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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Ciprofloxacin diflunisal salt'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 F3 N3 O6'
_chemical_formula_weight         581.54

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

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

_cell_length_a                   7.116(2)
_cell_length_b                   9.994(4)
_cell_length_c                   19.147(7)
_cell_angle_alpha                81.470(9)
_cell_angle_beta                 82.505(8)
_cell_angle_gamma                87.191(8)
_cell_volume                     1334.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3387
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      23.89

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.685
_exptl_crystal_size_mid          0.432
_exptl_crystal_size_min          0.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14508
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.08
_diffrn_reflns_theta_max         25.12
_reflns_number_total             4618
_reflns_number_gt                2845
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.7100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4618
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_restrained_S_all      0.853
_refine_ls_shift/su_max          0.000
_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
C9 C 0.7663(3) 0.5620(2) 0.94523(12) 0.0336(5) Uani 1 1 d . . .
C8 C 0.8009(3) 0.5865(3) 0.87083(12) 0.0388(6) Uani 1 1 d . . .
H8 H 0.7978 0.6751 0.8478 0.047 Uiso 1 1 calc R . .
C4 C 0.7647(3) 0.4287(3) 0.98137(13) 0.0376(6) Uani 1 1 d . . .
C5 C 0.8074(3) 0.3225(3) 0.94085(14) 0.0450(6) Uani 1 1 d . . .
H5 H 0.8089 0.2335 0.9635 0.054 Uiso 1 1 calc R . .
C6 C 0.8462(3) 0.3485(3) 0.86935(15) 0.0466(7) Uani 1 1 d . . .
C3 C 0.7200(3) 0.3994(3) 1.05790(13) 0.0417(6) Uani 1 1 d . . .
C2 C 0.6863(3) 0.5145(3) 1.09482(13) 0.0418(6) Uani 1 1 d . . .
C7 C 0.8402(3) 0.4804(3) 0.83036(13) 0.0407(6) Uani 1 1 d . . .
C10 C 0.6878(3) 0.6418(3) 1.05707(12) 0.0398(6) Uani 1 1 d . . .
H10 H 0.6607 0.7145 1.0823 0.048 Uiso 1 1 calc R . .
C15 C 0.7035(3) 0.8081(3) 0.95077(13) 0.0411(6) Uani 1 1 d . . .
H15 H 0.5876 0.8287 0.9282 0.049 Uiso 1 1 calc R . .
C23 C 0.6113(4) 0.0925(3) 0.38628(14) 0.0481(7) Uani 1 1 d . . .
C19 C 0.4966(3) 0.2443(3) 0.47234(13) 0.0447(6) Uani 1 1 d . . .
C25 C 0.5812(4) 0.0349(3) 0.32172(15) 0.0490(7) Uani 1 1 d . . .
C29 C 0.3662(4) -0.0429(3) 0.24839(16) 0.0612(8) Uani 1 1 d . . .
H29 H 0.2438 -0.0623 0.2418 0.073 Uiso 1 1 calc R . .
C18 C 0.3463(4) 0.3419(3) 0.49843(15) 0.0548(7) Uani 1 1 d . . .
C14 C 1.1113(4) 0.5963(3) 0.66140(14) 0.0550(7) Uani 1 1 d . . .
H14A H 1.1515 0.6800 0.6320 0.066 Uiso 1 1 calc R . .
H14B H 1.2184 0.5565 0.6845 0.066 Uiso 1 1 calc R . .
C24 C 0.4799(3) 0.1866(3) 0.41225(14) 0.0469(7) Uani 1 1 d . . .
H24 H 0.3759 0.2120 0.3880 0.056 Uiso 1 1 calc R . .
C30 C 0.4010(4) 0.0036(3) 0.30961(15) 0.0552(8) Uani 1 1 d . . .
H30 H 0.2995 0.0145 0.3444 0.066 Uiso 1 1 calc R . .
C20 C 0.6548(4) 0.2086(3) 0.50813(15) 0.0519(7) Uani 1 1 d . . .
C22 C 0.7653(4) 0.0566(3) 0.42422(17) 0.0623(8) Uani 1 1 d . . .
H22 H 0.8546 -0.0076 0.4092 0.075 Uiso 1 1 calc R . .
