1(14) no . . . .
C34 C20 C31 C16 0.7(13) no . . . .
O4 C21 C30 N12 22.1(12) no . . . .
O4 C21 C30 C22 145.7(8) no . . . .
N11 C21 C30 N12 -163.4(7) no . . . .
N11 C21 C30 C22 -39.7(10) no . . . .
C30 C22 C32 C23 -48.3(9) no . . . .
C32 C22 C30 N12 -178.8(6) no . . . .
C32 C22 C30 C21 59.3(9) no . . . .
O2 C23 C32 C22 -158.9(8) no . . . .
N11 C23 C32 C22 18.2(11) no . . . .
C13 C24 C33 C19 -53.3(10) no . . . .
C15 C25 C28 C17 -1.9(13) no . . . .
O6 C26 C29 C15 -175.0(9) no . . . .
O6 C26 C29 C35 6.5(17) no . . . .
N12 C26 C29 C15 2.3(10) no . . . .
N12 C26 C29 C35 -176.3(8) no . . . .
C16 C27 C37 C34 -1.2(13) no . . . .
C16 C27 C38 O5 -177.9(9) no . . . .
C16 C27 C38 N9 4.7(9) no . . . .
C37 C27 C38 O5 -0.0(16) no . . . .
C37 C27 C38 N9 -177.4(9) no . . . .
C38 C27 C37 C34 -178.8(8) no . . . .
C15 C29 C35 C17 0.6(13) no . . . .
C26 C29 C35 C17 179.1(9) no . . . .
C20 C34 C37 C27 0.1(13) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 O5 3.108(7) no . .
O1 N9 2.730(9) no . .
O1 C13 3.551(10) no . .
O1 C33 3.576(10) no . .
O1 C36 3.465(11) no . .
O1 C38 2.975(9) no . .
O2 C21 3.569(9) no . .
O3 C14 3.559(9) no . .
O4 O6 3.508(9) no . .
O4 O8 3.547(8) no . .
O4 N12 2.711(9) no . .
O4 C18 3.234(10) no . .
O4 C23 3.570(10) no . .
O4 C26 3.204(11) no . .
O5 C14 3.062(9) no . .
O5 C16 3.493(11) no . .
O5 C19 2.934(10) no . .
O5 C33 3.156(10) no . .
O5 C36 3.474(11) no . .
O5 C37 3.188(9) no . .
O6 C15 3.527(10) no . .
O6 C18 3.525(12) no . .
O6 C21 3.336(11) no . .
O6 C22 3.099(10) no . .
O6 C30 3.007(11) no . .
O6 C35 3.176(9) no . .
O7 C19 2.867(10) no . .
O7 C27 3.556(11) no . .
O7 C31 3.164(8) no . .
O7 C38 3.507(11) no . .
O8 C21 3.521(10) no . .
O8 C25 3.167(10) no . .
O8 C26 3.472(12) no . .
O8 C29 3.509(12) no . .
O8 C30 2.796(10) no . .
N10 C33 2.775(11) no . .
N11 C22 2.811(12) no . .
C13 C19 2.859(10) no . .
C14 C24 2.906(11) no . .
C14 C36 3.393(11) no . .
C14 C38 2.992(10) no . .
C15 C17 2.747(12) no . .
C16 C34 2.770(11) no . .
C18 C21 3.262(11) no . .
C20 C27 2.765(12) no . .
C21 C26 3.147(12) no . .
C21 C32 2.931(12) no . .
C22 C26 3.146(11) no . .
C23 C30 2.885(10) no . .
C25 C35 2.817(14) no . .
C28 C29 2.753(10) no . .
C31 C37 2.857(14) no . .
C33 C38 3.181(10) no . .
O1 C17 3.198(10) no . 2_545
O1 C28 3.297(12) no . 2_545
O1 C31 3.177(11) no . 2_655
O1 C33 3.529(12) no . 2_555
O2 O3 3.558(9) no . 1_656
O2 N10 2.933(9) no . 1_656
O2 C20 3.534(10) no . 2_756
O2 C35 3.446(12) no . 2_646
O3 O2 3.558(9) no . 1_454
O3 O7 3.521(8) no . 2_555
O3 N11 2.931(9) no . 1_454
O3 C16 3.434(12) no . 2_555
O3 C17 3.344(9) no . 2_445
O3 C31 3.230(11) no . 2_555
O3 C36 3.535(11) no . 2_555
O4 C17 3.351(12) no . 2_546
O4 C20 3.257(11) no . 2_656
O4 C22 3.317(12) no . 2_646
O4 C34 3.496(12) no . 2_656
O4 C35 3.182(11) no . 2_546
O5 O8 3.248(7) no . .
O5 C19 3.494(10) no . 2_555
O5 C24 3.362(11) no . 2_555
O5 C25 3.452(11) no . .
O6 N11 3.354(10) no . 2_656
O6 C21 3.523(11) no . 2_656
O6 C23 3.271(11) no . 2_656
O6 C30 3.377(11) no . 2_656
O6 C32 3.388(12) no . 2_656
O6 C34 3.487(11) no . 2_656
O7 O3 3.521(8) no . 2_545
O7 N10 3.317(9) no . 2_545
O7 C13 3.110(11) no . 2_545
O7 C24 3.346(11) no . 2_545
O7 C28 3.482(10) no . 2_545
O7 C33 3.335(12) no . 2_545
O8 O5 3.248(7) no . .
O8 C22 3.230(11) no . 2_646
O8 C23 3.575(12) no . 2_646
O8 C27 3.542(11) no . .
O8 C32 3.238(12) no . 2_646
O8 C37 3.070(11) no . .
N10 O2 2.933(9) no . 1_454
N10 O7 3.317(9) no . 2_555
N10 C36 3.438(12) no . 2_555
N11 O3 2.931(9) no . 1_656
N11 O6 3.354(10) no . 2_646
C13 O7 3.110(11) no . 2_555
C13 C36 3.416(13) no . 2_555
C14 C28 3.427(13) no . 2_545
C16 O3 3.434(12) no . 2_545
C17 O1 3.198(10) no . 2_555
C17 O3 3.344(9) no . 2_455
C17 O4 3.351(12) no . 2_556
C19 O5 3.494(10) no . 2_545
C20 O2 3.534(10) no . 2_746
C20 O4 3.257(11) no . 2_646
C21 O6 3.523(11) no . 2_646
C21 C22 3.547(14) no . 2_646
C22 O4 3.317(12) no . 2_656
C22 O8 3.230(11) no . 2_656
C22 C21 3.547(14) no . 2_656
C23 O6 3.271(11) no . 2_646
C23 O8 3.575(12) no . 2_656
C24 O5 3.362(11) no . 2_545
C24 O7 3.346(11) no . 2_555
C25 O5 3.452(11) no . .
C27 O8 3.542(11) no . .
C28 O1 3.297(12) no . 2_555
C28 O7 3.482(10) no . 2_555
C28 C14 3.427(13) no . 2_555
C30 O6 3.377(11) no . 2_646
C31 O1 3.177(11) no . 2_645
C31 O3 3.230(11) no . 2_545
C31 C33 3.581(12) no . 1_655
C32 O6 3.388(12) no . 2_646
C32 O8 3.238(12) no . 2_656
C33 O1 3.529(12) no . 2_545
C33 O7 3.335(12) no . 2_555
C33 C31 3.581(12) no . 1_455
C34 O4 3.496(12) no . 2_646
C34 O6 3.487(11) no . 2_646
C35 O2 3.446(12) no . 2_656
C35 O4 3.182(11) no . 2_556
C36 O3 3.535(11) no . 2_545
C36 N10 3.438(12) no . 2_545
C36 C13 3.416(13) no . 2_545
C37 O8 3.070(11) no . .
O1 H10 2.4052 no . .
O2 H11 2.3992 no . .
O2 H32A 2.8126 no . .
O2 H32B 2.5946 no . .
O3 H10 2.3903 no . .
O3 H24A 2.7524 no . .
O3 H24B 2.5512 no . .
O4 H11 2.4162 no . .
O5 H33A 2.5791 no . .
O5 H33B 3.5797 no . .
O5 H37 3.0754 no . .
O6 H22A 3.4379 no . .
O6 H22B 2.4908 no . .
O6 H35 3.0380 no . .
O7 H31 3.0351 no . .
O8 H25 3.0331 no . .
N9 H33A 2.7205 no . .
N9 H33B 2.6852 no . .
N10 H24A 2.9442 no . .
N10 H24B 3.1733 no . .
N10 H33A 2.9329 no . .
N11 H22B 3.0114 no . .
N11 H32A 3.0042 no . .
N11 H32B 3.2037 no . .
N12 H22A 2.7030 no . .
N12 H22B 2.7200 no . .
C13 H33A 2.8026 no . .
C13 H33B 3.3645 no . .
C14 H24A 3.3332 no . .
C14 H33A 2.6844 no . .
C14 H33B 3.3673 no . .
C15 H28 3.2350 no . .
C15 H35 3.2562 no . .
C16 H20 3.2605 no . .
C16 H37 3.2764 no . .
C17 H25 3.3040 no . .
C18 H25 2.8165 no . .
C19 H10 3.2487 no . .
C19 H24A 2.6878 no . .
C19 H24B 3.3054 no . .
C20 H37 3.2950 no . .
C21 H22A 3.3693 no . .
C21 H22B 2.7361 no . .
C21 H32A 3.3896 no . .
C23 H22A 3.4051 no . .
C23 H22B 2.8719 no . .
C24 H10 3.2177 no . .
C25 H17 3.2963 no . .
C26 H22A 3.3555 no . .
C26 H22B 2.9163 no . .
C26 H35 2.8465 no . .
C27 H31 3.3151 no . .
C27 H34 3.2444 no . .
C28 H35 3.2640 no . .
C29 H17 3.2491 no . .
C29 H25 3.2598 no . .
C30 H11 3.2270 no . .
C30 H32A 2.7692 no . .
C30 H32B 3.3440 no . .
C31 H34 3.3002 no . .
C32 H11 3.2677 no . .
C34 H31 3.3122 no . .
C35 H28 3.2551 no . .
C36 H31 2.8625 no . .
C37 H20 3.2851 no . .
C38 H33A 2.9521 no . .
C38 H33B 3.4528 no . .
C38 H37 2.8772 no . .
H17 H28 2.3298 no . .
H17 H35 2.3328 no . .
H20 H31 2.3709 no . .
H20 H34 2.3263 no . .
H22A H32A 2.3145 no . .
H22A H32B 2.4387 no . .
H22B H32A 2.8708 no . .
H22B H32B 2.3274 no . .
H24A H33A 2.8905 no . .
H24A H33B 2.3575 no . .
H24B H33A 2.3735 no . .
H24B H33B 2.4301 no . .
H25 H28 2.3854 no . .
H34 H37 2.3677 no . .
O1 H17 3.2468 no . 2_545
O1 H20 3.2468 no . 2_655
O1 H28 3.3944 no . 2_545
O1 H31 2.3764 no . 2_655
O1 H33B 2.6077 no . 2_555
O2 H10 2.0543 no . 1_656
O2 H20 2.6067 no . 2_756
O2 H35 3.1328 no . 2_646
O3 H11 2.1102 no . 1_454
O3 H17 2.4783 no . 2_445
O3 H22A 3.5814 no . 2_545
O3 H28 3.4654 no . 2_445
O3 H31 2.9944 no . 2_555
O4 H17 2.8416 no . 2_546
O4 H20 3.1928 no . 2_656
O4 H22A 2.7383 no . 2_646
O4 H22B 3.0392 no . 2_646
O4 H34 3.5948 no . 2_656
O4 H35 2.5081 no . 2_546
O5 H24A 2.4761 no . 2_555
O5 H25 2.7834 no . .
O5 H33B 3.4083 no . 2_555
O6 H32A 2.7829 no . 2_656
O6 H34 2.8677 no . 2_656
O7 H10 3.5933 no . 2_545
O7 H24B 3.1569 no . 2_545
O7 H25 3.2806 no . 2_545
O7 H28 2.8641 no . 2_545
O7 H33A 2.5807 no . 2_545
O8 H22B 2.4899 no . 2_646
O8 H32B 2.7081 no . 2_646
O8 H37 2.4350 no . .
N9 H10 3.5463 no . 2_545
N10 H11 3.2426 no . 1_454
N10 H33B 3.5349 no . 2_555
N11 H10 3.1913 no . 1_656
N11 H22A 3.5680 no . 2_646
C13 H11 3.0238 no . 1_454
C13 H17 3.5726 no . 2_445
C14 H31 3.5735 no . 2_655
C14 H33B 3.2349 no . 2_555
C16 H11 3.1452 no . 2_646
C16 H24B 3.2239 no . 1_655
C17 H22A 2.8222 no . 1_455
C17 H31 3.5069 no . 1_465
C18 H22B 3.2987 no . 2_646
C18 H32B 3.3522 no . 2_646
C18 H37 3.2498 no . .
