# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_LH_ME_0p38
_database_code_depnum_ccdc_archive 'CCDC 2481326'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_LEVO_05_H2O_181022

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.5(H2 O1)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   28.512(5)
_cell_length_b                   6.7261(4)
_cell_length_c                   18.5315(13)
_cell_angle_alpha                90
_cell_angle_beta                 113.557(12)
_cell_angle_gamma                90
_cell_volume                     3257.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7699
_cell_measurement_theta_min      3.127
_cell_measurement_theta_max      23.313
_exptl_crystal_description       Lathe
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6681
_exptl_absorpt_correction_t_max  0.7449
_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 D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7699
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.127
_diffrn_reflns_theta_max         23.313
_diffrn_reflns_theta_full        23.313
_diffrn_measured_fraction_theta_max 0.318
_diffrn_measured_fraction_theta_full 0.318
_diffrn_reflns_Laue_measured_fraction_max 0.318
_diffrn_reflns_Laue_measured_fraction_full 0.318
_diffrn_reflns_point_group_measured_fraction_max 0.323
_diffrn_reflns_point_group_measured_fraction_full 0.323
_reflns_number_total             1529
_reflns_number_gt                1116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.328
_reflns_Friedel_fraction_full    0.328
_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       'Apex 4 suite'
_computing_cell_refinement       'Apex 4 suite'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1965P)²+0.3489P] 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_abs_structure_details 
;
 Flack x determined using 393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1529
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2592
_refine_ls_wR_factor_gt          0.2300
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.479
_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
F1 F 0.2075(9) 0.4627(12) 0.7343(7) 0.056(3) Uiso 1 1 d D U . . .
O1 O 0.3207(12) 0.4854(16) 1.2262(10) 0.063(4) Uiso 1 1 d D U . . .
O2 O 0.3722(12) 0.4893(17) 1.1618(10) 0.066(4) Uiso 1 1 d D U . . .
H2 H 0.368691 0.501733 1.115894 0.098 Uiso 1 1 calc R U . . .
O3 O 0.3348(12) 0.4860(14) 1.0130(9) 0.050(4) Uiso 1 1 d D U . . .
O4 O 0.1039(12) 0.4696(15) 0.8777(9) 0.052(3) Uiso 1 1 d D U . . .
N1 N 0.1924(10) 0.4706(15) 1.0209(9) 0.029(3) Uiso 1 1 d D U . . .
N2 N 0.1107(11) 0.4891(16) 0.7317(10) 0.047(4) Uiso 1 1 d D U . . .
N3 N 0.0173(11) 0.6384(18) 0.6281(9) 0.052(4) Uiso 1 1 d D U . . .
C1 C 0.2359(11) 0.4721(18) 1.0865(11) 0.030(4) Uiso 1 1 d D U . . .
H1 H 0.233163 0.470036 1.134873 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2837(11) 0.4766(19) 1.0865(10) 0.034(4) Uiso 1 1 d D U . . .
C3 C 0.2911(11) 0.4815(19) 1.0146(9) 0.028(4) Uiso 1 1 d D U . . .
C4 C 0.2460(13) 0.477(2) 0.8692(12) 0.045(4) Uiso 1 1 d D U . . .
H4 H 0.277296 0.483137 0.864728 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2018(12) 0.4712(18) 0.8042(11) 0.027(4) Uiso 1 1 d D U . . .
C6 C 0.1522(12) 0.481(2) 0.8023(10) 0.049(5) Uiso 1 1 d D U . . .
C7 C 0.1522(12) 0.473(2) 0.8781(10) 0.041(5) Uiso 1 1 d D U . . .
C8 C 0.1965(12) 0.4701(19) 0.9481(10) 0.029(4) Uiso 1 1 d D U . . .
C9 C 0.2439(12) 0.4746(19) 0.9432(10) 0.030(4) Uiso 1 1 d D U . . .
C10 C 0.3264(12) 0.484(2) 1.1649(10) 0.038(4) Uiso 1 1 d D U . . .
C11 C 0.1023(12) 0.549(2) 0.9479(9) 0.047(4) Uiso 1 1 d D U . . .
H11A H 0.068206 0.531245 0.946528 0.057 Uiso 1 1 calc R U . . .
H11B H 0.109366 0.690171 0.950341 0.057 Uiso 1 1 calc R U . . .
C12 C 0.1406(10) 0.4501(18) 1.0211(8) 0.031(3) Uiso 1 1 d D U . . .
H12 H 0.132121 0.308827 1.020934 0.037 Uiso 1 1 calc R U . . .
C13 C 0.137(2) 0.551(2) 1.0917(15) 0.055(5) Uiso 1 1 d D U . . .
H13A H 0.163301 0.500827 1.139088 0.083 Uiso 1 1 calc R U . . .
H13B H 0.104020 0.523008 1.092562 0.083 Uiso 1 1 calc R U . . .
H13C H 0.140834 0.691523 1.088372 0.083 Uiso 1 1 calc R U . . .
C14 C 0.0639(11) 0.374(2) 0.7137(11) 0.046(4) Uiso 1 1 d D U . . .
H14A H 0.067271 0.293169 0.758824 0.055 Uiso 1 1 calc R U . . .
H14B H 0.058734 0.285908 0.669742 0.055 Uiso 1 1 calc R U . . .
C15 C 0.0185(12) 0.5092(19) 0.6934(11) 0.048(4) Uiso 1 1 d D U . . .
H15A H -0.012708 0.431936 0.677434 0.058 Uiso 1 1 calc R U . . .
H15B H 0.021704 0.589105 0.738740 0.058 Uiso 1 1 calc R U . . .
C16 C 0.0644(11) 0.758(2) 0.6520(11) 0.055(5) Uiso 1 1 d D U . . .
H16A H 0.068196 0.837026 0.697826 0.066 Uiso 1 1 calc R U . . .
H16B H 0.061724 0.848471 0.609757 0.066 Uiso 1 1 calc R U . . .
C17 C 0.1111(13) 0.628(2) 0.6712(12) 0.055(5) Uiso 1 1 d D U . . .
H17A H 0.109374 0.556603 0.624770 0.066 Uiso 1 1 calc R U . . .
H17B H 0.141983 0.707687 0.690804 0.066 Uiso 1 1 calc R U . . .
C18 C -0.0292(13) 0.760(3) 0.6037(14) 0.084(7) Uiso 1 1 d D U . . .
H18A H -0.058712 0.674988 0.586085 0.126 Uiso 1 1 calc R U . . .
H18B H -0.030888 0.846629 0.561536 0.126 Uiso 1 1 calc R U . . .
H18C H -0.028524 0.838226 0.647464 0.126 Uiso 1 1 calc R U . . .
F2 F 0.2901(9) 0.7109(12) 0.7605(7) 0.050(3) Uiso 1 1 d D U . . .
O5 O 0.1791(13) 0.6809(15) 0.2664(11) 0.063(4) Uiso 1 1 d D U . . .
O6 O 0.1287(11) 0.6948(16) 0.3290(9) 0.064(4) Uiso 1 1 d D U . . .
H6 H 0.131388 0.694277 0.374739 0.096 Uiso 1 1 calc R U . . .
O7 O 0.1630(11) 0.6779(15) 0.4772(9) 0.056(4) Uiso 1 1 d D U . . .
O8 O 0.3941(12) 0.6782(14) 0.6212(9) 0.055(4) Uiso 1 1 d D U . . .
N4 N 0.3078(10) 0.6544(15) 0.4785(9) 0.039(4) Uiso 1 1 d D U . . .
N5 N 0.3863(11) 0.6893(15) 0.7636(9) 0.045(4) Uiso 1 1 d D U . . .
N6 N 0.4834(11) 0.5853(18) 0.8789(9) 0.050(4) Uiso 1 1 d D U . . .
C19 C 0.2662(10) 0.6590(19) 0.4107(11) 0.037(4) Uiso 1 1 d D U . . .
H19 H 0.270750 0.653101 0.363755 0.045 Uiso 1 1 calc R U . . .
C20 C 0.2174(10) 0.6721(17) 0.4069(9) 0.026(4) Uiso 1 1 d D U . . .
C21 C 0.2067(10) 0.6726(18) 0.4757(9) 0.034(4) Uiso 1 1 d D U . . .
C22 C 0.2502(13) 0.6844(19) 0.6237(11) 0.042(4) Uiso 1 1 d D U . . .
H22 H 0.218691 0.684205 0.627748 0.051 Uiso 1 1 calc R U . . .
C23 C 0.2940(12) 0.6930(17) 0.6901(11) 0.032(4) Uiso 1 1 d D U . . .
C24 C 0.3437(11) 0.684(2) 0.6932(9) 0.042(5) Uiso 1 1 d D U . . .
C25 C 0.3454(11) 0.682(2) 0.6177(10) 0.041(4) Uiso 1 1 d D U . . .
C26 C 0.3012(11) 0.6730(17) 0.5493(10) 0.029(4) Uiso 1 1 d D U . . .
C27 C 0.2518(10) 0.6758(18) 0.5496(9) 0.034(4) Uiso 1 1 d D U . . .
C28 C 0.1746(11) 0.687(2) 0.3277(10) 0.047(5) Uiso 1 1 d D U . . .
C29 C 0.3973(11) 0.7346(19) 0.5477(8) 0.038(4) Uiso 1 1 d D U . . .
H29A H 0.431652 0.711070 0.551067 0.045 Uiso 1 1 calc R U . . .
H29B H 0.389830 0.875207 0.538041 0.045 Uiso 1 1 calc R U . . .
C30 C 0.3599(10) 0.616(2) 0.4815(8) 0.036(4) Uiso 1 1 d D U . . .
H30 H 0.367645 0.475209 0.493833 0.043 Uiso 1 1 calc R U . . .
C31 C 0.3645(18) 0.658(3) 0.4047(13) 0.058(5) Uiso 1 1 d D U . . .
H31A H 0.350316 0.548669 0.369281 0.086 Uiso 1 1 calc R U . . .
H31B H 0.399868 0.673978 0.414029 0.086 Uiso 1 1 calc R U . . .
H31C H 0.346111 0.777331 0.381965 0.086 Uiso 1 1 calc R U . . .
C32 C 0.4291(11) 0.820(2) 0.7797(11) 0.041(4) Uiso 1 1 d D U . . .
H32A H 0.430495 0.916367 0.819429 0.049 Uiso 1 1 calc R U . . .
H32B H 0.425479 0.891257 0.732273 0.049 Uiso 1 1 calc R U . . .
C33 C 0.4770(12) 0.699(2) 0.8082(10) 0.047(4) Uiso 1 1 d D U . . .
H33A H 0.476112 0.608913 0.766951 0.056 Uiso 1 1 calc R U . . .
H33B H 0.506137 0.787163 0.819891 0.056 Uiso 1 1 calc R U . . .
C34 C 0.4386(12) 0.454(2) 0.8562(11) 0.042(4) Uiso 1 1 d D U . . .
H34A H 0.441810 0.372148 0.900869 0.050 Uiso 1 1 calc R U . . .
H34B H 0.438231 0.367117 0.814287 0.050 Uiso 1 1 calc R U . . .
C35 C 0.3895(13) 0.5640(19) 0.8292(10) 0.037(4) Uiso 1 1 d D U . . .
H35A H 0.361093 0.471204 0.812790 0.044 Uiso 1 1 calc R U . . .
H35B H 0.388134 0.644834 0.871709 0.044 Uiso 1 1 calc R U . . .
C36 C 0.5312(14) 0.472(3) 0.9075(13) 0.078(6) Uiso 1 1 d D U . . .
H36A H 0.532268 0.389790 0.865882 0.117 Uiso 1 1 calc R U . . .
H36B H 0.533124 0.390506 0.950994 0.117 Uiso 1 1 calc R U . . .
H36C H 0.559656 0.562670 0.924281 0.117 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.361(3) 0.500000 0.073(7) Uiso 1 2 d DGS . P . .
H9A H -0.027359 0.295466 0.475899 0.110 Uiso 0.5 1 d DG U P . .
H9B H 0.000595 0.446679 0.466756 0.110 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.377(3) 1.000000 0.074(6) Uiso 1 2 d DGS . P . .
H10A H 0.004876 0.467518 1.034030 0.111 Uiso 0.5 1 d DG U P . .
H10B H 0.006064 0.269650 1.026446 0.111 Uiso 0.5 1 d DG U P . .
_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 C5 1.370(11) . ?
O1 C10 1.211(12) . ?
O2 C10 1.329(15) . ?
O2 H2 0.8200 . ?
O3 C3 1.262(15) . ?
O4 C7 1.374(14) . ?
O4 C11 1.422(12) . ?
N1 C1 1.345(14) . ?
N1 C8 1.401(12) . ?
N1 C12 1.485(14) . ?
N2 C6 1.371(14) . ?
N2 C14 1.460(15) . ?
N2 C17 1.462(12) . ?
N3 C18 1.469(15) . ?
N3 C16 1.473(15) . ?
N3 C15 1.479(12) . ?
C1 C2 1.365(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.428(13) . ?
C2 C10 1.478(14) . ?
C3 C9 1.462(14) . ?
C4 C5 1.352(15) . ?
C4 C9 1.395(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(14) . ?
C6 C7 1.406(13) . ?
C7 C8 1.403(14) . ?
C8 C9 1.392(14) . ?
C11 C12 1.512(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.514(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.501(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.511(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.358(12) . ?
O5 C28 1.195(13) . ?
O6 C28 1.320(15) . ?
O6 H6 0.8200 . ?
O7 C21 1.257(15) . ?
O8 C25 1.363(15) . ?
O8 C29 1.452(12) . ?
N4 C19 1.339(14) . ?
N4 C26 1.405(12) . ?
N4 C30 1.488(14) . ?
N5 C24 1.382(14) . ?
N5 C32 1.436(14) . ?
N5 C35 1.453(12) . ?
N6 C36 1.463(15) . ?
N6 C33 1.466(12) . ?
N6 C34 1.466(15) . ?
C19 C20 1.367(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.426(14) . ?
C20 C28 1.490(14) . ?
C21 C27 1.458(14) . ?
C22 C23 1.360(15) . ?
C22 C27 1.394(13) . ?
C22 H22 0.9300 . ?
C23 C24 1.398(14) . ?
C24 C25 1.419(13) . ?
C25 C26 1.387(14) . ?
C26 C27 1.409(15) . ?
C29 C30 1.493(14) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.505(13) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.491(15) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.482(15) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8494 . ?
O9 H9B 0.8505 . ?
O9 H9A 0.8(4) 2_556 ?
O9 H9B 0.9(4) 2_556 ?
O10 H10A 0.8463 . ?
O10 H10B 0.8517 . ?
O10 H10A 0.8(3) 2_557 ?
O10 H10B 0.9(3) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 113(2) . . ?
C1 N1 C8 118(2) . . ?
C1 N1 C12 123.9(12) . . ?
C8 N1 C12 117.9(19) . . ?
C6 N2 C14 123.9(14) . . ?
C6 N2 C17 119.3(19) . . ?
C14 N2 C17 116.7(19) . . ?
C18 N3 C16 113.0(14) . . ?
C18 N3 C15 107.6(18) . . ?
C16 N3 C15 110.8(18) . . ?
N1 C1 C2 124.1(15) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 121(2) . . ?
C1 C2 C10 115.5(14) . . ?
C3 C2 C10 123(2) . . ?
O3 C3 C2 123(2) . . ?
O3 C3 C9 122.6(14) . . ?
C2 C3 C9 114.8(19) . . ?
C5 C4 C9 119(2) . . ?
C5 C4 H4 120.5 . . ?
C9 C4 H4 120.5 . . ?
C4 C5 F1 115(2) . . ?
C4 C5 C6 126.3(14) . . ?
F1 C5 C6 119(2) . . ?
N2 C6 C5 120.2(16) . . ?
N2 C6 C7 128(2) . . ?
C5 C6 C7 112.1(19) . . ?
O4 C7 C8 122.4(15) . . ?
O4 C7 C6 113.3(19) . . ?
C8 C7 C6 124(2) . . ?
C9 C8 N1 121.3(19) . . ?
C9 C8 C7 118.6(13) . . ?
N1 C8 C7 120(2) . . ?
C8 C9 C4 119(2) . . ?
C8 C9 C3 120.4(13) . . ?
C4 C9 C3 120(2) . . ?
O1 C10 O2 123(2) . . ?
O1 C10 C2 124(2) . . ?
O2 C10 C2 113.3(15) . . ?
O4 C11 C12 112.4(16) . . ?
O4 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
O4 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 C11 108.6(15) . . ?
N1 C12 C13 112(2) . . ?
C11 C12 C13 107.8(19) . . ?
N1 C12 H12 109.5 . . ?
C11 C12 H12 109.5 . . ?
C13 C12 H12 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 110.7(13) . . ?
N2 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C14 107.2(17) . . ?
N3 C15 H15A 110.3 . . ?
C14 C15 H15A 110.3 . . ?
N3 C15 H15B 110.3 . . ?
C14 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
N3 C16 C17 111.4(15) . . ?
N3 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N3 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N2 C17 C16 106.0(18) . . ?
N2 C17 H17A 110.5 . . ?
C16 C17 H17A 110.5 . . ?
N2 C17 H17B 110.5 . . ?
C16 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 113(2) . . ?
C19 N4 C26 118.4(19) . . ?
C19 N4 C30 122.4(13) . . ?
C26 N4 C30 119.0(18) . . ?
C24 N5 C32 124.5(13) . . ?
C24 N5 C35 120.9(18) . . ?
C32 N5 C35 114.6(18) . . ?
C36 N6 C33 111.1(18) . . ?
C36 N6 C34 111.8(14) . . ?
C33 N6 C34 106.0(18) . . ?
N4 C19 C20 123.4(17) . . ?
N4 C19 H19 118.3 . . ?
C20 C19 H19 118.3 . . ?
C19 C20 C21 122(2) . . ?
C19 C20 C28 118.2(15) . . ?
C21 C20 C28 119.7(19) . . ?
O7 C21 C20 126.0(19) . . ?
O7 C21 C27 119.4(15) . . ?
C20 C21 C27 114.5(18) . . ?
C23 C22 C27 121(2) . . ?
C23 C22 H22 119.6 . . ?
C27 C22 H22 119.6 . . ?
F2 C23 C22 118(2) . . ?
F2 C23 C24 116(2) . . ?
C22 C23 C24 125.8(14) . . ?
N5 C24 C23 122.0(15) . . ?
N5 C24 C25 125(2) . . ?
C23 C24 C25 113.2(18) . . ?
O8 C25 C26 125.5(15) . . ?
O8 C25 C24 112.8(19) . . ?
C26 C25 C24 122(2) . . ?
C25 C26 N4 116.4(18) . . ?
C25 C26 C27 122.8(14) . . ?
N4 C26 C27 120.7(19) . . ?
C22 C27 C26 116(2) . . ?
C22 C27 C21 124(2) . . ?
C26 C27 C21 120.3(14) . . ?
O5 C28 O6 120(2) . . ?
O5 C28 C20 125(2) . . ?
O6 C28 C20 114.5(15) . . ?
O8 C29 C30 109.9(15) . . ?
O8 C29 H29A 109.7 . . ?
C30 C29 H29A 109.7 . . ?
O8 C29 H29B 109.7 . . ?
C30 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
N4 C30 C29 108.3(15) . . ?
N4 C30 C31 113(2) . . ?
C29 C30 C31 112.0(17) . . ?
N4 C30 H30 107.7 . . ?
C29 C30 H30 107.7 . . ?
C31 C30 H30 107.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 108.9(13) . . ?
N5 C32 H32A 109.9 . . ?
C33 C32 H32A 109.9 . . ?
N5 C32 H32B 109.9 . . ?
C33 C32 H32B 109.9 . . ?
H32A C32 H32B 108.3 . . ?
N6 C33 C32 111.7(19) . . ?
N6 C33 H33A 109.3 . . ?
C32 C33 H33A 109.3 . . ?
N6 C33 H33B 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 107.9 . . ?
N6 C34 C35 113.3(14) . . ?
N6 C34 H34A 108.9 . . ?
C35 C34 H34A 108.9 . . ?
N6 C34 H34B 108.9 . . ?
C35 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
N5 C35 C34 107.8(19) . . ?
N5 C35 H35A 110.1 . . ?
C34 C35 H35A 110.1 . . ?
N5 C35 H35B 110.1 . . ?
C34 C35 H35B 110.1 . . ?
H35A C35 H35B 108.5 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 104.5 . . ?
H9A O9 H9A 117.9 . 2_556 ?
H9B O9 H9A 116.9 . 2_556 ?
H9A O9 H9B 116.9 . 2_556 ?
H9B O9 H9B 94.2 . 2_556 ?
H9A O9 H9B 104.5 2_556 2_556 ?
H10A O10 H10B 104.2 . . ?
H10A O10 H10A 88.2 . 2_557 ?
H10B O10 H10A 166.8 . 2_557 ?
H10A O10 H10B 166.8 . 2_557 ?
H10B O10 H10B 63.8 . 2_557 ?
H10A O10 H10B 104.2 2_557 2_557 ?
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
C8 N1 C1 C2 1(2) . . . . ?
C12 N1 C1 C2 175.1(11) . . . . ?
N1 C1 C2 C3 0(2) . . . . ?
N1 C1 C2 C10 178.1(12) . . . . ?
C1 C2 C3 O3 179.9(13) . . . . ?
C10 C2 C3 O3 2(2) . . . . ?
C1 C2 C3 C9 -2.0(18) . . . . ?
C10 C2 C3 C9 -179.4(11) . . . . ?
C9 C4 C5 F1 -176.4(10) . . . . ?
C9 C4 C5 C6 6(2) . . . . ?
C14 N2 C6 C5 136.5(15) . . . . ?
C17 N2 C6 C5 -47(2) . . . . ?
C14 N2 C6 C7 -41(2) . . . . ?
C17 N2 C6 C7 135.5(17) . . . . ?
C4 C5 C6 N2 174.7(13) . . . . ?
F1 C5 C6 N2 -2(2) . . . . ?
C4 C5 C6 C7 -7(2) . . . . ?
F1 C5 C6 C7 175.4(11) . . . . ?
C11 O4 C7 C8 26(2) . . . . ?
C11 O4 C7 C6 -153.8(12) . . . . ?
N2 C6 C7 O4 2(2) . . . . ?
C5 C6 C7 O4 -176.1(13) . . . . ?
N2 C6 C7 C8 -178.3(14) . . . . ?
C5 C6 C7 C8 4(2) . . . . ?
C1 N1 C8 C9 -1.1(18) . . . . ?
C12 N1 C8 C9 -175.4(11) . . . . ?
C1 N1 C8 C7 -178.5(12) . . . . ?
C12 N1 C8 C7 7.1(17) . . . . ?
O4 C7 C8 C9 -179.9(12) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
O4 C7 C8 N1 -2(2) . . . . ?
C6 C7 C8 N1 177.4(12) . . . . ?
N1 C8 C9 C4 -178.9(11) . . . . ?
C7 C8 C9 C4 -1(2) . . . . ?
N1 C8 C9 C3 -0.5(19) . . . . ?
C7 C8 C9 C3 177.0(11) . . . . ?
C5 C4 C9 C8 -1(2) . . . . ?
C5 C4 C9 C3 -179.8(12) . . . . ?
O3 C3 C9 C8 -179.9(12) . . . . ?
C2 C3 C9 C8 2.0(18) . . . . ?
O3 C3 C9 C4 -1(2) . . . . ?
C2 C3 C9 C4 -179.6(12) . . . . ?
C1 C2 C10 O1 0(2) . . . . ?
C3 C2 C10 O1 177.9(13) . . . . ?
C1 C2 C10 O2 -179.6(13) . . . . ?
C3 C2 C10 O2 -2.1(19) . . . . ?
C7 O4 C11 C12 -54(2) . . . . ?
C1 N1 C12 C11 153.3(11) . . . . ?
C8 N1 C12 C11 -32.7(14) . . . . ?
C1 N1 C12 C13 34.4(19) . . . . ?
C8 N1 C12 C13 -151.6(13) . . . . ?
O4 C11 C12 N1 57(2) . . . . ?
O4 C11 C12 C13 178(2) . . . . ?
C6 N2 C14 C15 120.6(16) . . . . ?
C17 N2 C14 C15 -56.0(19) . . . . ?
C18 N3 C15 C14 175.5(15) . . . . ?
C16 N3 C15 C14 -60.5(16) . . . . ?
N2 C14 C15 N3 55.3(18) . . . . ?
C18 N3 C16 C17 -176.0(15) . . . . ?
C15 N3 C16 C17 63.2(18) . . . . ?
C6 N2 C17 C16 -123.0(19) . . . . ?
C14 N2 C17 C16 53.7(18) . . . . ?
N3 C16 C17 N2 -56(2) . . . . ?
C26 N4 C19 C20 -3(2) . . . . ?
C30 N4 C19 C20 172.6(12) . . . . ?
N4 C19 C20 C21 -3(2) . . . . ?
N4 C19 C20 C28 176.9(10) . . . . ?
C19 C20 C21 O7 -177.7(14) . . . . ?
C28 C20 C21 O7 2(2) . . . . ?
C19 C20 C21 C27 5.1(18) . . . . ?
C28 C20 C21 C27 -174.7(10) . . . . ?
C27 C22 C23 F2 176.8(10) . . . . ?
C27 C22 C23 C24 -4(2) . . . . ?
C32 N5 C24 C23 -129.6(15) . . . . ?
C35 N5 C24 C23 48(2) . . . . ?
C32 N5 C24 C25 46(2) . . . . ?
C35 N5 C24 C25 -136.7(17) . . . . ?
F2 C23 C24 N5 1(2) . . . . ?
C22 C23 C24 N5 -178.6(11) . . . . ?
F2 C23 C24 C25 -175.0(10) . . . . ?
C22 C23 C24 C25 5(2) . . . . ?
C29 O8 C25 C26 21(2) . . . . ?
C29 O8 C25 C24 -163.0(11) . . . . ?
N5 C24 C25 O8 3(2) . . . . ?
C23 C24 C25 O8 178.4(12) . . . . ?
N5 C24 C25 C26 178.9(13) . . . . ?
C23 C24 C25 C26 -5(2) . . . . ?
O8 C25 C26 N4 1(2) . . . . ?
C24 C25 C26 N4 -174.5(11) . . . . ?
O8 C25 C26 C27 179.4(12) . . . . ?
C24 C25 C26 C27 4(2) . . . . ?
C19 N4 C26 C25 -175.4(11) . . . . ?
C30 N4 C26 C25 8.8(17) . . . . ?
C19 N4 C26 C27 6.4(18) . . . . ?
C30 N4 C26 C27 -169.3(11) . . . . ?
C23 C22 C27 C26 1(2) . . . . ?
C23 C22 C27 C21 -178.0(11) . . . . ?
C25 C26 C27 C22 -1.2(19) . . . . ?
N4 C26 C27 C22 176.8(10) . . . . ?
C25 C26 C27 C21 177.9(12) . . . . ?
N4 C26 C27 C21 -4.0(18) . . . . ?
O7 C21 C27 C22 0(2) . . . . ?
C20 C21 C27 C22 177.5(11) . . . . ?
O7 C21 C27 C26 -179.1(12) . . . . ?
C20 C21 C27 C26 -1.6(17) . . . . ?
C19 C20 C28 O5 3(2) . . . . ?
C21 C20 C28 O5 -177.4(13) . . . . ?
C19 C20 C28 O6 178.8(13) . . . . ?
C21 C20 C28 O6 -1.4(18) . . . . ?
C25 O8 C29 C30 -51.2(19) . . . . ?
C19 N4 C30 C29 145.9(11) . . . . ?
C26 N4 C30 C29 -38.5(15) . . . . ?
C19 N4 C30 C31 21.1(18) . . . . ?
C26 N4 C30 C31 -163.4(12) . . . . ?
O8 C29 C30 N4 58.8(19) . . . . ?
O8 C29 C30 C31 -176(2) . . . . ?
C24 N5 C32 C33 -127.1(15) . . . . ?
C35 N5 C32 C33 55.3(18) . . . . ?
C36 N6 C33 C32 -178.4(14) . . . . ?
C34 N6 C33 C32 60.0(15) . . . . ?
N5 C32 C33 N6 -58.2(18) . . . . ?
C36 N6 C34 C35 178.2(13) . . . . ?
C33 N6 C34 C35 -60.6(17) . . . . ?
C24 N5 C35 C34 127.9(17) . . . . ?
C32 N5 C35 C34 -54.3(15) . . . . ?
N6 C34 C35 N5 57.3(17) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.76 2.53(2) 154.5 . yes
O6 H6 O7 0.82 1.75 2.52(2) 156.5 . yes
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.073
_cell_measurement_pressure       0.38

# start Validation Reply Form
_vrf_ATOM007_LH_ME_0p38          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_ME_0p38          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_ME_0p38          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_ME_0p38          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_ME_0p38          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_ME_0p38          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_ME_0p38          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_ME_0p38          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_ME_0p38          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_0p38          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell 


;
_vrf_PLAT111_LH_ME_0p38          
;
RESPONSE: The structure is chiral.

;
_vrf_PLAT721_LH_ME_0p38          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints


;
_vrf_PLAT910_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_ME_0p38          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_ME_0p38          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_ME_0p38          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_ME_0p38          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_LH_ME_1p17
_database_code_depnum_ccdc_archive 'CCDC 2481328'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_LEVO_05_H2O_221022

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.5(H2 O1)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   28.099(5)
_cell_length_b                   6.5600(4)
_cell_length_c                   18.2689(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.434(10)
_cell_angle_gamma                90
_cell_volume                     3089.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7304
_cell_measurement_theta_min      3.204
_cell_measurement_theta_max      23.382
_exptl_crystal_description       Lathe
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6681
_exptl_absorpt_correction_t_max  0.7449
_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 D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7304
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.204
_diffrn_reflns_theta_max         23.382
_diffrn_reflns_theta_full        23.382
_diffrn_measured_fraction_theta_max 0.316
_diffrn_measured_fraction_theta_full 0.316
_diffrn_reflns_Laue_measured_fraction_max 0.316
_diffrn_reflns_Laue_measured_fraction_full 0.316
_diffrn_reflns_point_group_measured_fraction_max 0.320
_diffrn_reflns_point_group_measured_fraction_full 0.320
_reflns_number_total             1447
_reflns_number_gt                1151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_max     0.326
_reflns_Friedel_fraction_full    0.326
_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       'Apex 4 suite'
_computing_cell_refinement       'Apex 4 suite'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1304P)²+3.3111P] 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_abs_structure_details 
;
 Flack x determined using 423 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1447
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1967
_refine_ls_wR_factor_gt          0.1807
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.659
_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
F1 F 0.2088(8) 0.4502(10) 0.7303(6) 0.042(2) Uiso 1 1 d D U . . .
O1 O 0.3226(10) 0.4749(13) 1.2286(8) 0.050(3) Uiso 1 1 d D U . . .
O2 O 0.3746(10) 0.4750(14) 1.1648(8) 0.051(3) Uiso 1 1 d D U . . .
H2 H 0.372348 0.486848 1.118848 0.077 Uiso 1 1 calc R U . . .
O3 O 0.3377(10) 0.4802(12) 1.0141(8) 0.041(3) Uiso 1 1 d D U . . .
O4 O 0.1032(11) 0.4552(13) 0.8757(7) 0.043(3) Uiso 1 1 d D U . . .
N1 N 0.1910(9) 0.4642(13) 1.0184(8) 0.022(3) Uiso 1 1 d D U . . .
N2 N 0.1109(9) 0.4726(14) 0.7268(8) 0.035(3) Uiso 1 1 d D U . . .
N3 N 0.0139(10) 0.6409(15) 0.6253(8) 0.042(3) Uiso 1 1 d D U . . .
C1 C 0.2346(10) 0.4637(16) 1.0859(10) 0.024(3) Uiso 1 1 d D U . . .
H1 H 0.231297 0.459655 1.134496 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2833(10) 0.4690(16) 1.0866(8) 0.025(4) Uiso 1 1 d D U . . .
C3 C 0.2936(10) 0.4745(17) 1.0161(9) 0.021(3) Uiso 1 1 d D U . . .
C4 C 0.2472(12) 0.4665(16) 0.8677(10) 0.030(4) Uiso 1 1 d D U . . .
H4 H 0.278861 0.469147 0.862877 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2027(11) 0.4610(16) 0.8005(10) 0.021(3) Uiso 1 1 d D U . . .
C6 C 0.1522(10) 0.4664(18) 0.7993(8) 0.031(4) Uiso 1 1 d D U . . .
C7 C 0.1524(11) 0.4612(19) 0.8762(9) 0.031(4) Uiso 1 1 d D U . . .
C8 C 0.1979(11) 0.4609(16) 0.9463(9) 0.021(3) Uiso 1 1 d D U . . .
C9 C 0.2466(10) 0.4681(16) 0.9433(8) 0.023(4) Uiso 1 1 d D U . . .
C10 C 0.3272(10) 0.4753(17) 1.1651(9) 0.031(4) Uiso 1 1 d D U . . .
C11 C 0.1001(10) 0.5408(16) 0.9453(8) 0.034(3) Uiso 1 1 d D U . . .
H11A H 0.065383 0.521045 0.943308 0.040 Uiso 1 1 calc R U . . .
H11B H 0.106545 0.686290 0.946505 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1389(9) 0.4444(17) 1.0202(7) 0.028(3) Uiso 1 1 d D U . . .
H12 H 0.130429 0.300075 1.022086 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1370(16) 0.554(2) 1.0911(12) 0.041(4) Uiso 1 1 d D U . . .
H13A H 0.160420 0.489845 1.139156 0.062 Uiso 1 1 calc R U . . .
H13B H 0.102401 0.548840 1.089146 0.062 Uiso 1 1 calc R U . . .
H13C H 0.147083 0.693644 1.090330 0.062 Uiso 1 1 calc R U . . .
C14 C 0.0625(9) 0.3629(18) 0.7098(10) 0.035(4) Uiso 1 1 d D U . . .
H14A H 0.065973 0.278352 0.755179 0.042 Uiso 1 1 calc R U . . .
H14B H 0.055520 0.274289 0.664165 0.042 Uiso 1 1 calc R U . . .
C15 C 0.0179(11) 0.5073(18) 0.6926(9) 0.043(4) Uiso 1 1 d D U . . .
H15A H -0.014034 0.431057 0.679189 0.051 Uiso 1 1 calc R U . . .
H15B H 0.023353 0.589173 0.739448 0.051 Uiso 1 1 calc R U . . .
C16 C 0.0625(11) 0.759(2) 0.6475(10) 0.049(4) Uiso 1 1 d D U . . .
H16A H 0.067304 0.842528 0.693673 0.059 Uiso 1 1 calc R U . . .
H16B H 0.059697 0.848898 0.603873 0.059 Uiso 1 1 calc R U . . .
C17 C 0.1093(12) 0.6220(19) 0.6665(10) 0.041(4) Uiso 1 1 d D U . . .
H17A H 0.107285 0.552316 0.618501 0.049 Uiso 1 1 calc R U . . .
H17B H 0.140743 0.703325 0.686226 0.049 Uiso 1 1 calc R U . . .
C18 C -0.0314(12) 0.776(3) 0.6036(12) 0.071(6) Uiso 1 1 d D U . . .
H18A H -0.061905 0.695494 0.593558 0.107 Uiso 1 1 calc R U . . .
H18B H -0.035410 0.851333 0.556529 0.107 Uiso 1 1 calc R U . . .
H18C H -0.026392 0.868651 0.646679 0.107 Uiso 1 1 calc R U . . .
F2 F 0.2867(8) 0.7240(11) 0.7622(6) 0.040(2) Uiso 1 1 d D U . . .
O5 O 0.1820(11) 0.6956(13) 0.2625(8) 0.048(3) Uiso 1 1 d D U . . .
O6 O 0.1295(9) 0.7081(15) 0.3241(7) 0.051(3) Uiso 1 1 d D U . . .
H6 H 0.131287 0.702253 0.369941 0.076 Uiso 1 1 calc R U . . .
O7 O 0.1633(9) 0.6779(12) 0.4749(7) 0.044(3) Uiso 1 1 d D U . . .
O8 O 0.3951(10) 0.6889(13) 0.6247(7) 0.045(3) Uiso 1 1 d D U . . .
N4 N 0.3097(9) 0.6595(13) 0.4781(8) 0.028(3) Uiso 1 1 d D U . . .
N5 N 0.3856(9) 0.7091(14) 0.7685(7) 0.035(3) Uiso 1 1 d D U . . .
N6 N 0.4835(10) 0.5851(16) 0.8791(8) 0.038(3) Uiso 1 1 d D U . . .
C19 C 0.2678(9) 0.6629(17) 0.4090(10) 0.035(4) Uiso 1 1 d D U . . .
H19 H 0.272591 0.652364 0.361652 0.042 Uiso 1 1 calc R U . . .
C20 C 0.2185(9) 0.6811(17) 0.4050(8) 0.026(4) Uiso 1 1 d D U . . .
C21 C 0.2079(9) 0.6795(17) 0.4750(8) 0.030(4) Uiso 1 1 d D U . . .
C22 C 0.2484(11) 0.6924(16) 0.6239(9) 0.034(4) Uiso 1 1 d D U . . .
H22 H 0.215864 0.693105 0.626150 0.041 Uiso 1 1 calc R U . . .
C23 C 0.2920(10) 0.7027(15) 0.6918(8) 0.022(3) Uiso 1 1 d D U . . .
C24 C 0.3430(9) 0.6990(18) 0.6969(8) 0.032(4) Uiso 1 1 d D U . . .
C25 C 0.3459(10) 0.6947(19) 0.6214(8) 0.036(4) Uiso 1 1 d D U . . .
C26 C 0.3029(9) 0.6803(15) 0.5498(9) 0.025(3) Uiso 1 1 d D U . . .
C27 C 0.2529(9) 0.6806(16) 0.5506(8) 0.027(4) Uiso 1 1 d D U . . .
C28 C 0.1763(9) 0.6961(17) 0.3248(8) 0.035(4) Uiso 1 1 d D U . . .
C29 C 0.4001(10) 0.7428(17) 0.5503(7) 0.032(3) Uiso 1 1 d D U . . .
H29A H 0.435335 0.718841 0.555459 0.038 Uiso 1 1 calc R U . . .
H29B H 0.392126 0.886026 0.538537 0.038 Uiso 1 1 calc R U . . .
C30 C 0.3632(9) 0.6146(18) 0.4844(8) 0.030(3) Uiso 1 1 d D U . . .
H30 H 0.370722 0.471069 0.499446 0.036 Uiso 1 1 calc R U . . .
C31 C 0.3708(16) 0.650(2) 0.4085(12) 0.046(4) Uiso 1 1 d D U . . .
H31A H 0.362668 0.526819 0.377240 0.069 Uiso 1 1 calc R U . . .
H31B H 0.406198 0.686725 0.420978 0.069 Uiso 1 1 calc R U . . .
H31C H 0.348311 0.757299 0.378642 0.069 Uiso 1 1 calc R U . . .
C32 C 0.4307(9) 0.8339(17) 0.7836(9) 0.032(3) Uiso 1 1 d D U . . .
H32A H 0.434152 0.932374 0.824986 0.039 Uiso 1 1 calc R U . . .
H32B H 0.426707 0.907975 0.735536 0.039 Uiso 1 1 calc R U . . .
C33 C 0.4782(11) 0.7038(19) 0.8092(9) 0.039(4) Uiso 1 1 d D U . . .
H33A H 0.476004 0.612927 0.766049 0.047 Uiso 1 1 calc R U . . .
H33B H 0.508573 0.789556 0.821439 0.047 Uiso 1 1 calc R U . . .
C34 C 0.4373(10) 0.4538(18) 0.8576(9) 0.031(3) Uiso 1 1 d D U . . .
H34A H 0.440974 0.368249 0.902775 0.037 Uiso 1 1 calc R U . . .
H34B H 0.435270 0.365382 0.813843 0.037 Uiso 1 1 calc R U . . .
C35 C 0.3884(12) 0.5734(17) 0.8336(9) 0.033(4) Uiso 1 1 d D U . . .
H35A H 0.358718 0.482501 0.816069 0.039 Uiso 1 1 calc R U . . .
H35B H 0.388309 0.652343 0.878460 0.039 Uiso 1 1 calc R U . . .
C36 C 0.5316(13) 0.466(2) 0.9078(11) 0.059(5) Uiso 1 1 d D U . . .
H36A H 0.533452 0.387897 0.864423 0.088 Uiso 1 1 calc R U . . .
H36B H 0.532035 0.374792 0.949215 0.088 Uiso 1 1 calc R U . . .
H36C H 0.560836 0.555971 0.928372 0.088 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.358(2) 0.500000 0.062(6) Uiso 1 2 d DGS . P . .
H9A H 0.000909 0.437157 0.536118 0.093 Uiso 0.5 1 d DG U P . .
H9B H 0.027408 0.290163 0.520531 0.093 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.385(2) 1.000000 0.058(5) Uiso 1 2 d DGS . P . .
H10A H -0.018533 0.445051 1.018930 0.087 Uiso 0.5 1 d DG U P . .
H10B H 0.008646 0.277844 1.026864 0.087 Uiso 0.5 1 d DG U P . .
_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 C5 1.363(11) . ?
O1 C10 1.217(12) . ?
O2 C10 1.334(14) . ?
O2 H2 0.8200 . ?
O3 C3 1.254(14) . ?
O4 C7 1.380(14) . ?
O4 C11 1.425(11) . ?
N1 C1 1.349(14) . ?
N1 C8 1.405(11) . ?
N1 C12 1.485(14) . ?
N2 C6 1.371(14) . ?
N2 C14 1.458(14) . ?
N2 C17 1.462(11) . ?
N3 C18 1.468(15) . ?
N3 C15 1.477(12) . ?
N3 C16 1.479(15) . ?
C1 C2 1.363(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.427(13) . ?
C2 C10 1.475(14) . ?
C3 C9 1.455(14) . ?
C4 C5 1.361(15) . ?
C4 C9 1.387(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(14) . ?
C6 C7 1.403(13) . ?
C7 C8 1.404(14) . ?
C8 C9 1.392(14) . ?
C11 C12 1.507(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.501(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.501(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.514(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.360(11) . ?
O5 C28 1.210(12) . ?
O6 C28 1.313(14) . ?
O6 H6 0.8200 . ?
O7 C21 1.251(14) . ?
O8 C25 1.360(14) . ?
O8 C29 1.463(11) . ?
N4 C19 1.342(14) . ?
N4 C26 1.404(12) . ?
N4 C30 1.489(14) . ?
N5 C24 1.379(14) . ?
N5 C32 1.439(14) . ?
N5 C35 1.463(11) . ?
N6 C33 1.453(11) . ?
N6 C36 1.468(15) . ?
N6 C34 1.473(14) . ?
C19 C20 1.363(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.425(13) . ?
C20 C28 1.476(14) . ?
C21 C27 1.455(14) . ?
C22 C23 1.356(15) . ?
C22 C27 1.396(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(14) . ?
C24 C25 1.416(13) . ?
C25 C26 1.387(14) . ?
C26 C27 1.412(14) . ?
C29 C30 1.496(14) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.503(12) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.495(15) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.490(15) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8338 . ?
O9 H9B 0.8364 . ?
O9 H9A 0.8(3) 2_556 ?
O9 H9B 0.8(4) 2_556 ?
O10 H10A 0.8317 . ?
O10 H10B 0.8335 . ?
O10 H10A 0.8(3) 2_557 ?
O10 H10B 0.8(3) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 113.5(18) . . ?
C1 N1 C8 116.3(17) . . ?
C1 N1 C12 121.7(11) . . ?
C8 N1 C12 121.6(17) . . ?
C6 N2 C14 123.4(12) . . ?
C6 N2 C17 120.6(17) . . ?
C14 N2 C17 115.1(17) . . ?
C18 N3 C15 110.7(15) . . ?
C18 N3 C16 111.4(12) . . ?
C15 N3 C16 109.0(17) . . ?
N1 C1 C2 123.5(13) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 123.7(17) . . ?
C1 C2 C10 117.3(13) . . ?
C3 C2 C10 119.0(18) . . ?
O3 C3 C2 125.7(18) . . ?
O3 C3 C9 121.5(13) . . ?
C2 C3 C9 112.8(16) . . ?
C5 C4 C9 121.9(19) . . ?
C5 C4 H4 119.0 . . ?
C9 C4 H4 119.0 . . ?
C4 C5 F1 115.9(17) . . ?
C4 C5 C6 124.8(12) . . ?
F1 C5 C6 119.3(19) . . ?
N2 C6 C7 129.4(19) . . ?
N2 C6 C5 118.3(14) . . ?
C7 C6 C5 112.3(16) . . ?
O4 C7 C6 112.8(17) . . ?
O4 C7 C8 123.6(13) . . ?
C6 C7 C8 123.6(18) . . ?
C9 C8 C7 121.2(12) . . ?
C9 C8 N1 122.7(17) . . ?
C7 C8 N1 116.1(18) . . ?
C4 C9 C8 116.0(18) . . ?
C4 C9 C3 123.0(19) . . ?
C8 C9 C3 121.0(11) . . ?
O1 C10 O2 119.3(19) . . ?
O1 C10 C2 124(2) . . ?
O2 C10 C2 116.5(14) . . ?
O4 C11 C12 111.5(14) . . ?
O4 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O4 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C13 110.5(19) . . ?
N1 C12 C11 107.9(13) . . ?
C13 C12 C11 108.8(16) . . ?
N1 C12 H12 109.9 . . ?
C13 C12 H12 109.9 . . ?
C11 C12 H12 109.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.3(12) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 109.3(15) . . ?
N3 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
N3 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N3 C16 C17 112.1(13) . . ?
N3 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 109.4(16) . . ?
N2 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 115.0(17) . . ?
C19 N4 C26 118.8(17) . . ?
C19 N4 C30 123.9(11) . . ?
C26 N4 C30 117.1(16) . . ?
C24 N5 C32 125.1(12) . . ?
C24 N5 C35 119.1(16) . . ?
C32 N5 C35 115.6(16) . . ?
C33 N6 C36 110.9(15) . . ?
C33 N6 C34 108.0(16) . . ?
C36 N6 C34 111.8(11) . . ?
N4 C19 C20 123.1(15) . . ?
N4 C19 H19 118.4 . . ?
C20 C19 H19 118.4 . . ?
C19 C20 C21 121.4(17) . . ?
C19 C20 C28 117.2(13) . . ?
C21 C20 C28 121.3(17) . . ?
O7 C21 C20 124.4(17) . . ?
O7 C21 C27 119.5(13) . . ?
C20 C21 C27 116.1(16) . . ?
C23 C22 C27 119.0(18) . . ?
C23 C22 H22 120.5 . . ?
C27 C22 H22 120.5 . . ?
C22 C23 F2 118.0(17) . . ?
C22 C23 C24 126.3(11) . . ?
F2 C23 C24 115.7(18) . . ?
N5 C24 C23 122.9(13) . . ?
N5 C24 C25 124.0(17) . . ?
C23 C24 C25 113.0(15) . . ?
O8 C25 C26 122.0(13) . . ?
O8 C25 C24 114.2(16) . . ?
C26 C25 C24 123.6(17) . . ?
C25 C26 N4 119.6(17) . . ?
C25 C26 C27 119.3(12) . . ?
N4 C26 C27 121.1(16) . . ?
C22 C27 C26 118.7(17) . . ?
C22 C27 C21 122.4(18) . . ?
C26 C27 C21 118.9(12) . . ?
O5 C28 O6 119.8(19) . . ?
O5 C28 C20 125.4(19) . . ?
O6 C28 C20 114.8(14) . . ?
O8 C29 C30 108.7(12) . . ?
O8 C29 H29A 110.0 . . ?
C30 C29 H29A 110.0 . . ?
O8 C29 H29B 110.0 . . ?
C30 C29 H29B 110.0 . . ?
H29A C29 H29B 108.3 . . ?
N4 C30 C29 107.8(13) . . ?
N4 C30 C31 114.1(19) . . ?
C29 C30 C31 110.5(14) . . ?
N4 C30 H30 108.1 . . ?
C29 C30 H30 108.1 . . ?
C31 C30 H30 108.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 110.2(12) . . ?
N5 C32 H32A 109.6 . . ?
C33 C32 H32A 109.6 . . ?
N5 C32 H32B 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N6 C33 C32 110.3(16) . . ?
N6 C33 H33A 109.6 . . ?
C32 C33 H33A 109.6 . . ?
N6 C33 H33B 109.6 . . ?
C32 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
N6 C34 C35 112.5(12) . . ?
N6 C34 H34A 109.1 . . ?
C35 C34 H34A 109.1 . . ?
N6 C34 H34B 109.1 . . ?
C35 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
N5 C35 C34 107.7(16) . . ?
N5 C35 H35A 110.2 . . ?
C34 C35 H35A 110.2 . . ?
N5 C35 H35B 110.2 . . ?
C34 C35 H35B 110.2 . . ?
H35A C35 H35B 108.5 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 104.1 . . ?
H9A O9 H9A 102.5 . 2_556 ?
H9B O9 H9A 114.8 . 2_556 ?
H9A O9 H9B 114.8 . 2_556 ?
H9B O9 H9B 116.2 . 2_556 ?
H9A O9 H9B 104.1 2_556 2_556 ?
H10A O10 H10B 103.9 . . ?
H10A O10 H10A 123.0 . 2_557 ?
H10B O10 H10A 124.2 . 2_557 ?
H10A O10 H10B 124.2 . 2_557 ?
H10B O10 H10B 65.8 . 2_557 ?
H10A O10 H10B 103.9 2_557 2_557 ?
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
C8 N1 C1 C2 2.8(17) . . . . ?
C12 N1 C1 C2 175.8(10) . . . . ?
N1 C1 C2 C3 -0.3(19) . . . . ?
N1 C1 C2 C10 177.8(10) . . . . ?
C1 C2 C3 O3 179.7(12) . . . . ?
C10 C2 C3 O3 1.6(17) . . . . ?
C1 C2 C3 C9 -1.6(16) . . . . ?
C10 C2 C3 C9 -179.7(9) . . . . ?
C9 C4 C5 F1 -177.0(9) . . . . ?
C9 C4 C5 C6 3.2(19) . . . . ?
C14 N2 C6 C7 -37(2) . . . . ?
C17 N2 C6 C7 130.9(16) . . . . ?
C14 N2 C6 C5 141.7(12) . . . . ?
C17 N2 C6 C5 -50.3(19) . . . . ?
C4 C5 C6 N2 176.0(11) . . . . ?
F1 C5 C6 N2 -3.8(16) . . . . ?
C4 C5 C6 C7 -4.9(17) . . . . ?
F1 C5 C6 C7 175.3(9) . . . . ?
C11 O4 C7 C6 -152.9(10) . . . . ?
C11 O4 C7 C8 27.4(17) . . . . ?
N2 C6 C7 O4 2(2) . . . . ?
C5 C6 C7 O4 -176.7(11) . . . . ?
N2 C6 C7 C8 -178.1(12) . . . . ?
C5 C6 C7 C8 3.0(18) . . . . ?
O4 C7 C8 C9 -179.7(10) . . . . ?
C6 C7 C8 C9 0.6(19) . . . . ?
O4 C7 C8 N1 -3.0(18) . . . . ?
C6 C7 C8 N1 177.4(10) . . . . ?
C1 N1 C8 C9 -3.4(15) . . . . ?
C12 N1 C8 C9 -176.4(10) . . . . ?
C1 N1 C8 C7 179.9(10) . . . . ?
C12 N1 C8 C7 6.9(15) . . . . ?
C5 C4 C9 C8 0.9(16) . . . . ?
C5 C4 C9 C3 -179.8(10) . . . . ?
C7 C8 C9 C4 -2.7(17) . . . . ?
N1 C8 C9 C4 -179.2(9) . . . . ?
C7 C8 C9 C3 178.0(10) . . . . ?
N1 C8 C9 C3 1.5(16) . . . . ?
O3 C3 C9 C4 0.4(17) . . . . ?
C2 C3 C9 C4 -178.3(10) . . . . ?
O3 C3 C9 C8 179.7(11) . . . . ?
C2 C3 C9 C8 1.0(14) . . . . ?
C1 C2 C10 O1 0.5(17) . . . . ?
C3 C2 C10 O1 178.7(10) . . . . ?
C1 C2 C10 O2 178.3(11) . . . . ?
C3 C2 C10 O2 -3.5(15) . . . . ?
C7 O4 C11 C12 -54.0(17) . . . . ?
C1 N1 C12 C13 36.4(16) . . . . ?
C8 N1 C12 C13 -151.0(12) . . . . ?
C1 N1 C12 C11 155.2(9) . . . . ?
C8 N1 C12 C11 -32.2(13) . . . . ?
O4 C11 C12 N1 54.9(17) . . . . ?
O4 C11 C12 C13 174.8(19) . . . . ?
C6 N2 C14 C15 115.6(14) . . . . ?
C17 N2 C14 C15 -53.1(17) . . . . ?
C18 N3 C15 C14 176.5(14) . . . . ?
C16 N3 C15 C14 -60.6(15) . . . . ?
N2 C14 C15 N3 57.0(18) . . . . ?
C18 N3 C16 C17 -177.5(12) . . . . ?
C15 N3 C16 C17 60.1(15) . . . . ?
C6 N2 C17 C16 -119.0(17) . . . . ?
C14 N2 C17 C16 50.0(17) . . . . ?
N3 C16 C17 N2 -53.4(18) . . . . ?
C26 N4 C19 C20 -1.5(18) . . . . ?
C30 N4 C19 C20 172.3(11) . . . . ?
N4 C19 C20 C21 -6(2) . . . . ?
N4 C19 C20 C28 176.1(9) . . . . ?
C19 C20 C21 O7 -173.6(13) . . . . ?
C28 C20 C21 O7 4.5(18) . . . . ?
C19 C20 C21 C27 6.7(17) . . . . ?
C28 C20 C21 C27 -175.3(9) . . . . ?
C27 C22 C23 F2 176.9(9) . . . . ?
C27 C22 C23 C24 -1.3(19) . . . . ?
C32 N5 C24 C23 -135.6(13) . . . . ?
C35 N5 C24 C23 49.4(19) . . . . ?
C32 N5 C24 C25 41.0(19) . . . . ?
C35 N5 C24 C25 -134.1(15) . . . . ?
C22 C23 C24 N5 -179.6(10) . . . . ?
F2 C23 C24 N5 2.1(18) . . . . ?
C22 C23 C24 C25 3.5(18) . . . . ?
F2 C23 C24 C25 -174.7(9) . . . . ?
C29 O8 C25 C26 21.9(17) . . . . ?
C29 O8 C25 C24 -163.2(9) . . . . ?
N5 C24 C25 O8 3.8(18) . . . . ?
C23 C24 C25 O8 -179.3(11) . . . . ?
N5 C24 C25 C26 178.6(12) . . . . ?
C23 C24 C25 C26 -4.5(17) . . . . ?
O8 C25 C26 N4 -0.2(17) . . . . ?
C24 C25 C26 N4 -174.6(10) . . . . ?
O8 C25 C26 C27 177.9(11) . . . . ?
C24 C25 C26 C27 3.5(17) . . . . ?
C19 N4 C26 C25 -174.5(10) . . . . ?
C30 N4 C26 C25 11.3(14) . . . . ?
C19 N4 C26 C27 7.5(15) . . . . ?
C30 N4 C26 C27 -166.7(10) . . . . ?
C23 C22 C27 C26 -0.1(16) . . . . ?
C23 C22 C27 C21 -176.8(10) . . . . ?
C25 C26 C27 C22 -0.9(16) . . . . ?
N4 C26 C27 C22 177.1(9) . . . . ?
C25 C26 C27 C21 175.8(10) . . . . ?
N4 C26 C27 C21 -6.1(16) . . . . ?
O7 C21 C27 C22 -4.0(18) . . . . ?
C20 C21 C27 C22 175.8(9) . . . . ?
O7 C21 C27 C26 179.4(10) . . . . ?
C20 C21 C27 C26 -0.8(16) . . . . ?
C19 C20 C28 O5 -0.8(18) . . . . ?
C21 C20 C28 O5 -178.9(11) . . . . ?
C19 C20 C28 O6 178.3(12) . . . . ?
C21 C20 C28 O6 0.2(16) . . . . ?
C25 O8 C29 C30 -52.6(17) . . . . ?
C19 N4 C30 C29 144.8(10) . . . . ?
C26 N4 C30 C29 -41.4(12) . . . . ?
C19 N4 C30 C31 21.7(16) . . . . ?
C26 N4 C30 C31 -164.4(10) . . . . ?
O8 C29 C30 N4 60.5(16) . . . . ?
O8 C29 C30 C31 -174.2(19) . . . . ?
C24 N5 C32 C33 -121.6(13) . . . . ?
C35 N5 C32 C33 53.6(16) . . . . ?
C36 N6 C33 C32 -176.7(12) . . . . ?
C34 N6 C33 C32 60.5(13) . . . . ?
N5 C32 C33 N6 -56.8(16) . . . . ?
C33 N6 C34 C35 -61.7(15) . . . . ?
C36 N6 C34 C35 176.1(11) . . . . ?
C24 N5 C35 C34 123.4(15) . . . . ?
C32 N5 C35 C34 -52.2(14) . . . . ?
N6 C34 C35 N5 55.6(15) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.77 2.526(18) 152.9 . yes
O6 H6 O7 0.82 1.77 2.540(16) 155.2 . yes
O9 H9A N3 0.83 2.02 2.852(15) 171.5 . yes
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_cell_measurement_pressure       1.17

# start Validation Reply Form
_vrf_ATOM007_LH_ME_1p17          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_ME_1p17          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_ME_1p17          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_ME_1p17          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_ME_1p17          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_ME_1p17          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_ME_1p17          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_ME_1p17          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_ME_1p17          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_1p17          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell 

;
_vrf_PLAT111_LH_ME_1p17          
;
RESPONSE: The structure is chiral.
;
_vrf_PLAT721_LH_ME_1p17          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints

;
_vrf_PLAT910_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_ME_1p17          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_ME_1p17          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_ME_1p17          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_ME_1p17          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_LH_ME_1p68
_database_code_depnum_ccdc_archive 'CCDC 2481329'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_LEVO_05_H2O_241022