C13 C 0.9510(4) 0.6275(3) 0.71787(14) 0.0546(7) Uani 1 1 d . . .
H13A H 0.9969 0.6817 0.7498 0.065 Uiso 1 1 calc R . .
H13B H 0.8497 0.6784 0.6955 0.065 Uiso 1 1 calc R . .
C21 C 0.7875(4) 0.1145(4) 0.48341(18) 0.0695(9) Uani 1 1 d . . .
H21 H 0.8927 0.0902 0.5072 0.083 Uiso 1 1 calc R . .
C11 C 0.8113(4) 0.4139(4) 0.71130(15) 0.0612(8) Uani 1 1 d . . .
H11A H 0.7110 0.4612 0.6868 0.073 Uiso 1 1 calc R . .
H11B H 0.7600 0.3324 0.7399 0.073 Uiso 1 1 calc R . .
C1 C 0.6428(4) 0.5014(4) 1.17388(15) 0.0546(8) Uani 1 1 d . . .
C12 C 0.9731(4) 0.3770(3) 0.65768(16) 0.0616(8) Uani 1 1 d . . .
H12A H 1.0702 0.3252 0.6821 0.074 Uiso 1 1 calc R . .
H12B H 0.9277 0.3215 0.6263 0.074 Uiso 1 1 calc R . .
C28 C 0.5158(4) -0.0597(3) 0.19767(15) 0.0556(8) Uani 1 1 d . . .
C16 C 0.7725(4) 0.9197(3) 0.98312(16) 0.0562(7) Uani 1 1 d . . .
H16A H 0.8339 0.8956 1.0258 0.067 Uiso 1 1 calc R . .
H16B H 0.6981 1.0038 0.9811 0.067 Uiso 1 1 calc R . .
C26 C 0.7249(4) 0.0130(3) 0.26776(17) 0.0606(8) Uani 1 1 d . . .
C17 C 0.8740(4) 0.8832(3) 0.91508(15) 0.0518(7) Uani 1 1 d . . .
H17A H 0.9968 0.8369 0.9165 0.062 Uiso 1 1 calc R . .
H17B H 0.8610 0.9452 0.8718 0.062 Uiso 1 1 calc R . .
C27 C 0.6964(4) -0.0333(3) 0.20598(17) 0.0648(9) Uani 1 1 d . . .
H27 H 0.7970 -0.0461 0.1712 0.078 Uiso 1 1 calc R . .
O3 O 0.7099(3) 0.27865(19) 1.08963(10) 0.0544(5) Uani 1 1 d . . .
O5 O 0.3697(3) 0.3895(2) 0.55474(11) 0.0700(6) Uani 1 1 d . . .
O2 O 0.6297(3) 0.3741(3) 1.20748(11) 0.0710(7) Uani 1 1 d . . .
O1 O 0.6211(3) 0.5965(3) 1.20628(11) 0.0758(7) Uani 1 1 d . . .
O6 O 0.6811(3) 0.2617(3) 0.56677(12) 0.0761(7) Uani 1 1 d . . .
O4 O 0.2065(3) 0.3689(3) 0.46619(13) 0.0846(8) Uani 1 1 d . . .
F1 F 0.9035(2) 0.24281(17) 0.83335(9) 0.0680(5) Uani 1 1 d . . .
F3 F 0.4837(3) -0.1029(2) 0.13601(9) 0.0770(6) Uani 1 1 d . . .
F2 F 0.9057(2) 0.0439(3) 0.27453(12) 0.1031(8) Uani 1 1 d . . .
N1 N 0.7260(3) 0.6687(2) 0.98558(10) 0.0363(5) Uani 1 1 d . . .
N2 N 0.8807(3) 0.5010(2) 0.75744(11) 0.0538(6) Uani 1 1 d . . .
N3 N 1.0545(3) 0.5022(3) 0.61545(11) 0.0553(7) Uani 1 1 d . . .
H3A H 1.1565 0.4799 0.5859 0.066 Uiso 1 1 calc R . .
H3B H 0.9682 0.5442 0.5886 0.066 Uiso 1 1 calc R . .
