# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_SPX-MBZ
_database_code_depnum_ccdc_archive 'CCDC 1498301'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-Amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid-methyl 4-hydroxy benzoate
;
_chemical_name_common            'Sparfloxacin-methyl paraben cocrystal'
_chemical_melting_point          474K
_chemical_formula_moiety         'C19 H22 F2 N4 O3, C8 H8 O3'
_chemical_formula_sum            'C27 H30 F2 N4 O6'
_chemical_formula_weight         544.55

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.423(5)
_cell_length_b                   12.742(7)
_cell_length_c                   12.890(7)
_cell_angle_alpha                62.717(9)
_cell_angle_beta                 70.160(9)
_cell_angle_gamma                76.407(10)
_cell_volume                     1287.9(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1913
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      23.84

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12937
_diffrn_reflns_av_unetI/netI     0.1070
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_max         26.079
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4973
_reflns_number_gt                2756
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4973
_refine_ls_number_parameters     450
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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_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
O1 O 1.0167(2) -0.16952(16) 0.90648(17) 0.0269(5) Uani 1 1 d . . . . .
O3 O 1.4586(2) -0.13676(17) 0.86544(17) 0.0311(5) Uani 1 1 d . . . . .
O2 O 1.2839(2) -0.25404(17) 0.90977(17) 0.0294(5) Uani 1 1 d . . . . .
C8 C 1.2054(3) -0.0490(2) 0.8616(2) 0.0210(6) Uani 1 1 d . . . . .
N1 N 1.1443(2) 0.15971(19) 0.8025(2) 0.0221(5) Uani 1 1 d . . . . .
N2 N 0.7360(3) -0.0725(2) 0.8921(2) 0.0286(6) Uani 1 1 d . . . . .
N3 N 0.6273(2) 0.34166(19) 0.8163(2) 0.0252(6) Uani 1 1 d . . . . .
C6 C 0.9436(3) 0.0369(2) 0.8554(2) 0.0202(6) Uani 1 1 d . . . . .
C2 C 0.8816(3) 0.2452(2) 0.8202(2) 0.0207(6) Uani 1 1 d . . . . .
C7 C 1.0529(3) -0.0665(2) 0.8757(2) 0.0217(6) Uani 1 1 d . . . . .
C4 C 0.6935(3) 0.1344(2) 0.8439(2) 0.0227(7) Uani 1 1 d . . . . .
C1 C 0.9895(3) 0.1493(2) 0.8252(2) 0.0207(6) Uani 1 1 d . . . . .
C9 C 1.2433(3) 0.0620(2) 0.8240(2) 0.0218(6) Uani 1 1 d . . . . .
C5 C 0.7904(3) 0.0298(2) 0.8653(2) 0.0217(6) Uani 1 1 d . . . . .
C3 C 0.7306(3) 0.2427(2) 0.8257(2) 0.0216(6) Uani 1 1 d . . . . .
N4 N 0.4378(3) 0.5429(2) 0.8299(2) 0.0261(6) Uani 1 1 d . . . . .
C10 C 1.3278(3) -0.1488(2) 0.8790(2) 0.0242(7) Uani 1 1 d . . . . .
C17 C 0.6642(3) 0.4607(2) 0.7228(3) 0.0265(7) Uani 1 1 d . . . . .
C14 C 0.4656(3) 0.3323(3) 0.8768(3) 0.0271(7) Uani 1 1 d . . . . .
C16 C 0.6042(3) 0.5507(3) 0.7773(3) 0.0290(7) Uani 1 1 d . . . . .
C11 C 1.2038(3) 0.2766(3) 0.7410(3) 0.0258(7) Uani 1 1 d . . . . .
C13 C 1.1863(3) 0.3557(3) 0.6160(3) 0.0314(8) Uani 1 1 d . . . . .
C15 C 0.4032(3) 0.4237(3) 0.9295(3) 0.0262(7) Uani 1 1 d . . . . .
C18 C 0.2321(3) 0.4225(3) 0.9854(4) 0.0351(8) Uani 1 1 d . . . . .
C19 C 0.6341(3) 0.6769(3) 0.6835(3) 0.0399(9) Uani 1 1 d . . . . .
H19A H 0.5815 0.6993 0.6233 0.060 Uiso 1 1 calc R U . . .
H19B H 0.7409 0.6806 0.6455 0.060 Uiso 1 1 calc R U . . .
H19C H 0.5988 0.7302 0.7227 0.060 Uiso 1 1 calc R U . . .
C12 C 1.3401(3) 0.2976(3) 0.6339(3) 0.0322(8) Uani 1 1 d . . . . .
O5 O 0.7716(2) 0.95884(18) 0.59215(19) 0.0381(6) Uani 1 1 d . . . . .
O6 O 1.3387(2) 0.5778(2) 0.6410(2) 0.0421(6) Uani 1 1 d D . . . .
C26 C 1.0737(3) 0.7752(3) 0.4702(3) 0.0309(7) Uani 1 1 d . . . . .
C21 C 0.9787(3) 0.8276(2) 0.5472(3) 0.0295(7) Uani 1 1 d . . . . .
C25 C 1.1952(4) 0.6943(3) 0.5012(3) 0.0320(8) Uani 1 1 d . . . . .
C23 C 1.1303(3) 0.7154(3) 0.6892(3) 0.0389(9) Uani 1 1 d . . . . .
C24 C 1.2212(3) 0.6611(3) 0.6124(3) 0.0323(7) Uani 1 1 d . . . . .
C22 C 1.0108(4) 0.7973(3) 0.6567(3) 0.0366(8) Uani 1 1 d . . . . .
C20 C 0.8456(3) 0.9093(3) 0.5126(3) 0.0332(8) Uani 1 1 d . . . . .
O4 O 0.8044(2) 0.92807(19) 0.42623(19) 0.0426(6) Uani 1 1 d . . . . .
F1 F 0.91713(16) 0.34420(13) 0.81842(14) 0.0276(4) Uani 1 1 d . . . . .
F2 F 0.55211(16) 0.12709(14) 0.84096(14) 0.0310(4) Uani 1 1 d . . . . .
H9 H 1.345(3) 0.081(2) 0.810(2) 0.017(7) Uiso 1 1 d . . . . .
H12A H 1.377(3) 0.240(2) 0.612(2) 0.024(8) Uiso 1 1 d . . . . .
H11 H 1.190(3) 0.311(2) 0.796(2) 0.019(7) Uiso 1 1 d . . . . .
H13A H 1.140(3) 0.322(3) 0.584(3) 0.037(9) Uiso 1 1 d . . . . .
H12B H 1.411(3) 0.347(2) 0.625(2) 0.021(7) Uiso 1 1 d . . . . .
H2C H 0.803(3) -0.135(3) 0.896(3) 0.036(9) Uiso 1 1 d . . . . .
H17A H 0.775(3) 0.462(2) 0.686(2) 0.028(7) Uiso 1 1 d . . . . .
H18A H 0.182(4) 0.437(3) 0.925(4) 0.067(13) Uiso 1 1 d . . . . .
H18B H 0.193(3) 0.485(3) 1.011(2) 0.026(8) Uiso 1 1 d . . . . .
H25 H 1.254(3) 0.660(2) 0.455(2) 0.024(8) Uiso 1 1 d . . . . .
H15 H 0.454(3) 0.404(2) 0.991(3) 0.035(9) Uiso 1 1 d . . . . .
H22 H 0.942(3) 0.837(2) 0.712(3) 0.043(9) Uiso 1 1 d . . . . .
H17B H 0.617(3) 0.483(2) 0.653(2) 0.025(7) Uiso 1 1 d . . . . .
H2B H 0.652(3) -0.072(2) 0.882(3) 0.029(9) Uiso 1 1 d . . . . .
H14A H 0.447(3) 0.254(3) 0.943(3) 0.028(8) Uiso 1 1 d . . . . .