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.5(H2 O1)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   27.928(5)
_cell_length_b                   6.4713(4)
_cell_length_c                   18.1487(13)
_cell_angle_alpha                90
_cell_angle_beta                 113.447(12)
_cell_angle_gamma                90
_cell_volume                     3009.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7133
_cell_measurement_theta_min      3.247
_cell_measurement_theta_max      23.279
_exptl_crystal_description       Lathe
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6681
_exptl_absorpt_correction_t_max  0.7449
_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 D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7133
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.247
_diffrn_reflns_theta_max         23.279
_diffrn_reflns_theta_full        23.279
_diffrn_measured_fraction_theta_max 0.317
_diffrn_measured_fraction_theta_full 0.317
_diffrn_reflns_Laue_measured_fraction_max 0.317
_diffrn_reflns_Laue_measured_fraction_full 0.317
_diffrn_reflns_point_group_measured_fraction_max 0.324
_diffrn_reflns_point_group_measured_fraction_full 0.324
_reflns_number_total             1399
_reflns_number_gt                1128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_max     0.333
_reflns_Friedel_fraction_full    0.333
_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       'Apex 4 suite'
_computing_cell_refinement       'Apex 4 suite'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1226P)²+2.4509P] 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_abs_structure_details 
;
 Flack x determined using 406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1399
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1775
_refine_ls_wR_factor_gt          0.1622
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.723
_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
F1 F 0.2096(8) 0.4467(10) 0.7285(6) 0.037(2) Uiso 1 1 d D U . . .
O1 O 0.3228(10) 0.4706(12) 1.2302(8) 0.043(3) Uiso 1 1 d D U . . .
O2 O 0.3752(9) 0.4698(13) 1.1664(7) 0.047(3) Uiso 1 1 d D U . . .
H2 H 0.372916 0.467315 1.119976 0.071 Uiso 1 1 calc R U . . .
O3 O 0.3386(10) 0.4770(12) 1.0148(7) 0.039(3) Uiso 1 1 d D U . . .
O4 O 0.1026(10) 0.4500(12) 0.8737(7) 0.038(3) Uiso 1 1 d D U . . .
N1 N 0.1907(9) 0.4613(13) 1.0179(8) 0.025(3) Uiso 1 1 d D U . . .
N2 N 0.1107(9) 0.4675(14) 0.7249(8) 0.033(3) Uiso 1 1 d D U . . .
N3 N 0.0138(9) 0.6419(15) 0.6254(8) 0.038(3) Uiso 1 1 d D U . . .
C1 C 0.2343(9) 0.4619(16) 1.0855(9) 0.022(3) Uiso 1 1 d D U . . .
H1 H 0.230761 0.458676 1.134360 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2833(9) 0.4668(15) 1.0869(8) 0.023(4) Uiso 1 1 d D U . . .
C3 C 0.2942(9) 0.4706(17) 1.0165(8) 0.020(3) Uiso 1 1 d D U . . .
C4 C 0.2476(11) 0.4635(15) 0.8664(9) 0.028(3) Uiso 1 1 d D U . . .
H4 H 0.279475 0.466864 0.861544 0.034 Uiso 1 1 calc R U . . .
C5 C 0.2028(10) 0.4570(16) 0.7989(9) 0.020(3) Uiso 1 1 d D U . . .
C6 C 0.1522(10) 0.4623(17) 0.7976(8) 0.027(3) Uiso 1 1 d D U . . .
C7 C 0.1519(10) 0.4567(18) 0.8745(8) 0.028(4) Uiso 1 1 d D U . . .
C8 C 0.1975(10) 0.4579(15) 0.9453(8) 0.019(3) Uiso 1 1 d D U . . .
C9 C 0.2469(10) 0.4653(16) 0.9430(8) 0.022(3) Uiso 1 1 d D U . . .
C10 C 0.3275(9) 0.4690(16) 1.1667(8) 0.026(3) Uiso 1 1 d D U . . .
C11 C 0.0983(10) 0.5365(16) 0.9430(8) 0.034(3) Uiso 1 1 d D U . . .
H11A H 0.063441 0.512169 0.940619 0.040 Uiso 1 1 calc R U . . .
H11B H 0.103701 0.684708 0.943686 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1379(9) 0.4424(17) 1.0190(7) 0.026(3) Uiso 1 1 d D U . . .
H12 H 0.129717 0.296108 1.021630 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1355(14) 0.554(2) 1.0900(11) 0.040(4) Uiso 1 1 d D U . . .
H13A H 0.153143 0.474580 1.137828 0.060 Uiso 1 1 calc R U . . .
H13B H 0.099674 0.573180 1.082133 0.060 Uiso 1 1 calc R U . . .
H13C H 0.152069 0.686702 1.095478 0.060 Uiso 1 1 calc R U . . .
C14 C 0.0619(9) 0.3575(17) 0.7080(9) 0.029(3) Uiso 1 1 d D U . . .
H14A H 0.065586 0.269721 0.753309 0.035 Uiso 1 1 calc R U . . .
H14B H 0.054246 0.269659 0.661388 0.035 Uiso 1 1 calc R U . . .
C15 C 0.0173(10) 0.5048(17) 0.6926(9) 0.038(4) Uiso 1 1 d D U . . .
H15A H -0.015001 0.428697 0.678862 0.045 Uiso 1 1 calc R U . . .
H15B H 0.023282 0.586050 0.740340 0.045 Uiso 1 1 calc R U . . .
C16 C 0.0629(10) 0.759(2) 0.6464(9) 0.041(4) Uiso 1 1 d D U . . .
H16A H 0.068785 0.843860 0.693383 0.050 Uiso 1 1 calc R U . . .
H16B H 0.059755 0.850965 0.602385 0.050 Uiso 1 1 calc R U . . .
C17 C 0.1091(11) 0.6176(18) 0.6635(9) 0.037(4) Uiso 1 1 d D U . . .
H17A H 0.105881 0.546072 0.614746 0.044 Uiso 1 1 calc R U . . .
H17B H 0.141147 0.697489 0.682332 0.044 Uiso 1 1 calc R U . . .
C18 C -0.0311(11) 0.782(2) 0.6039(11) 0.061(5) Uiso 1 1 d D U . . .
H18A H -0.062457 0.702585 0.590533 0.092 Uiso 1 1 calc R U . . .
H18B H -0.033546 0.864271 0.558519 0.092 Uiso 1 1 calc R U . . .
H18C H -0.026567 0.870692 0.648578 0.092 Uiso 1 1 calc R U . . .
F2 F 0.2867(8) 0.7289(10) 0.7640(6) 0.038(2) Uiso 1 1 d D U . . .
O5 O 0.1832(10) 0.7005(13) 0.2614(8) 0.045(3) Uiso 1 1 d D U . . .
O6 O 0.1300(9) 0.7148(14) 0.3225(7) 0.045(3) Uiso 1 1 d D U . . .
H6 H 0.131602 0.706964 0.368545 0.067 Uiso 1 1 calc R U . . .
O7 O 0.1624(8) 0.6784(12) 0.4733(7) 0.039(3) Uiso 1 1 d D U . . .
O8 O 0.3951(10) 0.6955(12) 0.6252(7) 0.041(3) Uiso 1 1 d D U . . .
N4 N 0.3105(8) 0.6622(13) 0.4789(8) 0.029(3) Uiso 1 1 d D U . . .
N5 N 0.3841(9) 0.7157(14) 0.7694(7) 0.029(3) Uiso 1 1 d D U . . .
N6 N 0.4844(10) 0.5848(15) 0.8806(8) 0.033(3) Uiso 1 1 d D U . . .
C19 C 0.2689(9) 0.6669(16) 0.4094(9) 0.027(4) Uiso 1 1 d D U . . .
H19 H 0.274053 0.657587 0.361890 0.033 Uiso 1 1 calc R U . . .
C20 C 0.2194(9) 0.6845(16) 0.4047(8) 0.023(3) Uiso 1 1 d D U . . .
C21 C 0.2071(8) 0.6811(16) 0.4733(8) 0.026(4) Uiso 1 1 d D U . . .
C22 C 0.2468(10) 0.6955(15) 0.6236(9) 0.028(4) Uiso 1 1 d D U . . .
H22 H 0.213965 0.696358 0.625464 0.034 Uiso 1 1 calc R U . . .
C23 C 0.2906(10) 0.7059(16) 0.6924(8) 0.023(3) Uiso 1 1 d D U . . .
C24 C 0.3417(9) 0.7042(17) 0.6973(7) 0.025(3) Uiso 1 1 d D U . . .
C25 C 0.3454(10) 0.6990(18) 0.6215(8) 0.031(4) Uiso 1 1 d D U . . .
C26 C 0.3019(9) 0.6829(14) 0.5493(9) 0.024(3) Uiso 1 1 d D U . . .
C27 C 0.2515(9) 0.6836(15) 0.5502(8) 0.022(4) Uiso 1 1 d D U . . .
C28 C 0.1772(9) 0.6992(17) 0.3236(8) 0.030(4) Uiso 1 1 d D U . . .
C29 C 0.4015(10) 0.7456(17) 0.5514(7) 0.032(3) Uiso 1 1 d D U . . .
H29A H 0.437089 0.717928 0.557701 0.039 Uiso 1 1 calc R U . . .
H29B H 0.394170 0.890805 0.538553 0.039 Uiso 1 1 calc R U . . .
C30 C 0.3641(9) 0.6139(17) 0.4854(8) 0.027(3) Uiso 1 1 d D U . . .
H30 H 0.371439 0.468822 0.501403 0.033 Uiso 1 1 calc R U . . .
C31 C 0.3707(15) 0.644(2) 0.4079(11) 0.042(4) Uiso 1 1 d D U . . .
H31A H 0.362689 0.516769 0.378023 0.063 Uiso 1 1 calc R U . . .
H31B H 0.406046 0.682692 0.419211 0.063 Uiso 1 1 calc R U . . .
H31C H 0.347456 0.750218 0.377050 0.063 Uiso 1 1 calc R U . . .
C32 C 0.4301(9) 0.8402(18) 0.7849(9) 0.032(3) Uiso 1 1 d D U . . .
H32A H 0.434174 0.938805 0.827187 0.038 Uiso 1 1 calc R U . . .
H32B H 0.426133 0.916743 0.736826 0.038 Uiso 1 1 calc R U . . .
C33 C 0.4778(10) 0.7054(18) 0.8095(8) 0.033(3) Uiso 1 1 d D U . . .
H33A H 0.474561 0.612830 0.765772 0.040 Uiso 1 1 calc R U . . .
H33B H 0.508345 0.791085 0.820606 0.040 Uiso 1 1 calc R U . . .
C34 C 0.4384(10) 0.4526(18) 0.8598(9) 0.029(3) Uiso 1 1 d D U . . .
H34A H 0.442134 0.366540 0.905566 0.034 Uiso 1 1 calc R U . . .
H34B H 0.435930 0.362523 0.815775 0.034 Uiso 1 1 calc R U . . .
C35 C 0.3896(11) 0.5763(17) 0.8362(9) 0.030(3) Uiso 1 1 d D U . . .
H35A H 0.359731 0.484184 0.820196 0.037 Uiso 1 1 calc R U . . .
H35B H 0.390363 0.656596 0.881837 0.037 Uiso 1 1 calc R U . . .
C36 C 0.5322(12) 0.462(2) 0.9081(11) 0.057(5) Uiso 1 1 d D U . . .
H36A H 0.534085 0.387935 0.863568 0.085 Uiso 1 1 calc R U . . .
H36B H 0.532211 0.366430 0.948418 0.085 Uiso 1 1 calc R U . . .
H36C H 0.561859 0.552469 0.930393 0.085 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.355(2) 0.500000 0.051(4) Uiso 1 2 d DGS . P . .
H9A H -0.002384 0.449930 0.528850 0.076 Uiso 0.5 1 d DG U P . .
H9B H 0.013826 0.259936 0.532021 0.076 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.390(2) 1.000000 0.052(5) Uiso 1 2 d DGS . P . .
H10A H -0.023320 0.463699 1.002738 0.078 Uiso 0.5 1 d DG U P . .
H10B H 0.000348 0.289245 1.028044 0.078 Uiso 0.5 1 d DG U P . .
_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 C5 1.365(11) . ?
O1 C10 1.210(12) . ?
O2 C10 1.335(14) . ?
O2 H2 0.8200 . ?
O3 C3 1.254(14) . ?
O4 C7 1.372(14) . ?
O4 C11 1.425(11) . ?
N1 C1 1.341(14) . ?
N1 C8 1.404(11) . ?
N1 C12 1.488(14) . ?
N2 C6 1.368(14) . ?
N2 C14 1.458(15) . ?
N2 C17 1.467(11) . ?
N3 C18 1.468(15) . ?
N3 C15 1.478(11) . ?
N3 C16 1.481(15) . ?
C1 C2 1.360(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.427(13) . ?
C2 C10 1.482(14) . ?
C3 C9 1.457(14) . ?
C4 C5 1.359(15) . ?
C4 C9 1.397(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(14) . ?
C6 C7 1.399(12) . ?
C7 C8 1.405(14) . ?
C8 C9 1.396(14) . ?
C11 C12 1.512(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.503(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.502(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.511(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.355(11) . ?
O5 C28 1.205(12) . ?
O6 C28 1.314(14) . ?
O6 H6 0.8200 . ?
O7 C21 1.250(14) . ?
O8 C25 1.365(14) . ?
O8 C29 1.457(11) . ?
N4 C19 1.333(14) . ?
N4 C26 1.399(12) . ?
N4 C30 1.485(14) . ?
N5 C24 1.373(14) . ?
N5 C32 1.446(14) . ?
N5 C35 1.470(11) . ?
N6 C33 1.455(11) . ?
N6 C36 1.460(15) . ?
N6 C34 1.462(14) . ?
C19 C20 1.356(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.418(13) . ?
C20 C28 1.477(14) . ?
C21 C27 1.452(14) . ?
C22 C23 1.359(15) . ?
C22 C27 1.393(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.394(14) . ?
C24 C25 1.419(13) . ?
C25 C26 1.392(14) . ?
C26 C27 1.412(14) . ?
C29 C30 1.502(14) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.501(12) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.503(15) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.489(15) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8261 . ?
O9 H9B 0.8295 . ?
O9 H9A 0.8(3) 2_556 ?
O9 H9B 0.8(3) 2_556 ?
O10 H10A 0.8252 . ?
O10 H10B 0.8239 . ?
O10 H10A 0.8(3) 2_557 ?
O10 H10B 0.8(2) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 114.5(17) . . ?
C1 N1 C8 116.5(17) . . ?
C1 N1 C12 122.1(11) . . ?
C8 N1 C12 121.1(17) . . ?
C6 N2 C14 123.7(11) . . ?
C6 N2 C17 120.4(16) . . ?
C14 N2 C17 114.9(16) . . ?
C18 N3 C15 111.1(14) . . ?
C18 N3 C16 110.9(12) . . ?
C15 N3 C16 110.2(16) . . ?
N1 C1 C2 123.9(13) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 123.7(16) . . ?
C1 C2 C10 117.3(12) . . ?
C3 C2 C10 119.0(17) . . ?
O3 C3 C2 126.0(17) . . ?
O3 C3 C9 121.6(12) . . ?
C2 C3 C9 112.4(15) . . ?
C5 C4 C9 121.7(18) . . ?
C5 C4 H4 119.2 . . ?
C9 C4 H4 119.2 . . ?
C4 C5 F1 115.2(16) . . ?
C4 C5 C6 124.9(12) . . ?
F1 C5 C6 119.9(18) . . ?
N2 C6 C7 128.5(18) . . ?
N2 C6 C5 118.6(12) . . ?
C7 C6 C5 112.8(16) . . ?
O4 C7 C6 113.3(16) . . ?
O4 C7 C8 123.4(12) . . ?
C6 C7 C8 123.3(17) . . ?
C9 C8 N1 122.1(17) . . ?
C9 C8 C7 121.3(11) . . ?
N1 C8 C7 116.5(17) . . ?
C8 C9 C4 115.7(17) . . ?
C8 C9 C3 121.3(11) . . ?
C4 C9 C3 123.0(18) . . ?
O1 C10 O2 119.3(18) . . ?
O1 C10 C2 124.6(18) . . ?
O2 C10 C2 116.1(13) . . ?
O4 C11 C12 111.0(13) . . ?
O4 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
O4 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C13 110.8(18) . . ?
N1 C12 C11 108.9(13) . . ?
C13 C12 C11 108.8(15) . . ?
N1 C12 H12 109.4 . . ?
C13 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.4(11) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 108.3(14) . . ?
N3 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
N3 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
N3 C16 C17 111.7(12) . . ?
N3 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 108.8(15) . . ?
N2 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
N2 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 116.5(16) . . ?
C19 N4 C26 117.4(17) . . ?
C19 N4 C30 123.5(11) . . ?
C26 N4 C30 118.8(16) . . ?
C24 N5 C32 125.2(11) . . ?
C24 N5 C35 121.3(15) . . ?
C32 N5 C35 112.9(16) . . ?
C33 N6 C36 111.7(14) . . ?
C33 N6 C34 107.3(15) . . ?
C36 N6 C34 111.2(11) . . ?
N4 C19 C20 123.0(14) . . ?
N4 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C19 C20 C21 122.7(17) . . ?
C19 C20 C28 117.2(13) . . ?
C21 C20 C28 120.0(16) . . ?
O7 C21 C20 126.3(16) . . ?
O7 C21 C27 118.2(12) . . ?
C20 C21 C27 115.5(16) . . ?
C23 C22 C27 119.1(17) . . ?
C23 C22 H22 120.4 . . ?
C27 C22 H22 120.4 . . ?
F2 C23 C22 119.9(17) . . ?
F2 C23 C24 114.2(17) . . ?
C22 C23 C24 125.8(11) . . ?
N5 C24 C23 122.2(12) . . ?
N5 C24 C25 123.9(17) . . ?
C23 C24 C25 113.8(15) . . ?
O8 C25 C26 122.4(12) . . ?
O8 C25 C24 114.6(16) . . ?
C26 C25 C24 122.8(17) . . ?
C25 C26 N4 117.7(16) . . ?
C25 C26 C27 119.3(11) . . ?
N4 C26 C27 123.0(16) . . ?
C22 C27 C26 119.1(16) . . ?
C22 C27 C21 123.3(17) . . ?
C26 C27 C21 117.6(11) . . ?
O5 C28 O6 119.8(18) . . ?
O5 C28 C20 125.5(18) . . ?
O6 C28 C20 114.7(13) . . ?
O8 C29 C30 107.8(12) . . ?
O8 C29 H29A 110.1 . . ?
C30 C29 H29A 110.1 . . ?
O8 C29 H29B 110.2 . . ?
C30 C29 H29B 110.2 . . ?
H29A C29 H29B 108.5 . . ?
N4 C30 C31 113.1(18) . . ?
N4 C30 C29 107.7(12) . . ?
C31 C30 C29 111.6(14) . . ?
N4 C30 H30 108.1 . . ?
C31 C30 H30 108.1 . . ?
C29 C30 H30 108.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 110.3(11) . . ?
N5 C32 H32A 109.6 . . ?
C33 C32 H32A 109.6 . . ?
N5 C32 H32B 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N6 C33 C32 111.1(15) . . ?
N6 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
N6 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
N6 C34 C35 111.7(11) . . ?
N6 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
N6 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
N5 C35 C34 110.5(16) . . ?
N5 C35 H35A 109.6 . . ?
C34 C35 H35A 109.6 . . ?
N5 C35 H35B 109.6 . . ?
C34 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 103.9 . . ?
H9A O9 H9A 84.1 . 2_556 ?
H9B O9 H9A 149.7 . 2_556 ?
H9A O9 H9B 149.7 . 2_556 ?
H9B O9 H9B 84.0 . 2_556 ?
H9A O9 H9B 103.9 2_556 2_556 ?
H10A O10 H10B 103.7 . . ?
H10A O10 H10A 109.2 . 2_557 ?
H10B O10 H10A 132.8 . 2_557 ?
H10A O10 H10B 132.8 . 2_557 ?
H10B O10 H10B 75.6 . 2_557 ?
H10A O10 H10B 103.7 2_557 2_557 ?
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
C8 N1 C1 C2 2.5(17) . . . . ?
C12 N1 C1 C2 176.0(10) . . . . ?
N1 C1 C2 C3 -0.4(19) . . . . ?
N1 C1 C2 C10 179.3(9) . . . . ?
C1 C2 C3 O3 179.3(11) . . . . ?
C10 C2 C3 O3 -0.4(17) . . . . ?
C1 C2 C3 C9 -0.9(16) . . . . ?
C10 C2 C3 C9 179.3(9) . . . . ?
C9 C4 C5 F1 -177.2(8) . . . . ?
C9 C4 C5 C6 3.5(18) . . . . ?
C14 N2 C6 C7 -36.3(19) . . . . ?
C17 N2 C6 C7 131.8(15) . . . . ?
C14 N2 C6 C5 142.1(12) . . . . ?
C17 N2 C6 C5 -49.8(18) . . . . ?
C4 C5 C6 N2 176.0(10) . . . . ?
F1 C5 C6 N2 -3.3(16) . . . . ?
C4 C5 C6 C7 -5.3(17) . . . . ?
F1 C5 C6 C7 175.4(9) . . . . ?
C11 O4 C7 C6 -152.6(9) . . . . ?
C11 O4 C7 C8 27.4(17) . . . . ?
N2 C6 C7 O4 2.0(19) . . . . ?
C5 C6 C7 O4 -176.5(10) . . . . ?
N2 C6 C7 C8 -178.0(11) . . . . ?
C5 C6 C7 C8 3.5(17) . . . . ?
C1 N1 C8 C9 -3.2(15) . . . . ?
C12 N1 C8 C9 -176.8(10) . . . . ?
C1 N1 C8 C7 179.8(10) . . . . ?
C12 N1 C8 C7 6.2(14) . . . . ?
O4 C7 C8 C9 -179.9(10) . . . . ?
C6 C7 C8 C9 0.1(19) . . . . ?
O4 C7 C8 N1 -2.8(17) . . . . ?
C6 C7 C8 N1 177.2(10) . . . . ?
N1 C8 C9 C4 -179.2(9) . . . . ?
C7 C8 C9 C4 -2.3(16) . . . . ?
N1 C8 C9 C3 1.9(16) . . . . ?
C7 C8 C9 C3 178.8(10) . . . . ?
C5 C4 C9 C8 0.6(15) . . . . ?
C5 C4 C9 C3 179.5(10) . . . . ?
O3 C3 C9 C8 179.9(11) . . . . ?
C2 C3 C9 C8 0.2(14) . . . . ?
O3 C3 C9 C4 1.1(17) . . . . ?
C2 C3 C9 C4 -178.7(10) . . . . ?
C1 C2 C10 O1 -1.5(16) . . . . ?
C3 C2 C10 O1 178.3(10) . . . . ?
C1 C2 C10 O2 178.7(10) . . . . ?
C3 C2 C10 O2 -1.5(15) . . . . ?
C7 O4 C11 C12 -52.8(16) . . . . ?
C1 N1 C12 C13 36.1(16) . . . . ?
C8 N1 C12 C13 -150.6(11) . . . . ?
C1 N1 C12 C11 155.7(9) . . . . ?
C8 N1 C12 C11 -31.0(13) . . . . ?
O4 C11 C12 N1 53.2(16) . . . . ?
O4 C11 C12 C13 174.1(18) . . . . ?
C6 N2 C14 C15 114.0(13) . . . . ?
C17 N2 C14 C15 -54.7(16) . . . . ?
C18 N3 C15 C14 176.5(13) . . . . ?
C16 N3 C15 C14 -60.1(14) . . . . ?
N2 C14 C15 N3 56.9(17) . . . . ?
C18 N3 C16 C17 -176.3(11) . . . . ?
C15 N3 C16 C17 60.3(14) . . . . ?
C6 N2 C17 C16 -117.5(16) . . . . ?
C14 N2 C17 C16 51.6(16) . . . . ?
N3 C16 C17 N2 -53.8(17) . . . . ?
C26 N4 C19 C20 -2.0(16) . . . . ?
C30 N4 C19 C20 171.2(10) . . . . ?
N4 C19 C20 C21 -5.8(18) . . . . ?
N4 C19 C20 C28 176.8(9) . . . . ?
C19 C20 C21 O7 -173.3(12) . . . . ?
C28 C20 C21 O7 4.1(16) . . . . ?
C19 C20 C21 C27 7.5(16) . . . . ?
C28 C20 C21 C27 -175.1(9) . . . . ?
C27 C22 C23 F2 176.4(8) . . . . ?
C27 C22 C23 C24 -0.6(18) . . . . ?
C32 N5 C24 C23 -137.3(13) . . . . ?
C35 N5 C24 C23 51.3(18) . . . . ?
C32 N5 C24 C25 39.7(17) . . . . ?
C35 N5 C24 C25 -131.6(15) . . . . ?
F2 C23 C24 N5 2.7(17) . . . . ?
C22 C23 C24 N5 179.9(10) . . . . ?
F2 C23 C24 C25 -174.6(8) . . . . ?
C22 C23 C24 C25 2.6(17) . . . . ?
C29 O8 C25 C26 20.5(16) . . . . ?
C29 O8 C25 C24 -164.0(8) . . . . ?
N5 C24 C25 O8 3.2(17) . . . . ?
C23 C24 C25 O8 -179.5(11) . . . . ?
N5 C24 C25 C26 178.6(11) . . . . ?
C23 C24 C25 C26 -4.1(16) . . . . ?
O8 C25 C26 N4 0.2(16) . . . . ?
C24 C25 C26 N4 -174.9(9) . . . . ?
O8 C25 C26 C27 178.8(10) . . . . ?
C24 C25 C26 C27 3.8(16) . . . . ?
C19 N4 C26 C25 -173.7(10) . . . . ?
C30 N4 C26 C25 12.8(13) . . . . ?
C19 N4 C26 C27 7.7(14) . . . . ?
C30 N4 C26 C27 -165.8(10) . . . . ?
C23 C22 C27 C26 -0.1(15) . . . . ?
C23 C22 C27 C21 -177.2(10) . . . . ?
C25 C26 C27 C22 -1.5(15) . . . . ?
N4 C26 C27 C22 177.1(9) . . . . ?
C25 C26 C27 C21 175.8(10) . . . . ?
N4 C26 C27 C21 -5.6(15) . . . . ?
O7 C21 C27 C22 -3.9(16) . . . . ?
C20 C21 C27 C22 175.3(9) . . . . ?
O7 C21 C27 C26 178.9(10) . . . . ?
C20 C21 C27 C26 -1.8(14) . . . . ?
C19 C20 C28 O5 -1.4(17) . . . . ?
C21 C20 C28 O5 -179.0(11) . . . . ?
C19 C20 C28 O6 179.6(11) . . . . ?
C21 C20 C28 O6 2.1(14) . . . . ?
C25 O8 C29 C30 -50.8(16) . . . . ?
C19 N4 C30 C31 20.1(15) . . . . ?
C26 N4 C30 C31 -166.8(10) . . . . ?
C19 N4 C30 C29 143.9(10) . . . . ?
C26 N4 C30 C29 -43.0(12) . . . . ?
O8 C29 C30 N4 59.5(16) . . . . ?
O8 C29 C30 C31 -175.8(18) . . . . ?
C24 N5 C32 C33 -119.5(13) . . . . ?
C35 N5 C32 C33 52.5(15) . . . . ?
C36 N6 C33 C32 -176.6(12) . . . . ?
C34 N6 C33 C32 61.3(13) . . . . ?
N5 C32 C33 N6 -58.1(15) . . . . ?
C33 N6 C34 C35 -60.9(14) . . . . ?
C36 N6 C34 C35 176.7(10) . . . . ?
C24 N5 C35 C34 120.5(15) . . . . ?
C32 N5 C35 C34 -51.8(14) . . . . ?
N6 C34 C35 N5 56.3(14) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.76 2.527(17) 154.0 . yes
O6 H6 O7 0.82 1.76 2.528(15) 156.0 . yes
O9 H9A N3 0.83 2.05 2.842(14) 161.3 . yes
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_cell_measurement_pressure       1.68


# start Validation Reply Form
_vrf_ATOM007_LH_ME_1p68          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_ME_1p68          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_ME_1p68          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_ME_1p68          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_ME_1p68          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_ME_1p68          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_ME_1p68          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_ME_1p68          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_ME_1p68          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_1p68          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT111_LH_ME_1p68          
;
RESPONSE: The structure is chiral.
;
_vrf_PLAT721_LH_ME_1p68          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints


;
_vrf_PLAT910_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_ME_1p68          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_ME_1p68          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_ME_1p68          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_ME_1p68          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_LH_ME_2p27
_database_code_depnum_ccdc_archive 'CCDC 2481330'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_LEVO_05_H2O_261022

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.5(H2 O1)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   27.806(6)
_cell_length_b                   6.4028(5)
_cell_length_c                   18.0642(15)
_cell_angle_alpha                90
_cell_angle_beta                 113.520(14)
_cell_angle_gamma                90
_cell_volume                     2948.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6966
_cell_measurement_theta_min      3.281
_cell_measurement_theta_max      23.313
_exptl_crystal_description       Lathe
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6681
_exptl_absorpt_correction_t_max  0.7449
_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 D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6966
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.281
_diffrn_reflns_theta_max         23.313
_diffrn_reflns_theta_full        23.313
_diffrn_measured_fraction_theta_max 0.320
_diffrn_measured_fraction_theta_full 0.320
_diffrn_reflns_Laue_measured_fraction_max 0.320
_diffrn_reflns_Laue_measured_fraction_full 0.320
_diffrn_reflns_point_group_measured_fraction_max 0.323
_diffrn_reflns_point_group_measured_fraction_full 0.323
_reflns_number_total             1377
_reflns_number_gt                1115
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_max     0.327
_reflns_Friedel_fraction_full    0.327
_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       'Apex 4 suite'
_computing_cell_refinement       'Apex 4 suite'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0815P)²+5.0007P] 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_abs_structure_details 
;
 Flack x determined using 405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1377
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.833
_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
F1 F 0.2097(7) 0.4442(9) 0.7272(6) 0.0350(19) Uiso 1 1 d D U . . .
O1 O 0.3229(10) 0.4669(12) 1.2317(7) 0.041(3) Uiso 1 1 d D U . . .
O2 O 0.3766(9) 0.4651(13) 1.1685(7) 0.043(3) Uiso 1 1 d D U . . .
H2 H 0.374190 0.459933 1.121799 0.064 Uiso 1 1 calc R U . . .
O3 O 0.3386(9) 0.4747(11) 1.0147(7) 0.033(3) Uiso 1 1 d D U . . .
O4 O 0.1021(9) 0.4452(12) 0.8726(7) 0.035(3) Uiso 1 1 d D U . . .
N1 N 0.1917(9) 0.4574(13) 1.0185(8) 0.023(3) Uiso 1 1 d D U . . .
N2 N 0.1107(8) 0.4613(13) 0.7229(7) 0.028(3) Uiso 1 1 d D U . . .
N3 N 0.0126(9) 0.6415(15) 0.6246(7) 0.036(3) Uiso 1 1 d D U . . .
C1 C 0.2355(9) 0.4608(16) 1.0865(9) 0.022(3) Uiso 1 1 d D U . . .
H1 H 0.231580 0.460735 1.135296 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2850(9) 0.4642(16) 1.0894(8) 0.024(4) Uiso 1 1 d D U . . .
C3 C 0.2941(9) 0.4675(16) 1.0172(8) 0.020(3) Uiso 1 1 d D U . . .
C4 C 0.2488(11) 0.4611(15) 0.8666(9) 0.027(3) Uiso 1 1 d D U . . .
H4 H 0.281113 0.462905 0.862474 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2038(10) 0.4559(15) 0.7985(9) 0.017(3) Uiso 1 1 d D U . . .
C6 C 0.1525(9) 0.4600(17) 0.7962(8) 0.025(3) Uiso 1 1 d D U . . .
C7 C 0.1516(9) 0.4533(17) 0.8731(8) 0.023(3) Uiso 1 1 d D U . . .
C8 C 0.1973(9) 0.4564(14) 0.9445(8) 0.015(3) Uiso 1 1 d D U . . .
C9 C 0.2468(9) 0.4635(15) 0.9425(8) 0.019(3) Uiso 1 1 d D U . . .
C10 C 0.3290(9) 0.4661(15) 1.1689(8) 0.024(3) Uiso 1 1 d D U . . .
C11 C 0.0986(10) 0.5311(16) 0.9429(8) 0.032(3) Uiso 1 1 d D U . . .
H11A H 0.063839 0.504737 0.941231 0.038 Uiso 1 1 calc R U . . .
H11B H 0.103423 0.681154 0.943099 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1389(9) 0.4404(16) 1.0195(7) 0.025(3) Uiso 1 1 d D U . . .
H12 H 0.130771 0.292721 1.023047 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1357(14) 0.556(2) 1.0899(11) 0.035(4) Uiso 1 1 d D U . . .
H13A H 0.156612 0.485246 1.139171 0.053 Uiso 1 1 calc R U . . .
H13B H 0.099908 0.561060 1.084233 0.053 Uiso 1 1 calc R U . . .
H13C H 0.148657 0.695673 1.091361 0.053 Uiso 1 1 calc R U . . .
C14 C 0.0614(8) 0.3547(17) 0.7083(9) 0.029(3) Uiso 1 1 d D U . . .
H14A H 0.065611 0.268312 0.754560 0.034 Uiso 1 1 calc R U . . .
H14B H 0.052697 0.263883 0.661726 0.034 Uiso 1 1 calc R U . . .
C15 C 0.0174(10) 0.5062(16) 0.6936(9) 0.035(3) Uiso 1 1 d D U . . .
H15A H -0.015096 0.431070 0.681722 0.042 Uiso 1 1 calc R U . . .
H15B H 0.024554 0.590715 0.741382 0.042 Uiso 1 1 calc R U . . .
C16 C 0.0620(9) 0.7595(19) 0.6449(9) 0.040(4) Uiso 1 1 d D U . . .
H16A H 0.068295 0.845104 0.692232 0.048 Uiso 1 1 calc R U . . .
H16B H 0.058548 0.851678 0.600497 0.048 Uiso 1 1 calc R U . . .
C17 C 0.1079(10) 0.6151(17) 0.6614(9) 0.034(3) Uiso 1 1 d D U . . .
H17A H 0.104077 0.543807 0.611952 0.041 Uiso 1 1 calc R U . . .
H17B H 0.140078 0.695618 0.679716 0.041 Uiso 1 1 calc R U . . .
C18 C -0.0324(11) 0.784(2) 0.6031(10) 0.058(5) Uiso 1 1 d D U . . .
H18A H -0.063691 0.704057 0.592851 0.086 Uiso 1 1 calc R U . . .
H18B H -0.036161 0.860727 0.555560 0.086 Uiso 1 1 calc R U . . .
H18C H -0.026758 0.878726 0.646862 0.086 Uiso 1 1 calc R U . . .
F2 F 0.2855(7) 0.7327(10) 0.7641(5) 0.0341(18) Uiso 1 1 d D U . . .
O5 O 0.1847(10) 0.7040(12) 0.2617(8) 0.040(3) Uiso 1 1 d D U . . .
O6 O 0.1291(8) 0.7191(14) 0.3220(7) 0.045(3) Uiso 1 1 d D U . . .
H6 H 0.131039 0.712249 0.368402 0.067 Uiso 1 1 calc R U . . .
O7 O 0.1611(8) 0.6798(11) 0.4719(6) 0.037(3) Uiso 1 1 d D U . . .
O8 O 0.3957(9) 0.6998(12) 0.6263(7) 0.039(3) Uiso 1 1 d D U . . .
N4 N 0.3104(8) 0.6638(12) 0.4781(8) 0.025(3) Uiso 1 1 d D U . . .
N5 N 0.3850(8) 0.7197(13) 0.7713(7) 0.028(3) Uiso 1 1 d D U . . .
N6 N 0.4840(9) 0.5846(14) 0.8804(7) 0.031(3) Uiso 1 1 d D U . . .
C19 C 0.2682(8) 0.6694(15) 0.4080(9) 0.027(3) Uiso 1 1 d D U . . .
H19 H 0.273146 0.661280 0.360171 0.032 Uiso 1 1 calc R U . . .
C20 C 0.2185(9) 0.6863(16) 0.4039(8) 0.022(3) Uiso 1 1 d D U . . .
C21 C 0.2062(8) 0.6820(15) 0.4729(8) 0.022(4) Uiso 1 1 d D U . . .
C22 C 0.2467(10) 0.6958(14) 0.6234(9) 0.025(3) Uiso 1 1 d D U . . .
H22 H 0.213718 0.693791 0.625263 0.030 Uiso 1 1 calc R U . . .
C23 C 0.2908(9) 0.7095(16) 0.6929(8) 0.022(3) Uiso 1 1 d D U . . .
C24 C 0.3424(9) 0.7075(17) 0.6982(7) 0.026(3) Uiso 1 1 d D U . . .
C25 C 0.3456(9) 0.7021(17) 0.6220(8) 0.030(3) Uiso 1 1 d D U . . .
C26 C 0.3022(9) 0.6847(14) 0.5497(9) 0.022(3) Uiso 1 1 d D U . . .
C27 C 0.2515(9) 0.6850(15) 0.5499(8) 0.022(3) Uiso 1 1 d D U . . .
C28 C 0.1762(8) 0.7038(16) 0.3223(8) 0.025(3) Uiso 1 1 d D U . . .
C29 C 0.4010(10) 0.7498(16) 0.5508(7) 0.029(3) Uiso 1 1 d D U . . .
H29A H 0.436791 0.725331 0.556751 0.035 Uiso 1 1 calc R U . . .
H29B H 0.392656 0.895722 0.537275 0.035 Uiso 1 1 calc R U . . .
C30 C 0.3641(8) 0.6135(17) 0.4855(7) 0.025(3) Uiso 1 1 d D U . . .
H30 H 0.371612 0.467575 0.502533 0.030 Uiso 1 1 calc R U . . .
C31 C 0.3706(14) 0.641(2) 0.4071(11) 0.040(4) Uiso 1 1 d D U . . .
H31A H 0.361279 0.513600 0.376594 0.060 Uiso 1 1 calc R U . . .
H31B H 0.406469 0.674974 0.418197 0.060 Uiso 1 1 calc R U . . .
H31C H 0.348241 0.751831 0.376499 0.060 Uiso 1 1 calc R U . . .
C32 C 0.4313(8) 0.8444(17) 0.7870(9) 0.028(3) Uiso 1 1 d D U . . .
H32A H 0.435817 0.942037 0.830321 0.034 Uiso 1 1 calc R U . . .
H32B H 0.426996 0.924122 0.739110 0.034 Uiso 1 1 calc R U . . .
C33 C 0.4790(10) 0.7084(17) 0.8101(8) 0.029(3) Uiso 1 1 d D U . . .
H33A H 0.475753 0.617011 0.765525 0.035 Uiso 1 1 calc R U . . .
H33B H 0.509970 0.794367 0.822510 0.035 Uiso 1 1 calc R U . . .
C34 C 0.4377(9) 0.4519(17) 0.8597(8) 0.026(3) Uiso 1 1 d D U . . .
H34A H 0.441668 0.363383 0.905340 0.031 Uiso 1 1 calc R U . . .
H34B H 0.434561 0.362503 0.814653 0.031 Uiso 1 1 calc R U . . .
C35 C 0.3895(11) 0.5795(16) 0.8378(9) 0.029(3) Uiso 1 1 d D U . . .
H35A H 0.359056 0.489065 0.821613 0.035 Uiso 1 1 calc R U . . .
H35B H 0.391131 0.660462 0.884152 0.035 Uiso 1 1 calc R U . . .
C36 C 0.5318(12) 0.459(2) 0.9082(10) 0.051(4) Uiso 1 1 d D U . . .
H36A H 0.534474 0.388656 0.863044 0.077 Uiso 1 1 calc R U . . .
H36B H 0.530627 0.357263 0.946576 0.077 Uiso 1 1 calc R U . . .
H36C H 0.561735 0.547762 0.933368 0.077 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.352(3) 0.500000 0.053(5) Uiso 1 2 d DGS . P . .
H9A H 0.030989 0.317158 0.519634 0.079 Uiso 0.5 1 d DG U P . .
H9B H -0.003129 0.426007 0.535024 0.079 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.394(2) 1.000000 0.045(5) Uiso 1 2 d DGS . P . .
H10A H -0.025684 0.458934 0.999231 0.067 Uiso 0.5 1 d DG U P . .
H10B H 0.003855 0.302636 1.033310 0.067 Uiso 0.5 1 d DG U P . .
_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 C5 1.363(10) . ?
O1 C10 1.213(11) . ?
O2 C10 1.326(14) . ?
O2 H2 0.8200 . ?
O3 C3 1.254(14) . ?
O4 C7 1.374(14) . ?
O4 C11 1.423(10) . ?
N1 C1 1.340(14) . ?
N1 C8 1.405(11) . ?
N1 C12 1.482(14) . ?
N2 C6 1.370(14) . ?
N2 C14 1.457(14) . ?
N2 C17 1.464(11) . ?
N3 C18 1.468(15) . ?
N3 C15 1.478(11) . ?
N3 C16 1.480(14) . ?
C1 C2 1.357(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.425(13) . ?
C2 C10 1.470(14) . ?
C3 C9 1.462(14) . ?
C4 C5 1.360(14) . ?
C4 C9 1.394(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(14) . ?
C6 C7 1.399(12) . ?
C7 C8 1.403(14) . ?
C8 C9 1.394(14) . ?
C11 C12 1.506(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.505(11) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.500(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.507(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.361(10) . ?
O5 C28 1.209(11) . ?
O6 C28 1.311(14) . ?
O6 H6 0.8200 . ?
O7 C21 1.246(14) . ?
O8 C25 1.363(14) . ?
O8 C29 1.464(11) . ?
N4 C19 1.340(14) . ?
N4 C26 1.406(11) . ?
N4 C30 1.482(14) . ?
N5 C24 1.381(14) . ?
N5 C32 1.443(14) . ?
N5 C35 1.465(11) . ?
N6 C33 1.456(11) . ?
N6 C36 1.461(15) . ?
N6 C34 1.461(14) . ?
C19 C20 1.359(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.419(13) . ?
C20 C28 1.478(14) . ?
C21 C27 1.458(14) . ?
C22 C23 1.362(14) . ?
C22 C27 1.389(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.399(14) . ?
C24 C25 1.415(13) . ?
C25 C26 1.385(14) . ?
C26 C27 1.410(14) . ?
C29 C30 1.497(14) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.508(11) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.500(14) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.481(14) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8203 . ?
O9 H9B 0.8240 . ?
O9 H9A 0.8(2) 2_556 ?
O9 H9B 0.8(2) 2_556 ?
O10 H10A 0.8207 . ?
O10 H10B 0.8165 . ?
O10 H10A 0.8(3) 2_557 ?
O10 H10B 0.8(2) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 113.9(16) . . ?
C1 N1 C8 118.0(17) . . ?
C1 N1 C12 122.1(11) . . ?
C8 N1 C12 119.8(16) . . ?
C6 N2 C14 123.1(11) . . ?
C6 N2 C17 120.4(15) . . ?
C14 N2 C17 114.6(16) . . ?
C18 N3 C15 111.6(13) . . ?
C18 N3 C16 110.9(11) . . ?
C15 N3 C16 109.1(15) . . ?
N1 C1 C2 124.8(13) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C1 C2 C3 121.0(16) . . ?
C1 C2 C10 118.3(12) . . ?
C3 C2 C10 120.7(17) . . ?
O3 C3 C2 124.9(17) . . ?
O3 C3 C9 120.2(12) . . ?
C2 C3 C9 114.9(15) . . ?
C5 C4 C9 120.4(18) . . ?
C5 C4 H4 119.8 . . ?
C9 C4 H4 119.8 . . ?
C4 C5 F1 116.2(16) . . ?
C4 C5 C6 125.5(11) . . ?
F1 C5 C6 118.3(17) . . ?
N2 C6 C7 128.0(18) . . ?
N2 C6 C5 119.1(12) . . ?
C7 C6 C5 112.8(15) . . ?
O4 C7 C6 114.1(16) . . ?
O4 C7 C8 122.9(12) . . ?
C6 C7 C8 123.0(17) . . ?
C9 C8 C7 121.2(11) . . ?
C9 C8 N1 120.6(16) . . ?
C7 C8 N1 118.2(17) . . ?
C4 C9 C8 116.9(17) . . ?
C4 C9 C3 122.3(18) . . ?
C8 C9 C3 120.8(11) . . ?
O1 C10 O2 121.3(17) . . ?
O1 C10 C2 122.7(17) . . ?
O2 C10 C2 116.0(13) . . ?
O4 C11 C12 112.4(13) . . ?
O4 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
O4 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N1 C12 C13 111.5(17) . . ?
N1 C12 C11 109.7(12) . . ?
C13 C12 C11 108.3(15) . . ?
N1 C12 H12 109.1 . . ?
C13 C12 H12 109.1 . . ?
C11 C12 H12 109.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.7(11) . . ?
N2 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N3 C15 C14 108.8(13) . . ?
N3 C15 H15A 109.9 . . ?
C14 C15 H15A 109.9 . . ?
N3 C15 H15B 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
N3 C16 C17 111.4(12) . . ?
N3 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N2 C17 C16 110.3(14) . . ?
N2 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 115.2(16) . . ?
C19 N4 C26 117.7(16) . . ?
C19 N4 C30 124.2(11) . . ?
C26 N4 C30 117.8(15) . . ?
C24 N5 C32 125.2(11) . . ?
C24 N5 C35 120.6(14) . . ?
C32 N5 C35 113.6(15) . . ?
C33 N6 C36 111.0(14) . . ?
C33 N6 C34 109.0(14) . . ?
C36 N6 C34 110.8(10) . . ?
N4 C19 C20 122.8(14) . . ?
N4 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C19 C20 C21 123.1(17) . . ?
C19 C20 C28 116.6(12) . . ?
C21 C20 C28 120.3(16) . . ?
O7 C21 C20 125.5(16) . . ?
O7 C21 C27 119.7(12) . . ?
C20 C21 C27 114.7(15) . . ?
C23 C22 C27 119.2(17) . . ?
C23 C22 H22 120.4 . . ?
C27 C22 H22 120.4 . . ?
F2 C23 C22 118.7(16) . . ?
F2 C23 C24 115.5(16) . . ?
C22 C23 C24 125.8(11) . . ?
N5 C24 C23 122.1(12) . . ?
N5 C24 C25 124.6(16) . . ?
C23 C24 C25 113.3(15) . . ?
O8 C25 C26 122.6(12) . . ?
O8 C25 C24 113.9(15) . . ?
C26 C25 C24 123.3(17) . . ?
C25 C26 N4 118.3(16) . . ?
C25 C26 C27 119.6(12) . . ?
N4 C26 C27 122.1(15) . . ?
C22 C27 C26 118.7(16) . . ?
C22 C27 C21 122.4(17) . . ?
C26 C27 C21 118.8(11) . . ?
O5 C28 O6 123.5(17) . . ?
O5 C28 C20 122.6(17) . . ?
O6 C28 C20 113.9(12) . . ?
O8 C29 C30 108.3(12) . . ?
O8 C29 H29A 110.0 . . ?
C30 C29 H29A 110.0 . . ?
O8 C29 H29B 110.0 . . ?
C30 C29 H29B 110.0 . . ?
H29A C29 H29B 108.4 . . ?
N4 C30 C29 107.1(12) . . ?
N4 C30 C31 112.6(18) . . ?
C29 C30 C31 111.8(13) . . ?
N4 C30 H30 108.4 . . ?
C29 C30 H30 108.4 . . ?
C31 C30 H30 108.4 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 110.7(11) . . ?
N5 C32 H32A 109.5 . . ?
C33 C32 H32A 109.5 . . ?
N5 C32 H32B 109.5 . . ?
C33 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
N6 C33 C32 109.0(14) . . ?
N6 C33 H33A 109.9 . . ?
C32 C33 H33A 109.9 . . ?
N6 C33 H33B 109.9 . . ?
C32 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
N6 C34 C35 111.0(11) . . ?
N6 C34 H34A 109.4 . . ?
C35 C34 H34A 109.4 . . ?
N6 C34 H34B 109.4 . . ?
C35 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
N5 C35 C34 109.2(15) . . ?
N5 C35 H35A 109.8 . . ?
C34 C35 H35A 109.8 . . ?
N5 C35 H35B 109.8 . . ?
C34 C35 H35B 109.8 . . ?
H35A C35 H35B 108.3 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 103.8 . . ?
H9A O9 H9A 148.8 . 2_556 ?
H9B O9 H9A 94.2 . 2_556 ?
H9A O9 H9B 94.2 . 2_556 ?
H9B O9 H9B 109.3 . 2_556 ?
H9A O9 H9B 103.8 2_556 2_556 ?
H10A O10 H10B 103.4 . . ?
H10A O10 H10A 119.4 . 2_557 ?
H10B O10 H10A 119.5 . 2_557 ?
H10A O10 H10B 119.5 . 2_557 ?
H10B O10 H10B 88.1 . 2_557 ?
H10A O10 H10B 103.4 2_557 2_557 ?
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
C8 N1 C1 C2 0.3(17) . . . . ?
C12 N1 C1 C2 176.1(10) . . . . ?
N1 C1 C2 C3 0.9(19) . . . . ?
N1 C1 C2 C10 -179.6(9) . . . . ?
C1 C2 C3 O3 178.6(11) . . . . ?
C10 C2 C3 O3 -0.9(16) . . . . ?
C1 C2 C3 C9 -0.9(15) . . . . ?
C10 C2 C3 C9 179.6(9) . . . . ?
C9 C4 C5 F1 -177.1(8) . . . . ?
C9 C4 C5 C6 2.3(17) . . . . ?
C14 N2 C6 C7 -32.3(18) . . . . ?
C17 N2 C6 C7 131.0(14) . . . . ?
C14 N2 C6 C5 144.7(11) . . . . ?
C17 N2 C6 C5 -52.0(17) . . . . ?
C4 C5 C6 N2 177.7(9) . . . . ?
F1 C5 C6 N2 -2.8(16) . . . . ?
C4 C5 C6 C7 -4.8(17) . . . . ?
F1 C5 C6 C7 174.6(8) . . . . ?
C11 O4 C7 C6 -153.0(9) . . . . ?
C11 O4 C7 C8 26.5(16) . . . . ?
N2 C6 C7 O4 0.7(18) . . . . ?
C5 C6 C7 O4 -176.5(10) . . . . ?
N2 C6 C7 C8 -178.8(10) . . . . ?
C5 C6 C7 C8 4.0(16) . . . . ?
O4 C7 C8 C9 179.7(9) . . . . ?
C6 C7 C8 C9 -0.9(17) . . . . ?
O4 C7 C8 N1 -1.9(16) . . . . ?
C6 C7 C8 N1 177.5(9) . . . . ?
C1 N1 C8 C9 -1.4(14) . . . . ?
C12 N1 C8 C9 -177.3(9) . . . . ?
C1 N1 C8 C7 -179.9(10) . . . . ?
C12 N1 C8 C7 4.2(14) . . . . ?
C5 C4 C9 C8 1.2(14) . . . . ?
C5 C4 C9 C3 179.5(9) . . . . ?
C7 C8 C9 C4 -1.9(15) . . . . ?
N1 C8 C9 C4 179.7(9) . . . . ?
C7 C8 C9 C3 179.8(9) . . . . ?
N1 C8 C9 C3 1.4(14) . . . . ?
O3 C3 C9 C4 2.0(16) . . . . ?
C2 C3 C9 C4 -178.4(9) . . . . ?
O3 C3 C9 C8 -179.7(10) . . . . ?
C2 C3 C9 C8 -0.2(14) . . . . ?
C1 C2 C10 O1 -0.8(16) . . . . ?
C3 C2 C10 O1 178.8(10) . . . . ?
C1 C2 C10 O2 178.7(10) . . . . ?
C3 C2 C10 O2 -1.8(15) . . . . ?
C7 O4 C11 C12 -52.0(15) . . . . ?
C1 N1 C12 C13 35.6(16) . . . . ?
C8 N1 C12 C13 -148.7(11) . . . . ?
C1 N1 C12 C11 155.6(9) . . . . ?
C8 N1 C12 C11 -28.7(13) . . . . ?
O4 C11 C12 N1 52.2(16) . . . . ?
O4 C11 C12 C13 174.2(17) . . . . ?
C6 N2 C14 C15 111.9(12) . . . . ?
C17 N2 C14 C15 -52.3(15) . . . . ?
C18 N3 C15 C14 175.8(13) . . . . ?
C16 N3 C15 C14 -61.3(14) . . . . ?
N2 C14 C15 N3 57.1(16) . . . . ?
C18 N3 C16 C17 -175.9(11) . . . . ?
C15 N3 C16 C17 60.7(13) . . . . ?
C6 N2 C17 C16 -115.1(16) . . . . ?
C14 N2 C17 C16 49.5(15) . . . . ?
N3 C16 C17 N2 -53.6(16) . . . . ?
C26 N4 C19 C20 -2.5(14) . . . . ?
C30 N4 C19 C20 170.3(10) . . . . ?
N4 C19 C20 C21 -5.5(17) . . . . ?
N4 C19 C20 C28 176.3(8) . . . . ?
C19 C20 C21 O7 -173.8(11) . . . . ?
C28 C20 C21 O7 4.4(15) . . . . ?
C19 C20 C21 C27 7.5(15) . . . . ?
C28 C20 C21 C27 -174.3(9) . . . . ?
C27 C22 C23 F2 176.1(8) . . . . ?
C27 C22 C23 C24 -2.1(17) . . . . ?
C32 N5 C24 C23 -137.7(12) . . . . ?
C35 N5 C24 C23 51.0(18) . . . . ?
C32 N5 C24 C25 39.2(17) . . . . ?
C35 N5 C24 C25 -132.2(14) . . . . ?
F2 C23 C24 N5 2.6(17) . . . . ?
C22 C23 C24 N5 -179.2(9) . . . . ?
F2 C23 C24 C25 -174.6(8) . . . . ?
C22 C23 C24 C25 3.6(17) . . . . ?
C29 O8 C25 C26 20.2(16) . . . . ?
C29 O8 C25 C24 -164.4(8) . . . . ?
N5 C24 C25 O8 3.0(17) . . . . ?
C23 C24 C25 O8 -179.9(11) . . . . ?
N5 C24 C25 C26 178.4(11) . . . . ?
C23 C24 C25 C26 -4.6(16) . . . . ?
O8 C25 C26 N4 0.0(16) . . . . ?
C24 C25 C26 N4 -174.9(9) . . . . ?
O8 C25 C26 C27 179.0(10) . . . . ?
C24 C25 C26 C27 4.1(16) . . . . ?
C19 N4 C26 C25 -173.1(9) . . . . ?
C30 N4 C26 C25 13.6(13) . . . . ?
C19 N4 C26 C27 7.9(13) . . . . ?
C30 N4 C26 C27 -165.4(9) . . . . ?
C23 C22 C27 C26 1.2(14) . . . . ?
C23 C22 C27 C21 -176.5(9) . . . . ?
C25 C26 C27 C22 -2.2(14) . . . . ?
N4 C26 C27 C22 176.8(8) . . . . ?
C25 C26 C27 C21 175.6(9) . . . . ?
N4 C26 C27 C21 -5.5(14) . . . . ?
O7 C21 C27 C22 -3.2(16) . . . . ?
C20 C21 C27 C22 175.5(8) . . . . ?
O7 C21 C27 C26 179.1(9) . . . . ?
C20 C21 C27 C26 -2.1(14) . . . . ?
C19 C20 C28 O5 -0.3(15) . . . . ?
C21 C20 C28 O5 -178.5(10) . . . . ?
C19 C20 C28 O6 179.8(11) . . . . ?
C21 C20 C28 O6 1.5(14) . . . . ?
C25 O8 C29 C30 -51.5(16) . . . . ?
C19 N4 C30 C29 142.9(9) . . . . ?
C26 N4 C30 C29 -44.3(12) . . . . ?
C19 N4 C30 C31 19.6(14) . . . . ?
C26 N4 C30 C31 -167.6(9) . . . . ?
O8 C29 C30 N4 61.4(15) . . . . ?
O8 C29 C30 C31 -174.8(18) . . . . ?
C24 N5 C32 C33 -117.8(12) . . . . ?
C35 N5 C32 C33 54.1(14) . . . . ?
C36 N6 C33 C32 -176.5(11) . . . . ?
C34 N6 C33 C32 61.2(12) . . . . ?
N5 C32 C33 N6 -57.3(14) . . . . ?
C33 N6 C34 C35 -62.2(13) . . . . ?
C36 N6 C34 C35 175.4(10) . . . . ?
C24 N5 C35 C34 119.2(15) . . . . ?
C32 N5 C35 C34 -53.1(13) . . . . ?
N6 C34 C35 N5 56.5(14) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.79 2.548(16) 153.2 . yes
O6 H6 O7 0.82 1.73 2.504(15) 156.8 . yes
O9 H9B N3 0.82 2.04 2.830(16) 161.3 . yes
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
_cell_measurement_pressure       2.27


# start Validation Reply Form
_vrf_ATOM007_LH_ME_2p27          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_ME_2p27          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_ME_2p27          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_ME_2p27          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_ME_2p27          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_ME_2p27          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_ME_2p27          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_ME_2p27          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_ME_2p27          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_2p27          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT111_LH_ME_2p27          
;
RESPONSE: The structure is chiral.