H2 H 0.658(6) 0.314(4) 1.170(2) 0.113(15) Uiso 1 1 d . . .
H6 H 0.572(6) 0.324(4) 0.5747(19) 0.097(12) Uiso 1 1 d . . .


_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
C9 C8 1.400(3) . ?
C9 N1 1.404(3) . ?
C9 C4 1.407(3) . ?
C8 C7 1.400(3) . ?
C4 C5 1.404(4) . ?
C4 C3 1.447(3) . ?
C5 C6 1.349(4) . ?
C6 F1 1.363(3) . ?
C6 C7 1.417(4) . ?
C3 O3 1.269(3) . ?
C3 C2 1.431(4) . ?
C2 C10 1.367(4) . ?
C2 C1 1.492(4) . ?
C7 N2 1.375(3) . ?
C10 N1 1.349(3) . ?
C15 N1 1.463(3) . ?
C15 C16 1.486(4) . ?
C15 C17 1.491(3) . ?
C23 C24 1.392(4) . ?
C23 C22 1.396(4) . ?
C23 C25 1.482(4) . ?
C19 C24 1.382(4) . ?
C19 C20 1.397(4) . ?
C19 C18 1.500(4) . ?
C25 C26 1.389(4) . ?
C25 C30 1.391(4) . ?
C29 C28 1.366(4) . ?
C29 C30 1.378(4) . ?
C18 O4 1.236(3) . ?
C18 O5 1.274(3) . ?
C14 N3 1.482(4) . ?
C14 C13 1.520(4) . ?
C20 O6 1.348(3) . ?
C20 C21 1.389(4) . ?
C22 C21 1.376(4) . ?
C13 N2 1.450(4) . ?
C11 N2 1.472(4) . ?
C11 C12 1.509(4) . ?
C1 O1 1.203(4) . ?
C1 O2 1.339(4) . ?
C12 N3 1.485(4) . ?
C28 C27 1.359(4) . ?
C28 F3 1.365(3) . ?
C16 C17 1.490(4) . ?
C26 F2 1.365(3) . ?
C26 C27 1.375(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
C8 C9 N1 121.3(2) . . ?
C8 C9 C4 120.5(2) . . ?
N1 C9 C4 118.2(2) . . ?
C7 C8 C9 121.5(2) . . ?
C5 C4 C9 118.0(2) . . ?
C5 C4 C3 120.0(2) . . ?
C9 C4 C3 121.9(2) . . ?
C6 C5 C4 120.5(3) . . ?
C5 C6 F1 118.0(3) . . ?
C5 C6 C7 123.5(2) . . ?
F1 C6 C7 118.5(2) . . ?
O3 C3 C2 122.6(2) . . ?
O3 C3 C4 121.5(3) . . ?
C2 C3 C4 115.9(2) . . ?
C10 C2 C3 119.7(2) . . ?
C10 C2 C1 117.8(3) . . ?
C3 C2 C1 122.4(3) . . ?
N2 C7 C8 123.0(2) . . ?
N2 C7 C6 121.0(2) . . ?
C8 C7 C6 115.9(2) . . ?
N1 C10 C2 124.2(2) . . ?
N1 C15 C16 118.9(2) . . ?
N1 C15 C17 119.6(2) . . ?
C16 C15 C17 60.08(18) . . ?
C24 C23 C22 116.8(3) . . ?
C24 C23 C25 119.6(2) . . ?
C22 C23 C25 123.6(3) . . ?
C24 C19 C20 118.6(2) . . ?
C24 C19 C18 120.2(2) . . ?
C20 C19 C18 121.2(3) . . ?
C26 C25 C30 114.7(3) . . ?
C26 C25 C23 124.0(3) . . ?
C30 C25 C23 121.3(2) . . ?
C28 C29 C30 118.4(3) . . ?
O4 C18 O5 123.9(3) . . ?
O4 C18 C19 119.4(3) . . ?
O5 C18 C19 116.7(3) . . ?
N3 C14 C13 112.3(2) . . ?
C19 C24 C23 123.2(2) . . ?
C29 C30 C25 122.9(3) . . ?
O6 C20 C21 118.9(3) . . ?
O6 C20 C19 121.8(3) . . ?
C21 C20 C19 119.3(3) . . ?