H16 H 0.661(3) 0.525(2) 0.842(2) 0.030(8) Uiso 1 1 d . . . . .
H4A H 0.404(3) 0.594(2) 0.856(2) 0.019(8) Uiso 1 1 d . . . . .
H2A H 1.170(5) -0.243(3) 0.915(3) 0.085(13) Uiso 1 1 d . . . . .
H14B H 0.405(3) 0.353(2) 0.817(3) 0.029(8) Uiso 1 1 d . . . . .
H13B H 1.164(3) 0.440(3) 0.594(3) 0.044(9) Uiso 1 1 d . . . . .
H18C H 0.215(3) 0.349(3) 1.055(3) 0.040(9) Uiso 1 1 d . . . . .
H6A H 1.359(5) 0.568(4) 0.707(3) 0.107(18) Uiso 1 1 d D . . . .
H26 H 1.051(3) 0.799(3) 0.396(3) 0.040(9) Uiso 1 1 d . . . . .
H23 H 1.146(3) 0.692(3) 0.769(3) 0.052(10) Uiso 1 1 d . . . . .
C27 C 0.6361(4) 1.0346(3) 0.5694(3) 0.0484(10) Uani 1 1 d . . . . .
H27A H 0.6565 1.0899 0.4858 0.073 Uiso 1 1 calc R U . . .
H27B H 0.6033 1.0773 0.6198 0.073 Uiso 1 1 calc R U . . .
H27C H 0.5581 0.9874 0.5873 0.073 Uiso 1 1 calc R U . . .


_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 C7 1.280(3) . ?
O3 C10 1.221(3) . ?
O2 C10 1.338(3) . ?
C8 C9 1.362(4) . ?
C8 C7 1.443(4) . ?
C8 C10 1.490(4) . ?
N1 C9 1.345(3) . ?
N1 C1 1.413(3) . ?
N1 C11 1.473(3) . ?
N2 C5 1.364(4) . ?
N3 C3 1.383(3) . ?
N3 C14 1.462(3) . ?
N3 C17 1.470(3) . ?
C6 C5 1.426(4) . ?
C6 C1 1.434(4) . ?
C6 C7 1.446(4) . ?
C2 F1 1.368(3) . ?
C2 C1 1.386(4) . ?
C2 C3 1.407(4) . ?
C4 F2 1.371(3) . ?
C4 C5 1.396(4) . ?
C4 C3 1.399(4) . ?
N4 C16 1.490(4) . ?
N4 C15 1.490(4) . ?
C17 C16 1.515(4) . ?
C14 C15 1.515(4) . ?
C16 C19 1.526(4) . ?
C11 C12 1.498(4) . ?
C11 C13 1.500(4) . ?
C13 C12 1.506(4) . ?
C15 C18 1.527(4) . ?
O5 C20 1.355(4) . ?
O5 C27 1.436(4) . ?
O6 C24 1.361(4) . ?
C26 C25 1.383(4) . ?
C26 C21 1.398(4) . ?
C21 C22 1.403(4) . ?
C21 C20 1.482(4) . ?
C25 C24 1.389(4) . ?
C23 C22 1.378(4) . ?
C23 C24 1.402(4) . ?
C20 O4 1.206(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
C9 C8 C7 120.1(2) . . ?
C9 C8 C10 118.0(2) . . ?
C7 C8 C10 121.8(2) . . ?
C9 N1 C1 119.8(2) . . ?
C9 N1 C11 118.5(2) . . ?
C1 N1 C11 121.2(2) . . ?
C3 N3 C14 122.2(2) . . ?
C3 N3 C17 122.0(2) . . ?
C14 N3 C17 114.1(2) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 121.6(2) . . ?
C1 C6 C7 119.5(2) . . ?
F1 C2 C1 120.0(2) . . ?
F1 C2 C3 117.3(2) . . ?
C1 C2 C3 122.6(3) . . ?
O1 C7 C8 121.0(2) . . ?
O1 C7 C6 122.0(2) . . ?
C8 C7 C6 117.0(2) . . ?
F2 C4 C5 115.7(2) . . ?
F2 C4 C3 119.3(2) . . ?
C5 C4 C3 125.0(3) . . ?
C2 C1 N1 121.2(2) . . ?
C2 C1 C6 119.6(2) . . ?
N1 C1 C6 119.2(2) . . ?
N1 C9 C8 123.8(3) . . ?
N2 C5 C4 119.2(3) . . ?
N2 C5 C6 123.4(3) . . ?
C4 C5 C6 117.4(3) . . ?
N3 C3 C4 123.5(2) . . ?
N3 C3 C2 120.9(2) . . ?
C4 C3 C2 115.7(2) . . ?
C16 N4 C15 111.4(2) . . ?
O3 C10 O2 121.9(3) . . ?
O3 C10 C8 123.5(3) . . ?
O2 C10 C8 114.6(2) . . ?
N3 C17 C16 109.9(2) . . ?
N3 C14 C15 110.0(2) . . ?
N4 C16 C17 107.0(2) . . ?
N4 C16 C19 109.5(2) . . ?
C17 C16 C19 112.4(3) . . ?
N1 C11 C12 118.4(3) . . ?
N1 C11 C13 117.8(3) . . ?
C12 C11 C13 60.3(2) . . ?
C11 C13 C12 59.8(2) . . ?
N4 C15 C14 108.1(2) . . ?
N4 C15 C18 109.4(2) . . ?
C14 C15 C18 111.4(3) . . ?
C11 C12 C13 59.9(2) . . ?
C20 O5 C27 115.7(3) . . ?
C25 C26 C21 121.3(3) . . ?
C26 C21 C22 118.3(3) . . ?
C26 C21 C20 119.2(3) . . ?
C22 C21 C20 122.5(3) . . ?
C26 C25 C24 119.7(3) . . ?
C22 C23 C24 119.9(3) . . ?
O6 C24 C25 117.6(3) . . ?
O6 C24 C23 122.5(3) . . ?
C25 C24 C23 119.9(3) . . ?
C23 C22 C21 120.9(3) . . ?
O4 C20 O5 123.3(3) . . ?
O4 C20 C21 124.7(3) . . ?
O5 C20 C21 111.9(3) . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_SPX-PBZ
_database_code_depnum_ccdc_archive 'CCDC 1498302'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-Amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid-4-hydroxy-propylbenzoate 
;
_chemical_name_common            'Sparfloxacin-Propylparaben cocrystal'
_chemical_melting_point          405K
_chemical_formula_moiety         'C19 H22 F2 N4 O3, C10 H10 O3'
_chemical_formula_sum            'C29 H34 F2 N4 O6'
_chemical_formula_weight         572.60

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9588(4)
_cell_length_b                   10.3333(5)
_cell_length_c                   17.8484(9)
_cell_angle_alpha                80.749(4)
_cell_angle_beta                 87.489(4)
_cell_angle_gamma                72.019(5)
_cell_volume                     1377.99(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4973
_cell_measurement_theta_min      2.9210
_cell_measurement_theta_max      29.7400

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20756
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.691
_diffrn_reflns_theta_max         30.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7354
_reflns_number_gt                4637
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7354
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.2210
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
F1 F 0.1913(2) 0.20471(15) 0.45878(9) 0.0293(4) Uani 1 1 d . . . . .
F2 F 0.1702(2) 0.57659(15) 0.26528(8) 0.0263(4) Uani 1 1 d . . . . .
O1 O 0.3144(3) 0.73728(18) 0.50083(11) 0.0261(5) Uani 1 1 d . . . . .
O2 O 0.3830(2) 0.74369(18) 0.63712(11) 0.0266(5) Uani 1 1 d . . . . .
H2A H 0.3572 0.7689 0.5920 0.040 Uiso 1 1 d R U . . .
O3 O 0.3826(2) 0.56573(19) 0.72542(10) 0.0253(4) Uani 1 1 d . . . . .
