# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_thp-BA
_database_code_depnum_ccdc_archive 'CCDC 1451259'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2011-08-17T12:27:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
theophylline benzoic acid cocrystal 
;
_chemical_formula_sum            'C14 H14 N4 O4'
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H6 O2'
_chemical_formula_weight         302.29

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

_cell_length_a                   6.9150(2)
_cell_length_b                   25.1050(6)
_cell_length_c                   8.6000(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.190(1)
_cell_angle_gamma                90
_cell_volume                     1410.01(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35
_cell_measurement_reflns_used    6728

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.995

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_number            7041
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       'omega and phi scans'
_reflns_number_total             2452
_reflns_number_gt                2093
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0366P)²+0.5091P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2452
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
H1N H 0.243(3) 0.0749(8) -0.069(2) 0.050(5) Uiso 1 1 d . . .
O2 O 0.28895(17) 0.03066(4) 0.27015(13) 0.0347(3) Uani 1 1 d . . .
O1 O 0.32760(17) 0.18076(4) 0.58127(12) 0.0349(3) Uani 1 1 d . . .
N3 N 0.31553(18) 0.10645(5) 0.42432(14) 0.0258(3) Uani 1 1 d . . .
N2 N 0.27736(18) 0.19315(5) 0.30943(14) 0.0254(3) Uani 1 1 d . . .
C2 C 0.2627(2) 0.16986(6) 0.16135(17) 0.0239(3) Uani 1 1 d . . .
N1 N 0.24309(19) 0.19581(5) 0.01874(15) 0.0303(3) Uani 1 1 d . . .
N4 N 0.24696(19) 0.10749(5) -0.01845(15) 0.0285(3) Uani 1 1 d . . .
C5 C 0.2666(2) 0.11584(6) 0.14429(17) 0.0239(3) Uani 1 1 d . . .
C3 C 0.3078(2) 0.16162(6) 0.44582(17) 0.0257(3) Uani 1 1 d . . .
C4 C 0.2889(2) 0.07979(6) 0.27576(17) 0.0255(3) Uani 1 1 d . . .
C1 C 0.2354(2) 0.15608(6) -0.08642(19) 0.0315(4) Uani 1 1 d . . .
H1 H 0.2231 0.1615 -0.1962 0.038 Uiso 1 1 calc R . .
C7 C 0.3549(3) 0.07369(6) 0.57341(19) 0.0371(4) Uani 1 1 d . . .
H7A H 0.2279 0.0665 0.592 0.056 Uiso 1 1 calc R . .
H7B H 0.4449 0.0925 0.6663 0.056 Uiso 1 1 calc R . .
H7C H 0.4175 0.0407 0.5593 0.056 Uiso 1 1 calc R . .
C6 C 0.2576(3) 0.25075(6) 0.3242(2) 0.0371(4) Uani 1 1 d . . .
H6A H 0.2371 0.2672 0.2193 0.056 Uiso 0.5 1 calc PR . .
H6B H 0.38 0.2646 0.4033 0.056 Uiso 0.5 1 calc PR . .
H6C H 0.1426 0.2583 0.3598 0.056 Uiso 0.5 1 calc PR . .
H6D H 0.2694 0.2595 0.4357 0.056 Uiso 0.5 1 calc PR . .
H6E H 0.1264 0.2621 0.2516 0.056 Uiso 0.5 1 calc PR . .
H6F H 0.3639 0.2684 0.2951 0.056 Uiso 0.5 1 calc PR . .
O3 O 0.76127(19) 0.04786(5) -0.05466(14) 0.0415(3) Uani 1 1 d . . .
O4 O 0.7547(2) -0.00705(4) 0.14780(15) 0.0475(3) Uani 1 1 d . . .
C9 C 0.7770(2) 0.08591(6) 0.20007(19) 0.0294(3) Uani 1 1 d . . .
C13 C 0.8092(2) 0.12309(7) 0.4649(2) 0.0384(4) Uani 1 1 d . . .
H13 H 0.8241 0.1185 0.5756 0.046 Uiso 1 1 calc R . .
C10 C 0.7659(2) 0.13706(6) 0.1353(2) 0.0333(4) Uani 1 1 d . . .
H10 H 0.7524 0.1418 0.025 0.04 Uiso 1 1 calc R . .
C8 C 0.7635(2) 0.03767(6) 0.09636(19) 0.0310(4) Uani 1 1 d . . .
C12 C 0.7971(2) 0.17395(7) 0.3997(2) 0.0393(4) Uani 1 1 d . . .
H12 H 0.8038 0.2035 0.4667 0.047 Uiso 1 1 calc R . .
C14 C 0.7990(2) 0.07897(6) 0.3655(2) 0.0341(4) Uani 1 1 d . . .
H14 H 0.8069 0.0449 0.4093 0.041 Uiso 1 1 calc R . .
C11 C 0.7751(2) 0.18083(6) 0.2354(2) 0.0388(4) Uani 1 1 d . . .
H11 H 0.7664 0.215 0.1919 0.047 Uiso 1 1 calc R . .
H3O H 0.741(3) 0.0165(10) -0.121(3) 0.073(7) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C4 1.2344(17) . ?
O1 C3 1.2255(17) . ?
N3 C4 1.3998(18) . ?
N3 C3 1.4007(19) . ?
N3 C7 1.4714(18) . ?
N2 C3 1.3726(18) . ?
N2 C2 1.3743(18) . ?
N2 C6 1.4621(19) . ?
C2 N1 1.3556(18) . ?
C2 C5 1.365(2) . ?
N1 C1 1.335(2) . ?
N4 C1 1.3437(19) . ?
N4 C5 1.3770(18) . ?
N4 H1N 0.92(2) . ?
C5 C4 1.417(2) . ?
C1 H1 0.93 . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C6 H6D 0.96 . ?
C6 H6E 0.96 . ?
C6 H6F 0.96 . ?
O3 C8 1.3189(19) . ?
O3 H3O 0.95(2) . ?
O4 C8 1.2155(19) . ?
C9 C14 1.391(2) . ?
C9 C10 1.392(2) . ?
C9 C8 1.489(2) . ?
C13 C12 1.386(2) . ?
C13 C14 1.387(2) . ?
C13 H13 0.93 . ?
C10 C11 1.385(2) . ?
C10 H10 0.93 . ?
C12 C11 1.381(2) . ?
C12 H12 0.93 . ?
C14 H14 0.93 . ?
C11 H11 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N3 C3 126.44(12) . . ?
C4 N3 C7 117.34(12) . . ?
C3 N3 C7 116.22(12) . . ?
C3 N2 C2 119.36(13) . . ?
C3 N2 C6 119.23(12) . . ?
C2 N2 C6 121.39(12) . . ?
N1 C2 C5 112.31(13) . . ?
N1 C2 N2 126.08(13) . . ?
C5 C2 N2 121.61(13) . . ?
C1 N1 C2 102.92(12) . . ?
C1 N4 C5 106.01(12) . . ?
C1 N4 H1N 127.7(12) . . ?
C5 N4 H1N 126.3(12) . . ?
C2 C5 N4 105.17(12) . . ?
C2 C5 C4 123.34(13) . . ?
N4 C5 C4 131.48(13) . . ?
O1 C3 N2 121.61(14) . . ?
O1 C3 N3 121.06(13) . . ?
N2 C3 N3 117.33(12) . . ?
O2 C4 N3 120.78(13) . . ?
O2 C4 C5 127.49(13) . . ?
N3 C4 C5 111.73(13) . . ?
N1 C1 N4 113.58(13) . . ?
N1 C1 H1 123.2 . . ?
N4 C1 H1 123.2 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C6 H6D 109.5 . . ?
H6A C6 H6D 141.1 . . ?
H6B C6 H6D 56.3 . . ?
H6C C6 H6D 56.3 . . ?
N2 C6 H6E 109.5 . . ?
H6A C6 H6E 56.3 . . ?
H6B C6 H6E 141.1 . . ?
H6C C6 H6E 56.3 . . ?
H6D C6 H6E 109.5 . . ?
N2 C6 H6F 109.5 . . ?
H6A C6 H6F 56.3 . . ?
H6B C6 H6F 56.3 . . ?
H6C C6 H6F 141.1 . . ?
H6D C6 H6F 109.5 . . ?
H6E C6 H6F 109.5 . . ?
C8 O3 H3O 112.4(13) . . ?
C14 C9 C10 119.86(14) . . ?
C14 C9 C8 118.37(14) . . ?
C10 C9 C8 121.77(14) . . ?
C12 C13 C14 120.13(16) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C11 C10 C9 119.89(15) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
O4 C8 O3 123.48(14) . . ?
O4 C8 C9 122.29(14) . . ?
O3 C8 C9 114.23(13) . . ?
C11 C12 C13 120.06(15) . . ?
C11 C12 H12 120 . . ?
C13 C12 H12 120 . . ?
C13 C14 C9 119.80(15) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C12 C11 C10 120.26(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?






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

data_thp-2FBA
_database_code_depnum_ccdc_archive 'CCDC 1451260'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_systematic        
; ?
;
_chemical_name_common            'theophylline:2-fluorobenzoic acid'
_chemical_formula_moiety         '(C7 H8 N4 O2), (C7 H5 F1 O2)'
_chemical_formula_structural     '(C7 H8 N4 O2), (C7 H5 F1 O2)'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C14 H13 F1 N4 O4'
_chemical_formula_weight         320.28
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and 
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_length_neutron # include if applicable
? ? ? ? ? ?

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-p 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'-x, -y, -z'
'-x+1/2, y+1/2, -z+1/2'
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a                   6.99605(15)
_cell_length_b                   25.41715(87)
_cell_length_c                   8.60318(40)
_cell_angle_alpha                90
_cell_angle_beta                 109.6613(22)
_cell_angle_gamma                90
_cell_volume                     1440.62(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_theta_min      2
_cell_measurement_theta_max      60
_cell_measurement_reflns_used    20
_exptl_crystal_density_diffrn    1.4782(5)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_cell_special_details            
; ?
;



# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 'borosilicate capillary'
;
_pd_spec_mount_mode              transmission

_pd_spec_shape                   cylinder

_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions



_pd_prep_temperature             293


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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_source_voltage           40
_diffrn_source_current           30
_diffrn_measurement_device_type  'Stoe StadiP'
_diffrn_detector                 'Single photon counting'
_diffrn_detector_type            'DECTRIS MYTHEN 1K'
_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)

_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  none

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        3861
_pd_meas_2theta_range_min        2.000
_pd_meas_2theta_range_max        59.900
_pd_meas_2theta_range_inc        0.015




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

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'


_pd_proc_ls_prof_R_factor        0.046
_pd_proc_ls_prof_wR_factor       0.062
_pd_proc_ls_prof_wR_expected     0.034
_refine_ls_R_I_factor            0.028


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     41
_refine_ls_number_restraints     0
_refine_ls_number_constraints    96

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   3.903


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        60
_pd_proc_2theta_range_inc        0.008
_pd_proc_wavelength              1.5418

# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting 
# of one data block containing a single powder profile. The value of 
# _pd_block_diffractogram_id is used to associate each refinement with 
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template 
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given 
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?




# The following items are used to identify the programs used.

_computing_data_collection       "X'Pert Data Collector (Panalytical )"
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'DASH 3.2 (David et al 2008) '
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C9 C 0.71012(43) 0.41747(13) 0.78771(38) 1 3.98(11)
C8 C 0.73003(59) 0.46467(14) 0.89611(54) 1 3.98(11)
O3 O 0.73805(63) 0.45428(21) 1.04863(51) 1 3.98(11)
H9 H 0.76082(76) 0.48222(25) 1.11105(64) 1 3.98(11)
O4 O 0.73850(94) 0.50948(13) 0.84271(77) 1 3.98(11)
C14 C 0.72353(48) 0.36617(13) 0.84946(45) 1 3.98(11)
F1 F 0.75233(72) 0.35747(19) 1.01031(49) 1 3.98(11)
C13 C 0.70837(64) 0.32292(14) 0.73501(67) 1 3.98(11)
H13 H 0.71793(88) 0.28846(13) 0.77722(86) 1 3.98(11)
C12 C 0.67983(66) 0.33218(21) 0.57055(63) 1 3.98(11)
H12 H 0.67124(82) 0.30302(26) 0.50074(80) 1 3.98(11)
C11 C 0.66639(73) 0.38398(25) 0.51077(43) 1 3.98(11)
H11 H 0.64779(95) 0.39072(32) 0.39896(43) 1 3.98(11)
C10 C 0.68218(67) 0.42589(18) 0.61926(40) 1 3.98(11)
H10 H 0.67540(91) 0.46095(20) 0.58258(52) 1 3.98(11)
N3 N 0.17753(45) 0.39408(13) 0.58068(44) 1 3.98(11)
C5 C 0.18259(37) 0.33937(14) 0.55593(45) 1 3.98(11)
N4 N 0.21246(42) 0.307086(97) 0.69176(56) 1 3.98(11)
C6 C 0.22911(37) 0.32866(12) 0.84144(48) 1 3.98(11)
C2 C 0.22958(39) 0.38301(13) 0.86330(42) 1 3.98(11)
C3 C 0.20822(52) 0.419269(95) 0.73281(52) 1 3.98(11)
N2 N 0.25007(51) 0.38998(22) 1.02674(44) 1 3.98(11)
C1 C 0.25991(54) 0.34137(26) 1.09313(45) 1 3.98(11)
N1 N 0.24850(55) 0.30272(20) 0.98393(58) 1 3.98(11)
C4 C 0.13909(68) 0.42700(21) 0.43324(56) 1 3.98(11)
O2 O 0.16126(51) 0.32083(22) 0.41853(50) 1 3.98(11)
C7 C 0.22783(72) 0.25035(10) 0.67059(84) 1 3.98(11)
O1 O 0.21204(80) 0.468397(96) 0.74225(76) 1 3.98(11)
H2 H 0.25443(66) 0.42114(25) 1.07578(54) 1 3.98(11)
H1 H 0.26845(66) 0.33572(33) 1.20324(47) 1 3.98(11)
H5 H 0.04204(65) 0.41021(26) 0.34258(49) 1 3.98(11)
H3 H 0.08916(83) 0.45998(19) 0.45286(71) 1 3.98(11)
H4 H 0.26071(74) 0.43222(23) 0.40946(60) 1 3.98(11)
H7 H 0.31053(77) 0.24416(14) 0.60520(88) 1 3.98(11)
H8 H 0.28903(81) 0.23514(11) 0.77593(93) 1 3.98(11)
H6 H 0.09730(81) 0.23566(12) 0.61774(93) 1 3.98(11)
#==============================================================================


# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 C8 1.497(5)
C9 C14 1.399(5)
C9 C10 1.412(5)
C8 O3 1.321(7)
C8 O4 1.237(6)
O3 H9 0.872(8)
C14 F1 1.348(6)
C14 C13 1.456(6)
C13 H13 0.942(6)
C13 C12 1.381(8)
C12 H12 0.943(9)
C12 C11 1.405(8)
C11 H11 0.942(6)
C11 C10 1.396(7)
C10 H10 0.941(7)
N3 C5 1.409(5)
N3 C3 1.407(6)
N3 C4 1.467(6)
C5 N4 1.385(6)
C5 O2 1.234(6)
N4 C6 1.368(6)
N4 C7 1.462(4)
C6 C2 1.394(5)
C6 N1 1.358(6)
C2 C3 1.421(5)
C2 N2 1.376(5)
C3 O1 1.251(3)
N2 C1 1.353(8)
N2 H2 0.893(8)
C1 N1 1.343(8)
C1 H1 0.940(6)
C4 H5 0.946(6)
C4 H3 0.945(8)
C4 H4 0.949(8)
C7 H7 0.95(1)
C7 H8 0.945(9)
C7 H6 0.949(6)




loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 C9 C14 122.0(3)
C8 C9 C10 118.0(3)
C14 C9 C10 120.0(3)
C9 C8 O3 115.0(4)
C9 C8 O4 120.8(4)
O3 C8 O4 124.2(5)
C8 O3 H9 112.8(6)
C9 C14 F1 120.7(3)
C9 C14 C13 117.8(3)
F1 C14 C13 121.5(4)
C14 C13 H13 117.5(5)
C14 C13 C12 121.1(4)
H13 C13 C12 121.4(6)
C13 C12 H12 118.3(6)
C13 C12 C11 120.2(5)
H12 C12 C11 121.4(6)
C12 C11 H11 120.9(6)
C12 C11 C10 119.3(4)
H11 C11 C10 119.8(6)
C9 C10 C11 121.5(4)
C9 C10 H10 117.5(5)
C11 C10 H10 121.0(5)
C5 N3 C3 125.9(3)
C5 N3 C4 116.0(3)
C3 N3 C4 118.1(3)
N3 C5 N4 117.5(3)
N3 C5 O2 121.4(4)
N4 C5 O2 121.1(4)
C5 N4 C6 119.8(3)
C5 N4 C7 118.4(3)
C6 N4 C7 121.7(3)
N4 C6 C2 121.3(3)
N4 C6 N1 127.3(3)
C2 C6 N1 111.4(3)
C6 C2 C3 122.8(3)
C6 C2 N2 105.1(3)
C3 C2 N2 132.1(3)
N3 C3 C2 112.5(3)
N3 C3 O1 120.5(4)
C2 C3 O1 127.0(4)
C2 N2 C1 106.7(4)
C2 N2 H2 124.9(5)
C1 N2 H2 128.4(6)
N2 C1 N1 113.0(4)
N2 C1 H1 122.8(6)
N1 C1 H1 124.2(6)
C6 N1 C1 103.9(4)
N3 C4 H5 109.1(5)
N3 C4 H3 108.8(5)
N3 C4 H4 110.4(5)
H5 C4 H3 110.0(7)
H5 C4 H4 109.4(7)
H3 C4 H4 109.1(7)
N4 C7 H7 108.9(5)
N4 C7 H8 108.2(5)
N4 C7 H6 110.4(5)
H7 C7 H8 109.4(7)
H7 C7 H6 109.4(7)
H8 C7 H6 110.5(7)

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

data_thp-3FBA
_database_code_depnum_ccdc_archive 'CCDC 1451261'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_systematic        
; ?
;
_chemical_name_common            'theophylline:3-fluorobenzoic acid'
_chemical_formula_moiety         '(C7 H8 N4 O2), (C7 H5 F1 O2)'
_chemical_formula_structural     '(C7 H8 N4 O2), (C7 H5 F1 O2)'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C14 H13 F1 N4 O4'
_chemical_formula_weight         320.28
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and 
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_length_neutron # include if applicable
? ? ? ? ? ?

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-p 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'-x, -y, -z'
'-x+1/2, y+1/2, -z+1/2'
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a                   6.95661(26)
_cell_length_b                   25.0530(13)
_cell_length_c                   8.67305(65)
_cell_angle_alpha                90
_cell_angle_beta                 107.5894(35)
_cell_angle_gamma                90
_cell_volume                     1440.90(20)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_theta_min      2
_cell_measurement_theta_max      60
_cell_measurement_reflns_used    20
_exptl_crystal_density_diffrn    1.4764(2)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_cell_special_details            
; ?
;

# The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              14 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              10 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              0.5 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 'packed powder pellet'
;
_pd_spec_mount_mode              reflection

_pd_spec_shape                   flat_sheet

_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions



_pd_prep_temperature             293


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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_measurement_device_type  "Panalytical X'pert Powder"
_diffrn_detector                 ?
_diffrn_detector_type            X'Celerator

_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  none

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        5875
_pd_meas_2theta_range_min        3.00
_pd_meas_2theta_range_max        50.00
_pd_meas_2theta_range_inc        0.008



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

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'


_pd_proc_ls_prof_R_factor        0.044
_pd_proc_ls_prof_wR_factor       0.055
_pd_proc_ls_prof_wR_expected     0.021
_refine_ls_R_I_factor            0.012


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     35
_refine_ls_number_restraints     0
_refine_ls_number_constraints    96

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   2.698


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        50
_pd_proc_2theta_range_inc        0.008
_pd_proc_wavelength              1.5418

# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting 
# of one data block containing a single powder profile. The value of 
# _pd_block_diffractogram_id is used to associate each refinement with 
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template 
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given 
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?




# The following items are used to identify the programs used.

_computing_data_collection       "X'Pert Data Collector (Panalytical )"
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'DASH 3.2 (David et al 2008) '
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
F1 F 0.16991(80) 0.37997(20) -0.11256(38) 1 3.26(12)
C9 C 0.22338(28) 0.41277(12) 0.30701(39) 1 3.26(12)
C10 C 0.23908(66) 0.36129(14) 0.37456(46) 1 3.26(12)
C11 C 0.23443(81) 0.31648(11) 0.27726(59) 1 3.26(12)
C12 C 0.21132(62) 0.32238(12) 0.11176(56) 1 3.26(12)
C13 C 0.19328(45) 0.37392(13) 0.04779(40) 1 3.26(12)
C14 C 0.19981(36) 0.41938(11) 0.14121(37) 1 3.26(12)
C8 C 0.23671(50) 0.46172(15) 0.40832(49) 1 3.26(12)
O4 O 0.22288(73) 0.50694(13) 0.34870(64) 1 3.26(12)
O3 O 0.26586(74) 0.45175(22) 0.56352(49) 1 3.26(12)
H10 H 0.25433(92) 0.35754(18) 0.48534(48) 1 3.26(12)
H11 H 0.2466(11) 0.28196(12) 0.32227(73) 1 3.26(12)
H12 H 0.20937(81) 0.29230(14) 0.04591(68) 1 3.26(12)
H13 H 0.19043(65) 0.45368(12) 0.09561(43) 1 3.26(12)
H9 H 0.28102(86) 0.48056(25) 0.62197(57) 1 3.26(12)
N3 N 0.68455(34) 0.39263(12) 0.08245(42) 1 3.26(12)
C5 C 0.69764(46) 0.33710(13) 0.06266(42) 1 3.26(12)
N4 N 0.72443(49) 0.305180(89) 0.19791(48) 1 3.26(12)
C6 C 0.73339(37) 0.32805(10) 0.34327(41) 1 3.26(12)
C2 C 0.72480(30) 0.38327(11) 0.35987(39) 1 3.26(12)
C3 C 0.70359(34) 0.419261(81) 0.22914(48) 1 3.26(12)
N2 N 0.74224(53) 0.39164(18) 0.52021(41) 1 3.26(12)
C1 C 0.75852(59) 0.34300(21) 0.59026(38) 1 3.26(12)
N1 N 0.75453(56) 0.30295(16) 0.48608(47) 1 3.26(12)
C4 C 0.65070(56) 0.42470(19) -0.06490(50) 1 3.26(12)
O2 O 0.68594(70) 0.31759(19) -0.07051(47) 1 3.26(12)
C7 C 0.74881(83) 0.247673(98) 0.18117(71) 1 3.26(12)
O1 O 0.69967(60) 0.469097(81) 0.23446(66) 1 3.26(12)
H2 H 0.74257(68) 0.42362(20) 0.56602(50) 1 3.26(12)
H1 H 0.76874(75) 0.33814(27) 0.69992(39) 1 3.26(12)
H5 H 0.77146(64) 0.42761(22) -0.09374(55) 1 3.26(12)
H3 H 0.60798(63) 0.45908(17) -0.04498(62) 1 3.26(12)
H4 H 0.54966(62) 0.40831(22) -0.15013(44) 1 3.26(12)
H7 H 0.62388(93) 0.232235(98) 0.12115(74) 1 3.26(12)
H8 H 0.84638(91) 0.24180(14) 0.12676(78) 1 3.26(12)
H6 H 0.79422(87) 0.23267(10) 0.28578(77) 1 3.26(12)
#==============================================================================


# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance

F1 C13 1.359(5)
C9 C10 1.407(5)
C9 C14 1.407(5)
C9 C8 1.495(5)
C10 C11 1.399(5)
C10 H10 0.939(6)
C11 C12 1.403(7)
C11 H11 0.942(5)
C12 C13 1.396(5)
C12 H12 0.943(6)
C13 C14 1.390(4)
C14 H13 0.940(4)
C8 O4 1.237(5)
C8 O3 1.323(6)
O3 H9 0.870(8)
N3 C5 1.408(4)
N3 C3 1.407(5)
N3 C4 1.467(6)
C5 N4 1.385(5)
C5 O2 1.234(6)
N4 C6 1.369(5)
N4 C7 1.463(4)
C6 C2 1.394(4)
C6 N1 1.357(5)
C2 C3 1.421(5)
C2 N2 1.375(5)
C3 O1 1.250(3)
N2 C1 1.351(7)
N2 H2 0.894(7)
C1 N1 1.345(6)
C1 H1 0.940(5)
C4 H5 0.949(7)
C4 H3 0.944(7)
C4 H4 0.946(5)
C7 H7 0.950(7)
C7 H8 0.95(1)
C7 H6 0.944(8)