C21 C22 C23 121.2(3) . . ?
N2 C13 C14 108.7(2) . . ?
C22 C21 C20 120.9(3) . . ?
N2 C11 C12 109.3(2) . . ?
O1 C1 O2 121.3(3) . . ?
O1 C1 C2 123.6(3) . . ?
O2 C1 C2 115.1(3) . . ?
N3 C12 C11 109.6(3) . . ?
C27 C28 F3 118.5(3) . . ?
C27 C28 C29 122.2(3) . . ?
F3 C28 C29 119.3(3) . . ?
C15 C16 C17 60.14(18) . . ?
F2 C26 C27 117.1(3) . . ?
F2 C26 C25 118.6(3) . . ?
C27 C26 C25 124.2(3) . . ?
C16 C17 C15 59.78(17) . . ?
C28 C27 C26 117.5(3) . . ?
C10 N1 C9 119.9(2) . . ?
C10 N1 C15 118.9(2) . . ?
C9 N1 C15 120.76(19) . . ?
C7 N2 C13 122.8(2) . . ?
C7 N2 C11 123.1(2) . . ?
C13 N2 C11 112.2(2) . . ?
C14 N3 C12 112.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 986495'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CIP_INDP_H2O

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Ciprofloxacin indoprofen hydrate salt'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H35 F N4 O7'
_chemical_formula_weight         630.66

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

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

_cell_length_a                   10.325(4)
_cell_length_b                   12.615(5)
_cell_length_c                   12.916(5)
_cell_angle_alpha                71.510(7)
_cell_angle_beta                 74.334(7)
_cell_angle_gamma                70.672(7)
_cell_volume                     1479.7(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1951
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.75

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.857
_exptl_crystal_size_mid          0.564
_exptl_crystal_size_min          0.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16971
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0859
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.40
_reflns_number_total             5237
_reflns_number_gt                2866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0591P)²+0.2287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5237
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_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
C1 C 0.3480(3) -0.0548(3) 0.7805(3) 0.0385(9) Uani 1 1 d . . .
C2 C 0.4330(3) 0.0028(3) 0.8093(3) 0.0298(8) Uani 1 1 d . . .
C3 C 0.3717(3) 0.0799(3) 0.8794(2) 0.0283(7) Uani 1 1 d . . .
C4 C 0.4644(3) 0.1339(3) 0.8988(2) 0.0257(7) Uani 1 1 d . . .
C5 C 0.4139(3) 0.2112(3) 0.9674(2) 0.0291(8) Uani 1 1 d . . .
H5 H 0.3192 0.2319 0.9975 0.035 Uiso 1 1 calc R . .
C6 C 0.5030(3) 0.2556(3) 0.9893(2) 0.0323(8) Uani 1 1 d . . .
C7 C 0.6478(3) 0.2305(3) 0.9458(2) 0.0317(8) Uani 1 1 d . . .
C8 C 0.6979(3) 0.1541(3) 0.8779(2) 0.0297(8) Uani 1 1 d . . .
H8 H 0.7926 0.1347 0.8475 0.036 Uiso 1 1 calc R . .
C9 C 0.6079(3) 0.1053(3) 0.8543(2) 0.0264(7) Uani 1 1 d . . .
C10 C 0.5733(3) -0.0208(3) 0.7670(3) 0.0352(8) Uani 1 1 d . . .
H10 H 0.6105 -0.0725 0.7221 0.042 Uiso 1 1 calc R . .
C11 C 0.7001(3) 0.3973(3) 0.9710(3) 0.0425(9) Uani 1 1 d . . .
H11A H 0.5996 0.4272 0.9899 0.051 Uiso 1 1 calc R . .
H11B H 0.7307 0.4381 0.8953 0.051 Uiso 1 1 calc R . .
C12 C 0.7695(3) 0.4191(3) 1.0492(3) 0.0457(10) Uani 1 1 d . . .
H12A H 0.7482 0.5018 1.0415 0.055 Uiso 1 1 calc R . .
H12B H 0.7347 0.3828 1.1255 0.055 Uiso 1 1 calc R . .
C13 C 0.8864(3) 0.2241(3) 0.9500(3) 0.0407(9) Uani 1 1 d . . .