N1 N 0.2555(3) 0.3540(2) 0.57006(12) 0.0196(5) Uani 1 1 d . . . . .
N2 N 0.2441(3) 0.7253(2) 0.35946(13) 0.0256(5) Uani 1 1 d . . . . .
H2B H 0.2685 0.7750 0.3896 0.031 Uiso 1 1 d R U . . .
H2C H 0.2594 0.7310 0.3111 0.031 Uiso 1 1 d R U . . .
N3 N 0.1910(3) 0.2980(2) 0.30783(12) 0.0220(5) Uani 1 1 d . . . . .
N4 N 0.2126(3) 0.1057(2) 0.20715(13) 0.0231(5) Uani 1 1 d . . . . .
H4A H 0.1286 0.1551 0.1740 0.028 Uiso 1 1 d R U . . .
C1 C 0.2336(3) 0.4082(3) 0.49224(14) 0.0187(5) Uani 1 1 d . . . . .
C2 C 0.2022(3) 0.3347(3) 0.43842(15) 0.0205(6) Uani 1 1 d . . . . .
C3 C 0.1928(3) 0.3834(3) 0.36053(15) 0.0206(6) Uani 1 1 d . . . . .
C4 C 0.1995(3) 0.5172(3) 0.33912(14) 0.0211(6) Uani 1 1 d . . . . .
C5 C 0.2338(3) 0.5974(3) 0.38809(15) 0.0200(5) Uani 1 1 d . . . . .
C6 C 0.2522(3) 0.5421(2) 0.46708(14) 0.0190(5) Uani 1 1 d . . . . .
C7 C 0.2931(3) 0.6196(3) 0.52078(15) 0.0198(5) Uani 1 1 d . . . . .
C8 C 0.3130(3) 0.5556(3) 0.59871(15) 0.0204(5) Uani 1 1 d . . . . .
C9 C 0.2914(3) 0.4287(3) 0.61905(15) 0.0200(5) Uani 1 1 d . . . . .
H9 H 0.3023 0.3911 0.6702 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3625(3) 0.6205(3) 0.65920(15) 0.0215(6) Uani 1 1 d . . . . .
C11 C 0.2454(4) 0.2160(3) 0.60090(14) 0.0204(6) Uani 1 1 d . . . . .
H11 H 0.1277 0.2046 0.6002 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3958(4) 0.0924(3) 0.59006(16) 0.0272(6) Uani 1 1 d . . . . .
H12A H 0.4984 0.1071 0.5630 0.033 Uiso 1 1 calc R U . . .
H12B H 0.3686 0.0105 0.5818 0.033 Uiso 1 1 calc R U . . .
C13 C 0.3600(4) 0.1350(3) 0.66713(15) 0.0231(6) Uani 1 1 d . . . . .
H13A H 0.3109 0.0789 0.7053 0.028 Uiso 1 1 calc R U . . .
H13B H 0.4407 0.1755 0.6865 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2768(3) 0.3140(3) 0.23432(14) 0.0217(6) Uani 1 1 d . . . . .
H14A H 0.3714 0.3533 0.2384 0.026 Uiso 1 1 calc R U . . .
H14B H 0.1919 0.3755 0.1971 0.026 Uiso 1 1 calc R U . . .
C15 C 0.3502(3) 0.1740(3) 0.20969(15) 0.0229(6) Uani 1 1 d . . . . .
H15 H 0.4394 0.1161 0.2472 0.027 Uiso 1 1 calc R U . . .
C16 C 0.1168(3) 0.0970(3) 0.27982(15) 0.0215(6) Uani 1 1 d . . . . .
H16 H 0.1981 0.0327 0.3184 0.026 Uiso 1 1 calc R U . . .
C17 C 0.0482(3) 0.2365(3) 0.30680(15) 0.0234(6) Uani 1 1 d . . . . .
H17A H -0.0456 0.2974 0.2732 0.028 Uiso 1 1 calc R U . . .
H17B H -0.0003 0.2252 0.3574 0.028 Uiso 1 1 calc R U . . .
C18 C 0.4401(4) 0.1831(3) 0.13329(16) 0.0299(7) Uani 1 1 d . . . . .
H18A H 0.4871 0.0926 0.1198 0.045 Uiso 1 1 calc R U . . .
H18B H 0.5343 0.2220 0.1361 0.045 Uiso 1 1 calc R U . . .
H18C H 0.3558 0.2406 0.0955 0.045 Uiso 1 1 calc R U . . .
C19 C -0.0369(4) 0.0418(3) 0.27054(17) 0.0286(7) Uani 1 1 d . . . . .
H19A H -0.1184 0.1045 0.2333 0.043 Uiso 1 1 calc R U . . .
H19B H -0.0962 0.0330 0.3182 0.043 Uiso 1 1 calc R U . . .
H19C H 0.0071 -0.0466 0.2543 0.043 Uiso 1 1 calc R U . . .
O4 O 0.9055(3) 0.2898(2) 0.10589(11) 0.0326(5) Uani 1 1 d . . . . .
O5 O 0.7846(2) 0.49991(18) 0.03780(10) 0.0246(4) Uani 1 1 d . . . . .
O6 O 0.6427(2) 0.15580(18) -0.19742(10) 0.0250(4) Uani 1 1 d . . . . .
H6A H 0.6874 0.0720 -0.1927 0.037 Uiso 1 1 d R U . . .
C20 C 0.8242(3) 0.3626(3) 0.04986(15) 0.0236(6) Uani 1 1 d . . . . .
C21 C 0.7644(3) 0.3089(3) -0.01241(15) 0.0225(6) Uani 1 1 d . . . . .
C22 C 0.8092(4) 0.1674(3) -0.01114(15) 0.0238(6) Uani 1 1 d . . . . .
H22 H 0.8688 0.1081 0.0308 0.029 Uiso 1 1 calc R U . . .
C23 C 0.7667(4) 0.1133(3) -0.07138(15) 0.0242(6) Uani 1 1 d . . . . .
H23 H 0.7965 0.0184 -0.0694 0.029 Uiso 1 1 calc R U . . .
C24 C 0.6790(3) 0.2016(3) -0.13488(14) 0.0208(6) Uani 1 1 d . . . . .
C25 C 0.6241(3) 0.3435(3) -0.13453(14) 0.0211(6) Uani 1 1 d . . . . .
H25 H 0.5578 0.4026 -0.1749 0.025 Uiso 1 1 calc R U . . .
C26 C 0.6675(3) 0.3964(3) -0.07474(14) 0.0197(5) Uani 1 1 d . . . . .
H26 H 0.6322 0.4913 -0.0756 0.024 Uiso 1 1 calc R U . . .
C27 C 0.8388(4) 0.5612(3) 0.09688(15) 0.0262(6) Uani 1 1 d . . . . .
H27A H 0.9659 0.5256 0.1039 0.031 Uiso 1 1 calc R U . . .
H27B H 0.7833 0.5386 0.1446 0.031 Uiso 1 1 calc R U . . .
C28 C 0.7835(4) 0.7149(3) 0.07294(16) 0.0255(6) Uani 1 1 d . . . . .
H28A H 0.6580 0.7485 0.0615 0.031 Uiso 1 1 calc R U . . .
H28B H 0.8462 0.7370 0.0272 0.031 Uiso 1 1 calc R U . . .
C29 C 0.8231(4) 0.7860(3) 0.13552(17) 0.0336(7) Uani 1 1 d . . . . .
H29A H 0.7890 0.8836 0.1188 0.050 Uiso 1 1 calc R U . . .
H29B H 0.9472 0.7525 0.1469 0.050 Uiso 1 1 calc R U . . .
H29C H 0.7579 0.7666 0.1802 0.050 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.363(3) . ?
F2 C4 1.359(3) . ?
O1 C7 1.271(3) . ?
O2 C10 1.327(3) . ?
O2 H2A 0.8200 . ?