C20 H11 3.3907 no . 2_646
C20 H17 3.5310 no . 1_645
C20 H33A 3.3974 no . 1_655
C20 H33B 3.0148 no . 1_655
C21 H22A 3.1428 no . 2_646
C21 H22B 3.0098 no . 2_646
C23 H10 2.9345 no . 1_656
C23 H35 3.5032 no . 2_646
C25 H34 3.0790 no . 1_455
C27 H11 3.4124 no . 2_646
C28 H34 3.4960 no . 1_455
C28 H37 3.4580 no . 1_455
C29 H10 3.5021 no . 2_555
C29 H32A 3.4778 no . 1_455
C30 H22B 3.1511 no . 2_646
C31 H11 3.1291 no . 2_646
C31 H17 3.3113 no . 1_645
C31 H24B 3.2310 no . 1_655
C31 H33B 2.9450 no . 1_655
C33 H31 3.5550 no . 1_455
C34 H25 3.1424 no . 1_655
C35 H10 3.4673 no . 2_555
C35 H20 3.5669 no . 1_465
C35 H22A 3.0777 no . 1_455
C35 H32A 3.3948 no . 1_455
C35 H32B 3.4878 no . 1_455
C36 H10 3.4050 no . 2_545
C36 H24B 3.4738 no . 1_655
C36 H28 3.4249 no . 2_545
C37 H28 3.3346 no . 1_655
C38 H24A 3.1619 no . 2_555
H10 O2 2.0543 no . 1_454
H10 O7 3.5933 no . 2_555
H10 N9 3.5463 no . 2_555
H10 N11 3.1913 no . 1_454
H10 C23 2.9345 no . 1_454
H10 C29 3.5021 no . 2_545
H10 C35 3.4673 no . 2_545
H10 C36 3.4050 no . 2_555
H10 H11 2.7293 no . 1_454
H10 H20 3.4366 no . 2_655
H10 H33B 3.2705 no . 2_555
H11 O3 2.1102 no . 1_656
H11 N10 3.2426 no . 1_656
H11 C13 3.0238 no . 1_656
H11 C16 3.1452 no . 2_656
H11 C20 3.3907 no . 2_656
H11 C27 3.4124 no . 2_656
H11 C31 3.1291 no . 2_656
H11 H10 2.7293 no . 1_656
H11 H17 3.1100 no . 2_546
H11 H22A 3.4761 no . 2_646
H11 H31 3.4751 no . 2_656
H17 O1 3.2468 no . 2_555
H17 O3 2.4783 no . 2_455
H17 O4 2.8416 no . 2_556
H17 C13 3.5726 no . 2_455
H17 C20 3.5310 no . 1_465
H17 C31 3.3113 no . 1_465
H17 H11 3.1100 no . 2_556
H17 H20 3.2895 no . 1_465
H17 H22A 2.6407 no . 1_455
H17 H31 2.8992 no . 1_465
H20 O1 3.2468 no . 2_645
H20 O2 2.6067 no . 2_746
H20 O4 3.1928 no . 2_646
H20 C35 3.5669 no . 1_645
H20 H10 3.4366 no . 2_645
H20 H17 3.2895 no . 1_645
H20 H33A 3.4559 no . 1_655
H20 H33B 2.8784 no . 1_655
H20 H35 3.1310 no . 1_645
H22A O3 3.5814 no . 2_555
H22A O4 2.7383 no . 2_656
H22A N11 3.5680 no . 2_656
H22A C17 2.8222 no . 1_655
H22A C21 3.1428 no . 2_656
H22A C35 3.0777 no . 1_655
H22A H11 3.4761 no . 2_656
H22A H17 2.6407 no . 1_655
H22A H35 3.0975 no . 1_655
H22B O4 3.0392 no . 2_656
H22B O8 2.4899 no . 2_656
H22B C18 3.2987 no . 2_656
H22B C21 3.0098 no . 2_656
H22B C30 3.1511 no . 2_656
H22B H37 3.5687 no . 2_656
H24A O5 2.4761 no . 2_545
H24A C38 3.1619 no . 2_545
H24A H28 3.4098 no . 2_445
H24A H37 3.2111 no . 2_545
H24B O7 3.1569 no . 2_555
H24B C16 3.2239 no . 1_455
H24B C31 3.2310 no . 1_455
H24B C36 3.4738 no . 1_455
H24B H28 3.1410 no . 2_445
H24B H31 3.2976 no . 1_455
H24B H31 3.5645 no . 2_555
H25 O5 2.7834 no . .
H25 O7 3.2806 no . 2_555
H25 C34 3.1424 no . 1_455
H25 H33A 3.1653 no . .
H25 H34 2.7028 no . 1_455
H28 O1 3.3944 no . 2_555
H28 O3 3.4654 no . 2_455
H28 O7 2.8641 no . 2_555
H28 C36 3.4249 no . 2_555
H28 C37 3.3346 no . 1_455
H28 H24A 3.4098 no . 2_455
H28 H24B 3.1410 no . 2_455
H28 H34 3.4584 no . 1_455
H28 H37 2.9537 no . 1_455
H31 O1 2.3764 no . 2_645
H31 O3 2.9944 no . 2_545
H31 C14 3.5735 no . 2_645
H31 C17 3.5069 no . 1_645
H31 C33 3.5550 no . 1_655
H31 H11 3.4751 no . 2_646
H31 H17 2.8992 no . 1_645
H31 H24B 3.2976 no . 1_655
H31 H24B 3.5645 no . 2_545
H31 H33B 2.7876 no . 1_655
H32A O6 2.7829 no . 2_646
H32A C29 3.4778 no . 1_655
H32A C35 3.3948 no . 1_655
H32A H35 3.1615 no . 2_646
H32B O8 2.7081 no . 2_656
H32B C18 3.3522 no . 2_656
H32B C35 3.4878 no . 1_655
H32B H34 3.4849 no . 2_756
H32B H35 3.3061 no . 1_655
H33A O7 2.5807 no . 2_555
H33A C20 3.3974 no . 1_455
H33A H20 3.4559 no . 1_455
H33A H25 3.1653 no . .
H33B O1 2.6077 no . 2_545
H33B O5 3.4083 no . 2_545
H33B N10 3.5349 no . 2_545
H33B C14 3.2349 no . 2_545
H33B C20 3.0148 no . 1_455
H33B C31 2.9450 no . 1_455
H33B H10 3.2705 no . 2_545
H33B H20 2.8784 no . 1_455
H33B H31 2.7876 no . 1_455
H34 O4 3.5948 no . 2_646
H34 O6 2.8677 no . 2_646
H34 C25 3.0790 no . 1_655
H34 C28 3.4960 no . 1_655
H34 H25 2.7028 no . 1_655
H34 H28 3.4584 no . 1_655
H34 H32B 3.4849 no . 2_746
H35 O2 3.1328 no . 2_656
H35 O4 2.5081 no . 2_556
H35 C23 3.5032 no . 2_656
H35 H20 3.1310 no . 1_465
H35 H22A 3.0975 no . 1_455
H35 H32A 3.1615 no . 2_656
H35 H32B 3.3061 no . 1_455
H37 O8 2.4350 no . .
H37 C18 3.2498 no . .
H37 C28 3.4580 no . 1_655
H37 H22B 3.5687 no . 2_646
H37 H24A 3.2111 no . 2_555
H37 H28 2.9537 no . 1_655

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N10 H10 O2 . . 1_454 2.933(9) 0.880 2.054 176.2 no
N11 H11 O3 . . 1_656 2.931(9) 0.880 2.110 154.8 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1009509'
#######################################################################
#
#                 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_20110309

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H9 F N2 O4'
_chemical_formula_moiety         'C13 H9 F N2 O4'
_chemical_formula_weight         276.22
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.24677(14)
_cell_length_b                   14.8112(3)
_cell_length_c                   11.0943(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.3083(12)
_cell_angle_gamma                90.0000
_cell_volume                     1175.11(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17970
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568.00
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_T_max  0.896

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18765
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2154
_reflns_number_gt                1947
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1031
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2154
_refine_ls_number_parameters     209
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0439P)²+0.3623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0326(15)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.38619(16) 0.73217(7) 0.74118(9) 0.0462(4) Uani 1.0 4 d . . .
O2 O 0.39171(17) 0.46769(8) 0.66449(11) 0.0392(4) Uani 1.0 4 d . . .
O3 O 0.16123(19) 0.67614(8) 0.90556(11) 0.0433(4) Uani 1.0 4 d . . .
O4 O 0.58100(17) 0.64214(9) 0.60252(11) 0.0447(4) Uani 1.0 4 d . . .
O5 O 0.07062(19) 0.57933(12) 0.32672(12) 0.0567(5) Uani 1.0 4 d . . .
N6 N 0.27983(18) 0.58948(8) 0.76165(11) 0.0273(4) Uani 1.0 4 d . . .
N7 N 0.3210(2) 0.61325(10) 0.46572(12) 0.0344(4) Uani 1.0 4 d . . .
C8 C 0.3352(2) 0.49912(10) 0.75205(14) 0.0279(4) Uani 1.0 4 d . . .
C9 C 0.3099(2) 0.45505(11) 0.86783(14) 0.0291(4) Uani 1.0 4 d . . .
C10 C 0.3421(3) 0.36685(12) 0.90502(17) 0.0383(5) Uani 1.0 4 d . . .
C11 C 0.3148(3) 0.34558(14) 1.02283(19) 0.0446(5) Uani 1.0 4 d . . .
C12 C 0.2577(3) 0.41037(14) 1.09977(17) 0.0439(5) Uani 1.0 4 d . . .
C13 C 0.2220(3) 0.49845(13) 1.06094(16) 0.0373(5) Uani 1.0 4 d . . .
C14 C 0.2489(2) 0.51929(11) 0.94314(14) 0.0290(4) Uani 1.0 4 d . . .
C15 C 0.2220(3) 0.60529(11) 0.87592(14) 0.0303(4) Uani 1.0 4 d . . .
C16 C 0.4132(3) 0.63629(11) 0.57908(14) 0.0322(4) Uani 1.0 4 d . . .
C17 C 0.2892(3) 0.66263(10) 0.67526(14) 0.0305(4) Uani 1.0 4 d . . .
C18 C 0.0989(3) 0.69577(12) 0.61746(16) 0.0376(5) Uani 1.0 4 d . . .
C19 C 0.0100(3) 0.62937(15) 0.52193(17) 0.0418(5) Uani 1.0 4 d . . .
C20 C 0.1307(3) 0.60577(12) 0.42859(15) 0.0369(4) Uani 1.0 4 d . . .
H21 H 0.382(3) 0.3215(12) 0.8486(16) 0.0278 Uiso 1.0 4 d . . .
H22 H 0.333(3) 0.2871(12) 1.0531(16) 0.0278 Uiso 1.0 4 d . . .
H23 H 0.241(3) 0.3956(11) 1.1813(17) 0.0278 Uiso 1.0 4 d . . .
H24 H 0.176(3) 0.5438(12) 1.1089(16) 0.0278 Uiso 1.0 4 d . . .
H25 H 0.392(3) 0.5987(12) 0.4134(17) 0.0278 Uiso 1.0 4 d . . .
H26 H 0.019(3) 0.7036(12) 0.6812(16) 0.0278 Uiso 1.0 4 d . . .
H27 H 0.116(3) 0.7549(12) 0.5799(16) 0.0278 Uiso 1.0 4 d . . .
H28 H -0.012(3) 0.5737(12) 0.5575(17) 0.0278 Uiso 1.0 4 d . . .
H29 H -0.103(3) 0.6489(12) 0.4772(16) 0.0278 Uiso 1.0 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C17 1.3868(18) yes . .
O2 C8 1.207(2) yes . .
O3 C15 1.204(2) yes . .
O4 C16 1.205(2) yes . .
O5 C20 1.209(2) yes . .
N6 C8 1.406(2) yes . .
N6 C15 1.418(2) yes . .
N6 C17 1.455(2) yes . .
N7 C16 1.368(2) yes . .
N7 C20 1.379(3) yes . .
C8 C9 1.479(3) yes . .
C9 C10 1.378(3) yes . .
C9 C14 1.385(3) yes . .
C10 C11 1.389(3) yes . .
C11 C12 1.391(3) yes . .
C12 C13 1.385(3) yes . .
C13 C14 1.387(3) yes . .
C14 C15 1.473(3) yes . .
C16 C17 1.552(3) yes . .
C17 C18 1.506(3) yes . .
C18 C19 1.512(3) yes . .
C19 C20 1.501(3) yes . .
N7 H25 0.86(2) no . .
C10 H21 0.993(18) no . .
C11 H22 0.931(18) no . .
C12 H23 0.958(19) no . .
C13 H24 0.950(19) no . .
C18 H26 0.990(19) no . .
C18 H27 0.987(18) no . .
C19 H28 0.939(19) no . .
C19 H29 0.929(17) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C8 N6 C15 110.75(13) yes . . .
C8 N6 C17 127.90(14) yes . . .
C15 N6 C17 121.20(13) yes . . .
C16 N7 C20 127.65(16) yes . . .
O2 C8 N6 124.49(15) yes . . .
O2 C8 C9 129.42(15) yes . . .
N6 C8 C9 106.10(14) yes . . .
C8 C9 C10 129.76(16) yes . . .
C8 C9 C14 108.51(14) yes . . .
C10 C9 C14 121.71(16) yes . . .
C9 C10 C11 116.97(18) yes . . .
C10 C11 C12 121.51(19) yes . . .
C11 C12 C13 121.21(19) yes . . .
C12 C13 C14 117.06(17) yes . . .
C9 C14 C13 121.52(16) yes . . .
C9 C14 C15 108.52(14) yes . . .
C13 C14 C15 129.96(16) yes . . .
O3 C15 N6 124.21(15) yes . . .
O3 C15 C14 129.76(16) yes . . .
N6 C15 C14 106.02(14) yes . . .
O4 C16 N7 122.82(16) yes . . .
O4 C16 C17 120.66(14) yes . . .
N7 C16 C17 116.34(14) yes . . .
F1 C17 N6 106.22(12) yes . . .
F1 C17 C16 104.42(13) yes . . .
F1 C17 C18 109.48(13) yes . . .
N6 C17 C16 111.08(13) yes . . .
N6 C17 C18 112.69(14) yes . . .
C16 C17 C18 112.42(13) yes . . .
C17 C18 C19 110.11(15) yes . . .
C18 C19 C20 113.91(16) yes . . .
O5 C20 N7 119.79(17) yes . . .