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle

C10 C9 C14 120.3(3)
C10 C9 C8 121.6(3)
C14 C9 C8 118.1(3)
C9 C10 C11 120.0(4)
C9 C10 H10 119.2(5)
C11 C10 H10 120.8(5)
C10 C11 C12 120.5(4)
C10 C11 H11 120.3(6)
C12 C11 H11 119.3(6)
C11 C12 C13 118.2(4)
C11 C12 H12 120.8(5)
C13 C12 H12 121.0(5)
F1 C13 C12 118.6(3)
F1 C13 C14 118.5(3)
C12 C13 C14 122.9(3)
C9 C14 C13 118.2(3)
C9 C14 H13 120.6(4)
C13 C14 H13 121.2(4)
C9 C8 O4 121.5(4)
C9 C8 O3 114.0(4)
O4 C8 O3 124.5(4)
C8 O3 H9 113.0(6)
C5 N3 C3 125.9(3)
C5 N3 C4 115.7(3)
C3 N3 C4 118.3(3)
N3 C5 N4 117.7(3)
N3 C5 O2 121.1(4)
N4 C5 O2 121.2(4)
C5 N4 C6 119.7(3)
C5 N4 C7 118.3(3)
C6 N4 C7 121.9(3)
N4 C6 C2 121.3(3)
N4 C6 N1 127.5(3)
C2 C6 N1 111.2(3)
C6 C2 C3 123.0(3)
C6 C2 N2 105.2(3)
C3 C2 N2 131.8(3)
N3 C3 C2 112.3(3)
N3 C3 O1 120.7(3)
C2 C3 O1 127.0(3)
C2 N2 C1 106.7(3)
C2 N2 H2 125.0(5)
C1 N2 H2 128.3(5)
N2 C1 N1 112.9(4)
N2 C1 H1 122.8(5)
N1 C1 H1 124.3(5)
C6 N1 C1 104.0(3)
N3 C4 H5 110.5(5)
N3 C4 H3 108.5(5)
N3 C4 H4 109.2(5)
H5 C4 H3 109.3(6)
H5 C4 H4 109.6(6)
H3 C4 H4 109.8(6)
N4 C7 H7 109.9(5)
N4 C7 H8 108.9(5)
N4 C7 H6 108.2(5)
H7 C7 H8 109.8(7)
H7 C7 H6 110.5(6)
H8 C7 H6 109.6(7)


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

data_thp-25diFBA
_database_code_depnum_ccdc_archive 'CCDC 1451262'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2016-01-21T13:24:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         'C7 H8 N4 O2, 2(C7 H4 F2 O2)'
_chemical_formula_sum            'C21 H16 F4 N4 O6'
_chemical_formula_weight         496.38

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8052(5)
_cell_length_b                   7.4527(3)
_cell_length_c                   20.4399(17)
_cell_angle_alpha                93.757(5)
_cell_angle_beta                 99.392(7)
_cell_angle_gamma                90.405(4)
_cell_volume                     1020.39(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    5278
_cell_measurement_theta_min      5.9310
_cell_measurement_theta_max      73.4920

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.047
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             508

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.71535
_exptl_absorpt_correction_T_max  1.00000

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_number            6589
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.395
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_full        66.601
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3576
_reflns_number_gt                3218
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+0.2815P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3576
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -14.9734 3.7046 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0032(2) 0.7496(2) 0.25280(8) 0.0200(3) Uani 1 1 d . . . . .
H1 H -0.1018 0.7666 0.2186 0.024 Uiso 1 1 calc R U . . .
C2 C 0.2887(2) 0.6655(2) 0.30526(8) 0.0170(3) Uani 1 1 d . . . . .
C3 C 0.4781(2) 0.5928(2) 0.32636(8) 0.0174(3) Uani 1 1 d . . . . .
C4 C 0.4394(2) 0.7162(2) 0.44009(8) 0.0196(4) Uani 1 1 d . . . . .
C5 C 0.1817(2) 0.7537(2) 0.34838(8) 0.0173(3) Uani 1 1 d . . . . .
C6 C 0.7314(3) 0.5417(2) 0.42153(9) 0.0241(4) Uani 1 1 d . . . . .
H6A H 0.7588 0.567 0.4688 0.036 Uiso 1 1 calc R U . . .
H6B H 0.7264 0.4139 0.4116 0.036 Uiso 1 1 calc R U . . .
H6C H 0.8348 0.594 0.4017 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1507(3) 0.8893(2) 0.46036(8) 0.0245(4) Uani 1 1 d . . . . .
H7A H 0.226 0.893 0.5044 0.037 Uiso 0.5 1 calc R U P . .
H7B H 0.1354 1.0094 0.4461 0.037 Uiso 0.5 1 calc R U P . .
H7C H 0.0218 0.8361 0.4603 0.037 Uiso 0.5 1 calc R U P . .
H7D H 0.0294 0.9327 0.4361 0.037 Uiso 0.5 1 calc R U P . .
H7E H 0.1201 0.8163 0.4945 0.037 Uiso 0.5 1 calc R U P . .
H7F H 0.2337 0.9895 0.4803 0.037 Uiso 0.5 1 calc R U P . .
C8 C 0.5617(2) 0.0090(2) 0.27952(8) 0.0208(4) Uani 1 1 d . . . . .
C9 C 0.3709(2) 0.1044(2) 0.28314(8) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.3281(2) 0.1761(2) 0.34391(8) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.4187 0.1671 0.3828 0.023 Uiso 1 1 calc R U . . .
C11 C 0.1492(3) 0.2607(2) 0.34524(9) 0.0219(4) Uani 1 1 d . . . . .
C12 C 0.0088(3) 0.2777(2) 0.28929(9) 0.0235(4) Uani 1 1 d . . . . .
H12 H -0.1106 0.3352 0.2922 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0497(3) 0.2073(2) 0.22871(9) 0.0236(4) Uani 1 1 d . . . . .
H13 H -0.0419 0.217 0.1901 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2289(3) 0.1224(2) 0.22643(8) 0.0206(4) Uani 1 1 d . . . . .
F1 F 0.26219(16) 0.05552(16) 0.16646(5) 0.0302(3) Uani 1 1 d . . . . .
F2 F 0.10947(17) 0.33057(16) 0.40459(5) 0.0335(3) Uani 1 1 d . . . . .
N1 N 0.0033(2) 0.80731(19) 0.31623(7) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.1706(2) 0.66498(19) 0.24385(7) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.5397(2) 0.61814(19) 0.39487(7) 0.0188(3) Uani 1 1 d . . . . .
N4 N 0.2556(2) 0.78187(19) 0.41491(7) 0.0194(3) Uani 1 1 d . . . . .
O1 O 0.58581(17) 0.51268(16) 0.29135(6) 0.0215(3) Uani 1 1 d . . . . .
O2 O 0.51037(19) 0.74136(18) 0.49839(6) 0.0280(3) Uani 1 1 d . . . . .
O3 O 0.6092(2) -0.0532(2) 0.22884(7) 0.0392(4) Uani 1 1 d . . . . .
O4 O 0.67454(18) -0.00202(18) 0.33861(6) 0.0250(3) Uani 1 1 d . . . . .
H4O H 0.7763 -0.0564 0.3341 0.037 Uiso 1 1 calc R U . . .
H1N H 0.199(4) 0.621(3) 0.2083(14) 0.034(6) Uiso 1 1 d . . . . .
C15 C 0.4353(3) 0.4135(2) 0.12303(8) 0.0226(4) Uani 1 1 d . . . . .
C16 C 0.4490(3) 0.3272(2) 0.05611(8) 0.0218(4) Uani 1 1 d . . . . .
C17 C 0.2704(3) 0.2966(3) 0.01211(9) 0.0271(4) Uani 1 1 d . . . . .
H17 H 0.15 0.329 0.025 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2742(3) 0.2182(3) -0.05035(9) 0.0314(4) Uani 1 1 d . . . . .
C19 C 0.4479(3) 0.1675(3) -0.07242(9) 0.0294(4) Uani 1 1 d . . . . .
H19 H 0.4456 0.1139 -0.1149 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6252(3) 0.1986(3) -0.02944(9) 0.0287(4) Uani 1 1 d . . . . .
H20 H 0.7451 0.1672 -0.043 0.034 Uiso 1 1 calc R U . . .
C21 C 0.6241(3) 0.2765(2) 0.03366(9) 0.0255(4) Uani 1 1 d . . . . .
F3 F 0.09894(19) 0.1886(2) -0.09227(6) 0.0529(4) Uani 1 1 d . . . . .
F4 F 0.80155(16) 0.30535(19) 0.07316(6) 0.0410(3) Uani 1 1 d . . . . .
O5 O 0.28001(19) 0.47779(18) 0.13480(6) 0.0288(3) Uani 1 1 d . . . . .
O6 O 0.5992(2) 0.4115(2) 0.16680(6) 0.0340(3) Uani 1 1 d . . . . .
H1O H 0.58 0.4612 0.2021 0.051 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.338(2) . ?
C1 N1 1.339(2) . ?
C1 H1 0.93 . ?
C2 C5 1.371(2) . ?
C2 N2 1.375(2) . ?
C2 C3 1.414(2) . ?
C3 O1 1.236(2) . ?
C3 N3 1.395(2) . ?
C4 O2 1.212(2) . ?
C4 N4 1.378(2) . ?
C4 N3 1.407(2) . ?
C5 N1 1.359(2) . ?
C5 N4 1.372(2) . ?
C6 N3 1.464(2) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C7 N4 1.463(2) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C7 H7D 0.96 . ?
C7 H7E 0.96 . ?
C7 H7F 0.96 . ?
C8 O3 1.201(2) . ?
C8 O4 1.329(2) . ?
C8 C9 1.495(2) . ?
C9 C10 1.395(2) . ?
C9 C14 1.397(2) . ?
C10 C11 1.378(3) . ?
C10 H10 0.93 . ?
C11 F2 1.357(2) . ?
C11 C12 1.379(2) . ?
C12 C13 1.384(3) . ?
C12 H12 0.93 . ?
C13 C14 1.384(3) . ?
C13 H13 0.93 . ?
C14 F1 1.347(2) . ?
N2 H1N 0.83(3) . ?
O4 H4O 0.82 . ?
C15 O5 1.216(2) . ?
C15 O6 1.312(2) . ?
C15 C16 1.490(2) . ?
C16 C21 1.391(3) . ?
C16 C17 1.397(2) . ?
C17 C18 1.373(3) . ?
C17 H17 0.93 . ?
C18 F3 1.358(2) . ?
C18 C19 1.379(3) . ?
C19 C20 1.380(3) . ?
C19 H19 0.93 . ?
C20 C21 1.381(3) . ?
C20 H20 0.93 . ?
C21 F4 1.346(2) . ?
O6 H1O 0.82 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 112.76(14) . . ?
N2 C1 H1 123.6 . . ?
N1 C1 H1 123.6 . . ?
C5 C2 N2 105.36(14) . . ?
C5 C2 C3 122.60(15) . . ?
N2 C2 C3 132.02(16) . . ?
O1 C3 N3 120.01(15) . . ?
O1 C3 C2 127.27(15) . . ?
N3 C3 C2 112.72(15) . . ?
O2 C4 N4 121.53(17) . . ?
O2 C4 N3 121.80(16) . . ?
N4 C4 N3 116.67(14) . . ?
N1 C5 C2 111.29(15) . . ?
N1 C5 N4 127.03(16) . . ?
C2 C5 N4 121.67(16) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N4 C7 H7D 109.5 . . ?
H7A C7 H7D 141.1 . . ?
H7B C7 H7D 56.3 . . ?
H7C C7 H7D 56.3 . . ?
N4 C7 H7E 109.5 . . ?
H7A C7 H7E 56.3 . . ?
H7B C7 H7E 141.1 . . ?
H7C C7 H7E 56.3 . . ?
H7D C7 H7E 109.5 . . ?
N4 C7 H7F 109.5 . . ?
H7A C7 H7F 56.3 . . ?
H7B C7 H7F 56.3 . . ?
H7C C7 H7F 141.1 . . ?
H7D C7 H7F 109.5 . . ?
H7E C7 H7F 109.5 . . ?
O3 C8 O4 122.82(16) . . ?
O3 C8 C9 124.06(15) . . ?
O4 C8 C9 113.12(15) . . ?
C10 C9 C14 117.89(16) . . ?
C10 C9 C8 120.64(14) . . ?
C14 C9 C8 121.46(16) . . ?
C11 C10 C9 118.82(15) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
F2 C11 C10 118.31(15) . . ?
F2 C11 C12 118.44(16) . . ?
C10 C11 C12 123.25(17) . . ?
C11 C12 C13 118.46(16) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C12 C13 C14 119.07(16) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
F1 C14 C13 117.05(15) . . ?
F1 C14 C9 120.45(16) . . ?
C13 C14 C9 122.51(17) . . ?
C1 N1 C5 103.87(14) . . ?
C1 N2 C2 106.72(14) . . ?
C1 N2 H1N 127.1(17) . . ?
C2 N2 H1N 126.2(18) . . ?
C3 N3 C4 126.24(14) . . ?
C3 N3 C6 116.53(14) . . ?
C4 N3 C6 117.18(14) . . ?
C5 N4 C4 119.89(15) . . ?
C5 N4 C7 122.14(14) . . ?
C4 N4 C7 117.87(14) . . ?
C8 O4 H4O 109.5 . . ?
O5 C15 O6 124.00(16) . . ?
O5 C15 C16 120.79(16) . . ?
O6 C15 C16 115.21(16) . . ?
C21 C16 C17 117.45(16) . . ?
C21 C16 C15 125.64(16) . . ?
C17 C16 C15 116.90(16) . . ?
C18 C17 C16 119.44(18) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
F3 C18 C17 118.56(18) . . ?
F3 C18 C19 118.44(17) . . ?
C17 C18 C19 123.00(18) . . ?
C18 C19 C20 117.94(17) . . ?
C18 C19 H19 121 . . ?
C20 C19 H19 121 . . ?
C19 C20 C21 119.83(18) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
F4 C21 C20 117.23(17) . . ?
F4 C21 C16 120.43(16) . . ?
C20 C21 C16 122.34(17) . . ?
C15 O6 H1O 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

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

data_thp-35diFBA
_database_code_depnum_ccdc_archive 'CCDC 1451263'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_systematic        
; ?
;
_chemical_name_common            'theophylline:3,5-difluorobenzoic acid'
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H4 F2 O2'
_chemical_formula_structural     'C7 H8 N4 O2, C7 H4 F2 O2'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C14 H12 F2 N4 O4'
_chemical_formula_weight         338.28
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and 
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_length_neutron # include if applicable
? ? ? ? ? ?

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-p 2ybc'

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


_cell_length_a                   3.86433(17)
_cell_length_b                   13.61115(66)
_cell_length_c                   27.6863(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.8744(58)
_cell_angle_gamma                90
_cell_volume                     1450.98(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_theta_min      2
_cell_measurement_theta_max      60
_cell_measurement_reflns_used    20
_exptl_crystal_density_diffrn    1.5485(2)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

_cell_special_details            
; ?
;

# The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              14 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              10 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              0.5 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 'packed powder pellet'
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet

_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions



_pd_prep_temperature             293


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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_measurement_device_type  "Panalytical X'pert Powder"
_diffrn_detector                 ?
_diffrn_detector_type            X'Celerator # make or model of detector

_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  none

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        5875
_pd_meas_2theta_range_min        3.00
_pd_meas_2theta_range_max        50.00
_pd_meas_2theta_range_inc        0.008



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

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_pref_orient_corr     
; 'Spherical harmonics'
;

_pd_proc_ls_prof_R_factor        0.056
_pd_proc_ls_prof_wR_factor       0.071
_pd_proc_ls_prof_wR_expected     0.021
_refine_ls_R_I_factor            0.018


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     46
_refine_ls_number_restraints     0
_refine_ls_number_constraints    96

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   3.290


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        50
_pd_proc_2theta_range_inc        0.008
_pd_proc_wavelength              1.5418

# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting 
# of one data block containing a single powder profile. The value of 
# _pd_block_diffractogram_id is used to associate each refinement with 
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template 
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given 
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?




# The following items are used to identify the programs used.

_computing_data_collection       "X'Pert Data Collector (Panalytical )"
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'TOPAS Academic (Coelho 2007)'
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N3 N -0.54598(90) -0.21279(31) -0.04573(26) 1 6.29(14)
C5 C -0.65941(85) -0.29838(26) -0.02404(30) 1 6.29(14)
N4 N -0.57195(92) -0.31186(18) 0.02491(30) 1 6.29(14)
C6 C -0.38888(91) -0.24006(21) 0.05070(26) 1 6.29(14)
C2 C -0.27935(87) -0.15488(16) 0.02856(25) 1 6.29(14)
C3 C -0.35057(96) -0.13621(21) -0.02195(25) 1 6.29(14)
N2 N -0.1078(12) -0.10153(29) 0.06552(26) 1 6.29(14)
C1 C -0.1213(14) -0.15535(43) 0.10636(24) 1 6.29(14)
N1 N -0.2913(13) -0.24062(39) 0.09890(25) 1 6.29(14)
C4 C -0.6379(14) -0.20436(52) -0.09814(26) 1 6.29(14)
O2 O -0.8376(11) -0.36031(38) -0.04794(36) 1 6.29(14)
C7 C -0.6822(14) -0.40065(26) 0.04928(37) 1 6.29(14)
O1 O -0.2607(14) -0.06338(30) -0.04491(28) 1 6.29(14)
H2 H 0.0001(14) -0.04428(30) 0.06308(29) 1 6.29(14)
H1 H -0.0195(17) -0.13435(56) 0.13652(25) 1 6.29(14)
H5 H -0.5134(15) -0.25193(57) -0.11478(26) 1 6.29(14)
H3 H -0.8783(14) -0.21535(58) -0.10518(29) 1 6.29(14)
H4 H -0.5774(16) -0.14056(55) -0.10784(26) 1 6.29(14)
H7 H -0.7195(15) -0.45146(23) 0.02622(41) 1 6.29(14)
H8 H -0.5068(16) -0.41842(30) 0.07364(36) 1 6.29(14)
H6 H -0.8894(15) -0.38825(36) 0.06420(39) 1 6.29(14)
F1 F -0.6707(13) 0.03931(41) -0.82386(16) 1 6.29(14)
F2 F -0.1330(18) 0.27661(33) -0.71828(19) 1 6.29(14)
C9 C -0.2000(11) 0.01171(35) -0.70512(11) 1 6.29(14)
C10 C -0.3900(10) -0.01306(31) -0.74904(13) 1 6.29(14)
C11 C -0.48685(97) 0.06223(32) -0.78138(13) 1 6.29(14)
C12 C -0.4066(11) 0.16091(31) -0.77219(13) 1 6.29(14)
C13 C -0.2160(13) 0.18148(31) -0.72829(13) 1 6.29(14)
C14 C -0.1087(12) 0.10984(37) -0.69434(10) 1 6.29(14)
C8 C -0.0999(15) -0.06652(43) -0.66924(14) 1 6.29(14)
O4 O -0.1861(18) -0.15269(41) -0.67467(20) 1 6.29(14)
O3 O 0.0895(18) -0.03306(54) -0.62987(12) 1 6.29(14)
H10 H -0.4511(13) -0.07863(31) -0.75598(18) 1 6.29(14)
H11 H -0.4797(14) 0.21135(33) -0.79391(16) 1 6.29(14)
H12 H 0.0196(15) 0.12821(45) -0.66538(11) 1 6.29(14)
H9 H 0.1232(20) -0.07835(60) -0.60875(14) 1 6.29(14)

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


# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C5 1.398(7)
N3 C3 1.416(6)
N3 C4 1.47(1)
C5 N4 1.38(1)
C5 O2 1.243(8)
N4 C6 1.371(6)
N4 C7 1.465(8)
C6 C2 1.394(6)
C6 N1 1.36(1)
C2 C3 1.425(9)
C2 N2 1.378(8)
C3 O1 1.243(7)
N2 C1 1.352(9)
N2 H2 0.889(6)
C1 N1 1.341(8)
C1 H1 0.937(9)
C4 H5 0.95(1)
C4 H3 0.945(8)
C4 H4 0.94(1)
C7 H7 0.94(1)
C7 H8 0.95(1)
C7 H6 0.95(1)
F1 C11 1.358(6)
F2 C13 1.357(6)
C9 C10 1.407(5)
C9 C14 1.407(7)
C9 C8 1.485(6)
C10 C11 1.391(6)
C10 H10 0.939(6)
C11 C12 1.397(6)
C12 C13 1.395(5)
C12 H11 0.940(6)
C13 C14 1.393(6)
C14 H12 0.940(5)
C8 O4 1.225(8)
C8 O3 1.340(7)
O3 H9 0.852(9)


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N3 C3 126.0(5)
C5 N3 C4 115.5(5)
C3 N3 C4 118.5(5)
N3 C5 N4 118.2(5)
N3 C5 O2 121.1(5)
N4 C5 O2 120.7(5)
C5 N4 C6 119.3(4)
C5 N4 C7 120.3(5)
C6 N4 C7 120.4(5)
N4 C6 C2 121.8(4)
N4 C6 N1 126.6(5)
C2 C6 N1 111.6(4)
C6 C2 C3 122.6(4)
C6 C2 N2 104.9(4)
C3 C2 N2 132.5(4)
N3 C3 C2 112.1(4)
N3 C3 O1 120.7(5)
C2 C3 O1 127.2(5)
C2 N2 C1 106.6(5)
C2 N2 H2 127.2(7)
C1 N2 H2 126.2(7)
N2 C1 N1 113.2(5)
N2 C1 H1 122.5(7)
N1 C1 H1 124.4(7)
C6 N1 C1 103.8(5)
N3 C4 H5 109.7(7)
N3 C4 H3 110.0(7)
N3 C4 H4 107.9(7)
H5 C4 H3 108.8(9)
H5 C4 H4 110.0(9)
H3 C4 H4 110.5(9)
N4 C7 H7 109.1(7)
N4 C7 H8 108.7(7)
N4 C7 H6 110.1(7)
H7 C7 H8 110.7(9)
H7 C7 H6 109.8(9)
H8 C7 H6 108.4(9)
C10 C9 C14 120.9(4)
C10 C9 C8 119.6(4)
C14 C9 C8 119.5(4)
C9 C10 C11 118.2(4)
C9 C10 H10 120.6(5)
C11 C10 H10 121.3(5)
F1 C11 C10 118.7(4)
F1 C11 C12 118.1(4)
C10 C11 C12 123.2(4)
C11 C12 C13 116.4(4)
C11 C12 H11 122.4(5)
C13 C12 H11 121.2(5)
F2 C13 C12 117.9(4)
F2 C13 C14 118.6(4)
C12 C13 C14 123.5(4)
C9 C14 C13 117.8(4)
C9 C14 H12 122.5(5)
C13 C14 H12 119.6(5)
C9 C8 O4 123.5(5)
C9 C8 O3 113.2(5)
O4 C8 O3 123.3(6)
C8 O3 H9 110.7(7)