H13A H 0.9204 0.2607 0.8737 0.049 Uiso 1 1 calc R . .
H13B H 0.9073 0.1415 0.9573 0.049 Uiso 1 1 calc R . .
C14 C 0.9578(3) 0.2448(3) 1.0273(3) 0.0436(10) Uani 1 1 d . . .
H14A H 0.9286 0.2032 1.1029 0.052 Uiso 1 1 calc R . .
H14B H 1.0581 0.2150 1.0070 0.052 Uiso 1 1 calc R . .
C15 C 0.8115(3) -0.0172(3) 0.7490(3) 0.0424(9) Uani 1 1 d . . .
H15 H 0.8613 -0.0788 0.8043 0.051 Uiso 1 1 calc R . .
C16 C 0.8635(3) -0.0275(4) 0.6322(4) 0.0715(14) Uani 1 1 d . . .
H16A H 0.9398 -0.0944 0.6188 0.086 Uiso 1 1 calc R . .
H16B H 0.7958 -0.0006 0.5836 0.086 Uiso 1 1 calc R . .
C17 C 0.8941(3) 0.0611(3) 0.6689(3) 0.0408(9) Uani 1 1 d . . .
H17A H 0.9890 0.0480 0.6776 0.049 Uiso 1 1 calc R . .
H17B H 0.8451 0.1418 0.6424 0.049 Uiso 1 1 calc R . .
C18 C 0.0885(4) 0.3981(4) 0.2003(3) 0.0501(11) Uani 1 1 d . . .
C19 C 0.1384(3) 0.3474(3) 0.3126(3) 0.0417(9) Uani 1 1 d . . .
H19 H 0.1974 0.2681 0.3147 0.050 Uiso 1 1 calc R . .
C20 C 0.2255(3) 0.4178(3) 0.3256(2) 0.0327(8) Uani 1 1 d . . .
C21 C 0.1652(3) 0.5173(3) 0.3645(2) 0.0346(8) Uani 1 1 d . . .
H21 H 0.0685 0.5430 0.3823 0.042 Uiso 1 1 calc R . .
C22 C 0.2465(3) 0.5796(3) 0.3774(2) 0.0335(8) Uani 1 1 d . . .
H22 H 0.2037 0.6464 0.4028 0.040 Uiso 1 1 calc R . .
C23 C 0.3905(3) 0.5423(3) 0.3525(2) 0.0274(7) Uani 1 1 d . . .
C24 C 0.4517(3) 0.4436(3) 0.3121(2) 0.0330(8) Uani 1 1 d . . .
H24 H 0.5484 0.4183 0.2935 0.040 Uiso 1 1 calc R . .
C25 C 0.3702(3) 0.3829(3) 0.2994(3) 0.0386(9) Uani 1 1 d . . .
H25 H 0.4133 0.3170 0.2725 0.046 Uiso 1 1 calc R . .
C26 C 0.4368(3) 0.6817(3) 0.4300(2) 0.0308(8) Uani 1 1 d . . .
C27 C 0.5592(3) 0.7247(3) 0.4143(3) 0.0320(8) Uani 1 1 d . . .
C28 C 0.5707(3) 0.8075(3) 0.4583(3) 0.0440(9) Uani 1 1 d . . .
H28 H 0.4964 0.8442 0.5054 0.053 Uiso 1 1 calc R . .
C29 C 0.6996(4) 0.8329(3) 0.4282(3) 0.0509(10) Uani 1 1 d . . .
H29 H 0.7119 0.8881 0.4554 0.061 Uiso 1 1 calc R . .
C30 C 0.8084(4) 0.7775(3) 0.3589(3) 0.0490(10) Uani 1 1 d . . .
H30 H 0.8928 0.7967 0.3401 0.059 Uiso 1 1 calc R . .
C31 C 0.7969(3) 0.6950(3) 0.3167(3) 0.0406(9) Uani 1 1 d . . .
H31 H 0.8717 0.6580 0.2701 0.049 Uiso 1 1 calc R . .
C32 C 0.6692(3) 0.6686(3) 0.3461(2) 0.0313(8) Uani 1 1 d . . .