O5 C20 C19 123.96(16) yes . . .
N7 C20 C19 116.22(14) yes . . .
C16 N7 H25 115.1(11) no . . .
C20 N7 H25 117.1(11) no . . .
C9 C10 H21 120.3(10) no . . .
C11 C10 H21 122.7(10) no . . .
C10 C11 H22 121.1(12) no . . .
C12 C11 H22 117.4(12) no . . .
C11 C12 H23 121.2(10) no . . .
C13 C12 H23 117.6(10) no . . .
C12 C13 H24 123.8(11) no . . .
C14 C13 H24 119.0(11) no . . .
C17 C18 H26 109.5(10) no . . .
C17 C18 H27 107.4(10) no . . .
C19 C18 H26 110.2(10) no . . .
C19 C18 H27 110.5(10) no . . .
H26 C18 H27 109.1(15) no . . .
C18 C19 H28 111.0(11) no . . .
C18 C19 H29 114.2(11) no . . .
C20 C19 H28 104.2(12) no . . .
C20 C19 H29 105.2(12) no . . .
H28 C19 H29 107.5(15) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C8 N6 C15 O3 -177.09(13) no . . . .
C8 N6 C15 C14 1.76(15) no . . . .
C15 N6 C8 O2 -179.56(13) no . . . .
C15 N6 C8 C9 0.23(15) no . . . .
C8 N6 C17 F1 -126.31(14) no . . . .
C8 N6 C17 C16 -13.35(19) no . . . .
C8 N6 C17 C18 113.82(15) no . . . .
C17 N6 C8 O2 -4.0(3) no . . . .
C17 N6 C8 C9 175.74(12) no . . . .
C15 N6 C17 F1 48.78(18) no . . . .
C15 N6 C17 C16 161.74(12) no . . . .
C15 N6 C17 C18 -71.09(16) no . . . .
C17 N6 C15 O3 7.1(3) no . . . .
C17 N6 C15 C14 -174.10(11) no . . . .
C16 N7 C20 O5 -175.53(15) no . . . .
C16 N7 C20 C19 2.8(3) no . . . .
C20 N7 C16 O4 -179.07(15) no . . . .
C20 N7 C16 C17 -3.9(3) no . . . .
O2 C8 C9 C10 -0.8(3) no . . . .
O2 C8 C9 C14 177.49(15) no . . . .
N6 C8 C9 C10 179.44(13) no . . . .
N6 C8 C9 C14 -2.28(15) no . . . .
C8 C9 C10 C11 176.62(13) no . . . .
C8 C9 C14 C13 -176.73(12) no . . . .
C8 C9 C14 C15 3.37(16) no . . . .
C10 C9 C14 C13 1.7(3) no . . . .
C10 C9 C14 C15 -178.18(13) no . . . .
C14 C9 C10 C11 -1.5(3) no . . . .
C9 C10 C11 C12 -0.1(3) no . . . .
C10 C11 C12 C13 1.4(3) no . . . .
C11 C12 C13 C14 -1.1(3) no . . . .
C12 C13 C14 C9 -0.4(3) no . . . .
C12 C13 C14 C15 179.51(14) no . . . .
C9 C14 C15 O3 175.57(15) no . . . .
C9 C14 C15 N6 -3.19(16) no . . . .
C13 C14 C15 O3 -4.3(3) no . . . .
C13 C14 C15 N6 176.92(15) no . . . .
O4 C16 C17 F1 32.61(19) no . . . .
O4 C16 C17 N6 -81.49(18) no . . . .
O4 C16 C17 C18 151.20(14) no . . . .
N7 C16 C17 F1 -142.63(13) no . . . .
N7 C16 C17 N6 103.28(15) no . . . .
N7 C16 C17 C18 -24.04(19) no . . . .
F1 C17 C18 C19 166.42(12) no . . . .
N6 C17 C18 C19 -75.61(16) no . . . .
C16 C17 C18 C19 50.84(18) no . . . .
C17 C18 C19 C20 -52.9(2) no . . . .
C18 C19 C20 O5 -155.18(16) no . . . .
C18 C19 C20 N7 26.6(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 O3 2.7630(18) no . .
F1 O4 2.6154(18) no . .
F1 N7 3.4925(17) no . .
F1 C8 3.4756(19) no . .
F1 C15 2.785(2) no . .
O2 O4 3.0554(18) no . .
O2 N7 3.0672(19) no . .
O2 C10 3.129(3) no . .
O2 C14 3.500(2) no . .
O2 C15 3.479(2) no . .
O2 C16 2.684(2) no . .
O2 C17 2.988(2) no . .
O3 C8 3.473(2) no . .
O3 C9 3.494(2) no . .
O3 C13 3.138(3) no . .
O3 C17 2.863(3) no . .
O3 C18 3.168(3) no . .
O4 N6 3.1201(19) no . .
O4 C8 3.371(2) no . .
O4 C20 3.553(2) no . .
O5 C16 3.531(2) no . .
N6 N7 3.3629(19) no . .
N6 C19 3.093(2) no . .
N7 C8 3.585(2) no . .
N7 C18 2.792(3) no . .
C8 C16 2.912(3) no . .
C8 C18 3.580(3) no . .
C9 C12 2.742(3) no . .
C10 C13 2.835(3) no . .
C11 C14 2.737(3) no . .
C15 C18 3.160(3) no . .
C16 C19 2.890(3) no . .
C17 C20 2.916(3) no . .
F1 N7 3.4715(18) no . 4_565
F1 C10 3.394(3) no . 2_656
F1 C11 3.323(3) no . 3_667
F1 C12 3.572(2) no . 3_667
O2 O4 3.4132(18) no . 3_666
O2 O5 3.4388(19) no . 3_566
O2 N7 2.972(2) no . 3_666
O2 C16 3.593(3) no . 3_666
O2 C19 3.587(3) no . 3_566
O3 N7 3.3566(19) no . 4_565
O3 C12 3.287(3) no . 3_567
O3 C18 3.110(3) no . 4_565
O3 C19 3.409(3) no . 4_565
O3 C20 3.251(3) no . 4_565
O4 O2 3.4132(18) no . 3_666
O4 C10 3.378(3) no . 2_656
O4 C11 3.453(3) no . 2_656
O4 C12 3.410(3) no . 3_667
O4 C19 3.376(3) no . 1_655
O5 O2 3.4388(19) no . 3_566
O5 N6 3.586(2) no . 3_566
O5 C8 3.152(2) no . 3_566
O5 C9 3.2552(19) no . 3_566
O5 C13 3.518(3) no . 1_554
N6 O5 3.586(2) no . 3_566
N6 C12 3.454(2) no . 3_667
N7 F1 3.4715(18) no . 4_564
N7 O2 2.972(2) no . 3_666
N7 O3 3.3566(19) no . 4_564
C8 O5 3.152(2) no . 3_566
C8 C12 3.410(3) no . 3_667
C8 C13 3.528(3) no . 3_667
C9 O5 3.2552(19) no . 3_566
C9 C13 3.426(3) no . 3_667
C9 C14 3.549(2) no . 3_667
C10 F1 3.394(3) no . 2_646
C10 O4 3.378(3) no . 2_646
C10 C14 3.585(3) no . 3_667
C11 F1 3.323(3) no . 3_667
C11 O4 3.453(3) no . 2_646
C11 C15 3.441(3) no . 3_667
C12 F1 3.572(2) no . 3_667
C12 O3 3.287(3) no . 3_567
C12 O4 3.410(3) no . 3_667
C12 N6 3.454(2) no . 3_667
C12 C8 3.410(3) no . 3_667
C12 C15 3.538(3) no . 3_567
C13 O5 3.518(3) no . 1_556
C13 C8 3.528(3) no . 3_667
C13 C9 3.426(3) no . 3_667
C13 C13 3.282(3) no . 3_567
C13 C14 3.415(3) no . 3_567
C14 C9 3.549(2) no . 3_667
C14 C10 3.585(3) no . 3_667
C14 C13 3.415(3) no . 3_567
C15 C11 3.441(3) no . 3_667
C15 C12 3.538(3) no . 3_567
C16 O2 3.593(3) no . 3_666
C18 O3 3.110(3) no . 4_564
C19 O2 3.587(3) no . 3_566
C19 O3 3.409(3) no . 4_564
C19 O4 3.376(3) no . 1_455
C20 O3 3.251(3) no . 4_564
F1 H26 2.669(17) no . .
F1 H27 2.452(16) no . .
O2 H21 2.985(18) no . .
O2 H25 3.395(18) no . .
O2 H28 3.366(17) no . .
O3 H24 2.977(18) no . .
O3 H26 2.567(17) no . .
O4 H25 2.400(17) no . .
O5 H25 2.390(17) no . .
O5 H28 2.725(19) no . .
O5 H29 2.470(19) no . .
N6 H26 2.583(17) no . .
N6 H27 3.272(17) no . .
N6 H28 2.849(17) no . .
N7 H27 2.970(18) no . .
N7 H28 2.831(19) no . .
N7 H29 3.137(19) no . .
C8 H21 2.840(17) no . .
C8 H28 3.235(17) no . .
C9 H22 3.213(18) no . .
C9 H24 3.265(19) no . .
C10 H23 3.293(19) no . .
C11 H24 3.295(18) no . .
C12 H21 3.335(18) no . .
C13 H22 3.237(18) no . .
C14 H21 3.308(18) no . .
C14 H23 3.224(18) no . .
C15 H24 2.810(19) no . .
C15 H26 2.814(16) no . .
C16 H26 3.388(18) no . .
C16 H27 2.780(17) no . .
C16 H28 3.193(17) no . .
C17 H25 3.255(19) no . .
C17 H28 2.701(17) no . .
C17 H29 3.303(17) no . .
C19 H25 3.226(19) no . .
C20 H26 3.368(18) no . .
C20 H27 2.787(18) no . .
H21 H22 2.41(3) no . .
H22 H23 2.32(3) no . .
H23 H24 2.36(3) no . .
H25 H28 3.58(3) no . .
H26 H28 2.35(3) no . .
H26 H29 2.43(3) no . .
H27 H28 2.84(3) no . .
H27 H29 2.39(3) no . .
F1 H21 2.470(18) no . 2_656
F1 H22 2.814(16) no . 3_667
F1 H23 3.296(16) no . 3_667
F1 H25 3.147(18) no . 4_565
O2 H23 3.555(16) no . 3_667
O2 H25 2.146(19) no . 3_666
O2 H28 3.436(16) no . 3_566
O2 H29 2.963(17) no . 3_566
O3 H23 3.106(16) no . 3_567
O3 H27 2.257(18) no . 4_565
O3 H29 3.390(18) no . 4_565
O4 H21 2.715(17) no . 2_656
O4 H22 2.885(18) no . 2_656
O4 H23 2.593(17) no . 3_667
O4 H25 3.578(17) no . 3_666
O4 H26 3.283(17) no . 1_655
O4 H28 3.230(18) no . 1_655
O4 H29 2.87(2) no . 1_655
O5 H23 3.490(18) no . 1_554
O5 H24 2.701(19) no . 1_554
O5 H26 3.590(17) no . 4_564
O5 H28 2.672(19) no . 3_566
N6 H23 3.434(17) no . 3_667
N7 H28 3.543(18) no . 3_566
C8 H23 3.416(17) no . 3_667
C8 H25 3.247(19) no . 3_666
C8 H29 3.568(17) no . 3_566
C9 H24 3.572(18) no . 3_567
C10 H26 3.579(17) no . 2_546
C11 H27 3.421(16) no . 2_546
C11 H29 3.295(18) no . 2_546
C13 H24 3.240(16) no . 3_567
C14 H24 3.180(17) no . 3_567
C15 H22 3.567(17) no . 3_667
C15 H23 3.313(17) no . 3_567
C15 H27 3.249(18) no . 4_565
C16 H21 3.159(17) no . 2_656
C16 H22 3.374(18) no . 2_656
C16 H23 3.378(16) no . 3_667
C17 H21 3.388(17) no . 2_656
C19 H22 3.416(17) no . 2_556
C19 H28 3.136(18) no . 3_566
C20 H28 2.805(18) no . 3_566
H21 F1 2.470(18) no . 2_646
H21 O4 2.715(17) no . 2_646
H21 C16 3.159(17) no . 2_646
H21 C17 3.388(17) no . 2_646
H21 H26 3.36(3) no . 2_546
H22 F1 2.814(16) no . 3_667
H22 O4 2.885(18) no . 2_646
H22 C15 3.567(17) no . 3_667
H22 C16 3.374(18) no . 2_646
H22 C19 3.416(17) no . 2_546
H22 H25 3.41(3) no . 2_646
H22 H26 3.56(3) no . 2_546
H22 H27 3.38(3) no . 2_546
H22 H29 2.63(3) no . 2_546
H23 F1 3.296(16) no . 3_667
H23 O2 3.555(16) no . 3_667
H23 O3 3.106(16) no . 3_567
H23 O4 2.593(17) no . 3_667
H23 O5 3.490(18) no . 1_556
H23 N6 3.434(17) no . 3_667
H23 C8 3.416(17) no . 3_667
H23 C15 3.313(17) no . 3_567
H23 C16 3.378(16) no . 3_667
H23 H26 3.00(3) no . 3_567
H23 H28 3.59(3) no . 3_567
H24 O5 2.701(19) no . 1_556
H24 C9 3.572(18) no . 3_567
H24 C13 3.240(16) no . 3_567
H24 C14 3.180(17) no . 3_567
H24 H24 3.47(3) no . 3_567
H24 H25 3.58(3) no . 1_556
H24 H27 3.02(3) no . 4_565
H25 F1 3.147(18) no . 4_564
H25 O2 2.146(19) no . 3_666
H25 O4 3.578(17) no . 3_666
H25 C8 3.247(19) no . 3_666
H25 H22 3.41(3) no . 2_656
H25 H24 3.58(3) no . 1_554
H26 O4 3.283(17) no . 1_455
H26 O5 3.590(17) no . 4_565
H26 C10 3.579(17) no . 2_556
H26 H21 3.36(3) no . 2_556
H26 H22 3.56(3) no . 2_556
H26 H23 3.00(3) no . 3_567
H27 O3 2.257(18) no . 4_564
H27 C11 3.421(16) no . 2_556
H27 C15 3.249(18) no . 4_564
H27 H22 3.38(3) no . 2_556
H27 H24 3.02(3) no . 4_564
H28 O2 3.436(16) no . 3_566
H28 O4 3.230(18) no . 1_455
H28 O5 2.672(19) no . 3_566
H28 N7 3.543(18) no . 3_566
H28 C19 3.136(18) no . 3_566
H28 C20 2.805(18) no . 3_566
H28 H23 3.59(3) no . 3_567
H28 H28 2.55(3) no . 3_566
H28 H29 3.44(3) no . 3_566
H29 O2 2.963(17) no . 3_566
H29 O3 3.390(18) no . 4_564
H29 O4 2.87(2) no . 1_455
H29 C8 3.568(17) no . 3_566
H29 C11 3.295(18) no . 2_556
H29 H22 2.63(3) no . 2_556
H29 H28 3.44(3) no . 3_566

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N7 H25 O2 . . 3_666 2.972(2) 0.863 2.15(2) 159.9(16) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1009506'
#######################################################################
#
#                 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_20110303

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H9 F N2 O4'
_chemical_formula_moiety         'C13 H9 F N2 O4'
_chemical_formula_weight         276.22
_chemical_melting_point          ?