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

data_thp-234triFBA
_database_code_depnum_ccdc_archive 'CCDC 1451264'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_thp-234triFBA       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.892 Note
RESPONSE: Numerous attempts to obtain a single crystal suitable for the collection of a full set of data were unsuccessful. The validity of the structural model was confirmed by additional PXRD studies and Rietveld refinements. 
;
# Added during the CSD deposition process: Monday 25 April 2016 10:41 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H3 F3 O2'
_chemical_formula_sum            'C14 H11 F3 N4 O4'
_chemical_formula_weight         356.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   3.8518(1)
_cell_length_b                   12.4949(4)
_cell_length_c                   30.534(2)
_cell_angle_alpha                91.623(2)
_cell_angle_beta                 93.593(1)
_cell_angle_gamma                97.772(1)
_cell_volume                     1452.17(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    16025
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.271
_exptl_absorpt_correction_T_max  1.127
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            8542
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_av_sigmaI/netI    0.0980
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4582
_reflns_number_gt                2937
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0929P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4582
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1675
_refine_ls_wR_factor_gt          0.1589
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.1574(6) 0.37148(18) 0.47385(8) 0.0504(6) Uani 1 1 d . . .
N1 N 0.5653(6) 0.3296(2) 0.61707(9) 0.0415(7) Uani 1 1 d . . .
C1 C 0.6887(8) 0.4275(3) 0.60304(11) 0.0422(8) Uani 1 1 d . . .
H1 H 0.8421 0.4803 0.6205 0.051 Uiso 1 1 calc R . .
O2 O -0.2047(5) 0.05454(18) 0.53969(8) 0.0506(6) Uani 1 1 d . . .
N2 N 0.5720(6) 0.4422(2) 0.56201(9) 0.0391(6) Uani 1 1 d . . .
H2N H 0.6217 0.5006 0.5469 0.059 Uiso 1 1 calc R . .
C2 C 0.3581(7) 0.3483(2) 0.54761(11) 0.0377(8) Uani 1 1 d . . .
C3 C 0.1705(8) 0.3161(3) 0.50685(11) 0.0388(8) Uani 1 1 d . . .
N3 N -0.0111(6) 0.2122(2) 0.50686(9) 0.0387(6) Uani 1 1 d . . .
N4 N 0.1772(6) 0.1796(2) 0.58045(9) 0.0398(7) Uani 1 1 d . . .
C4 C -0.0224(7) 0.1427(3) 0.54224(11) 0.0393(8) Uani 1 1 d . . .
C5 C 0.3645(7) 0.2813(2) 0.58220(11) 0.0371(8) Uani 1 1 d . . .
C6 C -0.2090(8) 0.1699(3) 0.46542(11) 0.0464(9) Uani 1 1 d . . .
H6A H -0.3152 0.2282 0.4513 0.070 Uiso 1 1 calc R . .
H6B H -0.3940 0.1116 0.4718 0.070 Uiso 1 1 calc R . .
H6C H -0.0488 0.1417 0.4457 0.070 Uiso 1 1 calc R . .
C7 C 0.1900(8) 0.1079(3) 0.61737(12) 0.0497(9) Uani 1 1 d . . .
H7A H 0.1410 0.1462 0.6443 0.074 Uiso 1 1 calc R . .
H7B H 0.4240 0.0855 0.6210 0.074 Uiso 1 1 calc R . .
H7C H 0.0137 0.0440 0.6116 0.074 Uiso 1 1 calc R . .
F1 F 1.3063(6) 0.44143(16) 0.79677(7) 0.0754(7) Uani 1 1 d . . .
F2 F 1.4460(7) 0.34998(17) 0.87223(7) 0.0839(8) Uani 1 1 d . . .
O3 O 0.7117(6) 0.25458(18) 0.69579(8) 0.0582(7) Uani 1 1 d . . .
H3X H 0.6648 0.2845 0.6723 0.087 Uiso 1 1 calc R . .
F3 F 1.2459(5) 0.13846(16) 0.88244(7) 0.0648(6) Uani 1 1 d . . .
O4 O 1.0532(6) 0.41149(19) 0.71128(8) 0.0585(7) Uani 1 1 d . . .
C8 C 0.9322(8) 0.3231(3) 0.72195(12) 0.0433(8) Uani 1 1 d . . .
C9 C 1.0113(7) 0.2755(2) 0.76502(11) 0.0385(8) Uani 1 1 d . . .
C10 C 1.1925(8) 0.3354(3) 0.79978(12) 0.0453(9) Uani 1 1 d . . .
C11 C 1.2673(9) 0.2894(3) 0.83896(12) 0.0502(9) Uani 1 1 d . . .
C12 C 1.1605(8) 0.1809(3) 0.84369(11) 0.0439(8) Uani 1 1 d . . .
C13 C 0.9832(8) 0.1182(3) 0.81025(11) 0.0447(8) Uani 1 1 d . . .
H13 H 0.9132 0.0431 0.8137 0.054 Uiso 1 1 calc R . .
C14 C 0.9070(8) 0.1657(2) 0.77132(11) 0.0404(8) Uani 1 1 d . . .
H14 H 0.7796 0.1225 0.7480 0.049 Uiso 1 1 calc R . .
F4 F 0.0729(5) -0.05121(15) 0.70632(7) 0.0658(6) Uani 1 1 d . . .
F5 F -0.3335(6) -0.13086(17) 0.63578(7) 0.0667(6) Uani 1 1 d . . .
F6 F -0.6035(5) -0.34053(16) 0.62864(6) 0.0590(6) Uani 1 1 d . . .
O7 O 0.3021(6) -0.25921(18) 0.80639(8) 0.0519(6) Uani 1 1 d . . .
H7X H 0.4216 -0.2321 0.8289 0.078 Uiso 1 1 calc R . .
O8 O 0.3661(6) -0.0885(2) 0.78646(9) 0.0650(8) Uani 1 1 d . . .
C22 C 0.2465(8) -0.1816(3) 0.77917(12) 0.0429(8) Uani 1 1 d . . .
C23 C 0.0209(7) -0.2235(2) 0.73912(11) 0.0393(8) Uani 1 1 d . . .
C24 C -0.0545(8) -0.1569(3) 0.70526(12) 0.0442(9) Uani 1 1 d . . .
C25 C -0.2612(8) -0.1970(3) 0.66845(11) 0.0455(8) Uani 1 1 d . . .
C26 C -0.3991(8) -0.3049(3) 0.66533(11) 0.0425(8) Uani 1 1 d . . .
C27 C -0.3354(8) -0.3734(3) 0.69803(11) 0.0420(8) Uani 1 1 d . . .
H27 H -0.4343 -0.4474 0.6958 0.050 Uiso 1 1 calc R . .
C28 C -0.1248(7) -0.3325(2) 0.73426(11) 0.0406(8) Uani 1 1 d . . .
H28 H -0.0760 -0.3800 0.7569 0.049 Uiso 1 1 calc R . .
O5 O 0.2201(5) -0.12737(17) 1.02056(8) 0.0474(6) Uani 1 1 d . . .
N5 N -0.3133(6) -0.1832(2) 0.88044(9) 0.0382(7) Uani 1 1 d . . .
O6 O 0.2068(5) -0.45730(17) 0.95140(8) 0.0477(6) Uani 1 1 d . . .
N6 N -0.1695(6) -0.0635(2) 0.93641(8) 0.0375(7) Uani 1 1 d . . .
H6N H -0.1515 -0.0028 0.9522 0.056 Uiso 1 1 calc R . .
N7 N 0.2075(6) -0.2925(2) 0.98564(9) 0.0377(6) Uani 1 1 d . . .
N8 N -0.0544(6) -0.3321(2) 0.91353(9) 0.0397(7) Uani 1 1 d . . .
C15 C -0.3235(8) -0.0837(3) 0.89594(11) 0.0418(8) Uani 1 1 d . . .
H15 H -0.4303 -0.0314 0.8798 0.050 Uiso 1 1 calc R . .
C16 C -0.0440(7) -0.1585(2) 0.94815(11) 0.0371(8) Uani 1 1 d . . .
C17 C 0.1338(7) -0.1855(2) 0.98760(11) 0.0370(8) Uani 1 1 d . . .
C18 C 0.1227(7) -0.3659(3) 0.95009(11) 0.0389(8) Uani 1 1 d . . .
C19 C -0.1375(7) -0.2282(2) 0.91329(11) 0.0366(8) Uani 1 1 d . . .
C20 C 0.3775(8) -0.3317(3) 1.02537(11) 0.0456(9) Uani 1 1 d . . .
H20A H 0.5216 -0.3870 1.0171 0.068 Uiso 1 1 calc R . .
H20B H 0.1974 -0.3631 1.0444 0.068 Uiso 1 1 calc R . .
H20C H 0.5268 -0.2713 1.0412 0.068 Uiso 1 1 calc R . .
C21 C -0.1718(8) -0.4088(2) 0.87686(11) 0.0451(9) Uani 1 1 d . . .
H21A H -0.0858 -0.4778 0.8825 0.068 Uiso 1 1 calc R . .
H21B H -0.0794 -0.3799 0.8498 0.068 Uiso 1 1 calc R . .
H21C H -0.4291 -0.4203 0.8737 0.068 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.241(4) . ?
N1 C1 1.343(4) . ?
N1 C5 1.353(4) . ?
C1 N2 1.330(4) . ?
C1 H1 0.9500 . ?
O2 C4 1.221(4) . ?
N2 C2 1.382(4) . ?
N2 H2N 0.8800 . ?
C2 C5 1.367(4) . ?
C2 C3 1.419(4) . ?
C3 N3 1.390(4) . ?
N3 C4 1.404(4) . ?
N3 C6 1.481(4) . ?
N4 C5 1.372(4) . ?
N4 C4 1.388(4) . ?
N4 C7 1.462(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
F1 C10 1.346(4) . ?
F2 C11 1.344(4) . ?
O3 C8 1.331(4) . ?
O3 H3X 0.8400 . ?
F3 C12 1.350(4) . ?
O4 C8 1.202(4) . ?
C8 C9 1.490(5) . ?
C9 C10 1.376(4) . ?
C9 C14 1.399(4) . ?
C10 C11 1.373(5) . ?
C11 C12 1.377(5) . ?
C12 C13 1.359(4) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
F4 C24 1.344(4) . ?
F5 C25 1.353(4) . ?
F6 C26 1.356(3) . ?
O7 C22 1.326(4) . ?
O7 H7X 0.8400 . ?
O8 C22 1.201(4) . ?
C22 C23 1.494(4) . ?
C23 C24 1.386(4) . ?
C23 C28 1.401(4) . ?
C24 C25 1.377(5) . ?
C25 C26 1.378(5) . ?
C26 C27 1.365(4) . ?
C27 C28 1.373(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
O5 C17 1.225(3) . ?
N5 C15 1.325(4) . ?
N5 C19 1.353(4) . ?
O6 C18 1.230(4) . ?
N6 C15 1.339(4) . ?
N6 C16 1.389(4) . ?
N6 H6N 0.8800 . ?
N7 C18 1.394(4) . ?
N7 C17 1.404(4) . ?
N7 C20 1.471(4) . ?
N8 C18 1.378(4) . ?
N8 C19 1.379(4) . ?
N8 C21 1.461(4) . ?
C15 H15 0.9500 . ?
C16 C19 1.354(4) . ?
C16 C17 1.420(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 104.1(3) . . ?
N2 C1 N1 112.4(3) . . ?
N2 C1 H1 123.8 . . ?
N1 C1 H1 123.8 . . ?
C1 N2 C2 107.1(3) . . ?
C1 N2 H2N 126.5 . . ?
C2 N2 H2N 126.5 . . ?
C5 C2 N2 104.9(3) . . ?
C5 C2 C3 122.5(3) . . ?
N2 C2 C3 132.5(3) . . ?
O1 C3 N3 121.0(3) . . ?
O1 C3 C2 126.2(3) . . ?
N3 C3 C2 112.8(3) . . ?
C3 N3 C4 126.3(3) . . ?
C3 N3 C6 117.0(3) . . ?
C4 N3 C6 116.7(2) . . ?
C5 N4 C4 119.2(3) . . ?
C5 N4 C7 121.7(3) . . ?
C4 N4 C7 119.1(3) . . ?
O2 C4 N4 121.6(3) . . ?
O2 C4 N3 121.4(3) . . ?
N4 C4 N3 117.0(3) . . ?
N1 C5 C2 111.5(3) . . ?
N1 C5 N4 126.3(3) . . ?
C2 C5 N4 122.1(3) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 O3 H3X 109.5 . . ?
O4 C8 O3 123.3(3) . . ?
O4 C8 C9 125.1(3) . . ?
O3 C8 C9 111.6(3) . . ?
C10 C9 C14 117.1(3) . . ?
C10 C9 C8 122.5(3) . . ?
C14 C9 C8 120.4(3) . . ?
F1 C10 C11 117.1(3) . . ?
F1 C10 C9 121.5(3) . . ?
C11 C10 C9 121.5(3) . . ?
F2 C11 C10 120.0(3) . . ?
F2 C11 C12 120.5(3) . . ?
C10 C11 C12 119.5(3) . . ?
F3 C12 C13 121.1(3) . . ?
F3 C12 C11 117.6(3) . . ?
C13 C12 C11 121.3(3) . . ?
C12 C13 C14 118.5(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C9 122.1(3) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
C22 O7 H7X 109.5 . . ?
O8 C22 O7 123.0(3) . . ?
O8 C22 C23 124.7(3) . . ?
O7 C22 C23 112.3(3) . . ?
C24 C23 C28 117.0(3) . . ?
C24 C23 C22 121.9(3) . . ?
C28 C23 C22 121.1(3) . . ?
F4 C24 C25 116.8(3) . . ?
F4 C24 C23 122.1(3) . . ?
C25 C24 C23 121.1(3) . . ?
F5 C25 C24 120.3(3) . . ?
F5 C25 C26 120.0(3) . . ?
C24 C25 C26 119.6(3) . . ?
F6 C26 C27 121.0(3) . . ?
F6 C26 C25 117.5(3) . . ?
C27 C26 C25 121.5(3) . . ?
C26 C27 C28 118.3(3) . . ?
C26 C27 H27 120.9 . . ?
C28 C27 H27 120.9 . . ?
C27 C28 C23 122.6(3) . . ?
C27 C28 H28 118.7 . . ?
C23 C28 H28 118.7 . . ?
C15 N5 C19 103.3(3) . . ?
C15 N6 C16 105.5(3) . . ?
C15 N6 H6N 127.2 . . ?
C16 N6 H6N 127.2 . . ?
C18 N7 C17 126.0(3) . . ?
C18 N7 C20 117.1(3) . . ?
C17 N7 C20 116.8(3) . . ?
C18 N8 C19 119.3(3) . . ?
C18 N8 C21 119.6(3) . . ?
C19 N8 C21 120.9(3) . . ?
N5 C15 N6 113.8(3) . . ?
N5 C15 H15 123.1 . . ?
N6 C15 H15 123.1 . . ?
C19 C16 N6 105.1(3) . . ?
C19 C16 C17 124.2(3) . . ?
N6 C16 C17 130.7(3) . . ?
O5 C17 N7 120.8(3) . . ?
O5 C17 C16 127.5(3) . . ?
N7 C17 C16 111.6(3) . . ?
O6 C18 N8 121.4(3) . . ?
O6 C18 N7 120.8(3) . . ?
N8 C18 N7 117.8(3) . . ?
N5 C19 C16 112.3(3) . . ?
N5 C19 N8 126.6(3) . . ?
C16 C19 N8 121.1(3) . . ?
N7 C20 H20A 109.5 . . ?
N7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C21 H21A 109.5 . . ?
N8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.892
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.892
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.063

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

data_thp-235triFBA
_database_code_depnum_ccdc_archive 'CCDC 1451265'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_systematic        
; ?
;
_chemical_name_common            'theophylline:2,3,5-trifluorobenzoic acid'
_chemical_formula_moiety         '(C7 H8 N4 O2), (C7 H3 F3 O2)'
_chemical_formula_structural     '(C7 H8 N4 O2), (C7 H3 F3 O2)'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C14 H11 F3 N4 O4'
_chemical_formula_weight         356.26
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and 
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_length_neutron # include if applicable
? ? ? ? ? ?

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-p 2ybc'

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

_cell_length_a                   3.91876(24)
_cell_length_b                   13.1931(12)
_cell_length_c                   28.9207(30)
_cell_angle_alpha                90
_cell_angle_beta                 91.1151(67)
_cell_angle_gamma                90
_cell_volume                     1494.93(29)
_cell_formula_units_Z            4
_cell_measurement_theta_min      3
_cell_measurement_theta_max      60
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293
_exptl_crystal_density_diffrn    1.5829(3)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

_cell_special_details            
; ?
;

# The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              14 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              10 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              0.5 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 'packed powder pellet'
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet

_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions



_pd_prep_temperature             293


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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_measurement_device_type  "Panalytical X'pert Powder"
_diffrn_detector                 ?
_diffrn_detector_type            X'Celerator # make or model of detector

_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  none

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        5875
_pd_meas_2theta_range_min        3.00
_pd_meas_2theta_range_max        50.00
_pd_meas_2theta_range_inc        0.008



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

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_pref_orient_corr     
; 'Spherical harmonics'
;

_pd_proc_ls_prof_R_factor        0.045
_pd_proc_ls_prof_wR_factor       0.057
_pd_proc_ls_prof_wR_expected     0.011
_refine_ls_R_I_factor            0.023


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     41
_refine_ls_number_restraints     0
_refine_ls_number_constraints    96

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   4.995


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        55
_pd_proc_2theta_range_inc        0.008
_pd_proc_wavelength              1.5418

# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting 
# of one data block containing a single powder profile. The value of 
# _pd_block_diffractogram_id is used to associate each refinement with 
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template 
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given 
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?




# The following items are used to identify the programs used.

_computing_data_collection       "X'Pert Data Collector (Panalytical )"
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'TOPAS Academic (Coelho 2007)'
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C2 C 0.2115(17) 0.66377(42) 0.02215(19) 1 7.79(26)
N2 N 0.3821(21) 0.60844(59) 0.05586(31) 1 7.79(26)
C1 C 0.3579(25) 0.66064(81) 0.09569(23) 1 7.79(26)
N1 N 0.1809(25) 0.74714(75) 0.09028(13) 1 7.79(26)
C6 C 0.0896(19) 0.74931(49) 0.04466(13) 1 7.79(26)
N4 N -0.0976(19) 0.82246(45) 0.02253(23) 1 7.79(26)
C5 C -0.1765(19) 0.81185(53) -0.02451(24) 1 7.79(26)
N3 N -0.0429(20) 0.72512(58) -0.04677(13) 1 7.79(26)
C3 C 0.1527(20) 0.64775(45) -0.02616(20) 1 7.79(26)
C7 C -0.2110(27) 0.91215(57) 0.04797(39) 1 7.79(26)
O2 O -0.3557(23) 0.87365(69) -0.04538(37) 1 7.79(26)
C4 C -0.1108(29) 0.71466(89) -0.09672(14) 1 7.79(26)
O1 O 0.2548(27) 0.57534(57) -0.04985(32) 1 7.79(26)
H1 H 0.4564(30) 0.6395(10) 0.12382(29) 1 7.79(26)
H2 H 0.4934(23) 0.55004(61) 0.05238(43) 1 7.79(26)
H3 H 0.0990(32) 0.71135(96) -0.11237(13) 1 7.79(26)
H4 H -0.2339(31) 0.65391(96) -0.10238(16) 1 7.79(26)
H5 H -0.2378(30) 0.77150(99) -0.10679(21) 1 7.79(26)
H6 H -0.0236(31) 0.95573(55) 0.05454(40) 1 7.79(26)
H7 H -0.3738(28) 0.94734(59) 0.02967(49) 1 7.79(26)
H8 H -0.3103(29) 0.89140(73) 0.07602(39) 1 7.79(26)
F1 F 0.4665(22) -0.07908(59) -0.15464(17) 1 7.79(26)
C10 C 0.3559(16) -0.05365(45) -0.19726(15) 1 7.79(26)
C11 C 0.2056(18) -0.13006(44) -0.22456(20) 1 7.79(26)
F2 F 0.1854(28) -0.22428(44) -0.20671(30) 1 7.79(26)
C12 C 0.0767(16) -0.11107(57) -0.26884(19) 1 7.79(26)
H10 H -0.0254(19) -0.16341(67) -0.28629(25) 1 7.79(26)
C13 C 0.1030(13) -0.01183(62) -0.28514(16) 1 7.79(26)
F3 F -0.0198(18) 0.00840(86) -0.32844(18) 1 7.79(26)
C14 C 0.2461(14) 0.06635(50) -0.25909(18) 1 7.79(26)
H11 H 0.2556(20) 0.13284(55) -0.27057(24) 1 7.79(26)
C9 C 0.3764(13) 0.04590(44) -0.21433(16) 1 7.79(26)
C8 C 0.5128(18) 0.13361(51) -0.18649(24) 1 7.79(26)
O4 O 0.4145(25) 0.22093(47) -0.19320(33) 1 7.79(26)
O3 O 0.7446(19) 0.10835(71) -0.15442(23) 1 7.79(26)
H9 H 0.7920(23) 0.16232(80) -0.13748(28) 1 7.79(26)

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


# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N2 1.38(1)
C2 C6 1.392(8)
C2 C3 1.427(8)
N2 C1 1.35(1)
N2 H2 0.89(1)
C1 N1 1.34(1)
C1 H1 0.94(1)
N1 C6 1.361(6)
C6 N4 1.364(9)
N4 C5 1.40(1)
N4 C7 1.47(1)
C5 N3 1.42(1)
C5 O2 1.23(1)
N3 C3 1.40(1)
N3 C4 1.470(6)
C3 O1 1.25(1)
C7 H6 0.95(1)
C7 H7 0.94(2)
C7 H8 0.95(2)
C4 H3 0.95(2)
C4 H4 0.95(2)
C4 H5 0.94(2)
F1 C10 1.341(7)
C10 C11 1.403(8)
C10 C9 1.406(8)
C11 F2 1.349(9)
C11 C12 1.390(8)
C12 H10 0.94(1)
C12 C13 1.40(1)
C13 F3 1.359(8)
C13 C14 1.389(9)
C14 H11 0.94(1)
C14 C9 1.408(7)
C9 C8 1.502(9)
C8 O4 1.23(1)
C8 O3 1.33(1)
O3 H9 0.88(1)


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C2 C6 105.3(6)
N2 C2 C3 132.8(6)
C6 C2 C3 121.8(6)
C2 N2 C1 107.0(7)
C2 N2 H2 127(1)
C1 N2 H2 126(1)
N2 C1 N1 112.3(8)
N2 C1 H1 124(1)
N1 C1 H1 124(1)
C1 N1 C6 104.9(7)
C2 C6 N1 110.5(6)
C2 C6 N4 122.7(6)
N1 C6 N4 126.8(6)
C6 N4 C5 119.5(6)
C6 N4 C7 120.1(7)
C5 N4 C7 120.4(7)
N4 C5 N3 116.5(6)
N4 C5 O2 121.8(8)
N3 C5 O2 121.7(8)
C5 N3 C3 126.7(6)
C5 N3 C4 117.4(6)
C3 N3 C4 115.9(6)
C2 C3 N3 112.6(6)
C2 C3 O1 127.2(7)
N3 C3 O1 120.2(7)
N4 C7 H6 110(1)
N4 C7 H7 109(1)
N4 C7 H8 109(1)
H6 C7 H7 109(1)
H6 C7 H8 109(1)
H7 C7 H8 110(1)
N3 C4 H3 109(1)
N3 C4 H4 109(1)
N3 C4 H5 108(1)
H3 C4 H4 109(1)
H3 C4 H5 110(1)
H4 C4 H5 111(1)
F1 C10 C11 117.5(6)
F1 C10 C9 122.5(5)
C11 C10 C9 120.0(5)
C10 C11 F2 118.3(6)
C10 C11 C12 122.0(6)
F2 C11 C12 119.7(6)
C11 C12 H10 120.4(8)
C11 C12 C13 116.9(6)
H10 C12 C13 122.8(8)
C12 C13 F3 117.9(6)
C12 C13 C14 123.0(6)
F3 C13 C14 119.1(6)
C13 C14 H11 121.4(7)
C13 C14 C9 119.4(5)
H11 C14 C9 119.2(7)
C10 C9 C14 118.7(5)
C10 C9 C8 123.6(5)
C14 C9 C8 117.6(5)
C9 C8 O4 122.0(7)
C9 C8 O3 114.4(6)
O4 C8 O3 123.6(8)
C8 O3 H9 109(1)
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_thp-236triFBA
_database_code_depnum_ccdc_archive 'CCDC 1451266'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_systematic        
; ?
;
_chemical_name_common            'theophylline:2,3,5-trifluorobenzoic acid'
_chemical_formula_moiety         '(C7 H8 N4 O2), (C7 H3 F3 O2)'
_chemical_formula_structural     '(C7 H8 N4 O2), (C7 H3 F3 O2)'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C14 H11 F3 N4 O4'
_chemical_formula_weight         356.26
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and 
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_length_neutron # include if applicable
? ? ? ? ? ?

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   3.96986(28)
_cell_length_b                   13.0525(13)
_cell_length_c                   29.1541(34)
_cell_angle_alpha                90
_cell_angle_beta                 90.7519(70)
_cell_angle_gamma                90
_cell_volume                     1510.54(36)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_theta_min      3
_cell_measurement_theta_max      60
_cell_measurement_reflns_used    20
_exptl_crystal_density_diffrn    1.5666(4)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

_cell_special_details            
; ?
;

# The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              14 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              10 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              0.5 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 'packed powder pellet'
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet

_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions



_pd_prep_temperature             293


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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_measurement_device_type  "Panalytical X'pert Powder"
_diffrn_detector                 ?
_diffrn_detector_type            X'Celerator # make or model of detector

_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  none

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        1728
_pd_meas_2theta_range_min        3.00
_pd_meas_2theta_range_max        60.00
_pd_meas_2theta_range_inc        0.033



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

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_pref_orient_corr     
;
;

_pd_proc_ls_prof_R_factor        0.052
_pd_proc_ls_prof_wR_factor       0.065
_pd_proc_ls_prof_wR_expected     0.011
_refine_ls_R_I_factor            0.021


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     43
_refine_ls_number_restraints     0
_refine_ls_number_constraints    96

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   5.969


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        55
_pd_proc_2theta_range_inc        0.033
_pd_proc_wavelength              1.5418

# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting 
# of one data block containing a single powder profile. The value of 
# _pd_block_diffractogram_id is used to associate each refinement with 
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template 
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given 
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?