;
_vrf_PLAT721_LH_ME_2p27          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints

;
_vrf_PLAT910_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_ME_2p27          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_ME_2p27          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_ME_2p27          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_ME_2p27          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;

# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_LH_ME_0p84
_database_code_depnum_ccdc_archive 'CCDC 2481327'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_LEVO_05_H2O_211022

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.5(H2 O1)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   28.224(4)
_cell_length_b                   6.6179(4)
_cell_length_c                   18.3530(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.462(9)
_cell_angle_gamma                90
_cell_volume                     3144.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7420
_cell_measurement_theta_min      3.177
_cell_measurement_theta_max      23.367
_exptl_crystal_description       Lathe
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6681
_exptl_absorpt_correction_t_max  0.7449
_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 D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7420
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.177
_diffrn_reflns_theta_max         23.367
_diffrn_reflns_theta_full        23.367
_diffrn_measured_fraction_theta_max 0.316
_diffrn_measured_fraction_theta_full 0.316
_diffrn_reflns_Laue_measured_fraction_max 0.316
_diffrn_reflns_Laue_measured_fraction_full 0.316
_diffrn_reflns_point_group_measured_fraction_max 0.321
_diffrn_reflns_point_group_measured_fraction_full 0.321
_reflns_number_total             1472
_reflns_number_gt                1134
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.327
_reflns_Friedel_fraction_full    0.327
_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       'Apex 4 suite'
_computing_cell_refinement       'Apex 4 suite'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1303P)²+4.7488P] 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_abs_structure_details 
;
 Flack x determined using 403 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1472
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.2092
_refine_ls_wR_factor_gt          0.1915
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.616
_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
F1 F 0.2083(8) 0.4538(11) 0.7317(6) 0.043(2) Uiso 1 1 d D U . . .
O1 O 0.3224(11) 0.4778(15) 1.2280(9) 0.053(3) Uiso 1 1 d D U . . .
O2 O 0.3736(11) 0.4792(16) 1.1643(9) 0.056(4) Uiso 1 1 d D U . . .
H2 H 0.371468 0.493558 1.118748 0.084 Uiso 1 1 calc R U . . .
O3 O 0.3365(11) 0.4824(13) 1.0136(8) 0.042(3) Uiso 1 1 d D U . . .
O4 O 0.1029(11) 0.4604(14) 0.8755(8) 0.045(3) Uiso 1 1 d D U . . .
N1 N 0.1913(10) 0.4658(14) 1.0189(8) 0.022(3) Uiso 1 1 d D U . . .
N2 N 0.1109(10) 0.4775(16) 0.7285(9) 0.037(3) Uiso 1 1 d D U . . .
N3 N 0.0137(11) 0.6397(17) 0.6249(9) 0.046(4) Uiso 1 1 d D U . . .
C1 C 0.2348(10) 0.4665(18) 1.0858(10) 0.025(4) Uiso 1 1 d D U . . .
H1 H 0.231633 0.463702 1.134363 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2830(10) 0.4711(17) 1.0860(9) 0.025(4) Uiso 1 1 d D U . . .
C3 C 0.2923(10) 0.4755(18) 1.0149(9) 0.022(4) Uiso 1 1 d D U . . .
C4 C 0.2473(12) 0.4695(18) 0.8683(11) 0.034(4) Uiso 1 1 d D U . . .
H4 H 0.278988 0.471775 0.864019 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2026(12) 0.4660(18) 0.8019(10) 0.024(3) Uiso 1 1 d D U . . .
C6 C 0.1522(11) 0.470(2) 0.8005(9) 0.040(4) Uiso 1 1 d D U . . .
C7 C 0.1517(11) 0.464(2) 0.8766(9) 0.033(4) Uiso 1 1 d D U . . .
C8 C 0.1967(11) 0.4637(17) 0.9462(9) 0.024(3) Uiso 1 1 d D U . . .
C9 C 0.2451(11) 0.4695(18) 0.9428(9) 0.026(4) Uiso 1 1 d D U . . .
C10 C 0.3263(11) 0.4781(19) 1.1642(9) 0.033(4) Uiso 1 1 d D U . . .
C11 C 0.1004(11) 0.5433(18) 0.9456(8) 0.036(4) Uiso 1 1 d D U . . .
H11A H 0.065874 0.523722 0.943848 0.043 Uiso 1 1 calc R U . . .
H11B H 0.106822 0.687522 0.947073 0.043 Uiso 1 1 calc R U . . .
C12 C 0.1392(10) 0.4470(19) 1.0202(8) 0.030(3) Uiso 1 1 d D U . . .
H12 H 0.130725 0.303755 1.021405 0.036 Uiso 1 1 calc R U . . .
C13 C 0.136(2) 0.553(2) 1.0902(14) 0.047(4) Uiso 1 1 d D U . . .
H13A H 0.164607 0.515890 1.137681 0.070 Uiso 1 1 calc R U . . .
H13B H 0.104190 0.513777 1.095079 0.070 Uiso 1 1 calc R U . . .
H13C H 0.135591 0.696315 1.082659 0.070 Uiso 1 1 calc R U . . .
C14 C 0.0630(10) 0.3661(19) 0.7109(10) 0.037(4) Uiso 1 1 d D U . . .
H14A H 0.066264 0.282989 0.756186 0.045 Uiso 1 1 calc R U . . .
H14B H 0.056726 0.277378 0.665906 0.045 Uiso 1 1 calc R U . . .
C15 C 0.0181(12) 0.5072(19) 0.6923(10) 0.045(4) Uiso 1 1 d D U . . .
H15A H -0.013420 0.429942 0.678877 0.054 Uiso 1 1 calc R U . . .
H15B H 0.023003 0.588977 0.738581 0.054 Uiso 1 1 calc R U . . .
C16 C 0.0620(12) 0.758(2) 0.6481(11) 0.054(5) Uiso 1 1 d D U . . .
H16A H 0.066054 0.840887 0.693780 0.064 Uiso 1 1 calc R U . . .
H16B H 0.059327 0.847536 0.604805 0.064 Uiso 1 1 calc R U . . .
C17 C 0.1092(13) 0.625(2) 0.6682(11) 0.044(4) Uiso 1 1 d D U . . .
H17A H 0.107841 0.556187 0.620841 0.053 Uiso 1 1 calc R U . . .
H17B H 0.140130 0.708173 0.688119 0.053 Uiso 1 1 calc R U . . .
C18 C -0.0320(13) 0.771(3) 0.6028(13) 0.075(6) Uiso 1 1 d D U . . .
H18A H -0.062245 0.689897 0.592005 0.112 Uiso 1 1 calc R U . . .
H18B H -0.035947 0.847524 0.556248 0.112 Uiso 1 1 calc R U . . .
H18C H -0.027731 0.862258 0.645739 0.112 Uiso 1 1 calc R U . . .
F2 F 0.2870(8) 0.7211(12) 0.7613(6) 0.043(2) Uiso 1 1 d D U . . .
O5 O 0.1809(12) 0.6911(14) 0.2638(9) 0.053(3) Uiso 1 1 d D U . . .
O6 O 0.1282(10) 0.7040(16) 0.3255(8) 0.058(4) Uiso 1 1 d D U . . .
H6 H 0.130231 0.693995 0.371215 0.087 Uiso 1 1 calc R U . . .
O7 O 0.1641(10) 0.6774(13) 0.4758(8) 0.046(3) Uiso 1 1 d D U . . .
O8 O 0.3953(10) 0.6853(13) 0.6237(8) 0.048(3) Uiso 1 1 d D U . . .
N4 N 0.3095(9) 0.6585(14) 0.4782(8) 0.029(3) Uiso 1 1 d D U . . .
N5 N 0.3860(10) 0.7035(15) 0.7675(8) 0.037(3) Uiso 1 1 d D U . . .
N6 N 0.4836(11) 0.5842(17) 0.8789(9) 0.040(3) Uiso 1 1 d D U . . .
C19 C 0.2676(9) 0.6633(19) 0.4095(10) 0.036(4) Uiso 1 1 d D U . . .
H19 H 0.272636 0.656478 0.362420 0.043 Uiso 1 1 calc R U . . .
C20 C 0.2181(10) 0.6775(17) 0.4043(9) 0.024(4) Uiso 1 1 d D U . . .
C21 C 0.2083(9) 0.6783(19) 0.4748(9) 0.033(4) Uiso 1 1 d D U . . .
C22 C 0.2495(11) 0.6916(17) 0.6241(10) 0.036(4) Uiso 1 1 d D U . . .
H22 H 0.217329 0.693856 0.626851 0.043 Uiso 1 1 calc R U . . .
C23 C 0.2929(11) 0.7006(17) 0.6916(9) 0.026(4) Uiso 1 1 d D U . . .
C24 C 0.3436(10) 0.6941(19) 0.6962(8) 0.035(4) Uiso 1 1 d D U . . .
C25 C 0.3463(10) 0.691(2) 0.6208(9) 0.039(4) Uiso 1 1 d D U . . .
C26 C 0.3028(10) 0.6777(16) 0.5499(9) 0.028(4) Uiso 1 1 d D U . . .
C27 C 0.2529(9) 0.6788(17) 0.5504(8) 0.027(4) Uiso 1 1 d D U . . .
C28 C 0.1748(10) 0.6929(18) 0.3254(9) 0.033(4) Uiso 1 1 d D U . . .
C29 C 0.3997(11) 0.7408(19) 0.5498(8) 0.035(4) Uiso 1 1 d D U . . .
H29A H 0.434710 0.717431 0.554311 0.042 Uiso 1 1 calc R U . . .
H29B H 0.391806 0.883026 0.538747 0.042 Uiso 1 1 calc R U . . .
C30 C 0.3625(9) 0.6149(19) 0.4836(8) 0.031(4) Uiso 1 1 d D U . . .
H30 H 0.370077 0.472379 0.498001 0.037 Uiso 1 1 calc R U . . .
C31 C 0.3701(17) 0.652(2) 0.4081(13) 0.047(5) Uiso 1 1 d D U . . .
H31A H 0.364263 0.528289 0.378240 0.070 Uiso 1 1 calc R U . . .
H31B H 0.404702 0.697662 0.420657 0.070 Uiso 1 1 calc R U . . .
H31C H 0.346051 0.752511 0.377044 0.070 Uiso 1 1 calc R U . . .
C32 C 0.4304(10) 0.8289(19) 0.7822(10) 0.036(4) Uiso 1 1 d D U . . .
H32A H 0.433342 0.927957 0.822722 0.043 Uiso 1 1 calc R U . . .
H32B H 0.426466 0.900618 0.734006 0.043 Uiso 1 1 calc R U . . .
C33 C 0.4778(12) 0.701(2) 0.8089(9) 0.042(4) Uiso 1 1 d D U . . .
H33A H 0.475952 0.610656 0.766352 0.051 Uiso 1 1 calc R U . . .
H33B H 0.507832 0.787421 0.820919 0.051 Uiso 1 1 calc R U . . .
C34 C 0.4379(11) 0.454(2) 0.8570(10) 0.032(4) Uiso 1 1 d D U . . .
H34A H 0.441478 0.369086 0.901958 0.039 Uiso 1 1 calc R U . . .
H34B H 0.436279 0.366527 0.813692 0.039 Uiso 1 1 calc R U . . .
C35 C 0.3889(13) 0.5702(18) 0.8325(10) 0.032(4) Uiso 1 1 d D U . . .
H35A H 0.359674 0.478697 0.815199 0.038 Uiso 1 1 calc R U . . .
H35B H 0.388514 0.648948 0.876829 0.038 Uiso 1 1 calc R U . . .
C36 C 0.5313(14) 0.465(3) 0.9080(13) 0.067(6) Uiso 1 1 d D U . . .
H36A H 0.533529 0.389229 0.864947 0.100 Uiso 1 1 calc R U . . .
H36B H 0.531133 0.374057 0.948656 0.100 Uiso 1 1 calc R U . . .
H36C H 0.560456 0.554099 0.929590 0.100 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.359(4) 0.500000 0.070(6) Uiso 1 2 d DGS . P . .
H9A H -0.006597 0.436275 0.530912 0.105 Uiso 0.5 1 d DG U P . .
H9B H 0.032337 0.346953 0.520620 0.105 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.381(2) 1.000000 0.059(6) Uiso 1 2 d DGS . P . .
H10A H -0.022449 0.455853 1.004750 0.089 Uiso 0.5 1 d DG U P . .
H10B H 0.001998 0.283093 1.030269 0.089 Uiso 0.5 1 d DG U P . .
_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 C5 1.365(11) . ?
O1 C10 1.219(13) . ?
O2 C10 1.332(15) . ?
O2 H2 0.8200 . ?
O3 C3 1.259(15) . ?
O4 C7 1.371(14) . ?
O4 C11 1.425(11) . ?
N1 C1 1.347(14) . ?
N1 C8 1.402(12) . ?
N1 C12 1.487(14) . ?
N2 C6 1.370(14) . ?
N2 C14 1.460(14) . ?
N2 C17 1.464(12) . ?
N3 C18 1.473(15) . ?
N3 C16 1.479(15) . ?
N3 C15 1.480(12) . ?
C1 C2 1.360(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.430(13) . ?
C2 C10 1.470(14) . ?
C3 C9 1.458(14) . ?
C4 C5 1.361(15) . ?
C4 C9 1.393(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(14) . ?
C6 C7 1.404(13) . ?
C7 C8 1.397(14) . ?
C8 C9 1.391(14) . ?
C11 C12 1.513(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.501(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.499(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.513(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.362(12) . ?
O5 C28 1.210(12) . ?
O6 C28 1.317(15) . ?
O6 H6 0.8200 . ?
O7 C21 1.254(15) . ?
O8 C25 1.364(15) . ?
O8 C29 1.457(12) . ?
N4 C19 1.343(14) . ?
N4 C26 1.406(12) . ?
N4 C30 1.489(14) . ?
N5 C24 1.379(14) . ?
N5 C32 1.435(14) . ?
N5 C35 1.460(11) . ?
N6 C33 1.454(12) . ?
N6 C36 1.466(15) . ?
N6 C34 1.466(14) . ?
C19 C20 1.366(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.427(13) . ?
C20 C28 1.481(14) . ?
C21 C27 1.455(14) . ?
C22 C23 1.353(15) . ?
C22 C27 1.395(13) . ?
C22 H22 0.9300 . ?
C23 C24 1.399(14) . ?
C24 C25 1.415(14) . ?
C25 C26 1.392(14) . ?
C26 C27 1.414(14) . ?
C29 C30 1.502(14) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.504(12) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.491(15) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.486(15) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8390 . ?
O9 H9B 0.8410 . ?
O9 H9A 0.8(3) 2_556 ?
O9 H9B 0.84(11) 2_556 ?
O10 H10A 0.8364 . ?
O10 H10B 0.8398 . ?
O10 H10A 0.8(4) 2_557 ?
O10 H10B 0.8(3) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 113.0(19) . . ?
C1 N1 C8 117.6(18) . . ?
C1 N1 C12 122.2(11) . . ?
C8 N1 C12 119.9(18) . . ?
C6 N2 C14 123.4(13) . . ?
C6 N2 C17 120.9(18) . . ?
C14 N2 C17 114.9(18) . . ?
C18 N3 C16 111.8(14) . . ?
C18 N3 C15 110.8(17) . . ?
C16 N3 C15 108.1(18) . . ?
N1 C1 C2 123.3(14) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 123.1(18) . . ?
C1 C2 C10 116.5(13) . . ?
C3 C2 C10 120.4(19) . . ?
O3 C3 C2 124.3(19) . . ?
O3 C3 C9 122.6(13) . . ?
C2 C3 C9 113.1(17) . . ?
C5 C4 C9 119(2) . . ?
C5 C4 H4 120.3 . . ?
C9 C4 H4 120.3 . . ?
C4 C5 F1 115.5(19) . . ?
C4 C5 C6 125.8(13) . . ?
F1 C5 C6 119(2) . . ?
N2 C6 C7 128(2) . . ?
N2 C6 C5 118.8(15) . . ?
C7 C6 C5 112.9(17) . . ?
O4 C7 C8 123.8(14) . . ?
O4 C7 C6 113.2(18) . . ?
C8 C7 C6 123.0(19) . . ?
C9 C8 C7 120.7(12) . . ?
C9 C8 N1 121.5(18) . . ?
C7 C8 N1 117.8(19) . . ?
C8 C9 C4 118.1(19) . . ?
C8 C9 C3 121.3(12) . . ?
C4 C9 C3 121(2) . . ?
O1 C10 O2 118(2) . . ?
O1 C10 C2 125(2) . . ?
O2 C10 C2 116.4(15) . . ?
O4 C11 C12 112.1(15) . . ?
O4 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
O4 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N1 C12 C13 112(2) . . ?
N1 C12 C11 108.3(14) . . ?
C13 C12 C11 107.9(17) . . ?
N1 C12 H12 109.4 . . ?
C13 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.1(13) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 110.1(17) . . ?
N3 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N3 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
N3 C16 C17 112.7(15) . . ?
N3 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N3 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
N2 C17 C16 109.4(18) . . ?
N2 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 114.8(18) . . ?
C19 N4 C26 118.8(18) . . ?
C19 N4 C30 123.5(12) . . ?
C26 N4 C30 117.4(16) . . ?
C24 N5 C32 124.5(13) . . ?
C24 N5 C35 119.6(17) . . ?
C32 N5 C35 115.7(18) . . ?
C33 N6 C36 111.9(17) . . ?
C33 N6 C34 107.1(17) . . ?
C36 N6 C34 111.3(13) . . ?
N4 C19 C20 124.0(16) . . ?
N4 C19 H19 118.0 . . ?
C20 C19 H19 118.0 . . ?
C19 C20 C21 120.0(19) . . ?
C19 C20 C28 119.8(14) . . ?
C21 C20 C28 120.2(17) . . ?
O7 C21 C20 124.5(18) . . ?
O7 C21 C27 118.2(14) . . ?
C20 C21 C27 117.3(17) . . ?
C23 C22 C27 120.3(19) . . ?
C23 C22 H22 119.9 . . ?
C27 C22 H22 119.9 . . ?
C22 C23 F2 117.3(18) . . ?
C22 C23 C24 125.8(12) . . ?
F2 C23 C24 116.9(19) . . ?
N5 C24 C23 122.4(14) . . ?
N5 C24 C25 124.3(18) . . ?
C23 C24 C25 113.1(16) . . ?
O8 C25 C26 122.5(14) . . ?
O8 C25 C24 114.3(17) . . ?
C26 C25 C24 123.0(18) . . ?
C25 C26 N4 118.9(17) . . ?
C25 C26 C27 120.3(12) . . ?
N4 C26 C27 120.8(17) . . ?
C22 C27 C26 117.3(18) . . ?
C22 C27 C21 123.9(19) . . ?
C26 C27 C21 118.7(13) . . ?
O5 C28 O6 121(2) . . ?
O5 C28 C20 123(2) . . ?
O6 C28 C20 116.0(14) . . ?
O8 C29 C30 108.8(13) . . ?
O8 C29 H29A 109.9 . . ?
C30 C29 H29A 109.9 . . ?
O8 C29 H29B 109.9 . . ?
C30 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
N4 C30 C29 107.9(14) . . ?
N4 C30 C31 115(2) . . ?
C29 C30 C31 110.3(15) . . ?
N4 C30 H30 108.0 . . ?
C29 C30 H30 108.0 . . ?
C31 C30 H30 108.0 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 109.7(13) . . ?
N5 C32 H32A 109.7 . . ?
C33 C32 H32A 109.7 . . ?
N5 C32 H32B 109.7 . . ?
C33 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
N6 C33 C32 111.2(18) . . ?
N6 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
N6 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
N6 C34 C35 112.9(13) . . ?
N6 C34 H34A 109.0 . . ?
C35 C34 H34A 109.0 . . ?
N6 C34 H34B 109.0 . . ?
C35 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
N5 C35 C34 107.6(18) . . ?
N5 C35 H35A 110.2 . . ?
C34 C35 H35A 110.2 . . ?
N5 C35 H35B 110.2 . . ?
C34 C35 H35B 110.2 . . ?
H35A C35 H35B 108.5 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 104.2 . . ?
H9A O9 H9A 104.6 . 2_556 ?
H9B O9 H9A 82.4 . 2_556 ?
H9A O9 H9B 82.4 . 2_556 ?
H9B O9 H9B 169.4 . 2_556 ?
H9A O9 H9B 104.2 2_556 2_556 ?
H10A O10 H10B 104.0 . . ?
H10A O10 H10A 107.2 . 2_557 ?
H10B O10 H10A 132.2 . 2_557 ?
H10A O10 H10B 132.2 . 2_557 ?
H10B O10 H10B 79.3 . 2_557 ?
H10A O10 H10B 104.0 2_557 2_557 ?
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
C8 N1 C1 C2 2.0(18) . . . . ?
C12 N1 C1 C2 175.8(11) . . . . ?
N1 C1 C2 C3 0(2) . . . . ?
N1 C1 C2 C10 178.0(11) . . . . ?
C1 C2 C3 O3 179.0(13) . . . . ?
C10 C2 C3 O3 1.1(19) . . . . ?
C1 C2 C3 C9 -1.4(17) . . . . ?
C10 C2 C3 C9 -179.4(10) . . . . ?
C9 C4 C5 F1 -176.2(9) . . . . ?
C9 C4 C5 C6 2(2) . . . . ?
C14 N2 C6 C7 -39(2) . . . . ?
C17 N2 C6 C7 130.8(18) . . . . ?
C14 N2 C6 C5 141.0(14) . . . . ?
C17 N2 C6 C5 -49(2) . . . . ?
C4 C5 C6 N2 176.2(12) . . . . ?
F1 C5 C6 N2 -5(2) . . . . ?
C4 C5 C6 C7 -4(2) . . . . ?
F1 C5 C6 C7 174.7(10) . . . . ?
C11 O4 C7 C8 26.2(19) . . . . ?
C11 O4 C7 C6 -153.7(11) . . . . ?
N2 C6 C7 O4 2(2) . . . . ?
C5 C6 C7 O4 -177.8(12) . . . . ?
N2 C6 C7 C8 -177.6(13) . . . . ?
C5 C6 C7 C8 2(2) . . . . ?
O4 C7 C8 C9 -179.5(11) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
O4 C7 C8 N1 -2(2) . . . . ?
C6 C7 C8 N1 177.7(11) . . . . ?
C1 N1 C8 C9 -2.3(17) . . . . ?
C12 N1 C8 C9 -176.3(11) . . . . ?
C1 N1 C8 C7 -179.6(12) . . . . ?
C12 N1 C8 C7 6.4(16) . . . . ?
C7 C8 C9 C4 -2.0(19) . . . . ?
N1 C8 C9 C4 -179.2(10) . . . . ?
C7 C8 C9 C3 178.0(11) . . . . ?
N1 C8 C9 C3 0.8(18) . . . . ?
C5 C4 C9 C8 0.7(18) . . . . ?
C5 C4 C9 C3 -179.3(11) . . . . ?
O3 C3 C9 C8 -179.4(12) . . . . ?
C2 C3 C9 C8 1.0(17) . . . . ?
O3 C3 C9 C4 0.6(19) . . . . ?
C2 C3 C9 C4 -179.0(11) . . . . ?
C1 C2 C10 O1 1(2) . . . . ?
C3 C2 C10 O1 179.0(12) . . . . ?
C1 C2 C10 O2 178.9(12) . . . . ?
C3 C2 C10 O2 -3.0(17) . . . . ?
C7 O4 C11 C12 -53.0(18) . . . . ?
C1 N1 C12 C13 35.5(17) . . . . ?
C8 N1 C12 C13 -150.7(12) . . . . ?
C1 N1 C12 C11 154.6(10) . . . . ?
C8 N1 C12 C11 -31.7(14) . . . . ?
O4 C11 C12 N1 54.9(19) . . . . ?
O4 C11 C12 C13 177(2) . . . . ?
C6 N2 C14 C15 117.6(15) . . . . ?
C17 N2 C14 C15 -52.8(18) . . . . ?
C18 N3 C15 C14 176.7(15) . . . . ?
C16 N3 C15 C14 -60.4(16) . . . . ?
N2 C14 C15 N3 57.2(19) . . . . ?
C18 N3 C16 C17 -177.9(13) . . . . ?
C15 N3 C16 C17 59.8(17) . . . . ?
C6 N2 C17 C16 -120.8(19) . . . . ?
C14 N2 C17 C16 49.9(18) . . . . ?
N3 C16 C17 N2 -54(2) . . . . ?
C26 N4 C19 C20 -3(2) . . . . ?
C30 N4 C19 C20 171.3(12) . . . . ?
N4 C19 C20 C21 -3(2) . . . . ?
N4 C19 C20 C28 176.6(10) . . . . ?
C19 C20 C21 O7 -175.1(14) . . . . ?
C28 C20 C21 O7 5.2(19) . . . . ?
C19 C20 C21 C27 4.5(18) . . . . ?
C28 C20 C21 C27 -175.2(10) . . . . ?
C27 C22 C23 F2 177.4(9) . . . . ?
C27 C22 C23 C24 -1(2) . . . . ?
C32 N5 C24 C23 -134.0(14) . . . . ?
C35 N5 C24 C23 50(2) . . . . ?
C32 N5 C24 C25 42(2) . . . . ?
C35 N5 C24 C25 -134.5(16) . . . . ?
C22 C23 C24 N5 -179.8(11) . . . . ?
F2 C23 C24 N5 1(2) . . . . ?
C22 C23 C24 C25 4(2) . . . . ?
F2 C23 C24 C25 -174.7(9) . . . . ?
C29 O8 C25 C26 22.0(18) . . . . ?
C29 O8 C25 C24 -162.8(10) . . . . ?
N5 C24 C25 O8 4(2) . . . . ?
C23 C24 C25 O8 179.7(12) . . . . ?
N5 C24 C25 C26 178.8(12) . . . . ?
C23 C24 C25 C26 -5.2(19) . . . . ?
O8 C25 C26 N4 -0.1(19) . . . . ?
C24 C25 C26 N4 -174.8(11) . . . . ?
O8 C25 C26 C27 178.4(12) . . . . ?
C24 C25 C26 C27 3.6(19) . . . . ?
C19 N4 C26 C25 -174.4(11) . . . . ?
C30 N4 C26 C25 11.1(15) . . . . ?
C19 N4 C26 C27 7.1(17) . . . . ?
C30 N4 C26 C27 -167.3(11) . . . . ?
C23 C22 C27 C26 -0.5(18) . . . . ?
C23 C22 C27 C21 -176.9(11) . . . . ?
C25 C26 C27 C22 -0.5(18) . . . . ?
N4 C26 C27 C22 177.9(10) . . . . ?
C25 C26 C27 C21 176.0(11) . . . . ?
N4 C26 C27 C21 -5.5(17) . . . . ?
O7 C21 C27 C22 -4(2) . . . . ?
C20 C21 C27 C22 176.1(10) . . . . ?
O7 C21 C27 C26 179.4(11) . . . . ?
C20 C21 C27 C26 -0.2(17) . . . . ?
C19 C20 C28 O5 0.9(19) . . . . ?
C21 C20 C28 O5 -179.3(12) . . . . ?
C19 C20 C28 O6 179.3(13) . . . . ?
C21 C20 C28 O6 -0.9(17) . . . . ?
C25 O8 C29 C30 -52.6(18) . . . . ?
C19 N4 C30 C29 144.7(11) . . . . ?
C26 N4 C30 C29 -41.0(13) . . . . ?
C19 N4 C30 C31 21.6(17) . . . . ?
C26 N4 C30 C31 -164.2(11) . . . . ?
O8 C29 C30 N4 60.5(18) . . . . ?
O8 C29 C30 C31 -174(2) . . . . ?
C24 N5 C32 C33 -123.0(14) . . . . ?
C35 N5 C32 C33 53.2(18) . . . . ?
C36 N6 C33 C32 -177.4(13) . . . . ?
C34 N6 C33 C32 60.4(14) . . . . ?
N5 C32 C33 N6 -56.6(18) . . . . ?
C33 N6 C34 C35 -61.4(16) . . . . ?
C36 N6 C34 C35 176.0(12) . . . . ?
C24 N5 C35 C34 124.2(16) . . . . ?
C32 N5 C35 C34 -52.2(15) . . . . ?
N6 C34 C35 N5 56.0(16) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.79 2.54(2) 151.9 . yes
O6 H6 O7 0.82 1.77 2.537(18) 154.1 . yes
O9 H9A N3 0.84 2.08 2.86(2) 153.4 . yes
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_cell_measurement_pressure       0.84

# start Validation Reply Form
_vrf_ATOM007_LH_ME_0p84          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_ME_0p84          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_ME_0p84          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_ME_0p84          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_ME_0p84          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_ME_0p84          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_ME_0p84          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_ME_0p84          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_ME_0p84          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_0p84          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT111_LH_ME_0p84          
;
RESPONSE: The structure is chiral.
;
_vrf_PLAT721_LH_ME_0p84          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints

;
_vrf_PLAT910_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_ME_0p84          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_ME_0p84          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_ME_0p84          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_ME_0p84          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_LH_PE_0p29
_database_code_depnum_ccdc_archive 'CCDC 2481331'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_iain

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.25(H4 O2)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   28.753(4)
_cell_length_b                   6.7900(8)
_cell_length_c                   18.636(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.838(11)
_cell_angle_gamma                90
_cell_volume                     3328.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    14088
_cell_measurement_theta_min      2.307
_cell_measurement_theta_max      24.788
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.998
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon III'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14088
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.307
_diffrn_reflns_theta_max         24.788
_diffrn_reflns_theta_full        24.788
_diffrn_measured_fraction_theta_max 0.599
_diffrn_measured_fraction_theta_full 0.599
_diffrn_reflns_Laue_measured_fraction_max 0.599
_diffrn_reflns_Laue_measured_fraction_full 0.599
_diffrn_reflns_point_group_measured_fraction_max 0.590
_diffrn_reflns_point_group_measured_fraction_full 0.590
_reflns_number_total             3365
_reflns_number_gt                1849
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_max     0.579
_reflns_Friedel_fraction_full    0.579
_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_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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_abs_structure_details 
;
 Flack x determined using 609 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3365
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.0958
_refine_ls_wR_factor_ref         0.3232
_refine_ls_wR_factor_gt          0.2627
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.760
_refine_ls_shift/su_max          0.998
_refine_ls_shift/su_mean         0.039
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 0.2060(2) 0.4707(11) 0.7358(7) 0.058(2) Uiso 1 1 d D U . . .
O1 O 0.3202(3) 0.4936(15) 1.2239(9) 0.070(3) Uiso 1 1 d D U . . .
O2 O 0.3721(3) 0.4917(15) 1.1610(11) 0.066(3) Uiso 1 1 d D U . . .
H2 H 0.370820 0.560104 1.123949 0.100 Uiso 1 1 calc R U . . .
O3 O 0.3333(3) 0.4927(11) 1.0153(8) 0.045(2) Uiso 1 1 d D U . . .
O4 O 0.1040(3) 0.4773(12) 0.8794(7) 0.050(2) Uiso 1 1 d D U . . .
N1 N 0.1926(3) 0.4735(14) 1.0205(7) 0.037(2) Uiso 1 1 d D U . . .
N2 N 0.1112(3) 0.4999(14) 0.7353(8) 0.047(3) Uiso 1 1 d D U . . .
N3 N 0.0164(3) 0.6383(13) 0.6272(9) 0.049(3) Uiso 1 1 d D U . . .
C1 C 0.2352(3) 0.4767(17) 1.0868(9) 0.046(3) Uiso 1 1 d D U . . .
H1 H 0.231854 0.474186 1.134367 0.055 Uiso 1 1 calc R U . . .
C2 C 0.2831(3) 0.4835(18) 1.0883(8) 0.039(3) Uiso 1 1 d D U . . .
C3 C 0.2897(3) 0.4867(15) 1.0161(8) 0.031(3) Uiso 1 1 d D U . . .
C4 C 0.2467(4) 0.4822(17) 0.8704(9) 0.039(3) Uiso 1 1 d D U . . .
H4 H 0.277955 0.480405 0.866575 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2027(4) 0.4842(18) 0.8056(8) 0.043(3) Uiso 1 1 d D U . . .
C6 C 0.1534(3) 0.4842(17) 0.8045(8) 0.036(3) Uiso 1 1 d D U . . .
C7 C 0.1514(3) 0.4795(16) 0.8776(8) 0.032(3) Uiso 1 1 d D U . . .
C8 C 0.1959(3) 0.4783(16) 0.9477(8) 0.032(3) Uiso 1 1 d D U . . .
C9 C 0.2436(3) 0.4827(17) 0.9435(9) 0.034(3) Uiso 1 1 d D U . . .
C10 C 0.3274(4) 0.4925(18) 1.1650(9) 0.045(4) Uiso 1 1 d D U . . .
C11 C 0.1041(4) 0.5519(18) 0.9501(8) 0.045(3) Uiso 1 1 d D U . . .
H11A H 0.070309 0.538052 0.949130 0.054 Uiso 1 1 calc R U . . .
H11B H 0.112116 0.691350 0.953603 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1415(3) 0.4506(17) 1.0219(8) 0.042(3) Uiso 1 1 d D U . . .
H12 H 0.132935 0.310490 1.020458 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1381(5) 0.547(2) 1.0925(10) 0.057(4) Uiso 1 1 d D U . . .
H13A H 0.155610 0.467431 1.138147 0.085 Uiso 1 1 calc R U . . .
H13B H 0.103000 0.559280 1.084277 0.085 Uiso 1 1 calc R U . . .
H13C H 0.153372 0.675047 1.100087 0.085 Uiso 1 1 calc R U . . .
C14 C 0.0652(3) 0.3859(16) 0.7176(11) 0.045(3) Uiso 1 1 d D U . . .
H14A H 0.068306 0.311153 0.763628 0.054 Uiso 1 1 calc R U . . .
H14B H 0.061381 0.293052 0.675977 0.054 Uiso 1 1 calc R U . . .
C15 C 0.0186(4) 0.5144(16) 0.6925(9) 0.049(4) Uiso 1 1 d D U . . .
H15A H -0.011623 0.433058 0.676499 0.059 Uiso 1 1 calc R U . . .
H15B H 0.020086 0.596222 0.736049 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0617(4) 0.7628(17) 0.6504(12) 0.055(4) Uiso 1 1 d D U . . .
H16A H 0.064534 0.845090 0.694497 0.066 Uiso 1 1 calc R U . . .
H16B H 0.059259 0.847797 0.607141 0.066 Uiso 1 1 calc R U . . .
C17 C 0.1077(4) 0.6326(18) 0.6727(10) 0.055(4) Uiso 1 1 d D U . . .
H17A H 0.105588 0.556935 0.627374 0.066 Uiso 1 1 calc R U . . .
H17B H 0.138032 0.713390 0.689440 0.066 Uiso 1 1 calc R U . . .
C18 C -0.0295(4) 0.762(2) 0.5998(14) 0.069(5) Uiso 1 1 d D U . . .
H18A H -0.059116 0.680956 0.576561 0.104 Uiso 1 1 calc R U . . .
H18B H -0.028223 0.854652 0.561615 0.104 Uiso 1 1 calc R U . . .
H18C H -0.031045 0.832846 0.643506 0.104 Uiso 1 1 calc R U . . .
F2 F 0.2911(3) 0.7049(11) 0.7609(7) 0.062(2) Uiso 1 1 d D U . . .
O5 O 0.1799(4) 0.6758(16) 0.2704(9) 0.082(4) Uiso 1 1 d D U . . .
O6 O 0.1284(3) 0.6924(15) 0.3336(9) 0.063(3) Uiso 1 1 d D U . . .
H6 H 0.131799 0.677217 0.379135 0.094 Uiso 1 1 calc R U . . .
O7 O 0.1647(3) 0.6775(11) 0.4802(7) 0.044(2) Uiso 1 1 d D U . . .
O8 O 0.3944(3) 0.6723(11) 0.6208(8) 0.046(2) Uiso 1 1 d D U . . .
N4 N 0.3066(3) 0.6513(13) 0.4781(8) 0.040(3) Uiso 1 1 d D U . . .
N5 N 0.3867(3) 0.6833(14) 0.7618(8) 0.053(3) Uiso 1 1 d D U . . .
N6 N 0.4829(3) 0.5858(15) 0.8762(9) 0.055(3) Uiso 1 1 d D U . . .
C19 C 0.2651(4) 0.6553(18) 0.4109(10) 0.054(4) Uiso 1 1 d D U . . .
H19 H 0.269023 0.647711 0.363821 0.065 Uiso 1 1 calc R U . . .
C20 C 0.2162(4) 0.6704(16) 0.4088(8) 0.040(3) Uiso 1 1 d D U . . .
C21 C 0.2085(3) 0.6716(16) 0.4793(8) 0.039(3) Uiso 1 1 d D U . . .
C22 C 0.2505(4) 0.6791(15) 0.6244(8) 0.036(3) Uiso 1 1 d D U . . .
H22 H 0.219081 0.676838 0.627487 0.043 Uiso 1 1 calc R U . . .
C23 C 0.2941(4) 0.6867(17) 0.6901(8) 0.045(4) Uiso 1 1 d D U . . .
C24 C 0.3432(3) 0.6823(16) 0.6927(8) 0.038(3) Uiso 1 1 d D U . . .
C25 C 0.3463(3) 0.6802(16) 0.6194(8) 0.034(3) Uiso 1 1 d D U . . .
C26 C 0.3026(3) 0.6732(16) 0.5499(8) 0.039(3) Uiso 1 1 d D U . . .
C27 C 0.2540(3) 0.6746(15) 0.5519(8) 0.035(3) Uiso 1 1 d D U . . .
C28 C 0.1736(4) 0.6810(19) 0.3301(9) 0.050(4) Uiso 1 1 d D U . . .
C29 C 0.3958(4) 0.7298(18) 0.5479(8) 0.049(3) Uiso 1 1 d D U . . .
H29A H 0.429769 0.709694 0.550321 0.059 Uiso 1 1 calc R U . . .
H29B H 0.387858 0.868972 0.539136 0.059 Uiso 1 1 calc R U . . .
C30 C 0.3583(3) 0.6134(18) 0.4802(9) 0.045(3) Uiso 1 1 d D U . . .
H30 H 0.366087 0.472949 0.490303 0.054 Uiso 1 1 calc R U . . .
C31 C 0.3614(5) 0.667(2) 0.4036(12) 0.082(5) Uiso 1 1 d D U . . .
H31A H 0.341214 0.576430 0.363548 0.123 Uiso 1 1 calc R U . . .
H31B H 0.396142 0.659985 0.409646 0.123 Uiso 1 1 calc R U . . .
H31C H 0.348825 0.798286 0.388958 0.123 Uiso 1 1 calc R U . . .
C32 C 0.4288(3) 0.8158(16) 0.7781(11) 0.044(3) Uiso 1 1 d D U . . .
H32A H 0.429354 0.911893 0.816980 0.053 Uiso 1 1 calc R U . . .
H32B H 0.424855 0.885924 0.730636 0.053 Uiso 1 1 calc R U . . .
C33 C 0.4778(4) 0.7024(18) 0.8081(10) 0.052(4) Uiso 1 1 d D U . . .
H33A H 0.478663 0.616359 0.767094 0.063 Uiso 1 1 calc R U . . .
H33B H 0.506164 0.793283 0.822167 0.063 Uiso 1 1 calc R U . . .
C34 C 0.4400(4) 0.4480(19) 0.8551(12) 0.062(4) Uiso 1 1 d D U . . .
H34A H 0.443857 0.368968 0.900511 0.075 Uiso 1 1 calc R U . . .
H34B H 0.440180 0.360012 0.814203 0.075 Uiso 1 1 calc R U . . .
C35 C 0.3905(4) 0.5562(18) 0.8270(10) 0.050(4) Uiso 1 1 d D U . . .
H35A H 0.362509 0.463019 0.810009 0.060 Uiso 1 1 calc R U . . .
H35B H 0.388681 0.634684 0.869288 0.060 Uiso 1 1 calc R U . . .
C36 C 0.5315(4) 0.481(2) 0.9073(16) 0.078(5) Uiso 1 1 d D U . . .
H36A H 0.531357 0.380877 0.870821 0.116 Uiso 1 1 calc R U . . .
H36B H 0.536319 0.420648 0.956484 0.116 Uiso 1 1 calc R U . . .
H36C H 0.558630 0.571934 0.915198 0.116 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.358(3) 0.500000 0.088(6) Uiso 1 2 d DGS . P . .
H9A H -0.020589 0.375732 0.522202 0.132 Uiso 0.5 1 d DG U P . .
H9B H 0.014697 0.469833 0.503647 0.132 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.370(2) 1.000000 0.082(5) Uiso 1 2 d DGS . P . .
H10A H -0.023832 0.299333 0.967201 0.123 Uiso 0.5 1 d DG U P . .
H10B H -0.000314 0.476255 0.975162 0.123 Uiso 0.5 1 d DG U P . .
_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 C5 1.346(11) . ?
O1 C10 1.196(12) . ?
O2 C10 1.318(10) . ?
O2 H2 0.8200 . ?
O3 C3 1.259(9) . ?
O4 C7 1.376(10) . ?
O4 C11 1.412(12) . ?
N1 C1 1.342(11) . ?
N1 C8 1.396(11) . ?
N1 C12 1.490(10) . ?
N2 C6 1.371(11) . ?
N2 C17 1.445(12) . ?
N2 C14 1.450(10) . ?
N3 C15 1.459(12) . ?
N3 C16 1.465(10) . ?
N3 C18 1.472(10) . ?
C1 C2 1.366(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.435(11) . ?
C2 C10 1.483(11) . ?
C3 C9 1.463(11) . ?
C4 C5 1.351(11) . ?
C4 C9 1.400(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(10) . ?
C6 C7 1.387(11) . ?
C7 C8 1.411(11) . ?
C8 C9 1.408(10) . ?
C11 C12 1.501(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.508(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.507(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.502(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.363(11) . ?
O5 C28 1.197(12) . ?
O6 C28 1.330(11) . ?
O6 H6 0.8200 . ?
O7 C21 1.267(10) . ?
O8 C25 1.374(9) . ?
O8 C29 1.429(12) . ?
N4 C19 1.335(12) . ?
N4 C26 1.397(11) . ?
N4 C30 1.495(10) . ?
N5 C24 1.385(11) . ?
N5 C32 1.440(10) . ?
N5 C35 1.457(12) . ?
N6 C33 1.452(12) . ?
N6 C36 1.463(11) . ?
N6 C34 1.469(11) . ?
C19 C20 1.394(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.419(12) . ?
C20 C28 1.486(12) . ?
C21 C27 1.453(11) . ?
C22 C23 1.353(11) . ?
C22 C27 1.393(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.395(11) . ?
C24 C25 1.403(12) . ?
C25 C26 1.394(11) . ?
C26 C27 1.414(10) . ?
C29 C30 1.508(11) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.510(13) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.502(10) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.497(11) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8564 . ?
O9 H9B 0.8556 . ?
O9 H9A 0.86(11) 2_556 ?
O9 H9B 0.9(3) 2_556 ?
O10 H10A 0.8568 . ?
O10 H10B 0.8559 . ?
O10 H10A 0.9(3) 2_557 ?
O10 H10B 0.9(3) 2_557 ?
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 H2 109.4 . . ?
C7 O4 C11 113.0(10) . . ?
C1 N1 C8 120.0(9) . . ?
C1 N1 C12 121.6(11) . . ?
C8 N1 C12 118.2(9) . . ?
C6 N2 C17 123.6(10) . . ?
C6 N2 C14 123.5(11) . . ?
C17 N2 C14 112.8(11) . . ?
C15 N3 C16 110.7(11) . . ?
C15 N3 C18 110.5(11) . . ?
C16 N3 C18 109.7(9) . . ?
N1 C1 C2 123.8(13) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 119.7(11) . . ?
C1 C2 C10 119.2(11) . . ?
C3 C2 C10 121.0(9) . . ?
O3 C3 C2 121.5(11) . . ?
O3 C3 C9 121.6(11) . . ?
C2 C3 C9 116.9(9) . . ?
C5 C4 C9 117.7(11) . . ?
C5 C4 H4 121.1 . . ?
C9 C4 H4 121.1 . . ?
F1 C5 C4 117.1(10) . . ?
F1 C5 C6 116.8(11) . . ?
C4 C5 C6 125.9(12) . . ?
N2 C6 C7 123.5(10) . . ?
N2 C6 C5 121.1(12) . . ?
C7 C6 C5 115.2(10) . . ?
O4 C7 C6 117.3(10) . . ?
O4 C7 C8 120.8(11) . . ?
C6 C7 C8 121.9(9) . . ?
N1 C8 C9 120.3(10) . . ?
N1 C8 C7 120.6(9) . . ?
C9 C8 C7 119.1(11) . . ?
C4 C9 C8 120.1(10) . . ?
C4 C9 C3 120.7(9) . . ?
C8 C9 C3 119.2(11) . . ?
O1 C10 O2 126.0(14) . . ?
O1 C10 C2 119.0(11) . . ?
O2 C10 C2 115.0(12) . . ?
O4 C11 C12 113.5(10) . . ?
O4 C11 H11A 108.8 . . ?
C12 C11 H11A 108.9 . . ?
O4 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N1 C12 C11 107.0(9) . . ?
N1 C12 C13 112.5(10) . . ?
C11 C12 C13 107.6(10) . . ?
N1 C12 H12 109.9 . . ?
C11 C12 H12 109.9 . . ?
C13 C12 H12 109.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.4 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 112.1(8) . . ?
N2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N3 C15 C14 109.1(11) . . ?
N3 C15 H15A 109.9 . . ?
C14 C15 H15A 109.9 . . ?
N3 C15 H15B 109.9 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N3 C16 C17 108.7(9) . . ?
N3 C16 H16A 110.0 . . ?
C17 C16 H16A 110.0 . . ?
N3 C16 H16B 109.9 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
N2 C17 C16 111.0(12) . . ?
N2 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
N2 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 112.7(10) . . ?
C19 N4 C26 120.6(10) . . ?
C19 N4 C30 122.0(11) . . ?
C26 N4 C30 117.3(10) . . ?
C24 N5 C32 124.3(11) . . ?
C24 N5 C35 120.6(10) . . ?
C32 N5 C35 114.9(11) . . ?
C33 N6 C36 110.8(12) . . ?
C33 N6 C34 109.7(12) . . ?
C36 N6 C34 111.0(10) . . ?
N4 C19 C20 122.4(13) . . ?
N4 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C19 C20 C21 120.6(11) . . ?
C19 C20 C28 116.8(11) . . ?
C21 C20 C28 122.6(10) . . ?
O7 C21 C20 122.8(11) . . ?
O7 C21 C27 120.9(11) . . ?
C20 C21 C27 116.3(9) . . ?
C23 C22 C27 118.5(11) . . ?
C23 C22 H22 120.8 . . ?
C27 C22 H22 120.8 . . ?
C22 C23 F2 118.9(10) . . ?
C22 C23 C24 125.8(13) . . ?
F2 C23 C24 115.3(11) . . ?
N5 C24 C23 123.5(12) . . ?
N5 C24 C25 121.2(10) . . ?
C23 C24 C25 115.3(10) . . ?
O8 C25 C26 122.6(11) . . ?
O8 C25 C24 116.2(10) . . ?
C26 C25 C24 121.1(9) . . ?
C25 C26 N4 120.1(9) . . ?
C25 C26 C27 120.4(11) . . ?
N4 C26 C27 119.4(10) . . ?
C22 C27 C26 118.9(11) . . ?
C22 C27 C21 120.9(9) . . ?
C26 C27 C21 120.2(11) . . ?
O5 C28 O6 124.5(13) . . ?
O5 C28 C20 122.8(12) . . ?
O6 C28 C20 112.7(12) . . ?
O8 C29 C30 111.5(11) . . ?
O8 C29 H29A 109.3 . . ?
C30 C29 H29A 109.3 . . ?
O8 C29 H29B 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
N4 C30 C29 107.4(10) . . ?
N4 C30 C31 111.8(11) . . ?
C29 C30 C31 111.7(12) . . ?
N4 C30 H30 108.7 . . ?
C29 C30 H30 108.6 . . ?
C31 C30 H30 108.6 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.4 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 109.9(9) . . ?
N5 C32 H32A 109.7 . . ?
C33 C32 H32A 109.7 . . ?
N5 C32 H32B 109.7 . . ?
C33 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
N6 C33 C32 110.7(12) . . ?
N6 C33 H33A 109.5 . . ?
C32 C33 H33A 109.5 . . ?
N6 C33 H33B 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
N6 C34 C35 111.0(10) . . ?
N6 C34 H34A 109.4 . . ?
C35 C34 H34A 109.4 . . ?
N6 C34 H34B 109.5 . . ?
C35 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
N5 C35 C34 108.8(12) . . ?
N5 C35 H35A 109.9 . . ?
C34 C35 H35A 110.0 . . ?
N5 C35 H35B 109.9 . . ?
C34 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
N6 C36 H36A 109.4 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 104.8 . . ?
H9A O9 H9A 164.2 . 2_556 ?
H9B O9 H9A 60.1 . 2_556 ?
H9A O9 H9B 60.1 . 2_556 ?
H9B O9 H9B 55.7 . 2_556 ?
H9A O9 H9B 104.8 2_556 2_556 ?
H10A O10 H10B 104.8 . . ?
H10A O10 H10A 112.0 . 2_557 ?
H10B O10 H10A 133.5 . 2_557 ?
H10A O10 H10B 133.5 . 2_557 ?
H10B O10 H10B 64.9 . 2_557 ?
H10A O10 H10B 104.8 2_557 2_557 ?
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
C8 N1 C1 C2 -0.4(18) . . . . ?
C12 N1 C1 C2 175.2(11) . . . . ?
N1 C1 C2 C3 -0.3(18) . . . . ?
N1 C1 C2 C10 178.2(11) . . . . ?
C1 C2 C3 O3 -179.9(10) . . . . ?
C10 C2 C3 O3 1.6(17) . . . . ?
C1 C2 C3 C9 0.1(16) . . . . ?
C10 C2 C3 C9 -178.3(10) . . . . ?
C9 C4 C5 F1 -175.8(10) . . . . ?
C9 C4 C5 C6 -1(2) . . . . ?
C17 N2 C6 C7 134.2(13) . . . . ?
C14 N2 C6 C7 -45.3(18) . . . . ?
C17 N2 C6 C5 -41.7(19) . . . . ?
C14 N2 C6 C5 138.8(12) . . . . ?
F1 C5 C6 N2 -9.6(18) . . . . ?
C4 C5 C6 N2 175.5(12) . . . . ?
F1 C5 C6 C7 174.2(10) . . . . ?
C4 C5 C6 C7 -0.7(19) . . . . ?
C11 O4 C7 C6 -155.6(11) . . . . ?
C11 O4 C7 C8 24.0(15) . . . . ?
N2 C6 C7 O4 4.5(17) . . . . ?
C5 C6 C7 O4 -179.4(10) . . . . ?
N2 C6 C7 C8 -175.1(11) . . . . ?
C5 C6 C7 C8 1.0(17) . . . . ?
C1 N1 C8 C9 1.2(17) . . . . ?
C12 N1 C8 C9 -174.5(9) . . . . ?
C1 N1 C8 C7 -178.6(10) . . . . ?
C12 N1 C8 C7 5.7(16) . . . . ?
O4 C7 C8 N1 0.5(17) . . . . ?
C6 C7 C8 N1 -180.0(10) . . . . ?
O4 C7 C8 C9 -179.3(10) . . . . ?
C6 C7 C8 C9 0.2(17) . . . . ?
C5 C4 C9 C8 2.2(17) . . . . ?
C5 C4 C9 C3 -178.1(10) . . . . ?
N1 C8 C9 C4 178.3(10) . . . . ?
C7 C8 C9 C4 -1.9(16) . . . . ?
N1 C8 C9 C3 -1.4(16) . . . . ?
C7 C8 C9 C3 178.4(10) . . . . ?
O3 C3 C9 C4 1.1(16) . . . . ?
C2 C3 C9 C4 -178.9(11) . . . . ?
O3 C3 C9 C8 -179.3(11) . . . . ?
C2 C3 C9 C8 0.7(15) . . . . ?
C1 C2 C10 O1 0.0(19) . . . . ?
C3 C2 C10 O1 178.4(12) . . . . ?
C1 C2 C10 O2 177.8(11) . . . . ?
C3 C2 C10 O2 -3.8(17) . . . . ?
C7 O4 C11 C12 -54.7(13) . . . . ?
C1 N1 C12 C11 151.7(11) . . . . ?
C8 N1 C12 C11 -32.7(14) . . . . ?
C1 N1 C12 C13 33.6(15) . . . . ?
C8 N1 C12 C13 -150.7(11) . . . . ?
O4 C11 C12 N1 57.9(13) . . . . ?
O4 C11 C12 C13 179.1(9) . . . . ?
C6 N2 C14 C15 127.2(15) . . . . ?
C17 N2 C14 C15 -52.4(18) . . . . ?
C16 N3 C15 C14 -59.7(13) . . . . ?
C18 N3 C15 C14 178.5(12) . . . . ?
N2 C14 C15 N3 54.3(17) . . . . ?
C15 N3 C16 C17 61.6(16) . . . . ?
C18 N3 C16 C17 -176.1(16) . . . . ?
C6 N2 C17 C16 -125.7(13) . . . . ?
C14 N2 C17 C16 53.9(15) . . . . ?
N3 C16 C17 N2 -57.7(18) . . . . ?
C26 N4 C19 C20 -3.6(17) . . . . ?
C30 N4 C19 C20 173.3(10) . . . . ?
N4 C19 C20 C21 -3.4(18) . . . . ?
N4 C19 C20 C28 177.7(10) . . . . ?
C19 C20 C21 O7 -177.2(11) . . . . ?
C28 C20 C21 O7 1.6(18) . . . . ?
C19 C20 C21 C27 5.4(16) . . . . ?
C28 C20 C21 C27 -175.8(10) . . . . ?
C27 C22 C23 F2 175.5(9) . . . . ?
C27 C22 C23 C24 -2.9(19) . . . . ?
C32 N5 C24 C23 -129.4(13) . . . . ?
C35 N5 C24 C23 45.3(18) . . . . ?
C32 N5 C24 C25 49.5(17) . . . . ?
C35 N5 C24 C25 -135.8(12) . . . . ?
C22 C23 C24 N5 -177.5(11) . . . . ?
F2 C23 C24 N5 4.0(18) . . . . ?
C22 C23 C24 C25 3.5(18) . . . . ?
F2 C23 C24 C25 -174.9(9) . . . . ?
C29 O8 C25 C26 21.9(15) . . . . ?
C29 O8 C25 C24 -162.2(9) . . . . ?
N5 C24 C25 O8 2.1(16) . . . . ?
C23 C24 C25 O8 -178.9(10) . . . . ?
N5 C24 C25 C26 178.0(10) . . . . ?
C23 C24 C25 C26 -3.0(16) . . . . ?
O8 C25 C26 N4 2.1(17) . . . . ?
C24 C25 C26 N4 -173.6(10) . . . . ?
O8 C25 C26 C27 177.7(10) . . . . ?
C24 C25 C26 C27 2.0(16) . . . . ?
C19 N4 C26 C25 -176.3(10) . . . . ?
C30 N4 C26 C25 6.7(15) . . . . ?
C19 N4 C26 C27 8.0(16) . . . . ?
C30 N4 C26 C27 -169.0(9) . . . . ?
C23 C22 C27 C26 1.6(16) . . . . ?
C23 C22 C27 C21 -178.3(10) . . . . ?
C25 C26 C27 C22 -1.2(16) . . . . ?
N4 C26 C27 C22 174.4(10) . . . . ?
C25 C26 C27 C21 178.7(10) . . . . ?
N4 C26 C27 C21 -5.7(15) . . . . ?
O7 C21 C27 C22 1.6(16) . . . . ?
C20 C21 C27 C22 179.0(10) . . . . ?
O7 C21 C27 C26 -178.3(10) . . . . ?
C20 C21 C27 C26 -0.9(15) . . . . ?
C19 C20 C28 O5 0(2) . . . . ?
C21 C20 C28 O5 -178.4(13) . . . . ?
C19 C20 C28 O6 179.1(11) . . . . ?
C21 C20 C28 O6 0.3(17) . . . . ?
C25 O8 C29 C30 -53.6(12) . . . . ?
C19 N4 C30 C29 147.1(11) . . . . ?
C26 N4 C30 C29 -35.9(14) . . . . ?
C19 N4 C30 C31 24.3(16) . . . . ?
C26 N4 C30 C31 -158.7(11) . . . . ?
O8 C29 C30 N4 59.8(13) . . . . ?
O8 C29 C30 C31 -177.3(10) . . . . ?
C24 N5 C32 C33 -131.0(14) . . . . ?
C35 N5 C32 C33 54.1(18) . . . . ?
C36 N6 C33 C32 -177.9(13) . . . . ?
C34 N6 C33 C32 59.2(14) . . . . ?
N5 C32 C33 N6 -55.5(17) . . . . ?
C33 N6 C34 C35 -60.0(17) . . . . ?
C36 N6 C34 C35 177.2(16) . . . . ?
C24 N5 C35 C34 130.7(13) . . . . ?
C32 N5 C35 C34 -54.1(16) . . . . ?
N6 C34 C35 N5 55.7(19) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.93 2.48(2) 124.5 . yes
O6 H6 O7 0.82 1.73 2.50(2) 155.3 . yes
O10 H10A N6 0.86 2.30 2.893(18) 126.7 3_445 yes
O9 H9A N3 0.86 2.54 2.924(18) 108.2 . yes
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.083
_cell_measurement_pressure       0.29


# start Validation Reply Form
_vrf_ATOM007_LH_PE_0p29          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_PE_0p29          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_PE_0p29          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_PE_0p29          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_PE_0p29          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_PE_0p29          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_PE_0p29          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_PE_0p29          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_PE_0p29          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT111_LH_PE_1p26          
;
RESPONSE: The structure is chiral.
;
_vrf_PLAT420_LH_ME_0p29          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT721_LH_PE_0p29          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints

;
_vrf_PLAT910_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_PE_0p29          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_PE_0p29          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_PE_0p29          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_PE_0p29          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_OFLO_AMBIENT
_database_code_depnum_ccdc_archive 'CCDC 2481338'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_280422_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   30.251(10)
_cell_length_b                   6.8318(8)
_cell_length_c                   16.845(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.15(2)
_cell_angle_gamma                90
_cell_volume                     3360.3(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5571
_cell_measurement_theta_min      2.505
_cell_measurement_theta_max      23.320
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6250
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            5571
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         23.320
_diffrn_reflns_theta_full        23.320
_diffrn_measured_fraction_theta_max 0.338
_diffrn_measured_fraction_theta_full 0.338
_diffrn_reflns_Laue_measured_fraction_max 0.338
_diffrn_reflns_Laue_measured_fraction_full 0.338
_diffrn_reflns_point_group_measured_fraction_max 0.338
_diffrn_reflns_point_group_measured_fraction_full 0.338
_reflns_number_total             826
_reflns_number_gt                450
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+2.7240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         826
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      0.899
_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
F1 F 0.5692(3) 0.7039(5) 0.7763(2) 0.074(7) Uani 1 1 d D . . . .
O1 O 0.6440(4) 0.6193(7) 0.5651(3) 0.059(5) Uani 1 1 d D . . . .
O4 O 0.4393(4) 0.7992(6) 0.2722(3) 0.062(7) Uani 1 1 d D . . . .
C11 C 0.5229(5) 0.7323(10) 0.5551(4) 0.042(5) Uani 1 1 d D . . . .
O2 O 0.4444(4) 0.8125(7) 0.5178(3) 0.058(6) Uani 1 1 d D . . . .
N3 N 0.5612(5) 0.6967(9) 0.4471(4) 0.044(5) Uani 1 1 d D . . . .
N1 N 0.6474(5) 0.6309(10) 0.7343(4) 0.047(5) Uani 1 1 d D . . . .
C7 C 0.5663(6) 0.6995(12) 0.6928(5) 0.039(5) Uani 1 1 d D . . . .
C10 C 0.5624(6) 0.6919(10) 0.5306(5) 0.042(5) Uani 1 1 d D . . . .
C3 C 0.5214(7) 0.7357(13) 0.3918(6) 0.046(6) Uani 1 1 d D . . . .
H3 H 0.521153 0.738781 0.336500 0.056 Uiso 1 1 calc R U . . .
C8 C 0.6077(6) 0.6587(11) 0.6725(5) 0.041(5) Uani 1 1 d D . . . .
O3 O 0.4027(5) 0.8547(7) 0.3683(4) 0.063(6) Uani 1 1 d D . . . .
H3A H 0.407853 0.842018 0.418253 0.094 Uiso 1 1 calc R U . . .
C4 C 0.4815(6) 0.7706(11) 0.4117(5) 0.047(5) Uani 1 1 d D . . . .
C6 C 0.5240(6) 0.7356(12) 0.6393(5) 0.047(6) Uani 1 1 d D . . . .
H6 H 0.498105 0.760368 0.657543 0.057 Uiso 1 1 calc R U . . .
C9 C 0.6040(5) 0.6528(11) 0.5879(5) 0.043(5) Uani 1 1 d D . . . .
N2 N 0.7388(5) 0.6185(11) 0.8370(4) 0.081(7) Uani 1 1 d D . . . .
C13 C 0.4397(6) 0.8066(12) 0.3447(5) 0.051(6) Uani 1 1 d D . . . .
C16 C 0.7071(5) 0.7712(12) 0.8445(5) 0.072(7) Uani 1 1 d D . . . .
H16A H 0.724137 0.890508 0.862527 0.086 Uiso 1 1 calc R U . . .
H16B H 0.692015 0.733968 0.886417 0.086 Uiso 1 1 calc R U . . .
C5 C 0.4788(5) 0.7745(10) 0.4954(5) 0.043(5) Uani 1 1 d D . . . .
C1 C 0.6361(5) 0.5448(9) 0.4815(4) 0.060(7) Uani 1 1 d D . . . .
H1A H 0.622258 0.415844 0.477833 0.072 Uiso 1 1 calc R U . . .
H1B H 0.664983 0.533360 0.467049 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6269(6) 0.8836(9) 0.4218(4) 0.060(9) Uani 1 1 d D . . . .
H12A H 0.605697 0.970176 0.386069 0.090 Uiso 1 1 calc R U . . .
H12B H 0.653872 0.870142 0.402253 0.090 Uiso 1 1 calc R U . . .
H12C H 0.635167 0.936368 0.476473 0.090 Uiso 1 1 calc R U . . .
C2 C 0.6046(6) 0.6831(10) 0.4225(5) 0.048(6) Uani 1 1 d D . . . .
H2 H 0.598093 0.627509 0.367035 0.058 Uiso 1 1 calc R U . . .
C17 C 0.6718(5) 0.8112(11) 0.7670(4) 0.069(7) Uani 1 1 d D . . . .
H17A H 0.650219 0.906837 0.777010 0.083 Uiso 1 1 calc R U . . .
H17B H 0.686260 0.865548 0.726792 0.083 Uiso 1 1 calc R U . . .
C15 C 0.7143(5) 0.4429(11) 0.8072(4) 0.066(6) Uani 1 1 d D . . . .
H15A H 0.699280 0.395248 0.847811 0.079 Uiso 1 1 calc R U . . .
H15B H 0.735724 0.343444 0.799795 0.079 Uiso 1 1 calc R U . . .
C18 C 0.7737(6) 0.5827(13) 0.9120(5) 0.112(8) Uani 1 1 d D . . . .
H18A H 0.790472 0.701270 0.929478 0.168 Uiso 1 1 calc R U . . .
H18B H 0.794267 0.483592 0.902556 0.168 Uiso 1 1 calc R U . . .
H18C H 0.759707 0.539403 0.953865 0.168 Uiso 1 1 calc R U . . .
C14 C 0.6795(5) 0.4749(11) 0.7283(4) 0.066(6) Uani 1 1 d D . . . .
H14A H 0.694811 0.508777 0.686211 0.079 Uiso 1 1 calc R U . . .
H14B H 0.662672 0.354425 0.711729 0.079 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 C7 1.386(7) . ?
O1 C9 1.381(14) . ?
O1 C1 1.456(7) . ?
O4 C13 1.220(7) . ?
C11 C10 1.391(13) . ?
C11 C6 1.411(8) . ?
C11 C5 1.473(11) . ?
O2 C5 1.225(13) . ?
N3 C3 1.344(16) . ?
N3 C10 1.397(8) . ?
N3 C2 1.479(16) . ?
N1 C8 1.380(18) . ?
N1 C14 1.464(12) . ?
N1 C17 1.468(11) . ?
C7 C6 1.380(17) . ?
C7 C8 1.410(19) . ?
C10 C9 1.396(16) . ?
C3 C4 1.355(18) . ?
C3 H3 0.9300 . ?
C8 C9 1.402(9) . ?
O3 C13 1.322(16) . ?
O3 H3A 0.8200 . ?
C4 C5 1.434(10) . ?
C4 C13 1.480(15) . ?
C6 H6 0.9300 . ?
N2 C15 1.431(12) . ?
N2 C18 1.440(10) . ?
N2 C16 1.444(13) . ?
C16 C17 1.479(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.514(15) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.528(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.480(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 113.0(10) . . ?
C10 C11 C6 120.3(11) . . ?
C10 C11 C5 122.1(7) . . ?
C6 C11 C5 117.6(10) . . ?
C3 N3 C10 119.0(12) . . ?
C3 N3 C2 121.2(7) . . ?
C10 N3 C2 119.3(12) . . ?
C8 N1 C14 120.7(8) . . ?
C8 N1 C17 114.9(8) . . ?
C14 N1 C17 111.0(12) . . ?
C6 C7 F1 117.4(11) . . ?
C6 C7 C8 127.4(8) . . ?
F1 C7 C8 115.2(12) . . ?
C11 C10 C9 121.5(7) . . ?
C11 C10 N3 119.7(11) . . ?
C9 C10 N3 118.8(11) . . ?
N3 C3 C4 123.9(8) . . ?
N3 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
N1 C8 C9 125.9(14) . . ?
N1 C8 C7 119.8(7) . . ?
C9 C8 C7 114.4(13) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 122.0(13) . . ?
C3 C4 C13 118.7(8) . . ?
C5 C4 C13 119.3(12) . . ?
C7 C6 C11 115.4(12) . . ?
C7 C6 H6 122.3 . . ?
C11 C6 H6 122.3 . . ?
O1 C9 C10 122.5(7) . . ?
O1 C9 C8 116.4(12) . . ?
C10 C9 C8 121.0(12) . . ?
C15 N2 C18 111.1(8) . . ?
C15 N2 C16 109.9(11) . . ?
C18 N2 C16 113.5(7) . . ?
O4 C13 O3 121.6(14) . . ?
O4 C13 C4 122.6(12) . . ?
O3 C13 C4 115.8(8) . . ?
N2 C16 C17 113.5(7) . . ?
N2 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N2 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
O2 C5 C4 125.3(13) . . ?
O2 C5 C11 121.5(8) . . ?
C4 C5 C11 113.2(11) . . ?
O1 C1 C2 109.4(6) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C1 107.9(7) . . ?
N3 C2 C12 111.8(9) . . ?
C1 C2 C12 111.2(12) . . ?
N3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C12 C2 H2 108.6 . . ?
N1 C17 C16 110.7(8) . . ?
N1 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N2 C15 C14 111.9(7) . . ?
N2 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 112.0(7) . . ?
N1 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C11 C10 C9 0.3(12) . . . . ?
C5 C11 C10 C9 179.8(9) . . . . ?
C6 C11 C10 N3 -177.5(7) . . . . ?
C5 C11 C10 N3 2.0(11) . . . . ?
C3 N3 C10 C11 -1.7(13) . . . . ?
C2 N3 C10 C11 170.9(7) . . . . ?
C3 N3 C10 C9 -179.5(9) . . . . ?
C2 N3 C10 C9 -7.0(12) . . . . ?
C10 N3 C3 C4 -0.2(16) . . . . ?
C2 N3 C3 C4 -172.6(8) . . . . ?
C14 N1 C8 C9 -42.8(14) . . . . ?
C17 N1 C8 C9 94.5(10) . . . . ?
C14 N1 C8 C7 138.1(9) . . . . ?
C17 N1 C8 C7 -84.6(11) . . . . ?
C6 C7 C8 N1 178.3(9) . . . . ?
F1 C7 C8 N1 -1.4(13) . . . . ?
C6 C7 C8 C9 -0.9(15) . . . . ?
F1 C7 C8 C9 179.4(6) . . . . ?
N3 C3 C4 C5 1.8(16) . . . . ?
N3 C3 C4 C13 -178.4(9) . . . . ?
F1 C7 C6 C11 179.2(5) . . . . ?
C8 C7 C6 C11 -0.6(16) . . . . ?
C10 C11 C6 C7 0.9(12) . . . . ?
C5 C11 C6 C7 -178.6(8) . . . . ?
C1 O1 C9 C10 -25.3(11) . . . . ?
C1 O1 C9 C8 158.8(6) . . . . ?
C11 C10 C9 O1 -177.6(6) . . . . ?
N3 C10 C9 O1 0.2(13) . . . . ?
C11 C10 C9 C8 -1.9(13) . . . . ?
N3 C10 C9 C8 175.9(6) . . . . ?
N1 C8 C9 O1 -1.1(12) . . . . ?
C7 C8 C9 O1 178.1(7) . . . . ?
N1 C8 C9 C10 -177.1(9) . . . . ?
C7 C8 C9 C10 2.1(13) . . . . ?
C3 C4 C13 O4 2.6(14) . . . . ?
C5 C4 C13 O4 -177.6(7) . . . . ?
C3 C4 C13 O3 -175.0(8) . . . . ?
C5 C4 C13 O3 4.8(12) . . . . ?
C15 N2 C16 C17 -56.3(9) . . . . ?
C18 N2 C16 C17 178.7(9) . . . . ?
C3 C4 C5 O2 177.0(9) . . . . ?
C13 C4 C5 O2 -2.7(14) . . . . ?
C3 C4 C5 C11 -1.4(13) . . . . ?
C13 C4 C5 C11 178.8(7) . . . . ?
C10 C11 C5 O2 -179.0(8) . . . . ?
C6 C11 C5 O2 0.5(12) . . . . ?
C10 C11 C5 C4 -0.5(11) . . . . ?
C6 C11 C5 C4 179.0(7) . . . . ?
C9 O1 C1 C2 55.0(10) . . . . ?
C3 N3 C2 C1 -151.6(9) . . . . ?
C10 N3 C2 C1 36.0(9) . . . . ?
C3 N3 C2 C12 85.8(11) . . . . ?
C10 N3 C2 C12 -86.6(10) . . . . ?
O1 C1 C2 N3 -59.1(10) . . . . ?
O1 C1 C2 C12 63.8(11) . . . . ?
C8 N1 C17 C16 166.8(9) . . . . ?
C14 N1 C17 C16 -51.9(8) . . . . ?
N2 C16 C17 N1 54.5(11) . . . . ?
C18 N2 C15 C14 -177.6(8) . . . . ?
C16 N2 C15 C14 56.0(9) . . . . ?
C8 N1 C14 C15 -167.9(9) . . . . ?
C17 N1 C14 C15 53.3(9) . . . . ?
N2 C15 C14 N1 -56.0(11) . . . . ?
_refine_diff_density_max         0.083
_refine_diff_density_min         -0.089
_refine_diff_density_rms         0.023
_cell_measurement_pressure       0.0