_chemical_absolute_configuration ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.1667(4)
_cell_length_b                   5.2718(3)
_cell_length_c                   15.7374(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.260(3)
_cell_angle_gamma                90.0000
_cell_volume                     583.14(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4232
_cell_measurement_theta_min      5.74
_cell_measurement_theta_max      67.94
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284.00
_exptl_absorpt_coefficient_mu    1.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  0.895

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6166
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_full        68.17
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2030
_reflns_number_gt                1645
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1047
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2030
_refine_ls_number_parameters     209
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0395P)²+0.2544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0114(12)
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  844 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.0(3)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.3541(3) 1.3703(3) 0.25155(10) 0.0380(5) Uani 1.0 2 d . . .
O2 O 0.6930(3) 0.9277(5) 0.15656(13) 0.0411(6) Uani 1.0 2 d . . .
O3 O 0.3382(3) 0.9355(5) 0.36937(12) 0.0484(7) Uani 1.0 2 d . . .
O4 O 0.4920(3) 1.4266(4) 0.11131(13) 0.0388(6) Uani 1.0 2 d . . .
O5 O 0.1393(4) 0.7902(6) -0.02905(15) 0.0583(8) Uani 1.0 2 d . . .
N6 N 0.4793(4) 0.9718(5) 0.24846(14) 0.0296(6) Uani 1.0 2 d . . .
N7 N 0.3267(4) 1.0906(6) 0.04455(16) 0.0351(7) Uani 1.0 2 d . . .
C8 C 0.6444(4) 0.8740(6) 0.22288(18) 0.0302(7) Uani 1.0 2 d . . .
C9 C 0.7328(5) 0.7050(6) 0.29423(19) 0.0337(8) Uani 1.0 2 d . . .
C10 C 0.8909(5) 0.5510(7) 0.3011(3) 0.0426(9) Uani 1.0 2 d . . .
C11 C 0.9404(6) 0.4018(8) 0.3749(3) 0.0499(10) Uani 1.0 2 d . . .
C12 C 0.8345(6) 0.4108(8) 0.4395(3) 0.0506(10) Uani 1.0 2 d . . .
C13 C 0.6761(5) 0.5656(7) 0.4323(2) 0.0435(9) Uani 1.0 2 d . . .
C14 C 0.6291(5) 0.7114(6) 0.35887(19) 0.0354(8) Uani 1.0 2 d . . .
C15 C 0.4625(5) 0.8814(7) 0.33136(17) 0.0346(8) Uani 1.0 2 d . . .
C16 C 0.3996(5) 1.2371(6) 0.11502(19) 0.0304(7) Uani 1.0 2 d . . .
C17 C 0.3451(5) 1.1521(6) 0.20097(18) 0.0285(7) Uani 1.0 2 d . . .
C18 C 0.1406(5) 1.0573(7) 0.1837(2) 0.0305(7) Uani 1.0 2 d . . .
C19 C 0.1198(5) 0.8379(7) 0.11971(19) 0.0318(7) Uani 1.0 2 d . . .
C20 C 0.1928(4) 0.8984(7) 0.03870(18) 0.0344(8) Uani 1.0 2 d . . .
H21 H 0.947(5) 0.544(6) 0.2533(19) 0.0319 Uiso 1.0 2 d . . .
H22 H 1.049(5) 0.299(6) 0.3815(19) 0.0319 Uiso 1.0 2 d . . .
H23 H 0.860(5) 0.306(6) 0.4932(19) 0.0319 Uiso 1.0 2 d . . .
H24 H 0.590(5) 0.567(6) 0.474(2) 0.0319 Uiso 1.0 2 d . . .
H25 H 0.112(4) 1.011(6) 0.239(2) 0.0319 Uiso 1.0 2 d . . .
H26 H 0.073(5) 1.193(7) 0.158(2) 0.0319 Uiso 1.0 2 d . . .
H27 H -0.018(5) 0.800(6) 0.1001(18) 0.0319 Uiso 1.0 2 d . . .
H28 H 0.203(5) 0.696(7) 0.1451(19) 0.0319 Uiso 1.0 2 d . . .
H29 H 0.356(5) 1.137(6) -0.002(2) 0.0319 Uiso 1.0 2 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C17 1.393(4) yes . .
O2 C8 1.197(4) yes . .
O3 C15 1.201(4) yes . .
O4 C16 1.206(4) yes . .
O5 C20 1.204(4) yes . .
N6 C8 1.419(4) yes . .
N6 C15 1.416(4) yes . .
N6 C17 1.451(4) yes . .
N7 C16 1.369(4) yes . .
N7 C20 1.386(5) yes . .
C8 C9 1.476(4) yes . .
C9 C10 1.381(5) yes . .
C9 C14 1.372(5) yes . .
C10 C11 1.390(5) yes . .
C11 C12 1.384(6) yes . .
C12 C13 1.384(6) yes . .
C13 C14 1.374(5) yes . .
C14 C15 1.488(5) yes . .
C16 C17 1.546(5) yes . .
C17 C18 1.522(5) yes . .
C18 C19 1.522(5) yes . .
C19 C20 1.504(5) yes . .
N7 H29 0.83(4) no . .
C10 H21 0.92(4) no . .
C11 H22 0.94(4) no . .
C12 H23 1.00(3) no . .
C13 H24 0.98(4) no . .
C18 H25 0.97(4) no . .
C18 H26 0.91(4) no . .
C19 H27 1.00(3) no . .
C19 H28 0.99(4) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C8 N6 C15 111.4(3) yes . . .
C8 N6 C17 126.7(3) yes . . .
C15 N6 C17 121.9(3) yes . . .
C16 N7 C20 128.0(3) yes . . .
O2 C8 N6 124.2(3) yes . . .
O2 C8 C9 130.7(3) yes . . .
N6 C8 C9 105.1(3) yes . . .
C8 C9 C10 129.7(3) yes . . .
C8 C9 C14 109.6(3) yes . . .
C10 C9 C14 120.7(3) yes . . .
C9 C10 C11 118.1(4) yes . . .
C10 C11 C12 120.5(4) yes . . .
C11 C12 C13 121.2(4) yes . . .
C12 C13 C14 117.5(4) yes . . .
C9 C14 C13 122.0(3) yes . . .
C9 C14 C15 108.6(3) yes . . .
C13 C14 C15 129.2(4) yes . . .
O3 C15 N6 125.7(3) yes . . .
O3 C15 C14 129.0(3) yes . . .
N6 C15 C14 105.3(3) yes . . .
O4 C16 N7 123.7(3) yes . . .
O4 C16 C17 121.2(3) yes . . .
N7 C16 C17 115.1(3) yes . . .
F1 C17 N6 107.1(2) yes . . .
F1 C17 C16 105.6(3) yes . . .
F1 C17 C18 108.0(3) yes . . .
N6 C17 C16 112.7(3) yes . . .
N6 C17 C18 113.3(3) yes . . .
C16 C17 C18 109.7(3) yes . . .
C17 C18 C19 109.5(3) yes . . .
C18 C19 C20 113.2(3) yes . . .
O5 C20 N7 120.1(3) yes . . .
O5 C20 C19 123.1(3) yes . . .
N7 C20 C19 116.7(3) yes . . .
C16 N7 H29 115(2) no . . .
C20 N7 H29 116(2) no . . .
C9 C10 H21 116.3(19) no . . .
C11 C10 H21 125.4(19) no . . .
C10 C11 H22 119.4(19) no . . .
C12 C11 H22 120.1(19) no . . .
C11 C12 H23 124.6(19) no . . .
C13 C12 H23 114.1(19) no . . .
C12 C13 H24 124.4(18) no . . .
C14 C13 H24 117.9(18) no . . .
C17 C18 H25 106.6(17) no . . .
C17 C18 H26 103(2) no . . .
C19 C18 H25 113.3(19) no . . .
C19 C18 H26 109(2) no . . .
H25 C18 H26 115(3) no . . .
C18 C19 H27 108.6(18) no . . .
C18 C19 H28 109.5(18) no . . .
C20 C19 H27 105.6(17) no . . .
C20 C19 H28 103(2) no . . .
H27 C19 H28 117(3) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C8 N6 C15 O3 179.1(3) no . . . .
C8 N6 C15 C14 -0.8(3) no . . . .
C15 N6 C8 O2 -177.8(3) no . . . .
C15 N6 C8 C9 1.7(3) no . . . .
C8 N6 C17 F1 -116.2(3) no . . . .
C8 N6 C17 C16 -0.4(4) no . . . .
C8 N6 C17 C18 124.9(3) no . . . .
C17 N6 C8 O2 -1.0(5) no . . . .
C17 N6 C8 C9 178.5(3) no . . . .
C15 N6 C17 F1 60.4(4) no . . . .
C15 N6 C17 C16 176.1(3) no . . . .
C15 N6 C17 C18 -58.6(4) no . . . .
C17 N6 C15 O3 2.1(5) no . . . .
C17 N6 C15 C14 -177.8(3) no . . . .
C16 N7 C20 O5 178.2(3) no . . . .
C16 N7 C20 C19 -1.2(5) no . . . .
C20 N7 C16 O4 -167.5(3) no . . . .
C20 N7 C16 C17 8.9(5) no . . . .
O2 C8 C9 C10 -4.3(6) no . . . .
O2 C8 C9 C14 177.5(3) no . . . .
N6 C8 C9 C10 176.2(3) no . . . .
N6 C8 C9 C14 -2.1(3) no . . . .
C8 C9 C10 C11 -177.6(3) no . . . .
C8 C9 C14 C13 178.0(3) no . . . .
C8 C9 C14 C15 1.6(4) no . . . .
C10 C9 C14 C13 -0.4(5) no . . . .
C10 C9 C14 C15 -176.8(3) no . . . .
C14 C9 C10 C11 0.5(5) no . . . .
C9 C10 C11 C12 -0.6(5) no . . . .
C10 C11 C12 C13 0.6(6) no . . . .
C11 C12 C13 C14 -0.5(5) no . . . .
C12 C13 C14 C9 0.4(5) no . . . .
C12 C13 C14 C15 176.0(3) no . . . .
C9 C14 C15 O3 179.6(3) no . . . .
C9 C14 C15 N6 -0.6(4) no . . . .
C13 C14 C15 O3 3.6(6) no . . . .
C13 C14 C15 N6 -176.6(3) no . . . .
O4 C16 C17 F1 22.7(4) no . . . .
O4 C16 C17 N6 -93.9(4) no . . . .
O4 C16 C17 C18 138.9(3) no . . . .
N7 C16 C17 F1 -153.8(3) no . . . .
N7 C16 C17 N6 89.6(3) no . . . .
N7 C16 C17 C18 -37.6(4) no . . . .
F1 C17 C18 C19 173.22(19) no . . . .
N6 C17 C18 C19 -68.3(3) no . . . .
C16 C17 C18 C19 58.6(3) no . . . .
C17 C18 C19 C20 -52.1(3) no . . . .
C18 C19 C20 O5 -156.1(3) no . . . .
C18 C19 C20 N7 23.2(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 O3 2.964(3) no . .
F1 O4 2.605(3) no . .
F1 N7 3.546(3) no . .
F1 C8 3.427(4) no . .
F1 C15 2.906(4) no . .
O2 O4 3.016(4) no . .
O2 N7 2.988(3) no . .
O2 C10 3.142(4) no . .
O2 C14 3.495(4) no . .
O2 C15 3.483(4) no . .
O2 C16 2.640(4) no . .
O2 C17 2.964(4) no . .
O3 C8 3.495(4) no . .
O3 C9 3.490(4) no . .
O3 C13 3.117(5) no . .
O3 C17 2.895(4) no . .
O3 C18 3.057(4) no . .
O4 N6 3.239(4) no . .
O4 C8 3.466(4) no . .
O4 C18 3.542(4) no . .
O4 C20 3.563(4) no . .
O5 C16 3.539(4) no . .
N6 N7 3.243(4) no . .
N6 C19 3.034(4) no . .
N6 C20 3.552(4) no . .