O3 C10 1.220(3) . ?
N1 C9 1.347(3) . ?
N1 C1 1.409(3) . ?
N1 C11 1.470(3) . ?
N2 C5 1.364(3) . ?
N2 H2B 0.8661 . ?
N2 H2C 0.8606 . ?
N3 C3 1.393(3) . ?
N3 C14 1.461(3) . ?
N3 C17 1.466(3) . ?
N4 C15 1.480(3) . ?
N4 C16 1.480(3) . ?
N4 H4A 0.8859 . ?
C1 C2 1.391(3) . ?
C1 C6 1.434(3) . ?
C2 C3 1.397(4) . ?
C3 C4 1.391(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.429(3) . ?
C6 C7 1.450(3) . ?
C7 C8 1.434(4) . ?
C8 C9 1.365(3) . ?
C8 C10 1.485(3) . ?
C9 H9 0.9300 . ?
C11 C12 1.489(4) . ?
C11 C13 1.495(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.500(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.512(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C18 1.515(4) . ?
C15 H15 0.9800 . ?
C16 C17 1.524(4) . ?
C16 C19 1.526(3) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O4 C20 1.224(3) . ?
O5 C20 1.338(3) . ?
O5 C27 1.457(3) . ?
O6 C24 1.355(3) . ?
O6 H6A 0.8200 . ?
C20 C21 1.476(4) . ?
C21 C22 1.390(4) . ?
C21 C26 1.404(3) . ?
C22 C23 1.388(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.396(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.395(4) . ?
C25 C26 1.376(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.506(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.524(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

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
C10 O2 H2A 109.6 . . ?
C9 N1 C1 119.8(2) . . ?
C9 N1 C11 117.5(2) . . ?
C1 N1 C11 122.7(2) . . ?
C5 N2 H2B 119.4 . . ?
C5 N2 H2C 109.2 . . ?
H2B N2 H2C 127.9 . . ?
C3 N3 C14 120.3(2) . . ?
C3 N3 C17 121.0(2) . . ?
C14 N3 C17 113.4(2) . . ?
C15 N4 C16 112.3(2) . . ?
C15 N4 H4A 110.8 . . ?
C16 N4 H4A 103.6 . . ?
C2 C1 N1 122.6(2) . . ?
C2 C1 C6 118.7(2) . . ?
N1 C1 C6 118.7(2) . . ?
F1 C2 C1 121.1(2) . . ?
F1 C2 C3 115.6(2) . . ?
C1 C2 C3 123.1(2) . . ?
C4 C3 N3 122.4(2) . . ?
C4 C3 C2 116.2(2) . . ?
N3 C3 C2 121.2(2) . . ?
F2 C4 C5 116.1(2) . . ?
F2 C4 C3 119.1(2) . . ?
C5 C4 C3 124.7(2) . . ?
N2 C5 C4 119.1(2) . . ?
N2 C5 C6 123.3(2) . . ?
C4 C5 C6 117.6(2) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 120.1(2) . . ?
C1 C6 C7 120.5(2) . . ?
O1 C7 C8 120.7(2) . . ?
O1 C7 C6 122.7(2) . . ?
C8 C7 C6 116.6(2) . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 C10 117.7(2) . . ?
C7 C8 C10 122.4(2) . . ?
N1 C9 C8 124.5(2) . . ?
N1 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
O3 C10 O2 121.4(2) . . ?
O3 C10 C8 122.8(2) . . ?
O2 C10 C8 115.9(2) . . ?
N1 C11 C12 119.7(2) . . ?
N1 C11 C13 118.9(2) . . ?
C12 C11 C13 60.36(18) . . ?
N1 C11 H11 115.6 . . ?
C12 C11 H11 115.6 . . ?
C13 C11 H11 115.6 . . ?
C11 C12 C13 60.00(18) . . ?
C11 C12 H12A 117.8 . . ?
C13 C12 H12A 117.8 . . ?
C11 C12 H12B 117.8 . . ?
C13 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C11 C13 C12 59.64(17) . . ?
C11 C13 H13A 117.8 . . ?
C12 C13 H13A 117.8 . . ?
C11 C13 H13B 117.8 . . ?
C12 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
N3 C14 C15 108.7(2) . . ?
N3 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
N3 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
N4 C15 C14 112.1(2) . . ?
N4 C15 C18 109.7(2) . . ?
C14 C15 C18 111.6(2) . . ?
N4 C15 H15 107.8 . . ?
C14 C15 H15 107.8 . . ?
C18 C15 H15 107.8 . . ?
N4 C16 C17 111.7(2) . . ?
N4 C16 C19 109.6(2) . . ?
C17 C16 C19 109.8(2) . . ?
N4 C16 H16 108.6 . . ?
C17 C16 H16 108.6 . . ?
C19 C16 H16 108.6 . . ?
N3 C17 C16 110.4(2) . . ?
N3 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N3 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O5 C27 116.3(2) . . ?
C24 O6 H6A 109.4 . . ?
O4 C20 O5 123.2(2) . . ?
O4 C20 C21 123.9(2) . . ?
O5 C20 C21 112.9(2) . . ?
C22 C21 C26 118.4(2) . . ?
C22 C21 C20 119.5(2) . . ?
C26 C21 C20 122.0(2) . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
O6 C24 C25 117.9(2) . . ?
O6 C24 C23 122.9(2) . . ?
C25 C24 C23 119.3(2) . . ?
C26 C25 C24 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
O5 C27 C28 108.3(2) . . ?
O5 C27 H27A 110.0 . . ?
C28 C27 H27A 110.0 . . ?
O5 C27 H27B 110.0 . . ?
C28 C27 H27B 110.0 . . ?
H27A C27 H27B 108.4 . . ?
C27 C28 C29 110.7(2) . . ?
C27 C28 H28A 109.5 . . ?
C29 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 177.8(2) . . . . ?
C11 N1 C1 C2 -0.6(4) . . . . ?
C9 N1 C1 C6 0.7(4) . . . . ?
C11 N1 C1 C6 -177.8(2) . . . . ?
N1 C1 C2 F1 -0.1(4) . . . . ?
C6 C1 C2 F1 177.1(2) . . . . ?
N1 C1 C2 C3 -175.3(2) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
C14 N3 C3 C4 29.2(4) . . . . ?
C17 N3 C3 C4 -123.3(3) . . . . ?
C14 N3 C3 C2 -145.6(3) . . . . ?
C17 N3 C3 C2 61.9(3) . . . . ?
F1 C2 C3 C4 178.5(2) . . . . ?
C1 C2 C3 C4 -6.0(4) . . . . ?
F1 C2 C3 N3 -6.4(4) . . . . ?
C1 C2 C3 N3 169.0(2) . . . . ?
N3 C3 C4 F2 12.7(4) . . . . ?
C2 C3 C4 F2 -172.3(2) . . . . ?
N3 C3 C4 C5 -167.6(3) . . . . ?
C2 C3 C4 C5 7.4(4) . . . . ?
F2 C4 C5 N2 -3.0(4) . . . . ?
C3 C4 C5 N2 177.3(3) . . . . ?
F2 C4 C5 C6 175.4(2) . . . . ?
C3 C4 C5 C6 -4.3(4) . . . . ?
N2 C5 C6 C1 178.0(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
N2 C5 C6 C7 -3.4(4) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
N1 C1 C6 C5 178.8(2) . . . . ?
C2 C1 C6 C7 -177.1(2) . . . . ?
N1 C1 C6 C7 0.1(4) . . . . ?
C5 C6 C7 O1 -0.1(4) . . . . ?
C1 C6 C7 O1 178.5(2) . . . . ?
C5 C6 C7 C8 -178.7(2) . . . . ?
C1 C6 C7 C8 -0.1(4) . . . . ?
O1 C7 C8 C9 -179.3(2) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
O1 C7 C8 C10 -1.3(4) . . . . ?