# start Validation Reply Form
_vrf_ATOM007_OFLO_AMBIENT        
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_AMBIENT        
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_AMBIENT        
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_AMBIENT        
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_AMBIENT        
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_AMBIENT        
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_AMBIENT        
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_AMBIENT        
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_AMBIENT        
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_AMBIENT        
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_AMBIENT        
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_AMBIENT        
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_AMBIENT        
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_OFLO_5p2
_database_code_depnum_ccdc_archive 'CCDC 2481348'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_300522_run1_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   28.443(9)
_cell_length_b                   6.0167(7)
_cell_length_c                   15.7781(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.951(18)
_cell_angle_gamma                90
_cell_volume                     2631.5(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3791
_cell_measurement_theta_min      2.649
_cell_measurement_theta_max      23.285
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6691
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            3791
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.649
_diffrn_reflns_theta_max         23.285
_diffrn_reflns_theta_full        23.285
_diffrn_measured_fraction_theta_max 0.350
_diffrn_measured_fraction_theta_full 0.350
_diffrn_reflns_Laue_measured_fraction_max 0.350
_diffrn_reflns_Laue_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.350
_diffrn_reflns_point_group_measured_fraction_full 0.350
_reflns_number_total             666
_reflns_number_gt                469
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.3586P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         666
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      0.866
_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
F1 F 0.5705(2) 0.7006(4) 0.79277(16) 0.028(5) Uani 1 1 d D . . . .
O1 O 0.6501(4) 0.5807(5) 0.5668(2) 0.033(4) Uani 1 1 d D . . . .
O4 O 0.4341(3) 0.8178(4) 0.2664(2) 0.022(5) Uani 1 1 d D . . . .
C11 C 0.5247(4) 0.7259(8) 0.5617(3) 0.024(4) Uani 1 1 d D . . . .
O2 O 0.4420(3) 0.8249(5) 0.5270(2) 0.025(4) Uani 1 1 d D . . . .
N3 N 0.5632(4) 0.6827(7) 0.4436(3) 0.024(4) Uani 1 1 d D . . . .
N1 N 0.6520(4) 0.5984(6) 0.7472(3) 0.024(4) Uani 1 1 d D . . . .
C7 C 0.5681(5) 0.6871(9) 0.7058(4) 0.021(4) Uani 1 1 d D . . . .
C10 C 0.5659(5) 0.6756(8) 0.5327(3) 0.021(4) Uani 1 1 d D . . . .
C3 C 0.5222(6) 0.7308(9) 0.3866(4) 0.022(4) Uani 1 1 d D . . . .
H3 H 0.522368 0.734881 0.327760 0.026 Uiso 1 1 calc R U . . .
C8 C 0.6101(5) 0.6305(8) 0.6811(4) 0.019(4) Uani 1 1 d D . . . .
O3 O 0.3980(4) 0.8782(5) 0.3748(2) 0.032(5) Uani 1 1 d D . . . .
H3A H 0.403712 0.857604 0.427480 0.048 Uiso 1 1 calc R U . . .
C4 C 0.4806(5) 0.7736(8) 0.4110(3) 0.021(4) Uani 1 1 d D . . . .
C6 C 0.5256(5) 0.7342(8) 0.6517(3) 0.020(4) Uani 1 1 d D . . . .
H6 H 0.498354 0.770282 0.672280 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6077(5) 0.6249(8) 0.5913(4) 0.024(4) Uani 1 1 d D . . . .
N2 N 0.7477(3) 0.5911(6) 0.8424(2) 0.026(5) Uani 1 1 d D . . . .
C13 C 0.4360(5) 0.8239(8) 0.3450(4) 0.027(5) Uani 1 1 d D . . . .
C16 C 0.7168(4) 0.7747(8) 0.8518(3) 0.028(5) Uani 1 1 d D . . . .
H16A H 0.736054 0.908894 0.864264 0.034 Uiso 1 1 calc R U . . .
H16B H 0.702006 0.746829 0.900466 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4789(4) 0.7771(8) 0.5008(3) 0.020(4) Uani 1 1 d D . . . .
C1 C 0.6437(4) 0.5184(7) 0.4769(3) 0.029(5) Uani 1 1 d D . . . .
H1A H 0.630720 0.368895 0.468824 0.034 Uiso 1 1 calc R U . . .
H1B H 0.674808 0.518274 0.461246 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6314(5) 0.9047(7) 0.4203(3) 0.027(6) Uani 1 1 d D . . . .
H12A H 0.610132 0.999123 0.380007 0.040 Uiso 1 1 calc R U . . .
H12B H 0.662118 0.896996 0.404735 0.040 Uiso 1 1 calc R U . . .
H12C H 0.635633 0.964272 0.477992 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6101(5) 0.6757(8) 0.4176(3) 0.025(5) Uani 1 1 d D . . . .
H2 H 0.604690 0.619445 0.357935 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6781(4) 0.8088(7) 0.7706(3) 0.026(5) Uani 1 1 d D . . . .
H17A H 0.655801 0.922856 0.780552 0.031 Uiso 1 1 calc R U . . .
H17B H 0.692412 0.857138 0.723483 0.031 Uiso 1 1 calc R U . . .
C15 C 0.7203(4) 0.3868(7) 0.8186(3) 0.024(5) Uani 1 1 d D . . . .
H15A H 0.704164 0.346047 0.864429 0.028 Uiso 1 1 calc R U . . .
H15B H 0.742082 0.267206 0.812146 0.028 Uiso 1 1 calc R U . . .
C18 C 0.7845(4) 0.5575(9) 0.9223(3) 0.035(6) Uani 1 1 d D . . . .
H18A H 0.802757 0.691790 0.936689 0.052 Uiso 1 1 calc R U . . .
H18B H 0.805621 0.439258 0.913905 0.052 Uiso 1 1 calc R U . . .
H18C H 0.769233 0.519517 0.968834 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6838(4) 0.4181(7) 0.7355(3) 0.028(5) Uani 1 1 d D . . . .
H14A H 0.699788 0.453556 0.688908 0.033 Uiso 1 1 calc R U . . .
H14B H 0.665393 0.282584 0.720208 0.033 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 C7 1.361(5) . ?
O1 C9 1.372(13) . ?
O1 C1 1.439(5) . ?
O4 C13 1.230(6) . ?
C11 C10 1.384(12) . ?
C11 C6 1.416(6) . ?
C11 C5 1.468(10) . ?
O2 C5 1.245(11) . ?
N3 C3 1.335(15) . ?
N3 C10 1.392(6) . ?
N3 C2 1.480(15) . ?
N1 C8 1.411(14) . ?
N1 C14 1.450(10) . ?
N1 C17 1.471(8) . ?
C7 C6 1.344(14) . ?
C7 C8 1.380(16) . ?
C10 C9 1.366(14) . ?
C3 C4 1.348(16) . ?
C3 H3 0.9300 . ?
C8 C9 1.403(7) . ?
O3 C13 1.313(13) . ?
O3 H3A 0.8200 . ?
C4 C5 1.430(7) . ?
C4 C13 1.482(14) . ?
C6 H6 0.9300 . ?
N2 C16 1.439(9) . ?
N2 C15 1.458(9) . ?
N2 C18 1.461(8) . ?
C16 C17 1.505(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.511(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.502(9) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.491(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 113.9(8) . . ?
C10 C11 C6 120.8(9) . . ?
C10 C11 C5 121.6(5) . . ?
C6 C11 C5 117.6(8) . . ?
C3 N3 C10 121.9(10) . . ?
C3 N3 C2 121.7(5) . . ?
C10 N3 C2 115.5(10) . . ?
C8 N1 C14 117.1(5) . . ?
C8 N1 C17 111.3(5) . . ?
C14 N1 C17 112.5(8) . . ?
C6 C7 F1 117.6(9) . . ?
C6 C7 C8 125.8(6) . . ?
F1 C7 C8 116.6(10) . . ?
C9 C10 C11 119.9(5) . . ?
C9 C10 N3 122.1(10) . . ?
C11 C10 N3 117.9(10) . . ?
N3 C3 C4 122.7(6) . . ?
N3 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C7 C8 C9 116.2(11) . . ?
C7 C8 N1 117.9(6) . . ?
C9 C8 N1 125.8(11) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.9(10) . . ?
C3 C4 C13 120.5(6) . . ?
C5 C4 C13 118.6(10) . . ?
C7 C6 C11 116.2(9) . . ?
C7 C6 H6 121.9 . . ?
C11 C6 H6 121.9 . . ?
C10 C9 O1 122.6(5) . . ?
C10 C9 C8 121.0(10) . . ?
O1 C9 C8 116.3(10) . . ?
C16 N2 C15 111.8(8) . . ?
C16 N2 C18 110.7(4) . . ?
C15 N2 C18 110.1(4) . . ?
O4 C13 O3 121.0(10) . . ?
O4 C13 C4 122.7(9) . . ?
O3 C13 C4 116.4(6) . . ?
N2 C16 C17 111.4(4) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O2 C5 C4 123.6(10) . . ?
O2 C5 C11 121.4(5) . . ?
C4 C5 C11 115.0(9) . . ?
O1 C1 C2 111.6(5) . . ?
O1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C12 110.4(7) . . ?
N3 C2 C1 109.3(5) . . ?
C12 C2 C1 111.2(10) . . ?
N3 C2 H2 108.6 . . ?
C12 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
N1 C17 C16 109.2(5) . . ?
N1 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N1 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
N2 C15 C14 110.2(4) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 108.2(5) . . ?
N1 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
N1 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
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
C6 C11 C10 C9 2.5(8) . . . . ?
C5 C11 C10 C9 -178.8(6) . . . . ?
C6 C11 C10 N3 -176.4(5) . . . . ?
C5 C11 C10 N3 2.3(8) . . . . ?
C3 N3 C10 C9 179.5(6) . . . . ?
C2 N3 C10 C9 -11.5(8) . . . . ?
C3 N3 C10 C11 -1.6(9) . . . . ?
C2 N3 C10 C11 167.4(5) . . . . ?
C10 N3 C3 C4 -0.6(10) . . . . ?
C2 N3 C3 C4 -169.0(6) . . . . ?
C6 C7 C8 C9 0.7(10) . . . . ?
F1 C7 C8 C9 -177.7(4) . . . . ?
C6 C7 C8 N1 176.6(6) . . . . ?
F1 C7 C8 N1 -1.9(8) . . . . ?
C14 N1 C8 C7 141.0(7) . . . . ?
C17 N1 C8 C7 -87.6(7) . . . . ?
C14 N1 C8 C9 -43.7(8) . . . . ?
C17 N1 C8 C9 87.7(7) . . . . ?
N3 C3 C4 C5 2.2(10) . . . . ?
N3 C3 C4 C13 -179.4(6) . . . . ?
F1 C7 C6 C11 177.9(4) . . . . ?
C8 C7 C6 C11 -0.5(10) . . . . ?
C10 C11 C6 C7 -1.1(9) . . . . ?
C5 C11 C6 C7 -179.8(5) . . . . ?
C11 C10 C9 O1 -177.9(5) . . . . ?
N3 C10 C9 O1 1.0(9) . . . . ?
C11 C10 C9 C8 -2.3(9) . . . . ?
N3 C10 C9 C8 176.6(5) . . . . ?
C1 O1 C9 C10 -20.0(7) . . . . ?
C1 O1 C9 C8 164.3(4) . . . . ?
C7 C8 C9 C10 0.7(9) . . . . ?
N1 C8 C9 C10 -174.7(6) . . . . ?
C7 C8 C9 O1 176.5(6) . . . . ?
N1 C8 C9 O1 1.1(8) . . . . ?
C3 C4 C13 O4 3.9(9) . . . . ?
C5 C4 C13 O4 -177.7(5) . . . . ?
C3 C4 C13 O3 -175.6(6) . . . . ?
C5 C4 C13 O3 2.8(8) . . . . ?
C15 N2 C16 C17 -55.7(6) . . . . ?
C18 N2 C16 C17 -178.9(5) . . . . ?
C3 C4 C5 O2 176.8(6) . . . . ?
C13 C4 C5 O2 -1.6(9) . . . . ?
C3 C4 C5 C11 -1.5(8) . . . . ?
C13 C4 C5 C11 -179.9(5) . . . . ?
C10 C11 C5 O2 -179.1(6) . . . . ?
C6 C11 C5 O2 -0.4(8) . . . . ?
C10 C11 C5 C4 -0.8(8) . . . . ?
C6 C11 C5 C4 177.9(5) . . . . ?
C9 O1 C1 C2 47.9(8) . . . . ?
C3 N3 C2 C12 84.5(8) . . . . ?
C10 N3 C2 C12 -84.5(7) . . . . ?
C3 N3 C2 C1 -152.9(5) . . . . ?
C10 N3 C2 C1 38.1(6) . . . . ?
O1 C1 C2 N3 -56.8(8) . . . . ?
O1 C1 C2 C12 65.4(10) . . . . ?
C8 N1 C17 C16 169.5(6) . . . . ?
C14 N1 C17 C16 -56.8(6) . . . . ?
N2 C16 C17 N1 53.5(8) . . . . ?
C16 N2 C15 C14 58.5(6) . . . . ?
C18 N2 C15 C14 -178.0(5) . . . . ?
C8 N1 C14 C15 -169.6(6) . . . . ?
C17 N1 C14 C15 59.6(6) . . . . ?
N2 C15 C14 N1 -59.0(8) . . . . ?
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.028
_cell_measurement_pressure       5.2

# start Validation Reply Form
_vrf_ATOM007_OFLO_5p2            
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_5p2            
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_5p2            
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_5p2            
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_5p2            
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_5p2            
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_5p2            
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_5p2            
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_5p2            
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_5p2            
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_5p2            
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_5p2            
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_5p2            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;

# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_levo_hh_20241120_11_0m
_database_code_depnum_ccdc_archive 'CCDC 2481337'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_levo_hh_20241120_11_0m 
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: The structure was refined isotropically due to the number of data for pressure structure determination
;
_vrf_PLAT029_levo_hh_20241120_11_0m 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.345 Why?
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available This is exacerbated by the structure being P1.
;
_vrf_PLAT089_levo_hh_20241120_11_0m 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax <= 18) .......       3.37 Note
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data
;
_vrf_PLAT201_levo_hh_20241120_11_0m 
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......        104 Report
RESPONSE: High pressure dataset
;
_vrf_PLAT340_levo_hh_20241120_11_0m 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.05273 Ang.
RESPONSE: High pressure dataset
;
_vrf_PLAT415_levo_hh_20241120_11_0m 
;
PROBLEM: Short Inter D-H..H-X       H17C     ..H29B     .       1.84 Ang.
RESPONSE: High pressure dataset
;
_vrf_THETM01_levo_hh_20241120_11_0m 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: High-pressure dataset
;
_vrf_PLAT035_levo_hh_20241120_11_0m 
;
PROBLEM: _chemical_absolute_configuration Info  Not Given     Please Do !
RESPONSE: This is a known Form of Levofloxacin
;
_vrf_PLAT911_levo_hh_20241120_11_0m 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.556       2486 Report
RESPONSE: The sample is housed in a Diamond anvil cell that restricts  available data.
;
_vrf_PLAT915_levo_hh_20241120_11_0m 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         33 %
RESPONSE: The sample is housed in a Diamond anvil cell that restricts  available data.
;
# Added during the CSD deposition process: Wednesday 08 October 2025 03:22 PM
# end Validation Reply Form

_audit_creation_date             2025-09-25
_audit_creation_method           
;
Olex2 1.5-ac7-013
(compiled 2025.01.02 svn.rf662f148 for Rigaku Oxford Diffraction, GUI svn.r7109)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.5(H2 O)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

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

_cell_length_a                   13.985(2)
_cell_length_b                   6.0616(6)
_cell_length_c                   17.534(3)
_cell_angle_alpha                81.661(9)
_cell_angle_beta                 109.861(12)
_cell_angle_gamma                79.082(7)
_cell_volume                     1336.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1597
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      22.06
_cell_measurement_theta_min      3.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0683 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.8803.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lathe
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.345
_diffrn_reflns_Laue_measured_fraction_max 0.345
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7462
_diffrn_reflns_point_group_measured_fraction_full 0.338
_diffrn_reflns_point_group_measured_fraction_max 0.338
_diffrn_reflns_theta_full        23.277
_diffrn_reflns_theta_max         23.277
_diffrn_reflns_theta_min         2.435
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.345
_diffrn_measured_fraction_theta_max 0.345
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_full    0.331
_reflns_Friedel_fraction_max     0.331
_reflns_number_gt                1587
_reflns_number_total             2614
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 606 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0864
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2288
_refine_ls_wR_factor_ref         0.2761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O4-C11
 1.476 with sigma of 0.02
 C11-C12
 1.483 with sigma of 0.02
 O3-C3
 1.228 with sigma of 0.02
 O2-C10
 1.372 with sigma of 0.02
 C2-C3
 1.516 with sigma of 0.02
 C14-N2
 1.404 with sigma of 0.02
 C6-N2
 1.489 with sigma of 0.02
 C6-C5
 1.228 with sigma of 0.02
 C6-C7
 1.303 with sigma of 0.02
 C4-C5
 1.391 with sigma of 0.02
 C4-C66
 1.462 with sigma of 0.02
 C66-C8
 1.462 with sigma of 0.02
 C8-C7
 1.369 with sigma of 0.02
 C17-C16
 1.352 with sigma of 0.02
 O1-C10
 1.22 with sigma of 0.02
 F1-C5
 1.403 with sigma of 0.02
 O4-C7
 1.395 with sigma of 0.02
 C2-C10
 1.373 with sigma of 0.02
 C1-N1
 1.395 with sigma of 0.02
 C12-N1
 1.402 with sigma of 0.02
 C8-N1
 1.402 with sigma of 0.02
 C1-C2
 1.516 with sigma of 0.02
 C66-C3
 1.443 with sigma of 0.02
 C17-N2
 1.511 with sigma of 0.02
 C13-C12
 1.461 with sigma of 0.02
 C16-N3
 1.464 with sigma of 0.02
 C18-N3
 1.462 with sigma of 0.02
 C15-C14
 1.46 with sigma of 0.02
 C15-N3
 1.435 with sigma of 0.02
 C65-C67
 1.489 with sigma of 0.02
 O16-C65
 1.516 with sigma of 0.02
 O14-C64
 1.334 with sigma of 0.02
 O15-C57
 1.228 with sigma of 0.02
 C71-N12
 1.462 with sigma of 0.02
 C60-C61
 1.462 with sigma of 0.02
 C62-C61
 1.469 with sigma of 0.02
 C60-C59
 1.368 with sigma of 0.02
 C58-C59
 1.303 with sigma of 0.02
 C58-C63
 1.367 with sigma of 0.02
 C70-C71
 1.483 with sigma of 0.02
 C67-N10
 1.443 with sigma of 0.02
 F4-C59
 1.444 with sigma of 0.02
 C74-N12
 1.385 with sigma of 0.02
 O13-C64
 1.228 with sigma of 0.02
 C62-N10
 1.417 with sigma of 0.02
 C55-N10
 1.228 with sigma of 0.02
 C60-N11
 1.22 with sigma of 0.02
 C70-N11
 1.395 with sigma of 0.02
 C73-N11
 1.402 with sigma of 0.02
 C69-C67
 1.402 with sigma of 0.02
 C56-C57
 1.476 with sigma of 0.02
 C55-C56
 1.403 with sigma of 0.02
 C56-C64
 1.373 with sigma of 0.02
 O16-C61
 1.395 with sigma of 0.02
 C63-C62
 1.352 with sigma of 0.02
 C63-C57
 1.525 with sigma of 0.02
 C72-N12
 1.435 with sigma of 0.02
 C72-C73
 1.516 with sigma of 0.02
 O12-C47
 1.382 with sigma of 0.02
 C49-C48
 1.476 with sigma of 0.02
 F3-C41
 1.403 with sigma of 0.02
 C40-C45
 1.374 with sigma of 0.02
 C40-C41
 1.483 with sigma of 0.02
 C45-C44
 1.367 with sigma of 0.02
 C45-C39
 1.443 with sigma of 0.02
 C44-C43
 1.473 with sigma of 0.02
 C42-C43
 1.466 with sigma of 0.02
 C42-C41
 1.464 with sigma of 0.02
 O11-C39
 1.228 with sigma of 0.02
 C44-N7
 1.417 with sigma of 0.02
 C37-N7
 1.22 with sigma of 0.02
 O12-C43
 1.458 with sigma of 0.02
 C42-N8
 1.352 with sigma of 0.02
 C38-C39
 1.489 with sigma of 0.02
 C37-C38
 1.395 with sigma of 0.02
 C53-N8
 1.395 with sigma of 0.02
 C50-N8
 1.402 with sigma of 0.02
 C52-N9
 1.402 with sigma of 0.02
 C51-N9
 1.457 with sigma of 0.02
 C52-C53
 1.303 with sigma of 0.02
 C51-C50
 1.435 with sigma of 0.02
 C48-N7
 1.511 with sigma of 0.02
 O8-C29
 1.464 with sigma of 0.02
 C33-N6
 1.516 with sigma of 0.02
 C36-N6
 1.458 with sigma of 0.02
 C32-N5
 1.457 with sigma of 0.02
 C19-N4
 1.525 with sigma of 0.02
 C29-C30
 1.464 with sigma of 0.02
 C35-C34
 1.367 with sigma of 0.02
 C24-C25
 1.404 with sigma of 0.02
 C26-C25
 1.46 with sigma of 0.02
 C24-C23
 1.347 with sigma of 0.02
 C22-C23
 1.483 with sigma of 0.02
 C22-C27
 1.374 with sigma of 0.02
 C27-C26
 1.352 with sigma of 0.02
 O5-C28
 1.22 with sigma of 0.02
 F2-C23
 1.516 with sigma of 0.02
 O8-C25
 1.402 with sigma of 0.02
 C35-N6
 1.403 with sigma of 0.02
 C34-N5
 1.395 with sigma of 0.02
 C24-N5
 1.373 with sigma of 0.02
 O6-C28
 1.402 with sigma of 0.02
 C30-N4
 1.391 with sigma of 0.02
 C26-N4
 1.466 with sigma of 0.02
 C32-C33
 1.443 with sigma of 0.02
 C31-C30
 1.461 with sigma of 0.02
 C19-C20
 1.228 with sigma of 0.02
 C20-C28
 1.511 with sigma of 0.02
 O16-C61 \\sim O16A-C61
 with sigma of 0.02
 O16-C65 \\sim O16A-C65A
 with sigma of 0.02
 C65-C67 \\sim C65A-C67
 with sigma of 0.02
 O16-C67 \\sim O16A-C67
 with sigma of 0.04
 C61-C65 \\sim C61-C65A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uiso(O16) = Uiso(O16A)
Uiso(C65) = Uiso(C65A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O16A(0.32436) C65(0.32436) H65A(0.32436) H65B(0.32436)
 H67(0.32436) H67A(0.67564) O16(0.67564) C65A(0.67564) H65C(0.67564)
 H65D(0.67564)
6.a Riding coordinates:
 O17(H17C,H17D), O18(H18D,H18E)
6.b Ternary CH refined with riding coordinates:
 C12(H12), C30(H30), C48(H48), C67(H67), C67(H67A)
6.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C29(H29A,H29B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C47(H47A,H47B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B),
  C53(H53A,H53B), C65(H65A,H65B), C70(H70A,H70B), C71(H71A,H71B), C72(H72A,
 H72B), C73(H73A,H73B), C65A(H65C,H65D)
6.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C19(H19), C22(H22), C37(H37), C40(H40), C55(H55), C58(H58)
6.e Fitted hexagon refined as free rotating group:
 C7(C6,C5,C4,C66,C8), C27(C26,C25,C24,C23,C22), C42(C41,C40,C45,C44,C43),
 C63(C62,C61,C60,C59,C58)
6.f Tetrahedral OH refined with riding coordinates:
 O10(H10)
6.g Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C31(H31A,H31B,H31C), C36(H36A,H36B,
 H36C), C49(H49A,H49B,H49C), C69(H69A,H69B,H69C), C74(H74A,H74B,H74C), C54(H54A,
 H54B,H54C)
6.h Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6), O14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 -0.217(2) 0.637(3) 0.7129(18) 0.048(6) Uiso 1 1 d D . . . .
N1 N 0.130(2) 0.316(4) 1.0105(19) 0.029(7) Uiso 1 1 d D . . . .
O1 O 0.094(3) 0.234(4) 1.232(3) 0.051(9) Uiso 1 1 d D . . . .
C1 C 0.126(3) 0.276(5) 1.090(3) 0.045(9) Uiso 1 1 d D . . . .
H1 H 0.185663 0.216467 1.138233 0.054 Uiso 1 1 calc R U . . .
N2 N -0.018(3) 0.535(4) 0.706(2) 0.027(6) Uiso 1 1 d D . . . .
O2 O -0.085(3) 0.356(3) 1.169(3) 0.036(6) Uiso 1 1 d D . . . .
H2 H -0.121514 0.466742 1.130268 0.054 Uiso 1 1 calc R U . . .
C2 C 0.019(3) 0.338(4) 1.088(2) 0.025(8) Uiso 1 1 d D . . . .
O3 O -0.164(3) 0.463(3) 1.016(2) 0.032(5) Uiso 1 1 d D . . . .
N3 N 0.082(3) 0.329(4) 0.611(3) 0.035(6) Uiso 1 1 d D . . . .
C3 C -0.079(3) 0.420(4) 1.010(2) 0.019(7) Uiso 1 1 d D . . . .
O4 O 0.152(2) 0.410(3) 0.855(2) 0.032(5) Uiso 1 1 d D . . . .
C7 C 0.0574(18) 0.434(3) 0.8617(17) 0.032(9) Uiso 1 1 d DG . . . .
C6 C -0.028(2) 0.508(3) 0.7865(16) 0.025(8) Uiso 1 1 d DG . . . .
C5 C -0.1300(19) 0.551(3) 0.7858(15) 0.014(7) Uiso 1 1 d DG . . . .
C4 C -0.1457(18) 0.518(3) 0.8603(17) 0.021(8) Uiso 1 1 d DG . . . .
H4 H -0.213653 0.546638 0.859849 0.025 Uiso 1 1 calc R U . . .
C66 C -0.060(2) 0.444(3) 0.9356(16) 0.027(8) Uiso 1 1 d DG . . . .
C8 C 0.0417(19) 0.402(3) 0.9363(16) 0.020(7) Uiso 1 1 d DG . . . .
C10 C 0.013(3) 0.295(5) 1.167(3) 0.033(11) Uiso 1 1 d D . . . .
C11 C 0.232(3) 0.242(5) 0.925(2) 0.033(7) Uiso 1 1 d D . . . .
H11A H 0.300122 0.239251 0.922820 0.039 Uiso 1 1 calc R U . . .
H11B H 0.219834 0.090156 0.922068 0.039 Uiso 1 1 calc R U . . .
C12 C 0.233(3) 0.288(6) 1.007(2) 0.043(8) Uiso 1 1 d D . . . .
H12 H 0.256101 0.428928 1.013954 0.052 Uiso 1 1 calc R U . . .
C13 C 0.311(4) 0.092(5) 1.070(3) 0.042(8) Uiso 1 1 d D . . . .
H13A H 0.284844 -0.043510 1.067539 0.063 Uiso 1 1 calc R U . . .
H13B H 0.323138 0.124625 1.124381 0.063 Uiso 1 1 calc R U . . .
H13C H 0.375466 0.066398 1.061124 0.063 Uiso 1 1 calc R U . . .
C14 C 0.070(4) 0.597(4) 0.694(3) 0.037(7) Uiso 1 1 d D . . . .
H14A H 0.109690 0.646389 0.742156 0.044 Uiso 1 1 calc R U . . .
H14B H 0.043571 0.727900 0.646443 0.044 Uiso 1 1 calc R U . . .
C15 C 0.142(3) 0.411(4) 0.678(3) 0.032(7) Uiso 1 1 d D . . . .
H15A H 0.195400 0.470753 0.664935 0.038 Uiso 1 1 calc R U . . .
H15B H 0.176505 0.286714 0.727607 0.038 Uiso 1 1 calc R U . . .
C16 C -0.005(4) 0.247(5) 0.623(3) 0.038(8) Uiso 1 1 d D . . . .
H16A H -0.044549 0.201414 0.572854 0.046 Uiso 1 1 calc R U . . .
H16B H 0.021882 0.113952 0.668885 0.046 Uiso 1 1 calc R U . . .
C17 C -0.073(3) 0.429(4) 0.639(3) 0.032(7) Uiso 1 1 d D . . . .
H17A H -0.125609 0.367539 0.652979 0.038 Uiso 1 1 calc R U . . .
H17B H -0.109913 0.548553 0.587949 0.038 Uiso 1 1 calc R U . . .
C18 C 0.144(4) 0.150(5) 0.588(4) 0.034(7) Uiso 1 1 d D . . . .
H18A H 0.198199 0.205131 0.575257 0.052 Uiso 1 1 calc R U . . .
H18B H 0.099024 0.110937 0.539266 0.052 Uiso 1 1 calc R U . . .
H18C H 0.175161 0.016015 0.632691 0.052 Uiso 1 1 calc R U . . .
F2 F 0.695(2) 0.331(3) 0.7676(18) 0.047(5) Uiso 1 1 d D . . . .
N4 N 0.342(2) 0.751(4) 0.473(2) 0.035(7) Uiso 1 1 d D . . . .
O5 O 0.361(3) 0.857(4) 0.238(3) 0.064(9) Uiso 1 1 d D . . . .
N5 N 0.493(3) 0.426(4) 0.768(2) 0.030(6) Uiso 1 1 d D . . . .
O6 O 0.551(3) 0.720(3) 0.310(3) 0.037(6) Uiso 1 1 d D . . . .
H6 H 0.582930 0.618251 0.352740 0.056 Uiso 1 1 calc R U . . .
N6 N 0.400(3) 0.615(3) 0.874(2) 0.031(6) Uiso 1 1 d D . . . .
O7 O 0.633(3) 0.615(4) 0.458(3) 0.038(5) Uiso 1 1 d . . . . .
O8 O 0.317(3) 0.591(4) 0.619(3) 0.043(7) Uiso 1 1 d D . . . .
C19 C 0.351(3) 0.797(4) 0.394(3) 0.026(7) Uiso 1 1 d D . . . .
H19 H 0.289377 0.867962 0.347858 0.031 Uiso 1 1 calc R U . . .
C20 C 0.436(4) 0.747(5) 0.382(3) 0.042(11) Uiso 1 1 d D . . . .
C21 C 0.537(5) 0.655(5) 0.460(4) 0.018(7) Uiso 1 1 d . . . . .
C27 C 0.531(2) 0.591(3) 0.5430(16) 0.034(8) Uiso 1 1 d DG . . . .
C26 C 0.430(2) 0.627(4) 0.5440(16) 0.021(7) Uiso 1 1 d DG . . . .
C25 C 0.417(2) 0.569(4) 0.6186(18) 0.029(8) Uiso 1 1 d DG . . . .
C24 C 0.504(2) 0.475(4) 0.6922(16) 0.028(8) Uiso 1 1 d DG . . . .
C23 C 0.604(2) 0.439(4) 0.6913(16) 0.019(7) Uiso 1 1 d DG . . . .
C22 C 0.618(2) 0.496(3) 0.6167(18) 0.034(8) Uiso 1 1 d DG . . . .
H22 H 0.685362 0.472249 0.616003 0.041 Uiso 1 1 calc R U . . .
C28 C 0.443(3) 0.778(5) 0.298(2) 0.017(8) Uiso 1 1 d D . . . .
C29 C 0.229(4) 0.659(5) 0.539(3) 0.032(9) Uiso 1 1 d D . . . .
H29A H 0.224460 0.528405 0.512926 0.039 Uiso 1 1 calc R U . . .
H29B H 0.163568 0.713869 0.545904 0.039 Uiso 1 1 calc R U . . .
C30 C 0.250(4) 0.841(5) 0.489(3) 0.045(9) Uiso 1 1 d D . . . .
H30 H 0.266333 0.955673 0.521886 0.054 Uiso 1 1 calc R U . . .
C31 C 0.159(4) 0.959(7) 0.412(3) 0.052(10) Uiso 1 1 d D . . . .
H31A H 0.162666 0.885671 0.367462 0.078 Uiso 1 1 calc R U . . .
H31B H 0.159807 1.117822 0.397129 0.078 Uiso 1 1 calc R U . . .
H31C H 0.095472 0.951930 0.420263 0.078 Uiso 1 1 calc R U . . .
C32 C 0.405(3) 0.358(4) 0.781(3) 0.024(7) Uiso 1 1 d D . . . .
H32A H 0.363603 0.312633 0.731941 0.029 Uiso 1 1 calc R U . . .
H32B H 0.431221 0.225382 0.827570 0.029 Uiso 1 1 calc R U . . .
C33 C 0.339(3) 0.542(4) 0.798(3) 0.029(7) Uiso 1 1 d D . . . .
H33A H 0.280676 0.490636 0.805618 0.035 Uiso 1 1 calc R U . . .
H33B H 0.310363 0.672320 0.750251 0.035 Uiso 1 1 calc R U . . .
C34 C 0.546(3) 0.534(5) 0.828(3) 0.040(8) Uiso 1 1 d D . . . .
H34A H 0.589545 0.611682 0.807195 0.047 Uiso 1 1 calc R U . . .
H34B H 0.592441 0.415714 0.877217 0.047 Uiso 1 1 calc R U . . .
C35 C 0.479(4) 0.702(4) 0.853(3) 0.025(6) Uiso 1 1 d D . . . .
H35A H 0.523403 0.747856 0.901085 0.030 Uiso 1 1 calc R U . . .
H35B H 0.444827 0.838415 0.808272 0.030 Uiso 1 1 calc R U . . .
C36 C 0.338(6) 0.798(6) 0.896(5) 0.059(10) Uiso 1 1 d D . . . .
H36A H 0.302970 0.925981 0.849077 0.088 Uiso 1 1 calc R U . . .
H36B H 0.382889 0.846756 0.941775 0.088 Uiso 1 1 calc R U . . .
H36C H 0.286221 0.740817 0.912270 0.088 Uiso 1 1 calc R U . . .
F3 F 0.287(2) 0.381(3) 0.209(2) 0.054(6) Uiso 1 1 d D . . . .
N7 N 0.629(2) 0.101(3) 0.512(2) 0.030(7) Uiso 1 1 d D . . . .
N8 N 0.486(3) 0.288(3) 0.209(2) 0.036(6) Uiso 1 1 d D . . . .
C9 C 0.503(7) 0.012(7) 0.661(6) 0.035(10) Uiso 1 1 d . . . . .
N9 N 0.581(3) 0.451(4) 0.105(3) 0.055(8) Uiso 1 1 d D . . . .
O9 O 0.591(4) -0.084(4) 0.730(4) 0.045(8) Uiso 1 1 d . . . . .
O10 O 0.411(3) 0.038(3) 0.664(3) 0.043(6) Uiso 1 1 d . . . . .
H10 H 0.366899 0.092822 0.616623 0.064 Uiso 1 1 calc R U . . .
O11 O 0.331(3) 0.229(3) 0.511(2) 0.034(5) Uiso 1 1 d D . . . .
O12 O 0.658(3) 0.163(4) 0.360(2) 0.041(6) Uiso 1 1 d D . . . .
C37 C 0.612(3) 0.055(4) 0.578(3) 0.032(7) Uiso 1 1 d D . . . .
H37 H 0.670136 -0.002665 0.627542 0.038 Uiso 1 1 calc R U . . .
C38 C 0.515(3) 0.081(5) 0.584(3) 0.028(8) Uiso 1 1 d D . . . .
C39 C 0.419(3) 0.181(5) 0.508(2) 0.028(8) Uiso 1 1 d D . . . .
C42 C 0.470(2) 0.270(3) 0.2844(16) 0.025(8) Uiso 1 1 d DG . . . .
C41 C 0.368(2) 0.316(3) 0.2840(17) 0.020(7) Uiso 1 1 d DG . . . .
C40 C 0.3529(19) 0.290(3) 0.3588(18) 0.025(8) Uiso 1 1 d DG . . . .
H40 H 0.285011 0.320590 0.358551 0.030 Uiso 1 1 calc R U . . .
C45 C 0.439(2) 0.217(3) 0.4339(17) 0.024(8) Uiso 1 1 d DG . . . .
C44 C 0.540(2) 0.171(3) 0.4343(16) 0.019(7) Uiso 1 1 d DG . . . .
C43 C 0.5556(19) 0.198(3) 0.3595(18) 0.028(9) Uiso 1 1 d DG . . . .
C47 C 0.731(3) 0.020(5) 0.430(3) 0.032(8) Uiso 1 1 d D . . . .
H47A H 0.799466 0.001777 0.426784 0.038 Uiso 1 1 calc R U . . .
H47B H 0.715999 -0.130020 0.434933 0.038 Uiso 1 1 calc R U . . .
C48 C 0.734(3) 0.105(6) 0.507(3) 0.037(8) Uiso 1 1 d D . . . .
H48 H 0.741271 0.263192 0.500763 0.045 Uiso 1 1 calc R U . . .
C49 C 0.816(4) -0.039(6) 0.584(3) 0.050(9) Uiso 1 1 d D . . . .
H49A H 0.796575 -0.176581 0.600105 0.075 Uiso 1 1 calc R U . . .
H49B H 0.825977 0.044648 0.627392 0.075 Uiso 1 1 calc R U . . .
H49C H 0.881021 -0.080513 0.575354 0.075 Uiso 1 1 calc R U . . .
C50 C 0.563(4) 0.138(5) 0.192(4) 0.057(10) Uiso 1 1 d D . . . .
H50A H 0.529376 0.079164 0.144181 0.068 Uiso 1 1 calc R U . . .
H50B H 0.600872 0.008073 0.239377 0.068 Uiso 1 1 calc R U . . .
C51 C 0.639(4) 0.261(5) 0.175(3) 0.052(9) Uiso 1 1 d D . . . .
H51A H 0.674332 0.317901 0.223571 0.062 Uiso 1 1 calc R U . . .
H51B H 0.691551 0.157046 0.164020 0.062 Uiso 1 1 calc R U . . .
C52 C 0.505(4) 0.608(5) 0.122(4) 0.048(9) Uiso 1 1 d D . . . .
H52A H 0.540091 0.679895 0.165263 0.057 Uiso 1 1 calc R U . . .
H52B H 0.462438 0.728530 0.072114 0.057 Uiso 1 1 calc R U . . .
C53 C 0.439(3) 0.491(4) 0.147(3) 0.038(8) Uiso 1 1 d D . . . .
H53A H 0.392723 0.453972 0.097986 0.045 Uiso 1 1 calc R U . . .
H53B H 0.396032 0.597201 0.165524 0.045 Uiso 1 1 calc R U . . .
F4 F 1.194(2) 0.683(3) 0.2767(19) 0.048(5) Uiso 1 1 d D . . . .
N10 N 0.857(2) 0.977(4) -0.033(2) 0.032(7) Uiso 1 1 d D . . . .
N11 N 0.987(3) 0.774(3) 0.268(2) 0.034(6) Uiso 1 1 d D . . . .
N12 N 0.883(3) 0.595(3) 0.368(2) 0.025(6) Uiso 1 1 d D . . . .
O13 O 0.909(3) 1.053(4) -0.245(3) 0.041(7) Uiso 1 1 d D . . . .
O14 O 1.087(3) 0.934(3) -0.178(3) 0.042(6) Uiso 1 1 d D . . . .
H14 H 1.124497 0.824180 -0.139085 0.062 Uiso 1 1 calc R U . . .
O15 O 1.157(3) 0.808(3) -0.028(2) 0.031(5) Uiso 1 1 d D . . . .
C55 C 0.876(3) 0.996(4) -0.100(3) 0.028(7) Uiso 1 1 d D . . . .
H55 H 0.818132 1.048692 -0.150267 0.033 Uiso 1 1 calc R U . . .
C56 C 0.972(3) 0.946(4) -0.105(2) 0.028(8) Uiso 1 1 d D . . . .
C57 C 1.066(3) 0.866(4) -0.027(2) 0.025(8) Uiso 1 1 d D . . . .
C63 C 1.045(2) 0.846(3) 0.0508(17) 0.025(8) Uiso 1 1 d DG . . . .
C62 C 0.942(2) 0.897(4) 0.0465(17) 0.023(7) Uiso 1 1 d DG . . . .
C61 C 0.922(2) 0.872(3) 0.119(2) 0.043(10) Uiso 1 1 d DG . . . .
C60 C 1.005(2) 0.796(3) 0.1961(18) 0.037(9) Uiso 1 1 d DG . . . .
C59 C 1.108(2) 0.745(3) 0.2005(17) 0.019(8) Uiso 1 1 d DG . . . .
C58 C 1.128(2) 0.770(3) 0.1278(19) 0.036(9) Uiso 1 1 d DG . . . .
H58 H 1.197007 0.735709 0.130713 0.043 Uiso 1 1 calc R U . . .
C64 C 0.988(3) 0.977(5) -0.179(3) 0.032(11) Uiso 1 1 d D . . . .
O16A O 0.816(4) 0.845(11) 0.105(4) 0.031(8) Uiso 0.3244 1 d D . P A 1
C65 C 0.752(7) 0.921(19) 0.046(5) 0.045(14) Uiso 0.3244 1 d D . P A 1
H65A H 0.699807 1.022380 0.058697 0.053 Uiso 0.3244 1 calc R U P A 1
H65B H 0.722000 0.795167 0.029952 0.053 Uiso 0.3244 1 calc R U P A 1
C67 C 0.752(3) 1.056(5) -0.034(3) 0.040(8) Uiso 1 1 d D . . . .
H67 H 0.726470 1.223558 -0.044080 0.047 Uiso 0.3244 1 calc R U P A 1
H67A H 0.729338 1.218956 -0.062843 0.047 Uiso 0.6756 1 calc R U P A 2
C69 C 0.684(4) 0.950(5) -0.089(3) 0.042(8) Uiso 1 1 d D . . . .
H69A H 0.662413 1.033504 -0.145019 0.062 Uiso 1 1 calc R U . . .
H69B H 0.622590 0.952604 -0.074869 0.062 Uiso 1 1 calc R U . . .
H69C H 0.719729 0.793599 -0.082514 0.062 Uiso 1 1 calc R U . . .
C70 C 1.039(3) 0.574(4) 0.335(3) 0.036(7) Uiso 1 1 d D . . . .
H70A H 1.078420 0.621967 0.384206 0.043 Uiso 1 1 calc R U . . .
H70B H 1.089704 0.472936 0.320510 0.043 Uiso 1 1 calc R U . . .
C71 C 0.969(4) 0.439(5) 0.356(4) 0.043(8) Uiso 1 1 d D . . . .
H71A H 0.939385 0.363831 0.311785 0.052 Uiso 1 1 calc R U . . .
H71B H 1.008842 0.320874 0.406907 0.052 Uiso 1 1 calc R U . . .
C72 C 0.827(3) 0.780(4) 0.296(3) 0.040(8) Uiso 1 1 d D . . . .
H72A H 0.770987 0.881737 0.304622 0.048 Uiso 1 1 calc R U . . .
H72B H 0.795021 0.718180 0.247989 0.048 Uiso 1 1 calc R U . . .
C73 C 0.901(4) 0.915(4) 0.279(3) 0.032(7) Uiso 1 1 d D . . . .
H73A H 0.861780 1.036203 0.228465 0.038 Uiso 1 1 calc R U . . .
H73B H 0.927041 0.988389 0.324320 0.038 Uiso 1 1 calc R U . . .
C74 C 0.815(4) 0.459(5) 0.383(4) 0.039(8) Uiso 1 1 d D . . . .
H74A H 0.790673 0.386573 0.337609 0.059 Uiso 1 1 calc R U . . .
H74B H 0.756222 0.556477 0.388447 0.059 Uiso 1 1 calc R U . . .
H74C H 0.853326 0.342564 0.433740 0.059 Uiso 1 1 calc R U . . .
O16 O 0.815(3) 0.933(5) 0.112(3) 0.031(8) Uiso 0.6756 1 d D . P A 2
C65A C 0.758(6) 1.058(9) 0.054(4) 0.045(14) Uiso 0.6756 1 d D . P A 2
H65C H 0.768193 1.208580 0.062746 0.053 Uiso 0.6756 1 calc R U P A 2
H65D H 0.688882 1.057268 0.053685 0.053 Uiso 0.6756 1 calc R U P A 2
C54 C 0.662(7) 0.570(8) 0.085(6) 0.094(15) Uiso 1 1 d . . . . .
H54A H 0.696106 0.633125 0.131538 0.141 Uiso 1 1 calc R U . . .
H54B H 0.626429 0.692469 0.036240 0.141 Uiso 1 1 calc R U . . .
H54C H 0.713836 0.459487 0.076533 0.141 Uiso 1 1 calc R U . . .
O17 O -0.012(3) 0.775(4) 0.493(3) 0.042(5) Uiso 1 1 d . . . . .
H17C H 0.038536 0.640914 0.536054 0.063 Uiso 1 1 d R U . . .
H17D H -0.054742 0.690632 0.455855 0.063 Uiso 1 1 d R U . . .
O18 O 0.492(4) 0.203(4) 0.989(3) 0.065(7) Uiso 1 1 d . . . . .
H18D H 0.468178 0.344026 0.956767 0.098 Uiso 1 1 d R U . . .
H18E H 0.540653 0.232336 1.030385 0.098 Uiso 1 1 d 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 C5 1.38(3) . ?
N1 C1 1.40(3) . ?
N1 C8 1.40(3) . ?
N1 C12 1.44(3) . ?
O1 C10 1.24(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.47(3) . ?
N2 C6 1.45(2) . ?
N2 C14 1.43(3) . ?
N2 C17 1.49(3) . ?
O2 H2 0.8200 . ?
O2 C10 1.36(3) . ?
C2 C3 1.51(3) . ?
C2 C10 1.40(3) . ?
O3 C3 1.22(3) . ?
N3 C15 1.41(3) . ?
N3 C16 1.47(3) . ?
N3 C18 1.45(2) . ?
C3 C66 1.41(2) . ?
O4 C7 1.35(2) . ?
O4 C11 1.44(3) . ?
C7 C6 1.3900 . ?
C7 C8 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C66 1.3900 . ?
C66 C8 1.3900 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.48(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.46(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.48(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.44(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.45(3) . ?
N4 C19 1.42(3) . ?
N4 C26 1.41(3) . ?
N4 C30 1.43(3) . ?
O5 C28 1.22(3) . ?
N5 C24 1.38(2) . ?
N5 C32 1.45(2) . ?
N5 C34 1.39(3) . ?
O6 H6 0.8200 . ?
O6 C28 1.41(3) . ?
N6 C33 1.51(3) . ?
N6 C35 1.44(2) . ?
N6 C36 1.45(2) . ?
O7 C21 1.33(5) . ?
O8 C25 1.38(2) . ?
O8 C29 1.46(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.27(3) . ?
C20 C21 1.53(9) . ?
C20 C28 1.50(3) . ?
C21 C27 1.49(5) . ?
C27 C26 1.3900 . ?
C27 C22 1.3900 . ?
C26 C25 1.3900 . ?
C25 C24 1.3900 . ?
C24 C23 1.3900 . ?
C23 C22 1.3900 . ?
C22 H22 0.9300 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.45(3) . ?
C30 H30 0.9800 . ?
C30 C31 1.47(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.44(2) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.47(2) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
F3 C41 1.36(3) . ?
N7 C37 1.27(3) . ?
N7 C44 1.43(3) . ?
N7 C48 1.50(3) . ?
N8 C42 1.41(2) . ?
N8 C50 1.41(3) . ?
N8 C53 1.40(3) . ?
C9 O9 1.34(12) . ?
C9 O10 1.28(6) . ?
C9 C38 1.44(6) . ?
N9 C51 1.44(3) . ?
N9 C52 1.43(3) . ?
N9 C54 1.56(5) . ?
O10 H10 0.8200 . ?
O11 C39 1.23(3) . ?
O12 C43 1.41(2) . ?
O12 C47 1.35(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.37(3) . ?
C38 C39 1.48(3) . ?
C39 C45 1.42(2) . ?
C42 C41 1.3900 . ?
C42 C43 1.3900 . ?
C41 C40 1.3900 . ?
C40 H40 0.9300 . ?
C40 C45 1.3900 . ?
C45 C44 1.3900 . ?
C44 C43 1.3900 . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C48 1.50(5) . ?
C48 H48 0.9800 . ?
C48 C49 1.46(3) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C50 C51 1.49(3) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C52 C53 1.40(2) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
F4 C59 1.41(3) . ?
N10 C55 1.30(2) . ?
N10 C62 1.43(3) . ?
N10 C67 1.44(3) . ?
N11 C60 1.36(2) . ?
N11 C70 1.43(3) . ?
N11 C73 1.43(3) . ?
N12 C71 1.47(3) . ?
N12 C72 1.44(3) . ?
N12 C74 1.44(2) . ?
O13 C64 1.24(3) . ?
O14 H14 0.8200 . ?
O14 C64 1.35(3) . ?
O15 C57 1.26(3) . ?
C55 H55 0.9300 . ?
C55 C56 1.35(3) . ?
C56 C57 1.47(3) . ?
C56 C64 1.39(3) . ?
C57 C63 1.48(2) . ?
C63 C62 1.3900 . ?
C63 C58 1.3900 . ?
C62 C61 1.3900 . ?
C61 C60 1.3900 . ?
C61 O16A 1.46(4) . ?
C61 O16 1.43(3) . ?
C60 C59 1.3900 . ?
C59 C58 1.3900 . ?
C58 H58 0.9300 . ?
O16A C65 1.09(11) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C65 C67 1.52(3) . ?
C67 H67 0.9800 . ?
C67 H67A 0.9800 . ?
C67 C69 1.42(3) . ?
C67 C65A 1.53(4) . ?
C69 H69A 0.9600 . ?
C69 H69B 0.9600 . ?
C69 H69C 0.9600 . ?
C70 H70A 0.9700 . ?
C70 H70B 0.9700 . ?
C70 C71 1.50(3) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 H72A 0.9700 . ?
C72 H72B 0.9700 . ?
C72 C73 1.51(2) . ?
C73 H73A 0.9700 . ?
C73 H73B 0.9700 . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 0.9600 . ?
O16 C65A 1.11(8) . ?
C65A H65C 0.9700 . ?
C65A H65D 0.9700 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
O17 H17C 0.9873 . ?
O17 H17D 0.9960 . ?
O18 H18D 0.8838 . ?
O18 H18E 0.8827 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 124(2) . . ?
C1 N1 C12 117(3) . . ?
C8 N1 C12 119(2) . . ?
N1 C1 H1 123.3 . . ?
N1 C1 C2 113(3) . . ?
C2 C1 H1 123.3 . . ?
C6 N2 C17 124.0(19) . . ?
C14 N2 C6 123(3) . . ?
C14 N2 C17 110(2) . . ?
C10 O2 H2 109.5 . . ?
C1 C2 C3 124(3) . . ?
C10 C2 C1 114(3) . . ?
C10 C2 C3 121(3) . . ?
C15 N3 C16 115(3) . . ?
C15 N3 C18 114(3) . . ?
C18 N3 C16 108(2) . . ?
O3 C3 C2 118(3) . . ?
O3 C3 C66 127(3) . . ?
C66 C3 C2 115(3) . . ?
C7 O4 C11 110(2) . . ?
O4 C7 C6 115(2) . . ?
O4 C7 C8 125(2) . . ?
C6 C7 C8 120.0 . . ?
C7 C6 N2 123.0(19) . . ?
C7 C6 C5 120.0 . . ?
C5 C6 N2 117.0(19) . . ?
F1 C5 C6 122.0(14) . . ?
F1 C5 C4 117.9(14) . . ?
C4 C5 C6 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C66 120.0 . . ?
C66 C4 H4 120.0 . . ?
C4 C66 C3 118(2) . . ?
C4 C66 C8 120.0 . . ?
C8 C66 C3 122(2) . . ?
C7 C8 N1 118.1(16) . . ?
C66 C8 N1 121.8(16) . . ?
C66 C8 C7 120.0 . . ?
O1 C10 O2 123(3) . . ?
O1 C10 C2 121(3) . . ?
O2 C10 C2 116(3) . . ?
O4 C11 H11A 108.9 . . ?
O4 C11 H11B 108.9 . . ?
O4 C11 C12 113(3) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
N1 C12 C11 111(3) . . ?
N1 C12 H12 109.1 . . ?
N1 C12 C13 112(2) . . ?
C11 C12 H12 109.1 . . ?
C13 C12 C11 106(3) . . ?
C13 C12 H12 109.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 108.5 . . ?
N2 C14 H14B 108.5 . . ?
N2 C14 C15 115(2) . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
N3 C15 C14 108(3) . . ?
N3 C15 H15A 110.0 . . ?
N3 C15 H15B 110.0 . . ?
C14 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
N3 C16 H16A 109.8 . . ?
N3 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 N3 109(2) . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
N2 C17 H17A 108.7 . . ?
N2 C17 H17B 108.7 . . ?
C16 C17 N2 114(3) . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 N4 C30 125(3) . . ?
C26 N4 C19 120(2) . . ?
C26 N4 C30 115(3) . . ?
C24 N5 C32 126(3) . . ?
C24 N5 C34 115.7(19) . . ?
C34 N5 C32 114(2) . . ?
C28 O6 H6 109.5 . . ?
C35 N6 C33 105(3) . . ?
C35 N6 C36 108(2) . . ?
C36 N6 C33 114(4) . . ?
C25 O8 C29 117(3) . . ?
N4 C19 H19 117.6 . . ?
C20 C19 N4 125(4) . . ?
C20 C19 H19 117.6 . . ?
C19 C20 C21 116(3) . . ?
C19 C20 C28 124(4) . . ?
C28 C20 C21 119(3) . . ?
O7 C21 C20 124(4) . . ?
O7 C21 C27 116(6) . . ?
C27 C21 C20 120(3) . . ?
C26 C27 C21 116(3) . . ?
C26 C27 C22 120.0 . . ?
C22 C27 C21 124(3) . . ?
C27 C26 N4 120.8(16) . . ?
C27 C26 C25 120.0 . . ?
C25 C26 N4 118.5(16) . . ?
O8 C25 C26 120(2) . . ?
O8 C25 C24 120(2) . . ?
C26 C25 C24 120.0 . . ?
N5 C24 C25 121(2) . . ?
N5 C24 C23 119(2) . . ?
C25 C24 C23 120.0 . . ?
C24 C23 F2 119.8(14) . . ?
C22 C23 F2 120.1(14) . . ?
C22 C23 C24 120.0 . . ?
C27 C22 H22 120.0 . . ?
C23 C22 C27 120.0 . . ?
C23 C22 H22 120.0 . . ?
O5 C28 O6 135(3) . . ?
O5 C28 C20 117(3) . . ?
O6 C28 C20 108(3) . . ?
O8 C29 H29A 110.5 . . ?
O8 C29 H29B 110.5 . . ?
H29A C29 H29B 108.7 . . ?
C30 C29 O8 106(4) . . ?
C30 C29 H29A 110.5 . . ?
C30 C29 H29B 110.5 . . ?
N4 C30 C29 110(3) . . ?
N4 C30 H30 107.2 . . ?
N4 C30 C31 112(3) . . ?
C29 C30 H30 107.2 . . ?
C29 C30 C31 113(4) . . ?
C31 C30 H30 107.2 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 H32A 109.3 . . ?
N5 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C33 C32 N5 111.7(19) . . ?
C33 C32 H32A 109.3 . . ?
C33 C32 H32B 109.3 . . ?
N6 C33 H33A 109.5 . . ?
N6 C33 H33B 109.5 . . ?
C32 C33 N6 111(3) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 108.0 . . ?
N5 C34 H34A 108.3 . . ?
N5 C34 H34B 108.3 . . ?
N5 C34 C35 116(3) . . ?
H34A C34 H34B 107.4 . . ?
C35 C34 H34A 108.3 . . ?
C35 C34 H34B 108.3 . . ?
N6 C35 C34 113.4(19) . . ?
N6 C35 H35A 108.9 . . ?
N6 C35 H35B 108.9 . . ?
C34 C35 H35A 108.9 . . ?
C34 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C37 N7 C44 117(3) . . ?
C37 N7 C48 126(3) . . ?
C44 N7 C48 117(3) . . ?
C42 N8 C50 127(3) . . ?
C53 N8 C42 121(2) . . ?
C53 N8 C50 111(3) . . ?
O9 C9 C38 118(5) . . ?
O10 C9 O9 122(5) . . ?
O10 C9 C38 120(8) . . ?
C51 N9 C54 107(4) . . ?
C52 N9 C51 110(3) . . ?
C52 N9 C54 111(2) . . ?
C9 O10 H10 109.5 . . ?
C47 O12 C43 112(2) . . ?
N7 C37 H37 116.7 . . ?
N7 C37 C38 127(4) . . ?
C38 C37 H37 116.7 . . ?
C9 C38 C39 118(4) . . ?
C37 C38 C9 123(5) . . ?
C37 C38 C39 119(3) . . ?
O11 C39 C38 122(3) . . ?
O11 C39 C45 125(3) . . ?
C45 C39 C38 113(3) . . ?
C41 C42 N8 121(2) . . ?
C41 C42 C43 120.0 . . ?
C43 C42 N8 119(2) . . ?
F3 C41 C42 117.6(16) . . ?
F3 C41 C40 122.4(16) . . ?
C40 C41 C42 120.0 . . ?
C41 C40 H40 120.0 . . ?
C41 C40 C45 120.0 . . ?
C45 C40 H40 120.0 . . ?
C40 C45 C39 118(2) . . ?
C40 C45 C44 120.0 . . ?
C44 C45 C39 122(2) . . ?
C45 C44 N7 120.0(15) . . ?
C43 C44 N7 119.9(15) . . ?
C43 C44 C45 120.0 . . ?
C42 C43 O12 120(2) . . ?
C44 C43 O12 120(2) . . ?
C44 C43 C42 120.0 . . ?
O12 C47 H47A 108.9 . . ?
O12 C47 H47B 108.9 . . ?
O12 C47 C48 113(3) . . ?
H47A C47 H47B 107.7 . . ?
C48 C47 H47A 108.9 . . ?
C48 C47 H47B 108.9 . . ?
N7 C48 C47 104(3) . . ?
N7 C48 H48 109.6 . . ?
C47 C48 H48 109.6 . . ?
C49 C48 N7 109(3) . . ?
C49 C48 C47 114(3) . . ?
C49 C48 H48 109.6 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
N8 C50 H50A 109.5 . . ?
N8 C50 H50B 109.5 . . ?
N8 C50 C51 111(2) . . ?
H50A C50 H50B 108.1 . . ?
C51 C50 H50A 109.5 . . ?
C51 C50 H50B 109.5 . . ?
N9 C51 C50 108(3) . . ?
N9 C51 H51A 110.1 . . ?
N9 C51 H51B 110.1 . . ?
C50 C51 H51A 110.1 . . ?
C50 C51 H51B 110.1 . . ?
H51A C51 H51B 108.4 . . ?
N9 C52 H52A 109.6 . . ?
N9 C52 H52B 109.6 . . ?
H52A C52 H52B 108.1 . . ?
C53 C52 N9 110(2) . . ?
C53 C52 H52A 109.6 . . ?
C53 C52 H52B 109.6 . . ?
N8 C53 H53A 107.7 . . ?
N8 C53 H53B 107.7 . . ?
C52 C53 N8 119(3) . . ?
C52 C53 H53A 107.7 . . ?
C52 C53 H53B 107.7 . . ?
H53A C53 H53B 107.1 . . ?
C55 N10 C62 120(3) . . ?
C55 N10 C67 122(3) . . ?
C62 N10 C67 118(2) . . ?
C60 N11 C70 122(2) . . ?
C60 N11 C73 124(3) . . ?
C73 N11 C70 112(2) . . ?
C72 N12 C71 111(3) . . ?
C72 N12 C74 111(3) . . ?
C74 N12 C71 107(2) . . ?
C64 O14 H14 109.5 . . ?
N10 C55 H55 116.9 . . ?
N10 C55 C56 126(4) . . ?
C56 C55 H55 116.9 . . ?
C55 C56 C57 119(3) . . ?
C55 C56 C64 124(3) . . ?
C64 C56 C57 117(3) . . ?
O15 C57 C56 122(3) . . ?
O15 C57 C63 123(3) . . ?
C56 C57 C63 115(2) . . ?
C62 C63 C57 120(2) . . ?
C62 C63 C58 120.0 . . ?
C58 C63 C57 120(2) . . ?
C63 C62 N10 120.1(17) . . ?
C63 C62 C61 120.0 . . ?
C61 C62 N10 119.9(17) . . ?
C62 C61 O16A 112(3) . . ?
C62 C61 O16 118(2) . . ?
C60 C61 C62 120.0 . . ?
C60 C61 O16A 123(3) . . ?
C60 C61 O16 122(2) . . ?
N11 C60 C61 121(2) . . ?
N11 C60 C59 119(2) . . ?
C59 C60 C61 120.0 . . ?
C60 C59 F4 122.1(17) . . ?
C60 C59 C58 120.0 . . ?
C58 C59 F4 117.7(16) . . ?
C63 C58 H58 120.0 . . ?
C59 C58 C63 120.0 . . ?
C59 C58 H58 120.0 . . ?
O13 C64 O14 123(3) . . ?
O13 C64 C56 117(3) . . ?
O14 C64 C56 119(3) . . ?
C65 O16A C61 121(5) . . ?
O16A C65 H65A 104.8 . . ?
O16A C65 H65B 104.8 . . ?
O16A C65 C67 130(7) . . ?
H65A C65 H65B 105.8 . . ?
C67 C65 H65A 104.8 . . ?
C67 C65 H65B 104.8 . . ?
N10 C67 C65 106(4) . . ?
N10 C67 H67 114.7 . . ?
N10 C67 H67A 104.5 . . ?
N10 C67 C65A 109(3) . . ?
C65 C67 H67 114.7 . . ?
C69 C67 N10 109(2) . . ?
C69 C67 C65 96(5) . . ?
C69 C67 H67 114.7 . . ?
C69 C67 H67A 104.5 . . ?
C69 C67 C65A 124(3) . . ?
C65A C67 H67A 104.5 . . ?
C67 C69 H69A 109.5 . . ?
C67 C69 H69B 109.5 . . ?
C67 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
N11 C70 H70A 108.4 . . ?
N11 C70 H70B 108.4 . . ?
N11 C70 C71 115(3) . . ?
H70A C70 H70B 107.5 . . ?
C71 C70 H70A 108.4 . . ?
C71 C70 H70B 108.4 . . ?
N12 C71 C70 109(2) . . ?
N12 C71 H71A 109.8 . . ?
N12 C71 H71B 109.8 . . ?
C70 C71 H71A 109.8 . . ?
C70 C71 H71B 109.8 . . ?
H71A C71 H71B 108.2 . . ?
N12 C72 H72A 109.6 . . ?
N12 C72 H72B 109.6 . . ?
N12 C72 C73 110(3) . . ?
H72A C72 H72B 108.2 . . ?
C73 C72 H72A 109.6 . . ?
C73 C72 H72B 109.6 . . ?
N11 C73 C72 113(2) . . ?
N11 C73 H73A 109.1 . . ?
N11 C73 H73B 109.1 . . ?
C72 C73 H73A 109.1 . . ?
C72 C73 H73B 109.1 . . ?
H73A C73 H73B 107.8 . . ?
N12 C74 H74A 109.5 . . ?
N12 C74 H74B 109.5 . . ?
N12 C74 H74C 109.5 . . ?
H74A C74 H74B 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C65A O16 C61 116(4) . . ?
C67 C65A H65C 105.7 . . ?
C67 C65A H65D 105.7 . . ?
O16 C65A C67 127(4) . . ?
O16 C65A H65C 105.7 . . ?
O16 C65A H65D 105.7 . . ?
H65C C65A H65D 106.1 . . ?
N9 C54 H54A 109.5 . . ?
N9 C54 H54B 109.5 . . ?
N9 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
H17C O17 H17D 98.3 . . ?
H18D O18 H18E 97.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C5 C4 C66 -176.5(17) . . . . ?
N1 C1 C2 C3 4(4) . . . . ?
N1 C1 C2 C10 179(2) . . . . ?
C1 N1 C8 C7 179.7(17) . . . . ?
C1 N1 C8 C66 -3(3) . . . . ?
C1 N1 C12 C11 157(2) . . . . ?
C1 N1 C12 C13 39(3) . . . . ?
C1 C2 C3 O3 179(2) . . . . ?
C1 C2 C3 C66 -3(3) . . . . ?
C1 C2 C10 O1 7(4) . . . . ?
C1 C2 C10 O2 178(2) . . . . ?
N2 C6 C5 F1 -6.4(16) . . . . ?
N2 C6 C5 C4 177.2(14) . . . . ?
N2 C14 C15 N3 54(4) . . . . ?
C2 C3 C66 C4 179.8(16) . . . . ?
C2 C3 C66 C8 -2(3) . . . . ?
O3 C3 C66 C4 -2(3) . . . . ?
O3 C3 C66 C8 176.2(17) . . . . ?
N3 C16 C17 N2 -51(4) . . . . ?
C3 C2 C10 O1 -178(3) . . . . ?
C3 C2 C10 O2 -7(3) . . . . ?
C3 C66 C8 N1 5(2) . . . . ?
C3 C66 C8 C7 -178.0(16) . . . . ?
O4 C7 C6 N2 6.2(16) . . . . ?
O4 C7 C6 C5 -176.8(13) . . . . ?
O4 C7 C8 N1 -6.6(18) . . . . ?
O4 C7 C8 C66 176.4(15) . . . . ?
O4 C11 C12 N1 53(3) . . . . ?
O4 C11 C12 C13 175(2) . . . . ?
C7 O4 C11 C12 -52(3) . . . . ?
C7 C6 C5 F1 176.4(17) . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C6 N2 C14 C15 110(4) . . . . ?
C6 N2 C17 C16 -111(3) . . . . ?
C6 C7 C8 N1 177.0(19) . . . . ?
C6 C7 C8 C66 0.0 . . . . ?
C6 C5 C4 C66 0.0 . . . . ?
C5 C4 C66 C3 178.0(15) . . . . ?
C5 C4 C66 C8 0.0 . . . . ?
C4 C66 C8 N1 -177(2) . . . . ?
C4 C66 C8 C7 0.0 . . . . ?
C8 N1 C1 C2 -1(3) . . . . ?
C8 N1 C12 C11 -29(3) . . . . ?
C8 N1 C12 C13 -147(2) . . . . ?
C8 C7 C6 N2 -177.0(15) . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C10 C2 C3 O3 5(4) . . . . ?
C10 C2 C3 C66 -176.9(19) . . . . ?
C11 O4 C7 C6 -153.8(17) . . . . ?
C11 O4 C7 C8 30(2) . . . . ?
C12 N1 C1 C2 172(2) . . . . ?
C12 N1 C8 C7 6(3) . . . . ?
C12 N1 C8 C66 -176.8(15) . . . . ?
C14 N2 C6 C7 -31(3) . . . . ?
C14 N2 C6 C5 152(2) . . . . ?
C14 N2 C17 C16 50(3) . . . . ?
C15 N3 C16 C17 56(5) . . . . ?
C16 N3 C15 C14 -56(3) . . . . ?
C17 N2 C6 C7 127(2) . . . . ?
C17 N2 C6 C5 -50(3) . . . . ?
C17 N2 C14 C15 -51(5) . . . . ?
C18 N3 C15 C14 178(2) . . . . ?
C18 N3 C16 C17 -175(5) . . . . ?
F2 C23 C22 C27 177.4(19) . . . . ?
N4 C19 C20 C21 -7(4) . . . . ?
N4 C19 C20 C28 175(2) . . . . ?
N4 C26 C25 O8 12.9(19) . . . . ?
N4 C26 C25 C24 -171(2) . . . . ?
N5 C24 C23 F2 5.7(18) . . . . ?
N5 C24 C23 C22 -176.9(16) . . . . ?
N5 C32 C33 N6 -60(4) . . . . ?
N5 C34 C35 N6 50(5) . . . . ?
O7 C21 C27 C26 -178.1(16) . . . . ?
O7 C21 C27 C22 1(3) . . . . ?
O8 C25 C24 N5 -7(2) . . . . ?
O8 C25 C24 C23 176.1(15) . . . . ?
O8 C29 C30 N4 65(4) . . . . ?
O8 C29 C30 C31 -169(3) . . . . ?
C19 N4 C26 C27 14(3) . . . . ?
C19 N4 C26 C25 -174.6(15) . . . . ?
C19 N4 C30 C29 135(3) . . . . ?
C19 N4 C30 C31 8(4) . . . . ?
C19 C20 C21 O7 -173.9(19) . . . . ?
C19 C20 C21 C27 10(4) . . . . ?
C19 C20 C28 O5 0(4) . . . . ?
C19 C20 C28 O6 176(2) . . . . ?
C20 C21 C27 C26 -2(3) . . . . ?
C20 C21 C27 C22 177(2) . . . . ?
C21 C20 C28 O5 -178(3) . . . . ?
C21 C20 C28 O6 -3(3) . . . . ?
C21 C27 C26 N4 -10.1(19) . . . . ?
C21 C27 C26 C25 179.2(16) . . . . ?
C21 C27 C22 C23 -179.1(17) . . . . ?
C27 C26 C25 O8 -176.1(15) . . . . ?
C27 C26 C25 C24 0.0 . . . . ?
C26 N4 C19 C20 -5(4) . . . . ?
C26 N4 C30 C29 -51(5) . . . . ?
C26 N4 C30 C31 -177(2) . . . . ?
C26 C27 C22 C23 0.0 . . . . ?
C26 C25 C24 N5 176.8(17) . . . . ?
C26 C25 C24 C23 0.0 . . . . ?
C25 O8 C29 C30 -43(3) . . . . ?
C25 C24 C23 F2 -177.4(19) . . . . ?
C25 C24 C23 C22 0.0 . . . . ?
C24 N5 C32 C33 -106(4) . . . . ?
C24 N5 C34 C35 115(3) . . . . ?
C24 C23 C22 C27 0.0 . . . . ?
C22 C27 C26 N4 171(2) . . . . ?
C22 C27 C26 C25 0.0 . . . . ?
C28 C20 C21 O7 5(4) . . . . ?
C28 C20 C21 C27 -171.0(18) . . . . ?
C29 O8 C25 C26 5(2) . . . . ?
C29 O8 C25 C24 -171.2(17) . . . . ?
C30 N4 C19 C20 169(3) . . . . ?
C30 N4 C26 C27 -160.2(17) . . . . ?
C30 N4 C26 C25 11(3) . . . . ?
C32 N5 C24 C25 31(3) . . . . ?
C32 N5 C24 C23 -152.1(19) . . . . ?
C32 N5 C34 C35 -42(4) . . . . ?
C33 N6 C35 C34 -57(5) . . . . ?
C34 N5 C24 C25 -122(2) . . . . ?
C34 N5 C24 C23 54(3) . . . . ?
C34 N5 C32 C33 48(5) . . . . ?
C35 N6 C33 C32 63(3) . . . . ?
C36 N6 C33 C32 -179(2) . . . . ?
C36 N6 C35 C34 -179(5) . . . . ?
F3 C41 C40 C45 178.5(18) . . . . ?
N7 C37 C38 C9 177(3) . . . . ?
N7 C37 C38 C39 -3(4) . . . . ?
N7 C44 C43 O12 -2.0(17) . . . . ?
N7 C44 C43 C42 -178.6(17) . . . . ?
N8 C42 C41 F3 -0.9(17) . . . . ?
N8 C42 C41 C40 177.7(15) . . . . ?
N8 C42 C43 O12 5.7(17) . . . . ?
N8 C42 C43 C44 -177.7(14) . . . . ?
N8 C50 C51 N9 -60(5) . . . . ?
C9 C38 C39 O11 8(4) . . . . ?
C9 C38 C39 C45 -173(2) . . . . ?
N9 C52 C53 N8 49(6) . . . . ?
O9 C9 C38 C37 -1(5) . . . . ?
O9 C9 C38 C39 178(3) . . . . ?
O10 C9 C38 C37 -179(3) . . . . ?
O10 C9 C38 C39 0(4) . . . . ?
O11 C39 C45 C40 -7(3) . . . . ?
O11 C39 C45 C44 176.5(17) . . . . ?
O12 C47 C48 N7 65(3) . . . . ?
O12 C47 C48 C49 -176(3) . . . . ?
C37 N7 C44 C45 9(2) . . . . ?
C37 N7 C44 C43 -172.3(14) . . . . ?
C37 N7 C48 C47 146(3) . . . . ?
C37 N7 C48 C49 23(4) . . . . ?
C37 C38 C39 O11 -173(2) . . . . ?
C37 C38 C39 C45 6(3) . . . . ?
C38 C39 C45 C40 173.9(17) . . . . ?
C38 C39 C45 C44 -3(3) . . . . ?
C39 C45 C44 N7 -5.0(19) . . . . ?
C39 C45 C44 C43 176.4(16) . . . . ?
C42 N8 C50 C51 -116(4) . . . . ?
C42 N8 C53 C52 120(4) . . . . ?
C42 C41 C40 C45 0.0 . . . . ?
C41 C42 C43 O12 -176.6(14) . . . . ?
C41 C42 C43 C44 0.0 . . . . ?
C41 C40 C45 C39 -176.6(15) . . . . ?
C41 C40 C45 C44 0.0 . . . . ?
C40 C45 C44 N7 178.6(17) . . . . ?
C40 C45 C44 C43 0.0 . . . . ?
C45 C44 C43 O12 176.6(15) . . . . ?
C45 C44 C43 C42 0.0 . . . . ?
C44 N7 C37 C38 -5(3) . . . . ?
C44 N7 C48 C47 -39(3) . . . . ?
C44 N7 C48 C49 -161(2) . . . . ?
C43 O12 C47 C48 -59(3) . . . . ?
C43 C42 C41 F3 -178.5(17) . . . . ?
C43 C42 C41 C40 0.0 . . . . ?
C47 O12 C43 C42 -157.9(18) . . . . ?
C47 O12 C43 C44 25(2) . . . . ?
C48 N7 C37 C38 171(2) . . . . ?
C48 N7 C44 C45 -167.2(15) . . . . ?
C48 N7 C44 C43 11(2) . . . . ?
C50 N8 C42 C41 -140(3) . . . . ?
C50 N8 C42 C43 38(4) . . . . ?
C50 N8 C53 C52 -49(5) . . . . ?
C51 N9 C52 C53 -55(6) . . . . ?
C52 N9 C51 C50 61(4) . . . . ?
C53 N8 C42 C41 54(3) . . . . ?
C53 N8 C42 C43 -128(3) . . . . ?
C53 N8 C50 C51 52(6) . . . . ?
F4 C59 C58 C63 -175.7(18) . . . . ?
N10 C55 C56 C57 -1(4) . . . . ?
N10 C55 C56 C64 -178(2) . . . . ?
N10 C62 C61 C60 -179.5(19) . . . . ?
N10 C62 C61 O16A 23(3) . . . . ?
N10 C62 C61 O16 -1(2) . . . . ?
N10 C67 C65A O16 -36(7) . . . . ?
N11 C60 C59 F4 -3.3(18) . . . . ?
N11 C60 C59 C58 -178.8(16) . . . . ?
N11 C70 C71 N12 -51(5) . . . . ?
N12 C72 C73 N11 57(5) . . . . ?
O15 C57 C63 C62 -175.4(16) . . . . ?
O15 C57 C63 C58 3(3) . . . . ?
C55 N10 C62 C63 2(3) . . . . ?
C55 N10 C62 C61 -178.8(15) . . . . ?
C55 N10 C67 C65 157(5) . . . . ?
C55 N10 C67 C69 55(3) . . . . ?
C55 N10 C67 C65A -168(3) . . . . ?
C55 C56 C57 O15 177.2(18) . . . . ?
C55 C56 C57 C63 0(3) . . . . ?
C55 C56 C64 O13 -1(4) . . . . ?
C55 C56 C64 O14 177(2) . . . . ?
C56 C57 C63 C62 1(3) . . . . ?
C56 C57 C63 C58 179.5(17) . . . . ?
C57 C56 C64 O13 -177(3) . . . . ?
C57 C56 C64 O14 0(4) . . . . ?
C57 C63 C62 N10 -2.4(18) . . . . ?
C57 C63 C62 C61 178.1(15) . . . . ?
C57 C63 C58 C59 -178.1(15) . . . . ?
C63 C62 C61 C60 0.0 . . . . ?
C63 C62 C61 O16A -158(3) . . . . ?
C63 C62 C61 O16 178.2(16) . . . . ?
C62 N10 C55 C56 0(3) . . . . ?
C62 N10 C67 C65 -29(5) . . . . ?
C62 N10 C67 C69 -132(3) . . . . ?
C62 N10 C67 C65A 6(3) . . . . ?
C62 C63 C58 C59 0.0 . . . . ?
C62 C61 C60 N11 178.8(17) . . . . ?
C62 C61 C60 C59 0.0 . . . . ?
C62 C61 O16A C65 -29(13) . . . . ?
C62 C61 O16 C65A -24(5) . . . . ?
C61 C60 C59 F4 175.5(19) . . . . ?
C61 C60 C59 C58 0.0 . . . . ?
C61 O16A C65 C67 3(21) . . . . ?
C61 O16 C65A C67 45(7) . . . . ?
C60 N11 C70 C71 -117(3) . . . . ?
C60 N11 C73 C72 115(4) . . . . ?
C60 C61 O16A C65 174(11) . . . . ?
C60 C61 O16 C65A 154(4) . . . . ?
C60 C59 C58 C63 0.0 . . . . ?
C58 C63 C62 N10 179.5(19) . . . . ?
C58 C63 C62 C61 0.0 . . . . ?
C64 C56 C57 O15 -6(4) . . . . ?
C64 C56 C57 C63 177.2(19) . . . . ?
O16A C61 C60 N11 -26(4) . . . . ?
O16A C61 C60 C59 155(3) . . . . ?
O16A C65 C67 N10 27(17) . . . . ?
O16A C65 C67 C69 138(15) . . . . ?
C67 N10 C55 C56 174(2) . . . . ?
C67 N10 C62 C63 -172.2(15) . . . . ?
C67 N10 C62 C61 7(3) . . . . ?
C69 C67 C65A O16 94(7) . . . . ?
C70 N11 C60 C61 134(3) . . . . ?
C70 N11 C60 C59 -48(3) . . . . ?
C70 N11 C73 C72 -51(5) . . . . ?
C71 N12 C72 C73 -59(3) . . . . ?
C72 N12 C71 C70 56(5) . . . . ?
C73 N11 C60 C61 -31(3) . . . . ?
C73 N11 C60 C59 148(3) . . . . ?
C73 N11 C70 C71 49(4) . . . . ?
C74 N12 C71 C70 177(4) . . . . ?
C74 N12 C72 C73 -178(2) . . . . ?
O16 C61 C60 N11 1(2) . . . . ?
O16 C61 C60 C59 -178.2(17) . . . . ?
C54 N9 C51 C50 -177(3) . . . . ?
C54 N9 C52 C53 -174(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_LH_PE_2p19
_database_code_depnum_ccdc_archive 'CCDC 2481333'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_Levo_HH_20241010_iaintest