N7 C8 3.445(4) no . .
N7 C18 2.783(5) no . .
C8 C16 2.909(4) no . .
C9 C12 2.742(5) no . .
C10 C13 2.807(6) no . .
C11 C14 2.736(5) no . .
C15 C18 3.081(4) no . .
C16 C19 2.918(5) no . .
C17 C20 2.901(4) no . .
F1 O3 3.523(3) no . 1_565
F1 N6 3.298(3) no . 1_565
F1 C8 3.457(4) no . 1_565
F1 C9 3.197(4) no . 1_565
F1 C13 3.452(4) no . 1_565
F1 C14 2.944(4) no . 1_565
F1 C15 3.010(4) no . 1_565
F1 C19 3.441(4) no . 1_565
O2 O4 3.027(4) no . 1_545
O2 O5 3.173(4) no . 2_655
O2 C18 3.226(4) no . 1_655
O2 C19 3.257(4) no . 1_655
O3 F1 3.523(3) no . 1_545
O3 C12 3.471(5) no . 2_656
O3 C13 3.217(4) no . 2_656
O4 O2 3.027(4) no . 1_565
O4 O5 3.573(4) no . 1_565
O4 O5 3.243(4) no . 2_655
O4 N7 3.114(4) no . 2_655
O4 C8 3.015(4) no . 1_565
O4 C9 3.388(4) no . 1_565
O4 C19 3.460(4) no . 1_565
O4 C20 3.337(4) no . 1_565
O4 C20 3.575(4) no . 2_655
O5 O2 3.173(4) no . 2_645
O5 O4 3.573(4) no . 1_545
O5 O4 3.243(4) no . 2_645
O5 O5 3.533(4) no . 2_545
O5 O5 3.533(4) no . 2_555
O5 N7 3.464(4) no . 2_545
O5 C18 3.089(4) no . 2_545
O5 C19 3.183(5) no . 2_545
O5 C19 3.575(5) no . 2_555
O5 C20 3.132(5) no . 2_545
N6 F1 3.298(3) no . 1_545
N7 O4 3.114(4) no . 2_645
N7 O5 3.464(4) no . 2_555
C8 F1 3.457(4) no . 1_545
C8 O4 3.015(4) no . 1_545
C9 F1 3.197(4) no . 1_545
C9 O4 3.388(4) no . 1_545
C12 O3 3.471(5) no . 2_646
C13 F1 3.452(4) no . 1_545
C13 O3 3.217(4) no . 2_646
C14 F1 2.944(4) no . 1_545
C15 F1 3.010(4) no . 1_545
C18 O2 3.226(4) no . 1_455
C18 O5 3.089(4) no . 2_555
C19 F1 3.441(4) no . 1_545
C19 O2 3.257(4) no . 1_455
C19 O4 3.460(4) no . 1_545
C19 O5 3.575(5) no . 2_545
C19 O5 3.183(5) no . 2_555
C20 O4 3.337(4) no . 1_545
C20 O4 3.575(4) no . 2_645
C20 O5 3.132(5) no . 2_555
F1 H25 2.55(3) no . .
F1 H26 2.44(3) no . .
O2 H21 2.94(3) no . .
O2 H29 3.30(3) no . .
O3 H24 2.92(3) no . .
O3 H25 2.38(3) no . .
O4 H26 3.45(4) no . .
O4 H29 2.40(3) no . .
O5 H27 2.51(4) no . .
O5 H28 2.73(3) no . .
O5 H29 2.38(3) no . .
N6 H25 2.61(3) no . .
N6 H26 3.20(3) no . .
N6 H28 2.73(3) no . .
N7 H26 2.83(4) no . .
N7 H27 3.17(4) no . .
N7 H28 2.86(4) no . .
C8 H21 2.75(3) no . .
C8 H28 3.30(3) no . .
C9 H22 3.22(3) no . .
C9 H24 3.27(4) no . .
C10 H23 3.33(4) no . .
C11 H24 3.32(4) no . .
C12 H21 3.26(4) no . .
C13 H22 3.25(4) no . .
C14 H21 3.20(4) no . .
C14 H23 3.23(3) no . .
C15 H24 2.79(3) no . .
C15 H25 2.73(3) no . .
C15 H28 3.30(3) no . .
C16 H25 3.32(4) no . .
C16 H26 2.57(4) no . .
C16 H28 3.26(4) no . .
C17 H27 3.34(3) no . .
C17 H28 2.69(4) no . .
C17 H29 3.21(4) no . .
C18 H29 3.58(4) no . .
C19 H29 3.21(4) no . .
C20 H25 3.37(4) no . .
C20 H26 2.70(4) no . .
H21 H22 2.39(4) no . .
H22 H23 2.42(5) no . .
H23 H24 2.35(5) no . .
H25 H27 2.47(4) no . .
H25 H28 2.40(5) no . .
H26 H27 2.30(5) no . .
H26 H28 2.80(5) no . .
H26 H29 3.53(5) no . .
H28 H29 3.60(5) no . .
F1 H21 3.06(4) no . 1_465
F1 H22 3.29(4) no . 1_465
F1 H28 2.49(3) no . 1_565
O2 H25 3.06(3) no . 1_655
O2 H26 3.06(4) no . 1_655
O2 H27 2.50(4) no . 1_655
O2 H29 2.84(4) no . 2_645
O3 H22 2.86(4) no . 1_465
O3 H23 2.89(4) no . 2_656
O3 H24 2.52(3) no . 2_656
O4 H28 2.65(4) no . 1_565
O4 H29 2.48(4) no . 2_655
O5 H26 2.34(3) no . 2_545
O5 H27 2.88(3) no . 2_545
O5 H27 2.97(3) no . 2_555
O5 H28 3.49(3) no . 2_555
N7 H27 3.05(3) no . 2_555
N7 H29 3.45(4) no . 2_645
C8 H25 3.39(3) no . 1_655
C8 H27 3.40(4) no . 1_655
C9 H25 3.42(4) no . 1_655
C10 H25 3.49(4) no . 1_645
C10 H25 3.15(4) no . 1_655
C10 H26 3.39(4) no . 1_645
C10 H27 3.60(3) no . 1_655
C11 H23 3.12(3) no . 2_756
C11 H25 3.37(4) no . 1_645
C12 H22 3.45(3) no . 2_756
C12 H23 3.06(3) no . 2_756
C13 H22 3.42(3) no . 2_756
C13 H23 3.54(3) no . 2_756
C15 H24 3.31(4) no . 2_656
C16 H28 2.88(4) no . 1_565
C16 H29 3.45(4) no . 2_655
C17 H28 3.11(4) no . 1_565
C18 H21 3.32(4) no . 1_455
C18 H21 3.21(4) no . 1_465
C18 H22 3.54(3) no . 1_465
C18 H28 3.46(4) no . 1_565
C19 H21 3.06(4) no . 1_455
C19 H26 3.48(4) no . 1_545
C20 H26 3.47(3) no . 2_545
C20 H27 3.12(3) no . 2_555
H21 F1 3.06(4) no . 1_645
H21 C18 3.21(4) no . 1_645
H21 C18 3.32(4) no . 1_655
H21 C19 3.06(4) no . 1_655
H21 H25 3.08(5) no . 1_645
H21 H25 2.76(5) no . 1_655
H21 H26 2.65(5) no . 1_645
H21 H27 2.82(5) no . 1_655
H21 H28 2.85(5) no . 1_655
H22 F1 3.29(4) no . 1_645
H22 O3 2.86(4) no . 1_645
H22 C12 3.45(3) no . 2_746
H22 C13 3.42(3) no . 2_746
H22 C18 3.54(3) no . 1_645
H22 H23 3.25(5) no . 2_746
H22 H23 3.31(5) no . 2_756
H22 H24 3.33(4) no . 2_746
H22 H25 2.82(5) no . 1_645
H23 O3 2.89(4) no . 2_646
H23 C11 3.12(3) no . 2_746
H23 C12 3.06(3) no . 2_746
H23 C13 3.54(3) no . 2_746
H23 H22 3.31(5) no . 2_746
H23 H22 3.25(5) no . 2_756
H23 H23 3.29(5) no . 2_746
H23 H23 3.29(5) no . 2_756
H23 H24 3.59(5) no . 2_646
H24 O3 2.52(3) no . 2_646
H24 C15 3.31(4) no . 2_646
H24 H22 3.33(4) no . 2_756
H24 H23 3.59(5) no . 2_656
H24 H24 3.12(5) no . 2_646
H24 H24 3.12(5) no . 2_656
H25 O2 3.06(3) no . 1_455
H25 C8 3.39(3) no . 1_455
H25 C9 3.42(4) no . 1_455
H25 C10 3.15(4) no . 1_455
H25 C10 3.49(4) no . 1_465
H25 C11 3.37(4) no . 1_465
H25 H21 2.76(5) no . 1_455
H25 H21 3.08(5) no . 1_465
H25 H22 2.82(5) no . 1_465
H26 O2 3.06(4) no . 1_455
H26 O5 2.34(3) no . 2_555
H26 C10 3.39(4) no . 1_465
H26 C19 3.48(4) no . 1_565
H26 C20 3.47(3) no . 2_555
H26 H21 2.65(5) no . 1_465
H26 H27 3.36(5) no . 1_565
H26 H28 2.83(5) no . 1_565
H27 O2 2.50(4) no . 1_455
H27 O5 2.97(3) no . 2_545
H27 O5 2.88(3) no . 2_555
H27 N7 3.05(3) no . 2_545
H27 C8 3.40(4) no . 1_455
H27 C10 3.60(3) no . 1_455
H27 C20 3.12(3) no . 2_545
H27 H21 2.82(5) no . 1_455
H27 H26 3.36(5) no . 1_545
H27 H29 2.74(4) no . 2_545
H28 F1 2.49(3) no . 1_545
H28 O4 2.65(4) no . 1_545
H28 O5 3.49(3) no . 2_545
H28 C16 2.88(4) no . 1_545
H28 C17 3.11(4) no . 1_545
H28 C18 3.46(4) no . 1_545
H28 H21 2.85(5) no . 1_455
H28 H26 2.83(5) no . 1_545
H29 O2 2.84(4) no . 2_655
H29 O4 2.48(4) no . 2_645
H29 N7 3.45(4) no . 2_655
H29 C16 3.45(4) no . 2_645
H29 H27 2.74(4) no . 2_555
H29 H29 3.34(5) no . 2_645
H29 H29 3.34(5) no . 2_655

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1009507'
#######################################################################
#
#                 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_20110506

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H9 F N2 O4'
_chemical_formula_moiety         'C13 H9 F N2 O4'
_chemical_formula_weight         276.22
_chemical_melting_point          ?
_chemical_absolute_configuration ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.1322(4)
_cell_length_b                   5.2282(3)
_cell_length_c                   15.7662(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.237(3)
_cell_angle_gamma                90.0000
_cell_volume                     576.63(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6886
_cell_measurement_theta_min      5.72
_cell_measurement_theta_max      68.15
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284.00
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            9552
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_full        68.21
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2059
_reflns_number_gt                1737
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1089
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2059
_refine_ls_number_parameters     218
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0210P)²+0.2075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0045(12)
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  875 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.1(3)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.3525(3) 0.2986(4) 0.25161(10) 0.0316(5) Uani 1.0 2 d . . .
O2 O 0.3346(3) 0.7394(6) 0.36940(12) 0.0366(6) Uani 1.0 2 d . . .
O3 O 0.6958(3) 0.7421(5) 0.15827(12) 0.0332(6) Uani 1.0 2 d . . .
O4 O 0.1409(4) 0.8900(6) -0.02793(14) 0.0438(7) Uani 1.0 2 d . . .
O5 O 0.4915(3) 0.2425(5) 0.11142(12) 0.0315(6) Uani 1.0 2 d . . .
N6 N 0.4777(3) 0.7006(6) 0.24894(14) 0.0255(7) Uani 1.0 2 d . . .
N7 N 0.3278(4) 0.5840(6) 0.04511(16) 0.0297(7) Uani 1.0 2 d . . .
C8 C 0.4606(4) 0.7913(7) 0.33158(17) 0.0280(8) Uani 1.0 2 d . . .
C9 C 0.6279(5) 0.9631(7) 0.35939(18) 0.0293(8) Uani 1.0 2 d . . .
C10 C 0.6735(5) 1.1100(8) 0.4330(2) 0.0348(9) Uani 1.0 2 d . . .
C11 C 0.8336(5) 1.2655(8) 0.4405(2) 0.0392(9) Uani 1.0 2 d . . .
C12 C 0.9411(5) 1.2745(8) 0.3763(2) 0.0384(9) Uani 1.0 2 d . . .
C13 C 0.8934(5) 1.1242(8) 0.3025(2) 0.0342(9) Uani 1.0 2 d . . .
C14 C 0.7350(4) 0.9693(7) 0.29550(19) 0.0289(8) Uani 1.0 2 d . . .
C15 C 0.6461(4) 0.7954(7) 0.22388(17) 0.0257(7) Uani 1.0 2 d . . .
C16 C 0.1920(4) 0.7790(7) 0.03995(18) 0.0302(8) Uani 1.0 2 d . . .
C17 C 0.1209(5) 0.8360(7) 0.12028(19) 0.0279(8) Uani 1.0 2 d . . .
C18 C 0.1394(5) 0.6129(7) 0.1835(2) 0.0254(7) Uani 1.0 2 d . . .
C19 C 0.3429(5) 0.5191(7) 0.20103(19) 0.0274(8) Uani 1.0 2 d . . .
C20 C 0.4000(4) 0.4354(7) 0.11532(19) 0.0261(8) Uani 1.0 2 d . . .
H21 H 0.594(4) 1.115(7) 0.4765(17) 0.018(8) Uiso 1.0 2 d . . .