# The following items are used to identify the programs used.

_computing_data_collection       "X'Pert Data Collector (Panalytical )"
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'TOPAS Academic (Coelho 2007)'
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C2 C -0.7822(15) 0.65847(41) 0.02253(20) 1 4.98(22)
N2 N -0.6152(19) 0.60102(65) 0.05540(30) 1 4.98(22)
C1 C -0.6291(22) 0.65395(93) 0.09498(24) 1 4.98(22)
N1 N -0.7954(23) 0.74297(86) 0.09017(18) 1 4.98(22)
C6 C -0.8907(16) 0.74598(51) 0.04526(19) 1 4.98(22)
N4 N -1.0713(19) 0.82152(44) 0.02398(30) 1 4.98(22)
C5 C -1.1567(17) 0.81145(49) -0.02235(30) 1 4.98(22)
N3 N -1.0303(17) 0.72391(56) -0.04512(19) 1 4.98(22)
C3 C -0.8456(18) 0.64330(43) -0.02526(21) 1 4.98(22)
C7 C -1.1939(30) 0.91940(59) 0.04199(48) 1 4.98(22)
O2 O -1.3337(22) 0.87471(69) -0.04234(44) 1 4.98(22)
C4 C -1.0968(25) 0.71595(94) -0.09469(19) 1 4.98(22)
O1 O -0.7542(28) 0.56936(60) -0.04914(32) 1 4.98(22)
H1 H -0.5321(27) 0.6317(12) 0.12266(28) 1 4.98(22)
H2 H -0.5131(24) 0.54077(69) 0.05175(42) 1 4.98(22)
H3 H -1.2445(29) 0.6602(10) -0.10065(21) 1 4.98(22)
H4 H -0.8909(29) 0.7037(11) -0.10977(17) 1 4.98(22)
H5 H -1.1942(26) 0.7781(10) -0.10480(27) 1 4.98(22)
H6 H -1.3168(32) 0.90821(84) 0.06922(49) 1 4.98(22)
H7 H -1.0069(35) 0.96264(55) 0.04833(51) 1 4.98(22)
H8 H -1.3355(31) 0.95021(61) 0.01975(56) 1 4.98(22)
F1 F -0.6299(24) 0.15002(58) -0.28244(25) 1 4.98(22)
C10 C -0.7064(15) 0.06043(44) -0.26164(21) 1 4.98(22)
C11 C -0.8577(15) -0.01676(58) -0.28804(25) 1 4.98(22)
F2 F -0.9226(20) 0.00172(88) -0.33301(24) 1 4.98(22)
C12 C -0.9408(18) -0.11080(49) -0.26883(35) 1 4.98(22)
H10 H -1.0464(22) -0.16222(61) -0.28704(42) 1 4.98(22)
C13 C -0.8684(23) -0.12799(36) -0.22243(36) 1 4.98(22)
F3 F -0.6515(27) -0.07015(65) -0.15185(29) 1 4.98(22)
C14 C -0.7129(20) -0.05126(40) -0.19659(27) 1 4.98(22)
H11 H -0.9229(30) -0.19190(41) -0.20883(45) 1 4.98(22)
C9 C -0.6287(15) 0.04530(36) -0.21490(21) 1 4.98(22)
C8 C -0.4892(20) 0.13160(49) -0.18626(26) 1 4.98(22)
O4 O -0.6119(26) 0.21786(45) -0.18684(33) 1 4.98(22)
O3 O -0.2270(21) 0.10482(75) -0.16025(29) 1 4.98(22)
H9 H -0.1893(25) 0.15355(89) -0.13423(33) 1 4.98(22)


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


# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N2 1.38(1)
C2 C6 1.392(8)
C2 C3 1.426(8)
N2 C1 1.35(1)
N2 H2 0.89(1)
C1 N1 1.34(2)
C1 H1 0.94(1)
N1 C6 1.359(8)
C6 N4 1.364(9)
N4 C5 1.39(1)
N4 C7 1.47(1)
C5 N3 1.42(1)
C5 O2 1.23(1)
N3 C3 1.403(9)
N3 C4 1.469(8)
C3 O1 1.25(1)
C7 H6 0.95(2)
C7 H7 0.95(2)
C7 H8 0.94(2)
C4 H3 0.95(2)
C4 H4 0.95(1)
C4 H5 0.94(2)
F1 C10 1.35(1)
C10 C11 1.399(9)
C10 C9 1.407(9)
C11 F2 1.35(1)
C11 C12 1.39(1)
C12 H10 0.95(1)
C12 C13 1.40(1)
C13 C14 1.39(1)
C13 H11 0.95(1)
F3 C14 1.35(1)
C14 C9 1.411(8)
C9 C8 1.504(9)
C8 O4 1.227(9)
C8 O3 1.33(1)
O3 H9 1.00(1)


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C2 C6 105.3(6)
N2 C2 C3 132.8(6)
C6 C2 C3 121.8(5)
C2 N2 C1 107.0(7)
C2 N2 H2 128(1)
C1 N2 H2 125(1)
N2 C1 N1 112.3(8)
N2 C1 H1 124(1)
N1 C1 H1 124(1)
C1 N1 C6 104.8(7)
C2 C6 N1 110.6(6)
C2 C6 N4 122.8(6)
N1 C6 N4 126.7(7)
C6 N4 C5 119.5(7)
C6 N4 C7 129.9(7)
C5 N4 C7 110.6(7)
N4 C5 N3 116.5(6)
N4 C5 O2 121.8(8)
N3 C5 O2 121.6(8)
C5 N3 C3 126.7(6)
C5 N3 C4 117.2(6)
C3 N3 C4 116.0(6)
C2 C3 N3 112.6(6)
C2 C3 O1 127.2(7)
N3 C3 O1 120.3(7)
N4 C7 H6 110(1)
N4 C7 H7 109(1)
N4 C7 H8 109(1)
H6 C7 H7 110(2)
H6 C7 H8 109(2)
H7 C7 H8 110(2)
N3 C4 H3 110(1)
N3 C4 H4 109(1)
N3 C4 H5 108(1)
H3 C4 H4 109(1)
H3 C4 H5 111(1)
H4 C4 H5 111(1)
F1 C10 C11 118.2(6)
F1 C10 C9 120.5(6)
C11 C10 C9 121.3(6)
C10 C11 F2 118.6(7)
C10 C11 C12 121.1(6)
F2 C11 C12 120.3(7)
C11 C12 H10 120(1)
C11 C12 C13 119.0(7)
H10 C12 C13 121(1)
C12 C13 C14 119.5(7)
C12 C13 H11 120(1)
C14 C13 H11 121(1)
C13 C14 F3 117.8(7)
C13 C14 C9 122.9(6)
F3 C14 C9 119.3(7)
C10 C9 C14 116.2(5)
C10 C9 C8 120.5(5)
C14 C9 C8 123.1(6)
C9 C8 O4 122.5(7)
C9 C8 O3 113.6(7)
O4 C8 O3 123.9(8)
C8 O3 H9 112(1)

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

data_thp-245triFBA-I
_database_code_depnum_ccdc_archive 'CCDC 1451267'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2016-01-15T17:28:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C7 H8 N4 O2, C7 H3 F3 O2'
_chemical_formula_sum            'C14 H11 F3 N4 O4'
_chemical_formula_weight         356.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   4.7579(4)
_cell_length_b                   12.5624(11)
_cell_length_c                   13.4092(11)
_cell_angle_alpha                76.403(7)
_cell_angle_beta                 80.880(7)
_cell_angle_gamma                82.885(7)
_cell_volume                     766.03(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1596
_cell_measurement_theta_min      4.4070
_cell_measurement_theta_max      72.4710

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364



#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.81427
_exptl_absorpt_correction_T_max  1.00000

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_number            4098
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             2659
_reflns_number_gt                1970
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0767P)²+0.0114P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2659
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3612(5) 0.26897(19) 1.14236(17) 0.0542(6) Uani 1 1 d . . . . .
H1 H 0.2805 0.2448 1.2106 0.065 Uiso 1 1 calc R U . . .
C2 C 0.6374(4) 0.28096(17) 1.00047(15) 0.0424(5) Uani 1 1 d . . . . .
C3 C 0.8645(4) 0.33376(19) 0.82806(16) 0.0472(5) Uani 1 1 d . . . . .
C4 C 0.4173(4) 0.44063(18) 0.88735(16) 0.0439(5) Uani 1 1 d . . . . .
C5 C 0.4284(4) 0.36548(17) 0.98459(15) 0.0426(5) Uani 1 1 d . . . . .
C6 C 1.0565(5) 0.1650(2) 0.93951(19) 0.0571(6) Uani 1 1 d . . . . .
H6A H 1.1141 0.1522 1.0071 0.086 Uiso 1 1 calc R U . . .
H6B H 1.2212 0.176 0.8879 0.086 Uiso 1 1 calc R U . . .
H6C H 0.9679 0.1025 0.9337 0.086 Uiso 1 1 calc R U . . .
C7 C 0.6631(6) 0.4937(2) 0.71083(18) 0.0668(7) Uani 1 1 d . . . . .
H7A H 0.6212 0.4553 0.6617 0.1 Uiso 1 1 calc R U . . .
H7B H 0.852 0.5174 0.6907 0.1 Uiso 1 1 calc R U . . .
H7C H 0.5269 0.5566 0.7126 0.1 Uiso 1 1 calc R U . . .
N1 N 0.5991(4) 0.22045(16) 1.09888(14) 0.0516(5) Uani 1 1 d . . . . .
N2 N 0.8524(3) 0.26307(15) 0.92393(13) 0.0460(4) Uani 1 1 d . . . . .
N3 N 0.6463(3) 0.41996(15) 0.81416(13) 0.0463(4) Uani 1 1 d . . . . .
N4 N 0.2512(4) 0.35618(16) 1.07714(14) 0.0488(4) Uani 1 1 d . . . . .
H1N H 0.091(6) 0.399(2) 1.093(2) 0.073 Uiso 1 1 d . U . . .
O1 O 1.0536(3) 0.32290(15) 0.75818(12) 0.0620(5) Uani 1 1 d . . . . .
O2 O 0.2336(3) 0.51721(13) 0.86616(12) 0.0550(4) Uani 1 1 d . . . . .
C8 C -0.1717(5) 1.02201(19) 0.30466(17) 0.0510(5) Uani 1 1 d . . . . .
C9 C -0.0009(4) 0.92479(18) 0.36006(16) 0.0468(5) Uani 1 1 d . . . . .
C10 C 0.2407(4) 0.8708(2) 0.31662(16) 0.0500(5) Uani 1 1 d . . . . .
C11 C 0.3877(5) 0.7798(2) 0.37071(18) 0.0611(6) Uani 1 1 d . . . . .
H11 H 0.5495 0.7449 0.339 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2869(6) 0.7427(2) 0.4726(2) 0.0676(7) Uani 1 1 d . . . . .
C14 C -0.0934(5) 0.8841(2) 0.46442(18) 0.0577(6) Uani 1 1 d . . . . .
H14 H -0.2537 0.9186 0.4973 0.069 Uiso 1 1 calc R U . . .
1C3 C 0.0505(6) 0.7937(2) 0.51882(18) 0.0650(7) Uani 1 1 d . . . . .
F1 F 0.3461(3) 0.90483(14) 0.21594(10) 0.0714(4) Uani 1 1 d . . . . .
F2 F 0.4250(4) 0.65407(17) 0.52782(15) 0.1093(7) Uani 1 1 d . . . . .
F3 F -0.0383(4) 0.75300(17) 0.61994(12) 0.1029(7) Uani 1 1 d . . . . .
O3 O -0.0829(4) 1.05073(17) 0.20487(13) 0.0704(5) Uani 1 1 d . . . . .
H1O H -0.214(7) 1.107(3) 0.175(3) 0.106 Uiso 1 1 d . U . . .
O4 O -0.3768(4) 1.06747(17) 0.34703(15) 0.0807(6) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.334(3) . ?
C1 N4 1.339(3) . ?
C1 H1 0.93 . ?
C2 N1 1.356(3) . ?
C2 C5 1.364(3) . ?
C2 N2 1.367(3) . ?
C3 O1 1.212(3) . ?
C3 N2 1.377(3) . ?
C3 N3 1.405(3) . ?
C4 O2 1.230(3) . ?
C4 N3 1.389(3) . ?
C4 C5 1.423(3) . ?
C5 N4 1.374(3) . ?
C6 N2 1.467(3) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C7 N3 1.471(3) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
N4 H1N 0.90(3) . ?
C8 O4 1.200(3) . ?
C8 O3 1.316(3) . ?
C8 C9 1.491(3) . ?
C9 C10 1.379(3) . ?
C9 C14 1.392(3) . ?
C10 F1 1.351(3) . ?
C10 C11 1.377(3) . ?
C11 C12 1.364(4) . ?
C11 H11 0.93 . ?
C12 F2 1.343(3) . ?
C12 1C3 1.359(4) . ?
C14 1C3 1.366(4) . ?
C14 H14 0.93 . ?
1C3 F3 1.351(3) . ?
O3 H1O 0.94(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 112.8(2) . . ?
N1 C1 H1 123.6 . . ?
N4 C1 H1 123.6 . . ?
N1 C2 C5 111.28(17) . . ?
N1 C2 N2 126.55(18) . . ?
C5 C2 N2 122.16(19) . . ?
O1 C3 N2 122.09(19) . . ?
O1 C3 N3 120.9(2) . . ?
N2 C3 N3 117.01(17) . . ?
O2 C4 N3 121.14(19) . . ?
O2 C4 C5 126.51(19) . . ?
N3 C4 C5 112.34(17) . . ?
C2 C5 N4 105.53(18) . . ?
C2 C5 C4 122.52(18) . . ?
N4 C5 C4 131.93(18) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 N1 C2 103.97(17) . . ?
C2 N2 C3 119.44(16) . . ?
C2 N2 C6 121.06(18) . . ?
C3 N2 C6 119.30(17) . . ?
C4 N3 C3 126.45(17) . . ?
C4 N3 C7 117.64(17) . . ?
C3 N3 C7 115.90(17) . . ?
C1 N4 C5 106.46(18) . . ?
C1 N4 H1N 125.0(19) . . ?
C5 N4 H1N 128.6(19) . . ?
O4 C8 O3 123.3(2) . . ?
O4 C8 C9 122.8(2) . . ?
O3 C8 C9 113.90(19) . . ?
C10 C9 C14 116.9(2) . . ?
C10 C9 C8 125.6(2) . . ?
C14 C9 C8 117.5(2) . . ?
F1 C10 C11 115.8(2) . . ?
F1 C10 C9 120.88(19) . . ?
C11 C10 C9 123.4(2) . . ?
C12 C11 C10 117.4(2) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
F2 C12 1C3 119.7(3) . . ?
F2 C12 C11 119.1(3) . . ?
1C3 C12 C11 121.2(2) . . ?
1C3 C14 C9 120.3(2) . . ?
1C3 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
F3 1C3 C12 118.4(2) . . ?
F3 1C3 C14 120.8(2) . . ?
C12 1C3 C14 120.8(2) . . ?
C8 O3 H1O 108(2) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

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

data_thp-245tri-FBA-II
_database_code_depnum_ccdc_archive 'CCDC 1451268'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2016-01-15T17:55:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C7 H8 N4 O2, C7 H3 F3 O2'
_chemical_formula_sum            'C14 H11 F3 N4 O4'
_chemical_formula_weight         356.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8186(5)
_cell_length_b                   8.6806(5)
_cell_length_c                   12.9733(7)
_cell_angle_alpha                83.266(4)
_cell_angle_beta                 88.380(5)
_cell_angle_gamma                68.110(6)
_cell_volume                     707.51(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    3495
_cell_measurement_theta_min      5.5350
_cell_measurement_theta_max      74.4300

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.069
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_F_000             364

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#


_exptl_absorpt_coefficient_mu    1.32
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.70916
_exptl_absorpt_correction_T_max  1.00000

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_number            4211
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.431
_diffrn_reflns_theta_max         66.6
_diffrn_reflns_theta_full        66.6
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_coverage         0
_reflns_number_total             2479
_reflns_number_gt                2290
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0793P)²+0.2438P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2479
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7720(3) 0.3669(2) 0.32021(14) 0.0204(4) Uani 1 1 d . . . . .
H1 H 0.7903 0.2547 0.3335 0.024 Uiso 1 1 calc R U . . .
C2 C 0.7301(2) 0.6142(2) 0.34105(13) 0.0152(4) Uani 1 1 d . . . . .
C3 C 0.6829(2) 0.9022(2) 0.31878(13) 0.0162(4) Uani 1 1 d . . . . .
C4 C 0.7073(2) 0.7509(2) 0.16333(13) 0.0154(4) Uani 1 1 d . . . . .
C5 C 0.7332(2) 0.6084(2) 0.23596(13) 0.0152(4) Uani 1 1 d . . . . .
C6 C 0.7101(3) 0.7587(2) 0.49591(14) 0.0262(4) Uani 1 1 d . . . . .
H6A H 0.5956 0.7312 0.5263 0.039 Uiso 1 1 calc R U . . .
H6B H 0.6964 0.8676 0.5115 0.039 Uiso 1 1 calc R U . . .
H6C H 0.842 0.6776 0.5238 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6294(3) 1.0530(2) 0.14516(14) 0.0222(4) Uani 1 1 d . . . . .
H7A H 0.7589 1.0712 0.1324 0.033 Uiso 1 1 calc R U . . .
H7B H 0.5329 1.1428 0.1795 0.033 Uiso 1 1 calc R U . . .
H7C H 0.5677 1.049 0.0804 0.033 Uiso 1 1 calc R U . . .
N1 N 0.7535(2) 0.46421(17) 0.39463(11) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.7046(2) 0.75804(17) 0.38309(11) 0.0166(3) Uani 1 1 d . . . . .
N3 N 0.6732(2) 0.89379(17) 0.21141(11) 0.0162(3) Uani 1 1 d . . . . .
N4 N 0.7616(2) 0.44623(18) 0.22375(12) 0.0182(3) Uani 1 1 d . . . . .
H4N H 0.776(3) 0.400(3) 0.1649(18) 0.021(5) Uiso 1 1 d . . . . .
O1 O 0.6697(2) 1.03051(15) 0.35141(10) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.7103(2) 0.75732(15) 0.06740(9) 0.0219(3) Uani 1 1 d . . . . .
C8 C 0.2311(3) 0.5831(2) 0.06225(13) 0.0190(4) Uani 1 1 d . . . . .
C9 C 0.2179(2) 0.6691(2) 0.15672(13) 0.0180(4) Uani 1 1 d . . . . .
C10 C 0.2307(3) 0.5939(2) 0.25882(14) 0.0194(4) Uani 1 1 d . . . . .
C11 C 0.2178(3) 0.6802(2) 0.34370(14) 0.0226(4) Uani 1 1 d . . . . .
H11 H 0.2281 0.6271 0.411 0.027 Uiso 1 1 calc R U . . .
C12 C 0.1895(3) 0.8461(2) 0.32561(15) 0.0232(4) Uani 1 1 d . . . . .
C13 C 0.1758(3) 0.9251(2) 0.22503(15) 0.0223(4) Uani 1 1 d . . . . .
C14 C 0.1914(3) 0.8377(2) 0.14194(14) 0.0200(4) Uani 1 1 d . . . . .
H14 H 0.1842 0.8912 0.0749 0.024 Uiso 1 1 calc R U . . .
F1 F 0.25953(18) 0.43167(13) 0.27882(8) 0.0279(3) Uani 1 1 d . . . . .
F2 F 0.17557(19) 0.93404(15) 0.40549(9) 0.0358(3) Uani 1 1 d . . . . .
F3 F 0.14774(19) 1.08806(14) 0.21099(10) 0.0340(3) Uani 1 1 d . . . . .
O3 O 0.2223(2) 0.43450(16) 0.08060(10) 0.0260(3) Uani 1 1 d . . . . .
H3O H 0.235(4) 0.392(3) 0.024(2) 0.043(7) Uiso 1 1 d . . . . .
O4 O 0.2469(2) 0.65031(17) -0.02353(10) 0.0291(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.329(2) . ?
C1 N4 1.346(2) . ?
C2 N1 1.358(2) . ?
C2 C5 1.370(2) . ?
C2 N2 1.370(2) . ?
C3 O1 1.209(2) . ?
C3 N2 1.381(2) . ?
C3 N3 1.408(2) . ?
C4 O2 1.239(2) . ?
C4 N3 1.393(2) . ?
C4 C5 1.422(2) . ?
C5 N4 1.376(2) . ?
C6 N2 1.466(2) . ?
C7 N3 1.472(2) . ?
C8 O4 1.216(2) . ?
C8 O3 1.308(2) . ?
C8 C9 1.492(2) . ?
C9 C14 1.396(3) . ?
C9 C10 1.396(3) . ?
C10 F1 1.341(2) . ?
C10 C11 1.386(3) . ?
C11 C12 1.373(3) . ?
C12 F2 1.338(2) . ?
C12 C13 1.390(3) . ?
C13 F3 1.345(2) . ?
C13 C14 1.369(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 113.57(15) . . ?
N1 C2 C5 111.89(15) . . ?
N1 C2 N2 126.16(16) . . ?
C5 C2 N2 121.94(16) . . ?
O1 C3 N2 122.77(16) . . ?
O1 C3 N3 120.83(15) . . ?
N2 C3 N3 116.39(14) . . ?
O2 C4 N3 120.48(15) . . ?
O2 C4 C5 127.09(16) . . ?
N3 C4 C5 112.42(15) . . ?
C2 C5 N4 105.23(14) . . ?
C2 C5 C4 122.47(16) . . ?
N4 C5 C4 132.29(16) . . ?
C1 N1 C2 103.28(14) . . ?
C2 N2 C3 119.85(14) . . ?
C2 N2 C6 120.64(14) . . ?
C3 N2 C6 119.44(14) . . ?
C4 N3 C3 126.55(14) . . ?
C4 N3 C7 118.13(14) . . ?
C3 N3 C7 115.29(14) . . ?
C1 N4 C5 106.03(14) . . ?
O4 C8 O3 124.52(16) . . ?
O4 C8 C9 121.05(15) . . ?
O3 C8 C9 114.42(15) . . ?
C14 C9 C10 117.46(16) . . ?
C14 C9 C8 117.50(15) . . ?
C10 C9 C8 125.04(16) . . ?
F1 C10 C11 116.82(16) . . ?
F1 C10 C9 120.70(16) . . ?
C11 C10 C9 122.48(17) . . ?
C12 C11 C10 118.12(17) . . ?
F2 C12 C11 119.97(17) . . ?
F2 C12 C13 119.08(17) . . ?
C11 C12 C13 120.96(17) . . ?
F3 C13 C14 120.86(17) . . ?
F3 C13 C12 118.90(17) . . ?
C14 C13 C12 120.24(17) . . ?
C13 C14 C9 120.74(17) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

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

data_thp-246triFBA-I
_database_code_depnum_ccdc_archive 'CCDC 1451269'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2016-01-15T17:40:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C7 H8 N4 O2, C7 H3 F3 O2'
_chemical_formula_sum            'C14 H11 F3 N4 O4'
_chemical_formula_weight         356.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4182(8)
_cell_length_b                   7.4269(9)
_cell_length_c                   13.9216(14)
_cell_angle_alpha                79.224(9)
_cell_angle_beta                 88.766(8)
_cell_angle_gamma                78.749(9)
_cell_volume                     738.91(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1947
_cell_measurement_theta_min      6.0550
_cell_measurement_theta_max      73.0040

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.051
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             364

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.92532
_exptl_absorpt_correction_T_max  1.00000


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_number            4018
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         66.539
_diffrn_reflns_theta_full        66.539
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_reflns_Friedel_coverage         0
_reflns_number_total             2562
_reflns_number_gt                1965
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.0719P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2562
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.2
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1871(3) 0.5272(4) 0.80265(17) 0.0484(6) Uani 1 1 d . . . . .
H1 H -0.2322 0.6043 0.7442 0.058 Uiso 1 1 calc R U . . .
C2 C -0.0070(3) 0.3415(3) 0.91087(14) 0.0358(4) Uani 1 1 d . . . . .
C3 C 0.1216(3) 0.1387(3) 1.05599(15) 0.0387(5) Uani 1 1 d . . . . .
C4 C -0.2079(3) 0.2989(3) 1.05102(16) 0.0400(5) Uani 1 1 d . . . . .
C5 C -0.1744(3) 0.3784(3) 0.95278(15) 0.0377(5) Uani 1 1 d . . . . .
C6 C 0.3233(3) 0.1937(4) 0.91654(18) 0.0507(6) Uani 1 1 d . . . . .
H6A H 0.3206 0.2735 0.8536 0.076 Uiso 1 1 calc R U . . .
H6B H 0.3569 0.0655 0.9092 0.076 Uiso 1 1 calc R U . . .
H6C H 0.4119 0.2212 0.9582 0.076 Uiso 1 1 calc R U . . .
C7 C -0.0666(3) 0.0908(4) 1.19958(16) 0.0497(6) Uani 1 1 d . . . . .
H7A H -0.1893 0.1286 1.2216 0.075 Uiso 1 1 calc R U . . .
H7B H 0.0188 0.1282 1.239 0.075 Uiso 1 1 calc R U . . .
H7C H -0.0389 -0.0426 1.2052 0.075 Uiso 1 1 calc R U . . .
C8 C 0.1394(3) 0.6526(4) 0.59892(16) 0.0473(6) Uani 1 1 d . . . . .
N1 N -0.0134(3) 0.4347(3) 0.81609(13) 0.0449(5) Uani 1 1 d . . . . .
N2 N 0.1411(2) 0.2258(3) 0.96029(13) 0.0383(4) Uani 1 1 d . . . . .
N3 N -0.0522(2) 0.1801(3) 1.09669(12) 0.0384(4) Uani 1 1 d . . . . .
N4 N -0.2881(3) 0.4974(3) 0.88155(14) 0.0439(5) Uani 1 1 d . . . . .
H1N H -0.406(4) 0.551(4) 0.889(2) 0.057(8) Uiso 1 1 d . . . . .
O1 O 0.2475(2) 0.0316(3) 1.10260(12) 0.0542(5) Uani 1 1 d . . . . .
O2 O -0.3541(2) 0.3259(3) 1.09363(13) 0.0612(5) Uani 1 1 d . . . . .
C9 C 0.2721(3) 0.7147(3) 0.52379(16) 0.0427(5) Uani 1 1 d . . . . .
C10 C 0.4502(3) 0.7256(4) 0.54550(17) 0.0488(6) Uani 1 1 d . . . . .
C11 C 0.5735(3) 0.7829(4) 0.4783(2) 0.0565(6) Uani 1 1 d . . . . .
H11 H 0.6924 0.7873 0.4962 0.068 Uiso 1 1 calc R U . . .
C12 C 0.5129(4) 0.8335(4) 0.38319(19) 0.0542(6) Uani 1 1 d . . . . .
C13 C 0.3395(4) 0.8278(4) 0.35369(18) 0.0599(7) Uani 1 1 d . . . . .
H13 H 0.3028 0.8617 0.2883 0.072 Uiso 1 1 calc R U . . .
C14 C 0.2228(3) 0.7698(4) 0.42515(17) 0.0527(6) Uani 1 1 d . . . . .
F1 F 0.5060(2) 0.6822(3) 0.64001(11) 0.0792(6) Uani 1 1 d . . . . .
F2 F 0.6292(3) 0.8946(3) 0.31440(14) 0.0808(6) Uani 1 1 d . . . . .
F3 F 0.0532(2) 0.7606(3) 0.39763(12) 0.0855(7) Uani 1 1 d . . . . .
O3 O 0.2206(3) 0.5173(3) 0.66873(13) 0.0626(5) Uani 1 1 d . . . . .
H1O H 0.135(5) 0.488(5) 0.712(3) 0.095(12) Uiso 1 1 d . . . . .
O4 O -0.0218(2) 0.7185(3) 0.59644(13) 0.0671(6) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.325(3) . ?
C1 N1 1.335(3) . ?
C1 H1 0.93 . ?
C2 C5 1.361(3) . ?
C2 N2 1.364(3) . ?
C2 N1 1.368(3) . ?
C3 O1 1.212(3) . ?
C3 N2 1.386(3) . ?
C3 N3 1.399(3) . ?
C4 O2 1.225(3) . ?
C4 N3 1.394(3) . ?
C4 C5 1.422(3) . ?
C5 N4 1.376(3) . ?
C6 N2 1.466(3) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C7 N3 1.473(3) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C8 O4 1.199(3) . ?
C8 O3 1.319(3) . ?
C8 C9 1.493(3) . ?
N4 H1N 0.90(3) . ?
C9 C10 1.383(4) . ?
C9 C14 1.393(3) . ?
C10 F1 1.349(3) . ?
C10 C11 1.363(4) . ?
C11 C12 1.368(4) . ?
C11 H11 0.93 . ?
C12 F2 1.350(3) . ?
C12 C13 1.369(4) . ?
C13 C14 1.368(3) . ?
C13 H13 0.93 . ?
C14 F3 1.341(3) . ?
O3 H1O 0.90(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 112.7(2) . . ?
N4 C1 H1 123.6 . . ?
N1 C1 H1 123.6 . . ?
C5 C2 N2 122.36(18) . . ?
C5 C2 N1 110.39(19) . . ?
N2 C2 N1 127.25(19) . . ?
O1 C3 N2 122.3(2) . . ?
O1 C3 N3 121.20(19) . . ?
N2 C3 N3 116.51(18) . . ?
O2 C4 N3 121.62(19) . . ?
O2 C4 C5 126.2(2) . . ?
N3 C4 C5 112.17(18) . . ?
C2 C5 N4 105.90(18) . . ?
C2 C5 C4 122.5(2) . . ?
N4 C5 C4 131.6(2) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 O3 124.0(2) . . ?
O4 C8 C9 124.0(2) . . ?
O3 C8 C9 112.0(2) . . ?
C1 N1 C2 104.16(18) . . ?
C2 N2 C3 119.54(17) . . ?
C2 N2 C6 122.20(18) . . ?
C3 N2 C6 118.24(18) . . ?
C4 N3 C3 126.88(18) . . ?
C4 N3 C7 117.88(18) . . ?
C3 N3 C7 115.21(18) . . ?
C1 N4 C5 106.81(19) . . ?
C1 N4 H1N 126.6(18) . . ?
C5 N4 H1N 126.4(18) . . ?
C10 C9 C14 114.7(2) . . ?
C10 C9 C8 123.6(2) . . ?
C14 C9 C8 121.6(2) . . ?
F1 C10 C11 117.0(2) . . ?
F1 C10 C9 118.3(2) . . ?
C11 C10 C9 124.7(2) . . ?
C10 C11 C12 116.4(2) . . ?
C10 C11 H11 121.8 . . ?
C12 C11 H11 121.8 . . ?
F2 C12 C11 118.5(2) . . ?
F2 C12 C13 117.9(2) . . ?
C11 C12 C13 123.7(2) . . ?
C14 C13 C12 116.8(2) . . ?
C14 C13 H13 121.6 . . ?
C12 C13 H13 121.6 . . ?
F3 C14 C13 117.7(2) . . ?
F3 C14 C9 118.5(2) . . ?
C13 C14 C9 123.8(2) . . ?
C8 O3 H1O 108(3) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