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.25(H4 O2)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   27.878(3)
_cell_length_b                   6.4360(6)
_cell_length_c                   18.107(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.447(8)
_cell_angle_gamma                90
_cell_volume                     2980.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7275
_cell_measurement_theta_min      2.365
_cell_measurement_theta_max      23.252
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.997
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon III'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7275
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.365
_diffrn_reflns_theta_max         23.252
_diffrn_reflns_theta_full        23.252
_diffrn_measured_fraction_theta_max 0.615
_diffrn_measured_fraction_theta_full 0.615
_diffrn_reflns_Laue_measured_fraction_max 0.615
_diffrn_reflns_Laue_measured_fraction_full 0.615
_diffrn_reflns_point_group_measured_fraction_max 0.584
_diffrn_reflns_point_group_measured_fraction_full 0.584
_reflns_number_total             2495
_reflns_number_gt                1706
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.545
_reflns_Friedel_fraction_full    0.545
_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_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'

_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0995P)²+3.0488P] 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_abs_structure_details 
;
 Flack x determined using 560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2495
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1835
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      2.328
_refine_ls_shift/su_max          0.756
_refine_ls_shift/su_mean         0.035
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 0.20916(19) 0.4459(8) 0.7276(6) 0.0390(16) Uiso 1 1 d D U . . .
O1 O 0.3209(3) 0.4688(11) 1.2310(7) 0.048(2) Uiso 1 1 d D U . . .
O2 O 0.3750(2) 0.4664(11) 1.1668(6) 0.0371(19) Uiso 1 1 d D U . . .
H2 H 0.371804 0.463467 1.119807 0.056 Uiso 1 1 calc R U . . .
O3 O 0.3371(2) 0.4759(9) 1.0150(6) 0.0271(18) Uiso 1 1 d D U . . .
O4 O 0.1015(2) 0.4463(10) 0.8724(6) 0.0318(17) Uiso 1 1 d D U . . .
N1 N 0.1912(2) 0.4585(11) 1.0182(7) 0.026(2) Uiso 1 1 d D U . . .
N2 N 0.1111(2) 0.4657(11) 0.7246(6) 0.025(2) Uiso 1 1 d D U . . .
N3 N 0.0130(3) 0.6406(11) 0.6251(7) 0.029(2) Uiso 1 1 d D U . . .
C1 C 0.2342(3) 0.4589(14) 1.0869(8) 0.031(3) Uiso 1 1 d D U . . .
H1 H 0.230233 0.454246 1.135532 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2840(3) 0.4657(13) 1.0886(7) 0.021(2) Uiso 1 1 d D U . . .
C3 C 0.2917(3) 0.4693(13) 1.0154(7) 0.018(2) Uiso 1 1 d D U . . .
C4 C 0.2495(3) 0.4600(13) 0.8675(7) 0.023(2) Uiso 1 1 d D U . . .
H4 H 0.282232 0.458038 0.865056 0.027 Uiso 1 1 calc R U . . .
C5 C 0.2054(3) 0.4579(14) 0.7992(7) 0.028(3) Uiso 1 1 d D U . . .
C6 C 0.1540(3) 0.4607(13) 0.7967(7) 0.019(2) Uiso 1 1 d D U . . .
C7 C 0.1508(3) 0.4549(13) 0.8713(7) 0.019(2) Uiso 1 1 d D U . . .
C8 C 0.1952(3) 0.4588(13) 0.9434(7) 0.020(2) Uiso 1 1 d D U . . .
C9 C 0.2452(3) 0.4651(13) 0.9414(7) 0.020(2) Uiso 1 1 d D U . . .
C10 C 0.3277(3) 0.4686(14) 1.1693(7) 0.026(3) Uiso 1 1 d D U . . .
C11 C 0.0995(3) 0.5344(15) 0.9427(7) 0.033(3) Uiso 1 1 d D U . . .
H11A H 0.064584 0.516642 0.941158 0.040 Uiso 1 1 calc R U . . .
H11B H 0.106271 0.682372 0.943180 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1382(3) 0.4397(14) 1.0189(7) 0.028(2) Uiso 1 1 d D U . . .
H12 H 0.129779 0.292672 1.021280 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1343(4) 0.5543(16) 1.0890(8) 0.038(3) Uiso 1 1 d D U . . .
H13A H 0.154826 0.483745 1.138165 0.058 Uiso 1 1 calc R U . . .
H13B H 0.098436 0.558656 1.082579 0.058 Uiso 1 1 calc R U . . .
H13C H 0.147137 0.693404 1.090741 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0624(3) 0.3573(13) 0.7096(9) 0.029(3) Uiso 1 1 d D U . . .
H14A H 0.066376 0.272473 0.755902 0.035 Uiso 1 1 calc R U . . .
H14B H 0.054340 0.265965 0.663560 0.035 Uiso 1 1 calc R U . . .
C15 C 0.0177(3) 0.5086(13) 0.6934(8) 0.029(3) Uiso 1 1 d D U . . .
H15A H -0.014573 0.432904 0.681414 0.035 Uiso 1 1 calc R U . . .
H15B H 0.024349 0.593685 0.740622 0.035 Uiso 1 1 calc R U . . .
C16 C 0.0613(3) 0.7612(14) 0.6454(10) 0.036(3) Uiso 1 1 d D U . . .
H16A H 0.067128 0.847029 0.692247 0.043 Uiso 1 1 calc R U . . .
H16B H 0.058084 0.851761 0.600874 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1071(3) 0.6151(14) 0.6628(8) 0.033(3) Uiso 1 1 d D U . . .
H17A H 0.103014 0.541876 0.613854 0.040 Uiso 1 1 calc R U . . .
H17B H 0.139134 0.695223 0.679930 0.040 Uiso 1 1 calc R U . . .
C18 C -0.0314(4) 0.7836(15) 0.6030(12) 0.046(3) Uiso 1 1 d D U . . .
H18A H -0.063330 0.705578 0.586169 0.069 Uiso 1 1 calc R U . . .
H18B H -0.032098 0.871260 0.559677 0.069 Uiso 1 1 calc R U . . .
H18C H -0.027868 0.867858 0.648634 0.069 Uiso 1 1 calc R U . . .
F2 F 0.28606(19) 0.7317(8) 0.7635(6) 0.0363(16) Uiso 1 1 d D U . . .
O5 O 0.1846(3) 0.7019(12) 0.2624(7) 0.054(2) Uiso 1 1 d D U . . .
O6 O 0.1283(2) 0.7168(12) 0.3213(6) 0.041(2) Uiso 1 1 d D U . . .
H6 H 0.130197 0.715978 0.367621 0.062 Uiso 1 1 calc R U . . .
O7 O 0.1622(2) 0.6799(9) 0.4729(6) 0.0306(18) Uiso 1 1 d D U . . .
O8 O 0.3976(2) 0.6972(9) 0.6273(6) 0.0336(19) Uiso 1 1 d D U . . .
N4 N 0.3102(3) 0.6636(10) 0.4793(7) 0.026(2) Uiso 1 1 d D U . . .
N5 N 0.3847(3) 0.7190(12) 0.7713(6) 0.029(2) Uiso 1 1 d D U . . .
N6 N 0.4838(2) 0.5855(11) 0.8806(7) 0.030(2) Uiso 1 1 d D U . . .
C19 C 0.2685(3) 0.6664(13) 0.4097(8) 0.033(3) Uiso 1 1 d D U . . .
H19 H 0.273842 0.653903 0.362414 0.039 Uiso 1 1 calc R U . . .
C20 C 0.2183(3) 0.6865(13) 0.4036(7) 0.025(3) Uiso 1 1 d D U . . .
C21 C 0.2082(3) 0.6813(13) 0.4744(7) 0.024(3) Uiso 1 1 d D U . . .
C22 C 0.2479(3) 0.6942(13) 0.6241(7) 0.025(2) Uiso 1 1 d D U . . .
H22 H 0.214991 0.691616 0.625589 0.030 Uiso 1 1 calc R U . . .
C23 C 0.2912(3) 0.7086(14) 0.6930(7) 0.028(3) Uiso 1 1 d D U . . .
C24 C 0.3429(3) 0.7075(13) 0.6973(7) 0.021(2) Uiso 1 1 d D U . . .
C25 C 0.3476(3) 0.7000(13) 0.6234(7) 0.021(2) Uiso 1 1 d D U . . .
C26 C 0.3036(3) 0.6854(13) 0.5508(7) 0.021(2) Uiso 1 1 d D U . . .
C27 C 0.2530(3) 0.6835(13) 0.5513(7) 0.023(3) Uiso 1 1 d D U . . .
C28 C 0.1757(3) 0.7013(14) 0.3220(7) 0.028(3) Uiso 1 1 d D U . . .
C29 C 0.4003(3) 0.7450(14) 0.5517(7) 0.031(3) Uiso 1 1 d D U . . .
H29A H 0.435748 0.723298 0.556025 0.037 Uiso 1 1 calc R U . . .
H29B H 0.391580 0.890157 0.538962 0.037 Uiso 1 1 calc R U . . .
C30 C 0.3637(3) 0.6128(14) 0.4853(8) 0.028(2) Uiso 1 1 d D U . . .
H30 H 0.370958 0.466539 0.500739 0.034 Uiso 1 1 calc R U . . .
C31 C 0.3690(4) 0.6460(18) 0.4063(9) 0.049(3) Uiso 1 1 d D U . . .
H31A H 0.349679 0.540626 0.368721 0.074 Uiso 1 1 calc R U . . .
H31B H 0.405187 0.638172 0.414831 0.074 Uiso 1 1 calc R U . . .
H31C H 0.355424 0.780369 0.385217 0.074 Uiso 1 1 calc R U . . .
C32 C 0.4311(3) 0.8426(13) 0.7862(9) 0.027(2) Uiso 1 1 d D U . . .
H32A H 0.435287 0.942814 0.828349 0.032 Uiso 1 1 calc R U . . .
H32B H 0.426885 0.918637 0.737779 0.032 Uiso 1 1 calc R U . . .
C33 C 0.4793(3) 0.7084(14) 0.8111(8) 0.032(3) Uiso 1 1 d D U . . .
H33A H 0.476978 0.617433 0.767068 0.039 Uiso 1 1 calc R U . . .
H33B H 0.510069 0.795189 0.824241 0.039 Uiso 1 1 calc R U . . .
C34 C 0.4378(3) 0.4507(14) 0.8599(9) 0.034(3) Uiso 1 1 d D U . . .
H34A H 0.441616 0.363540 0.905624 0.041 Uiso 1 1 calc R U . . .
H34B H 0.435089 0.360981 0.815376 0.041 Uiso 1 1 calc R U . . .
C35 C 0.3890(3) 0.5793(14) 0.8369(8) 0.034(3) Uiso 1 1 d D U . . .
H35A H 0.358631 0.488954 0.820178 0.041 Uiso 1 1 calc R U . . .
H35B H 0.390107 0.659235 0.882965 0.041 Uiso 1 1 calc R U . . .
C36 C 0.5315(3) 0.4603(16) 0.9074(12) 0.044(3) Uiso 1 1 d D U . . .
H36A H 0.532437 0.382860 0.862665 0.066 Uiso 1 1 calc R U . . .
H36B H 0.531876 0.365958 0.948689 0.066 Uiso 1 1 calc R U . . .
H36C H 0.561444 0.549841 0.928336 0.066 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.3509(17) 0.500000 0.053(3) Uiso 1 2 d DGS . P . .
H9A H -0.003576 0.442034 0.466371 0.080 Uiso 0.5 1 d DG U P . .
H9B H -0.001912 0.241552 0.474943 0.080 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.395(2) 1.000000 0.056(3) Uiso 1 2 d DGS . P . .
H10A H -0.002516 0.321239 0.961710 0.083 Uiso 0.5 1 d DG U P . .
H10B H 0.012071 0.315289 1.038619 0.083 Uiso 0.5 1 d DG U P . .
_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 C5 1.344(10) . ?
O1 C10 1.204(11) . ?
O2 C10 1.338(9) . ?
O2 H2 0.8200 . ?
O3 C3 1.269(8) . ?
O4 C7 1.383(8) . ?
O4 C11 1.415(11) . ?
N1 C1 1.341(10) . ?
N1 C8 1.403(10) . ?
N1 C12 1.486(9) . ?
N2 C6 1.376(10) . ?
N2 C17 1.445(11) . ?
N2 C14 1.452(8) . ?
N3 C15 1.461(11) . ?
N3 C18 1.464(9) . ?
N3 C16 1.469(9) . ?
C1 C2 1.376(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.425(11) . ?
C2 C10 1.484(11) . ?
C3 C9 1.448(10) . ?
C4 C5 1.355(10) . ?
C4 C9 1.392(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(9) . ?
C6 C7 1.389(10) . ?
C7 C8 1.399(10) . ?
C8 C9 1.407(9) . ?
C11 C12 1.501(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.514(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.514(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.348(10) . ?
O5 C28 1.200(11) . ?
O6 C28 1.319(9) . ?
O6 H6 0.8200 . ?
O7 C21 1.272(9) . ?
O8 C25 1.367(8) . ?
O8 C29 1.433(11) . ?
N4 C19 1.332(10) . ?
N4 C26 1.387(10) . ?
N4 C30 1.488(9) . ?
N5 C24 1.385(10) . ?
N5 C32 1.449(9) . ?
N5 C35 1.456(11) . ?
N6 C33 1.450(11) . ?
N6 C36 1.463(9) . ?
N6 C34 1.468(9) . ?
C19 C20 1.365(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.417(11) . ?
C20 C28 1.484(11) . ?
C21 C27 1.454(11) . ?
C22 C23 1.350(10) . ?
C22 C27 1.382(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.411(10) . ?
C24 C25 1.398(11) . ?
C25 C26 1.399(10) . ?
C26 C27 1.413(10) . ?
C29 C30 1.495(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.510(12) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.509(9) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.503(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8227 . ?
O9 H9B 0.8272 . ?
O9 H9A 0.8(2) 2_556 ?
O9 H9B 0.83(19) 2_556 ?
O10 H10A 0.8183 . ?
O10 H10B 0.8218 . ?
O10 H10A 0.8(3) 2_557 ?
O10 H10B 0.8(3) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 113.1(8) . . ?
C1 N1 C8 120.6(8) . . ?
C1 N1 C12 121.2(10) . . ?
C8 N1 C12 118.0(8) . . ?
C6 N2 C17 121.3(8) . . ?
C6 N2 C14 124.1(9) . . ?
C17 N2 C14 113.4(8) . . ?
C15 N3 C18 112.3(10) . . ?
C15 N3 C16 109.2(8) . . ?
C18 N3 C16 109.1(7) . . ?
N1 C1 C2 122.9(11) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 120.2(9) . . ?
C1 C2 C10 116.6(10) . . ?
C3 C2 C10 123.2(8) . . ?
O3 C3 C2 121.7(9) . . ?
O3 C3 C9 121.5(10) . . ?
C2 C3 C9 116.7(8) . . ?
C5 C4 C9 118.9(9) . . ?
C5 C4 H4 120.6 . . ?
C9 C4 H4 120.6 . . ?
F1 C5 C4 119.3(9) . . ?
F1 C5 C6 115.9(9) . . ?
C4 C5 C6 124.7(10) . . ?
N2 C6 C7 123.7(8) . . ?
N2 C6 C5 121.1(10) . . ?
C7 C6 C5 115.1(9) . . ?
O4 C7 C6 117.6(8) . . ?
O4 C7 C8 120.2(10) . . ?
C6 C7 C8 122.2(8) . . ?
C7 C8 N1 121.3(8) . . ?
C7 C8 C9 119.6(10) . . ?
N1 C8 C9 119.1(8) . . ?
C4 C9 C8 119.4(9) . . ?
C4 C9 C3 120.1(8) . . ?
C8 C9 C3 120.5(10) . . ?
O1 C10 O2 123.5(10) . . ?
O1 C10 C2 122.8(9) . . ?
O2 C10 C2 113.6(10) . . ?
O4 C11 C12 113.1(8) . . ?
O4 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
O4 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 C11 108.2(8) . . ?
N1 C12 C13 111.8(8) . . ?
C11 C12 C13 107.9(8) . . ?
N1 C12 H12 109.6 . . ?
C11 C12 H12 109.6 . . ?
C13 C12 H12 109.6 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.2(7) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 109.2(9) . . ?
N3 C15 H15A 109.8 . . ?
C14 C15 H15A 109.9 . . ?
N3 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N3 C16 C17 109.7(7) . . ?
N3 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
N3 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
N2 C17 C16 111.9(9) . . ?
N2 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
N2 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 112.8(8) . . ?
C19 N4 C26 119.4(8) . . ?
C19 N4 C30 123.0(10) . . ?
C26 N4 C30 117.1(8) . . ?
C24 N5 C32 123.7(9) . . ?
C24 N5 C35 121.3(8) . . ?
C32 N5 C35 114.2(8) . . ?
C33 N6 C36 109.9(10) . . ?
C33 N6 C34 109.6(9) . . ?
C36 N6 C34 110.2(7) . . ?
N4 C19 C20 124.0(11) . . ?
N4 C19 H19 118.0 . . ?
C20 C19 H19 118.0 . . ?
C19 C20 C21 119.3(9) . . ?
C19 C20 C28 118.3(10) . . ?
C21 C20 C28 122.3(8) . . ?
O7 C21 C20 122.8(9) . . ?
O7 C21 C27 119.6(10) . . ?
C20 C21 C27 117.6(8) . . ?
C23 C22 C27 119.6(9) . . ?
C23 C22 H22 120.2 . . ?
C27 C22 H22 120.2 . . ?
F2 C23 C22 119.4(9) . . ?
F2 C23 C24 116.0(9) . . ?
C22 C23 C24 124.5(11) . . ?
N5 C24 C25 124.4(8) . . ?
N5 C24 C23 120.1(10) . . ?
C25 C24 C23 115.6(9) . . ?
O8 C25 C24 115.7(8) . . ?
O8 C25 C26 122.9(10) . . ?
C24 C25 C26 121.2(8) . . ?
N4 C26 C25 119.3(8) . . ?
N4 C26 C27 120.6(9) . . ?
C25 C26 C27 120.0(10) . . ?
C22 C27 C26 119.0(9) . . ?
C22 C27 C21 122.7(8) . . ?
C26 C27 C21 118.2(10) . . ?
O5 C28 O6 123.7(10) . . ?
O5 C28 C20 121.7(9) . . ?
O6 C28 C20 114.6(10) . . ?
O8 C29 C30 111.6(8) . . ?
O8 C29 H29A 109.3 . . ?
C30 C29 H29A 109.3 . . ?
O8 C29 H29B 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
N4 C30 C29 106.1(8) . . ?
N4 C30 C31 111.9(9) . . ?
C29 C30 C31 112.9(9) . . ?
N4 C30 H30 108.6 . . ?
C29 C30 H30 108.6 . . ?
C31 C30 H30 108.6 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 111.4(7) . . ?
N5 C32 H32A 109.3 . . ?
C33 C32 H32A 109.4 . . ?
N5 C32 H32B 109.4 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
N6 C33 C32 109.3(9) . . ?
N6 C33 H33A 109.9 . . ?
C32 C33 H33A 109.8 . . ?
N6 C33 H33B 109.8 . . ?
C32 C33 H33B 109.8 . . ?
H33A C33 H33B 108.3 . . ?
N6 C34 C35 110.4(7) . . ?
N6 C34 H34A 109.5 . . ?
C35 C34 H34A 109.5 . . ?
N6 C34 H34B 109.6 . . ?
C35 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N5 C35 C34 109.7(9) . . ?
N5 C35 H35A 109.7 . . ?
C34 C35 H35A 109.7 . . ?
N5 C35 H35B 109.7 . . ?
C34 C35 H35B 109.8 . . ?
H35A C35 H35B 108.2 . . ?
N6 C36 H36A 109.6 . . ?
N6 C36 H36B 109.4 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 103.8 . . ?
H9A O9 H9A 89.0 . 2_556 ?
H9B O9 H9A 167.1 . 2_556 ?
H9A O9 H9B 167.2 . 2_556 ?
H9B O9 H9B 63.5 . 2_556 ?
H9A O9 H9B 103.8 2_556 2_556 ?
H10A O10 H10B 103.3 . . ?
H10A O10 H10A 109.6 . 2_557 ?
H10B O10 H10A 18.7 . 2_557 ?
H10A O10 H10B 18.7 . 2_557 ?
H10B O10 H10B 103.2 . 2_557 ?
H10A O10 H10B 103.3 2_557 2_557 ?
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
C8 N1 C1 C2 2.0(14) . . . . ?
C12 N1 C1 C2 176.7(8) . . . . ?
N1 C1 C2 C3 -1.1(14) . . . . ?
N1 C1 C2 C10 179.0(8) . . . . ?
C1 C2 C3 O3 179.9(8) . . . . ?
C10 C2 C3 O3 -0.3(13) . . . . ?
C1 C2 C3 C9 -0.1(13) . . . . ?
C10 C2 C3 C9 179.8(7) . . . . ?
C9 C4 C5 F1 -177.7(8) . . . . ?
C9 C4 C5 C6 0.0(14) . . . . ?
C17 N2 C6 C7 131.1(10) . . . . ?
C14 N2 C6 C7 -35.7(14) . . . . ?
C17 N2 C6 C5 -49.9(13) . . . . ?
C14 N2 C6 C5 143.3(9) . . . . ?
F1 C5 C6 N2 -4.5(13) . . . . ?
C4 C5 C6 N2 177.7(9) . . . . ?
F1 C5 C6 C7 174.6(8) . . . . ?
C4 C5 C6 C7 -3.2(13) . . . . ?
C11 O4 C7 C6 -152.5(8) . . . . ?
C11 O4 C7 C8 27.1(12) . . . . ?
N2 C6 C7 O4 2.4(13) . . . . ?
C5 C6 C7 O4 -176.7(8) . . . . ?
N2 C6 C7 C8 -177.2(8) . . . . ?
C5 C6 C7 C8 3.7(13) . . . . ?
O4 C7 C8 N1 -1.4(13) . . . . ?
C6 C7 C8 N1 178.2(8) . . . . ?
O4 C7 C8 C9 179.3(8) . . . . ?
C6 C7 C8 C9 -1.2(13) . . . . ?
C1 N1 C8 C7 178.9(8) . . . . ?
C12 N1 C8 C7 4.0(12) . . . . ?
C1 N1 C8 C9 -1.7(13) . . . . ?
C12 N1 C8 C9 -176.6(7) . . . . ?
C5 C4 C9 C8 2.8(13) . . . . ?
C5 C4 C9 C3 -179.4(8) . . . . ?
C7 C8 C9 C4 -2.2(13) . . . . ?
N1 C8 C9 C4 178.4(8) . . . . ?
C7 C8 C9 C3 180.0(8) . . . . ?
N1 C8 C9 C3 0.6(13) . . . . ?
O3 C3 C9 C4 2.5(13) . . . . ?
C2 C3 C9 C4 -177.5(8) . . . . ?
O3 C3 C9 C8 -179.7(8) . . . . ?
C2 C3 C9 C8 0.3(12) . . . . ?
C1 C2 C10 O1 -1.3(13) . . . . ?
C3 C2 C10 O1 178.8(9) . . . . ?
C1 C2 C10 O2 177.3(8) . . . . ?
C3 C2 C10 O2 -2.5(12) . . . . ?
C7 O4 C11 C12 -55.5(11) . . . . ?
C1 N1 C12 C11 155.6(8) . . . . ?
C8 N1 C12 C11 -29.5(11) . . . . ?
C1 N1 C12 C13 36.8(12) . . . . ?
C8 N1 C12 C13 -148.3(9) . . . . ?
O4 C11 C12 N1 55.8(10) . . . . ?
O4 C11 C12 C13 176.9(7) . . . . ?
C6 N2 C14 C15 115.6(11) . . . . ?
C17 N2 C14 C15 -52.1(14) . . . . ?
C18 N3 C15 C14 176.8(9) . . . . ?
C16 N3 C15 C14 -62.0(10) . . . . ?
N2 C14 C15 N3 57.3(13) . . . . ?
C15 N3 C16 C17 60.8(13) . . . . ?
C18 N3 C16 C17 -176.1(13) . . . . ?
C6 N2 C17 C16 -117.1(10) . . . . ?
C14 N2 C17 C16 51.0(12) . . . . ?
N3 C16 C17 N2 -54.8(14) . . . . ?
C26 N4 C19 C20 -1.1(13) . . . . ?
C30 N4 C19 C20 171.4(8) . . . . ?
N4 C19 C20 C21 -7.4(14) . . . . ?
N4 C19 C20 C28 176.0(8) . . . . ?
C19 C20 C21 O7 -173.4(8) . . . . ?
C28 C20 C21 O7 3.1(14) . . . . ?
C19 C20 C21 C27 8.3(13) . . . . ?
C28 C20 C21 C27 -175.1(7) . . . . ?
C27 C22 C23 F2 176.0(8) . . . . ?
C27 C22 C23 C24 -2.0(14) . . . . ?
C32 N5 C24 C25 39.0(13) . . . . ?
C35 N5 C24 C25 -130.5(10) . . . . ?
C32 N5 C24 C23 -139.2(9) . . . . ?
C35 N5 C24 C23 51.3(13) . . . . ?
F2 C23 C24 N5 3.2(13) . . . . ?
C22 C23 C24 N5 -178.8(8) . . . . ?
F2 C23 C24 C25 -175.1(7) . . . . ?
C22 C23 C24 C25 2.9(13) . . . . ?
C29 O8 C25 C24 -164.4(7) . . . . ?
C29 O8 C25 C26 18.9(11) . . . . ?
N5 C24 C25 O8 2.3(13) . . . . ?
C23 C24 C25 O8 -179.5(7) . . . . ?
N5 C24 C25 C26 179.1(8) . . . . ?
C23 C24 C25 C26 -2.7(13) . . . . ?
C19 N4 C26 C25 -174.7(7) . . . . ?
C30 N4 C26 C25 12.5(11) . . . . ?
C19 N4 C26 C27 8.2(12) . . . . ?
C30 N4 C26 C27 -164.7(7) . . . . ?
O8 C25 C26 N4 1.1(12) . . . . ?
C24 C25 C26 N4 -175.5(8) . . . . ?
O8 C25 C26 C27 178.2(8) . . . . ?
C24 C25 C26 C27 1.7(12) . . . . ?
C23 C22 C27 C26 0.7(13) . . . . ?
C23 C22 C27 C21 -175.9(7) . . . . ?
N4 C26 C27 C22 176.5(8) . . . . ?
C25 C26 C27 C22 -0.6(13) . . . . ?
N4 C26 C27 C21 -6.7(12) . . . . ?
C25 C26 C27 C21 176.2(7) . . . . ?
O7 C21 C27 C22 -3.2(13) . . . . ?
C20 C21 C27 C22 175.1(8) . . . . ?
O7 C21 C27 C26 -179.9(8) . . . . ?
C20 C21 C27 C26 -1.5(12) . . . . ?
C19 C20 C28 O5 -2.1(14) . . . . ?
C21 C20 C28 O5 -178.7(9) . . . . ?
C19 C20 C28 O6 178.9(9) . . . . ?
C21 C20 C28 O6 2.3(12) . . . . ?
C25 O8 C29 C30 -51.7(10) . . . . ?
C19 N4 C30 C29 145.2(9) . . . . ?
C26 N4 C30 C29 -42.2(11) . . . . ?
C19 N4 C30 C31 21.8(12) . . . . ?
C26 N4 C30 C31 -165.7(8) . . . . ?
O8 C29 C30 N4 62.2(10) . . . . ?
O8 C29 C30 C31 -174.9(8) . . . . ?
C24 N5 C32 C33 -118.0(11) . . . . ?
C35 N5 C32 C33 52.2(14) . . . . ?
C36 N6 C33 C32 -177.9(9) . . . . ?
C34 N6 C33 C32 60.8(10) . . . . ?
N5 C32 C33 N6 -55.6(13) . . . . ?
C33 N6 C34 C35 -62.1(13) . . . . ?
C36 N6 C34 C35 176.8(12) . . . . ?
C24 N5 C35 C34 118.6(10) . . . . ?
C32 N5 C35 C34 -51.9(12) . . . . ?
N6 C34 C35 N5 55.9(14) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.76 2.524(14) 155.1 . yes
O6 H6 O7 0.82 1.77 2.535(15) 154.5 . yes
O10 H10A N6 0.82 2.04 2.838(14) 165.4 3_445 yes
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062
_cell_measurement_pressure       2.19




# start Validation Reply Form
_vrf_ATOM007_LH_PE_2p19          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_PE_2p19          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_PE_2p19          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_PE_2p19          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_PE_2p19          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_PE_2p19          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_PE_2p19          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_PE_2p19          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_PE_2p19          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_2p19          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT111_LH_PE_2p19          
;
RESPONSE: The structure is chiral.

;
_vrf_PLAT721_LH_PE_2p19          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints

;
_vrf_PLAT910_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_PE_2p19          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_PE_2p19          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_PE_2p19          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_PE_2p19          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_OFLO_3p62
_database_code_depnum_ccdc_archive 'CCDC 2481346'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_260522_run1_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   28.697(7)
_cell_length_b                   6.1346(5)
_cell_length_c                   15.9813(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.278(15)
_cell_angle_gamma                90
_cell_volume                     2738.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4764
_cell_measurement_theta_min      2.619
_cell_measurement_theta_max      23.266
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6464
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            4764
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.619
_diffrn_reflns_theta_max         23.266
_diffrn_reflns_theta_full        23.266
_diffrn_measured_fraction_theta_max 0.348
_diffrn_measured_fraction_theta_full 0.348
_diffrn_reflns_Laue_measured_fraction_max 0.348
_diffrn_reflns_Laue_measured_fraction_full 0.348
_diffrn_reflns_point_group_measured_fraction_max 0.348
_diffrn_reflns_point_group_measured_fraction_full 0.348
_reflns_number_total             686
_reflns_number_gt                483
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+4.3269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         686
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      0.912
_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
F1 F 0.5703(3) 0.7019(5) 0.78986(19) 0.028(5) Uani 1 1 d D . . . .
O1 O 0.6490(4) 0.5899(6) 0.5663(3) 0.034(5) Uani 1 1 d D . . . .
O4 O 0.4348(4) 0.8118(5) 0.2676(2) 0.021(6) Uani 1 1 d D . . . .
C11 C 0.5237(5) 0.7283(9) 0.5606(4) 0.026(4) Uani 1 1 d D . . . .
O2 O 0.4419(4) 0.8239(6) 0.5255(3) 0.030(5) Uani 1 1 d D . . . .
N3 N 0.5635(5) 0.6850(8) 0.4449(3) 0.026(4) Uani 1 1 d D . . . .
N1 N 0.6509(5) 0.6056(7) 0.7445(3) 0.030(4) Uani 1 1 d D . . . .
C7 C 0.5673(6) 0.6914(9) 0.7025(4) 0.023(4) Uani 1 1 d D . . . .
C10 C 0.5653(5) 0.6792(9) 0.5327(4) 0.026(4) Uani 1 1 d D . . . .
C3 C 0.5227(6) 0.7305(10) 0.3891(5) 0.023(5) Uani 1 1 d D . . . .
H3 H 0.522819 0.733305 0.330945 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6098(6) 0.6375(9) 0.6797(4) 0.026(4) Uani 1 1 d D . . . .
O3 O 0.3991(4) 0.8721(6) 0.3737(3) 0.031(5) Uani 1 1 d D . . . .
H3A H 0.406110 0.872503 0.426403 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4807(6) 0.7730(9) 0.4116(4) 0.023(4) Uani 1 1 d D . . . .
C6 C 0.5246(6) 0.7354(9) 0.6488(4) 0.028(5) Uani 1 1 d D . . . .
H6 H 0.497548 0.768361 0.668948 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6074(5) 0.6331(10) 0.5911(4) 0.026(4) Uani 1 1 d D . . . .
N2 N 0.7468(4) 0.5962(7) 0.8417(3) 0.031(5) Uani 1 1 d D . . . .
C13 C 0.4369(6) 0.8195(9) 0.3449(4) 0.026(5) Uani 1 1 d D . . . .
C16 C 0.7154(5) 0.7778(9) 0.8508(3) 0.032(6) Uani 1 1 d D . . . .
H16A H 0.734293 0.909766 0.864046 0.038 Uiso 1 1 calc R U . . .
H16B H 0.700419 0.748805 0.898271 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4782(5) 0.7756(9) 0.4998(4) 0.023(4) Uani 1 1 d D . . . .
C1 C 0.6440(5) 0.5203(8) 0.4785(3) 0.034(6) Uani 1 1 d D . . . .
H1A H 0.631063 0.373582 0.471283 0.041 Uiso 1 1 calc R U . . .
H1B H 0.675023 0.519528 0.464101 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6313(6) 0.9007(8) 0.4203(4) 0.029(7) Uani 1 1 d D . . . .
H12A H 0.609811 0.992417 0.380459 0.043 Uiso 1 1 calc R U . . .
H12B H 0.661448 0.892414 0.404055 0.043 Uiso 1 1 calc R U . . .
H12C H 0.636100 0.960676 0.477110 0.043 Uiso 1 1 calc R U . . .
C2 C 0.6103(6) 0.6770(9) 0.4191(4) 0.028(5) Uani 1 1 d D . . . .
H2 H 0.604625 0.620432 0.360268 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6773(5) 0.8116(8) 0.7700(3) 0.029(5) Uani 1 1 d D . . . .
H17A H 0.655225 0.923651 0.779412 0.035 Uiso 1 1 calc R U . . .
H17B H 0.691921 0.860009 0.724163 0.035 Uiso 1 1 calc R U . . .
C15 C 0.7195(5) 0.3962(8) 0.8176(3) 0.030(5) Uani 1 1 d D . . . .
H15A H 0.703310 0.356397 0.862354 0.036 Uiso 1 1 calc R U . . .
H15B H 0.741129 0.278631 0.811619 0.036 Uiso 1 1 calc R U . . .
C18 C 0.7834(5) 0.5641(10) 0.9211(3) 0.039(6) Uani 1 1 d D . . . .
H18A H 0.801919 0.694978 0.934575 0.059 Uiso 1 1 calc R U . . .
H18B H 0.803992 0.446076 0.913505 0.059 Uiso 1 1 calc R U . . .
H18C H 0.768252 0.530203 0.967164 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6833(5) 0.4272(9) 0.7343(3) 0.035(5) Uani 1 1 d D . . . .
H14A H 0.699430 0.462305 0.688839 0.042 Uiso 1 1 calc R U . . .
H14B H 0.665237 0.293931 0.718731 0.042 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 C7 1.380(6) . ?
O1 C9 1.369(14) . ?
O1 C1 1.442(6) . ?
O4 C13 1.223(7) . ?
C11 C10 1.399(13) . ?
C11 C6 1.405(7) . ?
C11 C5 1.467(11) . ?
O2 C5 1.241(13) . ?
N3 C3 1.328(15) . ?
N3 C10 1.393(7) . ?
N3 C2 1.493(16) . ?
N1 C8 1.393(15) . ?
N1 C14 1.469(11) . ?
N1 C17 1.482(10) . ?
C7 C6 1.350(16) . ?
C7 C8 1.391(18) . ?
C10 C9 1.374(15) . ?
C3 C4 1.358(17) . ?
C3 H3 0.9300 . ?
C8 C9 1.402(8) . ?
O3 C13 1.314(15) . ?
O3 H3A 0.8200 . ?
C4 C5 1.428(9) . ?
C4 C13 1.477(14) . ?
C6 H6 0.9300 . ?
N2 C15 1.459(10) . ?
N2 C16 1.461(11) . ?
N2 C18 1.462(9) . ?
C16 C17 1.503(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.529(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.497(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.501(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 116.2(10) . . ?
C10 C11 C6 120.3(10) . . ?
C10 C11 C5 121.8(6) . . ?
C6 C11 C5 117.8(10) . . ?
C3 N3 C10 120.3(11) . . ?
C3 N3 C2 122.1(6) . . ?
C10 N3 C2 116.7(11) . . ?
C8 N1 C14 118.2(6) . . ?
C8 N1 C17 112.2(6) . . ?
C14 N1 C17 111.6(9) . . ?
C6 C7 F1 118.1(10) . . ?
C6 C7 C8 127.0(7) . . ?
F1 C7 C8 114.9(11) . . ?
C9 C10 N3 120.9(11) . . ?
C9 C10 C11 120.5(6) . . ?
N3 C10 C11 118.5(11) . . ?
N3 C3 C4 124.1(7) . . ?
N3 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
C7 C8 N1 118.9(6) . . ?
C7 C8 C9 115.2(12) . . ?
N1 C8 C9 125.8(12) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.9(12) . . ?
C3 C4 C13 120.3(7) . . ?
C5 C4 C13 118.8(12) . . ?
C7 C6 C11 116.0(11) . . ?
C7 C6 H6 122.0 . . ?
C11 C6 H6 122.0 . . ?
O1 C9 C10 122.1(6) . . ?
O1 C9 C8 116.9(11) . . ?
C10 C9 C8 120.9(11) . . ?
C15 N2 C16 111.3(9) . . ?
C15 N2 C18 110.6(5) . . ?
C16 N2 C18 110.7(5) . . ?
O4 C13 O3 120.6(12) . . ?
O4 C13 C4 123.9(11) . . ?
O3 C13 C4 115.4(7) . . ?
N2 C16 C17 111.3(5) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O2 C5 C4 124.5(12) . . ?
O2 C5 C11 121.1(6) . . ?
C4 C5 C11 114.3(11) . . ?
O1 C1 C2 109.0(6) . . ?
O1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C12 110.6(8) . . ?
N3 C2 C1 109.3(7) . . ?
C12 C2 C1 111.9(11) . . ?
N3 C2 H2 108.3 . . ?
C12 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
N1 C17 C16 110.1(5) . . ?
N1 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
N2 C15 C14 110.4(5) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 108.8(5) . . ?
N1 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
N1 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 C10 C9 -179.8(7) . . . . ?
C2 N3 C10 C9 -10.1(9) . . . . ?
C3 N3 C10 C11 -1.8(10) . . . . ?
C2 N3 C10 C11 167.8(5) . . . . ?
C6 C11 C10 C9 1.3(10) . . . . ?
C5 C11 C10 C9 -179.3(7) . . . . ?
C6 C11 C10 N3 -176.7(6) . . . . ?
C5 C11 C10 N3 2.8(9) . . . . ?
C10 N3 C3 C4 -0.2(12) . . . . ?
C2 N3 C3 C4 -169.3(6) . . . . ?
C6 C7 C8 N1 177.5(7) . . . . ?
F1 C7 C8 N1 -1.8(9) . . . . ?
C6 C7 C8 C9 1.2(11) . . . . ?
F1 C7 C8 C9 -178.1(5) . . . . ?
C14 N1 C8 C7 140.3(7) . . . . ?
C17 N1 C8 C7 -87.7(8) . . . . ?
C14 N1 C8 C9 -43.8(10) . . . . ?
C17 N1 C8 C9 88.2(8) . . . . ?
N3 C3 C4 C5 1.2(12) . . . . ?
N3 C3 C4 C13 -179.3(7) . . . . ?
F1 C7 C6 C11 178.4(5) . . . . ?
C8 C7 C6 C11 -0.9(11) . . . . ?
C10 C11 C6 C7 -0.4(10) . . . . ?
C5 C11 C6 C7 -179.8(6) . . . . ?
C1 O1 C9 C10 -20.9(9) . . . . ?
C1 O1 C9 C8 161.6(5) . . . . ?
N3 C10 C9 O1 -0.4(11) . . . . ?
C11 C10 C9 O1 -178.3(6) . . . . ?
N3 C10 C9 C8 176.9(6) . . . . ?
C11 C10 C9 C8 -1.0(10) . . . . ?
C7 C8 C9 O1 177.3(6) . . . . ?
N1 C8 C9 O1 1.2(10) . . . . ?
C7 C8 C9 C10 -0.2(10) . . . . ?
N1 C8 C9 C10 -176.2(6) . . . . ?
C3 C4 C13 O4 3.9(10) . . . . ?
C5 C4 C13 O4 -176.6(6) . . . . ?
C3 C4 C13 O3 -175.8(7) . . . . ?
C5 C4 C13 O3 3.6(9) . . . . ?
C15 N2 C16 C17 -56.2(7) . . . . ?
C18 N2 C16 C17 -179.5(6) . . . . ?
C3 C4 C5 O2 176.2(7) . . . . ?
C13 C4 C5 O2 -3.3(11) . . . . ?
C3 C4 C5 C11 -0.3(10) . . . . ?
C13 C4 C5 C11 -179.7(5) . . . . ?
C10 C11 C5 O2 -178.3(7) . . . . ?
C6 C11 C5 O2 1.2(9) . . . . ?
C10 C11 C5 C4 -1.7(9) . . . . ?
C6 C11 C5 C4 177.8(6) . . . . ?
C9 O1 C1 C2 49.2(10) . . . . ?
C3 N3 C2 C12 84.2(9) . . . . ?
C10 N3 C2 C12 -85.3(8) . . . . ?
C3 N3 C2 C1 -152.2(6) . . . . ?
C10 N3 C2 C1 38.3(7) . . . . ?
O1 C1 C2 N3 -56.7(10) . . . . ?
O1 C1 C2 C12 66.1(12) . . . . ?
C8 N1 C17 C16 168.8(7) . . . . ?
C14 N1 C17 C16 -56.0(7) . . . . ?
N2 C16 C17 N1 54.0(9) . . . . ?
C16 N2 C15 C14 58.9(7) . . . . ?
C18 N2 C15 C14 -177.7(6) . . . . ?
C8 N1 C14 C15 -169.3(8) . . . . ?
C17 N1 C14 C15 58.4(7) . . . . ?
N2 C15 C14 N1 -59.3(9) . . . . ?
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_cell_measurement_pressure       3.62

# start Validation Reply Form
_vrf_ATOM007_OFLO_3p62           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_3p62           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_3p62           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_3p62           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_3p62           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_3p62           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_3p62           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_3p62           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_3p62           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_3p62           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_3p62           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_3p62           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_3p62           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_LH_PE_4p05
_database_code_depnum_ccdc_archive 'CCDC 2481336'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_Levo_HH_20241031_08