H22 H 0.856(5) 1.379(9) 0.489(2) 0.047(11) Uiso 1.0 2 d . . .
H23 H 1.046(5) 1.380(9) 0.382(2) 0.049(11) Uiso 1.0 2 d . . .
H24 H 0.963(4) 1.129(7) 0.2579(17) 0.019(8) Uiso 1.0 2 d . . .
H25 H 0.366(4) 0.548(6) -0.0024(17) 0.013(8) Uiso 1.0 2 d . . .
H26 H -0.013(5) 0.893(7) 0.1017(18) 0.029(9) Uiso 1.0 2 d . . .
H27 H 0.200(5) 0.988(8) 0.148(2) 0.041(10) Uiso 1.0 2 d . . .
H28 H 0.106(4) 0.655(7) 0.2371(18) 0.022(8) Uiso 1.0 2 d . . .
H29 H 0.071(5) 0.475(8) 0.156(2) 0.032(10) Uiso 1.0 2 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C19 1.396(4) yes . .
O2 C8 1.203(4) yes . .
O3 C15 1.190(4) yes . .
O4 C16 1.209(4) yes . .
O5 C20 1.209(5) yes . .
N6 C8 1.414(4) yes . .
N6 C15 1.424(4) yes . .
N6 C19 1.453(4) yes . .
N7 C16 1.398(5) yes . .
N7 C20 1.368(4) yes . .
C8 C9 1.490(5) yes . .
C9 C10 1.377(5) yes . .
C9 C14 1.378(5) yes . .
C10 C11 1.388(5) yes . .
C11 C12 1.384(6) yes . .
C12 C13 1.391(5) yes . .
C13 C14 1.377(5) yes . .
C14 C15 1.492(5) yes . .
C16 C17 1.484(5) yes . .
C17 C18 1.523(5) yes . .
C18 C19 1.506(5) yes . .
C19 C20 1.548(5) yes . .
N7 H25 0.87(3) no . .
C10 H21 0.97(3) no . .
C11 H22 0.96(4) no . .
C12 H23 0.92(4) no . .
C13 H24 0.94(3) no . .
C17 H26 0.99(3) no . .
C17 H27 1.02(4) no . .
C18 H28 0.95(3) no . .
C18 H29 0.93(4) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C8 N6 C15 111.6(3) yes . . .
C8 N6 C19 122.1(3) yes . . .
C15 N6 C19 126.2(3) yes . . .
C16 N7 C20 127.5(3) yes . . .
O2 C8 N6 126.0(3) yes . . .
O2 C8 C9 128.6(3) yes . . .
N6 C8 C9 105.4(3) yes . . .
C8 C9 C10 128.9(3) yes . . .
C8 C9 C14 109.0(3) yes . . .
C10 C9 C14 122.0(3) yes . . .
C9 C10 C11 117.0(4) yes . . .
C10 C11 C12 121.4(4) yes . . .
C11 C12 C13 120.9(4) yes . . .
C12 C13 C14 117.5(4) yes . . .
C9 C14 C13 121.2(3) yes . . .
C9 C14 C15 108.9(3) yes . . .
C13 C14 C15 129.8(3) yes . . .
O3 C15 N6 124.7(3) yes . . .
O3 C15 C14 130.2(3) yes . . .
N6 C15 C14 105.0(3) yes . . .
O4 C16 N7 119.2(3) yes . . .
O4 C16 C17 124.4(3) yes . . .
N7 C16 C17 116.4(3) yes . . .
C16 C17 C18 113.8(3) yes . . .
C17 C18 C19 109.1(3) yes . . .
F1 C19 N6 106.8(3) yes . . .
F1 C19 C18 108.2(3) yes . . .
F1 C19 C20 105.9(3) yes . . .
N6 C19 C18 113.5(3) yes . . .
N6 C19 C20 112.2(3) yes . . .
C18 C19 C20 109.8(3) yes . . .
O5 C20 N7 123.7(3) yes . . .
O5 C20 C19 121.1(3) yes . . .
N7 C20 C19 115.1(3) yes . . .
C16 N7 H25 116.1(19) no . . .
C20 N7 H25 116.3(19) no . . .
C9 C10 H21 122.5(17) no . . .
C11 C10 H21 120.4(17) no . . .
C10 C11 H22 116(3) no . . .
C12 C11 H22 122(3) no . . .
C11 C12 H23 120(3) no . . .
C13 C12 H23 119(3) no . . .
C12 C13 H24 122.3(18) no . . .
C14 C13 H24 120.1(18) no . . .
C16 C17 H26 106.2(17) no . . .
C16 C17 H27 106(2) no . . .
C18 C17 H26 112(2) no . . .
C18 C17 H27 110(2) no . . .
H26 C17 H27 108(3) no . . .
C17 C18 H28 114(2) no . . .
C17 C18 H29 109(2) no . . .
C19 C18 H28 108.3(16) no . . .
C19 C18 H29 104(3) no . . .
H28 C18 H29 113(3) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C8 N6 C15 O3 178.0(3) no . . . .
C8 N6 C15 C14 -2.9(4) no . . . .
C15 N6 C8 O2 -178.8(3) no . . . .
C15 N6 C8 C9 1.9(4) no . . . .
C8 N6 C19 F1 -60.5(4) no . . . .
C8 N6 C19 C18 58.6(4) no . . . .
C8 N6 C19 C20 -176.1(3) no . . . .
C19 N6 C8 O2 -2.8(5) no . . . .
C19 N6 C8 C9 177.9(3) no . . . .
C15 N6 C19 F1 114.9(3) no . . . .
C15 N6 C19 C18 -126.0(3) no . . . .
C15 N6 C19 C20 -0.7(4) no . . . .
C19 N6 C15 O3 2.2(5) no . . . .
C19 N6 C15 C14 -178.7(3) no . . . .
C16 N7 C20 O5 166.8(3) no . . . .
C16 N7 C20 C19 -8.6(5) no . . . .
C20 N7 C16 O4 -178.8(3) no . . . .
C20 N7 C16 C17 1.5(5) no . . . .
O2 C8 C9 C10 -2.9(6) no . . . .
O2 C8 C9 C14 -179.3(3) no . . . .
N6 C8 C9 C10 176.4(3) no . . . .
N6 C8 C9 C14 -0.0(4) no . . . .
C8 C9 C10 C11 -176.3(3) no . . . .
C8 C9 C14 C13 176.7(3) no . . . .
C8 C9 C14 C15 -1.7(4) no . . . .
C10 C9 C14 C13 -0.1(5) no . . . .
C10 C9 C14 C15 -178.5(3) no . . . .
C14 C9 C10 C11 -0.2(5) no . . . .
C9 C10 C11 C12 0.8(5) no . . . .
C10 C11 C12 C13 -1.0(6) no . . . .
C11 C12 C13 C14 0.6(5) no . . . .
C12 C13 C14 C9 -0.1(5) no . . . .
C12 C13 C14 C15 177.9(3) no . . . .
C9 C14 C15 O3 -178.1(3) no . . . .
C9 C14 C15 N6 2.8(4) no . . . .
C13 C14 C15 O3 3.6(6) no . . . .
C13 C14 C15 N6 -175.4(4) no . . . .
O4 C16 C17 C18 156.2(3) no . . . .
N7 C16 C17 C18 -24.1(4) no . . . .
C16 C17 C18 C19 53.1(4) no . . . .
C17 C18 C19 F1 -173.8(3) no . . . .
C17 C18 C19 N6 67.9(4) no . . . .
C17 C18 C19 C20 -58.7(4) no . . . .
F1 C19 C20 O5 -21.3(4) no . . . .
F1 C19 C20 N7 154.2(3) no . . . .
N6 C19 C20 O5 94.8(4) no . . . .
N6 C19 C20 N7 -89.7(3) no . . . .
C18 C19 C20 O5 -137.9(3) no . . . .
C18 C19 C20 N7 37.6(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 O2 2.978(3) no . .
F1 O5 2.609(3) no . .
F1 N7 3.554(3) no . .
F1 C8 2.906(4) no . .
F1 C15 3.417(4) no . .
O2 C10 3.108(4) no . .
O2 C14 3.501(4) no . .
O2 C15 3.503(4) no . .
O2 C18 3.062(4) no . .
O2 C19 2.905(4) no . .
O3 O5 3.012(4) no . .
O3 N7 2.989(3) no . .
O3 C8 3.483(4) no . .
O3 C9 3.496(4) no . .
O3 C13 3.146(4) no . .
O3 C19 2.968(4) no . .
O3 C20 2.631(4) no . .
O4 C20 3.540(4) no . .
O5 N6 3.245(4) no . .
O5 C15 3.457(4) no . .
O5 C16 3.572(4) no . .
O5 C18 3.530(4) no . .
N6 N7 3.241(4) no . .
N6 C16 3.544(4) no . .
N6 C17 3.014(4) no . .
N7 C15 3.439(4) no . .
N7 C18 2.780(5) no . .
C8 C18 3.080(4) no . .
C9 C12 2.735(5) no . .
C10 C13 2.821(5) no . .
C11 C14 2.738(5) no . .
C15 C20 2.895(5) no . .
C16 C19 2.897(5) no . .
C17 C20 2.901(5) no . .
F1 O2 3.479(4) no . 1_545
F1 N6 3.254(4) no . 1_545
F1 C8 2.973(4) no . 1_545
F1 C9 2.919(4) no . 1_545
F1 C10 3.441(4) no . 1_545
F1 C14 3.186(4) no . 1_545
F1 C15 3.443(4) no . 1_545
F1 C17 3.396(4) no . 1_545
O2 F1 3.479(4) no . 1_565
O2 C10 3.199(4) no . 2_646
O2 C11 3.441(5) no . 2_646
O3 O4 3.146(4) no . 2_645
O3 O5 3.016(4) no . 1_565
O3 C17 3.240(4) no . 1_655
O3 C18 3.183(4) no . 1_655
O4 O3 3.146(4) no . 2_655
O4 O4 3.513(4) no . 2_545
O4 O4 3.513(4) no . 2_555
O4 O5 3.512(3) no . 1_565
O4 O5 3.247(4) no . 2_655
O4 N7 3.453(4) no . 2_555
O4 C16 3.104(5) no . 2_555
O4 C17 3.596(5) no . 2_545
O4 C17 3.160(5) no . 2_555
O4 C18 3.075(4) no . 2_555
O5 O3 3.016(4) no . 1_545
O5 O4 3.512(3) no . 1_545
O5 O4 3.247(4) no . 2_645
O5 N6 3.581(4) no . 1_545
O5 N7 3.111(4) no . 2_645
O5 C14 3.393(4) no . 1_545
O5 C15 3.011(4) no . 1_545
O5 C16 3.281(4) no . 1_545
O5 C16 3.595(4) no . 2_645
O5 C17 3.416(5) no . 1_545
N6 F1 3.254(4) no . 1_565
N6 O5 3.581(4) no . 1_565
N7 O4 3.453(4) no . 2_545
N7 O5 3.111(4) no . 2_655
C8 F1 2.973(4) no . 1_565
C9 F1 2.919(4) no . 1_565
C10 F1 3.441(4) no . 1_565
C10 O2 3.199(4) no . 2_656
C11 O2 3.441(5) no . 2_656
C14 F1 3.186(4) no . 1_565
C14 O5 3.393(4) no . 1_565
C15 F1 3.443(4) no . 1_565
C15 O5 3.011(4) no . 1_565
C16 O4 3.104(5) no . 2_545
C16 O5 3.281(4) no . 1_565
C16 O5 3.595(4) no . 2_655
C17 F1 3.396(4) no . 1_565
C17 O3 3.240(4) no . 1_455
C17 O4 3.160(5) no . 2_545
C17 O4 3.596(5) no . 2_555
C17 O5 3.416(5) no . 1_565
C18 O3 3.183(4) no . 1_455
C18 O4 3.075(4) no . 2_545
F1 H28 2.54(3) no . .
F1 H29 2.45(3) no . .
O2 H21 2.99(3) no . .
O2 H28 2.43(3) no . .
O3 H24 3.00(3) no . .
O3 H25 3.26(3) no . .
O4 H25 2.39(3) no . .
O4 H26 2.50(3) no . .
O4 H27 2.78(4) no . .
O5 H25 2.44(3) no . .
O5 H29 3.44(4) no . .
N6 H27 2.74(4) no . .
N6 H28 2.63(3) no . .
N6 H29 3.21(4) no . .
N7 H26 3.19(4) no . .
N7 H27 2.92(4) no . .
N7 H29 2.83(4) no . .
C8 H21 2.85(3) no . .
C8 H27 3.28(4) no . .
C8 H28 2.77(3) no . .
C9 H22 3.21(4) no . .
C9 H24 3.24(3) no . .
C10 H23 3.25(4) no . .
C11 H24 3.27(3) no . .
C12 H21 3.29(3) no . .
C13 H22 3.29(4) no . .
C14 H21 3.29(3) no . .
C14 H23 3.20(4) no . .
C15 H24 2.82(3) no . .
C15 H27 3.33(4) no . .
C16 H28 3.35(3) no . .
C16 H29 2.69(4) no . .
C17 H25 3.22(3) no . .
C19 H25 3.25(3) no . .
C19 H26 3.34(3) no . .
C19 H27 2.72(4) no . .
C20 H27 3.31(4) no . .
C20 H28 3.31(3) no . .
C20 H29 2.56(4) no . .
H21 H22 2.30(5) no . .
H22 H23 2.36(6) no . .
H23 H24 2.34(5) no . .
H25 H29 3.59(5) no . .
H26 H28 2.47(4) no . .
H26 H29 2.38(6) no . .
H27 H28 2.41(5) no . .
H27 H29 2.84(6) no . .