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

data_thp-246triFBA-II
_database_code_depnum_ccdc_archive 'CCDC 1451270'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2012-05-31T09:46:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
theophylline 2,4,6-trifluorobenzoic acid cocrystal 
;
_chemical_formula_sum            'C14 H11 F3 N4 O4'
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H3 F3 O2'
_chemical_formula_weight         356.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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


_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

_cell_length_a                   14.9998(3)
_cell_length_b                   6.90710(10)
_cell_length_c                   28.5122(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2954.01(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.48
_cell_measurement_reflns_used    11129

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_absorpt_correction_T_min  0.9858
_exptl_absorpt_correction_T_max  0.9928
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_number            19572
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         5.23
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       'omega and phi scans'
_reflns_number_total             2577
_reflns_number_gt                1286
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2577
_refine_ls_number_parameters     234
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.076
_refine_ls_wR_factor_gt          0.073
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.905
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
F3 F -0.00208(7) 0.7234(2) 0.55854(4) 0.0731(4) Uani 1 1 d . . .
O3 O 0.03002(8) 0.3532(2) 0.78864(4) 0.0647(5) Uani 1 1 d . . .
N3 N 0.17903(9) 0.3240(3) 0.80019(5) 0.0459(5) Uani 1 1 d . . .
C2 C 0.20530(11) 0.3897(3) 0.70813(7) 0.0402(5) Uani 1 1 d . . .
O4 O 0.32962(8) 0.2955(2) 0.81314(4) 0.0614(5) Uani 1 1 d . . .
N4 N 0.34980(11) 0.3824(3) 0.70802(6) 0.0477(5) Uani 1 1 d . . .
F2 F -0.02681(9) 0.8570(2) 0.39958(4) 0.0840(5) Uani 1 1 d . . .
N2 N 0.11927(9) 0.3839(3) 0.72495(6) 0.0456(5) Uani 1 1 d . . .
N1 N 0.22980(10) 0.4244(3) 0.66325(5) 0.0478(5) Uani 1 1 d . . .
O1 O 0.13609(9) 0.5365(3) 0.58639(5) 0.0729(5) Uani 1 1 d . . .
C5 C 0.27626(11) 0.3635(3) 0.73685(6) 0.0394(5) Uani 1 1 d . . .
F1 F 0.24251(9) 0.6298(3) 0.45768(4) 0.1006(6) Uani 1 1 d . . .
C3 C 0.10549(12) 0.3542(3) 0.77159(7) 0.0478(6) Uani 1 1 d . . .
O2 O 0.26275(10) 0.6099(3) 0.55074(5) 0.0819(6) Uani 1 1 d . . .
C9 C 0.12521(13) 0.6714(3) 0.51123(6) 0.0492(6) Uani 1 1 d U . .
C8 C 0.18287(16) 0.6044(3) 0.55077(7) 0.0557(6) Uani 1 1 d . . .
C1 C 0.31835(13) 0.4186(3) 0.66513(7) 0.0518(6) Uani 1 1 d . . .
H1 H 0.3547 0.4379 0.6391 0.062 Uiso 1 1 calc R . .
C14 C 0.03613(13) 0.7247(3) 0.51567(7) 0.0501(6) Uani 1 1 d U . .
C4 C 0.26907(12) 0.3247(3) 0.78541(7) 0.0454(6) Uani 1 1 d . . .
C6 C 0.04187(12) 0.3984(4) 0.69330(7) 0.0633(7) Uani 1 1 d . . .
H6A H 0.006 0.2838 0.6961 0.095 Uiso 1 1 calc R . .
H6B H 0.0622 0.4111 0.6615 0.095 Uiso 1 1 calc R . .
H6C H 0.0069 0.5096 0.7016 0.095 Uiso 1 1 calc R . .
C13 C -0.01638(13) 0.7845(3) 0.47939(7) 0.0546(6) Uani 1 1 d U . .
H13 H -0.0758 0.8178 0.4839 0.066 Uiso 1 1 calc R . .
C10 C 0.15744(14) 0.6827(4) 0.46606(7) 0.0634(7) Uani 1 1 d U . .
C7 C 0.16142(14) 0.2931(4) 0.85050(6) 0.0664(7) Uani 1 1 d . . .
H7A H 0.1101 0.367 0.8597 0.1 Uiso 1 1 calc R . .
H7B H 0.2122 0.3341 0.8684 0.1 Uiso 1 1 calc R . .
H7C H 0.1505 0.1581 0.8561 0.1 Uiso 1 1 calc R . .
C12 C 0.02217(16) 0.7931(3) 0.43649(7) 0.0594(6) Uani 1 1 d U . .
C11 C 0.10828(16) 0.7410(4) 0.42802(7) 0.0699(7) Uani 1 1 d . . .
H11 H 0.1325 0.7448 0.398 0.084 Uiso 1 1 calc R . .
H4N H 0.4087(16) 0.369(3) 0.7173(7) 0.084 Uiso 1 1 d . . .
H1O H 0.1738(14) 0.492(3) 0.6131(8) 0.084 Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C14 1.3501(19) . ?
O3 C3 1.232(2) . ?
N3 C3 1.387(2) . ?
N3 C4 1.415(2) . ?
N3 C7 1.474(2) . ?
C2 N1 1.353(2) . ?
C2 C5 1.355(2) . ?
C2 N2 1.377(2) . ?
O4 C4 1.221(2) . ?
N4 C1 1.334(2) . ?
N4 C5 1.382(2) . ?
N4 H4N 0.93(2) . ?
F2 C12 1.357(2) . ?
N2 C3 1.361(2) . ?
N2 C6 1.474(2) . ?
N1 C1 1.330(2) . ?
O1 C8 1.320(2) . ?
O1 H1O 1.00(2) . ?
C5 C4 1.414(2) . ?
F1 C10 1.349(2) . ?
O2 C8 1.199(2) . ?
C9 C10 1.378(2) . ?
C9 C14 1.392(3) . ?
C9 C8 1.494(3) . ?
C1 H1 0.93 . ?
C14 C13 1.364(3) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C13 C12 1.354(3) . ?
C13 H13 0.93 . ?
C10 C11 1.372(3) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C12 C11 1.362(3) . ?
C11 H11 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N3 C4 125.69(16) . . ?
C3 N3 C7 116.82(15) . . ?
C4 N3 C7 117.48(14) . . ?
N1 C2 C5 112.45(15) . . ?
N1 C2 N2 126.09(16) . . ?
C5 C2 N2 121.44(17) . . ?
C1 N4 C5 106.30(15) . . ?
C1 N4 H4N 128.1(13) . . ?
C5 N4 H4N 125.6(13) . . ?
C3 N2 C2 119.13(15) . . ?
C3 N2 C6 119.26(15) . . ?
C2 N2 C6 121.53(15) . . ?
C1 N1 C2 103.18(14) . . ?
C8 O1 H1O 113.3(12) . . ?
C2 C5 N4 104.76(16) . . ?
C2 C5 C4 123.86(17) . . ?
N4 C5 C4 131.38(16) . . ?
O3 C3 N2 121.71(17) . . ?
O3 C3 N3 119.86(18) . . ?
N2 C3 N3 118.43(17) . . ?
C10 C9 C14 114.00(18) . . ?
C10 C9 C8 121.31(19) . . ?
C14 C9 C8 124.68(18) . . ?
O2 C8 O1 122.90(19) . . ?
O2 C8 C9 124.6(2) . . ?
O1 C8 C9 112.49(19) . . ?
N1 C1 N4 113.30(16) . . ?
N1 C1 H1 123.3 . . ?
N4 C1 H1 123.3 . . ?
F3 C14 C13 116.32(18) . . ?
F3 C14 C9 119.22(17) . . ?
C13 C14 C9 124.44(18) . . ?
O4 C4 C5 127.49(17) . . ?
O4 C4 N3 121.10(17) . . ?
C5 C4 N3 111.41(15) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C13 C14 116.84(19) . . ?
C12 C13 H13 121.6 . . ?
C14 C13 H13 121.6 . . ?
F1 C10 C11 116.61(19) . . ?
F1 C10 C9 118.83(18) . . ?
C11 C10 C9 124.5(2) . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C12 F2 118.9(2) . . ?
C13 C12 C11 123.60(19) . . ?
F2 C12 C11 117.5(2) . . ?
C12 C11 C10 116.5(2) . . ?
C12 C11 H11 121.7 . . ?
C10 C11 H11 121.7 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


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

data_thp-345triFBA
_database_code_depnum_ccdc_archive 'CCDC 1451271'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2016-01-15T17:50:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C7 H8 N4 O2, C7 H3 F3 O2'
_chemical_formula_sum            'C14 H11 F3 N4 O4'
_chemical_formula_weight         356.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8138(5)
_cell_length_b                   12.5214(12)
_cell_length_c                   15.3432(8)
_cell_angle_alpha                90.873(6)
_cell_angle_beta                 91.670(7)
_cell_angle_gamma                96.870(9)
_cell_volume                     727.00(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    1797
_cell_measurement_theta_min      4.4950
_cell_measurement_theta_max      75.0070

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.050
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             364

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.62944
_exptl_absorpt_correction_T_max  1.00000


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.056
_diffrn_reflns_number            4269
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.556
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             2565
_reflns_number_gt                2056
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0948P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2565
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.066
#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2937(6) 0.41962(19) 0.29414(14) 0.0296(5) Uani 1 1 d . . . . .
H1 H -0.3928 0.4712 0.2618 0.036 Uiso 1 1 calc R U . . .
C2 C -0.0329(6) 0.34322(17) 0.40039(13) 0.0243(5) Uani 1 1 d . . . . .
C3 C 0.1339(6) 0.31472(17) 0.47860(14) 0.0254(5) Uani 1 1 d . . . . .
C4 C 0.1312(6) 0.13305(17) 0.40748(13) 0.0251(5) Uani 1 1 d . . . . .
C5 C -0.1182(6) 0.27171(18) 0.33201(13) 0.0249(5) Uani 1 1 d . . . . .
C6 C -0.1486(6) 0.09012(18) 0.26411(14) 0.0303(5) Uani 1 1 d . . . . .
H6A H -0.0709 0.022 0.2779 0.046 Uiso 0.5 1 calc R U P . .
H6B H -0.4014 0.0816 0.257 0.046 Uiso 0.5 1 calc R U P . .
H6C H -0.0446 0.1158 0.211 0.046 Uiso 0.5 1 calc R U P . .
H6D H -0.2737 0.1243 0.2193 0.046 Uiso 0.5 1 calc R U P . .
H6E H 0.0568 0.0647 0.2403 0.046 Uiso 0.5 1 calc R U P . .
H6F H -0.3 0.0305 0.2862 0.046 Uiso 0.5 1 calc R U P . .
C7 C 0.3703(6) 0.16845(19) 0.55673(15) 0.0310(5) Uani 1 1 d . . . . .
H7A H 0.5439 0.2236 0.581 0.046 Uiso 1 1 calc R U . . .
H7B H 0.4816 0.1059 0.5426 0.046 Uiso 1 1 calc R U . . .
H7C H 0.1914 0.1501 0.5985 0.046 Uiso 1 1 calc R U . . .
N1 N -0.2815(5) 0.31822(15) 0.26576(11) 0.0272(4) Uani 1 1 d . . . . .
N2 N -0.1485(5) 0.43824(15) 0.37363(11) 0.0278(4) Uani 1 1 d . . . . .
H1N H -0.13 0.498 0.4028 0.033 Uiso 1 1 calc R U . . .
N3 N 0.2078(5) 0.20789(15) 0.47735(11) 0.0258(4) Uani 1 1 d . . . . .
N4 N -0.0402(5) 0.16770(15) 0.33507(11) 0.0259(4) Uani 1 1 d . . . . .
O1 O 0.2125(5) 0.37241(13) 0.54378(10) 0.0348(4) Uani 1 1 d . . . . .
O2 O 0.2163(4) 0.04268(13) 0.41149(10) 0.0328(4) Uani 1 1 d . . . . .
C8 C 0.2822(6) 0.32330(18) 0.07089(14) 0.0279(5) Uani 1 1 d . . . . .
C9 C 0.0898(6) 0.28264(18) -0.01205(13) 0.0266(5) Uani 1 1 d . . . . .
C10 C 0.0355(6) 0.35493(19) -0.07675(15) 0.0310(5) Uani 1 1 d . . . . .
H10 H 0.1128 0.4278 -0.069 0.037 Uiso 1 1 calc R U . . .
C11 C -0.1360(7) 0.3161(2) -0.15301(15) 0.0333(5) Uani 1 1 d . . . . .
C12 C -0.2592(6) 0.2084(2) -0.16482(14) 0.0330(5) Uani 1 1 d . . . . .
C13 C -0.2062(6) 0.13816(19) -0.09877(15) 0.0321(5) Uani 1 1 d . . . . .
C14 C -0.0309(6) 0.17310(19) -0.02227(14) 0.0294(5) Uani 1 1 d . . . . .
H14 H 0.0067 0.1251 0.0217 0.035 Uiso 1 1 calc R U . . .
F1 F -0.1945(5) 0.38263(14) -0.21864(10) 0.0506(5) Uani 1 1 d . . . . .
F2 F -0.4286(5) 0.17241(14) -0.23893(9) 0.0486(4) Uani 1 1 d . . . . .
F3 F -0.3334(5) 0.03355(12) -0.11051(9) 0.0480(4) Uani 1 1 d . . . . .
O3 O 0.3526(5) 0.41841(14) 0.08901(11) 0.0407(5) Uani 1 1 d . . . . .
O4 O 0.3674(5) 0.24469(13) 0.12071(10) 0.0348(4) Uani 1 1 d . . . . .
H1O H 0.4709 0.2702 0.1652 0.052 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.330(3) . ?
C1 N1 1.343(3) . ?
C1 H1 0.93 . ?
C2 C5 1.375(3) . ?
C2 N2 1.381(3) . ?
C2 C3 1.412(3) . ?
C3 O1 1.233(3) . ?
C3 N3 1.400(3) . ?
C4 O2 1.216(3) . ?
C4 N4 1.375(3) . ?
C4 N3 1.414(3) . ?
C5 N1 1.352(3) . ?
C5 N4 1.371(3) . ?
C6 N4 1.465(3) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C6 H6D 0.96 . ?
C6 H6E 0.96 . ?
C6 H6F 0.96 . ?
C7 N3 1.469(3) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
N2 H1N 0.86 . ?
C8 O3 1.215(3) . ?
C8 O4 1.320(3) . ?
C8 C9 1.501(3) . ?
C9 C10 1.381(3) . ?
C9 C14 1.399(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.93 . ?
C11 F1 1.347(3) . ?
C11 C12 1.381(4) . ?
C12 F2 1.336(3) . ?
C12 C13 1.378(4) . ?
C13 F3 1.349(3) . ?
C13 C14 1.373(3) . ?
C14 H14 0.93 . ?
O4 H1O 0.82 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 112.7(2) . . ?
N2 C1 H1 123.7 . . ?
N1 C1 H1 123.7 . . ?
C5 C2 N2 105.14(18) . . ?
C5 C2 C3 122.8(2) . . ?
N2 C2 C3 132.10(19) . . ?
O1 C3 N3 120.1(2) . . ?
O1 C3 C2 127.2(2) . . ?
N3 C3 C2 112.68(18) . . ?
O2 C4 N4 121.96(19) . . ?
O2 C4 N3 121.2(2) . . ?
N4 C4 N3 116.87(19) . . ?
N1 C5 N4 127.16(19) . . ?
N1 C5 C2 111.1(2) . . ?
N4 C5 C2 121.7(2) . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C6 H6D 109.5 . . ?
H6A C6 H6D 141.1 . . ?
H6B C6 H6D 56.3 . . ?
H6C C6 H6D 56.3 . . ?
N4 C6 H6E 109.5 . . ?
H6A C6 H6E 56.3 . . ?
H6B C6 H6E 141.1 . . ?
H6C C6 H6E 56.3 . . ?
H6D C6 H6E 109.5 . . ?
N4 C6 H6F 109.5 . . ?
H6A C6 H6F 56.3 . . ?
H6B C6 H6F 56.3 . . ?
H6C C6 H6F 141.1 . . ?
H6D C6 H6F 109.5 . . ?
H6E C6 H6F 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 N1 C5 104.22(18) . . ?
C1 N2 C2 106.84(18) . . ?
C1 N2 H1N 126.6 . . ?
C2 N2 H1N 126.6 . . ?
C3 N3 C4 126.01(19) . . ?
C3 N3 C7 117.29(18) . . ?
C4 N3 C7 116.68(18) . . ?
C5 N4 C4 119.93(18) . . ?
C5 N4 C6 121.53(19) . . ?
C4 N4 C6 118.49(19) . . ?
O3 C8 O4 124.4(2) . . ?
O3 C8 C9 123.1(2) . . ?
O4 C8 C9 112.59(19) . . ?
C10 C9 C14 121.4(2) . . ?
C10 C9 C8 118.9(2) . . ?
C14 C9 C8 119.7(2) . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
F1 C11 C10 120.9(2) . . ?
F1 C11 C12 117.5(2) . . ?
C10 C11 C12 121.6(2) . . ?
F2 C12 C13 120.2(2) . . ?
F2 C12 C11 120.8(2) . . ?
C13 C12 C11 119.1(2) . . ?
F3 C13 C14 120.3(2) . . ?
F3 C13 C12 118.5(2) . . ?
C14 C13 C12 121.3(2) . . ?
C13 C14 C9 118.4(2) . . ?
C13 C14 H14 120.8 . . ?
C9 C14 H14 120.8 . . ?
C8 O4 H1O 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

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

data_thp-2345tetFBA
_database_code_depnum_ccdc_archive 'CCDC 1451272'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2016-01-15T18:19:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C7 H2 F4 O2, C7 H8 N4 O2'
_chemical_formula_sum            'C14 H10 F4 N4 O4'
_chemical_formula_weight         374.26

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.5149(2)
_cell_length_b                   27.5566(3)
_cell_length_c                   8.01140(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.5320(10)
_cell_angle_gamma                90
_cell_volume                     2942.45(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    7031
_cell_measurement_theta_min      3.7030
_cell_measurement_theta_max      74.6270

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.69
_exptl_crystal_F_000             1520

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.77875
_exptl_absorpt_correction_T_max  1.00000