C6 C7 C8 C10 177.3(2) . . . . ?
C1 N1 C9 C8 -1.6(4) . . . . ?
C11 N1 C9 C8 176.9(2) . . . . ?
C7 C8 C9 N1 1.6(4) . . . . ?
C10 C8 C9 N1 -176.5(2) . . . . ?
C9 C8 C10 O3 -0.7(4) . . . . ?
C7 C8 C10 O3 -178.7(3) . . . . ?
C9 C8 C10 O2 179.7(2) . . . . ?
C7 C8 C10 O2 1.7(4) . . . . ?
C9 N1 C11 C12 -102.7(3) . . . . ?
C1 N1 C11 C12 75.7(3) . . . . ?
C9 N1 C11 C13 -32.3(4) . . . . ?
C1 N1 C11 C13 146.2(3) . . . . ?
N1 C11 C12 C13 108.4(3) . . . . ?
N1 C11 C13 C12 -109.7(3) . . . . ?
C3 N3 C14 C15 147.1(2) . . . . ?
C17 N3 C14 C15 -58.5(3) . . . . ?
C16 N4 C15 C14 -54.0(3) . . . . ?
C16 N4 C15 C18 -178.5(2) . . . . ?
N3 C14 C15 N4 56.0(3) . . . . ?
N3 C14 C15 C18 179.6(2) . . . . ?
C15 N4 C16 C17 51.3(3) . . . . ?
C15 N4 C16 C19 173.2(2) . . . . ?
C3 N3 C17 C16 -148.8(2) . . . . ?
C14 N3 C17 C16 57.0(3) . . . . ?
N4 C16 C17 N3 -51.9(3) . . . . ?
C19 C16 C17 N3 -173.7(2) . . . . ?
C27 O5 C20 O4 -1.9(4) . . . . ?
C27 O5 C20 C21 179.8(2) . . . . ?
O4 C20 C21 C22 -3.8(4) . . . . ?
O5 C20 C21 C22 174.5(2) . . . . ?
O4 C20 C21 C26 178.3(3) . . . . ?
O5 C20 C21 C26 -3.4(4) . . . . ?
C26 C21 C22 C23 2.9(4) . . . . ?
C20 C21 C22 C23 -175.1(3) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 O6 176.1(2) . . . . ?
C22 C23 C24 C25 -4.6(4) . . . . ?
O6 C24 C25 C26 -175.7(2) . . . . ?
C23 C24 C25 C26 4.9(4) . . . . ?
C24 C25 C26 C21 -1.3(4) . . . . ?
C22 C21 C26 C25 -2.6(4) . . . . ?
C20 C21 C26 C25 175.4(2) . . . . ?
C20 O5 C27 C28 179.8(2) . . . . ?
O5 C27 C28 C29 175.3(2) . . . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_SPX-EBZ
_database_code_depnum_ccdc_archive 'CCDC 1498303'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-Amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid-ethyl 4-hydroxy benzoate
;
_chemical_name_common            'Sparfloxacin-ethyl paraben cocrystal'
_chemical_melting_point          427K
_chemical_formula_moiety         'C19 H22 F2 N4 O3, C9 H8 O3'
_chemical_formula_sum            'C28 H32 F2 N4 O6'
_chemical_formula_weight         558.57

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5457(5)
_cell_length_b                   12.8769(6)
_cell_length_c                   13.3380(7)
_cell_angle_alpha                62.8916(14)
_cell_angle_beta                 71.3599(16)
_cell_angle_gamma                77.1301(16)
_cell_volume                     1377.05(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.83

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68692
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.261
_diffrn_reflns_theta_max         27.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6368
_reflns_number_gt                4567
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0910P)²+0.2997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6368
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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_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
F1 F 0.91132(12) 0.82995(9) 0.34182(10) 0.0468(3) Uani 1 1 d . . . . .
F2 F 0.54973(11) 0.62568(10) 0.35276(12) 0.0539(3) Uani 1 1 d . . . . .
O1 O 1.01017(16) 0.33672(11) 0.38775(14) 0.0536(4) Uani 1 1 d . . . . .
N1 N 1.13188(15) 0.65192(12) 0.31872(13) 0.0353(3) Uani 1 1 d . . . . .
O3 O 1.43847(16) 0.36099(13) 0.36783(14) 0.0584(4) Uani 1 1 d . . . . .
C1 C 0.98151(18) 0.64236(14) 0.33798(14) 0.0312(3) Uani 1 1 d . . . . .
C6 C 0.93598(18) 0.53522(14) 0.35873(14) 0.0323(4) Uani 1 1 d . . . . .
C8 C 1.19212(19) 0.44884(15) 0.36221(15) 0.0362(4) Uani 1 1 d . . . . .
N3 N 0.62945(16) 0.83357(12) 0.33720(14) 0.0404(4) Uani 1 1 d . . . . .
N4 N 0.44316(17) 1.03534(13) 0.33597(14) 0.0411(4) Uani 1 1 d . . . . .
H4A H 0.403(2) 1.0942(19) 0.3591(18) 0.049 Uiso 1 1 d . U . . .
C3 C 0.72746(18) 0.73537(14) 0.34220(15) 0.0332(4) Uani 1 1 d . . . . .
C7 C 1.04415(19) 0.43450(14) 0.36979(15) 0.0357(4) Uani 1 1 d . . . . .
O2 O 1.27255(17) 0.25182(12) 0.39042(15) 0.0607(4) Uani 1 1 d . . . . .
H2A H 1.1815 0.2593 0.3944 0.091 Uiso 1 1 calc R U . . .
N2 N 0.7324(2) 0.43174(15) 0.38569(19) 0.0543(5) Uani 1 1 d . . . . .
C5 C 0.78476(19) 0.52985(14) 0.36790(15) 0.0358(4) Uani 1 1 d . . . . .
C2 C 0.87531(19) 0.73583(14) 0.33814(15) 0.0342(4) Uani 1 1 d . . . . .
C4 C 0.68946(18) 0.63148(15) 0.35426(16) 0.0366(4) Uani 1 1 d . . . . .
O5 O 0.18530(17) 0.56648(14) 0.95076(15) 0.0639(4) Uani 1 1 d . . . . .
C9 C 1.22894(19) 0.55618(15) 0.33454(15) 0.0375(4) Uani 1 1 d . . . . .
H9 H 1.3293 0.5641 0.3258 0.045 Uiso 1 1 calc R U . . .
C15 C 0.4088(2) 0.92120(16) 0.43378(16) 0.0402(4) Uani 1 1 d . . . . .
H15 H 0.4572 0.9084 0.4953 0.048 Uiso 1 1 calc R U . . .
C10 C 1.3125(2) 0.35163(16) 0.37359(16) 0.0442(4) Uani 1 1 d . . . . .
O6 O -0.3553(2) 0.94387(16) 0.84516(17) 0.0773(6) Uani 1 1 d . . . . .
H6A H -0.3655 0.9423 0.7857 0.116 Uiso 1 1 calc R U . . .
C14 C 0.47059(19) 0.82569(15) 0.39026(17) 0.0400(4) Uani 1 1 d . . . . .
H14A H 0.4532 0.7479 0.4560 0.048 Uiso 1 1 calc R U . . .
H14B H 0.4195 0.8350 0.3323 0.048 Uiso 1 1 calc R U . . .
O4 O 0.1391(2) 0.61574(17) 1.09847(15) 0.0800(6) Uani 1 1 d . . . . .
C17 C 0.6662(2) 0.94798(15) 0.24312(17) 0.0423(4) Uani 1 1 d . . . . .
H17A H 0.6236 0.9633 0.1785 0.051 Uiso 1 1 calc R U . . .
H17B H 0.7753 0.9487 0.2131 0.051 Uiso 1 1 calc R U . . .
C16 C 0.6045(2) 1.04273(16) 0.28745(18) 0.0448(4) Uani 1 1 d . . . . .