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.25(H4 O2)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   27.562(3)
_cell_length_b                   6.1945(7)
_cell_length_c                   17.830(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.823(9)
_cell_angle_gamma                90
_cell_volume                     2784.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13522
_cell_measurement_theta_min      1.593
_cell_measurement_theta_max      24.845
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.997
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon III'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13522
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.593
_diffrn_reflns_theta_max         24.845
_diffrn_reflns_theta_full        24.845
_diffrn_measured_fraction_theta_max 0.620
_diffrn_measured_fraction_theta_full 0.620
_diffrn_reflns_Laue_measured_fraction_max 0.620
_diffrn_reflns_Laue_measured_fraction_full 0.620
_diffrn_reflns_point_group_measured_fraction_max 0.605
_diffrn_reflns_point_group_measured_fraction_full 0.605
_reflns_number_total             2926
_reflns_number_gt                1973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     0.586
_reflns_Friedel_fraction_full    0.586
_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_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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_abs_structure_details 
;
 Flack x determined using 637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2926
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.1501
_refine_ls_R_factor_gt           0.1074
_refine_ls_wR_factor_ref         0.3265
_refine_ls_wR_factor_gt          0.2935
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      2.914
_refine_ls_shift/su_max          0.395
_refine_ls_shift/su_mean         0.017
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 0.2096(2) 0.4360(11) 0.7240(7) 0.0345(19) Uiso 1 1 d D U . . .
O1 O 0.3227(3) 0.4562(15) 1.2354(9) 0.040(3) Uiso 1 1 d D U . . .
O2 O 0.3782(3) 0.4482(15) 1.1726(8) 0.034(2) Uiso 1 1 d D U . . .
H2 H 0.375764 0.459117 1.125432 0.050 Uiso 1 1 calc R U . . .
O3 O 0.3391(3) 0.4677(13) 1.0172(8) 0.029(2) Uiso 1 1 d D U . . .
O4 O 0.1011(3) 0.4267(14) 0.8693(7) 0.032(2) Uiso 1 1 d D U . . .
N1 N 0.1914(3) 0.4507(15) 1.0180(8) 0.024(2) Uiso 1 1 d D U . . .
N2 N 0.1099(3) 0.4490(15) 0.7182(7) 0.026(2) Uiso 1 1 d D U . . .
N3 N 0.0105(3) 0.6391(14) 0.6216(8) 0.025(2) Uiso 1 1 d D U . . .
C1 C 0.2348(4) 0.4521(19) 1.0878(9) 0.029(3) Uiso 1 1 d D U . . .
H1 H 0.230547 0.448083 1.136976 0.035 Uiso 1 1 calc R U . . .
C2 C 0.2858(4) 0.459(2) 1.0912(8) 0.027(3) Uiso 1 1 d D U . . .
C3 C 0.2936(3) 0.4594(17) 1.0172(8) 0.017(3) Uiso 1 1 d D U . . .
C4 C 0.2498(4) 0.4521(19) 0.8653(9) 0.028(3) Uiso 1 1 d D U . . .
H4 H 0.282846 0.452746 0.862750 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2051(3) 0.4473(18) 0.7956(8) 0.022(3) Uiso 1 1 d D U . . .
C6 C 0.1535(3) 0.4470(18) 0.7938(8) 0.018(3) Uiso 1 1 d D U . . .
C7 C 0.1506(3) 0.4422(18) 0.8692(8) 0.018(3) Uiso 1 1 d D U . . .
C8 C 0.1957(3) 0.4479(18) 0.9438(8) 0.020(3) Uiso 1 1 d D U . . .
C9 C 0.2460(3) 0.4561(18) 0.9415(9) 0.021(3) Uiso 1 1 d D U . . .
C10 C 0.3295(3) 0.4565(19) 1.1729(9) 0.025(3) Uiso 1 1 d D U . . .
C11 C 0.0979(4) 0.524(2) 0.9391(8) 0.033(3) Uiso 1 1 d D U . . .
H11A H 0.062596 0.501685 0.937263 0.040 Uiso 1 1 calc R U . . .
H11B H 0.103398 0.678293 0.937474 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1380(3) 0.434(2) 1.0182(8) 0.030(3) Uiso 1 1 d D U . . .
H12 H 0.129869 0.282622 1.023410 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1335(5) 0.563(2) 1.0871(10) 0.036(3) Uiso 1 1 d D U . . .
H13A H 0.152039 0.490017 1.138164 0.053 Uiso 1 1 calc R U . . .
H13B H 0.096781 0.578272 1.077497 0.053 Uiso 1 1 calc R U . . .
H13C H 0.148756 0.703792 1.089283 0.053 Uiso 1 1 calc R U . . .
C14 C 0.0602(3) 0.3418(18) 0.7055(12) 0.029(3) Uiso 1 1 d D U . . .
H14A H 0.064878 0.254511 0.753083 0.035 Uiso 1 1 calc R U . . .
H14B H 0.050121 0.247048 0.658325 0.035 Uiso 1 1 calc R U . . .
C15 C 0.0173(4) 0.5051(19) 0.6918(9) 0.032(3) Uiso 1 1 d D U . . .
H15A H -0.015746 0.431624 0.682448 0.038 Uiso 1 1 calc R U . . .
H15B H 0.026468 0.594847 0.740171 0.038 Uiso 1 1 calc R U . . .
C16 C 0.0598(4) 0.7554(18) 0.6371(12) 0.030(3) Uiso 1 1 d D U . . .
H16A H 0.067830 0.849858 0.683986 0.036 Uiso 1 1 calc R U . . .
H16B H 0.055312 0.844127 0.589942 0.036 Uiso 1 1 calc R U . . .
C17 C 0.1050(4) 0.6011(19) 0.6535(10) 0.035(3) Uiso 1 1 d D U . . .
H17A H 0.099444 0.522197 0.603645 0.042 Uiso 1 1 calc R U . . .
H17B H 0.137779 0.682032 0.669076 0.042 Uiso 1 1 calc R U . . .
C18 C -0.0322(4) 0.7960(19) 0.6043(14) 0.036(3) Uiso 1 1 d D U . . .
H18A H -0.063412 0.723875 0.602821 0.055 Uiso 1 1 calc R U . . .
H18B H -0.039745 0.863103 0.552245 0.055 Uiso 1 1 calc R U . . .
H18C H -0.021549 0.904081 0.646468 0.055 Uiso 1 1 calc R U . . .
F2 F 0.2848(2) 0.7408(11) 0.7659(7) 0.035(2) Uiso 1 1 d D U . . .
O5 O 0.1856(4) 0.7144(15) 0.2586(9) 0.046(3) Uiso 1 1 d D U . . .
O6 O 0.1283(3) 0.7304(15) 0.3188(8) 0.035(2) Uiso 1 1 d D U . . .
H6 H 0.130960 0.730858 0.366357 0.053 Uiso 1 1 calc R U . . .
O7 O 0.1606(3) 0.6836(13) 0.4701(8) 0.027(2) Uiso 1 1 d D U . . .
O8 O 0.3988(3) 0.7174(14) 0.6282(9) 0.037(3) Uiso 1 1 d D U . . .
N4 N 0.3112(3) 0.6659(15) 0.4794(8) 0.026(3) Uiso 1 1 d D U . . .
N5 N 0.3845(3) 0.7357(17) 0.7738(8) 0.033(3) Uiso 1 1 d D U . . .
N6 N 0.4857(3) 0.5830(15) 0.8819(8) 0.031(3) Uiso 1 1 d D U . . .
C19 C 0.2697(4) 0.6720(18) 0.4072(9) 0.028(3) Uiso 1 1 d D U . . .
H19 H 0.275278 0.661334 0.359285 0.034 Uiso 1 1 calc R U . . .
C20 C 0.2188(3) 0.6938(18) 0.4020(8) 0.023(3) Uiso 1 1 d D U . . .
C21 C 0.2072(3) 0.6827(18) 0.4724(8) 0.023(3) Uiso 1 1 d D U . . .
C22 C 0.2463(4) 0.7002(18) 0.6243(9) 0.024(3) Uiso 1 1 d D U . . .
H22 H 0.212784 0.696589 0.625003 0.028 Uiso 1 1 calc R U . . .
C23 C 0.2901(4) 0.7174(18) 0.6943(8) 0.024(3) Uiso 1 1 d D U . . .
C24 C 0.3427(4) 0.7197(19) 0.6994(8) 0.026(3) Uiso 1 1 d D U . . .
C25 C 0.3487(3) 0.7095(18) 0.6250(8) 0.024(3) Uiso 1 1 d D U . . .
C26 C 0.3041(4) 0.6934(18) 0.5516(8) 0.025(3) Uiso 1 1 d D U . . .
C27 C 0.2525(3) 0.6881(17) 0.5512(9) 0.023(3) Uiso 1 1 d D U . . .
C28 C 0.1759(4) 0.716(2) 0.3182(9) 0.030(3) Uiso 1 1 d D U . . .
C29 C 0.4026(4) 0.757(2) 0.5513(9) 0.035(3) Uiso 1 1 d D U . . .
H29A H 0.438633 0.731491 0.556955 0.042 Uiso 1 1 calc R U . . .
H29B H 0.393569 0.906025 0.535006 0.042 Uiso 1 1 calc R U . . .
C30 C 0.3652(4) 0.609(2) 0.4874(10) 0.032(3) Uiso 1 1 d D U . . .
H30 H 0.372772 0.459844 0.507201 0.039 Uiso 1 1 calc R U . . .
C31 C 0.3722(5) 0.627(3) 0.4085(12) 0.050(4) Uiso 1 1 d D U . . .
H31A H 0.348611 0.528163 0.369052 0.076 Uiso 1 1 calc R U . . .
H31B H 0.408146 0.592902 0.417930 0.076 Uiso 1 1 calc R U . . .
H31C H 0.364198 0.771763 0.387848 0.076 Uiso 1 1 calc R U . . .
C32 C 0.4333(3) 0.8572(17) 0.7917(11) 0.027(3) Uiso 1 1 d D U . . .
H32A H 0.439449 0.952019 0.837962 0.032 Uiso 1 1 calc R U . . .
H32B H 0.429098 0.946444 0.744800 0.032 Uiso 1 1 calc R U . . .
C33 C 0.4806(4) 0.7127(18) 0.8111(9) 0.030(3) Uiso 1 1 d D U . . .
H33A H 0.475646 0.620175 0.764652 0.036 Uiso 1 1 calc R U . . .
H33B H 0.512333 0.798386 0.823254 0.036 Uiso 1 1 calc R U . . .
C34 C 0.4387(4) 0.4511(19) 0.8619(12) 0.034(3) Uiso 1 1 d D U . . .
H34A H 0.442645 0.361152 0.908541 0.041 Uiso 1 1 calc R U . . .
H34B H 0.434695 0.357102 0.816274 0.041 Uiso 1 1 calc R U . . .
C35 C 0.3900(4) 0.5883(18) 0.8396(10) 0.029(3) Uiso 1 1 d D U . . .
H35A H 0.358931 0.496202 0.822851 0.035 Uiso 1 1 calc R U . . .
H35B H 0.392099 0.669814 0.887274 0.035 Uiso 1 1 calc R U . . .
C36 C 0.5328(4) 0.447(2) 0.9055(16) 0.045(4) Uiso 1 1 d D U . . .
H36A H 0.532115 0.370531 0.858316 0.067 Uiso 1 1 calc R U . . .
H36B H 0.533307 0.346034 0.946556 0.067 Uiso 1 1 calc R U . . .
H36C H 0.563952 0.536172 0.927104 0.067 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.335(2) 0.500000 0.044(4) Uiso 1 2 d DGS . P . .
H9A H 0.000803 0.430183 0.469994 0.065 Uiso 0.5 1 d DG U P . .
H9B H 0.006781 0.228220 0.479917 0.065 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.400(2) 1.000000 0.040(4) Uiso 1 2 d DGS . P . .
H10A H 0.003709 0.448345 0.961501 0.061 Uiso 0.5 1 d DG U P . .
H10B H -0.025597 0.325320 0.979028 0.061 Uiso 0.5 1 d DG U P . .
_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 C5 1.333(11) . ?
O1 C10 1.201(11) . ?
O2 C10 1.345(10) . ?
O2 H2 0.8200 . ?
O3 C3 1.257(10) . ?
O4 C7 1.369(10) . ?
O4 C11 1.416(12) . ?
N1 C1 1.333(11) . ?
N1 C8 1.376(11) . ?
N1 C12 1.476(10) . ?
N2 C6 1.397(11) . ?
N2 C14 1.453(10) . ?
N2 C17 1.455(12) . ?
N3 C15 1.450(12) . ?
N3 C18 1.460(10) . ?
N3 C16 1.461(10) . ?
C1 C2 1.383(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.420(11) . ?
C2 C10 1.468(12) . ?
C3 C9 1.452(11) . ?
C4 C5 1.351(11) . ?
C4 C9 1.405(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(10) . ?
C6 C7 1.379(11) . ?
C7 C8 1.406(11) . ?
C8 C9 1.405(11) . ?
C11 C12 1.504(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.512(13) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.500(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.503(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.350(11) . ?
O5 C28 1.197(12) . ?
O6 C28 1.320(11) . ?
O6 H6 0.8200 . ?
O7 C21 1.267(10) . ?
O8 C25 1.360(10) . ?
O8 C29 1.437(12) . ?
N4 C19 1.332(11) . ?
N4 C26 1.389(11) . ?
N4 C30 1.480(10) . ?
N5 C24 1.365(11) . ?
N5 C35 1.445(12) . ?
N5 C32 1.459(10) . ?
N6 C34 1.449(10) . ?
N6 C33 1.455(12) . ?
N6 C36 1.459(11) . ?
C19 C20 1.375(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.415(12) . ?
C20 C28 1.491(12) . ?
C21 C27 1.456(11) . ?
C22 C23 1.345(11) . ?
C22 C27 1.384(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.416(11) . ?
C24 C25 1.401(12) . ?
C25 C26 1.391(11) . ?
C26 C27 1.419(11) . ?
C29 C30 1.502(11) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.499(13) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.502(10) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.500(10) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8019 . ?
O9 H9B 0.8097 . ?
O9 H9A 0.8(3) 2_556 ?
O9 H9B 0.8(3) 2_556 ?
O10 H10A 0.7922 . ?
O10 H10B 0.7993 . ?
O10 H10A 0.8(2) 2_557 ?
O10 H10B 0.8(3) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 112.8(9) . . ?
C1 N1 C8 120.4(9) . . ?
C1 N1 C12 121.2(11) . . ?
C8 N1 C12 118.3(9) . . ?
C6 N2 C14 122.4(11) . . ?
C6 N2 C17 122.6(9) . . ?
C14 N2 C17 113.1(9) . . ?
C15 N3 C18 112.0(12) . . ?
C15 N3 C16 109.5(10) . . ?
C18 N3 C16 108.7(8) . . ?
N1 C1 C2 123.6(13) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 119.5(10) . . ?
C1 C2 C10 117.0(11) . . ?
C3 C2 C10 123.4(9) . . ?
O3 C3 C2 121.8(10) . . ?
O3 C3 C9 121.8(12) . . ?
C2 C3 C9 116.4(9) . . ?
C5 C4 C9 119.6(11) . . ?
C5 C4 H4 120.2 . . ?
C9 C4 H4 120.2 . . ?
F1 C5 C4 118.6(10) . . ?
F1 C5 C6 117.5(9) . . ?
C4 C5 C6 123.9(12) . . ?
C7 C6 N2 125.1(9) . . ?
C7 C6 C5 115.7(9) . . ?
N2 C6 C5 119.3(11) . . ?
O4 C7 C6 116.9(9) . . ?
O4 C7 C8 120.1(11) . . ?
C6 C7 C8 122.9(9) . . ?
N1 C8 C9 119.7(9) . . ?
N1 C8 C7 121.5(9) . . ?
C9 C8 C7 118.7(11) . . ?
C8 C9 C4 119.1(10) . . ?
C8 C9 C3 120.3(11) . . ?
C4 C9 C3 120.5(9) . . ?
O1 C10 O2 122.1(11) . . ?
O1 C10 C2 123.2(10) . . ?
O2 C10 C2 114.6(11) . . ?
O4 C11 C12 112.6(10) . . ?
O4 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
O4 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 C11 109.2(10) . . ?
N1 C12 C13 112.0(10) . . ?
C11 C12 C13 107.2(10) . . ?
N1 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C13 C12 H12 109.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 110.4(9) . . ?
N2 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N2 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C14 110.2(12) . . ?
N3 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N3 C15 H15B 109.6 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 111.0(9) . . ?
N3 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N3 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N2 C17 C16 111.6(11) . . ?
N2 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.4 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 115.5(10) . . ?
C19 N4 C26 120.3(10) . . ?
C19 N4 C30 122.5(12) . . ?
C26 N4 C30 116.9(10) . . ?
C24 N5 C35 121.0(10) . . ?
C24 N5 C32 126.2(11) . . ?
C35 N5 C32 111.3(10) . . ?
C34 N6 C33 109.5(11) . . ?
C34 N6 C36 110.5(9) . . ?
C33 N6 C36 109.3(13) . . ?
N4 C19 C20 121.5(13) . . ?
N4 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 121.7(10) . . ?
C19 C20 C28 116.8(11) . . ?
C21 C20 C28 121.4(9) . . ?
O7 C21 C20 124.0(10) . . ?
O7 C21 C27 119.7(11) . . ?
C20 C21 C27 116.1(9) . . ?
C23 C22 C27 118.2(11) . . ?
C23 C22 H22 120.9 . . ?
C27 C22 H22 120.9 . . ?
C22 C23 F2 119.1(10) . . ?
C22 C23 C24 124.8(12) . . ?
F2 C23 C24 116.0(10) . . ?
N5 C24 C25 123.3(10) . . ?
N5 C24 C23 120.1(12) . . ?
C25 C24 C23 116.6(10) . . ?
O8 C25 C26 122.5(12) . . ?
O8 C25 C24 117.7(10) . . ?
C26 C25 C24 119.8(10) . . ?
N4 C26 C25 118.7(10) . . ?
N4 C26 C27 120.5(10) . . ?
C25 C26 C27 120.6(11) . . ?
C22 C27 C26 119.9(10) . . ?
C22 C27 C21 121.7(9) . . ?
C26 C27 C21 118.3(11) . . ?
O5 C28 O6 126.0(12) . . ?
O5 C28 C20 121.2(10) . . ?
O6 C28 C20 112.7(11) . . ?
O8 C29 C30 109.1(12) . . ?
O8 C29 H29A 109.8 . . ?
C30 C29 H29A 109.9 . . ?
O8 C29 H29B 109.8 . . ?
C30 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
N4 C30 C31 113.4(12) . . ?
N4 C30 C29 106.4(10) . . ?
C31 C30 C29 110.9(12) . . ?
N4 C30 H30 108.7 . . ?
C31 C30 H30 108.7 . . ?
C29 C30 H30 108.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 112.4(9) . . ?
N5 C32 H32A 109.2 . . ?
C33 C32 H32A 109.1 . . ?
N5 C32 H32B 109.1 . . ?
C33 C32 H32B 109.1 . . ?
H32A C32 H32B 107.9 . . ?
N6 C33 C32 107.4(11) . . ?
N6 C33 H33A 110.2 . . ?
C32 C33 H33A 110.2 . . ?
N6 C33 H33B 110.2 . . ?
C32 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
N6 C34 C35 111.2(9) . . ?
N6 C34 H34A 109.4 . . ?
C35 C34 H34A 109.4 . . ?
N6 C34 H34B 109.4 . . ?
C35 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
N5 C35 C34 111.3(12) . . ?
N5 C35 H35A 109.4 . . ?
C34 C35 H35A 109.4 . . ?
N5 C35 H35B 109.4 . . ?
C34 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
N6 C36 H36A 109.4 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 103.4 . . ?
H9A O9 H9A 85.5 . 2_556 ?
H9B O9 H9A 165.7 . 2_556 ?
H9A O9 H9B 165.7 . 2_556 ?
H9B O9 H9B 70.3 . 2_556 ?
H9A O9 H9B 103.4 2_556 2_556 ?
H10A O10 H10B 102.2 . . ?
H10A O10 H10A 135.7 . 2_557 ?
H10B O10 H10A 103.0 . 2_557 ?
H10A O10 H10B 103.0 . 2_557 ?
H10B O10 H10B 109.2 . 2_557 ?
H10A O10 H10B 102.2 2_557 2_557 ?
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
C8 N1 C1 C2 2.6(18) . . . . ?
C12 N1 C1 C2 177.6(11) . . . . ?
N1 C1 C2 C3 -1.7(19) . . . . ?
N1 C1 C2 C10 -179.1(10) . . . . ?
C1 C2 C3 O3 179.3(11) . . . . ?
C10 C2 C3 O3 -3.4(18) . . . . ?
C1 C2 C3 C9 1.1(17) . . . . ?
C10 C2 C3 C9 178.3(10) . . . . ?
C9 C4 C5 F1 -177.7(10) . . . . ?
C9 C4 C5 C6 0.3(18) . . . . ?
C14 N2 C6 C7 -31.9(18) . . . . ?
C17 N2 C6 C7 131.4(13) . . . . ?
C14 N2 C6 C5 147.2(11) . . . . ?
C17 N2 C6 C5 -49.4(17) . . . . ?
F1 C5 C6 C7 175.2(10) . . . . ?
C4 C5 C6 C7 -2.8(17) . . . . ?
F1 C5 C6 N2 -4.1(16) . . . . ?
C4 C5 C6 N2 177.9(11) . . . . ?
C11 O4 C7 C6 -151.2(11) . . . . ?
C11 O4 C7 C8 30.1(15) . . . . ?
N2 C6 C7 O4 3.6(18) . . . . ?
C5 C6 C7 O4 -175.6(10) . . . . ?
N2 C6 C7 C8 -177.8(10) . . . . ?
C5 C6 C7 C8 3.0(17) . . . . ?
C1 N1 C8 C9 -2.8(17) . . . . ?
C12 N1 C8 C9 -178.0(10) . . . . ?
C1 N1 C8 C7 178.8(10) . . . . ?
C12 N1 C8 C7 3.6(16) . . . . ?
O4 C7 C8 N1 -3.8(17) . . . . ?
C6 C7 C8 N1 177.6(10) . . . . ?
O4 C7 C8 C9 177.8(10) . . . . ?
C6 C7 C8 C9 -0.8(17) . . . . ?
N1 C8 C9 C4 179.7(10) . . . . ?
C7 C8 C9 C4 -1.8(16) . . . . ?
N1 C8 C9 C3 2.3(16) . . . . ?
C7 C8 C9 C3 -179.2(10) . . . . ?
C5 C4 C9 C8 2.1(17) . . . . ?
C5 C4 C9 C3 179.5(10) . . . . ?
O3 C3 C9 C8 -179.7(11) . . . . ?
C2 C3 C9 C8 -1.4(15) . . . . ?
O3 C3 C9 C4 2.9(17) . . . . ?
C2 C3 C9 C4 -178.8(10) . . . . ?
C1 C2 C10 O1 -2.7(18) . . . . ?
C3 C2 C10 O1 180.0(12) . . . . ?
C1 C2 C10 O2 175.5(11) . . . . ?
C3 C2 C10 O2 -1.8(17) . . . . ?
C7 O4 C11 C12 -55.9(14) . . . . ?
C1 N1 C12 C11 157.4(10) . . . . ?
C8 N1 C12 C11 -27.5(15) . . . . ?
C1 N1 C12 C13 38.8(16) . . . . ?
C8 N1 C12 C13 -146.1(11) . . . . ?
O4 C11 C12 N1 53.8(14) . . . . ?
O4 C11 C12 C13 175.4(10) . . . . ?
C6 N2 C14 C15 111.6(14) . . . . ?
C17 N2 C14 C15 -53.2(17) . . . . ?
C18 N3 C15 C14 178.1(10) . . . . ?
C16 N3 C15 C14 -61.3(13) . . . . ?
N2 C14 C15 N3 58.3(16) . . . . ?
C15 N3 C16 C17 58.7(17) . . . . ?
C18 N3 C16 C17 -178.7(15) . . . . ?
C6 N2 C17 C16 -113.9(13) . . . . ?
C14 N2 C17 C16 50.8(15) . . . . ?
N3 C16 C17 N2 -53.1(17) . . . . ?
C26 N4 C19 C20 -3.5(17) . . . . ?
C30 N4 C19 C20 170.2(11) . . . . ?
N4 C19 C20 C21 -8.3(18) . . . . ?
N4 C19 C20 C28 175.4(10) . . . . ?
C19 C20 C21 O7 -173.8(11) . . . . ?
C28 C20 C21 O7 2.3(17) . . . . ?
C19 C20 C21 C27 11.2(16) . . . . ?
C28 C20 C21 C27 -172.7(9) . . . . ?
C27 C22 C23 F2 176.6(9) . . . . ?
C27 C22 C23 C24 -1.4(18) . . . . ?
C35 N5 C24 C25 -128.2(13) . . . . ?
C32 N5 C24 C25 36.3(19) . . . . ?
C35 N5 C24 C23 53.2(17) . . . . ?
C32 N5 C24 C23 -142.3(12) . . . . ?
C22 C23 C24 N5 -179.4(11) . . . . ?
F2 C23 C24 N5 2.7(16) . . . . ?
C22 C23 C24 C25 2.0(18) . . . . ?
F2 C23 C24 C25 -176.0(10) . . . . ?
C29 O8 C25 C26 13.5(16) . . . . ?
C29 O8 C25 C24 -166.1(10) . . . . ?
N5 C24 C25 O8 -0.4(18) . . . . ?
C23 C24 C25 O8 178.3(10) . . . . ?
N5 C24 C25 C26 -180.0(11) . . . . ?
C23 C24 C25 C26 -1.3(17) . . . . ?
C19 N4 C26 C25 -173.1(10) . . . . ?
C30 N4 C26 C25 12.8(15) . . . . ?
C19 N4 C26 C27 11.8(16) . . . . ?
C30 N4 C26 C27 -162.3(10) . . . . ?
O8 C25 C26 N4 5.6(17) . . . . ?
C24 C25 C26 N4 -174.8(10) . . . . ?
O8 C25 C26 C27 -179.3(10) . . . . ?
C24 C25 C26 C27 0.3(17) . . . . ?
C23 C22 C27 C26 0.2(16) . . . . ?
C23 C22 C27 C21 -176.2(9) . . . . ?
N4 C26 C27 C22 175.4(10) . . . . ?
C25 C26 C27 C22 0.4(16) . . . . ?
N4 C26 C27 C21 -8.2(16) . . . . ?
C25 C26 C27 C21 176.8(10) . . . . ?
O7 C21 C27 C22 -1.8(17) . . . . ?
C20 C21 C27 C22 173.4(10) . . . . ?
O7 C21 C27 C26 -178.1(10) . . . . ?
C20 C21 C27 C26 -3.0(15) . . . . ?
C19 C20 C28 O5 0.0(18) . . . . ?
C21 C20 C28 O5 -176.2(12) . . . . ?
C19 C20 C28 O6 178.4(11) . . . . ?
C21 C20 C28 O6 2.1(16) . . . . ?
C25 O8 C29 C30 -48.2(13) . . . . ?
C19 N4 C30 C31 18.1(16) . . . . ?
C26 N4 C30 C31 -168.0(10) . . . . ?
C19 N4 C30 C29 140.3(13) . . . . ?
C26 N4 C30 C29 -45.8(16) . . . . ?
O8 C29 C30 N4 62.5(14) . . . . ?
O8 C29 C30 C31 -173.7(10) . . . . ?
C24 N5 C32 C33 -111.0(15) . . . . ?
C35 N5 C32 C33 54.7(18) . . . . ?
C34 N6 C33 C32 61.6(13) . . . . ?
C36 N6 C33 C32 -177.2(10) . . . . ?
N5 C32 C33 N6 -59.2(16) . . . . ?
C33 N6 C34 C35 -61.0(17) . . . . ?
C36 N6 C34 C35 178.6(16) . . . . ?
C24 N5 C35 C34 115.4(13) . . . . ?
C32 N5 C35 C34 -51.2(15) . . . . ?
N6 C34 C35 N5 55.1(18) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.78 2.539(17) 152.9 . yes
O6 H6 O7 0.82 1.72 2.491(18) 156.4 . yes
O10 H10B N6 0.80 2.40 2.788(17) 110.6 3_445 yes
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.111
_cell_measurement_pressure       4.05


# start Validation Reply Form
_vrf_ATOM007_LH_PE_4p05          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_PE_4p05          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_PE_4p05          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_PE_4p05          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_PE_4p05          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_PE_4p05          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_PE_4p05          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_PE_4p05          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_PE_4p05          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_4p05          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT111_LH_PE_4p05          
;
RESPONSE: The structure is chiral.

;
_vrf_PLAT721_LH_PE_4p05          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints

;
_vrf_PLAT910_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_PE_4p05          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_PE_4p05          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_PE_4p05          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_PE_4p05          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_OFLO_0p28
_database_code_depnum_ccdc_archive 'CCDC 2481339'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_040522_run1_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   29.962(13)
_cell_length_b                   6.6982(11)
_cell_length_c                   16.738(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.82(3)
_cell_angle_gamma                90
_cell_volume                     3247.3(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3332
_cell_measurement_theta_min      3.122
_cell_measurement_theta_max      23.178
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6588
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            3332
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.122
_diffrn_reflns_theta_max         23.178
_diffrn_reflns_theta_full        23.178
_diffrn_measured_fraction_theta_max 0.349
_diffrn_measured_fraction_theta_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.349
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.349
_diffrn_reflns_point_group_measured_fraction_full 0.349
_reflns_number_total             803
_reflns_number_gt                430
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_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] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         803
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      0.890
_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
F1 F 0.5705(3) 0.7044(5) 0.7792(2) 0.063(6) Uani 1 1 d D . . . .
O1 O 0.6450(4) 0.6159(7) 0.5654(3) 0.050(5) Uani 1 1 d D . . . .
O4 O 0.4381(4) 0.7999(6) 0.2712(3) 0.055(7) Uani 1 1 d D . . . .
C11 C 0.5244(5) 0.7326(10) 0.5572(5) 0.038(5) Uani 1 1 d D . . . .
O2 O 0.4439(4) 0.8146(7) 0.5190(3) 0.049(6) Uani 1 1 d D . . . .
N3 N 0.5624(6) 0.6945(10) 0.4464(5) 0.044(5) Uani 1 1 d D . . . .
N1 N 0.6484(6) 0.6283(10) 0.7364(5) 0.041(5) Uani 1 1 d D . . . .
C7 C 0.5675(6) 0.6985(12) 0.6953(5) 0.033(5) Uani 1 1 d D . . . .
C10 C 0.5641(6) 0.6912(11) 0.5315(5) 0.037(5) Uani 1 1 d D . . . .
C3 C 0.5216(7) 0.7332(14) 0.3927(6) 0.044(5) Uani 1 1 d D . . . .
H3 H 0.521170 0.733630 0.337006 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6087(7) 0.6540(11) 0.6744(6) 0.035(5) Uani 1 1 d D . . . .
O3 O 0.4016(5) 0.8570(8) 0.3688(4) 0.062(6) Uani 1 1 d D . . . .
H3A H 0.407033 0.850229 0.419293 0.093 Uiso 1 1 calc R U . . .
C4 C 0.4809(7) 0.7716(12) 0.4111(6) 0.042(5) Uani 1 1 d D . . . .
C6 C 0.5251(6) 0.7365(11) 0.6421(5) 0.037(6) Uani 1 1 d D . . . .
H6 H 0.498870 0.762619 0.660402 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6045(6) 0.6511(12) 0.5875(5) 0.041(5) Uani 1 1 d D . . . .
N2 N 0.7410(5) 0.6182(9) 0.8378(4) 0.055(6) Uani 1 1 d D . . . .
C13 C 0.4386(6) 0.8094(12) 0.3455(6) 0.048(6) Uani 1 1 d D . . . .
C16 C 0.7096(5) 0.7751(11) 0.8463(5) 0.054(7) Uani 1 1 d D . . . .
H16A H 0.727000 0.896947 0.863002 0.065 Uiso 1 1 calc R U . . .
H16B H 0.694910 0.739360 0.889670 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4803(5) 0.7729(11) 0.4968(5) 0.037(5) Uani 1 1 d D . . . .
C1 C 0.6381(6) 0.5404(9) 0.4816(4) 0.054(7) Uani 1 1 d D . . . .
H1A H 0.624007 0.409122 0.477245 0.065 Uiso 1 1 calc R U . . .
H1B H 0.667587 0.528635 0.468097 0.065 Uiso 1 1 calc R U . . .
C12 C 0.6268(6) 0.8864(8) 0.4208(4) 0.050(8) Uani 1 1 d D . . . .
H12A H 0.605435 0.967435 0.381622 0.076 Uiso 1 1 calc R U . . .
H12B H 0.655464 0.878159 0.405228 0.076 Uiso 1 1 calc R U . . .
H12C H 0.632195 0.945035 0.474792 0.076 Uiso 1 1 calc R U . . .
C2 C 0.6073(6) 0.6817(9) 0.4222(5) 0.044(6) Uani 1 1 d D . . . .
H2 H 0.601211 0.625139 0.366451 0.053 Uiso 1 1 calc R U . . .
C17 C 0.6727(5) 0.8137(10) 0.7672(4) 0.051(7) Uani 1 1 d D . . . .
H17A H 0.650851 0.911116 0.777426 0.061 Uiso 1 1 calc R U . . .
H17B H 0.686785 0.867947 0.725763 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7154(5) 0.4352(10) 0.8100(4) 0.044(6) Uani 1 1 d D . . . .
H15A H 0.699613 0.392201 0.850968 0.053 Uiso 1 1 calc R U . . .
H15B H 0.736622 0.330477 0.803914 0.053 Uiso 1 1 calc R U . . .
C18 C 0.7769(6) 0.5853(12) 0.9144(5) 0.074(7) Uani 1 1 d D . . . .
H18A H 0.789071 0.711538 0.937106 0.110 Uiso 1 1 calc R U . . .
H18B H 0.801264 0.506333 0.902896 0.110 Uiso 1 1 calc R U . . .
H18C H 0.763919 0.516363 0.953471 0.110 Uiso 1 1 calc R U . . .
C14 C 0.6809(5) 0.4691(10) 0.7294(4) 0.048(6) Uani 1 1 d D . . . .
H14A H 0.696885 0.505733 0.687873 0.058 Uiso 1 1 calc R U . . .
H14B H 0.664044 0.346560 0.711696 0.058 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 C7 1.384(8) . ?
O1 C9 1.377(14) . ?
O1 C1 1.456(7) . ?
O4 C13 1.241(8) . ?
C11 C10 1.391(13) . ?
C11 C6 1.416(9) . ?
C11 C5 1.471(11) . ?
O2 C5 1.269(14) . ?
N3 C3 1.345(16) . ?
N3 C10 1.412(9) . ?
N3 C2 1.502(16) . ?
N1 C8 1.374(18) . ?
N1 C17 1.465(11) . ?
N1 C14 1.470(12) . ?
C7 C6 1.377(17) . ?
C7 C8 1.398(19) . ?
C10 C9 1.355(16) . ?
C3 C4 1.355(18) . ?
C3 H3 0.9300 . ?
C8 C9 1.427(10) . ?
O3 C13 1.307(17) . ?
O3 H3A 0.8200 . ?
C4 C5 1.439(11) . ?
C4 C13 1.471(15) . ?
C6 H6 0.9300 . ?
N2 C16 1.441(12) . ?
N2 C15 1.458(11) . ?
N2 C18 1.465(10) . ?
C16 C17 1.515(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.506(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.493(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.492(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 113.6(11) . . ?
C10 C11 C6 121.4(11) . . ?
C10 C11 C5 120.9(8) . . ?
C6 C11 C5 117.7(11) . . ?
C3 N3 C10 117.9(13) . . ?
C3 N3 C2 123.7(8) . . ?
C10 N3 C2 117.8(12) . . ?
C8 N1 C17 114.5(8) . . ?
C8 N1 C14 119.6(8) . . ?
C17 N1 C14 111.2(11) . . ?
C6 C7 F1 117.5(12) . . ?
C6 C7 C8 127.3(10) . . ?
F1 C7 C8 115.3(12) . . ?
C9 C10 C11 120.5(8) . . ?
C9 C10 N3 119.8(12) . . ?
C11 C10 N3 119.7(12) . . ?
N3 C3 C4 127.1(10) . . ?
N3 C3 H3 116.5 . . ?
C4 C3 H3 116.5 . . ?
N1 C8 C7 119.1(9) . . ?
N1 C8 C9 127.1(14) . . ?
C7 C8 C9 113.8(13) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 118.0(13) . . ?
C3 C4 C13 121.0(9) . . ?
C5 C4 C13 121.0(13) . . ?
C7 C6 C11 114.8(12) . . ?
C7 C6 H6 122.6 . . ?
C11 C6 H6 122.6 . . ?
C10 C9 O1 122.7(8) . . ?
C10 C9 C8 122.3(12) . . ?
O1 C9 C8 114.9(13) . . ?
C16 N2 C15 110.0(11) . . ?
C16 N2 C18 112.0(7) . . ?
C15 N2 C18 111.2(7) . . ?
O4 C13 O3 121.2(15) . . ?
O4 C13 C4 121.8(12) . . ?
O3 C13 C4 117.0(10) . . ?
N2 C16 C17 112.7(7) . . ?
N2 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
N2 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O2 C5 C4 121.6(13) . . ?
O2 C5 C11 121.9(9) . . ?
C4 C5 C11 116.4(11) . . ?
O1 C1 C2 109.3(6) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12 C2 N3 109.5(9) . . ?
C12 C2 C1 114.2(12) . . ?
N3 C2 C1 107.3(8) . . ?
C12 C2 H2 108.6 . . ?
N3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
N1 C17 C16 110.4(7) . . ?
N1 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N2 C15 C14 110.2(7) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 110.9(7) . . ?
N1 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
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
C6 C11 C10 C9 0.8(13) . . . . ?
C5 C11 C10 C9 -178.9(9) . . . . ?
C6 C11 C10 N3 -178.2(8) . . . . ?
C5 C11 C10 N3 2.2(11) . . . . ?
C3 N3 C10 C9 179.4(10) . . . . ?
C2 N3 C10 C9 -8.5(13) . . . . ?
C3 N3 C10 C11 -1.7(14) . . . . ?
C2 N3 C10 C11 170.4(7) . . . . ?
C10 N3 C3 C4 0.5(18) . . . . ?
C2 N3 C3 C4 -171.1(8) . . . . ?
C17 N1 C8 C7 -84.3(12) . . . . ?
C14 N1 C8 C7 139.9(9) . . . . ?
C17 N1 C8 C9 92.1(11) . . . . ?
C14 N1 C8 C9 -43.7(14) . . . . ?
C6 C7 C8 N1 177.4(10) . . . . ?
F1 C7 C8 N1 -2.6(13) . . . . ?
C6 C7 C8 C9 0.5(16) . . . . ?
F1 C7 C8 C9 -179.4(6) . . . . ?
N3 C3 C4 C5 0.3(17) . . . . ?
N3 C3 C4 C13 -179.3(10) . . . . ?
F1 C7 C6 C11 178.7(5) . . . . ?
C8 C7 C6 C11 -1.3(16) . . . . ?
C10 C11 C6 C7 0.6(13) . . . . ?
C5 C11 C6 C7 -179.7(8) . . . . ?
C11 C10 C9 O1 -177.7(7) . . . . ?
N3 C10 C9 O1 1.2(15) . . . . ?
C11 C10 C9 C8 -1.6(15) . . . . ?
N3 C10 C9 C8 177.3(7) . . . . ?
C1 O1 C9 C10 -25.4(12) . . . . ?
C1 O1 C9 C8 158.3(6) . . . . ?
N1 C8 C9 C10 -175.6(9) . . . . ?
C7 C8 C9 C10 1.0(14) . . . . ?
N1 C8 C9 O1 0.8(14) . . . . ?
C7 C8 C9 O1 177.4(8) . . . . ?
C3 C4 C13 O4 2.9(15) . . . . ?
C5 C4 C13 O4 -176.7(7) . . . . ?
C3 C4 C13 O3 -176.0(9) . . . . ?
C5 C4 C13 O3 4.4(14) . . . . ?
C15 N2 C16 C17 -56.8(9) . . . . ?
C18 N2 C16 C17 179.0(8) . . . . ?
C3 C4 C5 O2 177.5(9) . . . . ?
C13 C4 C5 O2 -2.9(14) . . . . ?
C3 C4 C5 C11 0.2(13) . . . . ?
C13 C4 C5 C11 179.8(7) . . . . ?
C10 C11 C5 O2 -178.7(8) . . . . ?
C6 C11 C5 O2 1.7(12) . . . . ?
C10 C11 C5 C4 -1.4(12) . . . . ?
C6 C11 C5 C4 178.9(7) . . . . ?
C9 O1 C1 C2 55.0(11) . . . . ?
C3 N3 C2 C12 84.3(12) . . . . ?
C10 N3 C2 C12 -87.3(10) . . . . ?
C3 N3 C2 C1 -151.3(10) . . . . ?
C10 N3 C2 C1 37.2(9) . . . . ?
O1 C1 C2 C12 62.4(12) . . . . ?
O1 C1 C2 N3 -59.2(11) . . . . ?
C8 N1 C17 C16 168.0(10) . . . . ?
C14 N1 C17 C16 -52.6(8) . . . . ?
N2 C16 C17 N1 53.9(11) . . . . ?
C16 N2 C15 C14 58.8(8) . . . . ?
C18 N2 C15 C14 -176.6(8) . . . . ?
C8 N1 C14 C15 -166.7(10) . . . . ?
C17 N1 C14 C15 56.2(9) . . . . ?
N2 C15 C14 N1 -58.9(10) . . . . ?
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.025
_cell_measurement_pressure       0.28

# start Validation Reply Form
_vrf_ATOM007_OFLO_0p28           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_0p28           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_0p28           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_0p28           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_0p28           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_0p28           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_0p28           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_0p28           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_0p28           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_0p28           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_0p28           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_0p28           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_0p28           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_LH_PE_1p26
_database_code_depnum_ccdc_archive 'CCDC 2481332'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_Levo_HH_20241004_03

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.25(H4 O2)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   28.1035(17)
_cell_length_b                   6.5548(4)
_cell_length_c                   18.263(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.490(4)
_cell_angle_gamma                90
_cell_volume                     3085.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    14280
_cell_measurement_theta_min      2.347
_cell_measurement_theta_max      24.745
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.998
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon III'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14280
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         24.745
_diffrn_reflns_theta_full        24.745
_diffrn_measured_fraction_theta_max 0.619
_diffrn_measured_fraction_theta_full 0.619
_diffrn_reflns_Laue_measured_fraction_max 0.619
_diffrn_reflns_Laue_measured_fraction_full 0.619
_diffrn_reflns_point_group_measured_fraction_max 0.605
_diffrn_reflns_point_group_measured_fraction_full 0.605
_reflns_number_total             3200
_reflns_number_gt                2189
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_max     0.588
_reflns_Friedel_fraction_full    0.588
_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_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'

_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1743P)²+3.1394P] 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_abs_structure_details 
;
 Flack x determined using 757 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3200
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.2642
_refine_ls_wR_factor_gt          0.2173
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.999
_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
F1 F 0.2084(2) 0.4498(9) 0.7291(6) 0.0425(16) Uiso 1 1 d D U . . .
O1 O 0.3207(3) 0.4765(12) 1.2281(7) 0.051(2) Uiso 1 1 d D U . . .
O2 O 0.3744(3) 0.4756(12) 1.1646(7) 0.045(2) Uiso 1 1 d D U . . .
H2 H 0.371601 0.445443 1.119503 0.067 Uiso 1 1 calc R U . . .
O3 O 0.3359(2) 0.4805(9) 1.0137(6) 0.0317(17) Uiso 1 1 d D U . . .
O4 O 0.1021(2) 0.4557(9) 0.8742(6) 0.0339(17) Uiso 1 1 d D U . . .
N1 N 0.1911(2) 0.4629(11) 1.0171(6) 0.0260(18) Uiso 1 1 d D U . . .
N2 N 0.1113(3) 0.4740(11) 0.7272(6) 0.034(2) Uiso 1 1 d D U . . .
N3 N 0.0139(3) 0.6402(11) 0.6255(7) 0.034(2) Uiso 1 1 d D U . . .
C1 C 0.2340(3) 0.4636(13) 1.0853(7) 0.031(2) Uiso 1 1 d D U . . .
H1 H 0.229796 0.460035 1.133218 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2836(3) 0.4693(14) 1.0885(7) 0.030(2) Uiso 1 1 d D U . . .
C3 C 0.2913(3) 0.4728(12) 1.0154(7) 0.021(2) Uiso 1 1 d D U . . .
C4 C 0.2485(3) 0.4664(13) 0.8676(7) 0.027(2) Uiso 1 1 d D U . . .
H4 H 0.280833 0.467057 0.864796 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2046(3) 0.4629(13) 0.7998(7) 0.028(2) Uiso 1 1 d D U . . .
C6 C 0.1540(3) 0.4653(13) 0.7990(7) 0.026(2) Uiso 1 1 d D U . . .
C7 C 0.1507(3) 0.4606(13) 0.8727(7) 0.025(2) Uiso 1 1 d D U . . .
C8 C 0.1955(3) 0.4625(13) 0.9437(7) 0.026(2) Uiso 1 1 d D U . . .
C9 C 0.2449(3) 0.4690(12) 0.9418(7) 0.022(2) Uiso 1 1 d D U . . .
C10 C 0.3274(3) 0.4751(13) 1.1671(7) 0.030(2) Uiso 1 1 d D U . . .
C11 C 0.1004(3) 0.5412(14) 0.9444(7) 0.038(3) Uiso 1 1 d D U . . .
H11A H 0.065780 0.524812 0.943067 0.045 Uiso 1 1 calc R U . . .
H11B H 0.107642 0.686186 0.945764 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1388(3) 0.4435(13) 1.0188(7) 0.031(2) Uiso 1 1 d D U . . .
H12 H 0.130170 0.298998 1.019891 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1351(4) 0.5517(16) 1.0890(8) 0.042(3) Uiso 1 1 d D U . . .
H13A H 0.152954 0.473789 1.136636 0.064 Uiso 1 1 calc R U . . .
H13B H 0.099333 0.566343 1.080552 0.064 Uiso 1 1 calc R U . . .
H13C H 0.150786 0.684182 1.094602 0.064 Uiso 1 1 calc R U . . .
C14 C 0.0629(3) 0.3640(13) 0.7097(10) 0.038(3) Uiso 1 1 d D U . . .
H14A H 0.066308 0.279332 0.755101 0.046 Uiso 1 1 calc R U . . .
H14B H 0.056136 0.275360 0.664143 0.046 Uiso 1 1 calc R U . . .
C15 C 0.0180(3) 0.5092(13) 0.6920(8) 0.034(2) Uiso 1 1 d D U . . .
H15A H -0.013918 0.432717 0.678790 0.041 Uiso 1 1 calc R U . . .
H15B H 0.023395 0.591780 0.738777 0.041 Uiso 1 1 calc R U . . .
C16 C 0.0620(3) 0.7599(14) 0.6477(10) 0.040(3) Uiso 1 1 d D U . . .
H16A H 0.067263 0.841291 0.694637 0.048 Uiso 1 1 calc R U . . .
H16B H 0.059088 0.851826 0.604480 0.048 Uiso 1 1 calc R U . . .
C17 C 0.1079(3) 0.6197(13) 0.6648(8) 0.033(2) Uiso 1 1 d D U . . .
H17A H 0.104175 0.546876 0.616601 0.040 Uiso 1 1 calc R U . . .
H17B H 0.139578 0.699541 0.681913 0.040 Uiso 1 1 calc R U . . .
C18 C -0.0305(4) 0.7782(15) 0.6034(13) 0.052(3) Uiso 1 1 d D U . . .
H18A H -0.061661 0.700144 0.591341 0.078 Uiso 1 1 calc R U . . .
H18B H -0.033323 0.856163 0.557409 0.078 Uiso 1 1 calc R U . . .
H18C H -0.025769 0.868798 0.647096 0.078 Uiso 1 1 calc R U . . .
F2 F 0.28676(19) 0.7266(8) 0.7617(5) 0.0391(15) Uiso 1 1 d D U . . .
O5 O 0.1836(3) 0.6959(12) 0.2640(7) 0.060(3) Uiso 1 1 d D U . . .
O6 O 0.1287(2) 0.7097(12) 0.3245(7) 0.043(2) Uiso 1 1 d D U . . .
H6 H 0.130902 0.696144 0.370369 0.065 Uiso 1 1 calc R U . . .
O7 O 0.1628(2) 0.6790(9) 0.4742(6) 0.0328(17) Uiso 1 1 d D U . . .
O8 O 0.3967(2) 0.6881(9) 0.6246(6) 0.0377(18) Uiso 1 1 d D U . . .
N4 N 0.3092(2) 0.6599(10) 0.4786(6) 0.0293(19) Uiso 1 1 d D U . . .
N5 N 0.3846(2) 0.7103(11) 0.7678(6) 0.032(2) Uiso 1 1 d D U . . .
N6 N 0.4832(3) 0.5847(11) 0.8787(7) 0.036(2) Uiso 1 1 d D U . . .
C19 C 0.2680(3) 0.6647(13) 0.4095(8) 0.035(3) Uiso 1 1 d D U . . .
H19 H 0.273221 0.656012 0.362408 0.041 Uiso 1 1 calc R U . . .
C20 C 0.2177(3) 0.6820(13) 0.4047(7) 0.031(2) Uiso 1 1 d D U . . .
C21 C 0.2080(3) 0.6787(12) 0.4751(7) 0.026(2) Uiso 1 1 d D U . . .
C22 C 0.2485(3) 0.6925(13) 0.6237(7) 0.030(2) Uiso 1 1 d D U . . .
H22 H 0.215895 0.692951 0.625515 0.036 Uiso 1 1 calc R U . . .
C23 C 0.2915(3) 0.7024(13) 0.6917(7) 0.029(2) Uiso 1 1 d D U . . .
C24 C 0.3426(3) 0.6999(13) 0.6948(6) 0.025(2) Uiso 1 1 d D U . . .
C25 C 0.3474(3) 0.6950(12) 0.6216(7) 0.025(2) Uiso 1 1 d D U . . .
C26 C 0.3032(3) 0.6815(12) 0.5493(7) 0.026(2) Uiso 1 1 d D U . . .
C27 C 0.2532(3) 0.6815(12) 0.5508(7) 0.024(2) Uiso 1 1 d D U . . .
C28 C 0.1758(3) 0.6954(13) 0.3236(7) 0.033(2) Uiso 1 1 d D U . . .
C29 C 0.3994(3) 0.7420(14) 0.5502(7) 0.033(2) Uiso 1 1 d D U . . .
H29A H 0.434432 0.721188 0.553993 0.040 Uiso 1 1 calc R U . . .
H29B H 0.390819 0.885154 0.539140 0.040 Uiso 1 1 calc R U . . .
C30 C 0.3623(3) 0.6144(14) 0.4833(7) 0.032(2) Uiso 1 1 d D U . . .
H30 H 0.369792 0.470303 0.497548 0.038 Uiso 1 1 calc R U . . .
C31 C 0.3684(4) 0.6517(18) 0.4060(9) 0.055(3) Uiso 1 1 d D U . . .
H31A H 0.348739 0.551964 0.367205 0.082 Uiso 1 1 calc R U . . .
H31B H 0.404328 0.641294 0.414921 0.082 Uiso 1 1 calc R U . . .
H31C H 0.355871 0.785790 0.386544 0.082 Uiso 1 1 calc R U . . .
C32 C 0.4304(3) 0.8350(12) 0.7839(9) 0.029(2) Uiso 1 1 d D U . . .
H32A H 0.433899 0.932187 0.825774 0.035 Uiso 1 1 calc R U . . .
H32B H 0.426395 0.911066 0.736203 0.035 Uiso 1 1 calc R U . . .
C33 C 0.4787(3) 0.7044(13) 0.8092(7) 0.033(2) Uiso 1 1 d D U . . .
H33A H 0.476584 0.614309 0.765846 0.040 Uiso 1 1 calc R U . . .
H33B H 0.509017 0.790464 0.822061 0.040 Uiso 1 1 calc R U . . .
C34 C 0.4377(3) 0.4489(14) 0.8581(9) 0.041(3) Uiso 1 1 d D U . . .
H34A H 0.441505 0.364843 0.903856 0.049 Uiso 1 1 calc R U . . .
H34B H 0.435596 0.359428 0.814623 0.049 Uiso 1 1 calc R U . . .
C35 C 0.3889(3) 0.5743(14) 0.8339(8) 0.037(3) Uiso 1 1 d D U . . .
H35A H 0.358931 0.484730 0.817433 0.045 Uiso 1 1 calc R U . . .
H35B H 0.389581 0.654326 0.878968 0.045 Uiso 1 1 calc R U . . .
C36 C 0.5309(4) 0.4638(17) 0.9082(12) 0.055(3) Uiso 1 1 d D U . . .
H36A H 0.534029 0.392063 0.864473 0.083 Uiso 1 1 calc R U . . .
H36B H 0.529788 0.367474 0.947046 0.083 Uiso 1 1 calc R U . . .
H36C H 0.560203 0.552568 0.932347 0.083 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.3537(18) 0.500000 0.058(4) Uiso 1 2 d DGS . P . .
H9A H -0.001872 0.436909 0.464444 0.088 Uiso 0.5 1 d DG U P . .
H9B H -0.023033 0.391870 0.515042 0.088 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.3847(17) 1.000000 0.053(3) Uiso 1 2 d DGS . P . .
H10A H -0.015930 0.283571 0.974487 0.079 Uiso 0.5 1 d DG U P . .
H10B H -0.018800 0.482819 0.976797 0.079 Uiso 0.5 1 d DG U P . .
_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 C5 1.339(10) . ?
O1 C10 1.203(11) . ?
O2 C10 1.338(9) . ?
O2 H2 0.8200 . ?
O3 C3 1.267(8) . ?
O4 C7 1.378(8) . ?
O4 C11 1.418(11) . ?
N1 C1 1.344(10) . ?
N1 C8 1.394(10) . ?
N1 C12 1.489(9) . ?
N2 C6 1.382(10) . ?
N2 C14 1.457(9) . ?
N2 C17 1.460(11) . ?
N3 C15 1.455(11) . ?
N3 C18 1.462(9) . ?
N3 C16 1.475(9) . ?
C1 C2 1.372(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.436(11) . ?
C2 C10 1.471(11) . ?
C3 C9 1.453(10) . ?
C4 C5 1.355(10) . ?
C4 C9 1.400(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.417(10) . ?
C6 C7 1.387(10) . ?
C7 C8 1.400(10) . ?
C8 C9 1.403(9) . ?
C11 C12 1.500(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.504(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.511(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.511(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.347(10) . ?
O5 C28 1.190(11) . ?
O6 C28 1.336(9) . ?
O6 H6 0.8200 . ?
O7 C21 1.263(8) . ?
O8 C25 1.365(8) . ?
O8 C29 1.435(11) . ?
N4 C19 1.329(10) . ?
N4 C26 1.375(10) . ?
N4 C30 1.489(9) . ?
N5 C24 1.385(10) . ?
N5 C32 1.452(8) . ?
N5 C35 1.466(11) . ?
N6 C33 1.454(11) . ?
N6 C36 1.463(10) . ?
N6 C34 1.478(9) . ?
C19 C20 1.385(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.418(11) . ?
C20 C28 1.483(11) . ?
C21 C27 1.458(11) . ?
C22 C23 1.345(10) . ?
C22 C27 1.391(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.413(9) . ?
C24 C25 1.397(10) . ?
C25 C26 1.409(10) . ?
C26 C27 1.417(9) . ?
C29 C30 1.505(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.508(12) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.514(9) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.508(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8334 . ?
O9 H9B 0.8359 . ?
O9 H9A 0.8(3) 2_556 ?
O9 H9B 0.84(14) 2_556 ?
O10 H10A 0.8311 . ?
O10 H10B 0.8329 . ?
O10 H10A 0.8(2) 2_557 ?
O10 H10B 0.83(18) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 113.6(8) . . ?
C1 N1 C8 120.1(8) . . ?
C1 N1 C12 120.6(9) . . ?
C8 N1 C12 119.0(8) . . ?
C6 N2 C14 124.7(9) . . ?
C6 N2 C17 121.9(8) . . ?
C14 N2 C17 112.9(8) . . ?
C15 N3 C18 111.7(10) . . ?
C15 N3 C16 109.0(9) . . ?
C18 N3 C16 109.6(7) . . ?
N1 C1 C2 124.1(11) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 119.1(9) . . ?
C1 C2 C10 118.9(10) . . ?
C3 C2 C10 122.0(8) . . ?
O3 C3 C2 122.7(9) . . ?
O3 C3 C9 120.7(9) . . ?
C2 C3 C9 116.6(7) . . ?
C5 C4 C9 119.6(8) . . ?
C5 C4 H4 120.2 . . ?
C9 C4 H4 120.2 . . ?
F1 C5 C4 119.3(8) . . ?
F1 C5 C6 117.1(8) . . ?
C4 C5 C6 123.6(10) . . ?
N2 C6 C7 123.6(7) . . ?
N2 C6 C5 120.0(10) . . ?
C7 C6 C5 116.5(8) . . ?
O4 C7 C6 118.1(8) . . ?
O4 C7 C8 120.9(9) . . ?
C6 C7 C8 121.0(8) . . ?
N1 C8 C7 120.0(8) . . ?
N1 C8 C9 119.3(8) . . ?
C7 C8 C9 120.7(9) . . ?
C4 C9 C8 118.5(8) . . ?
C4 C9 C3 120.7(7) . . ?
C8 C9 C3 120.8(9) . . ?
O1 C10 O2 123.5(10) . . ?
O1 C10 C2 121.7(9) . . ?
O2 C10 C2 114.8(10) . . ?
O4 C11 C12 112.3(8) . . ?
O4 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
O4 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N1 C12 C11 107.7(8) . . ?
N1 C12 C13 112.4(8) . . ?
C11 C12 C13 107.6(8) . . ?
N1 C12 H12 109.7 . . ?
C11 C12 H12 109.7 . . ?
C13 C12 H12 109.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.3(7) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 109.4(9) . . ?
N3 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
N3 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
N3 C16 C17 110.3(7) . . ?
N3 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N3 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N2 C17 C16 110.1(9) . . ?
N2 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 112.9(8) . . ?
C19 N4 C26 120.1(8) . . ?
C19 N4 C30 122.2(9) . . ?
C26 N4 C30 117.5(8) . . ?
C24 N5 C32 124.6(9) . . ?
C24 N5 C35 121.4(8) . . ?
C32 N5 C35 113.7(8) . . ?
C33 N6 C36 111.2(10) . . ?
C33 N6 C34 109.7(9) . . ?
C36 N6 C34 109.9(7) . . ?
N4 C19 C20 122.9(11) . . ?
N4 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C19 C20 C21 120.1(9) . . ?
C19 C20 C28 116.9(10) . . ?
C21 C20 C28 122.9(8) . . ?
O7 C21 C20 122.9(9) . . ?
O7 C21 C27 120.3(9) . . ?
C20 C21 C27 116.8(7) . . ?
C23 C22 C27 119.5(9) . . ?
C23 C22 H22 120.3 . . ?
C27 C22 H22 120.3 . . ?
C22 C23 F2 119.2(8) . . ?
C22 C23 C24 124.2(10) . . ?
F2 C23 C24 116.5(8) . . ?
N5 C24 C25 123.5(8) . . ?
N5 C24 C23 120.0(9) . . ?
C25 C24 C23 116.4(8) . . ?
O8 C25 C24 116.4(8) . . ?
O8 C25 C26 122.5(9) . . ?
C24 C25 C26 120.9(8) . . ?
N4 C26 C25 119.6(8) . . ?
N4 C26 C27 120.9(8) . . ?
C25 C26 C27 119.5(9) . . ?
C22 C27 C26 119.5(9) . . ?
C22 C27 C21 122.0(7) . . ?
C26 C27 C21 118.5(9) . . ?
O5 C28 O6 123.7(10) . . ?
O5 C28 C20 123.4(9) . . ?
O6 C28 C20 112.9(10) . . ?
O8 C29 C30 110.6(8) . . ?
O8 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
O8 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
N4 C30 C29 106.8(8) . . ?
N4 C30 C31 113.5(8) . . ?
C29 C30 C31 111.7(9) . . ?
N4 C30 H30 108.2 . . ?
C29 C30 H30 108.2 . . ?
C31 C30 H30 108.2 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 111.0(7) . . ?
N5 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
N5 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
N6 C33 C32 109.1(9) . . ?
N6 C33 H33A 109.9 . . ?
C32 C33 H33A 109.9 . . ?
N6 C33 H33B 109.9 . . ?
C32 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
N6 C34 C35 109.9(7) . . ?
N6 C34 H34A 109.7 . . ?
C35 C34 H34A 109.7 . . ?
N6 C34 H34B 109.7 . . ?
C35 C34 H34B 109.7 . . ?
H34A C34 H34B 108.2 . . ?
N5 C35 C34 109.9(9) . . ?
N5 C35 H35A 109.7 . . ?
C34 C35 H35A 109.7 . . ?
N5 C35 H35B 109.7 . . ?
C34 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 104.1 . . ?
H9A O9 H9A 98.3 . 2_556 ?
H9B O9 H9A 50.6 . 2_556 ?
H9A O9 H9B 50.6 . 2_556 ?
H9B O9 H9B 145.2 . 2_556 ?
H9A O9 H9B 104.1 2_556 2_556 ?
H10A O10 H10B 103.9 . . ?
H10A O10 H10A 74.2 . 2_557 ?
H10B O10 H10A 172.6 . 2_557 ?
H10A O10 H10B 172.6 . 2_557 ?
H10B O10 H10B 78.9 . 2_557 ?
H10A O10 H10B 103.9 2_557 2_557 ?
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
C8 N1 C1 C2 1.7(13) . . . . ?
C12 N1 C1 C2 176.2(8) . . . . ?
N1 C1 C2 C3 -0.6(14) . . . . ?
N1 C1 C2 C10 178.4(8) . . . . ?
C1 C2 C3 O3 179.1(8) . . . . ?
C10 C2 C3 O3 0.2(13) . . . . ?
C1 C2 C3 C9 -0.3(12) . . . . ?
C10 C2 C3 C9 -179.2(7) . . . . ?
C9 C4 C5 F1 -176.6(7) . . . . ?
C9 C4 C5 C6 1.2(14) . . . . ?
C14 N2 C6 C7 -39.1(14) . . . . ?
C17 N2 C6 C7 131.8(10) . . . . ?
C14 N2 C6 C5 141.5(9) . . . . ?
C17 N2 C6 C5 -47.6(13) . . . . ?
F1 C5 C6 N2 -6.2(12) . . . . ?
C4 C5 C6 N2 176.1(9) . . . . ?
F1 C5 C6 C7 174.4(8) . . . . ?
C4 C5 C6 C7 -3.3(13) . . . . ?
C11 O4 C7 C6 -153.1(8) . . . . ?
C11 O4 C7 C8 26.4(12) . . . . ?
N2 C6 C7 O4 2.8(13) . . . . ?
C5 C6 C7 O4 -177.8(8) . . . . ?
N2 C6 C7 C8 -176.7(8) . . . . ?
C5 C6 C7 C8 2.7(13) . . . . ?
C1 N1 C8 C7 179.7(8) . . . . ?
C12 N1 C8 C7 5.1(12) . . . . ?
C1 N1 C8 C9 -1.9(12) . . . . ?
C12 N1 C8 C9 -176.4(7) . . . . ?
O4 C7 C8 N1 -1.1(13) . . . . ?
C6 C7 C8 N1 178.4(8) . . . . ?
O4 C7 C8 C9 -179.5(8) . . . . ?
C6 C7 C8 C9 -0.1(13) . . . . ?
C5 C4 C9 C8 1.6(12) . . . . ?
C5 C4 C9 C3 -180.0(8) . . . . ?
N1 C8 C9 C4 179.4(7) . . . . ?
C7 C8 C9 C4 -2.2(12) . . . . ?
N1 C8 C9 C3 1.0(12) . . . . ?
C7 C8 C9 C3 179.4(8) . . . . ?
O3 C3 C9 C4 2.3(12) . . . . ?
C2 C3 C9 C4 -178.3(8) . . . . ?
O3 C3 C9 C8 -179.4(8) . . . . ?
C2 C3 C9 C8 0.1(12) . . . . ?
C1 C2 C10 O1 -0.5(14) . . . . ?
C3 C2 C10 O1 178.4(9) . . . . ?
C1 C2 C10 O2 178.5(9) . . . . ?
C3 C2 C10 O2 -2.6(12) . . . . ?
C7 O4 C11 C12 -55.2(10) . . . . ?
C1 N1 C12 C11 154.2(8) . . . . ?
C8 N1 C12 C11 -31.3(11) . . . . ?
C1 N1 C12 C13 35.8(12) . . . . ?
C8 N1 C12 C13 -149.7(8) . . . . ?
O4 C11 C12 N1 56.2(10) . . . . ?
O4 C11 C12 C13 177.6(7) . . . . ?
C6 N2 C14 C15 118.0(12) . . . . ?
C17 N2 C14 C15 -53.7(14) . . . . ?
C18 N3 C15 C14 177.5(9) . . . . ?
C16 N3 C15 C14 -61.2(11) . . . . ?
N2 C14 C15 N3 57.4(14) . . . . ?
C15 N3 C16 C17 61.6(13) . . . . ?
C18 N3 C16 C17 -175.9(13) . . . . ?
C6 N2 C17 C16 -119.1(10) . . . . ?
C14 N2 C17 C16 52.8(12) . . . . ?
N3 C16 C17 N2 -56.5(13) . . . . ?
C26 N4 C19 C20 -2.9(13) . . . . ?
C30 N4 C19 C20 171.9(8) . . . . ?
N4 C19 C20 C21 -5.2(14) . . . . ?
N4 C19 C20 C28 177.1(7) . . . . ?
C19 C20 C21 O7 -174.7(8) . . . . ?
C28 C20 C21 O7 2.8(13) . . . . ?
C19 C20 C21 C27 7.2(12) . . . . ?
C28 C20 C21 C27 -175.2(7) . . . . ?
C27 C22 C23 F2 175.6(7) . . . . ?
C27 C22 C23 C24 -0.9(14) . . . . ?
C32 N5 C24 C25 40.3(13) . . . . ?
C35 N5 C24 C25 -132.3(10) . . . . ?
C32 N5 C24 C23 -137.0(9) . . . . ?
C35 N5 C24 C23 50.4(12) . . . . ?
C22 C23 C24 N5 -179.8(8) . . . . ?
F2 C23 C24 N5 3.6(12) . . . . ?
C22 C23 C24 C25 2.7(13) . . . . ?
F2 C23 C24 C25 -173.9(7) . . . . ?
C29 O8 C25 C24 -163.1(7) . . . . ?
C29 O8 C25 C26 21.8(11) . . . . ?
N5 C24 C25 O8 4.0(12) . . . . ?
C23 C24 C25 O8 -178.6(7) . . . . ?
N5 C24 C25 C26 179.1(8) . . . . ?
C23 C24 C25 C26 -3.5(12) . . . . ?
C19 N4 C26 C25 -174.2(7) . . . . ?
C30 N4 C26 C25 10.7(11) . . . . ?
C19 N4 C26 C27 8.6(12) . . . . ?
C30 N4 C26 C27 -166.5(7) . . . . ?
O8 C25 C26 N4 0.2(12) . . . . ?
C24 C25 C26 N4 -174.6(8) . . . . ?
O8 C25 C26 C27 177.5(8) . . . . ?
C24 C25 C26 C27 2.7(12) . . . . ?
C23 C22 C27 C26 -0.2(13) . . . . ?
C23 C22 C27 C21 -177.5(7) . . . . ?
N4 C26 C27 C22 176.5(7) . . . . ?
C25 C26 C27 C22 -0.7(12) . . . . ?
N4 C26 C27 C21 -6.1(12) . . . . ?
C25 C26 C27 C21 176.7(7) . . . . ?
O7 C21 C27 C22 -2.5(12) . . . . ?
C20 C21 C27 C22 175.6(8) . . . . ?
O7 C21 C27 C26 -179.9(8) . . . . ?
C20 C21 C27 C26 -1.7(11) . . . . ?
C19 C20 C28 O5 -1.4(14) . . . . ?
C21 C20 C28 O5 -179.1(10) . . . . ?
C19 C20 C28 O6 179.4(8) . . . . ?
C21 C20 C28 O6 1.7(12) . . . . ?
C25 O8 C29 C30 -53.4(9) . . . . ?
C19 N4 C30 C29 144.9(8) . . . . ?
C26 N4 C30 C29 -40.1(10) . . . . ?
C19 N4 C30 C31 21.4(12) . . . . ?
C26 N4 C30 C31 -163.7(8) . . . . ?
O8 C29 C30 N4 61.5(9) . . . . ?
O8 C29 C30 C31 -173.9(7) . . . . ?
C24 N5 C32 C33 -119.6(11) . . . . ?
C35 N5 C32 C33 53.5(14) . . . . ?
C36 N6 C33 C32 -176.9(9) . . . . ?
C34 N6 C33 C32 61.3(10) . . . . ?
N5 C32 C33 N6 -56.8(13) . . . . ?
C33 N6 C34 C35 -61.8(13) . . . . ?
C36 N6 C34 C35 175.6(12) . . . . ?
C24 N5 C35 C34 120.3(9) . . . . ?
C32 N5 C35 C34 -53.0(12) . . . . ?
N6 C34 C35 N5 56.0(14) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.80 2.528(15) 146.7 . yes
O6 H6 O7 0.82 1.75 2.519(14) 155.9 . yes
O10 H10A N6 0.83 2.17 2.858(13) 139.5 3_445 yes
O9 H9B N3 0.84 2.47 2.866(12) 109.7 . yes
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.158
_cell_measurement_pressure       1.26


# start Validation Reply Form
_vrf_ATOM007_LH_PE_1p26          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_PE_1p26          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT420_LH_ME_1p26          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT111_LH_PE_1p26          
;
RESPONSE: The structure is chiral.