C33 C 0.6252(3) 0.5831(3) 0.3146(3) 0.0333(8) Uani 1 1 d . . .
H33A H 0.6367 0.5987 0.2346 0.040 Uiso 1 1 calc R . .
H33B H 0.6782 0.5043 0.3433 0.040 Uiso 1 1 calc R . .
C34 C 0.0109(3) 0.3412(3) 0.4038(3) 0.0466(10) Uani 1 1 d . . .
H34A H 0.0391 0.3129 0.4749 0.070 Uiso 1 1 calc R . .
H34B H -0.0342 0.2896 0.3958 0.070 Uiso 1 1 calc R . .
H34C H -0.0528 0.4172 0.3986 0.070 Uiso 1 1 calc R . .
F1 F 0.45153(16) 0.32428(18) 1.06190(15) 0.0502(6) Uani 1 1 d . . .
H35 H 0.240(4) 0.765(4) 0.623(3) 0.085(15) Uiso 1 1 d . . .
H35A H 0.256(4) 0.812(4) 0.706(3) 0.090(15) Uiso 1 1 d . . .
N1 N 0.6603(2) 0.0268(2) 0.7868(2) 0.0309(6) Uani 1 1 d . . .
N2 N 0.7354(2) 0.2727(3) 0.9785(2) 0.0360(7) Uani 1 1 d . . .
N3 N 0.9229(2) 0.3697(3) 1.0212(2) 0.0433(8) Uani 1 1 d . . .
H3A H 0.9555 0.4076 0.9522 0.052 Uiso 1 1 calc R . .
H3B H 0.9648 0.3798 1.0688 0.052 Uiso 1 1 calc R . .
N4 N 0.4766(2) 0.6020(2) 0.36741(19) 0.0272(6) Uani 1 1 d . . .
O1 O 0.3956(2) -0.1193(2) 0.7187(2) 0.0541(7) Uani 1 1 d . . .
O2 O 0.21293(19) -0.0287(2) 0.8253(2) 0.0422(6) Uani 1 1 d . . .
H2 H 0.1972 0.0165 0.8637 0.063 Uiso 1 1 calc R . .
O3 O 0.24279(18) 0.10130(18) 0.92417(17) 0.0337(5) Uani 1 1 d . . .
O4 O 0.1264(2) 0.3367(3) 0.1340(2) 0.0627(8) Uani 1 1 d . . .
O5 O 0.0085(3) 0.5007(3) 0.18398(19) 0.0559(8) Uani 1 1 d . . .
O6 O 0.3207(2) 0.7108(2) 0.48676(18) 0.0424(6) Uani 1 1 d . . .
O7 O 0.2001(3) 0.7804(3) 0.6896(3) 0.0663(9) Uani 1 1 d . . .


_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 O1 1.216(4) . ?
C1 O2 1.330(3) . ?
C1 C2 1.485(4) . ?
C2 C10 1.370(4) . ?
C2 C3 1.418(4) . ?
C3 O3 1.275(3) . ?
C3 C4 1.453(4) . ?
C4 C5 1.403(4) . ?
C4 C9 1.405(4) . ?
C5 C6 1.350(4) . ?
C6 F1 1.361(3) . ?
C6 C7 1.413(4) . ?
C7 C8 1.388(4) . ?
C7 N2 1.396(3) . ?
C8 C9 1.409(4) . ?
C9 N1 1.405(4) . ?
C10 N1 1.345(4) . ?
C11 N2 1.468(4) . ?
C11 C12 1.520(4) . ?
C12 N3 1.486(4) . ?
C13 N2 1.464(3) . ?
C13 C14 1.515(4) . ?
C14 N3 1.477(4) . ?
C15 N1 1.473(3) . ?
C15 C17 1.485(4) . ?
C15 C16 1.491(5) . ?
C16 C17 1.491(5) . ?
C18 O4 1.235(4) . ?
C18 O5 1.271(5) . ?
C18 C19 1.541(5) . ?
C19 C34 1.516(4) . ?
C19 C20 1.526(4) . ?
C20 C25 1.388(4) . ?
C20 C21 1.390(4) . ?
C21 C22 1.394(4) . ?
C22 C23 1.382(4) . ?
C23 C24 1.391(4) . ?