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_number            10721
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.207
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_full        66.598
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_coverage         0
_reflns_number_total             5169
_reflns_number_gt                4642
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0756P)²+0.5742P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5169
_refine_ls_number_parameters     485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.57606(11) 0.47643(6) 0.18090(18) 0.0215(3) Uani 1 1 d . . . . .
H1 H 0.6155 0.4512 0.1511 0.026 Uiso 1 1 calc R U . . .
C2 C 0.51830(11) 0.54664(5) 0.21276(17) 0.0192(3) Uani 1 1 d . . . . .
C3 C 0.42770(12) 0.61441(6) 0.29206(18) 0.0221(3) Uani 1 1 d . . . . .
C4 C 0.37936(11) 0.53032(5) 0.36594(18) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.45963(11) 0.51485(5) 0.28392(17) 0.0193(3) Uani 1 1 d . . . . .
C6 C 0.56054(13) 0.62870(6) 0.1225(2) 0.0282(4) Uani 1 1 d . . . . .
H6A H 0.5389 0.6615 0.1354 0.042 Uiso 0.5 1 calc R U P . .
H6B H 0.6304 0.6258 0.1694 0.042 Uiso 0.5 1 calc R U P . .
H6C H 0.5506 0.6204 0.0045 0.042 Uiso 0.5 1 calc R U P . .
H6D H 0.6077 0.6103 0.0709 0.042 Uiso 0.5 1 calc R U P . .
H6E H 0.5162 0.646 0.0368 0.042 Uiso 0.5 1 calc R U P . .
H6F H 0.596 0.6514 0.2017 0.042 Uiso 0.5 1 calc R U P . .
C7 C 0.29270(13) 0.60099(6) 0.4553(2) 0.0307(4) Uani 1 1 d . . . . .
H7A H 0.2928 0.6357 0.4462 0.046 Uiso 0.5 1 calc R U P . .
H7B H 0.228 0.5887 0.4059 0.046 Uiso 0.5 1 calc R U P . .
H7C H 0.3071 0.5918 0.5724 0.046 Uiso 0.5 1 calc R U P . .
H7D H 0.2591 0.5751 0.5035 0.046 Uiso 0.5 1 calc R U P . .
H7E H 0.324 0.6221 0.5437 0.046 Uiso 0.5 1 calc R U P . .
H7F H 0.2448 0.619 0.3773 0.046 Uiso 0.5 1 calc R U P . .
N1 N 0.59145(9) 0.52277(5) 0.14751(15) 0.0220(3) Uani 1 1 d . . . . .
N2 N 0.50218(10) 0.59577(5) 0.21129(16) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.36927(10) 0.58071(5) 0.36554(16) 0.0217(3) Uani 1 1 d . . . . .
N4 N 0.49833(10) 0.46963(5) 0.26155(16) 0.0202(3) Uani 1 1 d . . . . .
H4N H 0.4783(15) 0.4421(8) 0.291(2) 0.032(5) Uiso 1 1 d . . . . .
O1 O 0.41255(9) 0.65775(4) 0.29894(15) 0.0295(3) Uani 1 1 d . . . . .
O2 O 0.32407(8) 0.50426(4) 0.43436(13) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.96221(12) 0.35273(6) 0.79130(19) 0.0247(3) Uani 1 1 d . . . . .
C9 C 0.88191(12) 0.33052(6) 0.87518(19) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.86503(12) 0.28108(6) 0.8843(2) 0.0247(3) Uani 1 1 d . . . . .
C11 C 0.78882(13) 0.26304(6) 0.9630(2) 0.0282(4) Uani 1 1 d . . . . .
C12 C 0.72887(13) 0.29462(7) 1.0355(2) 0.0300(4) Uani 1 1 d . . . . .
C13 C 0.74634(13) 0.34366(7) 1.0280(2) 0.0292(4) Uani 1 1 d . . . . .
C14 C 0.82073(12) 0.36208(6) 0.9496(2) 0.0262(4) Uani 1 1 d . . . . .
H14 H 0.8306 0.3954 0.9457 0.031 Uiso 1 1 calc R U . . .
F1 F 0.68522(8) 0.37356(4) 1.09792(14) 0.0428(3) Uani 1 1 d . . . . .
F2 F 0.65478(8) 0.27720(4) 1.10988(15) 0.0450(3) Uani 1 1 d . . . . .
F3 F 0.77346(9) 0.21539(4) 0.96982(15) 0.0432(3) Uani 1 1 d . . . . .
F4 F 0.91942(8) 0.24788(3) 0.81836(13) 0.0341(3) Uani 1 1 d . . . . .
O3 O 1.01777(10) 0.32062(5) 0.72900(18) 0.0390(3) Uani 1 1 d . . . . .
H3O H 1.067(2) 0.3371(10) 0.689(3) 0.063(8) Uiso 1 1 d . . . . .
O4 O 0.97366(10) 0.39611(4) 0.78445(17) 0.0361(3) Uani 1 1 d . . . . .
C15 C 0.80743(12) 0.59547(6) 0.41004(19) 0.0245(3) Uani 1 1 d . . . . .
H15 H 0.8429 0.5707 0.3674 0.029 Uiso 1 1 calc R U . . .
C16 C 0.76140(11) 0.66511(6) 0.47873(18) 0.0207(3) Uani 1 1 d . . . . .
C17 C 0.67576(12) 0.73176(6) 0.5764(2) 0.0236(3) Uani 1 1 d . . . . .
C18 C 0.61268(11) 0.64737(6) 0.60526(18) 0.0210(3) Uani 1 1 d . . . . .
C19 C 0.69589(11) 0.63254(5) 0.52935(18) 0.0204(3) Uani 1 1 d . . . . .
C20 C 0.82914(13) 0.74774(6) 0.4587(2) 0.0299(4) Uani 1 1 d . . . . .
H20A H 0.8121 0.7803 0.4858 0.045 Uiso 0.5 1 calc R U P . .
H20B H 0.8941 0.7396 0.5206 0.045 Uiso 0.5 1 calc R U P . .
H20C H 0.8304 0.7453 0.3395 0.045 Uiso 0.5 1 calc R U P . .
H20D H 0.8789 0.7299 0.4115 0.045 Uiso 0.5 1 calc R U P . .
H20E H 0.7969 0.7705 0.3766 0.045 Uiso 0.5 1 calc R U P . .
H20F H 0.8607 0.7648 0.5577 0.045 Uiso 0.5 1 calc R U P . .
C21 C 0.52061(13) 0.71658(6) 0.6902(2) 0.0301(4) Uani 1 1 d . . . . .
H21A H 0.5243 0.7514 0.695 0.045 Uiso 0.5 1 calc R U P . .
H21B H 0.4595 0.707 0.6191 0.045 Uiso 0.5 1 calc R U P . .
H21C H 0.5217 0.7039 0.8022 0.045 Uiso 0.5 1 calc R U P . .
H21D H 0.4794 0.6901 0.7159 0.045 Uiso 0.5 1 calc R U P . .
H21E H 0.5442 0.7345 0.7917 0.045 Uiso 0.5 1 calc R U P . .
H21F H 0.482 0.7376 0.6086 0.045 Uiso 0.5 1 calc R U P . .
N5 N 0.83164(10) 0.64220(5) 0.40423(16) 0.0237(3) Uani 1 1 d . . . . .
N6 N 0.75398(10) 0.71396(5) 0.50485(17) 0.0231(3) Uani 1 1 d . . . . .
N7 N 0.60686(10) 0.69745(5) 0.62052(16) 0.0225(3) Uani 1 1 d . . . . .
N8 N 0.72702(10) 0.58776(5) 0.48332(16) 0.0227(3) Uani 1 1 d . . . . .
H8N H 0.7043(15) 0.5601(8) 0.506(2) 0.028(5) Uiso 1 1 d . . . . .
O5 O 0.66551(9) 0.77471(4) 0.60141(17) 0.0337(3) Uani 1 1 d . . . . .
O6 O 0.54929(8) 0.62088(4) 0.65174(15) 0.0268(3) Uani 1 1 d . . . . .
C22 C 0.79547(12) 0.52496(6) 0.94045(19) 0.0236(3) Uani 1 1 d . . . . .
C23 C 0.87609(11) 0.54808(6) 0.85988(18) 0.0224(3) Uani 1 1 d . . . . .
C24 C 0.88901(11) 0.59792(6) 0.84894(19) 0.0226(3) Uani 1 1 d . . . . .
C25 C 0.96474(12) 0.61708(6) 0.7725(2) 0.0259(4) Uani 1 1 d . . . . .
C26 C 1.02970(12) 0.58653(7) 0.7064(2) 0.0293(4) Uani 1 1 d . . . . .
C27 C 1.01706(13) 0.53714(7) 0.7176(2) 0.0302(4) Uani 1 1 d . . . . .
C28 C 0.94215(12) 0.51759(6) 0.7921(2) 0.0268(4) Uani 1 1 d . . . . .
H28 H 0.9351 0.4841 0.7977 0.032 Uiso 1 1 calc R U . . .
F5 F 0.83123(8) 0.63018(3) 0.91228(13) 0.0327(2) Uani 1 1 d . . . . .
F6 F 0.97540(8) 0.66517(4) 0.76272(13) 0.0372(3) Uani 1 1 d . . . . .
F7 F 1.10317(8) 0.60553(5) 0.63413(14) 0.0447(3) Uani 1 1 d . . . . .
F8 F 1.08161(8) 0.50834(4) 0.65196(15) 0.0443(3) Uani 1 1 d . . . . .
O7 O 0.72901(10) 0.55621(5) 0.97660(19) 0.0397(3) Uani 1 1 d . . . . .
H7O H 0.6842(19) 0.5418(9) 1.035(3) 0.054(7) Uiso 1 1 d . . . . .
O8 O 0.79246(10) 0.48201(4) 0.96708(16) 0.0360(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.328(2) . ?
C1 N4 1.334(2) . ?
C1 H1 0.93 . ?
C2 N1 1.362(2) . ?
C2 C5 1.368(2) . ?
C2 N2 1.371(2) . ?
C3 O1 1.2144(19) . ?
C3 N2 1.382(2) . ?
C3 N3 1.409(2) . ?
C4 O2 1.2289(19) . ?
C4 N3 1.395(2) . ?
C4 C5 1.423(2) . ?
C5 N4 1.375(2) . ?
C6 N2 1.462(2) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C6 H6D 0.96 . ?
C6 H6E 0.96 . ?
C6 H6F 0.96 . ?
C7 N3 1.465(2) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C7 H7D 0.96 . ?
C7 H7E 0.96 . ?
C7 H7F 0.96 . ?
N4 H4N 0.85(2) . ?
C8 O4 1.208(2) . ?
C8 O3 1.312(2) . ?
C8 C9 1.499(2) . ?
C9 C10 1.385(2) . ?
C9 C14 1.399(2) . ?
C10 F4 1.3361(19) . ?
C10 C11 1.386(2) . ?
C11 F3 1.332(2) . ?
C11 C12 1.381(2) . ?
C12 F2 1.336(2) . ?
C12 C13 1.375(3) . ?
C13 F1 1.3523(19) . ?
C13 C14 1.368(2) . ?
C14 H14 0.93 . ?
O3 H3O 0.90(3) . ?
C15 N5 1.331(2) . ?
C15 N8 1.335(2) . ?
C15 H15 0.93 . ?
C16 N5 1.358(2) . ?
C16 N6 1.368(2) . ?
C16 C19 1.369(2) . ?
C17 O5 1.212(2) . ?
C17 N6 1.374(2) . ?
C17 N7 1.412(2) . ?
C18 O6 1.2293(19) . ?
C18 N7 1.389(2) . ?
C18 C19 1.424(2) . ?
C19 N8 1.374(2) . ?
C20 N6 1.470(2) . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
C20 H20D 0.96 . ?
C20 H20E 0.96 . ?
C20 H20F 0.96 . ?
C21 N7 1.471(2) . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C21 H21D 0.96 . ?
C21 H21E 0.96 . ?
C21 H21F 0.96 . ?
N8 H8N 0.85(2) . ?
C22 O8 1.205(2) . ?
C22 O7 1.311(2) . ?
C22 C23 1.497(2) . ?
C23 C24 1.389(2) . ?
C23 C28 1.399(2) . ?
C24 F5 1.3376(18) . ?
C24 C25 1.382(2) . ?
C25 F6 1.3366(19) . ?
C25 C26 1.383(2) . ?
C26 F7 1.3364(19) . ?
C26 C27 1.377(3) . ?
C27 F8 1.3488(19) . ?
C27 C28 1.368(2) . ?
C28 H28 0.93 . ?
O7 H7O 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 113.24(14) . . ?
N1 C1 H1 123.4 . . ?
N4 C1 H1 123.4 . . ?
N1 C2 C5 111.01(13) . . ?
N1 C2 N2 126.74(14) . . ?
C5 C2 N2 122.26(14) . . ?
O1 C3 N2 121.86(15) . . ?
O1 C3 N3 121.23(15) . . ?
N2 C3 N3 116.90(13) . . ?
O2 C4 N3 121.07(14) . . ?
O2 C4 C5 126.67(14) . . ?
N3 C4 C5 112.24(14) . . ?
C2 C5 N4 105.48(13) . . ?
C2 C5 C4 122.64(14) . . ?
N4 C5 C4 131.84(14) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C6 H6D 109.5 . . ?
H6A C6 H6D 141.1 . . ?
H6B C6 H6D 56.3 . . ?
H6C C6 H6D 56.3 . . ?
N2 C6 H6E 109.5 . . ?
H6A C6 H6E 56.3 . . ?
H6B C6 H6E 141.1 . . ?
H6C C6 H6E 56.3 . . ?
H6D C6 H6E 109.5 . . ?
N2 C6 H6F 109.5 . . ?
H6A C6 H6F 56.3 . . ?
H6B C6 H6F 56.3 . . ?
H6C C6 H6F 141.1 . . ?
H6D C6 H6F 109.5 . . ?
H6E C6 H6F 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C7 H7D 109.5 . . ?
H7A C7 H7D 141.1 . . ?
H7B C7 H7D 56.3 . . ?
H7C C7 H7D 56.3 . . ?
N3 C7 H7E 109.5 . . ?
H7A C7 H7E 56.3 . . ?
H7B C7 H7E 141.1 . . ?
H7C C7 H7E 56.3 . . ?
H7D C7 H7E 109.5 . . ?
N3 C7 H7F 109.5 . . ?
H7A C7 H7F 56.3 . . ?
H7B C7 H7F 56.3 . . ?
H7C C7 H7F 141.1 . . ?
H7D C7 H7F 109.5 . . ?
H7E C7 H7F 109.5 . . ?
C1 N1 C2 103.84(13) . . ?
C2 N2 C3 119.33(13) . . ?
C2 N2 C6 121.28(13) . . ?
C3 N2 C6 119.37(13) . . ?
C4 N3 C3 126.53(14) . . ?
C4 N3 C7 117.08(13) . . ?
C3 N3 C7 116.35(13) . . ?
C1 N4 C5 106.43(13) . . ?
C1 N4 H4N 124.9(14) . . ?
C5 N4 H4N 128.7(14) . . ?
O4 C8 O3 124.39(16) . . ?
O4 C8 C9 122.17(15) . . ?
O3 C8 C9 113.44(14) . . ?
C10 C9 C14 118.34(15) . . ?
C10 C9 C8 124.27(15) . . ?
C14 C9 C8 117.39(15) . . ?
F4 C10 C9 123.12(15) . . ?
F4 C10 C11 115.67(15) . . ?
C9 C10 C11 121.20(15) . . ?
F3 C11 C12 119.86(15) . . ?
F3 C11 C10 120.32(16) . . ?
C12 C11 C10 119.81(16) . . ?
F2 C12 C13 121.28(16) . . ?
F2 C12 C11 119.75(17) . . ?
C13 C12 C11 118.96(16) . . ?
F1 C13 C14 120.65(16) . . ?
F1 C13 C12 117.37(16) . . ?
C14 C13 C12 121.95(16) . . ?
C13 C14 C9 119.72(16) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C8 O3 H3O 107.2(17) . . ?
N5 C15 N8 113.08(14) . . ?
N5 C15 H15 123.5 . . ?
N8 C15 H15 123.5 . . ?
N5 C16 N6 126.79(14) . . ?
N5 C16 C19 111.03(14) . . ?
N6 C16 C19 122.17(14) . . ?
O5 C17 N6 122.31(15) . . ?
O5 C17 N7 120.94(15) . . ?
N6 C17 N7 116.75(14) . . ?
O6 C18 N7 120.72(14) . . ?
O6 C18 C19 126.74(14) . . ?
N7 C18 C19 112.52(14) . . ?
C16 C19 N8 105.53(13) . . ?
C16 C19 C18 122.25(14) . . ?
N8 C19 C18 132.15(14) . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C20 H20D 109.5 . . ?
H20A C20 H20D 141.1 . . ?
H20B C20 H20D 56.3 . . ?
H20C C20 H20D 56.3 . . ?
N6 C20 H20E 109.5 . . ?
H20A C20 H20E 56.3 . . ?
H20B C20 H20E 141.1 . . ?
H20C C20 H20E 56.3 . . ?
H20D C20 H20E 109.5 . . ?
N6 C20 H20F 109.5 . . ?
H20A C20 H20F 56.3 . . ?
H20B C20 H20F 56.3 . . ?
H20C C20 H20F 141.1 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
N7 C21 H21A 109.5 . . ?
N7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N7 C21 H21D 109.5 . . ?
H21A C21 H21D 141.1 . . ?
H21B C21 H21D 56.3 . . ?
H21C C21 H21D 56.3 . . ?
N7 C21 H21E 109.5 . . ?
H21A C21 H21E 56.3 . . ?
H21B C21 H21E 141.1 . . ?
H21C C21 H21E 56.3 . . ?
H21D C21 H21E 109.5 . . ?
N7 C21 H21F 109.5 . . ?
H21A C21 H21F 56.3 . . ?
H21B C21 H21F 56.3 . . ?
H21C C21 H21F 141.1 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C15 N5 C16 103.93(13) . . ?
C16 N6 C17 119.73(13) . . ?
C16 N6 C20 120.89(13) . . ?
C17 N6 C20 119.38(13) . . ?
C18 N7 C17 126.43(13) . . ?
C18 N7 C21 116.71(13) . . ?
C17 N7 C21 116.85(13) . . ?
C15 N8 C19 106.43(13) . . ?
C15 N8 H8N 125.7(13) . . ?
C19 N8 H8N 127.6(13) . . ?
O8 C22 O7 124.19(15) . . ?
O8 C22 C23 122.86(15) . . ?
O7 C22 C23 112.94(14) . . ?
C24 C23 C28 118.31(15) . . ?
C24 C23 C22 123.78(14) . . ?
C28 C23 C22 117.92(14) . . ?
F5 C24 C25 115.86(14) . . ?
F5 C24 C23 123.08(14) . . ?
C25 C24 C23 121.06(15) . . ?
F6 C25 C24 119.98(15) . . ?
F6 C25 C26 119.97(15) . . ?
C24 C25 C26 120.05(15) . . ?
F7 C26 C27 121.65(16) . . ?
F7 C26 C25 119.45(16) . . ?
C27 C26 C25 118.90(15) . . ?
F8 C27 C28 120.78(16) . . ?
F8 C27 C26 117.45(16) . . ?
C28 C27 C26 121.77(16) . . ?
C27 C28 C23 119.91(16) . . ?
C27 C28 H28 120 . . ?
C23 C28 H28 120 . . ?
C22 O7 H7O 111.4(16) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

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

data_thp-23456pFBA
_database_code_depnum_ccdc_archive 'CCDC 1451273'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_systematic        
; ?
;
_chemical_name_common            'theophylline:pentafluorobenzoic acid'
_chemical_formula_moiety         '(C7 H8 N4 O2), (C7 H1 F5 O2)'
_chemical_formula_structural     '(C7 H8 N4 O2), (C7 H1 F5 O2)'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C14 H9 F5 N4 O4'
_chemical_formula_weight         392.25
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and 
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_length_neutron # include if applicable
? ? ? ? ? ?

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-p 1'

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


_cell_length_a                   7.93042(96)
_cell_length_b                   9.52612(99)
_cell_length_c                   10.9594(10)
_cell_angle_alpha                92.8738(48)
_cell_angle_beta                 105.7547(66)
_cell_angle_gamma                105.7529(70)
_cell_volume                     760.02(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_theta_min      2
_cell_measurement_theta_max      60
_cell_measurement_reflns_used    20
_exptl_crystal_density_diffrn    1.7140(4)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396

_cell_special_details            
; ?
;

# The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              14 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              10 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              0.5 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 'packed powder pellet'
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet

_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions



_pd_prep_temperature             293


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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_measurement_device_type  "Panalytical X'pert Powder"
_diffrn_detector                 ?
_diffrn_detector_type            X'Celerator # make or model of detector

_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  none

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        1726
_pd_meas_2theta_range_min        3.00
_pd_meas_2theta_range_max        60.00
_pd_meas_2theta_range_inc        0.033



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

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_pref_orient_corr     
; 'March-Dollase, axis (1 -1 0)'
;

_pd_proc_ls_prof_R_factor        0.063
_pd_proc_ls_prof_wR_factor       0.082
_pd_proc_ls_prof_wR_expected     0.012
_refine_ls_R_I_factor            0.026


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     47
_refine_ls_number_restraints     0
_refine_ls_number_constraints    96

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   6.944


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        60
_pd_proc_2theta_range_inc        0.033
_pd_proc_wavelength              1.5418

# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting 
# of one data block containing a single powder profile. The value of 
# _pd_block_diffractogram_id is used to associate each refinement with 
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template 
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given 
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?




# The following items are used to identify the programs used.

_computing_data_collection       "X'Pert Data Collector (Panalytical )"
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'DASH 3.2 (David et al 2008) '
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
O1 O 0.1088(10) -0.87121(81) -0.32773(88) 1 5.22(17)
O2 O -0.1648(14) -0.60641(62) -0.12107(61) 1 5.22(17)
N1 N -0.46117(92) -0.82630(69) -0.54942(61) 1 5.22(17)
N2 N -0.2356(13) -0.91918(61) -0.56327(53) 1 5.22(17)
H2 H -0.1748(15) -0.96910(73) -0.59749(67) 1 5.22(17)
N3 N -0.02926(87) -0.73756(51) -0.22740(49) 1 5.22(17)
N4 N -0.32439(85) -0.70953(54) -0.32820(63) 1 5.22(17)
C1 C -0.4007(13) -0.90476(69) -0.62427(48) 1 5.22(17)
H1 H -0.4656(15) -0.94466(83) -0.70947(50) 1 5.22(17)
C2 C -0.18360(93) -0.84614(47) -0.44104(48) 1 5.22(17)
C3 C -0.02468(87) -0.82388(56) -0.33350(60) 1 5.22(17)
C4 C 0.1313(10) -0.70508(75) -0.11306(61) 1 5.22(17)
H3 H 0.1281(12) -0.78850(83) -0.06904(67) 1 5.22(17)
H4 H 0.23859(94) -0.68108(89) -0.13949(78) 1 5.22(17)
H5 H 0.1290(12) -0.62570(75) -0.05882(54) 1 5.22(17)
C5 C -0.1729(10) -0.67962(48) -0.21892(51) 1 5.22(17)
C6 C -0.32632(79) -0.78958(50) -0.43562(51) 1 5.22(17)
C7 C -0.4744(10) -0.64747(83) -0.32910(97) 1 5.22(17)
H6 H -0.58607(97) -0.72359(98) -0.3427(11) 1 5.22(17)
H7 H -0.4443(13) -0.59016(87) -0.2491(10) 1 5.22(17)
H8 H -0.4882(11) -0.58752(85) -0.3957(10) 1 5.22(17)
F1 F 0.1517(10) -0.05953(53) -0.03267(51) 1 5.22(17)
F2 F 0.45477(84) -0.14361(64) 0.04988(45) 1 5.22(17)
F3 F 0.51149(76) -0.35783(69) -0.09508(72) 1 5.22(17)
F4 F 0.2496(11) -0.49713(59) -0.31841(64) 1 5.22(17)
F5 F -0.05632(93) -0.42291(60) -0.39863(34) 1 5.22(17)
O3 O -0.22088(82) -0.21842(77) -0.38384(58) 1 5.22(17)
H9 H -0.32953(85) -0.20218(91) -0.40100(73) 1 5.22(17)
O4 O -0.20944(92) -0.15112(77) -0.18045(72) 1 5.22(17)
C8 C -0.14448(78) -0.19712(65) -0.25760(56) 1 5.22(17)
C9 C 0.03278(71) -0.23706(46) -0.21825(36) 1 5.22(17)
C10 C 0.17110(77) -0.16585(44) -0.10654(37) 1 5.22(17)
C11 C 0.33116(71) -0.20762(48) -0.06233(39) 1 5.22(17)
C12 C 0.36018(71) -0.31896(51) -0.13494(50) 1 5.22(17)
C13 C 0.22864(82) -0.38747(47) -0.24948(46) 1 5.22(17)
C14 C 0.06709(77) -0.34755(46) -0.28986(32) 1 5.22(17)




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


# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.25(1)
O2 C5 1.226(9)
N1 C1 1.34(1)
N1 C6 1.360(8)
N2 H2 0.90(1)
N2 C1 1.35(1)
N2 C2 1.378(7)
N3 C3 1.405(9)
N3 C4 1.472(8)
N3 C5 1.42(1)
N4 C5 1.399(8)
N4 C6 1.364(9)
N4 C7 1.46(1)
C1 H1 0.937(7)
C2 C3 1.430(8)
C2 C6 1.39(1)
C4 H3 0.95(1)
C4 H4 0.95(1)
C4 H5 0.95(1)
C7 H6 0.95(1)
C7 H7 0.94(1)
C7 H8 0.95(1)
F1 C10 1.332(8)
F2 C11 1.338(6)
F3 C12 1.319(9)
F4 C13 1.332(9)
F5 C14 1.339(5)
O3 H9 0.89(1)
O3 C8 1.331(8)
O4 C8 1.22(1)
C8 C9 1.511(9)
C9 C10 1.395(5)
C9 C14 1.409(7)
C10 C11 1.401(8)
C11 C12 1.399(8)
C12 C13 1.388(6)
C13 C14 1.398(9)


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C6 104.7(6)
H2 N2 C1 125.0(9)
H2 N2 C2 128.0(9)
C1 N2 C2 107.0(6)
C3 N3 C4 116.6(5)
C3 N3 C5 126.7(5)
C4 N3 C5 116.8(5)
C5 N4 C6 119.6(6)
C5 N4 C7 119.8(6)
C6 N4 C7 120.4(6)
N1 C1 N2 112.4(7)
N1 C1 H1 124.0(9)
N2 C1 H1 123.6(9)
N2 C2 C3 132.8(6)
N2 C2 C6 105.3(5)
C3 C2 C6 121.9(5)
O1 C3 N3 120.4(7)
O1 C3 C2 127.0(7)
N3 C3 C2 112.6(5)
N3 C4 H3 110.4(8)
N3 C4 H4 108.5(8)
N3 C4 H5 108.4(8)
H3 C4 H4 109(1)
H3 C4 H5 110(1)
H4 C4 H5 111(1)
O2 C5 N3 121.8(6)
O2 C5 N4 121.6(6)
N3 C5 N4 116.6(5)
N1 C6 N4 126.9(6)
N1 C6 C2 110.6(5)
N4 C6 C2 122.6(5)
N4 C7 H6 111(1)
N4 C7 H7 108(1)
N4 C7 H8 109.4(9)
H6 C7 H7 110(1)
H6 C7 H8 109(1)
H7 C7 H8 110(1)
H9 O3 C8 108.9(8)
O3 C8 O4 124.4(7)
O3 C8 C9 112.8(5)
O4 C8 C9 122.9(6)
C8 C9 C10 120.8(4)
C8 C9 C14 122.7(4)
C10 C9 C14 116.5(4)
F1 C10 C9 121.0(5)
F1 C10 C11 116.7(5)
C9 C10 C11 122.2(4)
F2 C11 C10 120.4(5)
F2 C11 C12 119.8(5)
C10 C11 C12 119.7(4)
F3 C12 C11 120.3(5)
F3 C12 C13 120.4(5)
C11 C12 C13 119.3(5)
F4 C13 C12 120.7(5)
F4 C13 C14 119.2(5)
C12 C13 C14 120.0(5)
F5 C14 C9 121.5(5)
F5 C14 C13 116.5(5)
C9 C14 C13 122.0(4)



















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

data_thp-23456pFBA-II
_database_code_depnum_ccdc_archive 'CCDC 1451274'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2016-04-18T20:23:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C7 H F5 O2, C7 H8 N4 O2'
_chemical_formula_sum            'C14 H9 F5 N4 O4'
_chemical_formula_weight         392.24

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9430(3)
_cell_length_b                   11.5102(4)
_cell_length_c                   15.6500(5)
_cell_angle_alpha                104.915(3)
_cell_angle_beta                 99.944(3)
_cell_angle_gamma                93.655(3)
_cell_volume                     1523.34(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    10863
_cell_measurement_theta_min      3.9940
_cell_measurement_theta_max      73.5540




#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.097
_exptl_crystal_density_diffrn    1.71
_exptl_crystal_F_000             792