F1 H23 3.31(4) no . 1_445
F1 H24 2.94(3) no . 1_445
F1 H27 2.40(4) no . 1_545
O2 H21 2.47(3) no . 2_646
O2 H22 2.92(4) no . 2_646
O2 H23 2.82(4) no . 1_445
O2 H24 3.53(3) no . 1_455
O3 H25 2.89(3) no . 2_655
O3 H26 2.54(4) no . 1_655
O3 H28 2.98(3) no . 1_655
O3 H29 3.02(4) no . 1_655
O4 H25 3.55(3) no . 2_655
O4 H26 2.92(4) no . 2_545
O4 H26 2.95(4) no . 2_555
O4 H27 3.48(4) no . 2_545
O4 H29 2.32(3) no . 2_555
O5 H25 2.39(3) no . 2_645
O5 H27 2.63(4) no . 1_545
N7 H25 3.42(3) no . 2_655
N7 H26 3.06(3) no . 2_545
C8 H21 3.26(3) no . 2_646
C10 H22 3.55(4) no . 2_746
C10 H23 3.41(4) no . 2_746
C11 H22 3.04(4) no . 2_746
C11 H23 3.42(4) no . 2_746
C12 H22 3.11(4) no . 2_746
C12 H28 3.34(4) no . 1_665
C13 H26 3.57(3) no . 1_655
C13 H28 3.16(4) no . 1_655
C13 H28 3.42(4) no . 1_665
C13 H29 3.38(4) no . 1_665
C14 H28 3.39(3) no . 1_655
C15 H26 3.42(4) no . 1_655
C15 H28 3.32(3) no . 1_655
C16 H26 3.09(3) no . 2_545
C16 H29 3.44(3) no . 2_555
C17 H24 3.05(3) no . 1_455
C17 H29 3.42(4) no . 1_565
C18 H23 3.54(4) no . 1_445
C18 H24 3.15(4) no . 1_445
C18 H24 3.29(4) no . 1_455
C18 H27 3.35(5) no . 1_545
C19 H27 3.02(4) no . 1_545
C20 H25 3.35(3) no . 2_645
C20 H27 2.84(4) no . 1_545
H21 O2 2.47(3) no . 2_656
H21 C8 3.26(3) no . 2_656
H21 H21 3.09(5) no . 2_646
H21 H21 3.09(5) no . 2_656
H21 H22 3.58(5) no . 2_646
H21 H23 3.29(4) no . 2_746
H22 O2 2.92(4) no . 2_656
H22 C10 3.55(4) no . 2_756
H22 C11 3.04(4) no . 2_756
H22 C12 3.11(4) no . 2_756
H22 H21 3.58(5) no . 2_656
H22 H22 3.30(6) no . 2_746
H22 H22 3.30(6) no . 2_756
H22 H23 3.29(6) no . 2_746
H22 H23 3.30(6) no . 2_756
H23 F1 3.31(4) no . 1_665
H23 O2 2.82(4) no . 1_665
H23 C10 3.41(4) no . 2_756
H23 C11 3.42(4) no . 2_756
H23 C18 3.54(4) no . 1_665
H23 H21 3.29(4) no . 2_756
H23 H22 3.30(6) no . 2_746
H23 H22 3.29(6) no . 2_756
H23 H28 2.80(5) no . 1_665
H24 F1 2.94(3) no . 1_665
H24 O2 3.53(3) no . 1_655
H24 C17 3.05(3) no . 1_655
H24 C18 3.29(4) no . 1_655
H24 C18 3.15(4) no . 1_665
H24 H26 2.79(5) no . 1_655
H24 H27 2.74(5) no . 1_655
H24 H28 2.72(5) no . 1_655
H24 H28 2.97(5) no . 1_665
H24 H29 2.63(5) no . 1_665
H25 O3 2.89(3) no . 2_645
H25 O4 3.55(3) no . 2_645
H25 O5 2.39(3) no . 2_655
H25 N7 3.42(3) no . 2_645
H25 C20 3.35(3) no . 2_655
H25 H25 3.23(5) no . 2_645
H25 H25 3.23(5) no . 2_655
H25 H26 2.81(4) no . 2_545
H26 O3 2.54(4) no . 1_455
H26 O4 2.95(4) no . 2_545
H26 O4 2.92(4) no . 2_555
H26 N7 3.06(3) no . 2_555
H26 C13 3.57(3) no . 1_455
H26 C15 3.42(4) no . 1_455
H26 C16 3.09(3) no . 2_555
H26 H24 2.79(5) no . 1_455
H26 H25 2.81(4) no . 2_555
H26 H29 3.19(6) no . 1_565
H27 F1 2.40(4) no . 1_565
H27 O4 3.48(4) no . 2_555
H27 O5 2.63(4) no . 1_565
H27 C18 3.35(5) no . 1_565
H27 C19 3.02(4) no . 1_565
H27 C20 2.84(4) no . 1_565
H27 H24 2.74(5) no . 1_455
H27 H29 2.72(6) no . 1_565
H28 O3 2.98(3) no . 1_455
H28 C12 3.34(4) no . 1_445
H28 C13 3.42(4) no . 1_445
H28 C13 3.16(4) no . 1_455
H28 C14 3.39(3) no . 1_455
H28 C15 3.32(3) no . 1_455
H28 H23 2.80(5) no . 1_445
H28 H24 2.97(5) no . 1_445
H28 H24 2.72(5) no . 1_455
H29 O3 3.02(4) no . 1_455
H29 O4 2.32(3) no . 2_545
H29 C13 3.38(4) no . 1_445
H29 C16 3.44(3) no . 2_545
H29 C17 3.42(4) no . 1_545
H29 H24 2.63(5) no . 1_445
H29 H26 3.19(6) no . 1_545
H29 H27 2.72(6) no . 1_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1009504'
#######################################################################
#
#                 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_20110415

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H9 F N2 O4'
_chemical_formula_moiety         'C13 H9 F N2 O4'
_chemical_formula_weight         276.22
_chemical_melting_point          ?
_chemical_absolute_configuration ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   6.56098(12)
_cell_length_b                   13.5445(3)
_cell_length_c                   13.6122(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1209.65(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19794
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      68.28
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568.00
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            19872
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2208
_reflns_number_gt                2192
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0692
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2208
_refine_ls_number_parameters     210
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0384P)²+0.2803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0075(6)
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  908 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.06(15)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F20 F 0.74502(15) 0.37993(6) -0.14342(6) 0.0283(3) Uani 1.0 4 d . . .
O1 O 1.00348(18) 0.52773(8) -0.15132(9) 0.0320(3) Uani 1.0 4 d . . .
O2 O 0.61704(16) 0.72794(7) 0.03581(8) 0.0259(3) Uani 1.0 4 d . . .
O3 O 1.07039(17) 0.47671(8) 0.05856(9) 0.0316(3) Uani 1.0 4 d . . .
O4 O 0.48000(18) 0.29758(8) 0.02814(9) 0.0319(3) Uani 1.0 4 d . . .
N5 N 0.75695(18) 0.40570(8) 0.02284(9) 0.0208(3) Uani 1.0 4 d . . .
N6 N 0.81275(19) 0.62451(9) -0.05104(10) 0.0222(3) Uani 1.0 4 d . . .
C7 C 0.9399(3) 0.41694(10) 0.07634(11) 0.0226(4) Uani 1.0 4 d . . .
C8 C 0.9308(3) 0.34349(11) 0.15690(11) 0.0231(4) Uani 1.0 4 d . . .
C9 C 1.0733(3) 0.32273(12) 0.22920(12) 0.0276(4) Uani 1.0 4 d . . .
C10 C 1.0274(3) 0.24619(13) 0.29339(12) 0.0326(4) Uani 1.0 4 d . . .
C11 C 0.8476(3) 0.19310(13) 0.28516(12) 0.0339(4) Uani 1.0 4 d . . .
C12 C 0.7049(3) 0.21425(12) 0.21260(12) 0.0300(4) Uani 1.0 4 d . . .
C13 C 0.7515(3) 0.29065(11) 0.14887(11) 0.0235(4) Uani 1.0 4 d . . .
C14 C 0.6380(3) 0.32681(10) 0.06171(11) 0.0230(4) Uani 1.0 4 d . . .
C15 C 0.8633(3) 0.53582(11) -0.09507(11) 0.0222(4) Uani 1.0 4 d . . .
C16 C 0.6340(3) 0.64784(10) -0.00388(10) 0.0205(3) Uani 1.0 4 d . . .
C17 C 0.4663(3) 0.57203(11) -0.00507(13) 0.0251(4) Uani 1.0 4 d . . .
C18 C 0.4978(3) 0.49009(11) -0.07981(12) 0.0241(4) Uani 1.0 4 d . . .
C19 C 0.7143(3) 0.45048(10) -0.07158(11) 0.0217(3) Uani 1.0 4 d . . .
H21 H 1.195(3) 0.3561(13) 0.2294(13) 0.0215 Uiso 1.0 4 d . . .
H22 H 1.116(3) 0.2302(12) 0.3426(14) 0.0215 Uiso 1.0 4 d . . .
H23 H 0.824(3) 0.1431(13) 0.3282(13) 0.0215 Uiso 1.0 4 d . . .
H24 H 0.580(3) 0.1773(13) 0.2051(12) 0.0215 Uiso 1.0 4 d . . .
H25 H 0.895(3) 0.6714(14) -0.0574(13) 0.0215 Uiso 1.0 4 d . . .
H26 H 0.408(3) 0.4399(13) -0.0716(13) 0.0215 Uiso 1.0 4 d . . .
H27 H 0.483(3) 0.5135(13) -0.1436(14) 0.0215 Uiso 1.0 4 d . . .
H28 H 0.466(3) 0.5470(13) 0.0625(14) 0.0215 Uiso 1.0 4 d . . .
H29 H 0.341(3) 0.6045(12) -0.0202(13) 0.0215 Uiso 1.0 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F20 C19 1.3821(17) yes . .
O1 C15 1.202(2) yes . .
O2 C16 1.2171(17) yes . .
O3 C7 1.2027(19) yes . .
O4 C14 1.200(2) yes . .
N5 C7 1.412(2) yes . .
N5 C14 1.4250(19) yes . .
N5 C19 1.4485(19) yes . .
N6 C15 1.383(2) yes . .
N6 C16 1.3741(19) yes . .
C7 C8 1.482(2) yes . .
C8 C9 1.386(3) yes . .
C8 C13 1.381(3) yes . .
C9 C10 1.389(3) yes . .
C10 C11 1.386(3) yes . .
C11 C12 1.391(3) yes . .
C12 C13 1.385(3) yes . .
C13 C14 1.484(3) yes . .
C15 C19 1.548(2) yes . .
C16 C17 1.505(2) yes . .
C17 C18 1.520(3) yes . .
C18 C19 1.522(3) yes . .
N6 H25 0.838(19) no . .
C9 H21 0.918(19) no . .
C10 H22 0.912(19) no . .
C11 H23 0.908(18) no . .
C12 H24 0.965(19) no . .
C17 H28 0.980(18) no . .
C17 H29 0.953(19) no . .
C18 H26 0.907(19) no . .
C18 H27 0.930(18) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C7 N5 C14 110.79(12) yes . . .
C7 N5 C19 125.22(12) yes . . .
C14 N5 C19 122.51(12) yes . . .
C15 N6 C16 127.38(13) yes . . .
O3 C7 N5 125.01(14) yes . . .
O3 C7 C8 129.02(15) yes . . .
N5 C7 C8 105.96(12) yes . . .
C7 C8 C9 129.37(15) yes . . .
C7 C8 C13 108.88(14) yes . . .
C9 C8 C13 121.70(15) yes . . .
C8 C9 C10 116.86(16) yes . . .
C9 C10 C11 121.39(17) yes . . .
C10 C11 C12 121.56(16) yes . . .
C11 C12 C13 116.76(17) yes . . .
C8 C13 C12 121.72(15) yes . . .
C8 C13 C14 108.65(13) yes . . .
C12 C13 C14 129.54(15) yes . . .
O4 C14 N5 125.38(14) yes . . .
O4 C14 C13 128.99(14) yes . . .
N5 C14 C13 105.63(13) yes . . .
O1 C15 N6 122.62(14) yes . . .
O1 C15 C19 123.18(14) yes . . .
N6 C15 C19 114.05(13) yes . . .
O2 C16 N6 119.35(13) yes . . .
O2 C16 C17 123.11(14) yes . . .
N6 C16 C17 117.53(13) yes . . .
C16 C17 C18 113.94(13) yes . . .
C17 C18 C19 109.58(13) yes . . .
F20 C19 N5 108.06(11) yes . . .
F20 C19 C15 106.13(12) yes . . .
F20 C19 C18 109.14(13) yes . . .
N5 C19 C15 111.95(12) yes . . .
N5 C19 C18 113.16(13) yes . . .
C15 C19 C18 108.13(12) yes . . .
C15 N6 H25 117.4(13) no . . .
C16 N6 H25 115.1(13) no . . .
C8 C9 H21 119.3(11) no . . .
C10 C9 H21 123.7(11) no . . .
C9 C10 H22 120.0(11) no . . .
C11 C10 H22 118.6(11) no . . .
C10 C11 H23 118.5(12) no . . .
C12 C11 H23 120.0(12) no . . .
C11 C12 H24 122.6(11) no . . .
C13 C12 H24 120.6(11) no . . .
C16 C17 H28 103.1(11) no . . .
C16 C17 H29 108.5(11) no . . .
C18 C17 H28 112.0(10) no . . .
C18 C17 H29 108.0(11) no . . .
H28 C17 H29 111.2(15) no . . .
C17 C18 H26 112.1(11) no . . .
C17 C18 H27 111.2(11) no . . .