H16 H 0.6511 1.0282 0.3505 0.054 Uiso 1 1 calc R U . . .
C11 C 1.1905(2) 0.76632(16) 0.26351(19) 0.0448(5) Uani 1 1 d . . . . .
H11 H 1.1870 0.8022 0.3169 0.054 Uiso 1 1 calc R U . . .
C21 C -0.0136(2) 0.70556(17) 0.96632(17) 0.0449(4) Uani 1 1 d . . . . .
C24 C -0.2433(3) 0.86466(18) 0.88192(19) 0.0524(5) Uani 1 1 d . . . . .
C25 C -0.1464(3) 0.8075(2) 0.8173(2) 0.0625(6) Uani 1 1 d . . . . .
H25 H -0.1582 0.8228 0.7435 0.075 Uiso 1 1 calc R U . . .
C20 C 0.1079(2) 0.62552(19) 1.01387(18) 0.0503(5) Uani 1 1 d . . . . .
C13 C 1.3178(2) 0.7914(2) 0.1597(2) 0.0617(6) Uani 1 1 d . . . . .
H13A H 1.3588 0.7292 0.1312 0.074 Uiso 1 1 calc R U . . .
H13B H 1.3920 0.8402 0.1500 0.074 Uiso 1 1 calc R U . . .
C23 C -0.2264(2) 0.84115(19) 0.98958(19) 0.0536(5) Uani 1 1 d . . . . .
H23 H -0.2937 0.8790 1.0353 0.064 Uiso 1 1 calc R U . . .
C22 C -0.1122(2) 0.76295(19) 1.03046(17) 0.0504(5) Uani 1 1 d . . . . .
H22 H -0.1007 0.7480 1.1042 0.060 Uiso 1 1 calc R U . . .
C18 C 0.2420(2) 0.9199(2) 0.4845(2) 0.0626(6) Uani 1 1 d . . . . .
H18A H 0.2041 0.9851 0.5076 0.094 Uiso 1 1 calc R U . . .
H18B H 0.2200 0.8457 0.5527 0.094 Uiso 1 1 calc R U . . .
H18C H 0.1943 0.9281 0.4259 0.094 Uiso 1 1 calc R U . . .
C26 C -0.0325(3) 0.7283(2) 0.8590(2) 0.0575(6) Uani 1 1 d . . . . .
H26 H 0.0332 0.6892 0.8140 0.069 Uiso 1 1 calc R U . . .
C12 C 1.1669(3) 0.84861(19) 0.1477(2) 0.0629(6) Uani 1 1 d . . . . .
H12A H 1.1473 0.9331 0.1306 0.076 Uiso 1 1 calc R U . . .
H12B H 1.1142 0.8220 0.1118 0.076 Uiso 1 1 calc R U . . .
C19 C 0.6355(3) 1.16390(19) 0.1909(3) 0.0792(8) Uani 1 1 d . . . . .
H19A H 0.5857 1.1803 0.1307 0.119 Uiso 1 1 calc R U . . .
H19B H 0.7427 1.1669 0.1567 0.119 Uiso 1 1 calc R U . . .
H19C H 0.5980 1.2227 0.2230 0.119 Uiso 1 1 calc R U . . .
C27 C 0.3107(3) 0.4900(3) 0.9904(3) 0.0835(8) Uani 1 1 d . . . . .
H27A H 0.2761 0.4260 1.0677 0.100 Uiso 1 1 calc R U . . .
H27B H 0.3767 0.5345 0.9974 0.100 Uiso 1 1 calc R U . . .
C28 C 0.3903(4) 0.4420(3) 0.9062(3) 0.0964(10) Uani 1 1 d . . . . .
H28A H 0.4294 0.5056 0.8312 0.145 Uiso 1 1 calc R U . . .
H28B H 0.3227 0.4018 0.8968 0.145 Uiso 1 1 calc R U . . .
H28C H 0.4727 0.3862 0.9335 0.145 Uiso 1 1 calc R U . . .
H2B H 0.646(3) 0.434(2) 0.381(2) 0.061(7) Uiso 1 1 d . . . . .
H2C H 0.794(3) 0.378(2) 0.375(2) 0.067(7) 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
F1 C2 1.3565(18) . ?
F2 C4 1.3594(19) . ?
O1 C7 1.267(2) . ?
N1 C9 1.342(2) . ?
N1 C1 1.398(2) . ?
N1 C11 1.463(2) . ?
O3 C10 1.210(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.418(2) . ?
C6 C5 1.424(2) . ?
C6 C7 1.448(2) . ?
C8 C9 1.356(3) . ?
C8 C7 1.431(2) . ?
C8 C10 1.486(2) . ?
N3 C3 1.384(2) . ?
N3 C14 1.459(2) . ?
N3 C17 1.460(2) . ?
N4 C15 1.471(2) . ?
N4 C16 1.474(2) . ?
C3 C4 1.389(2) . ?
C3 C2 1.396(2) . ?
O2 C10 1.322(2) . ?
N2 C5 1.354(2) . ?
C5 C4 1.390(2) . ?
O5 C20 1.330(3) . ?
O5 C27 1.445(3) . ?
C15 C18 1.518(3) . ?
C15 C14 1.519(2) . ?
O6 C24 1.348(2) . ?
O4 C20 1.203(3) . ?
C17 C16 1.517(2) . ?
C16 C19 1.520(3) . ?
C11 C12 1.478(3) . ?
C11 C13 1.480(3) . ?
C21 C22 1.384(3) . ?
C21 C26 1.388(3) . ?
C21 C20 1.467(3) . ?
C24 C25 1.380(3) . ?
C24 C23 1.382(3) . ?
C25 C26 1.381(3) . ?
C13 C12 1.487(3) . ?
C23 C22 1.375(3) . ?
C27 C28 1.449(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
C9 N1 C1 119.77(14) . . ?
C9 N1 C11 118.19(15) . . ?
C1 N1 C11 121.28(13) . . ?
C2 C1 N1 121.19(14) . . ?
C2 C1 C6 119.26(15) . . ?
N1 C1 C6 119.55(14) . . ?
C1 C6 C5 118.93(14) . . ?
C1 C6 C7 119.28(15) . . ?
C5 C6 C7 121.79(15) . . ?
C9 C8 C7 119.84(15) . . ?
C9 C8 C10 117.79(16) . . ?
C7 C8 C10 122.16(16) . . ?
C3 N3 C14 121.97(14) . . ?
C3 N3 C17 119.99(14) . . ?
C14 N3 C17 113.65(13) . . ?
C15 N4 C16 111.68(14) . . ?
N3 C3 C4 124.67(15) . . ?
N3 C3 C2 119.73(15) . . ?
C4 C3 C2 115.57(14) . . ?
O1 C7 C8 120.77(15) . . ?
O1 C7 C6 122.11(16) . . ?
C8 C7 C6 117.11(15) . . ?
N2 C5 C4 119.46(17) . . ?
N2 C5 C6 122.79(16) . . ?
C4 C5 C6 117.72(15) . . ?
F1 C2 C1 119.93(14) . . ?
F1 C2 C3 116.92(14) . . ?
C1 C2 C3 123.02(15) . . ?
F2 C4 C3 119.31(14) . . ?
F2 C4 C5 115.83(15) . . ?
C3 C4 C5 124.86(15) . . ?
C20 O5 C27 115.30(19) . . ?
N1 C9 C8 123.81(16) . . ?
N4 C15 C18 109.73(16) . . ?
N4 C15 C14 108.75(15) . . ?
C18 C15 C14 111.08(16) . . ?
O3 C10 O2 121.33(16) . . ?
O3 C10 C8 123.68(18) . . ?
O2 C10 C8 114.99(17) . . ?
N3 C14 C15 109.34(15) . . ?
N3 C17 C16 109.87(15) . . ?
N4 C16 C17 107.95(15) . . ?