;
_vrf_PLAT250_LH_PE_1p26          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_PE_1p26          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_PE_1p26          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_PE_1p26          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_PE_1p26          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_PE_1p26          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_PE_1p26          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT721_LH_PE_1p26          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints


;
_vrf_PLAT910_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_PE_1p26          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_PE_1p26          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_PE_1p26          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_PE_1p26          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_OFLO_0p76
_database_code_depnum_ccdc_archive 'CCDC 2481340'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_050522_run1_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   29.630(7)
_cell_length_b                   6.5439(6)
_cell_length_c                   16.5404(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.354(16)
_cell_angle_gamma                90
_cell_volume                     3107.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5492
_cell_measurement_theta_min      2.542
_cell_measurement_theta_max      23.285
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6705
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            5492
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         23.285
_diffrn_reflns_theta_full        23.285
_diffrn_measured_fraction_theta_max 0.352
_diffrn_measured_fraction_theta_full 0.352
_diffrn_reflns_Laue_measured_fraction_max 0.352
_diffrn_reflns_Laue_measured_fraction_full 0.352
_diffrn_reflns_point_group_measured_fraction_max 0.352
_diffrn_reflns_point_group_measured_fraction_full 0.352
_reflns_number_total             792
_reflns_number_gt                493
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.4936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         792
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      0.975
_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
F1 F 0.5698(3) 0.7053(5) 0.7813(2) 0.055(5) Uani 1 1 d D . . . .
O1 O 0.6463(4) 0.6114(6) 0.5657(3) 0.039(5) Uani 1 1 d D . . . .
O4 O 0.4377(4) 0.8010(6) 0.2708(3) 0.042(6) Uani 1 1 d D . . . .
C11 C 0.5243(5) 0.7320(9) 0.5581(4) 0.028(5) Uani 1 1 d D . . . .
O2 O 0.4442(4) 0.8159(6) 0.5210(3) 0.034(5) Uani 1 1 d D . . . .
N3 N 0.5625(5) 0.6932(8) 0.4464(4) 0.029(5) Uani 1 1 d D . . . .
N1 N 0.6505(5) 0.6222(8) 0.7395(4) 0.028(5) Uani 1 1 d D . . . .
C7 C 0.5682(6) 0.6976(11) 0.6979(5) 0.027(5) Uani 1 1 d D . . . .
C10 C 0.5644(5) 0.6870(9) 0.5319(4) 0.024(4) Uani 1 1 d D . . . .
C3 C 0.5222(6) 0.7330(10) 0.3911(5) 0.028(5) Uani 1 1 d D . . . .
H3 H 0.522101 0.734872 0.334856 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6094(6) 0.6535(10) 0.6758(5) 0.027(4) Uani 1 1 d D . . . .
O3 O 0.4009(4) 0.8606(7) 0.3700(3) 0.044(5) Uani 1 1 d D . . . .
H3A H 0.406819 0.858495 0.421106 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4814(6) 0.7707(10) 0.4118(5) 0.029(5) Uani 1 1 d D . . . .
C6 C 0.5256(5) 0.7352(9) 0.6439(4) 0.027(5) Uani 1 1 d D . . . .
H6 H 0.499156 0.761270 0.662893 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6058(5) 0.6472(10) 0.5892(4) 0.027(5) Uani 1 1 d D . . . .
N2 N 0.7428(4) 0.6125(8) 0.8383(3) 0.042(5) Uani 1 1 d D . . . .
C13 C 0.4387(6) 0.8112(10) 0.3452(5) 0.034(5) Uani 1 1 d D . . . .
C16 C 0.7114(5) 0.7787(10) 0.8472(4) 0.042(6) Uani 1 1 d D . . . .
H16A H 0.729214 0.903203 0.862497 0.050 Uiso 1 1 calc R U . . .
H16B H 0.696470 0.745941 0.891600 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4797(5) 0.7727(9) 0.4972(4) 0.026(5) Uani 1 1 d D . . . .
C1 C 0.6378(5) 0.5361(9) 0.4806(3) 0.041(6) Uani 1 1 d D . . . .
H1A H 0.623045 0.403030 0.476661 0.049 Uiso 1 1 calc R U . . .
H1B H 0.667275 0.520902 0.465461 0.049 Uiso 1 1 calc R U . . .
C12 C 0.6276(6) 0.8919(9) 0.4201(4) 0.049(8) Uani 1 1 d D . . . .
H12A H 0.605299 0.978978 0.384174 0.074 Uiso 1 1 calc R U . . .
H12B H 0.655244 0.883493 0.399778 0.074 Uiso 1 1 calc R U . . .
H12C H 0.635431 0.947371 0.475608 0.074 Uiso 1 1 calc R U . . .
C2 C 0.6072(5) 0.6814(9) 0.4215(4) 0.031(5) Uani 1 1 d D . . . .
H2 H 0.601062 0.623995 0.365106 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6749(4) 0.8128(9) 0.7678(4) 0.038(6) Uani 1 1 d D . . . .
H17A H 0.652799 0.914376 0.776753 0.046 Uiso 1 1 calc R U . . .
H17B H 0.689355 0.863877 0.725204 0.046 Uiso 1 1 calc R U . . .
C15 C 0.7166(4) 0.4264(9) 0.8116(3) 0.035(5) Uani 1 1 d D . . . .
H15A H 0.700475 0.385659 0.853419 0.042 Uiso 1 1 calc R U . . .
H15B H 0.737838 0.317552 0.806147 0.042 Uiso 1 1 calc R U . . .
C18 C 0.7785(5) 0.5815(11) 0.9154(4) 0.063(6) Uani 1 1 d D . . . .
H18A H 0.795698 0.705854 0.930490 0.095 Uiso 1 1 calc R U . . .
H18B H 0.799272 0.475012 0.907507 0.095 Uiso 1 1 calc R U . . .
H18C H 0.764063 0.543094 0.959130 0.095 Uiso 1 1 calc R U . . .
C14 C 0.6819(4) 0.4575(9) 0.7299(3) 0.036(5) Uani 1 1 d D . . . .
H14A H 0.697800 0.492875 0.687142 0.043 Uiso 1 1 calc R U . . .
H14B H 0.664380 0.332790 0.713179 0.043 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 C7 1.369(6) . ?
O1 C9 1.368(13) . ?
O1 C1 1.454(6) . ?
O4 C13 1.225(7) . ?
C11 C10 1.394(12) . ?
C11 C6 1.409(7) . ?
C11 C5 1.473(11) . ?
O2 C5 1.245(13) . ?
N3 C3 1.337(16) . ?
N3 C10 1.401(7) . ?
N3 C2 1.484(15) . ?
N1 C8 1.413(16) . ?
N1 C14 1.458(11) . ?
N1 C17 1.459(10) . ?
C7 C6 1.376(16) . ?
C7 C8 1.390(18) . ?
C10 C9 1.378(15) . ?
C3 C4 1.356(17) . ?
C3 H3 0.9300 . ?
C8 C9 1.410(8) . ?
O3 C13 1.326(15) . ?
O3 H3A 0.8200 . ?
C4 C5 1.426(9) . ?
C4 C13 1.481(15) . ?
C6 H6 0.9300 . ?
N2 C15 1.453(10) . ?
N2 C18 1.456(9) . ?
N2 C16 1.462(11) . ?
C16 C17 1.497(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.498(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.507(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.495(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 112.4(9) . . ?
C10 C11 C6 120.2(10) . . ?
C10 C11 C5 120.9(6) . . ?
C6 C11 C5 118.9(10) . . ?
C3 N3 C10 120.1(11) . . ?
C3 N3 C2 121.8(6) . . ?
C10 N3 C2 117.6(11) . . ?
C8 N1 C14 118.7(6) . . ?
C8 N1 C17 112.4(7) . . ?
C14 N1 C17 112.8(10) . . ?
F1 C7 C6 116.4(10) . . ?
F1 C7 C8 117.4(11) . . ?
C6 C7 C8 126.2(7) . . ?
C9 C10 C11 120.6(6) . . ?
C9 C10 N3 120.4(11) . . ?
C11 C10 N3 118.9(11) . . ?
N3 C3 C4 124.2(7) . . ?
N3 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C7 C8 C9 115.1(12) . . ?
C7 C8 N1 118.9(7) . . ?
C9 C8 N1 126.0(12) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.3(12) . . ?
C3 C4 C13 119.7(7) . . ?
C5 C4 C13 120.1(12) . . ?
C7 C6 C11 116.4(11) . . ?
C7 C6 H6 121.8 . . ?
C11 C6 H6 121.8 . . ?
O1 C9 C10 122.0(6) . . ?
O1 C9 C8 116.3(11) . . ?
C10 C9 C8 121.6(11) . . ?
C15 N2 C18 111.6(6) . . ?
C15 N2 C16 110.4(9) . . ?
C18 N2 C16 111.0(6) . . ?
O4 C13 O3 120.8(13) . . ?
O4 C13 C4 122.7(11) . . ?
O3 C13 C4 116.5(7) . . ?
N2 C16 C17 111.2(6) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O2 C5 C4 123.8(12) . . ?
O2 C5 C11 120.6(7) . . ?
C4 C5 C11 115.5(10) . . ?
O1 C1 C2 110.3(6) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C1 106.9(6) . . ?
N3 C2 C12 110.3(8) . . ?
C1 C2 C12 114.1(11) . . ?
N3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C12 C2 H2 108.5 . . ?
N1 C17 C16 110.3(6) . . ?
N1 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N2 C15 C14 110.9(5) . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 108.4(6) . . ?
N1 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
N1 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
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
C6 C11 C10 C9 -0.7(10) . . . . ?
C5 C11 C10 C9 -179.4(7) . . . . ?
C6 C11 C10 N3 -177.4(6) . . . . ?
C5 C11 C10 N3 3.9(10) . . . . ?
C3 N3 C10 C9 -179.6(8) . . . . ?
C2 N3 C10 C9 -7.4(10) . . . . ?
C3 N3 C10 C11 -2.9(11) . . . . ?
C2 N3 C10 C11 169.3(6) . . . . ?
C10 N3 C3 C4 0.5(12) . . . . ?
C2 N3 C3 C4 -171.4(7) . . . . ?
F1 C7 C8 C9 179.9(5) . . . . ?
C6 C7 C8 C9 -0.3(13) . . . . ?
F1 C7 C8 N1 -0.9(11) . . . . ?
C6 C7 C8 N1 178.9(7) . . . . ?
C14 N1 C8 C7 138.6(8) . . . . ?
C17 N1 C8 C7 -86.6(9) . . . . ?
C14 N1 C8 C9 -42.2(11) . . . . ?
C17 N1 C8 C9 92.5(9) . . . . ?
N3 C3 C4 C5 0.9(12) . . . . ?
N3 C3 C4 C13 -179.4(8) . . . . ?
F1 C7 C6 C11 178.5(5) . . . . ?
C8 C7 C6 C11 -1.2(13) . . . . ?
C10 C11 C6 C7 1.7(10) . . . . ?
C5 C11 C6 C7 -179.6(7) . . . . ?
C1 O1 C9 C10 -24.2(9) . . . . ?
C1 O1 C9 C8 159.5(5) . . . . ?
C11 C10 C9 O1 -177.0(6) . . . . ?
N3 C10 C9 O1 -0.4(12) . . . . ?
C11 C10 C9 C8 -0.9(11) . . . . ?
N3 C10 C9 C8 175.7(6) . . . . ?
C7 C8 C9 O1 177.7(7) . . . . ?
N1 C8 C9 O1 -1.4(10) . . . . ?
C7 C8 C9 C10 1.4(11) . . . . ?
N1 C8 C9 C10 -177.7(7) . . . . ?
C3 C4 C13 O4 4.3(11) . . . . ?
C5 C4 C13 O4 -176.1(6) . . . . ?
C3 C4 C13 O3 -175.6(7) . . . . ?
C5 C4 C13 O3 4.1(10) . . . . ?
C15 N2 C16 C17 -56.4(7) . . . . ?
C18 N2 C16 C17 179.4(7) . . . . ?
C3 C4 C5 O2 176.4(7) . . . . ?
C13 C4 C5 O2 -3.3(11) . . . . ?
C3 C4 C5 C11 0.1(10) . . . . ?
C13 C4 C5 C11 -179.6(6) . . . . ?
C10 C11 C5 O2 -178.9(7) . . . . ?
C6 C11 C5 O2 2.4(10) . . . . ?
C10 C11 C5 C4 -2.5(9) . . . . ?
C6 C11 C5 C4 178.8(6) . . . . ?
C9 O1 C1 C2 55.8(9) . . . . ?
C3 N3 C2 C1 -150.9(7) . . . . ?
C10 N3 C2 C1 37.0(8) . . . . ?
C3 N3 C2 C12 84.5(9) . . . . ?
C10 N3 C2 C12 -87.6(8) . . . . ?
O1 C1 C2 N3 -60.9(10) . . . . ?
O1 C1 C2 C12 61.4(11) . . . . ?
C8 N1 C17 C16 167.0(8) . . . . ?
C14 N1 C17 C16 -55.5(7) . . . . ?
N2 C16 C17 N1 53.8(9) . . . . ?
C18 N2 C15 C14 -176.8(7) . . . . ?
C16 N2 C15 C14 59.3(7) . . . . ?
C8 N1 C14 C15 -167.9(8) . . . . ?
C17 N1 C14 C15 57.5(7) . . . . ?
N2 C15 C14 N1 -58.9(9) . . . . ?
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.028
_cell_measurement_pressure       0.76

# start Validation Reply Form
_vrf_ATOM007_OFLO_0p76           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_0p76           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_0p76           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_0p76           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_0p76           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_0p76           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_0p76           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_0p76           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_0p76           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_0p76           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_0p76           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_0p76           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_0p76           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_LH_PE_2p99
_database_code_depnum_ccdc_archive 'CCDC 2481335'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_Levo_HH_20241025_07

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.25(H4 O2)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   27.717(3)
_cell_length_b                   6.3111(6)
_cell_length_c                   17.983(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.633(9)
_cell_angle_gamma                90
_cell_volume                     2881.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    11056
_cell_measurement_theta_min      1.585
_cell_measurement_theta_max      24.797
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.997
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon III'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11056
_diffrn_reflns_av_unetI/netI     0.0995
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.585
_diffrn_reflns_theta_max         24.797
_diffrn_reflns_theta_full        24.797
_diffrn_measured_fraction_theta_max 0.639
_diffrn_measured_fraction_theta_full 0.639
_diffrn_reflns_Laue_measured_fraction_max 0.639
_diffrn_reflns_Laue_measured_fraction_full 0.639
_diffrn_reflns_point_group_measured_fraction_max 0.606
_diffrn_reflns_point_group_measured_fraction_full 0.606
_reflns_number_total             3011
_reflns_number_gt                1993
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.566
_reflns_Friedel_fraction_full    0.566
_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_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'

_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1322P)²+1.3070P] 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_abs_structure_details 
;
 Flack x determined using 647 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3011
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.2338
_refine_ls_wR_factor_gt          0.2063
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      2.533
_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
F1 F 0.20949(16) 0.4409(9) 0.7256(5) 0.0329(14) Uiso 1 1 d D U . . .
O1 O 0.3217(2) 0.4609(12) 1.2325(6) 0.0406(19) Uiso 1 1 d D U . . .
O2 O 0.3764(2) 0.4589(12) 1.1694(6) 0.0340(17) Uiso 1 1 d D U . . .
H2 H 0.373536 0.467110 1.122267 0.051 Uiso 1 1 calc R U . . .
O3 O 0.33832(18) 0.4717(9) 1.0165(6) 0.0244(15) Uiso 1 1 d D U . . .
O4 O 0.10134(19) 0.4375(10) 0.8708(5) 0.0271(15) Uiso 1 1 d D U . . .
N1 N 0.1911(2) 0.4549(11) 1.0177(6) 0.0222(18) Uiso 1 1 d D U . . .
N2 N 0.1108(2) 0.4578(12) 0.7216(6) 0.0250(18) Uiso 1 1 d D U . . .
N3 N 0.0119(2) 0.6394(11) 0.6239(6) 0.0252(19) Uiso 1 1 d D U . . .
C1 C 0.2341(3) 0.4561(14) 1.0870(7) 0.026(2) Uiso 1 1 d D U . . .
H1 H 0.229812 0.453395 1.135672 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2846(3) 0.4613(14) 1.0899(6) 0.023(2) Uiso 1 1 d D U . . .
C3 C 0.2928(2) 0.4632(13) 1.0167(6) 0.018(2) Uiso 1 1 d D U . . .
C4 C 0.2501(3) 0.4571(13) 0.8667(7) 0.020(2) Uiso 1 1 d D U . . .
H4 H 0.282915 0.459091 0.864175 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2054(3) 0.4535(14) 0.7976(6) 0.024(2) Uiso 1 1 d D U . . .
C6 C 0.1536(2) 0.4548(14) 0.7958(6) 0.018(2) Uiso 1 1 d D U . . .
C7 C 0.1506(2) 0.4464(14) 0.8706(6) 0.019(2) Uiso 1 1 d D U . . .
C8 C 0.1957(2) 0.4512(14) 0.9436(6) 0.020(2) Uiso 1 1 d D U . . .
C9 C 0.2459(3) 0.4576(14) 0.9415(7) 0.021(2) Uiso 1 1 d D U . . .
C10 C 0.3285(3) 0.4638(14) 1.1710(7) 0.025(2) Uiso 1 1 d D U . . .
C11 C 0.0985(3) 0.5297(15) 0.9408(6) 0.030(2) Uiso 1 1 d D U . . .
H11A H 0.063361 0.509405 0.938862 0.035 Uiso 1 1 calc R U . . .
H11B H 0.104677 0.680924 0.940471 0.035 Uiso 1 1 calc R U . . .
C12 C 0.1379(2) 0.4366(15) 1.0184(6) 0.027(2) Uiso 1 1 d D U . . .
H12 H 0.129579 0.287223 1.022510 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1339(3) 0.5609(16) 1.0877(8) 0.035(2) Uiso 1 1 d D U . . .
H13A H 0.152883 0.488351 1.137908 0.052 Uiso 1 1 calc R U . . .
H13B H 0.097533 0.573616 1.079298 0.052 Uiso 1 1 calc R U . . .
H13C H 0.148614 0.699464 1.089731 0.052 Uiso 1 1 calc R U . . .
C14 C 0.0612(2) 0.3502(13) 0.7071(8) 0.024(2) Uiso 1 1 d D U . . .
H14A H 0.065532 0.261033 0.753274 0.029 Uiso 1 1 calc R U . . .
H14B H 0.051794 0.260057 0.659686 0.029 Uiso 1 1 calc R U . . .
C15 C 0.0175(3) 0.5079(14) 0.6939(7) 0.030(2) Uiso 1 1 d D U . . .
H15A H -0.015265 0.433956 0.683815 0.036 Uiso 1 1 calc R U . . .
H15B H 0.025901 0.595697 0.741780 0.036 Uiso 1 1 calc R U . . .
C16 C 0.0609(3) 0.7595(15) 0.6421(9) 0.033(3) Uiso 1 1 d D U . . .
H16A H 0.067820 0.848665 0.689197 0.039 Uiso 1 1 calc R U . . .
H16B H 0.056952 0.850313 0.596492 0.039 Uiso 1 1 calc R U . . .
C17 C 0.1066(3) 0.6093(13) 0.6584(7) 0.027(2) Uiso 1 1 d D U . . .
H17A H 0.101720 0.533723 0.608979 0.033 Uiso 1 1 calc R U . . .
H17B H 0.139009 0.689937 0.674901 0.033 Uiso 1 1 calc R U . . .
C18 C -0.0318(3) 0.7906(15) 0.6037(11) 0.038(3) Uiso 1 1 d D U . . .
H18A H -0.064605 0.715358 0.582465 0.058 Uiso 1 1 calc R U . . .
H18B H -0.030592 0.888993 0.563735 0.058 Uiso 1 1 calc R U . . .
H18C H -0.028642 0.866397 0.651708 0.058 Uiso 1 1 calc R U . . .
F2 F 0.28546(16) 0.7376(9) 0.7653(5) 0.0335(15) Uiso 1 1 d D U . . .
O5 O 0.1849(3) 0.7087(12) 0.2593(7) 0.051(2) Uiso 1 1 d D U . . .
O6 O 0.1280(2) 0.7252(12) 0.3184(6) 0.0368(18) Uiso 1 1 d D U . . .
H6 H 0.129913 0.724415 0.365087 0.055 Uiso 1 1 calc R U . . .
O7 O 0.16163(19) 0.6802(10) 0.4719(6) 0.0268(15) Uiso 1 1 d D U . . .
O8 O 0.39843(19) 0.7055(10) 0.6288(6) 0.0315(17) Uiso 1 1 d D U . . .
N4 N 0.3107(2) 0.6630(11) 0.4796(6) 0.0248(19) Uiso 1 1 d D U . . .
N5 N 0.3846(2) 0.7282(12) 0.7736(6) 0.0243(18) Uiso 1 1 d D U . . .
N6 N 0.4848(2) 0.5856(11) 0.8823(6) 0.0269(19) Uiso 1 1 d D U . . .
C19 C 0.2692(3) 0.6693(14) 0.4085(7) 0.027(2) Uiso 1 1 d D U . . .
H19 H 0.274895 0.660907 0.360984 0.033 Uiso 1 1 calc R U . . .
C20 C 0.2182(3) 0.6877(15) 0.4026(6) 0.029(2) Uiso 1 1 d D U . . .
C21 C 0.2078(2) 0.6838(13) 0.4735(6) 0.020(2) Uiso 1 1 d D U . . .
C22 C 0.2471(3) 0.6986(14) 0.6239(7) 0.023(2) Uiso 1 1 d D U . . .
H22 H 0.213685 0.696098 0.624513 0.028 Uiso 1 1 calc R U . . .
C23 C 0.2906(3) 0.7137(14) 0.6940(7) 0.024(2) Uiso 1 1 d D U . . .
C24 C 0.3428(3) 0.7140(14) 0.6989(6) 0.022(2) Uiso 1 1 d D U . . .
C25 C 0.3482(2) 0.7051(13) 0.6254(6) 0.019(2) Uiso 1 1 d D U . . .
C26 C 0.3046(3) 0.6878(14) 0.5519(6) 0.024(2) Uiso 1 1 d D U . . .
C27 C 0.2532(2) 0.6872(13) 0.5515(6) 0.020(2) Uiso 1 1 d D U . . .
C28 C 0.1759(3) 0.7089(15) 0.3193(7) 0.030(3) Uiso 1 1 d D U . . .
C29 C 0.4018(3) 0.7524(15) 0.5531(7) 0.033(2) Uiso 1 1 d D U . . .
H29A H 0.437538 0.729570 0.558109 0.039 Uiso 1 1 calc R U . . .
H29B H 0.392904 0.899987 0.539369 0.039 Uiso 1 1 calc R U . . .
C30 C 0.3647(3) 0.6136(15) 0.4868(7) 0.028(2) Uiso 1 1 d D U . . .
H30 H 0.372374 0.465762 0.504230 0.033 Uiso 1 1 calc R U . . .
C31 C 0.3703(4) 0.6381(18) 0.4076(8) 0.043(3) Uiso 1 1 d D U . . .
H31A H 0.346924 0.541428 0.368476 0.064 Uiso 1 1 calc R U . . .
H31B H 0.405958 0.607846 0.415330 0.064 Uiso 1 1 calc R U . . .
H31C H 0.361630 0.780738 0.388277 0.064 Uiso 1 1 calc R U . . .
C32 C 0.4321(3) 0.8505(14) 0.7890(9) 0.027(2) Uiso 1 1 d D U . . .
H32A H 0.437444 0.949732 0.832803 0.032 Uiso 1 1 calc R U . . .
H32B H 0.427704 0.931398 0.740865 0.032 Uiso 1 1 calc R U . . .
C33 C 0.4797(3) 0.7099(14) 0.8114(7) 0.026(2) Uiso 1 1 d D U . . .
H33A H 0.475818 0.616513 0.766463 0.032 Uiso 1 1 calc R U . . .
H33B H 0.511037 0.795472 0.823355 0.032 Uiso 1 1 calc R U . . .
C34 C 0.4382(3) 0.4511(15) 0.8608(8) 0.032(2) Uiso 1 1 d D U . . .
H34A H 0.442273 0.359219 0.906196 0.039 Uiso 1 1 calc R U . . .
H34B H 0.434871 0.362457 0.814950 0.039 Uiso 1 1 calc R U . . .
C35 C 0.3895(3) 0.5829(14) 0.8396(7) 0.028(2) Uiso 1 1 d D U . . .
H35A H 0.358776 0.491614 0.822973 0.033 Uiso 1 1 calc R U . . .
H35B H 0.391373 0.662925 0.886774 0.033 Uiso 1 1 calc R U . . .
C36 C 0.5320(3) 0.4556(17) 0.9082(10) 0.039(3) Uiso 1 1 d D U . . .
H36A H 0.535574 0.396868 0.861482 0.059 Uiso 1 1 calc R U . . .
H36B H 0.529283 0.342956 0.942226 0.059 Uiso 1 1 calc R U . . .
H36C H 0.562208 0.541184 0.938104 0.059 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.3439(18) 0.500000 0.041(3) Uiso 1 2 d DGS . P . .
H9A H -0.023556 0.338783 0.515966 0.062 Uiso 0.5 1 d DG U P . .
H9B H -0.012175 0.418731 0.459520 0.062 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.4015(18) 1.000000 0.041(3) Uiso 1 2 d DGS . P . .
H10A H -0.028428 0.451712 0.991514 0.061 Uiso 0.5 1 d DG U P . .
H10B H -0.007494 0.291637 0.974540 0.061 Uiso 0.5 1 d DG U P . .
_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 C5 1.347(9) . ?
O1 C10 1.194(10) . ?
O2 C10 1.341(8) . ?
O2 H2 0.8200 . ?
O3 C3 1.264(8) . ?
O4 C7 1.367(8) . ?
O4 C11 1.417(10) . ?
N1 C1 1.336(10) . ?
N1 C8 1.389(10) . ?
N1 C12 1.484(8) . ?
N2 C6 1.384(9) . ?
N2 C17 1.453(10) . ?
N2 C14 1.461(8) . ?
N3 C15 1.465(11) . ?
N3 C18 1.468(8) . ?
N3 C16 1.471(8) . ?
C1 C2 1.380(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.423(10) . ?
C2 C10 1.477(10) . ?
C3 C9 1.451(10) . ?
C4 C5 1.357(10) . ?
C4 C9 1.396(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.423(9) . ?
C6 C7 1.383(10) . ?
C7 C8 1.405(10) . ?
C8 C9 1.407(9) . ?
C11 C12 1.505(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.513(11) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.512(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.514(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.354(10) . ?
O5 C28 1.201(10) . ?
O6 C28 1.326(9) . ?
O6 H6 0.8200 . ?
O7 C21 1.269(8) . ?
O8 C25 1.368(8) . ?
O8 C29 1.432(10) . ?
N4 C19 1.334(10) . ?
N4 C26 1.385(10) . ?
N4 C30 1.484(8) . ?
N5 C24 1.381(10) . ?
N5 C32 1.452(8) . ?
N5 C35 1.463(10) . ?
N6 C36 1.452(9) . ?
N6 C33 1.455(11) . ?
N6 C34 1.462(8) . ?
C19 C20 1.379(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.416(10) . ?
C20 C28 1.493(10) . ?
C21 C27 1.461(10) . ?
C22 C23 1.354(10) . ?
C22 C27 1.381(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.414(9) . ?
C24 C25 1.391(10) . ?
C25 C26 1.391(10) . ?
C26 C27 1.423(9) . ?
C29 C30 1.504(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.502(11) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.507(9) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.501(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8125 . ?
O9 H9B 0.8183 . ?
O9 H9A 0.813(19) 2_556 ?
O9 H9B 0.8(2) 2_556 ?
O10 H10A 0.8051 . ?
O10 H10B 0.8107 . ?
O10 H10A 0.81(16) 2_557 ?
O10 H10B 0.8(2) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 113.3(7) . . ?
C1 N1 C8 120.2(7) . . ?
C1 N1 C12 120.7(9) . . ?
C8 N1 C12 118.8(7) . . ?
C6 N2 C17 122.2(7) . . ?
C6 N2 C14 123.2(8) . . ?
C17 N2 C14 113.0(7) . . ?
C15 N3 C18 111.9(9) . . ?
C15 N3 C16 109.4(7) . . ?
C18 N3 C16 108.4(7) . . ?
N1 C1 C2 123.3(10) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 120.0(8) . . ?
C1 C2 C10 117.3(9) . . ?
C3 C2 C10 122.7(7) . . ?
O3 C3 C2 122.2(8) . . ?
O3 C3 C9 121.3(9) . . ?
C2 C3 C9 116.5(7) . . ?
C5 C4 C9 119.1(7) . . ?
C5 C4 H4 120.5 . . ?
C9 C4 H4 120.5 . . ?
F1 C5 C4 119.0(7) . . ?
F1 C5 C6 116.8(7) . . ?
C4 C5 C6 124.2(9) . . ?
C7 C6 N2 125.1(7) . . ?
C7 C6 C5 115.6(8) . . ?
N2 C6 C5 119.3(9) . . ?
O4 C7 C6 117.0(7) . . ?
O4 C7 C8 121.0(9) . . ?
C6 C7 C8 122.0(7) . . ?
N1 C8 C7 120.4(7) . . ?
N1 C8 C9 119.8(7) . . ?
C7 C8 C9 119.7(9) . . ?
C4 C9 C8 119.3(8) . . ?
C4 C9 C3 120.6(7) . . ?
C8 C9 C3 120.1(9) . . ?
O1 C10 O2 123.0(8) . . ?
O1 C10 C2 122.7(7) . . ?
O2 C10 C2 114.2(9) . . ?
O4 C11 C12 112.7(7) . . ?
O4 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
O4 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 C11 108.3(8) . . ?
N1 C12 C13 111.6(7) . . ?
C11 C12 C13 107.2(8) . . ?
N1 C12 H12 109.9 . . ?
C11 C12 H12 109.9 . . ?
C13 C12 H12 109.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.2(7) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 108.0(9) . . ?
N3 C15 H15A 110.1 . . ?
C14 C15 H15A 110.1 . . ?
N3 C15 H15B 110.1 . . ?
C14 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
N3 C16 C17 110.2(7) . . ?
N3 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N3 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N2 C17 C16 111.3(9) . . ?
N2 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N2 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 114.2(7) . . ?
C19 N4 C26 121.0(7) . . ?
C19 N4 C30 122.8(9) . . ?
C26 N4 C30 116.1(7) . . ?
C24 N5 C32 124.2(9) . . ?
C24 N5 C35 121.1(7) . . ?
C32 N5 C35 113.4(7) . . ?
C36 N6 C33 110.1(9) . . ?
C36 N6 C34 110.0(7) . . ?
C33 N6 C34 108.5(8) . . ?
N4 C19 C20 122.6(10) . . ?
N4 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
C19 C20 C21 120.1(8) . . ?
C19 C20 C28 116.9(9) . . ?
C21 C20 C28 122.9(7) . . ?
O7 C21 C20 123.1(8) . . ?
O7 C21 C27 119.7(9) . . ?
C20 C21 C27 117.2(7) . . ?
C23 C22 C27 118.8(8) . . ?
C23 C22 H22 120.6 . . ?
C27 C22 H22 120.6 . . ?
F2 C23 C22 119.8(7) . . ?
F2 C23 C24 115.7(8) . . ?
C22 C23 C24 124.5(10) . . ?
N5 C24 C25 124.0(7) . . ?
N5 C24 C23 120.0(9) . . ?
C25 C24 C23 116.0(8) . . ?
O8 C25 C24 116.9(7) . . ?
O8 C25 C26 121.5(9) . . ?
C24 C25 C26 121.5(7) . . ?
N4 C26 C25 121.0(7) . . ?
N4 C26 C27 119.5(8) . . ?
C25 C26 C27 119.4(9) . . ?
C22 C27 C26 119.8(8) . . ?
C22 C27 C21 121.5(7) . . ?
C26 C27 C21 118.7(9) . . ?
O5 C28 O6 123.8(9) . . ?
O5 C28 C20 122.7(8) . . ?
O6 C28 C20 113.6(9) . . ?
O8 C29 C30 110.5(8) . . ?
O8 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
O8 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
N4 C30 C31 112.3(8) . . ?
N4 C30 C29 106.9(8) . . ?
C31 C30 C29 113.3(9) . . ?
N4 C30 H30 108.0 . . ?
C31 C30 H30 108.0 . . ?
C29 C30 H30 108.0 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 111.6(7) . . ?
N5 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
N5 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
N6 C33 C32 108.5(8) . . ?
N6 C33 H33A 110.0 . . ?
C32 C33 H33A 110.0 . . ?
N6 C33 H33B 110.0 . . ?
C32 C33 H33B 110.0 . . ?
H33A C33 H33B 108.4 . . ?
N6 C34 C35 110.8(7) . . ?
N6 C34 H34A 109.5 . . ?
C35 C34 H34A 109.5 . . ?
N6 C34 H34B 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
N5 C35 C34 109.5(9) . . ?
N5 C35 H35A 109.8 . . ?
C34 C35 H35A 109.8 . . ?
N5 C35 H35B 109.8 . . ?
C34 C35 H35B 109.8 . . ?
H35A C35 H35B 108.2 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 103.5 . . ?
H9A O9 H9A 175.4 . 2_556 ?
H9B O9 H9A 79.2 . 2_556 ?
H9A O9 H9B 79.2 . 2_556 ?
H9B O9 H9B 109.5 . 2_556 ?
H9A O9 H9B 103.5 2_556 2_556 ?
H10A O10 H10B 102.7 . . ?
H10A O10 H10A 133.6 . 2_557 ?
H10B O10 H10A 117.0 . 2_557 ?
H10A O10 H10B 117.0 . 2_557 ?
H10B O10 H10B 62.4 . 2_557 ?
H10A O10 H10B 102.7 2_557 2_557 ?
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
C8 N1 C1 C2 2.3(14) . . . . ?
C12 N1 C1 C2 176.4(8) . . . . ?
N1 C1 C2 C3 -0.7(15) . . . . ?
N1 C1 C2 C10 179.5(8) . . . . ?
C1 C2 C3 O3 178.7(8) . . . . ?
C10 C2 C3 O3 -1.5(13) . . . . ?
C1 C2 C3 C9 -0.5(13) . . . . ?
C10 C2 C3 C9 179.2(7) . . . . ?
C9 C4 C5 F1 -176.3(8) . . . . ?
C9 C4 C5 C6 1.4(13) . . . . ?
C17 N2 C6 C7 131.9(10) . . . . ?
C14 N2 C6 C7 -32.3(14) . . . . ?
C17 N2 C6 C5 -50.1(13) . . . . ?
C14 N2 C6 C5 145.7(8) . . . . ?
F1 C5 C6 C7 173.8(8) . . . . ?
C4 C5 C6 C7 -3.9(13) . . . . ?
F1 C5 C6 N2 -4.4(12) . . . . ?
C4 C5 C6 N2 177.9(8) . . . . ?
C11 O4 C7 C6 -151.0(8) . . . . ?
C11 O4 C7 C8 27.7(12) . . . . ?
N2 C6 C7 O4 1.0(14) . . . . ?
C5 C6 C7 O4 -177.1(8) . . . . ?
N2 C6 C7 C8 -177.7(8) . . . . ?
C5 C6 C7 C8 4.2(13) . . . . ?
C1 N1 C8 C7 179.0(8) . . . . ?
C12 N1 C8 C7 4.8(12) . . . . ?
C1 N1 C8 C9 -2.6(13) . . . . ?
C12 N1 C8 C9 -176.8(8) . . . . ?
O4 C7 C8 N1 -2.4(13) . . . . ?
C6 C7 C8 N1 176.3(8) . . . . ?
O4 C7 C8 C9 179.2(8) . . . . ?
C6 C7 C8 C9 -2.2(14) . . . . ?
C5 C4 C9 C8 1.0(13) . . . . ?
C5 C4 C9 C3 -179.5(7) . . . . ?
N1 C8 C9 C4 -179.0(8) . . . . ?
C7 C8 C9 C4 -0.6(13) . . . . ?
N1 C8 C9 C3 1.4(13) . . . . ?
C7 C8 C9 C3 179.8(8) . . . . ?
O3 C3 C9 C4 1.3(13) . . . . ?
C2 C3 C9 C4 -179.4(8) . . . . ?
O3 C3 C9 C8 -179.1(8) . . . . ?
C2 C3 C9 C8 0.1(12) . . . . ?
C1 C2 C10 O1 0.2(14) . . . . ?
C3 C2 C10 O1 -179.5(9) . . . . ?
C1 C2 C10 O2 177.1(8) . . . . ?
C3 C2 C10 O2 -2.7(13) . . . . ?
C7 O4 C11 C12 -54.8(10) . . . . ?
C1 N1 C12 C11 156.3(8) . . . . ?
C8 N1 C12 C11 -29.6(11) . . . . ?
C1 N1 C12 C13 38.5(12) . . . . ?
C8 N1 C12 C13 -147.4(9) . . . . ?
O4 C11 C12 N1 54.7(10) . . . . ?
O4 C11 C12 C13 175.3(7) . . . . ?
C6 N2 C14 C15 111.5(11) . . . . ?
C17 N2 C14 C15 -54.0(13) . . . . ?
C18 N3 C15 C14 177.0(8) . . . . ?
C16 N3 C15 C14 -62.9(10) . . . . ?
N2 C14 C15 N3 59.2(12) . . . . ?
C15 N3 C16 C17 61.1(12) . . . . ?
C18 N3 C16 C17 -176.7(11) . . . . ?
C6 N2 C17 C16 -114.7(9) . . . . ?
C14 N2 C17 C16 50.9(12) . . . . ?
N3 C16 C17 N2 -54.2(12) . . . . ?
C26 N4 C19 C20 -4.0(14) . . . . ?
C30 N4 C19 C20 171.3(9) . . . . ?
N4 C19 C20 C21 -5.1(15) . . . . ?
N4 C19 C20 C28 175.6(8) . . . . ?
C19 C20 C21 O7 -173.3(8) . . . . ?
C28 C20 C21 O7 6.0(14) . . . . ?
C19 C20 C21 C27 7.6(13) . . . . ?
C28 C20 C21 C27 -173.1(8) . . . . ?
C27 C22 C23 F2 176.1(8) . . . . ?
C27 C22 C23 C24 -1.4(14) . . . . ?
C32 N5 C24 C25 37.1(14) . . . . ?
C35 N5 C24 C25 -129.1(10) . . . . ?
C32 N5 C24 C23 -141.1(9) . . . . ?
C35 N5 C24 C23 52.7(13) . . . . ?
F2 C23 C24 N5 2.9(12) . . . . ?
C22 C23 C24 N5 -179.4(8) . . . . ?
F2 C23 C24 C25 -175.4(7) . . . . ?
C22 C23 C24 C25 2.2(13) . . . . ?
C29 O8 C25 C24 -164.3(7) . . . . ?
C29 O8 C25 C26 18.2(12) . . . . ?
N5 C24 C25 O8 1.7(13) . . . . ?
C23 C24 C25 O8 179.9(8) . . . . ?
N5 C24 C25 C26 179.1(8) . . . . ?
C23 C24 C25 C26 -2.7(13) . . . . ?
C19 N4 C26 C25 -172.7(8) . . . . ?
C30 N4 C26 C25 11.7(12) . . . . ?
C19 N4 C26 C27 9.8(13) . . . . ?
C30 N4 C26 C27 -165.8(8) . . . . ?
O8 C25 C26 N4 2.2(13) . . . . ?
C24 C25 C26 N4 -175.1(8) . . . . ?
O8 C25 C26 C27 179.7(8) . . . . ?
C24 C25 C26 C27 2.4(13) . . . . ?
C23 C22 C27 C26 1.0(13) . . . . ?
C23 C22 C27 C21 -176.2(7) . . . . ?
N4 C26 C27 C22 176.0(8) . . . . ?
C25 C26 C27 C22 -1.5(13) . . . . ?
N4 C26 C27 C21 -6.7(12) . . . . ?
C25 C26 C27 C21 175.8(7) . . . . ?
O7 C21 C27 C22 -3.7(13) . . . . ?
C20 C21 C27 C22 175.4(8) . . . . ?
O7 C21 C27 C26 179.0(8) . . . . ?
C20 C21 C27 C26 -1.8(12) . . . . ?
C19 C20 C28 O5 0.5(15) . . . . ?
C21 C20 C28 O5 -178.8(10) . . . . ?
C19 C20 C28 O6 179.8(9) . . . . ?
C21 C20 C28 O6 0.5(13) . . . . ?
C25 O8 C29 C30 -50.9(10) . . . . ?
C19 N4 C30 C31 17.5(12) . . . . ?
C26 N4 C30 C31 -167.0(8) . . . . ?
C19 N4 C30 C29 142.4(9) . . . . ?
C26 N4 C30 C29 -42.1(11) . . . . ?
O8 C29 C30 N4 61.8(10) . . . . ?
O8 C29 C30 C31 -173.9(7) . . . . ?
C24 N5 C32 C33 -114.5(11) . . . . ?
C35 N5 C32 C33 52.7(13) . . . . ?
C36 N6 C33 C32 -177.1(8) . . . . ?
C34 N6 C33 C32 62.4(10) . . . . ?
N5 C32 C33 N6 -57.4(12) . . . . ?
C36 N6 C34 C35 175.9(12) . . . . ?
C33 N6 C34 C35 -63.5(12) . . . . ?
C24 N5 C35 C34 116.3(9) . . . . ?
C32 N5 C35 C34 -51.3(11) . . . . ?
N6 C34 C35 N5 56.6(13) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.76 2.521(12) 154.4 . yes
O6 H6 O7 0.82 1.78 2.550(13) 154.8 . yes
O10 H10B N6 0.81 2.05 2.814(12) 156.8 3_445 yes
O9 H9A N3 0.81 2.61 2.821(12) 96.7 . yes
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.087
_cell_measurement_pressure       2.99


# start Validation Reply Form
_vrf_ATOM007_LH_PE_2p99          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_PE_2p99          
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_PE_2p99          
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_PE_2p99          
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_PE_2p99          
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_PE_2p99          
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_PE_2p99          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_PE_2p99          
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_PE_2p99          
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_2p99          
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT111_LH_PE_2p99          
;
RESPONSE: The structure is chiral.

;
_vrf_PLAT721_LH_PE_2p99          
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints

;
_vrf_PLAT910_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_PE_2p99          
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_PE_2p99          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_PE_2p99          
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_PE_2p99          
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_OFLO_3p0
_database_code_depnum_ccdc_archive 'CCDC 2481345'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_240522_run2_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   28.803(7)
_cell_length_b                   6.1832(5)
_cell_length_c                   16.0548(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.372(15)
_cell_angle_gamma                90
_cell_volume                     2781.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5369
_cell_measurement_theta_min      2.608
_cell_measurement_theta_max      23.288
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6814
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            5369
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.608
_diffrn_reflns_theta_max         23.288
_diffrn_reflns_theta_full        23.288
_diffrn_measured_fraction_theta_max 0.345
_diffrn_measured_fraction_theta_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.345
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.345
_diffrn_reflns_point_group_measured_fraction_full 0.344
_reflns_number_total             692
_reflns_number_gt                497
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0216P)²+7.5930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         692
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      0.902
_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
F1 F 0.5701(3) 0.7033(5) 0.78855(18) 0.023(5) Uani 1 1 d D . . . .
O1 O 0.6481(4) 0.5935(6) 0.5665(3) 0.034(5) Uani 1 1 d D . . . .
O4 O 0.4350(4) 0.8090(5) 0.2679(2) 0.024(6) Uani 1 1 d D . . . .
C11 C 0.5235(5) 0.7290(9) 0.5598(4) 0.027(4) Uani 1 1 d D . . . .
O2 O 0.4422(4) 0.8235(6) 0.5247(3) 0.030(5) Uani 1 1 d D . . . .
N3 N 0.5641(5) 0.6859(7) 0.4450(3) 0.023(4) Uani 1 1 d D . . . .
N1 N 0.6512(5) 0.6090(7) 0.7439(3) 0.025(4) Uani 1 1 d D . . . .
C7 C 0.5677(6) 0.6929(9) 0.7025(4) 0.019(4) Uani 1 1 d D . . . .
C10 C 0.5646(5) 0.6802(9) 0.5325(4) 0.025(4) Uani 1 1 d D . . . .
C3 C 0.5231(6) 0.7306(10) 0.3893(4) 0.023(4) Uani 1 1 d D . . . .
H3 H 0.523182 0.733361 0.331438 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6097(6) 0.6396(9) 0.6792(4) 0.022(4) Uani 1 1 d D . . . .
O3 O 0.3994(4) 0.8699(6) 0.3735(3) 0.031(5) Uani 1 1 d D . . . .
H3A H 0.406345 0.867924 0.425953 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4812(6) 0.7725(9) 0.4116(4) 0.022(4) Uani 1 1 d D . . . .
C6 C 0.5254(5) 0.7354(9) 0.6485(4) 0.023(5) Uani 1 1 d D . . . .
H6 H 0.498468 0.767723 0.668915 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6062(5) 0.6363(10) 0.5911(4) 0.027(4) Uani 1 1 d D . . . .
N2 N 0.7466(4) 0.5993(7) 0.8414(3) 0.027(5) Uani 1 1 d D . . . .
C13 C 0.4370(5) 0.8168(9) 0.3448(4) 0.024(5) Uani 1 1 d D . . . .
C16 C 0.7144(4) 0.7790(8) 0.8501(3) 0.027(5) Uani 1 1 d D . . . .
H16A H 0.732944 0.910575 0.864056 0.032 Uiso 1 1 calc R U . . .
H16B H 0.699299 0.748213 0.896906 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4784(5) 0.7758(9) 0.4994(4) 0.025(4) Uani 1 1 d D . . . .
C1 C 0.6423(5) 0.5222(8) 0.4788(3) 0.034(6) Uani 1 1 d D . . . .
H1A H 0.628574 0.378152 0.472234 0.040 Uiso 1 1 calc R U . . .
H1B H 0.673180 0.516139 0.464414 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6310(6) 0.9000(8) 0.4207(4) 0.027(7) Uani 1 1 d D . . . .
H12A H 0.609380 0.991341 0.381572 0.040 Uiso 1 1 calc R U . . .
H12B H 0.660914 0.892704 0.404001 0.040 Uiso 1 1 calc R U . . .
H12C H 0.636120 0.958498 0.477498 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6101(6) 0.6763(9) 0.4193(4) 0.028(5) Uani 1 1 d D . . . .
H2 H 0.604500 0.619380 0.360810 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6766(4) 0.8134(8) 0.7693(3) 0.024(5) Uani 1 1 d D . . . .
H17A H 0.654244 0.922968 0.778693 0.029 Uiso 1 1 calc R U . . .
H17B H 0.691174 0.863153 0.724008 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7196(5) 0.4013(8) 0.8171(3) 0.027(5) Uani 1 1 d D . . . .
H15A H 0.703327 0.361452 0.861456 0.032 Uiso 1 1 calc R U . . .
H15B H 0.741151 0.284905 0.811217 0.032 Uiso 1 1 calc R U . . .
C18 C 0.7827(5) 0.5658(10) 0.9205(3) 0.038(6) Uani 1 1 d D . . . .
H18A H 0.801912 0.693637 0.933655 0.057 Uiso 1 1 calc R U . . .
H18B H 0.802583 0.445689 0.913576 0.057 Uiso 1 1 calc R U . . .
H18C H 0.767372 0.536035 0.966397 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6834(4) 0.4333(8) 0.7335(3) 0.029(5) Uani 1 1 d D . . . .
H14A H 0.699577 0.469055 0.688532 0.034 Uiso 1 1 calc R U . . .
H14B H 0.665436 0.301106 0.717532 0.034 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 C7 1.369(6) . ?
O1 C9 1.378(14) . ?
O1 C1 1.449(6) . ?
O4 C13 1.223(6) . ?
C11 C10 1.390(13) . ?
C11 C6 1.413(7) . ?
C11 C5 1.459(11) . ?
O2 C5 1.238(13) . ?
N3 C3 1.335(15) . ?
N3 C10 1.401(7) . ?
N3 C2 1.479(16) . ?
N1 C8 1.404(16) . ?
N1 C14 1.463(11) . ?
N1 C17 1.469(10) . ?
C7 C6 1.349(15) . ?
C7 C8 1.386(17) . ?
C10 C9 1.368(15) . ?
C3 C4 1.361(17) . ?
C3 H3 0.9300 . ?
C8 C9 1.395(8) . ?
O3 C13 1.311(15) . ?
O3 H3A 0.8200 . ?
C4 C5 1.430(8) . ?
C4 C13 1.488(14) . ?
C6 H6 0.9300 . ?
N2 C15 1.454(10) . ?
N2 C18 1.459(9) . ?
N2 C16 1.474(11) . ?
C16 C17 1.504(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.506(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.507(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.509(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 115.1(9) . . ?
C10 C11 C6 119.2(10) . . ?
C10 C11 C5 121.8(6) . . ?
C6 C11 C5 119.1(9) . . ?
C3 N3 C10 118.7(11) . . ?
C3 N3 C2 122.2(6) . . ?
C10 N3 C2 118.4(11) . . ?
C8 N1 C14 118.0(6) . . ?
C8 N1 C17 111.9(6) . . ?
C14 N1 C17 112.5(9) . . ?
C6 C7 F1 117.7(10) . . ?
C6 C7 C8 126.1(7) . . ?
F1 C7 C8 116.2(11) . . ?
C9 C10 C11 120.1(6) . . ?
C9 C10 N3 120.0(11) . . ?
C11 C10 N3 119.9(11) . . ?
N3 C3 C4 124.3(7) . . ?
N3 C3 H3 117.8 . . ?
C4 C3 H3 117.8 . . ?
C7 C8 C9 114.5(12) . . ?
C7 C8 N1 118.6(6) . . ?
C9 C8 N1 126.8(12) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 121.1(12) . . ?
C3 C4 C13 120.6(6) . . ?
C5 C4 C13 118.3(11) . . ?
C7 C6 C11 117.4(11) . . ?
C7 C6 H6 121.3 . . ?
C11 C6 H6 121.3 . . ?
C10 C9 O1 121.7(6) . . ?
C10 C9 C8 122.8(11) . . ?
O1 C9 C8 115.4(11) . . ?
C15 N2 C18 110.1(5) . . ?
C15 N2 C16 110.6(9) . . ?
C18 N2 C16 111.2(5) . . ?
O4 C13 O3 120.9(12) . . ?
O4 C13 C4 123.6(11) . . ?
O3 C13 C4 115.5(6) . . ?
N2 C16 C17 111.7(5) . . ?
N2 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N2 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
O2 C5 C4 124.8(11) . . ?
O2 C5 C11 121.1(7) . . ?
C4 C5 C11 114.1(10) . . ?
O1 C1 C2 109.9(6) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C1 107.9(7) . . ?
N3 C2 C12 109.9(8) . . ?
C1 C2 C12 112.7(11) . . ?
N3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C12 C2 H2 108.8 . . ?
N1 C17 C16 109.4(5) . . ?
N1 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N1 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
N2 C15 C14 110.1(5) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 108.7(5) . . ?
N1 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
N1 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.3 . . ?
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
C6 C11 C10 C9 0.9(10) . . . . ?
C5 C11 C10 C9 -179.7(7) . . . . ?
C6 C11 C10 N3 -176.2(6) . . . . ?
C5 C11 C10 N3 3.3(9) . . . . ?
C3 N3 C10 C9 -179.5(7) . . . . ?
C2 N3 C10 C9 -9.0(9) . . . . ?
C3 N3 C10 C11 -2.5(10) . . . . ?
C2 N3 C10 C11 168.0(6) . . . . ?
C10 N3 C3 C4 0.2(11) . . . . ?
C2 N3 C3 C4 -169.9(6) . . . . ?
C6 C7 C8 C9 1.4(11) . . . . ?
F1 C7 C8 C9 -178.4(5) . . . . ?
C6 C7 C8 N1 177.4(7) . . . . ?
F1 C7 C8 N1 -2.4(9) . . . . ?
C14 N1 C8 C7 140.6(7) . . . . ?
C17 N1 C8 C7 -86.6(8) . . . . ?
C14 N1 C8 C9 -44.0(10) . . . . ?
C17 N1 C8 C9 88.9(8) . . . . ?
N3 C3 C4 C5 1.3(12) . . . . ?
N3 C3 C4 C13 -178.8(7) . . . . ?
F1 C7 C6 C11 178.7(5) . . . . ?
C8 C7 C6 C11 -1.1(11) . . . . ?
C10 C11 C6 C7 -0.1(10) . . . . ?
C5 C11 C6 C7 -179.5(6) . . . . ?
C11 C10 C9 O1 -178.1(6) . . . . ?
N3 C10 C9 O1 -1.0(10) . . . . ?
C11 C10 C9 C8 -0.6(11) . . . . ?
N3 C10 C9 C8 176.5(5) . . . . ?
C1 O1 C9 C10 -21.2(9) . . . . ?
C1 O1 C9 C8 161.1(5) . . . . ?
C7 C8 C9 C10 -0.5(10) . . . . ?
N1 C8 C9 C10 -176.1(6) . . . . ?
C7 C8 C9 O1 177.1(6) . . . . ?
N1 C8 C9 O1 1.5(10) . . . . ?
C3 C4 C13 O4 3.4(10) . . . . ?
C5 C4 C13 O4 -176.8(6) . . . . ?
C3 C4 C13 O3 -175.4(7) . . . . ?
C5 C4 C13 O3 4.4(9) . . . . ?
C15 N2 C16 C17 -56.7(6) . . . . ?
C18 N2 C16 C17 -179.3(6) . . . . ?
C3 C4 C5 O2 176.1(7) . . . . ?
C13 C4 C5 O2 -3.8(10) . . . . ?
C3 C4 C5 C11 -0.6(10) . . . . ?
C13 C4 C5 C11 179.6(5) . . . . ?
C10 C11 C5 O2 -178.5(7) . . . . ?
C6 C11 C5 O2 1.0(9) . . . . ?
C10 C11 C5 C4 -1.7(9) . . . . ?
C6 C11 C5 C4 177.8(5) . . . . ?
C9 O1 C1 C2 51.1(10) . . . . ?
C3 N3 C2 C1 -152.0(6) . . . . ?
C10 N3 C2 C1 37.8(7) . . . . ?
C3 N3 C2 C12 84.8(9) . . . . ?
C10 N3 C2 C12 -85.4(8) . . . . ?
O1 C1 C2 N3 -57.6(10) . . . . ?
O1 C1 C2 C12 63.9(12) . . . . ?
C8 N1 C17 C16 168.3(7) . . . . ?
C14 N1 C17 C16 -56.2(7) . . . . ?
N2 C16 C17 N1 54.0(9) . . . . ?
C18 N2 C15 C14 -177.8(7) . . . . ?
C16 N2 C15 C14 58.9(7) . . . . ?
C8 N1 C14 C15 -168.6(7) . . . . ?
C17 N1 C14 C15 58.9(7) . . . . ?
N2 C15 C14 N1 -59.4(9) . . . . ?
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.029
_cell_measurement_pressure       3.0