C23 N4 1.423(3) . ?
C24 C25 1.379(4) . ?
C26 O6 1.230(3) . ?
C26 N4 1.376(4) . ?
C26 C27 1.477(4) . ?
C27 C32 1.375(4) . ?
C27 C28 1.387(4) . ?
C28 C29 1.395(4) . ?
C29 C30 1.373(5) . ?
C30 C31 1.368(5) . ?
C31 C32 1.390(4) . ?
C32 C33 1.496(4) . ?
C33 N4 1.473(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
O1 C1 O2 121.3(3) . . ?
O1 C1 C2 123.5(3) . . ?
O2 C1 C2 115.2(3) . . ?
C10 C2 C3 120.2(3) . . ?
C10 C2 C1 118.5(3) . . ?
C3 C2 C1 121.3(3) . . ?
O3 C3 C2 122.6(3) . . ?
O3 C3 C4 121.0(3) . . ?
C2 C3 C4 116.3(2) . . ?
C5 C4 C9 118.4(2) . . ?
C5 C4 C3 120.7(2) . . ?
C9 C4 C3 120.9(3) . . ?
C6 C5 C4 119.8(3) . . ?
C5 C6 F1 118.0(2) . . ?
C5 C6 C7 124.0(3) . . ?
F1 C6 C7 117.9(2) . . ?
C8 C7 N2 122.7(3) . . ?
C8 C7 C6 116.2(3) . . ?
N2 C7 C6 120.8(3) . . ?
C7 C8 C9 121.2(3) . . ?
C4 C9 N1 119.0(2) . . ?
C4 C9 C8 120.4(3) . . ?
N1 C9 C8 120.6(2) . . ?
N1 C10 C2 123.7(3) . . ?
N2 C11 C12 110.7(3) . . ?
N3 C12 C11 108.7(2) . . ?
N2 C13 C14 109.2(2) . . ?
N3 C14 C13 111.0(3) . . ?
N1 C15 C17 120.9(3) . . ?
N1 C15 C16 118.8(3) . . ?
C17 C15 C16 60.1(2) . . ?
C17 C16 C15 59.7(2) . . ?
C15 C17 C16 60.1(2) . . ?
O4 C18 O5 124.9(4) . . ?
O4 C18 C19 118.5(4) . . ?
O5 C18 C19 116.6(3) . . ?
C34 C19 C20 113.2(3) . . ?
C34 C19 C18 108.0(3) . . ?
C20 C19 C18 111.2(3) . . ?
C25 C20 C21 117.3(3) . . ?
C25 C20 C19 120.4(3) . . ?
C21 C20 C19 122.3(3) . . ?
C20 C21 C22 121.5(3) . . ?
C23 C22 C21 120.2(3) . . ?
C22 C23 C24 118.7(3) . . ?
C22 C23 N4 121.7(3) . . ?
C24 C23 N4 119.6(3) . . ?
C25 C24 C23 120.5(3) . . ?
C24 C25 C20 121.7(3) . . ?
O6 C26 N4 125.9(3) . . ?
O6 C26 C27 127.5(3) . . ?
N4 C26 C27 106.6(2) . . ?
C32 C27 C28 122.1(3) . . ?
C32 C27 C26 109.3(3) . . ?
C28 C27 C26 128.6(3) . . ?
C27 C28 C29 116.5(3) . . ?
C30 C29 C28 121.0(3) . . ?
C31 C30 C29 122.2(3) . . ?
C30 C31 C32 117.5(3) . . ?
C27 C32 C31 120.7(3) . . ?
C27 C32 C33 109.4(2) . . ?
C31 C32 C33 130.0(3) . . ?
N4 C33 C32 103.0(2) . . ?
C10 N1 C9 119.8(2) . . ?
C10 N1 C15 118.4(3) . . ?
C9 N1 C15 121.3(2) . . ?
C7 N2 C13 118.1(3) . . ?
C7 N2 C11 119.2(3) . . ?
C13 N2 C11 111.3(2) . . ?
C14 N3 C12 111.0(2) . . ?
C26 N4 C23 126.6(2) . . ?
C26 N4 C33 111.6(2) . . ?
C23 N4 C33 121.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 986496'