N4 C16 C19 110.04(17) . . ?
C17 C16 C19 111.52(18) . . ?
N1 C11 C12 118.00(17) . . ?
N1 C11 C13 118.76(16) . . ?
C12 C11 C13 60.37(16) . . ?
C22 C21 C26 118.48(18) . . ?
C22 C21 C20 118.39(18) . . ?
C26 C21 C20 123.11(19) . . ?
O6 C24 C25 123.16(19) . . ?
O6 C24 C23 117.41(19) . . ?
C25 C24 C23 119.43(19) . . ?
C24 C25 C26 120.46(19) . . ?
O4 C20 O5 122.6(2) . . ?
O4 C20 C21 124.6(2) . . ?
O5 C20 C21 112.75(17) . . ?
C11 C13 C12 59.72(15) . . ?
C22 C23 C24 119.9(2) . . ?
C23 C22 C21 121.27(18) . . ?
C25 C26 C21 120.4(2) . . ?
C11 C12 C13 59.91(15) . . ?
O5 C27 C28 108.0(3) . . ?

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.195

####################################################################### 
# 
# 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_SPX-IBZ
_database_code_depnum_ccdc_archive 'CCDC 1498304'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 5-Amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid-4-hydroxy-isobutylbenzoate 
;
_chemical_name_common            'Sparfloxacin-Isobutylparaben corystal'
_chemical_melting_point          348K
_chemical_formula_moiety         'C19 H22 F2 N4 O3, C11 H14 O3'
_chemical_formula_sum            'C30 H36 F2 N4 O6'
_chemical_formula_weight         586.63

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

_space_group_crystal_system      Triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5693(7)
_cell_length_b                   9.7134(7)
_cell_length_c                   17.7964(12)
_cell_angle_alpha                74.767(3)
_cell_angle_beta                 76.025(3)
_cell_angle_gamma                69.597(3)
_cell_volume                     1475.24(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4154
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      23.63

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30595
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_av_R_equivalents  0.1342
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.281
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_full        25.104
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5258
_reflns_number_gt                2755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.8830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5258
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_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 0.4489(3) 0.1787(3) 0.86584(17) 0.0343(8) Uani 1 1 d . . . . .
C2 C 0.5115(4) 0.2928(4) 0.82936(18) 0.0396(8) Uani 1 1 d . . . . .
C3 C 0.6645(4) 0.2770(4) 0.82204(18) 0.0415(8) Uani 1 1 d . . . . .
C4 C 0.7528(4) 0.1363(4) 0.8533(2) 0.0436(9) Uani 1 1 d . . . . .
C5 C 0.7030(4) 0.0132(4) 0.88622(18) 0.0395(8) Uani 1 1 d . . . . .
C6 C 0.5461(3) 0.0335(3) 0.89248(17) 0.0343(8) Uani 1 1 d . . . . .
C7 C 0.4846(4) -0.0905(4) 0.92360(18) 0.0392(8) Uani 1 1 d . . . . .
C8 C 0.3279(4) -0.0615(4) 0.92136(18) 0.0396(8) Uani 1 1 d . . . . .
C9 C 0.2405(4) 0.0820(4) 0.89864(18) 0.0426(9) Uani 1 1 d . . . . .
H9 H 0.1381 0.0985 0.9005 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2548(5) -0.1819(4) 0.9453(2) 0.0523(10) Uani 1 1 d . . . . .
C11 C 0.1837(3) 0.3519(4) 0.8603(2) 0.0428(9) Uani 1 1 d . . . . .
H11 H 0.1757 0.3996 0.8050 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1645(4) 0.4533(4) 0.9139(2) 0.0521(10) Uani 1 1 d . . . . .
H12A H 0.1472 0.5591 0.8914 0.063 Uiso 1 1 calc R U . . .
H12B H 0.2231 0.4151 0.9565 0.063 Uiso 1 1 calc R U . . .
C13 C 0.0424(4) 0.3880(4) 0.9181(2) 0.0544(10) Uani 1 1 d . . . . .
H13A H 0.0270 0.3102 0.9633 0.065 Uiso 1 1 calc R U . . .
H13B H -0.0489 0.4541 0.8981 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8729(4) 0.3670(4) 0.7342(2) 0.0520(10) Uani 1 1 d . . . . .
H14A H 0.9073 0.2682 0.7213 0.062 Uiso 1 1 calc R U . . .
H14B H 0.9427 0.3710 0.7645 0.062 Uiso 1 1 calc R U . . .
C15 C 0.8703(4) 0.4845(4) 0.6593(2) 0.0507(9) Uani 1 1 d . . . . .
H15 H 0.8070 0.4730 0.6270 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6516(4) 0.6599(4) 0.72628(19) 0.0437(9) Uani 1 1 d . . . . .
H16 H 0.5838 0.6508 0.6957 0.052 Uiso 1 1 calc R U . . .
C17 C 0.6585(4) 0.5414(4) 0.80021(19) 0.0451(9) Uani 1 1 d . . . . .
H17A H 0.7205 0.5535 0.8324 0.054 Uiso 1 1 calc R U . . .
H17B H 0.5576 0.5525 0.8305 0.054 Uiso 1 1 calc R U . . .
C18 C 1.0282(5) 0.4697(5) 0.6120(2) 0.0806(14) Uani 1 1 d . . . . .
H18A H 1.0239 0.5510 0.5673 0.121 Uiso 1 1 calc R U . . .
H18B H 1.0672 0.3763 0.5941 0.121 Uiso 1 1 calc R U . . .
H18C H 1.0932 0.4724 0.6447 0.121 Uiso 1 1 calc R U . . .
C19 C 0.5967(4) 0.8167(4) 0.7428(2) 0.0570(10) Uani 1 1 d . . . . .
H19A H 0.6657 0.8281 0.7702 0.086 Uiso 1 1 calc R U . . .
H19B H 0.4982 0.8336 0.7748 0.086 Uiso 1 1 calc R U . . .
H19C H 0.5913 0.8881 0.6938 0.086 Uiso 1 1 calc R U . . .
C20 C 0.2625(4) 0.1196(4) 0.5503(2) 0.0491(9) Uani 1 1 d . . . . .
C21 C 0.1853(4) 0.0187(4) 0.6068(2) 0.0456(9) Uani 1 1 d . . . . .
C22 C 0.2365(5) -0.0698(5) 0.6742(2) 0.0880(16) Uani 1 1 d . . . . .
H22 H 0.3193 -0.0595 0.6883 0.106 Uiso 1 1 calc R U . . .
C23 C 0.1694(5) -0.1732(6) 0.7214(3) 0.0983(18) Uani 1 1 d . . . . .
H23 H 0.2074 -0.2315 0.7669 0.118 Uiso 1 1 calc R U . . .
C24 C 0.0475(4) -0.1924(4) 0.7032(2) 0.0542(10) Uani 1 1 d . . . . .
C25 C -0.0105(4) -0.0988(4) 0.6381(2) 0.0654(12) Uani 1 1 d . . . . .
H25 H -0.0968 -0.1054 0.6258 0.078 Uiso 1 1 calc R U . . .
C26 C 0.0579(4) 0.0047(4) 0.5909(2) 0.0598(11) Uani 1 1 d . . . . .
H26 H 0.0167 0.0669 0.5470 0.072 Uiso 1 1 calc R U . . .
C27 C 0.4654(4) 0.2228(4) 0.5230(2) 0.0619(11) Uani 1 1 d . . . . .
H27A H 0.3993 0.3254 0.5164 0.074 Uiso 1 1 calc R U . . .
H27B H 0.5019 0.1960 0.4714 0.074 Uiso 1 1 calc R U . . .
C28 C 0.5960(4) 0.2091(4) 0.5599(2) 0.0618(11) Uani 1 1 d . . . . .
H28 H 0.6604 0.1046 0.5657 0.074 Uiso 1 1 calc R U . . .