C19 C18 H26 109.5(12) no . . .
C19 C18 H27 106.8(11) no . . .
H26 C18 H27 107.5(16) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C7 N5 C14 O4 -176.32(13) no . . . .
C7 N5 C14 C13 3.24(15) no . . . .
C14 N5 C7 O3 178.69(13) no . . . .
C14 N5 C7 C8 -2.79(14) no . . . .
C7 N5 C19 F20 100.11(14) no . . . .
C7 N5 C19 C15 -16.41(18) no . . . .
C7 N5 C19 C18 -138.92(12) no . . . .
C19 N5 C7 O3 12.3(3) no . . . .
C19 N5 C7 C8 -169.14(11) no . . . .
C14 N5 C19 F20 -64.72(16) no . . . .
C14 N5 C19 C15 178.76(11) no . . . .
C14 N5 C19 C18 56.25(16) no . . . .
C19 N5 C14 O4 -9.5(3) no . . . .
C19 N5 C14 C13 170.02(11) no . . . .
C15 N6 C16 O2 176.12(13) no . . . .
C15 N6 C16 C17 -4.5(2) no . . . .
C16 N6 C15 O1 164.43(14) no . . . .
C16 N6 C15 C19 -11.2(2) no . . . .
O3 C7 C8 C9 -2.9(3) no . . . .
O3 C7 C8 C13 179.62(14) no . . . .
N5 C7 C8 C9 178.69(13) no . . . .
N5 C7 C8 C13 1.18(15) no . . . .
C7 C8 C9 C10 -177.25(14) no . . . .
C7 C8 C13 C12 177.73(12) no . . . .
C7 C8 C13 C14 0.78(16) no . . . .
C9 C8 C13 C12 -0.0(3) no . . . .
C9 C8 C13 C14 -176.95(13) no . . . .
C13 C8 C9 C10 -0.0(3) no . . . .
C8 C9 C10 C11 0.1(3) no . . . .
C9 C10 C11 C12 -0.2(3) no . . . .
C10 C11 C12 C13 0.2(3) no . . . .
C11 C12 C13 C8 -0.1(3) no . . . .
C11 C12 C13 C14 176.18(14) no . . . .
C8 C13 C14 O4 177.10(14) no . . . .
C8 C13 C14 N5 -2.43(16) no . . . .
C12 C13 C14 O4 0.5(3) no . . . .
C12 C13 C14 N5 -179.07(15) no . . . .
O1 C15 C19 F20 -14.7(2) no . . . .
O1 C15 C19 N5 103.00(17) no . . . .
O1 C15 C19 C18 -131.67(15) no . . . .
N6 C15 C19 F20 160.92(12) no . . . .
N6 C15 C19 N5 -81.39(15) no . . . .
N6 C15 C19 C18 43.93(16) no . . . .
O2 C16 C17 C18 164.84(12) no . . . .
N6 C16 C17 C18 -14.52(19) no . . . .
C16 C17 C18 C19 47.80(17) no . . . .
C17 C18 C19 F20 -176.67(11) no . . . .
C17 C18 C19 N5 62.97(15) no . . . .
C17 C18 C19 C15 -61.64(15) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F20 O1 2.6258(15) no . .
F20 O4 3.1179(15) no . .
F20 N6 3.5711(15) no . .
F20 C7 3.2917(18) no . .
F20 C14 2.9677(17) no . .
O1 O3 2.9719(18) no . .
O1 N5 3.3118(17) no . .
O1 C7 3.4683(19) no . .
O1 C16 3.5430(19) no . .
O1 C18 3.495(2) no . .
O2 C15 3.5435(19) no . .
O3 N6 3.0151(17) no . .
O3 C9 3.122(2) no . .
O3 C13 3.4983(19) no . .
O3 C14 3.4888(19) no . .
O3 C15 2.619(2) no . .
O3 C19 2.954(2) no . .
O4 C7 3.4858(19) no . .
O4 C8 3.494(2) no . .
O4 C12 3.123(2) no . .
O4 C18 2.9953(19) no . .
O4 C19 2.9144(19) no . .
N5 N6 3.1510(17) no . .
N5 C16 3.3970(18) no . .
N5 C17 2.9761(19) no . .
N6 C7 3.4069(19) no . .
N6 C18 2.782(2) no . .
C7 C15 2.879(2) no . .
C8 C11 2.738(3) no . .
C9 C12 2.838(3) no . .
C10 C13 2.740(3) no . .
C14 C18 3.074(3) no . .
C15 C17 2.920(3) no . .
C16 C19 2.876(2) no . .
F20 O4 3.2588(15) no . 2_555
F20 C9 3.1886(19) no . 2_455
F20 C10 3.021(2) no . 2_455
F20 C11 3.391(2) no . 2_455
F20 C12 3.409(2) no . 2_555
O1 C18 3.424(2) no . 1_655
O2 O2 3.4741(15) no . 2_465
O2 O2 3.4741(15) no . 2_565
O2 N6 2.8324(16) no . 2_465
O2 C10 3.303(2) no . 3_755
O2 C10 3.451(2) no . 4_664
O2 C11 3.583(2) no . 4_664
O2 C17 3.5728(18) no . 2_565
O3 C17 3.0270(19) no . 1_655
O3 C18 3.383(2) no . 1_655
O4 F20 3.2588(15) no . 2_455
O4 N5 3.1944(16) no . 2_455
O4 C7 3.2456(18) no . 2_455
O4 C8 3.1779(19) no . 2_455
O4 C13 3.079(2) no . 2_455
O4 C14 3.0609(19) no . 2_455
N5 O4 3.1944(16) no . 2_555
N6 O2 2.8324(16) no . 2_565
N6 C10 3.540(3) no . 4_664
N6 C11 3.490(3) no . 4_664
C7 O4 3.2456(18) no . 2_555
C8 O4 3.1779(19) no . 2_555
C9 F20 3.1886(19) no . 2_555
C10 F20 3.021(2) no . 2_555
C10 O2 3.303(2) no . 3_745
C10 O2 3.451(2) no . 4_665
C10 N6 3.540(3) no . 4_665
C10 C16 3.286(3) no . 4_665
C11 F20 3.391(2) no . 2_555
C11 O2 3.583(2) no . 4_665
C11 N6 3.490(3) no . 4_665
C11 C16 3.592(3) no . 4_665
C12 F20 3.409(2) no . 2_455
C13 O4 3.079(2) no . 2_555
C14 O4 3.0609(19) no . 2_555
C16 C10 3.286(3) no . 4_664
C16 C11 3.592(3) no . 4_664
C17 O2 3.5728(18) no . 2_465
C17 O3 3.0270(19) no . 1_455
C18 O1 3.424(2) no . 1_455
C18 O3 3.383(2) no . 1_455
F20 H26 2.551(19) no . .
F20 H27 2.497(18) no . .
O1 H25 2.435(18) no . .
O1 H27 3.424(18) no . .
O2 H25 2.350(19) no . .
O2 H28 2.668(17) no . .
O2 H29 2.579(18) no . .
O3 H21 2.957(18) no . .
O3 H25 3.281(18) no . .
O4 H24 2.981(17) no . .
O4 H26 2.405(18) no . .
O4 H28 3.411(17) no . .
N5 H26 2.667(19) no . .
N5 H27 3.241(18) no . .
N5 H28 2.756(18) no . .
N6 H27 2.923(18) no . .
N6 H28 2.943(18) no . .
N6 H29 3.134(19) no . .
C7 H21 2.797(18) no . .
C7 H28 3.578(18) no . .
C8 H22 3.196(18) no . .
C8 H24 3.285(19) no . .
C9 H23 3.225(18) no . .
C10 H24 3.306(19) no . .
C11 H21 3.264(19) no . .
C12 H22 3.232(19) no . .
C13 H21 3.234(19) no . .
C13 H23 3.191(18) no . .
C14 H24 2.838(17) no . .
C14 H26 2.814(18) no . .
C14 H28 3.188(17) no . .
C15 H26 3.274(19) no . .
C15 H27 2.602(18) no . .
C15 H28 3.378(18) no . .
C16 H26 3.314(18) no . .
C16 H27 2.814(18) no . .
C17 H25 3.199(19) no . .
C18 H25 3.594(19) no . .
C19 H25 3.224(18) no . .
C19 H28 2.773(18) no . .
C19 H29 3.291(18) no . .
H21 H22 2.36(3) no . .
H22 H23 2.26(3) no . .
H23 H24 2.36(3) no . .
H26 H28 2.36(3) no . .
H26 H29 2.38(3) no . .
H27 H28 2.84(3) no . .
H27 H29 2.28(3) no . .
F20 H21 3.420(18) no . 2_455
F20 H22 3.208(18) no . 2_455
F20 H24 2.478(19) no . 2_555
O1 H21 3.004(18) no . 4_764
O1 H24 2.915(18) no . 2_555
O1 H26 3.103(19) no . 1_655
O1 H27 3.151(18) no . 1_655
O1 H29 3.029(18) no . 1_655
O2 H22 2.411(19) no . 3_755
O2 H22 3.095(19) no . 4_664
O2 H23 3.344(18) no . 4_664
O2 H25 2.017(19) no . 2_465
O2 H29 2.713(18) no . 2_565
O3 H23 2.817(18) no . 3_755
O3 H26 2.880(19) no . 1_655
O3 H28 2.766(18) no . 1_655
O3 H29 2.702(18) no . 1_655
O4 H21 3.409(18) no . 1_455
N6 H22 3.213(18) no . 3_755
N6 H29 3.503(19) no . 1_655
C8 H27 3.384(18) no . 4_665
C9 H27 2.838(18) no . 4_665
C9 H29 3.595(17) no . 4_665
C10 H27 3.367(17) no . 4_665
C10 H29 3.358(17) no . 4_665
C11 H25 3.240(18) no . 4_665
C11 H26 3.442(17) no . 2_555
C11 H27 3.511(18) no . 2_555
C11 H28 3.529(18) no . 3_645
C12 H25 3.554(18) no . 4_665
C12 H26 3.133(18) no . 2_555
C13 H26 3.450(18) no . 2_555
C15 H24 3.549(18) no . 2_555
C15 H29 3.426(19) no . 1_655
C16 H22 2.960(18) no . 3_755
C16 H22 3.128(18) no . 4_664
C16 H25 3.024(18) no . 2_465
C17 H22 3.431(18) no . 4_664
C17 H23 3.219(18) no . 3_655
C18 H21 3.562(18) no . 4_664
C19 H24 3.473(18) no . 2_555
H21 F20 3.420(18) no . 2_555
H21 O1 3.004(18) no . 4_765
H21 O4 3.409(18) no . 1_655
H21 C18 3.562(18) no . 4_665
H21 H24 3.51(3) no . 1_655
H21 H27 2.73(3) no . 4_665
H21 H29 3.46(3) no . 4_665
H22 F20 3.208(18) no . 2_555
H22 O2 2.411(19) no . 3_745
H22 O2 3.095(19) no . 4_665
H22 N6 3.213(18) no . 3_745
H22 C16 2.960(18) no . 3_745
H22 C16 3.128(18) no . 4_665
H22 C17 3.431(18) no . 4_665
H22 H25 3.03(3) no . 3_745
H22 H27 3.54(3) no . 4_665
H22 H29 2.93(3) no . 4_665
H23 O2 3.344(18) no . 4_665
H23 O3 2.817(18) no . 3_745
H23 C17 3.219(18) no . 3_645
H23 H25 3.29(3) no . 4_665
H23 H27 3.45(3) no . 2_555
H23 H28 2.75(3) no . 3_645
H23 H29 2.88(3) no . 3_645
H24 F20 2.478(19) no . 2_455
H24 O1 2.915(18) no . 2_455
H24 C15 3.549(18) no . 2_455
H24 C19 3.473(18) no . 2_455
H24 H21 3.51(3) no . 1_455
H24 H26 3.23(3) no . 2_555
H25 O2 2.017(19) no . 2_565
H25 C11 3.240(18) no . 4_664
H25 C12 3.554(18) no . 4_664
H25 C16 3.024(18) no . 2_565
H25 H22 3.03(3) no . 3_755
H25 H23 3.29(3) no . 4_664
H25 H29 3.11(3) no . 1_655
H25 H29 3.23(3) no . 2_565
H26 O1 3.103(19) no . 1_455
H26 O3 2.880(19) no . 1_455
H26 C11 3.442(17) no . 2_455
H26 C12 3.133(18) no . 2_455
H26 C13 3.450(18) no . 2_455
H26 H24 3.23(3) no . 2_455
H27 O1 3.151(18) no . 1_455
H27 C8 3.384(18) no . 4_664
H27 C9 2.838(18) no . 4_664
H27 C10 3.367(17) no . 4_664
H27 C11 3.511(18) no . 2_455
H27 H21 2.73(3) no . 4_664
H27 H22 3.54(3) no . 4_664
H27 H23 3.45(3) no . 2_455
H28 O3 2.766(18) no . 1_455
H28 C11 3.529(18) no . 3_655
H28 H23 2.75(3) no . 3_655
H29 O1 3.029(18) no . 1_455
H29 O2 2.713(18) no . 2_465
H29 O3 2.702(18) no . 1_455
H29 N6 3.503(19) no . 1_455
H29 C9 3.595(17) no . 4_664
H29 C10 3.358(17) no . 4_664
H29 C15 3.426(19) no . 1_455
H29 H21 3.46(3) no . 4_664
H29 H22 2.93(3) no . 4_664
H29 H23 2.88(3) no . 3_655
H29 H25 3.11(3) no . 1_455
H29 H25 3.23(3) no . 2_465

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N6 H25 O2 . . 2_565 2.8324(16) 0.838 2.017(19) 164.3(17) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1009505'