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.62599
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed X-ray tube'
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4061
_diffrn_orient_matrix_ub_11      0.0304936
_diffrn_orient_matrix_ub_12      0.1313394
_diffrn_orient_matrix_ub_13      0.0602288
_diffrn_orient_matrix_ub_21      0.0844707
_diffrn_orient_matrix_ub_22      -0.0437851
_diffrn_orient_matrix_ub_23      0.0783087
_diffrn_orient_matrix_ub_31      0.151401
_diffrn_orient_matrix_ub_32      0.016402
_diffrn_orient_matrix_ub_33      -0.0321368
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_number            9838
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_full        66.587
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_oxdiff_twin_integration_method simultaneous
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.5934 18779 13395
2 0.4066 18854 13395
loop_
_twin_individual_id
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000
2 -0.9996 0.0000 0.0002 0.0003 -0.9999 0.0003 0.6651 0.7332 1.0000
_reflns_Friedel_coverage         0
_reflns_number_total             9838
_reflns_number_gt                8733
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9838
_refine_ls_number_parameters     499
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.1016
_refine_ls_wR_factor_ref         0.2778
_refine_ls_wR_factor_gt          0.2655
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.102

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.049 0.032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.073 0.053 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.2430(5) 0.5729(4) 0.6882(3) 0.0341(9) Uani 1 1 d . . . . .
H4A H 0.2716 0.4964 0.6951 0.051 Uiso 1 1 calc R U . . .
H4B H 0.153 0.59 0.7127 0.051 Uiso 1 1 calc R U . . .
H4C H 0.3249 0.6354 0.7197 0.051 Uiso 1 1 calc R U . . .
F2 F 0.5012(3) 0.2383(2) 0.89243(17) 0.0453(7) Uani 1 1 d . . . . .
F5 F 0.1380(3) 0.5686(2) 1.02894(15) 0.0370(6) Uani 1 1 d . . . . .
F1 F 0.5224(3) 0.3164(2) 1.07293(16) 0.0388(6) Uani 1 1 d . . . . .
F3 F 0.2899(3) 0.3171(2) 0.78061(15) 0.0402(6) Uani 1 1 d . . . . .
O3 O 0.1956(3) 0.4677(3) 1.17414(17) 0.0329(6) Uani 1 1 d . . . . .
H3O H 0.1989 0.499 1.2279 0.049 Uiso 1 1 calc R U . . .
F4 F 0.1174(3) 0.4886(3) 0.84919(16) 0.0432(6) Uani 1 1 d . . . . .
O4 O 0.4481(3) 0.5219(3) 1.20928(17) 0.0331(6) Uani 1 1 d . . . . .
C10 C 0.4205(4) 0.3592(3) 1.0191(3) 0.0269(8) Uani 1 1 d . . . . .
C14 C 0.2248(4) 0.4842(3) 0.9970(3) 0.0271(8) Uani 1 1 d . . . . .
C13 C 0.2145(5) 0.4451(4) 0.9048(3) 0.0298(8) Uani 1 1 d . . . . .
C12 C 0.3045(5) 0.3592(4) 0.8694(3) 0.0307(8) Uani 1 1 d . . . . .
C9 C 0.3260(4) 0.4413(3) 1.0558(2) 0.0235(7) Uani 1 1 d . . . . .
C11 C 0.4106(5) 0.3183(3) 0.9267(3) 0.0312(8) Uani 1 1 d . . . . .
C8 C 0.3317(4) 0.4820(3) 1.1559(2) 0.0235(7) Uani 1 1 d . . . . .
O5 O 0.1458(3) 0.1012(2) 0.56452(18) 0.0319(6) Uani 1 1 d . . . . .
N8 N 0.4709(4) -0.2314(3) 0.4028(2) 0.0233(6) Uani 1 1 d D . . . .
N6 N 0.2359(3) 0.0009(3) 0.4422(2) 0.0229(6) Uani 1 1 d . . . . .
O6 O 0.4575(3) -0.1879(2) 0.60369(18) 0.0315(6) Uani 1 1 d . . . . .
C17 C 0.3944(4) -0.1338(3) 0.5530(2) 0.0226(7) Uani 1 1 d . . . . .
N7 N 0.3028(4) -0.0422(3) 0.58297(19) 0.0223(6) Uani 1 1 d . . . . .
N5 N 0.3416(4) -0.1249(3) 0.3206(2) 0.0239(6) Uani 1 1 d . . . . .
C21 C 0.3209(4) -0.0880(3) 0.4076(2) 0.0199(7) Uani 1 1 d . . . . .
C16 C 0.3991(4) -0.1518(3) 0.4600(2) 0.0211(7) Uani 1 1 d . . . . .
C19 C 0.2227(4) 0.0241(3) 0.5311(2) 0.0233(7) Uani 1 1 d . . . . .
C18 C 0.2908(5) -0.0159(3) 0.6789(2) 0.0282(8) Uani 1 1 d . . . . .
H18A H 0.2485 0.0592 0.6964 0.042 Uiso 1 1 calc R U . . .
H18B H 0.3906 -0.01 0.7154 0.042 Uiso 1 1 calc R U . . .
H18C H 0.2257 -0.0799 0.6874 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4325(4) -0.2121(3) 0.3216(2) 0.0255(8) Uani 1 1 d . . . . .
H15 H 0.4659 -0.2553 0.2708 0.031 Uiso 1 1 calc R U . . .
C20 C 0.1583(5) 0.0702(4) 0.3847(3) 0.0351(9) Uani 1 1 d . . . . .
H20A H 0.2222 0.0851 0.3444 0.053 Uiso 1 1 calc R U . . .
H20B H 0.1384 0.1459 0.4217 0.053 Uiso 1 1 calc R U . . .
H20C H 0.0635 0.0248 0.3504 0.053 Uiso 1 1 calc R U . . .
H8N H 0.529(6) -0.287(4) 0.418(4) 0.053 Uiso 1 1 d D U . . .
O1 O 0.0565(3) 0.7190(2) 0.62150(17) 0.0304(6) Uani 1 1 d . . . . .
O2 O 0.3514(3) 0.4091(3) 0.56290(19) 0.0349(7) Uani 1 1 d . . . . .
N1 N 0.0283(4) 0.7116(3) 0.4216(2) 0.0219(6) Uani 1 1 d . . . . .
C7 C 0.1748(4) 0.5666(3) 0.4183(2) 0.0212(7) Uani 1 1 d . . . . .
N3 N 0.2620(4) 0.4850(3) 0.44620(19) 0.0227(6) Uani 1 1 d . . . . .
N4 N 0.1475(4) 0.5819(3) 0.33356(19) 0.0238(6) Uani 1 1 d . . . . .
N2 N 0.2117(4) 0.5683(3) 0.59221(19) 0.0227(6) Uani 1 1 d . . . . .
C3 C 0.1163(4) 0.6516(3) 0.5676(2) 0.0209(7) Uani 1 1 d . . . . .
C2 C 0.1033(4) 0.6454(3) 0.4741(2) 0.0209(7) Uani 1 1 d . . . . .
C6 C 0.3218(5) 0.3940(3) 0.3802(2) 0.0299(8) Uani 1 1 d . . . . .
H6A H 0.2383 0.3399 0.3396 0.045 Uiso 1 1 calc R U . . .
H6B H 0.3878 0.3489 0.4112 0.045 Uiso 1 1 calc R U . . .
H6C H 0.3783 0.4335 0.3468 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2798(4) 0.4823(3) 0.5347(2) 0.0232(7) Uani 1 1 d . . . . .
C1 C 0.0591(4) 0.6713(3) 0.3391(2) 0.0241(7) Uani 1 1 d . . . . .
H1 H 0.0229 0.7022 0.2911 0.029 Uiso 1 1 calc R U . . .
H1N H -0.030(6) 0.760(5) 0.433(3) 0.036 Uiso 1 1 d . U . . .
F10 F 0.1659(3) 0.7809(3) 0.97347(18) 0.0465(7) Uani 1 1 d . . . . .
F8 F -0.2864(4) 0.8392(3) 0.79743(17) 0.0524(8) Uani 1 1 d . . . . .
F6 F -0.2313(3) 0.9462(3) 1.11120(17) 0.0468(7) Uani 1 1 d . . . . .
F7 F -0.3949(4) 0.9364(3) 0.9484(2) 0.0538(7) Uani 1 1 d . . . . .
O7 O 0.1977(3) 0.8976(3) 1.15803(18) 0.0354(7) Uani 1 1 d . . . . .
H7O H 0.2368 0.8938 1.2085 0.053 Uiso 1 1 calc R U . . .
F9 F -0.0029(4) 0.7672(3) 0.81172(18) 0.0561(8) Uani 1 1 d . . . . .
O8 O -0.0139(4) 0.8189(3) 1.1897(2) 0.0459(8) Uani 1 1 d . . . . .
C25 C -0.2590(5) 0.8959(4) 0.9550(3) 0.0367(9) Uani 1 1 d . . . . .
C28 C 0.0273(5) 0.8181(3) 0.9699(3) 0.0329(9) Uani 1 1 d . . . . .
C26 C -0.2013(6) 0.8483(3) 0.8786(3) 0.0376(10) Uani 1 1 d . . . . .
C23 C -0.0295(5) 0.8603(3) 1.0482(2) 0.0291(8) Uani 1 1 d . . . . .
C27 C -0.0592(6) 0.8104(4) 0.8858(3) 0.0377(10) Uani 1 1 d . . . . .
C24 C -0.1723(5) 0.8997(4) 1.0385(3) 0.0333(9) Uani 1 1 d . . . . .
C22 C 0.0533(5) 0.8562(3) 1.1402(2) 0.0306(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 N2 1.466(4) . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
F2 C11 1.336(5) . ?
F5 C14 1.333(4) . ?
F1 C10 1.337(5) . ?
F3 C12 1.328(4) . ?
O3 C8 1.307(5) . ?
O3 H3O 0.82 . ?
F4 C13 1.334(5) . ?
O4 C8 1.197(5) . ?
C10 C11 1.385(5) . ?
C10 C9 1.388(5) . ?
C14 C13 1.381(5) . ?
C14 C9 1.383(5) . ?
C13 C12 1.381(6) . ?
C12 C11 1.381(6) . ?
C9 C8 1.506(5) . ?
O5 C19 1.223(4) . ?
N8 C15 1.335(5) . ?
N8 C16 1.379(4) . ?
N8 H8N 0.901(7) . ?
N6 C21 1.369(4) . ?
N6 C19 1.375(5) . ?
N6 C20 1.467(4) . ?
O6 C17 1.217(5) . ?
C17 N7 1.411(4) . ?
C17 C16 1.425(5) . ?
N7 C19 1.394(4) . ?
N7 C18 1.478(4) . ?
N5 C15 1.333(5) . ?
N5 C21 1.368(4) . ?
C21 C16 1.370(5) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C15 H15 0.93 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
O1 C3 1.214(4) . ?
O2 C5 1.215(5) . ?
N1 C1 1.338(5) . ?
N1 C2 1.379(4) . ?
N1 H1N 0.80(6) . ?
C7 C2 1.362(5) . ?
C7 N4 1.365(4) . ?
C7 N3 1.366(4) . ?
N3 C5 1.375(4) . ?
N3 C6 1.468(4) . ?
N4 C1 1.332(5) . ?
N2 C5 1.404(4) . ?
N2 C3 1.405(4) . ?
C3 C2 1.430(5) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C1 H1 0.93 . ?
F10 C28 1.334(6) . ?
F8 C26 1.339(5) . ?
F6 C24 1.338(5) . ?
F7 C25 1.326(6) . ?
O7 C22 1.304(5) . ?
O7 H7O 0.82 . ?
F9 C27 1.335(5) . ?
O8 C22 1.201(5) . ?
C25 C26 1.380(7) . ?
C25 C24 1.389(6) . ?
C28 C27 1.384(6) . ?
C28 C23 1.391(6) . ?
C26 C27 1.365(7) . ?
C23 C24 1.379(6) . ?
C23 C22 1.516(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C8 O3 H3O 109.5 . . ?
F1 C10 C11 118.5(3) . . ?
F1 C10 C9 120.1(3) . . ?
C11 C10 C9 121.4(3) . . ?
F5 C14 C13 118.2(3) . . ?
F5 C14 C9 120.1(3) . . ?
C13 C14 C9 121.7(4) . . ?
F4 C13 C12 119.4(3) . . ?
F4 C13 C14 120.8(4) . . ?
C12 C13 C14 119.8(4) . . ?
F3 C12 C11 120.3(4) . . ?
F3 C12 C13 120.0(4) . . ?
C11 C12 C13 119.6(3) . . ?
C14 C9 C10 117.6(3) . . ?
C14 C9 C8 120.8(3) . . ?
C10 C9 C8 121.6(3) . . ?
F2 C11 C12 119.6(3) . . ?
F2 C11 C10 120.6(4) . . ?
C12 C11 C10 119.8(4) . . ?
O4 C8 O3 126.5(3) . . ?
O4 C8 C9 122.5(3) . . ?
O3 C8 C9 111.0(3) . . ?
C15 N8 C16 106.5(3) . . ?
C15 N8 H8N 128(4) . . ?
C16 N8 H8N 126(4) . . ?
C21 N6 C19 119.5(3) . . ?
C21 N6 C20 120.3(3) . . ?
C19 N6 C20 120.2(3) . . ?
O6 C17 N7 121.2(3) . . ?
O6 C17 C16 127.2(3) . . ?
N7 C17 C16 111.6(3) . . ?
C19 N7 C17 126.5(3) . . ?
C19 N7 C18 117.5(3) . . ?
C17 N7 C18 115.9(3) . . ?
C15 N5 C21 103.6(3) . . ?
N5 C21 N6 126.9(3) . . ?
N5 C21 C16 111.1(3) . . ?
N6 C21 C16 121.9(3) . . ?
C21 C16 N8 105.3(3) . . ?
C21 C16 C17 122.9(3) . . ?
N8 C16 C17 131.7(3) . . ?
O5 C19 N6 121.8(3) . . ?
O5 C19 N7 120.7(3) . . ?
N6 C19 N7 117.5(3) . . ?
N7 C18 H18A 109.5 . . ?
N7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C15 N8 113.3(3) . . ?
N5 C15 H15 123.3 . . ?
N8 C15 H15 123.3 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C2 106.8(3) . . ?
C1 N1 H1N 123(4) . . ?
C2 N1 H1N 130(4) . . ?
C2 C7 N4 110.8(3) . . ?
C2 C7 N3 123.0(3) . . ?
N4 C7 N3 126.2(3) . . ?
C7 N3 C5 119.0(3) . . ?
C7 N3 C6 119.9(3) . . ?
C5 N3 C6 120.8(3) . . ?
C1 N4 C7 104.5(3) . . ?
C5 N2 C3 126.8(3) . . ?
C5 N2 C4 117.1(3) . . ?
C3 N2 C4 116.1(3) . . ?
O1 C3 N2 122.1(3) . . ?
O1 C3 C2 126.6(3) . . ?
N2 C3 C2 111.3(3) . . ?
C7 C2 N1 105.6(3) . . ?
C7 C2 C3 122.6(3) . . ?
N1 C2 C3 131.8(3) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C5 N3 122.1(3) . . ?
O2 C5 N2 120.7(3) . . ?
N3 C5 N2 117.2(3) . . ?
N4 C1 N1 112.3(3) . . ?
N4 C1 H1 123.8 . . ?
N1 C1 H1 123.8 . . ?
C22 O7 H7O 109.5 . . ?
F7 C25 C26 120.6(4) . . ?
F7 C25 C24 120.8(4) . . ?
C26 C25 C24 118.6(4) . . ?
F10 C28 C27 117.9(4) . . ?
F10 C28 C23 120.8(4) . . ?
C27 C28 C23 121.3(4) . . ?
F8 C26 C27 120.4(4) . . ?
F8 C26 C25 119.3(4) . . ?
C27 C26 C25 120.3(4) . . ?
C24 C23 C28 117.0(4) . . ?
C24 C23 C22 119.9(4) . . ?
C28 C23 C22 122.9(4) . . ?
F9 C27 C26 119.9(4) . . ?
F9 C27 C28 120.0(5) . . ?
C26 C27 C28 120.1(4) . . ?
F6 C24 C23 120.2(4) . . ?
F6 C24 C25 117.2(4) . . ?
C23 C24 C25 122.5(4) . . ?
O8 C22 O7 125.9(4) . . ?
O8 C22 C23 120.6(4) . . ?
O7 C22 C23 113.4(3) . . ?


# END of CIF

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

data_thp-34diFBA-I
_database_code_depnum_ccdc_archive 'CCDC 1476648'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_mineral           'theophylline:34-difluorobenzoic acid'
_chemical_formula_moiety         '(C7 H8 N4 O2), (C7 H4 F2 O2)'
_chemical_formula_weight         338.27

_cell_length_a                   9.17878(43)
_cell_length_b                   10.55176(55)
_cell_length_c                   11.09567(51)
_cell_angle_alpha                125.2204(16)
_cell_angle_beta                 58.5444(30)
_cell_angle_gamma                109.9620(28)
_cell_volume                     747.641(68)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_prof_R_factor        0.0464
_pd_proc_ls_prof_wR_factor       0.0664
_pd_proc_ls_prof_wR_expected     0.0438
_refine_ls_matrix_type           full
_refine_ls_shift/su_max          <0.01
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    rigid
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_goodness_of_fit_all   1.517
_exptl_crystal_description       'microcrystaline powder'
_exptl_crystal_colour            white
_exptl_special_details           
;
Rietveld refinement treated each molecule as a separate rigid body.
The flourobenzoic acid was allowed the rotation of the carboxylic group.
Errors of atomic coordinates were estimated using the bootstrap method.
;

loop_
_symmetry_equiv_pos_as_xyz
'-x, -y, -z'
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C11 C 2 0.01769(34) 0.17385(40) 0.66625(41) 1 5.21(24)
C12 C 2 0.03803(41) 0.26828(42) 0.60766(41) 1 5.21(24)
C13 C 2 0.19928(44) 0.29655(34) 0.50133(37) 1 5.21(24)
C14 C 2 0.34179(37) 0.22943(32) 0.45315(42) 1 5.21(24)
C15 C 2 0.32152(30) 0.13471(30) 0.51184(45) 1 5.21(24)
C16 C 2 0.15989(31) 0.10642(30) 0.61840(39) 1 5.21(24)
C17 C 2 0.13726(34) 0.00577(30) 0.68123(43) 1 5.21(24)
O11 O 2 0.26149(41) -0.04506(57) 0.65027(68) 1 5.21(24)
O12 O 2 -0.01800(34) -0.03369(97) 0.7738(11) 1 5.21(24)
F11 F 2 0.49541(41) 0.25528(40) 0.35269(53) 1 5.21(24)
F12 F 2 0.21601(55) 0.38663(38) 0.44698(38) 1 5.21(24)
H11 H 2 -0.11082(35) 0.15338(50) 0.74981(48) 1 5.21(24)
H12 H 2 -0.07398(46) 0.32098(53) 0.64556(49) 1 5.21(24)
H13 H 2 0.43499(29) 0.08295(37) 0.47264(55) 1 5.21(24)
H14 H 2 0.00257(42) -0.09902(79) 0.79835(93) 1 5.21(24)
C1 C 2 0.19825(39) 0.25594(46) 1.03008(42) 1 5.21(24)
C2 C 2 0.15596(32) 0.35125(55) 1.00055(37) 1 5.21(24)
C3 C 2 0.28338(41) 0.41566(62) 0.89700(40) 1 5.21(24)
N1 N 2 0.45175(38) 0.37548(62) 0.82817(45) 1 5.21(24)
C4 C 2 0.49467(37) 0.28134(54) 0.85707(48) 1 5.21(24)
N2 N 2 0.36616(46) 0.22025(43) 0.95872(47) 1 5.21(24)
N3 N 2 0.04916(49) 0.21148(54) 1.13490(53) 1 5.21(24)
C5 C 2 -0.07832(36) 0.27899(66) 1.16647(54) 1 5.21(24)
N4 N 2 -0.02059(31) 0.36422(66) 1.08847(46) 1 5.21(24)
O1 O 2 0.64685(41) 0.25081(63) 0.79262(61) 1 5.21(24)
O2 O 2 0.25249(59) 0.49898(75) 0.86813(50) 1 5.21(24)
C6 C 2 0.40868(68) 0.12570(44) 0.98991(62) 1 5.21(24)
C7 C 2 0.58688(50) 0.43508(80) 0.72369(60) 1 5.21(24)
H1 H 2 -0.21347(39) 0.26812(79) 1.24535(67) 1 5.21(24)
H2 H 2 -0.08744(37) 0.42363(76) 1.09213(52) 1 5.21(24)
H3 H 2 0.54956(71) 0.10778(51) 0.91891(69) 1 5.21(24)
H4 H 2 0.33503(81) 0.01033(42) 0.95241(70) 1 5.21(24)
H5 H 2 0.37350(75) 0.18501(48) 1.12346(64) 1 5.21(24)
H6 H 2 0.71296(46) 0.39182(85) 0.67422(68) 1 5.21(24)
H7 H 2 0.59308(55) 0.56553(79) 0.79541(73) 1 5.21(24)
H8 H 2 0.55722(68) 0.39632(92) 0.62045(56) 1 5.21(24)
#END-END-END-END-END-END-END-END-END-END-END-END-END-END-END-END-END


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

data_thp-2346tetFBA
_database_code_depnum_ccdc_archive 'CCDC 1476649'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_mineral           'theophylline:2346-tetrafluorobenzoic acid'
_chemical_formula_moiety         '(C7 H8 N4 O2), (C7 H2 F4 O2)'
_chemical_formula_weight         374.25

_cell_length_a                   7.43730(14)
_cell_length_b                   7.32762(21)
_cell_length_c                   14.64086(43)
_cell_angle_alpha                85.7805(17)
_cell_angle_beta                 101.0840(18)
_cell_angle_gamma                101.4890(14)
_cell_volume                     766.804(35)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1


_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_prof_R_factor        0.0323
_pd_proc_ls_prof_wR_factor       0.0423
_pd_proc_ls_prof_wR_expected     0.0383
_refine_ls_matrix_type           full
_refine_ls_shift/su_max          <0.01
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    rigid
_refine_ls_number_parameters     71
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_goodness_of_fit_all   1.252
_exptl_crystal_description       'microcrystaline powder'
_exptl_crystal_colour            white
_exptl_special_details           
;
Rietveld refinement treated each molecule as a separate rigid body.
The flourobenzoic acid was allowed the rotation of the carboxylic group.
Errors of atomic coordinates were estimated using the bootstrap method.
;


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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C11 C 2 0.71860(60) 0.50944(56) 0.93813(37) 1 5.91(19)
C12 C 2 0.77523(70) 0.37890(52) 1.00727(38) 1 5.91(19)
C13 C 2 0.82628(68) 0.42907(56) 1.10052(35) 1 5.91(19)
C14 C 2 0.82104(55) 0.61120(59) 1.12545(32) 1 5.91(19)
C15 C 2 0.76361(44) 0.74219(56) 1.05508(33) 1 5.91(19)
C16 C 2 0.71207(48) 0.69191(57) 0.96101(35) 1 5.91(19)
C17 C 2 0.65309(64) 0.82926(67) 0.88925(36) 1 5.91(19)
O18 O 2 0.6927(16) 1.00100(67) 0.89087(58) 1 5.91(19)
O19 O 2 0.5397(10) 0.75433(84) 0.81111(24) 1 5.91(19)
F11 F 2 0.75933(56) 0.91438(59) 1.07976(34) 1 5.91(19)
F12 F 2 0.87020(71) 0.65990(70) 1.21533(30) 1 5.91(19)
F13 F 2 0.88077(92) 0.30430(65) 1.16719(36) 1 5.91(19)
F15 F 2 0.67017(79) 0.45765(65) 0.84890(39) 1 5.91(19)
H14 H 2 0.77951(90) 0.23739(52) 0.98824(41) 1 5.91(19)
H10 H 2 0.5076(10) 0.85455(94) 0.76747(25) 1 5.91(19)
C1 C 2 0.35172(44) -0.00120(57) 0.59763(20) 1 5.91(19)
C2 C 2 0.38288(51) 0.17668(53) 0.54991(17) 1 5.91(19)
C3 C 2 0.29934(61) 0.20764(55) 0.45341(18) 1 5.91(19)
N1 N 2 0.18481(55) 0.04719(61) 0.41132(21) 1 5.91(19)
C4 C 2 0.15353(51) -0.12956(56) 0.45810(30) 1 5.91(19)
N2 N 2 0.23738(50) -0.15380(54) 0.55256(30) 1 5.91(19)
N3 N 2 0.45081(48) 0.01175(71) 0.68962(19) 1 5.91(19)
C5 C 2 0.53845(51) 0.19332(73) 0.69606(17) 1 5.91(19)
N4 N 2 0.50195(59) 0.29817(60) 0.61390(20) 1 5.91(19)
O1 O 2 0.05087(61) -0.26629(62) 0.41640(39) 1 5.91(19)
O2 O 2 0.32266(80) 0.35945(61) 0.40925(23) 1 5.91(19)
C6 C 2 0.20776(68) -0.33305(59) 0.60039(42) 1 5.91(19)
C7 C 2 0.09639(67) 0.06535(78) 0.31511(22) 1 5.91(19)
H1 H 2 0.62912(57) 0.25256(88) 0.75932(19) 1 5.91(19)
H2 H 2 0.54880(73) 0.43180(60) 0.60095(28) 1 5.91(19)
H3 H 2 0.10875(78) -0.43664(57) 0.55287(50) 1 5.91(19)
H4 H 2 0.14767(68) -0.32106(77) 0.66390(42) 1 5.91(19)
H5 H 2 0.34449(78) -0.38099(59) 0.62231(44) 1 5.91(19)
H6 H 2 0.00635(66) -0.07033(84) 0.29092(29) 1 5.91(19)
H7 H 2 0.20693(76) 0.10923(92) 0.27113(18) 1 5.91(19)
H8 H 2 0.00890(76) 0.17595(81) 0.30807(23) 1 5.91(19)
#END-END-END-END-END-END-END-END-END-END-END-END-END-END-END-END-END