C29 C 0.5457(6) 0.2483(6) 0.6406(3) 0.1062(18) Uani 1 1 d . . . . .
H29A H 0.4835 0.3509 0.6364 0.159 Uiso 1 1 calc R U . . .
H29B H 0.6328 0.2346 0.6628 0.159 Uiso 1 1 calc R U . . .
H29C H 0.4889 0.1843 0.6742 0.159 Uiso 1 1 calc R U . . .
C30 C 0.6892(5) 0.3066(5) 0.5047(3) 0.0836(14) Uani 1 1 d . . . . .
H30A H 0.7197 0.2790 0.4538 0.125 Uiso 1 1 calc R U . . .
H30B H 0.7772 0.2920 0.5262 0.125 Uiso 1 1 calc R U . . .
H30C H 0.6292 0.4100 0.4992 0.125 Uiso 1 1 calc R U . . .
N1 N 0.2923(3) 0.2014(3) 0.87376(14) 0.0378(7) Uani 1 1 d . . . . .
N2 N 0.8031(3) -0.1200(3) 0.91251(17) 0.0538(8) Uani 1 1 d . . . . .
H2B H 0.8966 -0.1267 0.9085 0.065 Uiso 1 1 calc R U . . .
H2C H 0.7731 -0.1975 0.9332 0.065 Uiso 1 1 calc R U . . .
N3 N 0.7216(3) 0.3933(3) 0.78105(17) 0.0515(8) Uani 1 1 d . . . . .
N4 N 0.8052(3) 0.6347(3) 0.67924(17) 0.0432(7) Uani 1 1 d . . . . .
O1 O 0.5657(3) -0.2218(3) 0.95015(13) 0.0505(6) Uani 1 1 d . . . . .
O2 O 0.3404(3) -0.3169(3) 0.97368(17) 0.0713(8) Uani 1 1 d . . . . .
O3 O 0.1260(3) -0.1607(3) 0.93838(17) 0.0759(9) Uani 1 1 d . . . . .
O4 O 0.2245(3) 0.1929(3) 0.48854(16) 0.0721(8) Uani 1 1 d . . . . .
O5 O 0.3835(3) 0.1239(3) 0.57372(14) 0.0615(7) Uani 1 1 d . . . . .
O6 O -0.0075(3) -0.3030(3) 0.74888(14) 0.0725(8) Uani 1 1 d . . . . .
H6A H -0.0784 -0.3047 0.7313 0.109 Uiso 1 1 calc R U . . .
F1 F 0.4275(2) 0.4261(2) 0.79025(11) 0.0541(5) Uani 1 1 d . . . . .
F2 F 0.9024(2) 0.1157(2) 0.85238(13) 0.0644(6) Uani 1 1 d . . . . .
H2A H 0.441(5) -0.306(5) 0.973(3) 0.112(17) Uiso 1 1 d . . . . .
H4A H 0.799(4) 0.700(4) 0.635(2) 0.053(11) 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
C1 C2 1.381(4) . ?
C1 N1 1.413(4) . ?
C1 C6 1.424(4) . ?
C2 F1 1.370(3) . ?
C2 C3 1.395(4) . ?
C3 N3 1.382(4) . ?
C3 C4 1.383(4) . ?
C4 F2 1.371(3) . ?
C4 C5 1.377(4) . ?
C5 N2 1.358(4) . ?
C5 C6 1.424(4) . ?
C6 C7 1.445(4) . ?
C7 O1 1.274(4) . ?
C7 C8 1.435(4) . ?
C8 C9 1.364(4) . ?
C8 C10 1.485(4) . ?
C9 N1 1.346(4) . ?
C10 O3 1.208(4) . ?
C10 O2 1.323(4) . ?
C11 N1 1.467(4) . ?
C11 C12 1.483(5) . ?
C11 C13 1.483(5) . ?
C12 C13 1.491(4) . ?
C14 N3 1.458(4) . ?
C14 C15 1.509(4) . ?
C15 N4 1.475(4) . ?
C15 C18 1.520(5) . ?
C16 N4 1.478(4) . ?
C16 C17 1.501(4) . ?
C16 C19 1.512(4) . ?
C17 N3 1.451(4) . ?
C20 O4 1.204(4) . ?
C20 O5 1.339(4) . ?
C20 C21 1.464(5) . ?
C21 C22 1.366(5) . ?
C21 C26 1.374(4) . ?
C22 C23 1.369(5) . ?
C23 C24 1.367(5) . ?
C24 O6 1.349(4) . ?
C24 C25 1.371(5) . ?
C25 C26 1.377(5) . ?
C27 O5 1.443(4) . ?
C27 C28 1.498(5) . ?
C28 C29 1.505(6) . ?
C28 C30 1.529(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
C2 C1 N1 121.5(3) . . ?
C2 C1 C6 118.8(3) . . ?
N1 C1 C6 119.6(3) . . ?
F1 C2 C1 120.7(3) . . ?
F1 C2 C3 115.4(3) . . ?
C1 C2 C3 123.6(3) . . ?
N3 C3 C4 123.8(3) . . ?
N3 C3 C2 120.7(3) . . ?
C4 C3 C2 115.4(3) . . ?
F2 C4 C5 116.3(3) . . ?
F2 C4 C3 118.3(3) . . ?
C5 C4 C3 125.4(3) . . ?
N2 C5 C4 119.3(3) . . ?
N2 C5 C6 123.1(3) . . ?
C4 C5 C6 117.6(3) . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 C7 119.6(3) . . ?
C5 C6 C7 121.4(3) . . ?
O1 C7 C8 120.6(3) . . ?
O1 C7 C6 122.1(3) . . ?
C8 C7 C6 117.3(3) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 C10 118.1(3) . . ?
C7 C8 C10 122.4(3) . . ?
N1 C9 C8 124.4(3) . . ?
O3 C10 O2 121.1(3) . . ?
O3 C10 C8 123.0(4) . . ?
O2 C10 C8 115.9(3) . . ?
N1 C11 C12 118.2(3) . . ?
N1 C11 C13 118.8(3) . . ?
C12 C11 C13 60.4(2) . . ?
C11 C12 C13 59.8(2) . . ?
C11 C13 C12 59.8(2) . . ?
N3 C14 C15 109.6(3) . . ?
N4 C15 C14 109.5(3) . . ?
N4 C15 C18 109.0(3) . . ?
C14 C15 C18 111.5(3) . . ?
N4 C16 C17 108.3(3) . . ?
N4 C16 C19 108.5(3) . . ?
C17 C16 C19 112.8(3) . . ?
N3 C17 C16 110.6(3) . . ?
O4 C20 O5 121.6(3) . . ?
O4 C20 C21 125.2(3) . . ?
O5 C20 C21 113.3(3) . . ?
C22 C21 C26 116.7(3) . . ?
C22 C21 C20 123.6(3) . . ?
C26 C21 C20 119.6(3) . . ?
C21 C22 C23 121.8(4) . . ?
C24 C23 C22 121.3(4) . . ?
O6 C24 C23 118.7(3) . . ?
O6 C24 C25 123.7(3) . . ?
C23 C24 C25 117.6(3) . . ?
C24 C25 C26 120.6(3) . . ?
C21 C26 C25 121.8(3) . . ?
O5 C27 C28 108.6(3) . . ?
C27 C28 C29 112.2(4) . . ?
C27 C28 C30 109.3(3) . . ?
C29 C28 C30 111.4(3) . . ?
C9 N1 C1 119.1(3) . . ?
C9 N1 C11 119.0(3) . . ?
C1 N1 C11 121.8(2) . . ?
C3 N3 C17 121.9(3) . . ?
C3 N3 C14 122.0(3) . . ?
C17 N3 C14 113.5(3) . . ?
C15 N4 C16 113.3(3) . . ?
C20 O5 C27 117.6(3) . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.048