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

data_thp-2356tetFBA
_database_code_depnum_ccdc_archive 'CCDC 1476650'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
_chemical_name_mineral           'theophylline:2356-tetrafluorobenzoic acid'
_chemical_formula_moiety         '(C7 H8 N4 O2), (C7 H2 F4 O2)'
_chemical_formula_weight         374.25
_cell_length_a                   3.94083(11)
_cell_length_b                   13.00822(50)
_cell_length_c                   29.9781(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.2242(30)
_cell_angle_gamma                90
_cell_volume                     1535.614(99)
_cell_formula_units_Z            4
_cell_measurement_temperature    293

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c


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


_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_prof_R_factor        0.0415
_pd_proc_ls_prof_wR_factor       0.0534
_pd_proc_ls_prof_wR_expected     0.0459
_refine_ls_matrix_type           full
_refine_ls_shift/su_max          <0.01
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    rigid
_refine_ls_number_parameters     56
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_goodness_of_fit_all   1.16
_exptl_crystal_description       'microcrystaline powder'
_exptl_crystal_colour            white
_exptl_special_details           
;
Rietveld refinement treated each molecule as a separate rigid body.
The flourobenzoic acid was allowed the rotation of the carboxylic group.
Errors of atomic coordinates were estimated using the bootstrap method.
;


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C11 C 4 0.71926(56) 0.54736(23) 0.687032(74) 1 7.42(15)
C12 C 4 0.85481(89) 0.63001(25) 0.71315(10) 1 7.42(15)
C13 C 4 0.9000(10) 0.61984(37) 0.75950(10) 1 7.42(15)
C14 C 4 0.8113(11) 0.52773(45) 0.780280(77) 1 7.42(15)
C15 C 4 0.67534(88) 0.44434(38) 0.75458(11) 1 7.42(15)
C16 C 4 0.62961(44) 0.45448(27) 0.70786(11) 1 7.42(15)
C17 C 4 0.48899(58) 0.36789(27) 0.68160(17) 1 7.42(15)
O18 O 4 0.5700(20) 0.27630(26) 0.68366(42) 1 7.42(15)
O19 O 4 0.2370(22) 0.39408(36) 0.65132(27) 1 7.42(15)
F11 F 4 0.5924(13) 0.35680(47) 0.77541(17) 1 7.42(15)
F12 F 4 0.8546(16) 0.51763(61) 0.825009(79) 1 7.42(15)
F14 F 4 0.9401(13) 0.71874(22) 0.69295(16) 1 7.42(15)
F15 F 4 0.67849(87) 0.55924(27) 0.642541(74) 1 7.42(15)
H13 H 4 1.0052(13) 0.68411(43) 0.77961(14) 1 7.42(15)
H10 H 4 0.1587(22) 0.33268(38) 0.63550(25) 1 7.42(15)
C1 C 4 0.09481(94) 0.24834(26) 0.546657(78) 1 7.42(15)
C2 C 4 0.20845(66) 0.16113(19) 0.52224(11) 1 7.42(15)
C3 C 4 0.13408(68) 0.14785(31) 0.47481(12) 1 7.42(15)
N1 N 4 -0.05866(96) 0.22854(47) 0.455088(73) 1 7.42(15)
C4 C 4 -0.1726(13) 0.31509(38) 0.47907(15) 1 7.42(15)
N2 N 4 -0.0935(13) 0.32532(21) 0.52540(15) 1 7.42(15)
N3 N 4 0.2044(13) 0.23975(55) 0.591679(80) 1 7.42(15)
C5 C 4 0.3790(13) 0.14947(62) 0.59378(14) 1 7.42(15)
N4 N 4 0.3887(10) 0.09936(39) 0.55289(19) 1 7.42(15)
O1 O 4 -0.3440(18) 0.38368(57) 0.45951(23) 1 7.42(15)
O2 O 4 0.2272(10) 0.07342(43) 0.45231(21) 1 7.42(15)
C6 C 4 -0.2106(19) 0.41245(30) 0.55011(26) 1 7.42(15)
C7 C 4 -0.1451(14) 0.22140(79) 0.407934(77) 1 7.42(15)
H1 H 4 0.5008(17) 0.11856(85) 0.62445(18) 1 7.42(15)
H2 H 4 0.4982(13) 0.03323(41) 0.54580(27) 1 7.42(15)
H3 H 4 -0.3516(22) 0.46667(33) 0.52690(33) 1 7.42(15)
H4 H 4 0.0131(21) 0.45295(36) 0.56638(29) 1 7.42(15)
H5 H 4 -0.3836(18) 0.38555(44) 0.57661(24) 1 7.42(15)
H6 H 4 -0.2907(17) 0.29113(91) 0.39631(13) 1 7.42(15)
H7 H 4 -0.3028(13) 0.15061(89) 0.40155(12) 1 7.42(15)
H8 H 4 0.0947(16) 0.21458(84) 0.389065(73) 1 7.42(15)
#END-END-END-END-END-END-END-END-END-END-END-END-END-END-END-END-END



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

data_thp-34diFBA-II
_database_code_depnum_ccdc_archive 'CCDC 1476651'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_date             2016-04-25T12:22:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H4 F2 O2'
_chemical_formula_sum            'C14 H12 F2 N4 O4'
_chemical_formula_weight         338.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1293(3)
_cell_length_b                   9.7717(4)
_cell_length_c                   10.0297(4)
_cell_angle_alpha                110.888(3)
_cell_angle_beta                 109.827(3)
_cell_angle_gamma                102.048(3)
_cell_volume                     728.97(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(3)
_cell_measurement_reflns_used    7519
_cell_measurement_theta_min      5.2040
_cell_measurement_theta_max      73.4450
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.413
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             348

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.86478
_exptl_absorpt_correction_T_max  1.00000

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(3)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_number            10103
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.227
_diffrn_reflns_theta_max         66.54
_diffrn_reflns_theta_full        66.54
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             2577
_reflns_number_gt                2371
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.2439P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2577
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.18618(18) 0.77531(17) 0.11535(17) 0.0271(3) Uani 1 1 d . . . . .
H1 H 1.2212 0.7624 0.0362 0.032 Uiso 1 1 calc R U . . .
C2 C 1.19342(17) 0.85131(15) 0.34985(16) 0.0219(3) Uani 1 1 d . . . . .
C3 C 1.23528(17) 0.91599(15) 0.51569(16) 0.0219(3) Uani 1 1 d . . . . .
C4 C 1.12118(19) 0.91618(18) 0.70547(17) 0.0284(3) Uani 1 1 d . . . . .
H4A H 1.0153 0.877 0.7049 0.043 Uiso 0.5 1 calc R U P . .
H4B H 1.1959 0.8726 0.7532 0.043 Uiso 0.5 1 calc R U P . .
H4C H 1.1692 1.0293 0.7662 0.043 Uiso 0.5 1 calc R U P . .
H4D H 1.2383 0.9756 0.778 0.043 Uiso 0.5 1 calc R U P . .
H4E H 1.0577 0.98 0.7296 0.043 Uiso 0.5 1 calc R U P . .
H4F H 1.0844 0.8232 0.7167 0.043 Uiso 0.5 1 calc R U P . .
C5 C 0.92838(17) 0.77766(16) 0.42164(17) 0.0239(3) Uani 1 1 d . . . . .
C6 C 0.72844(18) 0.6288(2) 0.13721(19) 0.0352(4) Uani 1 1 d . . . . .
H6A H 0.6532 0.6175 0.1836 0.053 Uiso 0.5 1 calc R U P . .
H6B H 0.6965 0.6799 0.0723 0.053 Uiso 0.5 1 calc R U P . .
H6C H 0.723 0.5264 0.0721 0.053 Uiso 0.5 1 calc R U P . .
H6D H 0.7286 0.5984 0.0351 0.053 Uiso 0.5 1 calc R U P . .
H6E H 0.6853 0.536 0.1464 0.053 Uiso 0.5 1 calc R U P . .
H6F H 0.6588 0.6895 0.1466 0.053 Uiso 0.5 1 calc R U P . .
C7 C 1.03292(17) 0.75905(15) 0.23177(16) 0.0223(3) Uani 1 1 d . . . . .
N1 N 1.29025(14) 0.85988(13) 0.27167(13) 0.0245(3) Uani 1 1 d . . . . .
H1N H 1.397 0.9099 0.315 0.029 Uiso 1 1 calc R U . . .
N2 N 1.09542(14) 0.86990(13) 0.54057(14) 0.0232(3) Uani 1 1 d . . . . .
N3 N 0.90000(14) 0.72433(13) 0.26463(14) 0.0245(3) Uani 1 1 d . . . . .
N4 N 1.02685(15) 0.71117(14) 0.08429(14) 0.0267(3) Uani 1 1 d . . . . .
O1 O 1.37491(12) 1.00152(12) 0.62902(11) 0.0271(2) Uani 1 1 d . . . . .
O2 O 0.81647(13) 0.74928(13) 0.45811(13) 0.0326(3) Uani 1 1 d . . . . .
C8 C 0.18034(18) 0.50330(16) 0.32480(16) 0.0247(3) Uani 1 1 d . . . . .
C9 C 0.32525(17) 0.60416(15) 0.48690(16) 0.0229(3) Uani 1 1 d . . . . .
C10 C 0.48579(18) 0.67151(16) 0.50519(16) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.5031 0.6535 0.4153 0.029 Uiso 1 1 calc R U . . .
C11 C 0.61984(18) 0.76528(17) 0.65685(17) 0.0264(3) Uani 1 1 d . . . . .
H11 H 0.7272 0.8103 0.6697 0.032 Uiso 1 1 calc R U . . .
C12 C 0.59070(19) 0.79014(17) 0.78746(17) 0.0288(3) Uani 1 1 d . . . . .
C13 C 0.4314(2) 0.72351(18) 0.76919(17) 0.0296(3) Uani 1 1 d . . . . .
C14 C 0.29752(18) 0.63004(16) 0.62061(17) 0.0260(3) Uani 1 1 d . . . . .
H14 H 0.1909 0.585 0.6093 0.031 Uiso 1 1 calc R U . . .
F1 F 0.41072(13) 0.75303(13) 0.90335(11) 0.0453(3) Uani 1 1 d . . . . .
F2 F 0.71798(12) 0.88060(12) 0.93624(10) 0.0444(3) Uani 1 1 d . . . . .
O3 O 0.03605(13) 0.45066(13) 0.30161(13) 0.0337(3) Uani 1 1 d . . . . .
O4 O 0.22515(13) 0.47837(13) 0.20840(12) 0.0323(3) Uani 1 1 d . . . . .
H4 H 0.1424 0.4195 0.1219 0.048 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.3336(19) . ?
C1 N1 1.3348(18) . ?
C1 H1 0.93 . ?
C2 C7 1.3683(19) . ?
C2 N1 1.3746(18) . ?
C2 C3 1.4250(19) . ?
C3 O1 1.2290(17) . ?
C3 N2 1.3970(18) . ?
C4 N2 1.4675(17) . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C4 H4D 0.96 . ?
C4 H4E 0.96 . ?
C4 H4F 0.96 . ?
C5 O2 1.2091(17) . ?
C5 N3 1.3785(18) . ?
C5 N2 1.4094(18) . ?
C6 N3 1.4625(18) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C6 H6D 0.96 . ?
C6 H6E 0.96 . ?
C6 H6F 0.96 . ?
C7 N4 1.3601(18) . ?
C7 N3 1.3694(18) . ?
N1 H1N 0.86 . ?
C8 O3 1.2157(18) . ?
C8 O4 1.3238(17) . ?
C8 C9 1.490(2) . ?
C9 C14 1.393(2) . ?
C9 C10 1.394(2) . ?
C10 C11 1.388(2) . ?
C10 H10 0.93 . ?
C11 C12 1.372(2) . ?
C11 H11 0.93 . ?
C12 F2 1.3464(17) . ?
C12 C13 1.382(2) . ?
C13 F1 1.3594(17) . ?
C13 C14 1.370(2) . ?
C14 H14 0.93 . ?
O4 H4 0.82 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 113.05(12) . . ?
N4 C1 H1 123.5 . . ?
N1 C1 H1 123.5 . . ?
C7 C2 N1 105.46(12) . . ?
C7 C2 C3 122.68(13) . . ?
N1 C2 C3 131.85(12) . . ?
O1 C3 N2 121.04(12) . . ?
O1 C3 C2 126.95(13) . . ?
N2 C3 C2 112.00(12) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C4 H4D 109.5 . . ?
H4A C4 H4D 141.1 . . ?
H4B C4 H4D 56.3 . . ?
H4C C4 H4D 56.3 . . ?
N2 C4 H4E 109.5 . . ?
H4A C4 H4E 56.3 . . ?
H4B C4 H4E 141.1 . . ?
H4C C4 H4E 56.3 . . ?
H4D C4 H4E 109.5 . . ?
N2 C4 H4F 109.5 . . ?
H4A C4 H4F 56.3 . . ?
H4B C4 H4F 56.3 . . ?
H4C C4 H4F 141.1 . . ?
H4D C4 H4F 109.5 . . ?
H4E C4 H4F 109.5 . . ?
O2 C5 N3 122.45(13) . . ?
O2 C5 N2 120.57(13) . . ?
N3 C5 N2 116.98(12) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C6 H6D 109.5 . . ?
H6A C6 H6D 141.1 . . ?
H6B C6 H6D 56.3 . . ?
H6C C6 H6D 56.3 . . ?
N3 C6 H6E 109.5 . . ?
H6A C6 H6E 56.3 . . ?
H6B C6 H6E 141.1 . . ?
H6C C6 H6E 56.3 . . ?
H6D C6 H6E 109.5 . . ?
N3 C6 H6F 109.5 . . ?
H6A C6 H6F 56.3 . . ?
H6B C6 H6F 56.3 . . ?
H6C C6 H6F 141.1 . . ?
H6D C6 H6F 109.5 . . ?
H6E C6 H6F 109.5 . . ?
N4 C7 C2 111.13(12) . . ?
N4 C7 N3 126.60(12) . . ?
C2 C7 N3 122.27(12) . . ?
C1 N1 C2 106.55(11) . . ?
C1 N1 H1N 126.7 . . ?
C2 N1 H1N 126.7 . . ?
C3 N2 C5 126.56(12) . . ?
C3 N2 C4 118.34(11) . . ?
C5 N2 C4 115.07(11) . . ?
C7 N3 C5 119.40(11) . . ?
C7 N3 C6 121.72(12) . . ?
C5 N3 C6 118.87(12) . . ?
C1 N4 C7 103.81(11) . . ?
O3 C8 O4 123.52(13) . . ?
O3 C8 C9 123.67(13) . . ?
O4 C8 C9 112.80(12) . . ?
C14 C9 C10 120.41(13) . . ?
C14 C9 C8 118.71(13) . . ?
C10 C9 C8 120.89(12) . . ?
C11 C10 C9 120.37(13) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 118.63(14) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
F2 C12 C11 120.11(14) . . ?
F2 C12 C13 118.93(13) . . ?
C11 C12 C13 120.96(14) . . ?
F1 C13 C14 120.54(14) . . ?
F1 C13 C12 118.11(13) . . ?
C14 C13 C12 121.35(14) . . ?
C13 C14 C9 118.29(14) . . ?
C13 C14 H14 120.9 . . ?
C9 C14 H14 120.9 . . ?
C8 O4 H4 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


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

data_thp-2FBA-MeNO2
_database_code_depnum_ccdc_archive 'CCDC 1476652'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_chemical_name_systematic        
; ?
;
_chemical_name_common            'theophylline:2-FBA cocrystal MeNO2 solvate'
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H5 F O2, C H3 N O2'
_chemical_formula_structural     'C7 H8 N4 O2, C7 H5 F O2, C H3 N O2'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C15 H16 F N5 O6'
_chemical_formula_weight         381.32
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and 
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_length_neutron # include if applicable
? ? ? ? ? ?

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.00003(28)
_cell_length_b                   25.55132(99)
_cell_length_c                   8.73449(28)
_cell_angle_alpha                90
_cell_angle_beta                 105.0710(21)
_cell_angle_gamma                90
_cell_volume                     1724.02(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_theta_min      2
_cell_measurement_theta_max      60
_cell_measurement_reflns_used    20
_exptl_crystal_density_diffrn    1.4691(1)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             756

_cell_special_details            
; ?
;



# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 'borosilicate capillary'
;
_pd_spec_mount_mode              transmission

_pd_spec_shape                   cylinder

_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions



_pd_prep_temperature             293


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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_source_voltage           40
_diffrn_source_current           30
_diffrn_measurement_device_type  'Stoe StadiP'
_diffrn_detector                 'Single photon counting'
_diffrn_detector_type            'DECTRIS MYTHEN 1K'
_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)

_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  none

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        3861
_pd_meas_2theta_range_min        2.000
_pd_meas_2theta_range_max        59.900
_pd_meas_2theta_range_inc        0.015



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

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'


_pd_proc_ls_prof_R_factor        0.051
_pd_proc_ls_prof_wR_factor       0.065
_pd_proc_ls_prof_wR_expected     0.049
_refine_ls_R_I_factor            0.018


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     48
_refine_ls_number_restraints     0
_refine_ls_number_constraints    111

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   1.329


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        59.9
_pd_proc_2theta_range_inc        0.015
_pd_proc_wavelength              1.5406

# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting 
# of one data block containing a single powder profile. The value of 
# _pd_block_diffractogram_id is used to associate each refinement with 
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template 
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given 
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?




# The following items are used to identify the programs used.

_computing_data_collection       "X'Pert Data Collector (Panalytical)"
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'TOPAS Academic (Coelho 2007)'
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C2 C -0.23109(64) 0.04324(17) -0.40090(54) 1 8.19(20)
N2 N -0.20811(92) -0.01016(17) -0.39323(80) 1 8.19(20)
C1 C -0.3316(10) -0.03015(17) -0.33098(87) 1 8.19(20)
N1 N -0.43481(84) 0.00719(22) -0.29653(67) 1 8.19(20)
C6 C -0.37249(57) 0.05284(18) -0.34022(40) 1 8.19(20)
N4 N -0.43295(52) 0.10228(21) -0.32791(40) 1 8.19(20)
C5 C -0.35054(67) 0.14519(16) -0.37574(59) 1 8.19(20)
N3 N -0.20555(71) 0.13404(19) -0.43391(71) 1 8.19(20)
C3 C -0.13749(65) 0.08443(23) -0.45077(69) 1 8.19(20)
C7 C -0.58145(63) 0.11021(33) -0.26193(63) 1 8.19(20)
O2 O -0.40080(93) 0.19020(18) -0.36634(86) 1 8.19(20)
C4 C -0.1139(10) 0.17839(26) -0.4815(11) 1 8.19(20)
O1 O -0.00749(81) 0.08039(34) -0.50304(98) 1 8.19(20)
H1 H -0.3440(13) -0.06595(17) -0.3133(11) 1 8.19(20)
H2 H -0.1283(11) -0.02834(22) -0.42559(99) 1 8.19(20)
H3 H 0.00355(98) 0.17804(30) -0.4222(13) 1 8.19(20)
H4 H -0.1164(12) 0.17518(33) -0.5902(11) 1 8.19(20)
H5 H -0.1692(12) 0.20947(22) -0.4626(12) 1 8.19(20)
H6 H -0.55605(80) 0.09650(38) -0.15731(62) 1 8.19(20)
H7 H -0.60240(74) 0.14658(35) -0.26028(77) 1 8.19(20)
H8 H -0.68073(56) 0.09329(37) -0.32615(77) 1 8.19(20)
C9 C 0.18755(69) -0.40260(15) -0.56969(57) 1 8.19(20)
C10 C 0.05807(89) -0.43512(22) -0.53808(90) 1 8.19(20)
C11 C -0.06928(92) -0.41581(39) -0.4701(11) 1 8.19(20)
C12 C -0.0697(10) -0.36258(41) -0.43122(98) 1 8.19(20)
C13 C 0.0570(12) -0.32914(26) -0.46008(83) 1 8.19(20)
C14 C 0.18272(93) -0.34931(15) -0.52862(64) 1 8.19(20)
C8 C 0.32064(76) -0.42440(25) -0.64557(54) 1 8.19(20)
F1 F 0.3024(12) -0.31541(20) -0.55293(87) 1 8.19(20)
O3 O 0.3032(12) -0.47568(25) -0.67538(83) 1 8.19(20)
O4 O 0.43519(73) -0.39788(39) -0.67760(63) 1 8.19(20)
H10 H 0.0589(12) -0.47052(21) -0.5663(11) 1 8.19(20)
H11 H -0.1548(11) -0.43839(49) -0.4510(14) 1 8.19(20)
H12 H -0.1551(12) -0.34867(53) -0.3864(12) 1 8.19(20)
H13 H 0.0594(16) -0.29345(28) -0.4335(10) 1 8.19(20)
H9 H 0.3864(13) -0.48601(36) -0.71867(88) 1 8.19(20)
N5 N 0.26845(79) 0.20540(26) 0.31921(63) 1 8.19(20)
O5 O 0.2543(21) 0.16033(29) 0.3545(17) 1 8.19(20)
O6 O 0.1813(15) 0.24103(39) 0.3492(20) 1 8.19(20)
C15 C 0.4004(14) 0.21939(71) 0.2313(14) 1 8.19(20)
H14 H 0.4633(18) 0.18912(92) 0.2195(21) 1 8.19(20)
H15 H 0.3381(24) 0.23325(92) 0.1322(14) 1 8.19(20)
H16 H 0.4711(17) 0.24605(80) 0.2898(22) 1 8.19(20)


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


# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N2 1.376(6)
C2 C6 1.390(7)
C2 C3 1.424(8)
N2 C1 1.35(1)
N2 H2 0.89(1)
C1 N1 1.346(9)
C1 H1 0.937(7)
N1 C6 1.361(8)
C6 N4 1.367(7)
N4 C5 1.398(7)
N4 C7 1.463(7)
C5 N3 1.411(9)
C5 O2 1.228(7)
N3 C3 1.402(8)
N3 C4 1.47(1)
C3 O1 1.24(1)
C7 H6 0.950(8)
C7 H7 0.95(1)
C7 H8 0.949(8)
C4 H3 0.95(1)
C4 H4 0.95(1)
C4 H5 0.94(1)
C9 C10 1.410(9)
C9 C14 1.411(6)
C9 C8 1.500(8)
C10 C11 1.40(1)
C10 H10 0.938(8)
C11 C12 1.40(1)
C11 H11 0.94(1)
C12 C13 1.40(1)
C12 H12 0.94(1)
C13 C14 1.40(1)
C13 H13 0.94(1)
C14 F1 1.35(1)
C8 O3 1.336(9)
C8 O4 1.23(1)
O3 H9 0.89(1)
N5 O5 1.21(1)
N5 O6 1.22(1)
N5 C15 1.50(1)
C15 H14 0.94(3)
C15 H15 0.95(2)
C15 H16 0.95(2)






loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C2 C6 105.5(4)
N2 C2 C3 132.3(5)
C6 C2 C3 122.1(4)
C2 N2 C1 107.0(5)
C2 N2 H2 126.7(8)
C1 N2 H2 126.2(8)
N2 C1 N1 112.2(6)
N2 C1 H1 123.9(8)
N1 C1 H1 123.9(8)
C1 N1 C6 104.7(5)
C2 C6 N1 110.4(4)
C2 C6 N4 122.2(4)
N1 C6 N4 127.4(4)
C6 N4 C5 119.8(4)
C6 N4 C7 119.9(4)
C5 N4 C7 120.2(4)
N4 C5 N3 116.4(4)
N4 C5 O2 121.8(5)
N3 C5 O2 121.8(5)
C5 N3 C3 126.7(5)
C5 N3 C4 117.7(5)
C3 N3 C4 115.6(5)
C2 C3 N3 112.7(5)
C2 C3 O1 127.4(6)
N3 C3 O1 119.9(6)
N4 C7 H6 109.6(7)
N4 C7 H7 107.9(7)
N4 C7 H8 110.2(7)
H6 C7 H7 110.0(9)
H6 C7 H8 109.7(9)
H7 C7 H8 109.4(9)
N3 C4 H3 109.6(9)
N3 C4 H4 109.6(9)
N3 C4 H5 108.0(9)
H3 C4 H4 108(1)
H3 C4 H5 111(1)
H4 C4 H5 111(1)
C10 C9 C14 116.7(5)
C10 C9 C8 120.6(5)
C14 C9 C8 122.7(5)
C9 C10 C11 122.0(6)
C9 C10 H10 117.5(8)
C11 C10 H10 120.6(9)
C10 C11 C12 119.6(8)
C10 C11 H11 120(1)
C12 C11 H11 120(1)
C11 C12 C13 120.1(8)
C11 C12 H12 121(1)
C13 C12 H12 119(1)
C12 C13 C14 119.3(7)
C12 C13 H13 121(1)
C14 C13 H13 119.6(9)
C9 C14 C13 122.4(6)
C9 C14 F1 120.8(5)
C13 C14 F1 116.8(6)
C9 C8 O3 113.6(5)
C9 C8 O4 123.6(6)
O3 C8 O4 122.9(7)
C8 O3 H9 108.8(9)
O5 N5 O6 124(1)
O5 N5 C15 118.9(9)
O6 N5 C15 116.8(9)
N5 C15 H14 109(2)
N5 C15 H15 106(2)
N5 C15 H16 107(2)
H14 C15 H15 112(2)
H14 C15 H16 113(2)
H15 C15 H16 109(2)