# start Validation Reply Form
_vrf_ATOM007_OFLO_3p0            
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_3p0            
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_3p0            
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_3p0            
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_3p0            
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_3p0            
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_3p0            
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_3p0            
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_3p0            
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_3p0            
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_3p0            
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_3p0            
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_3p0            
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_OFLO_1p81
_database_code_depnum_ccdc_archive 'CCDC 2481342'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_070522_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   29.123(7)
_cell_length_b                   6.3326(6)
_cell_length_c                   16.2627(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.781(17)
_cell_angle_gamma                90
_cell_volume                     2912.9(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5261
_cell_measurement_theta_min      2.579
_cell_measurement_theta_max      23.338
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6653
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            5261
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.579
_diffrn_reflns_theta_max         23.338
_diffrn_reflns_theta_full        23.338
_diffrn_measured_fraction_theta_max 0.349
_diffrn_measured_fraction_theta_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.349
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.349
_diffrn_reflns_point_group_measured_fraction_full 0.349
_reflns_number_total             737
_reflns_number_gt                490
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²+1.4703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         737
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      0.945
_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
F1 F 0.5701(3) 0.7044(5) 0.7853(2) 0.049(5) Uani 1 1 d D . . . .
O1 O 0.6477(4) 0.6034(7) 0.5659(3) 0.040(5) Uani 1 1 d D . . . .
O4 O 0.4366(4) 0.8041(6) 0.2698(3) 0.033(7) Uani 1 1 d D . . . .
C11 C 0.5238(5) 0.7303(9) 0.5590(4) 0.022(4) Uani 1 1 d D . . . .
O2 O 0.4428(4) 0.8210(7) 0.5233(3) 0.033(5) Uani 1 1 d D . . . .
N3 N 0.5630(5) 0.6881(8) 0.4453(4) 0.029(5) Uani 1 1 d D . . . .
N1 N 0.6512(5) 0.6138(8) 0.7425(4) 0.025(5) Uani 1 1 d D . . . .
C7 C 0.5682(6) 0.6960(11) 0.7006(5) 0.020(5) Uani 1 1 d D . . . .
C10 C 0.5644(5) 0.6838(9) 0.5323(4) 0.022(4) Uani 1 1 d D . . . .
C3 C 0.5221(6) 0.7318(11) 0.3899(5) 0.027(5) Uani 1 1 d D . . . .
H3 H 0.521965 0.733639 0.332613 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6104(6) 0.6472(10) 0.6785(5) 0.021(4) Uani 1 1 d D . . . .
O3 O 0.4004(5) 0.8652(7) 0.3714(3) 0.042(5) Uani 1 1 d D . . . .
H3A H 0.405660 0.847658 0.422798 0.063 Uiso 1 1 calc R U . . .
C4 C 0.4816(6) 0.7730(11) 0.4116(4) 0.025(5) Uani 1 1 d D . . . .
C6 C 0.5252(6) 0.7348(10) 0.6463(4) 0.025(5) Uani 1 1 d D . . . .
H6 H 0.498355 0.762529 0.665995 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6067(5) 0.6406(11) 0.5899(4) 0.027(5) Uani 1 1 d D . . . .
N2 N 0.7448(4) 0.6060(8) 0.8401(3) 0.032(5) Uani 1 1 d D . . . .
C13 C 0.4382(6) 0.8140(10) 0.3449(5) 0.030(5) Uani 1 1 d D . . . .
C16 C 0.7127(5) 0.7787(10) 0.8493(4) 0.031(6) Uani 1 1 d D . . . .
H16A H 0.730820 0.907299 0.864765 0.038 Uiso 1 1 calc R U . . .
H16B H 0.697379 0.744959 0.894487 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4787(5) 0.7760(10) 0.4987(4) 0.025(5) Uani 1 1 d D . . . .
C1 C 0.6413(5) 0.5282(9) 0.4792(3) 0.040(6) Uani 1 1 d D . . . .
H1A H 0.627573 0.387808 0.474005 0.048 Uiso 1 1 calc R U . . .
H1B H 0.671604 0.520829 0.464504 0.048 Uiso 1 1 calc R U . . .
C12 C 0.6303(7) 0.8964(9) 0.4208(4) 0.042(8) Uani 1 1 d D . . . .
H12A H 0.609960 0.982618 0.378882 0.063 Uiso 1 1 calc R U . . .
H12B H 0.660786 0.885826 0.408148 0.063 Uiso 1 1 calc R U . . .
H12C H 0.633654 0.959033 0.475649 0.063 Uiso 1 1 calc R U . . .
C2 C 0.6090(6) 0.6778(9) 0.4203(4) 0.030(5) Uani 1 1 d D . . . .
H2 H 0.603264 0.621063 0.362677 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6758(5) 0.8144(9) 0.7686(4) 0.028(6) Uani 1 1 d D . . . .
H17A H 0.653405 0.920296 0.777477 0.034 Uiso 1 1 calc R U . . .
H17B H 0.690580 0.864479 0.724776 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7180(5) 0.4129(9) 0.8150(3) 0.025(5) Uani 1 1 d D . . . .
H15A H 0.701625 0.373810 0.858168 0.030 Uiso 1 1 calc R U . . .
H15B H 0.739465 0.299163 0.809907 0.030 Uiso 1 1 calc R U . . .
C18 C 0.7810(5) 0.5747(12) 0.9181(4) 0.047(6) Uani 1 1 d D . . . .
H18A H 0.797358 0.705204 0.934521 0.070 Uiso 1 1 calc R U . . .
H18B H 0.802997 0.469454 0.909195 0.070 Uiso 1 1 calc R U . . .
H18C H 0.766357 0.528774 0.962104 0.070 Uiso 1 1 calc R U . . .
C14 C 0.6827(5) 0.4430(10) 0.7319(4) 0.028(5) Uani 1 1 d D . . . .
H14A H 0.698788 0.478339 0.687922 0.033 Uiso 1 1 calc R U . . .
H14B H 0.664822 0.314086 0.715728 0.033 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 C7 1.366(7) . ?
O1 C9 1.361(14) . ?
O1 C1 1.457(6) . ?
O4 C13 1.213(7) . ?
C11 C10 1.388(13) . ?
C11 C6 1.409(8) . ?
C11 C5 1.469(11) . ?
O2 C5 1.236(14) . ?
N3 C3 1.340(16) . ?
N3 C10 1.407(8) . ?
N3 C2 1.490(16) . ?
N1 C8 1.396(17) . ?
N1 C14 1.455(12) . ?
N1 C17 1.471(10) . ?
C7 C6 1.373(16) . ?
C7 C8 1.393(18) . ?
C10 C9 1.385(15) . ?
C3 C4 1.337(18) . ?
C3 H3 0.9300 . ?
C8 C9 1.420(9) . ?
O3 C13 1.315(16) . ?
O3 H3A 0.8200 . ?
C4 C5 1.439(9) . ?
C4 C13 1.479(15) . ?
C6 H6 0.9300 . ?
N2 C15 1.456(11) . ?
N2 C18 1.456(10) . ?
N2 C16 1.469(12) . ?
C16 C17 1.502(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.506(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.516(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.503(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 114.4(10) . . ?
C10 C11 C6 119.8(11) . . ?
C10 C11 C5 121.8(6) . . ?
C6 C11 C5 118.4(10) . . ?
C3 N3 C10 119.3(11) . . ?
C3 N3 C2 122.5(6) . . ?
C10 N3 C2 117.5(11) . . ?
C8 N1 C14 118.2(6) . . ?
C8 N1 C17 110.8(7) . . ?
C14 N1 C17 113.5(10) . . ?
F1 C7 C6 116.9(11) . . ?
F1 C7 C8 116.3(12) . . ?
C6 C7 C8 126.8(7) . . ?
C9 C10 C11 121.3(6) . . ?
C9 C10 N3 119.4(11) . . ?
C11 C10 N3 119.3(11) . . ?
C4 C3 N3 124.2(7) . . ?
C4 C3 H3 117.9 . . ?
N3 C3 H3 117.9 . . ?
C7 C8 N1 119.1(7) . . ?
C7 C8 C9 114.3(12) . . ?
N1 C8 C9 126.6(12) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 121.7(12) . . ?
C3 C4 C13 119.6(7) . . ?
C5 C4 C13 118.7(12) . . ?
C7 C6 C11 116.6(11) . . ?
C7 C6 H6 121.7 . . ?
C11 C6 H6 121.7 . . ?
O1 C9 C10 122.7(6) . . ?
O1 C9 C8 115.9(12) . . ?
C10 C9 C8 121.2(11) . . ?
C15 N2 C18 111.0(6) . . ?
C15 N2 C16 110.0(10) . . ?
C18 N2 C16 111.0(6) . . ?
O4 C13 O3 120.7(13) . . ?
O4 C13 C4 123.4(12) . . ?
O3 C13 C4 115.9(7) . . ?
N2 C16 C17 111.3(6) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O2 C5 C4 125.0(12) . . ?
O2 C5 C11 121.3(7) . . ?
C4 C5 C11 113.7(11) . . ?
O1 C1 C2 109.1(6) . . ?
O1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C1 108.6(7) . . ?
N3 C2 C12 110.6(9) . . ?
C1 C2 C12 112.2(12) . . ?
N3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C12 C2 H2 108.5 . . ?
N1 C17 C16 108.8(6) . . ?
N1 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
N1 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
N2 C15 C14 110.6(6) . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 107.7(6) . . ?
N1 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
N1 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
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
C6 C11 C10 C9 0.2(10) . . . . ?
C5 C11 C10 C9 -179.9(7) . . . . ?
C6 C11 C10 N3 -177.5(6) . . . . ?
C5 C11 C10 N3 2.4(10) . . . . ?
C3 N3 C10 C9 -179.4(7) . . . . ?
C2 N3 C10 C9 -9.1(10) . . . . ?
C3 N3 C10 C11 -1.7(11) . . . . ?
C2 N3 C10 C11 168.7(6) . . . . ?
C10 N3 C3 C4 0.1(12) . . . . ?
C2 N3 C3 C4 -169.7(7) . . . . ?
F1 C7 C8 N1 -1.0(11) . . . . ?
C6 C7 C8 N1 179.5(8) . . . . ?
F1 C7 C8 C9 -179.9(5) . . . . ?
C6 C7 C8 C9 0.6(12) . . . . ?
C14 N1 C8 C7 139.4(8) . . . . ?
C17 N1 C8 C7 -87.2(9) . . . . ?
C14 N1 C8 C9 -41.8(12) . . . . ?
C17 N1 C8 C9 91.6(9) . . . . ?
N3 C3 C4 C5 0.7(13) . . . . ?
N3 C3 C4 C13 -178.5(8) . . . . ?
F1 C7 C6 C11 178.7(5) . . . . ?
C8 C7 C6 C11 -1.9(13) . . . . ?
C10 C11 C6 C7 1.4(10) . . . . ?
C5 C11 C6 C7 -178.5(7) . . . . ?
C1 O1 C9 C10 -23.7(10) . . . . ?
C1 O1 C9 C8 160.5(5) . . . . ?
C11 C10 C9 O1 -177.1(6) . . . . ?
N3 C10 C9 O1 0.6(11) . . . . ?
C11 C10 C9 C8 -1.5(11) . . . . ?
N3 C10 C9 C8 176.2(6) . . . . ?
C7 C8 C9 O1 177.0(7) . . . . ?
N1 C8 C9 O1 -1.9(11) . . . . ?
C7 C8 C9 C10 1.1(11) . . . . ?
N1 C8 C9 C10 -177.7(7) . . . . ?
C3 C4 C13 O4 3.1(11) . . . . ?
C5 C4 C13 O4 -176.1(6) . . . . ?
C3 C4 C13 O3 -176.2(7) . . . . ?
C5 C4 C13 O3 4.6(10) . . . . ?
C15 N2 C16 C17 -57.7(7) . . . . ?
C18 N2 C16 C17 179.0(7) . . . . ?
C3 C4 C5 O2 177.0(8) . . . . ?
C13 C4 C5 O2 -3.8(12) . . . . ?
C3 C4 C5 C11 0.0(11) . . . . ?
C13 C4 C5 C11 179.2(6) . . . . ?
C10 C11 C5 O2 -178.7(7) . . . . ?
C6 C11 C5 O2 1.2(11) . . . . ?
C10 C11 C5 C4 -1.6(10) . . . . ?
C6 C11 C5 C4 178.3(6) . . . . ?
C9 O1 C1 C2 52.9(10) . . . . ?
C3 N3 C2 C1 -152.1(7) . . . . ?
C10 N3 C2 C1 37.9(8) . . . . ?
C3 N3 C2 C12 84.4(10) . . . . ?
C10 N3 C2 C12 -85.6(8) . . . . ?
O1 C1 C2 N3 -58.7(10) . . . . ?
O1 C1 C2 C12 63.8(12) . . . . ?
C8 N1 C17 C16 167.5(8) . . . . ?
C14 N1 C17 C16 -56.7(7) . . . . ?
N2 C16 C17 N1 54.6(9) . . . . ?
C18 N2 C15 C14 -176.7(7) . . . . ?
C16 N2 C15 C14 60.0(7) . . . . ?
C8 N1 C14 C15 -169.0(8) . . . . ?
C17 N1 C14 C15 58.7(7) . . . . ?
N2 C15 C14 N1 -59.4(9) . . . . ?
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.040
_cell_measurement_pressure       1.81


# start Validation Reply Form
_vrf_ATOM007_OFLO_1p81           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_1p81           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_1p81           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_1p81           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_1p81           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_1p81           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_1p81           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_1p81           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_1p81           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_1p81           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_1p81           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_1p81           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_1p81           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_OFLO-2p16
_database_code_depnum_ccdc_archive 'CCDC 2481343'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_200522_run1_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   29.051(7)
_cell_length_b                   6.2990(6)
_cell_length_c                   16.2226(17)
_cell_angle_alpha                90
_cell_angle_beta                 103.694(16)
_cell_angle_gamma                90
_cell_volume                     2884.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4013
_cell_measurement_theta_min      2.585
_cell_measurement_theta_max      23.303
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6771
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            4013
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_max         23.303
_diffrn_reflns_theta_full        23.303
_diffrn_measured_fraction_theta_max 0.346
_diffrn_measured_fraction_theta_full 0.346
_diffrn_reflns_Laue_measured_fraction_max 0.346
_diffrn_reflns_Laue_measured_fraction_full 0.346
_diffrn_reflns_point_group_measured_fraction_max 0.346
_diffrn_reflns_point_group_measured_fraction_full 0.346
_reflns_number_total             719
_reflns_number_gt                486
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0649P)²+1.7593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         719
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      0.930
_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
F1 F 0.5703(3) 0.7032(5) 0.7864(2) 0.047(5) Uani 1 1 d D . . . .
O1 O 0.6476(4) 0.6016(7) 0.5660(3) 0.039(5) Uani 1 1 d D . . . .
O4 O 0.4363(4) 0.8064(6) 0.2692(3) 0.032(7) Uani 1 1 d D . . . .
C11 C 0.5240(5) 0.7297(9) 0.5591(4) 0.024(5) Uani 1 1 d D . . . .
O2 O 0.4430(4) 0.8217(7) 0.5236(3) 0.031(5) Uani 1 1 d D . . . .
N3 N 0.5629(5) 0.6873(8) 0.4454(4) 0.024(5) Uani 1 1 d D . . . .
N1 N 0.6503(5) 0.6131(8) 0.7421(4) 0.027(5) Uani 1 1 d D . . . .
C7 C 0.5685(6) 0.6936(11) 0.7017(5) 0.025(5) Uani 1 1 d D . . . .
C10 C 0.5644(5) 0.6821(9) 0.5324(4) 0.023(4) Uani 1 1 d D . . . .
C3 C 0.5219(6) 0.7308(11) 0.3895(5) 0.023(5) Uani 1 1 d D . . . .
H3 H 0.521973 0.733418 0.332193 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6096(6) 0.6462(10) 0.6777(5) 0.026(4) Uani 1 1 d D . . . .
O3 O 0.4000(5) 0.8662(7) 0.3722(3) 0.040(5) Uani 1 1 d D . . . .
H3A H 0.406532 0.860496 0.424132 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4804(6) 0.7712(10) 0.4113(5) 0.025(5) Uani 1 1 d D . . . .
C6 C 0.5259(6) 0.7355(10) 0.6472(4) 0.026(5) Uani 1 1 d D . . . .
H6 H 0.499193 0.766700 0.667064 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6062(5) 0.6384(11) 0.5905(5) 0.028(5) Uani 1 1 d D . . . .
N2 N 0.7456(4) 0.6049(8) 0.8405(3) 0.036(5) Uani 1 1 d D . . . .
C13 C 0.4371(6) 0.8163(10) 0.3447(5) 0.027(5) Uani 1 1 d D . . . .
C16 C 0.7138(5) 0.7799(10) 0.8500(4) 0.037(6) Uani 1 1 d D . . . .
H16A H 0.732077 0.908901 0.864893 0.045 Uiso 1 1 calc R U . . .
H16B H 0.698553 0.747241 0.895661 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4788(5) 0.7763(10) 0.4991(5) 0.023(5) Uani 1 1 d D . . . .
C1 C 0.6415(6) 0.5272(9) 0.4792(4) 0.034(6) Uani 1 1 d D . . . .
H1A H 0.627668 0.386132 0.473589 0.040 Uiso 1 1 calc R U . . .
H1B H 0.671995 0.519554 0.464833 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6305(6) 0.8966(9) 0.4208(4) 0.033(7) Uani 1 1 d D . . . .
H12A H 0.608746 0.986898 0.382536 0.050 Uiso 1 1 calc R U . . .
H12B H 0.659751 0.888415 0.403205 0.050 Uiso 1 1 calc R U . . .
H12C H 0.636340 0.954048 0.477124 0.050 Uiso 1 1 calc R U . . .
C2 C 0.6095(6) 0.6779(9) 0.4200(4) 0.029(5) Uani 1 1 d D . . . .
H2 H 0.603855 0.621049 0.362197 0.035 Uiso 1 1 calc R U . . .
C17 C 0.6766(5) 0.8147(8) 0.7692(4) 0.035(6) Uani 1 1 d D . . . .
H17A H 0.654612 0.923472 0.778032 0.042 Uiso 1 1 calc R U . . .
H17B H 0.691472 0.863035 0.725000 0.042 Uiso 1 1 calc R U . . .
C15 C 0.7183(5) 0.4105(9) 0.8156(3) 0.033(6) Uani 1 1 d D . . . .
H15A H 0.701956 0.372180 0.859140 0.039 Uiso 1 1 calc R U . . .
H15B H 0.739620 0.295377 0.810397 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7815(5) 0.5732(12) 0.9191(4) 0.049(6) Uani 1 1 d D . . . .
H18A H 0.800413 0.699179 0.932098 0.074 Uiso 1 1 calc R U . . .
H18B H 0.801355 0.455694 0.912559 0.074 Uiso 1 1 calc R U . . .
H18C H 0.766315 0.543943 0.964393 0.074 Uiso 1 1 calc R U . . .
C14 C 0.6827(5) 0.4413(9) 0.7322(4) 0.030(5) Uani 1 1 d D . . . .
H14A H 0.698819 0.477520 0.688169 0.036 Uiso 1 1 calc R U . . .
H14B H 0.665006 0.311181 0.715903 0.036 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 C7 1.365(7) . ?
O1 C9 1.373(14) . ?
O1 C1 1.454(6) . ?
O4 C13 1.220(7) . ?
C11 C10 1.379(13) . ?
C11 C6 1.416(8) . ?
C11 C5 1.467(11) . ?
O2 C5 1.231(14) . ?
N3 C3 1.343(16) . ?
N3 C10 1.401(8) . ?
N3 C2 1.507(16) . ?
N1 C8 1.395(16) . ?
N1 C14 1.467(12) . ?
N1 C17 1.493(10) . ?
C7 C6 1.364(16) . ?
C7 C8 1.376(18) . ?
C10 C9 1.377(15) . ?
C3 C4 1.358(18) . ?
C3 H3 0.9300 . ?
C8 C9 1.395(10) . ?
O3 C13 1.299(16) . ?
O3 H3A 0.8200 . ?
C4 C5 1.437(10) . ?
C4 C13 1.479(15) . ?
C6 H6 0.9300 . ?
N2 C18 1.457(10) . ?
N2 C15 1.462(11) . ?
N2 C16 1.470(12) . ?
C16 C17 1.505(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.505(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.506(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.509(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 114.8(10) . . ?
C10 C11 C6 119.3(11) . . ?
C10 C11 C5 122.0(7) . . ?
C6 C11 C5 118.7(10) . . ?
C3 N3 C10 119.8(11) . . ?
C3 N3 C2 122.2(7) . . ?
C10 N3 C2 117.3(11) . . ?
C8 N1 C14 118.6(6) . . ?
C8 N1 C17 112.1(7) . . ?
C14 N1 C17 111.3(10) . . ?
C6 C7 F1 117.3(11) . . ?
C6 C7 C8 125.0(8) . . ?
F1 C7 C8 117.7(12) . . ?
C9 C10 C11 120.4(7) . . ?
C9 C10 N3 120.5(11) . . ?
C11 C10 N3 119.1(11) . . ?
N3 C3 C4 124.2(7) . . ?
N3 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C7 C8 C9 115.8(13) . . ?
C7 C8 N1 117.3(7) . . ?
C9 C8 N1 126.8(13) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.1(12) . . ?
C3 C4 C13 120.0(7) . . ?
C5 C4 C13 119.9(12) . . ?
C7 C6 C11 117.6(11) . . ?
C7 C6 H6 121.2 . . ?
C11 C6 H6 121.2 . . ?
O1 C9 C10 121.7(7) . . ?
O1 C9 C8 116.2(12) . . ?
C10 C9 C8 121.9(12) . . ?
C18 N2 C15 110.8(6) . . ?
C18 N2 C16 110.4(6) . . ?
C15 N2 C16 110.1(10) . . ?
O4 C13 O3 122.5(13) . . ?
O4 C13 C4 122.2(12) . . ?
O3 C13 C4 115.3(8) . . ?
N2 C16 C17 110.9(6) . . ?
N2 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
O2 C5 C4 123.6(12) . . ?
O2 C5 C11 121.6(8) . . ?
C4 C5 C11 114.8(11) . . ?
O1 C1 C2 109.3(7) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C2 C12 112.6(11) . . ?
C1 C2 N3 108.0(7) . . ?
C12 C2 N3 110.5(9) . . ?
C1 C2 H2 108.6 . . ?
C12 C2 H2 108.6 . . ?
N3 C2 H2 108.6 . . ?
N1 C17 C16 110.1(6) . . ?
N1 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N2 C15 C14 110.6(6) . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 108.6(6) . . ?
N1 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
N1 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
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
C6 C11 C10 C9 0.7(10) . . . . ?
C5 C11 C10 C9 -179.8(7) . . . . ?
C6 C11 C10 N3 -176.7(6) . . . . ?
C5 C11 C10 N3 2.8(10) . . . . ?
C3 N3 C10 C9 -179.8(7) . . . . ?
C2 N3 C10 C9 -9.4(10) . . . . ?
C3 N3 C10 C11 -2.4(11) . . . . ?
C2 N3 C10 C11 168.1(6) . . . . ?
C10 N3 C3 C4 -0.1(12) . . . . ?
C2 N3 C3 C4 -170.1(7) . . . . ?
C6 C7 C8 C9 -1.1(13) . . . . ?
F1 C7 C8 C9 -179.9(6) . . . . ?
C6 C7 C8 N1 178.4(8) . . . . ?
F1 C7 C8 N1 -0.5(11) . . . . ?
C14 N1 C8 C7 139.6(8) . . . . ?
C17 N1 C8 C7 -88.4(9) . . . . ?
C14 N1 C8 C9 -41.0(12) . . . . ?
C17 N1 C8 C9 90.9(9) . . . . ?
N3 C3 C4 C5 2.1(12) . . . . ?
N3 C3 C4 C13 -179.7(8) . . . . ?
F1 C7 C6 C11 178.8(5) . . . . ?
C8 C7 C6 C11 0.0(13) . . . . ?
C10 C11 C6 C7 0.2(11) . . . . ?
C5 C11 C6 C7 -179.4(7) . . . . ?
C1 O1 C9 C10 -23.9(9) . . . . ?
C1 O1 C9 C8 161.1(5) . . . . ?
C11 C10 C9 O1 -176.5(6) . . . . ?
N3 C10 C9 O1 0.9(11) . . . . ?
C11 C10 C9 C8 -1.8(12) . . . . ?
N3 C10 C9 C8 175.6(6) . . . . ?
C7 C8 C9 O1 176.9(7) . . . . ?
N1 C8 C9 O1 -2.5(11) . . . . ?
C7 C8 C9 C10 2.0(12) . . . . ?
N1 C8 C9 C10 -177.4(7) . . . . ?
C3 C4 C13 O4 4.5(11) . . . . ?
C5 C4 C13 O4 -177.3(6) . . . . ?
C3 C4 C13 O3 -175.8(8) . . . . ?
C5 C4 C13 O3 2.4(10) . . . . ?
C18 N2 C16 C17 179.9(7) . . . . ?
C15 N2 C16 C17 -57.5(7) . . . . ?
C3 C4 C5 O2 176.4(8) . . . . ?
C13 C4 C5 O2 -1.8(12) . . . . ?
C3 C4 C5 C11 -1.6(11) . . . . ?
C13 C4 C5 C11 -179.8(6) . . . . ?
C10 C11 C5 O2 -178.9(7) . . . . ?
C6 C11 C5 O2 0.6(11) . . . . ?
C10 C11 C5 C4 -0.8(10) . . . . ?
C6 C11 C5 C4 178.7(6) . . . . ?
C9 O1 C1 C2 53.4(10) . . . . ?
O1 C1 C2 C12 63.6(12) . . . . ?
O1 C1 C2 N3 -58.6(10) . . . . ?
C3 N3 C2 C1 -151.9(7) . . . . ?
C10 N3 C2 C1 37.9(8) . . . . ?
C3 N3 C2 C12 84.6(10) . . . . ?
C10 N3 C2 C12 -85.6(8) . . . . ?
C8 N1 C17 C16 168.0(8) . . . . ?
C14 N1 C17 C16 -56.4(8) . . . . ?
N2 C16 C17 N1 55.1(10) . . . . ?
C18 N2 C15 C14 -177.5(7) . . . . ?
C16 N2 C15 C14 60.1(8) . . . . ?
C8 N1 C14 C15 -169.4(8) . . . . ?
C17 N1 C14 C15 58.3(7) . . . . ?
N2 C15 C14 N1 -60.3(10) . . . . ?
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.032
_cell_measurement_pressure       2.16


# start Validation Reply Form
_vrf_ATOM007_OFLO_2p16           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_2p16           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_2p16           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_2p16           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_2p16           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_2p16           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_2p16           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_2p16           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_2p16           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_2p16           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_2p16           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_2p16           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_2p16           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_LH_PE_2p4
_database_code_depnum_ccdc_archive 'CCDC 2481334'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_Levo_HH_20241010_05

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Levofloxacin hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.25(H4 O2)'
_chemical_formula_sum            'C18 H21 F N3 O4.50'
_chemical_formula_weight         370.38
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   27.834(2)
_cell_length_b                   6.4010(5)
_cell_length_c                   18.072(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.524(5)
_cell_angle_gamma                90
_cell_volume                     2952.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    15574
_cell_measurement_theta_min      1.578
_cell_measurement_theta_max      24.703
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.997
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon III'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15574
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.578
_diffrn_reflns_theta_max         24.703
_diffrn_reflns_theta_full        24.703
_diffrn_measured_fraction_theta_max 0.644
_diffrn_measured_fraction_theta_full 0.644
_diffrn_reflns_Laue_measured_fraction_max 0.644
_diffrn_reflns_Laue_measured_fraction_full 0.644
_diffrn_reflns_point_group_measured_fraction_max 0.627
_diffrn_reflns_point_group_measured_fraction_full 0.627
_reflns_number_total             3158
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     0.606
_reflns_Friedel_fraction_full    0.606
_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_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'

_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1042P)²+6.7750P] 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_abs_structure_details 
;
 Flack x determined using 877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3158
_refine_ls_number_parameters     225
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1965
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      2.234
_refine_ls_shift/su_max          0.209
_refine_ls_shift/su_mean         0.005
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 0.20922(16) 0.4440(7) 0.7266(4) 0.0350(12) Uiso 1 1 d D U . . .
O1 O 0.3214(2) 0.4669(9) 1.2314(6) 0.0444(16) Uiso 1 1 d D U . . .
O2 O 0.37565(19) 0.4647(9) 1.1676(5) 0.0370(15) Uiso 1 1 d D U . . .
H2 H 0.372587 0.450892 1.120772 0.056 Uiso 1 1 calc R U . . .
O3 O 0.33766(17) 0.4748(7) 1.0154(5) 0.0270(13) Uiso 1 1 d D U . . .
O4 O 0.10171(18) 0.4442(8) 0.8724(5) 0.0303(13) Uiso 1 1 d D U . . .
N1 N 0.1910(2) 0.4568(9) 1.0178(5) 0.0234(14) Uiso 1 1 d D U . . .
N2 N 0.1109(2) 0.4624(9) 0.7232(5) 0.0259(15) Uiso 1 1 d D U . . .
N3 N 0.0127(2) 0.6411(9) 0.6250(5) 0.0286(16) Uiso 1 1 d D U . . .
C1 C 0.2339(2) 0.4589(11) 1.0866(6) 0.0274(18) Uiso 1 1 d D U . . .
H1 H 0.229825 0.457377 1.135217 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2841(2) 0.4634(11) 1.0887(5) 0.0226(17) Uiso 1 1 d D U . . .
C3 C 0.2923(2) 0.4674(10) 1.0156(5) 0.0195(16) Uiso 1 1 d D U . . .
C4 C 0.2495(2) 0.4597(10) 0.8665(6) 0.0205(16) Uiso 1 1 d D U . . .
H4 H 0.282213 0.460996 0.863949 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2051(2) 0.4559(11) 0.7979(6) 0.0246(18) Uiso 1 1 d D U . . .
C6 C 0.1536(2) 0.4574(10) 0.7965(5) 0.0185(16) Uiso 1 1 d D U . . .
C7 C 0.1507(2) 0.4514(10) 0.8717(5) 0.0190(16) Uiso 1 1 d D U . . .
C8 C 0.1954(2) 0.4556(10) 0.9440(6) 0.0200(16) Uiso 1 1 d D U . . .
C9 C 0.2454(2) 0.4615(10) 0.9411(6) 0.0197(16) Uiso 1 1 d D U . . .
C10 C 0.3279(2) 0.4667(11) 1.1697(6) 0.0244(18) Uiso 1 1 d D U . . .
C11 C 0.0990(3) 0.5339(12) 0.9421(6) 0.033(2) Uiso 1 1 d D U . . .
H11A H 0.063921 0.514795 0.940224 0.039 Uiso 1 1 calc R U . . .
H11B H 0.105489 0.682847 0.942484 0.039 Uiso 1 1 calc R U . . .
C12 C 0.1380(2) 0.4385(11) 1.0185(5) 0.0262(17) Uiso 1 1 d D U . . .
H12 H 0.129441 0.290976 1.021448 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1343(3) 0.5568(12) 1.0884(7) 0.034(2) Uiso 1 1 d D U . . .
H13A H 0.153636 0.483621 1.137808 0.051 Uiso 1 1 calc R U . . .
H13B H 0.098290 0.567934 1.080885 0.051 Uiso 1 1 calc R U . . .
H13C H 0.148811 0.694124 1.091031 0.051 Uiso 1 1 calc R U . . .
C14 C 0.0619(2) 0.3541(11) 0.7081(7) 0.0283(19) Uiso 1 1 d D U . . .
H14A H 0.065980 0.266763 0.754073 0.034 Uiso 1 1 calc R U . . .
H14B H 0.053232 0.264415 0.661267 0.034 Uiso 1 1 calc R U . . .
C15 C 0.0175(3) 0.5082(11) 0.6935(7) 0.031(2) Uiso 1 1 d D U . . .
H15A H -0.015061 0.433616 0.681935 0.037 Uiso 1 1 calc R U . . .
H15B H 0.024813 0.593196 0.741267 0.037 Uiso 1 1 calc R U . . .
C16 C 0.0613(3) 0.7606(12) 0.6447(8) 0.034(2) Uiso 1 1 d D U . . .
H16A H 0.067556 0.846969 0.691718 0.041 Uiso 1 1 calc R U . . .
H16B H 0.057775 0.851677 0.599902 0.041 Uiso 1 1 calc R U . . .
C17 C 0.1070(3) 0.6140(11) 0.6614(6) 0.0302(19) Uiso 1 1 d D U . . .
H17A H 0.102746 0.541254 0.612046 0.036 Uiso 1 1 calc R U . . .
H17B H 0.139155 0.694300 0.678665 0.036 Uiso 1 1 calc R U . . .
C18 C -0.0311(3) 0.7859(12) 0.6037(10) 0.044(2) Uiso 1 1 d D U . . .
H18A H -0.063264 0.708500 0.587701 0.065 Uiso 1 1 calc R U . . .
H18B H -0.032189 0.872859 0.559792 0.065 Uiso 1 1 calc R U . . .
H18C H -0.026908 0.871562 0.649462 0.065 Uiso 1 1 calc R U . . .
F2 F 0.28587(16) 0.7334(7) 0.7642(4) 0.0347(12) Uiso 1 1 d D U . . .
O5 O 0.1845(2) 0.7038(9) 0.2616(6) 0.0492(18) Uiso 1 1 d D U . . .
O6 O 0.12836(19) 0.7193(9) 0.3210(5) 0.0368(15) Uiso 1 1 d D U . . .
H6 H 0.129754 0.697665 0.366552 0.055 Uiso 1 1 calc R U . . .
O7 O 0.16198(18) 0.6786(8) 0.4722(5) 0.0290(13) Uiso 1 1 d D U . . .
O8 O 0.39795(18) 0.6988(8) 0.6272(5) 0.0337(14) Uiso 1 1 d D U . . .
N4 N 0.3102(2) 0.6632(9) 0.4789(5) 0.0265(15) Uiso 1 1 d D U . . .
N5 N 0.3846(2) 0.7199(9) 0.7719(5) 0.0257(15) Uiso 1 1 d D U . . .
N6 N 0.4842(2) 0.5853(9) 0.8803(5) 0.0280(15) Uiso 1 1 d D U . . .
C19 C 0.2689(2) 0.6680(11) 0.4087(6) 0.0284(19) Uiso 1 1 d D U . . .
H19 H 0.274264 0.659306 0.361244 0.034 Uiso 1 1 calc R U . . .
C20 C 0.2184(2) 0.6852(11) 0.4039(5) 0.0250(18) Uiso 1 1 d D U . . .
C21 C 0.2079(2) 0.6808(10) 0.4744(5) 0.0209(17) Uiso 1 1 d D U . . .
C22 C 0.2473(3) 0.6953(10) 0.6238(6) 0.0246(17) Uiso 1 1 d D U . . .
H22 H 0.214212 0.693370 0.624945 0.029 Uiso 1 1 calc R U . . .
C23 C 0.2907(2) 0.7085(11) 0.6933(6) 0.0249(18) Uiso 1 1 d D U . . .
C24 C 0.3428(2) 0.7085(11) 0.6974(5) 0.0222(17) Uiso 1 1 d D U . . .
C25 C 0.3480(2) 0.7006(10) 0.6235(5) 0.0205(17) Uiso 1 1 d D U . . .
C26 C 0.3037(2) 0.6849(10) 0.5510(6) 0.0215(17) Uiso 1 1 d D U . . .
C27 C 0.2529(2) 0.6847(10) 0.5514(6) 0.0205(17) Uiso 1 1 d D U . . .
C28 C 0.1760(3) 0.7028(11) 0.3215(6) 0.029(2) Uiso 1 1 d D U . . .
C29 C 0.4012(3) 0.7470(12) 0.5514(6) 0.0314(19) Uiso 1 1 d D U . . .
H29A H 0.436637 0.723443 0.555883 0.038 Uiso 1 1 calc R U . . .
H29B H 0.392692 0.893076 0.538435 0.038 Uiso 1 1 calc R U . . .
C30 C 0.3640(2) 0.6133(11) 0.4855(6) 0.0281(18) Uiso 1 1 d D U . . .
H30 H 0.371395 0.466711 0.501647 0.034 Uiso 1 1 calc R U . . .
C31 C 0.3699(3) 0.6434(14) 0.4069(7) 0.043(2) Uiso 1 1 d D U . . .
H31A H 0.350238 0.537915 0.369241 0.064 Uiso 1 1 calc R U . . .
H31B H 0.406223 0.632473 0.416011 0.064 Uiso 1 1 calc R U . . .
H31C H 0.356996 0.778959 0.385423 0.064 Uiso 1 1 calc R U . . .
C32 C 0.4312(2) 0.8444(11) 0.7866(7) 0.0261(18) Uiso 1 1 d D U . . .
H32A H 0.435848 0.943755 0.829461 0.031 Uiso 1 1 calc R U . . .
H32B H 0.426588 0.922485 0.738256 0.031 Uiso 1 1 calc R U . . .
C33 C 0.4795(3) 0.7088(11) 0.8101(6) 0.0287(19) Uiso 1 1 d D U . . .
H33A H 0.476573 0.617449 0.765694 0.034 Uiso 1 1 calc R U . . .
H33B H 0.510343 0.795628 0.822781 0.034 Uiso 1 1 calc R U . . .
C34 C 0.4380(2) 0.4500(12) 0.8607(7) 0.033(2) Uiso 1 1 d D U . . .
H34A H 0.442274 0.363573 0.907018 0.040 Uiso 1 1 calc R U . . .
H34B H 0.434881 0.358585 0.816213 0.040 Uiso 1 1 calc R U . . .
C35 C 0.3892(3) 0.5799(11) 0.8381(6) 0.0300(19) Uiso 1 1 d D U . . .
H35A H 0.358716 0.489373 0.821758 0.036 Uiso 1 1 calc R U . . .
H35B H 0.390634 0.660790 0.884335 0.036 Uiso 1 1 calc R U . . .
C36 C 0.5317(3) 0.4578(14) 0.9078(9) 0.043(2) Uiso 1 1 d D U . . .
H36A H 0.535255 0.394262 0.862197 0.065 Uiso 1 1 calc R U . . .
H36B H 0.529307 0.350825 0.943497 0.065 Uiso 1 1 calc R U . . .
H36C H 0.561596 0.544312 0.935980 0.065 Uiso 1 1 calc R U . . .
O9 O 0.000000 0.3468(14) 0.500000 0.049(2) Uiso 1 2 d DGS . P . .
H9A H -0.001525 0.413343 0.537750 0.074 Uiso 0.5 1 d DG U P . .
H9B H -0.010681 0.429781 0.461971 0.074 Uiso 0.5 1 d DG U P . .
O10 O 0.000000 0.3938(14) 1.000000 0.045(2) Uiso 1 2 d DGS . P . .
H10A H -0.013375 0.296700 0.969593 0.067 Uiso 0.5 1 d DG U P . .
H10B H -0.013260 0.496473 0.972390 0.067 Uiso 0.5 1 d DG U P . .
_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 C5 1.341(9) . ?
O1 C10 1.201(9) . ?
O2 C10 1.344(8) . ?
O2 H2 0.8200 . ?
O3 C3 1.264(7) . ?
O4 C7 1.370(7) . ?
O4 C11 1.415(10) . ?
N1 C1 1.336(9) . ?
N1 C8 1.387(9) . ?
N1 C12 1.487(8) . ?
N2 C6 1.384(9) . ?
N2 C17 1.451(10) . ?
N2 C14 1.455(7) . ?
N3 C18 1.457(8) . ?
N3 C15 1.464(10) . ?
N3 C16 1.467(8) . ?
C1 C2 1.384(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.427(10) . ?
C2 C10 1.485(10) . ?
C3 C9 1.455(9) . ?
C4 C5 1.358(9) . ?
C4 C9 1.397(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.423(8) . ?
C6 C7 1.393(9) . ?
C7 C8 1.399(9) . ?
C8 C9 1.413(8) . ?
C11 C12 1.504(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.511(11) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.519(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.511(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F2 C23 1.351(9) . ?
O5 C28 1.198(10) . ?
O6 C28 1.326(8) . ?
O6 H6 0.8200 . ?
O7 C21 1.262(8) . ?
O8 C25 1.365(7) . ?
O8 C29 1.441(10) . ?
N4 C19 1.329(9) . ?
N4 C26 1.391(9) . ?
N4 C30 1.490(8) . ?
N5 C24 1.387(9) . ?
N5 C32 1.453(7) . ?
N5 C35 1.459(10) . ?
N6 C33 1.455(10) . ?
N6 C36 1.460(8) . ?
N6 C34 1.472(8) . ?
C19 C20 1.378(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.417(10) . ?
C20 C28 1.490(10) . ?
C21 C27 1.453(9) . ?
C22 C23 1.352(9) . ?
C22 C27 1.380(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.421(8) . ?
C24 C25 1.401(10) . ?
C25 C26 1.399(9) . ?
C26 C27 1.419(8) . ?
C29 C30 1.496(9) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.505(11) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.512(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.505(8) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O9 H9A 0.8197 . ?
O9 H9B 0.8246 . ?
O9 H9A 0.8(4) 2_556 ?
O9 H9B 0.8(4) 2_556 ?
O10 H10A 0.8146 . ?
O10 H10B 0.8186 . ?
O10 H10A 0.81(17) 2_557 ?
O10 H10B 0.82(16) 2_557 ?
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 H2 109.5 . . ?
C7 O4 C11 113.7(6) . . ?
C1 N1 C8 120.4(6) . . ?
C1 N1 C12 121.0(8) . . ?
C8 N1 C12 118.5(6) . . ?
C6 N2 C17 121.6(6) . . ?
C6 N2 C14 123.5(7) . . ?
C17 N2 C14 113.4(6) . . ?
C18 N3 C15 112.1(8) . . ?
C18 N3 C16 109.0(6) . . ?
C15 N3 C16 109.6(7) . . ?
N1 C1 C2 122.9(9) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 120.5(7) . . ?
C1 C2 C10 116.7(8) . . ?
C3 C2 C10 122.8(6) . . ?
O3 C3 C2 122.0(7) . . ?
O3 C3 C9 121.9(8) . . ?
C2 C3 C9 116.1(6) . . ?
C5 C4 C9 119.0(7) . . ?
C5 C4 H4 120.5 . . ?
C9 C4 H4 120.5 . . ?
F1 C5 C4 118.9(6) . . ?
F1 C5 C6 117.1(7) . . ?
C4 C5 C6 124.0(8) . . ?
N2 C6 C7 125.0(6) . . ?
N2 C6 C5 119.4(8) . . ?
C7 C6 C5 115.6(7) . . ?
O4 C7 C6 117.0(6) . . ?
O4 C7 C8 120.6(8) . . ?
C6 C7 C8 122.3(6) . . ?
N1 C8 C7 120.8(6) . . ?
N1 C8 C9 120.1(7) . . ?
C7 C8 C9 119.1(8) . . ?
C4 C9 C8 119.8(7) . . ?
C4 C9 C3 120.2(6) . . ?
C8 C9 C3 119.9(8) . . ?
O1 C10 O2 123.0(8) . . ?
O1 C10 C2 123.2(7) . . ?
O2 C10 C2 113.8(8) . . ?
O4 C11 C12 112.2(6) . . ?
O4 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
O4 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N1 C12 C11 108.4(7) . . ?
N1 C12 C13 111.5(6) . . ?
C11 C12 C13 107.4(7) . . ?
N1 C12 H12 109.8 . . ?
C11 C12 H12 109.8 . . ?
C13 C12 H12 109.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.1(6) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 108.4(8) . . ?
N3 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
N3 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
N3 C16 C17 110.2(6) . . ?
N3 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N3 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N2 C17 C16 111.5(7) . . ?
N2 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 O6 H6 109.5 . . ?
C25 O8 C29 113.6(6) . . ?
C19 N4 C26 120.4(7) . . ?
C19 N4 C30 122.7(8) . . ?
C26 N4 C30 116.6(7) . . ?
C24 N5 C32 123.3(7) . . ?
C24 N5 C35 121.9(6) . . ?
C32 N5 C35 114.1(7) . . ?
C33 N6 C36 110.9(8) . . ?
C33 N6 C34 110.1(7) . . ?
C36 N6 C34 109.7(6) . . ?
N4 C19 C20 122.3(9) . . ?
N4 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C19 C20 C21 120.9(7) . . ?
C19 C20 C28 116.7(8) . . ?
C21 C20 C28 122.4(6) . . ?
O7 C21 C20 122.7(7) . . ?
O7 C21 C27 120.4(8) . . ?
C20 C21 C27 116.8(6) . . ?
C23 C22 C27 119.1(7) . . ?
C23 C22 H22 120.4 . . ?
C27 C22 H22 120.4 . . ?
F2 C23 C22 119.8(7) . . ?
F2 C23 C24 115.8(7) . . ?
C22 C23 C24 124.3(8) . . ?
N5 C24 C25 124.1(6) . . ?
N5 C24 C23 119.7(8) . . ?
C25 C24 C23 116.2(7) . . ?
O8 C25 C26 123.0(8) . . ?
O8 C25 C24 116.5(7) . . ?
C26 C25 C24 120.5(6) . . ?
N4 C26 C25 119.4(6) . . ?
N4 C26 C27 120.4(7) . . ?
C25 C26 C27 120.2(8) . . ?
C22 C27 C26 119.6(7) . . ?
C22 C27 C21 121.9(6) . . ?
C26 C27 C21 118.4(8) . . ?
O5 C28 O6 123.5(8) . . ?
O5 C28 C20 122.7(7) . . ?
O6 C28 C20 113.8(8) . . ?
O8 C29 C30 110.4(7) . . ?
O8 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
O8 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
N4 C30 C29 107.1(6) . . ?
N4 C30 C31 112.5(7) . . ?
C29 C30 C31 112.1(7) . . ?
N4 C30 H30 108.3 . . ?
C29 C30 H30 108.3 . . ?
C31 C30 H30 108.3 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 C33 111.4(6) . . ?
N5 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
N5 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
N6 C33 C32 108.5(7) . . ?
N6 C33 H33A 110.0 . . ?
C32 C33 H33A 110.0 . . ?
N6 C33 H33B 110.0 . . ?
C32 C33 H33B 110.0 . . ?
H33A C33 H33B 108.4 . . ?
N6 C34 C35 110.4(6) . . ?
N6 C34 H34A 109.6 . . ?
C35 C34 H34A 109.6 . . ?
N6 C34 H34B 109.6 . . ?
C35 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N5 C35 C34 109.6(8) . . ?
N5 C35 H35A 109.7 . . ?
C34 C35 H35A 109.7 . . ?
N5 C35 H35B 109.7 . . ?
C34 C35 H35B 109.8 . . ?
H35A C35 H35B 108.2 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H9A O9 H9B 103.7 . . ?
H9A O9 H9A 117.4 . 2_556 ?
H9B O9 H9A 24.8 . 2_556 ?
H9A O9 H9B 24.8 . 2_556 ?
H9B O9 H9B 99.8 . 2_556 ?
H9A O9 H9B 103.7 2_556 2_556 ?
H10A O10 H10B 103.2 . . ?
H10A O10 H10A 80.5 . 2_557 ?
H10B O10 H10A 175.7 . 2_557 ?
H10A O10 H10B 175.7 . 2_557 ?
H10B O10 H10B 73.2 . 2_557 ?
H10A O10 H10B 103.2 2_557 2_557 ?
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
C8 N1 C1 C2 1.0(11) . . . . ?
C12 N1 C1 C2 176.1(6) . . . . ?
N1 C1 C2 C3 0.4(11) . . . . ?
N1 C1 C2 C10 179.7(6) . . . . ?
C1 C2 C3 O3 178.9(7) . . . . ?
C10 C2 C3 O3 -0.3(10) . . . . ?
C1 C2 C3 C9 -1.4(10) . . . . ?
C10 C2 C3 C9 179.4(6) . . . . ?
C9 C4 C5 F1 -176.8(6) . . . . ?
C9 C4 C5 C6 1.1(11) . . . . ?
C17 N2 C6 C7 130.5(8) . . . . ?
C14 N2 C6 C7 -34.9(11) . . . . ?
C17 N2 C6 C5 -50.2(10) . . . . ?
C14 N2 C6 C5 144.4(7) . . . . ?
F1 C5 C6 N2 -4.8(10) . . . . ?
C4 C5 C6 N2 177.2(7) . . . . ?
F1 C5 C6 C7 174.6(6) . . . . ?
C4 C5 C6 C7 -3.4(10) . . . . ?
C11 O4 C7 C6 -151.9(6) . . . . ?
C11 O4 C7 C8 27.2(9) . . . . ?
N2 C6 C7 O4 1.9(10) . . . . ?
C5 C6 C7 O4 -177.5(6) . . . . ?
N2 C6 C7 C8 -177.2(6) . . . . ?
C5 C6 C7 C8 3.4(10) . . . . ?
C1 N1 C8 C7 179.4(6) . . . . ?
C12 N1 C8 C7 4.2(9) . . . . ?
C1 N1 C8 C9 -1.4(10) . . . . ?
C12 N1 C8 C9 -176.6(6) . . . . ?
O4 C7 C8 N1 -1.3(10) . . . . ?
C6 C7 C8 N1 177.8(6) . . . . ?
O4 C7 C8 C9 179.5(6) . . . . ?
C6 C7 C8 C9 -1.4(10) . . . . ?
C5 C4 C9 C8 1.1(10) . . . . ?
C5 C4 C9 C3 -179.4(6) . . . . ?
N1 C8 C9 C4 179.8(6) . . . . ?
C7 C8 C9 C4 -1.0(10) . . . . ?
N1 C8 C9 C3 0.4(10) . . . . ?
C7 C8 C9 C3 179.6(6) . . . . ?
O3 C3 C9 C4 1.3(10) . . . . ?
C2 C3 C9 C4 -178.5(6) . . . . ?
O3 C3 C9 C8 -179.3(6) . . . . ?
C2 C3 C9 C8 1.0(9) . . . . ?
C1 C2 C10 O1 -0.5(11) . . . . ?
C3 C2 C10 O1 178.7(7) . . . . ?
C1 C2 C10 O2 178.1(6) . . . . ?
C3 C2 C10 O2 -2.6(10) . . . . ?
C7 O4 C11 C12 -55.0(8) . . . . ?
C1 N1 C12 C11 154.9(6) . . . . ?
C8 N1 C12 C11 -29.9(9) . . . . ?
C1 N1 C12 C13 36.9(9) . . . . ?
C8 N1 C12 C13 -147.9(7) . . . . ?
O4 C11 C12 N1 55.2(8) . . . . ?
O4 C11 C12 C13 175.7(6) . . . . ?
C6 N2 C14 C15 113.5(9) . . . . ?
C17 N2 C14 C15 -52.9(12) . . . . ?
C18 N3 C15 C14 176.5(7) . . . . ?
C16 N3 C15 C14 -62.3(9) . . . . ?
N2 C14 C15 N3 57.9(11) . . . . ?
C18 N3 C16 C17 -176.0(10) . . . . ?
C15 N3 C16 C17 60.9(11) . . . . ?
C6 N2 C17 C16 -115.9(8) . . . . ?
C14 N2 C17 C16 50.8(10) . . . . ?
N3 C16 C17 N2 -54.2(11) . . . . ?
C26 N4 C19 C20 -2.8(10) . . . . ?
C30 N4 C19 C20 170.7(6) . . . . ?
N4 C19 C20 C21 -5.5(11) . . . . ?
N4 C19 C20 C28 176.1(6) . . . . ?
C19 C20 C21 O7 -173.9(7) . . . . ?
C28 C20 C21 O7 4.4(10) . . . . ?
C19 C20 C21 C27 7.8(10) . . . . ?
C28 C20 C21 C27 -173.9(6) . . . . ?
C27 C22 C23 F2 175.5(6) . . . . ?
C27 C22 C23 C24 -1.2(11) . . . . ?
C32 N5 C24 C25 38.9(10) . . . . ?
C35 N5 C24 C25 -130.3(8) . . . . ?
C32 N5 C24 C23 -139.8(7) . . . . ?
C35 N5 C24 C23 51.0(10) . . . . ?
F2 C23 C24 N5 4.0(10) . . . . ?
C22 C23 C24 N5 -179.2(6) . . . . ?
F2 C23 C24 C25 -174.8(6) . . . . ?
C22 C23 C24 C25 2.1(10) . . . . ?
C29 O8 C25 C26 18.9(9) . . . . ?
C29 O8 C25 C24 -164.2(6) . . . . ?
N5 C24 C25 O8 1.8(10) . . . . ?
C23 C24 C25 O8 -179.5(6) . . . . ?
N5 C24 C25 C26 178.7(6) . . . . ?
C23 C24 C25 C26 -2.5(10) . . . . ?
C19 N4 C26 C25 -173.6(6) . . . . ?
C30 N4 C26 C25 12.5(9) . . . . ?
C19 N4 C26 C27 8.3(10) . . . . ?
C30 N4 C26 C27 -165.6(6) . . . . ?
O8 C25 C26 N4 1.0(10) . . . . ?
C24 C25 C26 N4 -175.7(6) . . . . ?
O8 C25 C26 C27 179.1(6) . . . . ?
C24 C25 C26 C27 2.4(10) . . . . ?
C23 C22 C27 C26 0.9(10) . . . . ?
C23 C22 C27 C21 -176.9(6) . . . . ?
N4 C26 C27 C22 176.6(6) . . . . ?
C25 C26 C27 C22 -1.5(10) . . . . ?
N4 C26 C27 C21 -5.6(9) . . . . ?
C25 C26 C27 C21 176.4(6) . . . . ?
O7 C21 C27 C22 -2.8(10) . . . . ?
C20 C21 C27 C22 175.5(6) . . . . ?
O7 C21 C27 C26 179.4(6) . . . . ?
C20 C21 C27 C26 -2.3(9) . . . . ?
C19 C20 C28 O5 -0.6(11) . . . . ?
C21 C20 C28 O5 -179.0(7) . . . . ?
C19 C20 C28 O6 -179.9(7) . . . . ?
C21 C20 C28 O6 1.7(9) . . . . ?
C25 O8 C29 C30 -51.0(8) . . . . ?
C19 N4 C30 C29 143.6(7) . . . . ?
C26 N4 C30 C29 -42.6(9) . . . . ?
C19 N4 C30 C31 19.9(9) . . . . ?
C26 N4 C30 C31 -166.3(6) . . . . ?
O8 C29 C30 N4 61.8(8) . . . . ?
O8 C29 C30 C31 -174.3(6) . . . . ?
C24 N5 C32 C33 -116.7(9) . . . . ?
C35 N5 C32 C33 53.3(11) . . . . ?
C36 N6 C33 C32 -177.5(7) . . . . ?
C34 N6 C33 C32 60.9(8) . . . . ?
N5 C32 C33 N6 -56.2(10) . . . . ?
C33 N6 C34 C35 -61.9(11) . . . . ?
C36 N6 C34 C35 175.8(10) . . . . ?
C24 N5 C35 C34 118.0(8) . . . . ?
C32 N5 C35 C34 -52.2(10) . . . . ?
N6 C34 C35 N5 55.5(11) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.76 2.522(11) 152.7 . yes
O6 H6 O7 0.82 1.76 2.523(12) 154.1 . yes
O10 H10A N6 0.81 2.09 2.831(10) 151.8 3_445 yes
O9 H9A N3 0.82 2.07 2.854(10) 160.7 . yes
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.064
_cell_measurement_pressure       2.4


# start Validation Reply Form
_vrf_ATOM007_LH_PE_2p4           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2.
;
_vrf_PLAT201_LH_PE_2p4           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_LH_PE_2p4           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_LH_PE_2p4           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_LH_PE_2p4           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_LH_PE_2p4           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_LH_PE_2p4           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_LH_PE_2p4           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_LH_PE_2p4           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT420_LH_ME_2p4           
;
RESPONSE: The water molecule is disordered
;
_vrf_PLAT915_LH_ME_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell 
;
_vrf_PLAT111_LH_PE_2p4           
;
RESPONSE: The structure is chiral.

;
_vrf_PLAT721_LH_PE_2p4           
;
RESPONSE: The hydrogen atoms were added to the structure and allowed to refine
with DFIX restraints

;
_vrf_PLAT910_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_LH_PE_2p4           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_LH_PE_2p4           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_LH_PE_2p4           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_LH_PE_2p4           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_OFLO_1p24
_database_code_depnum_ccdc_archive 'CCDC 2481341'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_060522_run1_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   29.425(10)
_cell_length_b                   6.4513(8)
_cell_length_c                   16.439(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.14(2)
_cell_angle_gamma                90
_cell_volume                     3026.0(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5594
_cell_measurement_theta_min      2.555
_cell_measurement_theta_max      23.283
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6722
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            5594
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         23.283
_diffrn_reflns_theta_full        23.283
_diffrn_measured_fraction_theta_max 0.354
_diffrn_measured_fraction_theta_full 0.354
_diffrn_reflns_Laue_measured_fraction_max 0.354
_diffrn_reflns_Laue_measured_fraction_full 0.354
_diffrn_reflns_point_group_measured_fraction_max 0.354
_diffrn_reflns_point_group_measured_fraction_full 0.354
_reflns_number_total             773
_reflns_number_gt                486
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+15.8378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         773
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      0.935
_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
F1 F 0.5698(4) 0.7036(7) 0.7829(3) 0.059(6) Uani 1 1 d D . . . .
O1 O 0.6474(5) 0.6090(9) 0.5662(4) 0.049(6) Uani 1 1 d D . . . .
O4 O 0.4372(5) 0.8027(8) 0.2701(3) 0.041(8) Uani 1 1 d D . . . .
C11 C 0.5232(6) 0.7303(12) 0.5579(5) 0.035(5) Uani 1 1 d D . . . .
O2 O 0.4435(5) 0.8186(8) 0.5219(4) 0.042(6) Uani 1 1 d D . . . .
N3 N 0.5622(6) 0.6907(11) 0.4455(5) 0.040(5) Uani 1 1 d D . . . .
N1 N 0.6506(6) 0.6210(11) 0.7405(5) 0.042(5) Uani 1 1 d D . . . .
C7 C 0.5678(7) 0.6958(13) 0.6988(6) 0.036(5) Uani 1 1 d D . . . .
C10 C 0.5640(6) 0.6857(12) 0.5320(5) 0.035(5) Uani 1 1 d D . . . .
C3 C 0.5219(7) 0.7336(13) 0.3909(6) 0.034(5) Uani 1 1 d D . . . .
H3 H 0.521843 0.736789 0.334294 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6096(7) 0.6488(12) 0.6766(6) 0.036(5) Uani 1 1 d D . . . .
O3 O 0.3997(6) 0.8627(9) 0.3702(4) 0.053(6) Uani 1 1 d D . . . .
H3A H 0.406026 0.862080 0.421587 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4806(7) 0.7733(13) 0.4116(6) 0.034(5) Uani 1 1 d D . . . .
C6 C 0.5253(7) 0.7355(13) 0.6448(6) 0.042(6) Uani 1 1 d D . . . .
H6 H 0.498937 0.764689 0.664492 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6061(6) 0.6449(13) 0.5896(5) 0.038(5) Uani 1 1 d D . . . .
N2 N 0.7438(5) 0.6102(10) 0.8395(4) 0.044(6) Uani 1 1 d D . . . .
C13 C 0.4370(7) 0.8128(13) 0.3445(6) 0.044(6) Uani 1 1 d D . . . .
C16 C 0.7121(6) 0.7793(13) 0.8487(5) 0.049(7) Uani 1 1 d D . . . .
H16A H 0.730146 0.905136 0.864587 0.059 Uiso 1 1 calc R U . . .
H16B H 0.696891 0.745242 0.893013 0.059 Uiso 1 1 calc R U . . .
C5 C 0.4785(6) 0.7742(12) 0.4977(5) 0.035(5) Uani 1 1 d D . . . .
C1 C 0.6402(7) 0.5307(12) 0.4805(5) 0.049(7) Uani 1 1 d D . . . .
H1A H 0.625893 0.394461 0.476104 0.059 Uiso 1 1 calc R U . . .
H1B H 0.670085 0.519066 0.465649 0.059 Uiso 1 1 calc R U . . .
C12 C 0.6302(8) 0.8954(12) 0.4207(6) 0.053(9) Uani 1 1 d D . . . .
H12A H 0.608157 0.985892 0.384960 0.079 Uiso 1 1 calc R U . . .
H12B H 0.657943 0.884543 0.400055 0.079 Uiso 1 1 calc R U . . .
H12C H 0.638296 0.950628 0.476663 0.079 Uiso 1 1 calc R U . . .
C2 C 0.6084(7) 0.6816(12) 0.4216(5) 0.044(6) Uani 1 1 d D . . . .
H2 H 0.602605 0.624872 0.364706 0.053 Uiso 1 1 calc R U . . .
C17 C 0.6755(6) 0.8160(12) 0.7682(5) 0.041(7) Uani 1 1 d D . . . .
H17A H 0.653445 0.920201 0.777114 0.049 Uiso 1 1 calc R U . . .
H17B H 0.690277 0.866187 0.725343 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7170(6) 0.4205(12) 0.8130(5) 0.047(6) Uani 1 1 d D . . . .
H15A H 0.700826 0.380386 0.855323 0.056 Uiso 1 1 calc R U . . .
H15B H 0.738284 0.309388 0.807546 0.056 Uiso 1 1 calc R U . . .
C18 C 0.7796(6) 0.5773(16) 0.9170(5) 0.063(7) Uani 1 1 d D . . . .
H18A H 0.797525 0.701899 0.931687 0.094 Uiso 1 1 calc R U . . .
H18B H 0.799890 0.466551 0.909332 0.094 Uiso 1 1 calc R U . . .
H18C H 0.764800 0.541755 0.961175 0.094 Uiso 1 1 calc R U . . .
C14 C 0.6818(6) 0.4516(13) 0.7304(5) 0.047(6) Uani 1 1 d D . . . .
H14A H 0.697783 0.485834 0.687026 0.056 Uiso 1 1 calc R U . . .
H14B H 0.663950 0.325561 0.714183 0.056 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 C7 1.371(8) . ?
O1 C9 1.381(15) . ?
O1 C1 1.463(8) . ?
O4 C13 1.226(9) . ?
C11 C10 1.398(13) . ?
C11 C6 1.416(10) . ?
C11 C5 1.467(11) . ?
O2 C5 1.223(15) . ?
N3 C3 1.331(17) . ?
N3 C10 1.410(9) . ?
N3 C2 1.506(18) . ?
N1 C8 1.405(19) . ?
N1 C14 1.463(14) . ?
N1 C17 1.471(13) . ?
C7 C6 1.369(18) . ?
C7 C8 1.399(19) . ?
C10 C9 1.388(17) . ?
C3 C4 1.364(19) . ?
C3 H3 0.9300 . ?
C8 C9 1.409(10) . ?
O3 C13 1.309(18) . ?
O3 H3A 0.8200 . ?
C4 C5 1.433(11) . ?
C4 C13 1.495(16) . ?
C6 H6 0.9300 . ?
N2 C18 1.457(11) . ?
N2 C15 1.463(14) . ?
N2 C16 1.466(15) . ?
C16 C17 1.507(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.523(17) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.523(14) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.505(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 113.3(12) . . ?
C10 C11 C6 118.8(13) . . ?
C10 C11 C5 122.0(8) . . ?
C6 C11 C5 119.2(12) . . ?
C3 N3 C10 119.5(13) . . ?
C3 N3 C2 123.0(7) . . ?
C10 N3 C2 116.7(13) . . ?
C8 N1 C14 117.3(8) . . ?
C8 N1 C17 113.2(9) . . ?
C14 N1 C17 113.3(12) . . ?
C6 C7 F1 117.0(12) . . ?
C6 C7 C8 126.4(9) . . ?
F1 C7 C8 116.6(13) . . ?
C9 C10 C11 121.5(8) . . ?
C9 C10 N3 119.9(13) . . ?
C11 C10 N3 118.6(13) . . ?
N3 C3 C4 124.9(9) . . ?
N3 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
C7 C8 N1 118.8(8) . . ?
C7 C8 C9 114.7(14) . . ?
N1 C8 C9 126.5(15) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.2(14) . . ?
C3 C4 C13 120.3(8) . . ?
C5 C4 C13 119.5(13) . . ?
C7 C6 C11 117.3(13) . . ?
C7 C6 H6 121.3 . . ?
C11 C6 H6 121.3 . . ?
O1 C9 C10 122.8(7) . . ?
O1 C9 C8 115.7(13) . . ?
C10 C9 C8 121.4(13) . . ?
C18 N2 C15 111.1(8) . . ?
C18 N2 C16 111.1(7) . . ?
C15 N2 C16 110.1(12) . . ?
O4 C13 O3 123.0(15) . . ?
O4 C13 C4 120.9(14) . . ?
O3 C13 C4 116.1(9) . . ?
N2 C16 C17 111.3(7) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O2 C5 C4 124.4(14) . . ?
O2 C5 C11 120.8(9) . . ?
C4 C5 C11 114.7(12) . . ?
O1 C1 C2 108.2(8) . . ?
O1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
O1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C12 112.1(11) . . ?
N3 C2 C1 108.2(9) . . ?
C12 C2 C1 113.0(14) . . ?
N3 C2 H2 107.8 . . ?
C12 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
N1 C17 C16 109.4(8) . . ?
N1 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N1 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
N2 C15 C14 111.0(8) . . ?
N2 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
N2 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 108.0(8) . . ?
N1 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
N1 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
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
C6 C11 C10 C9 0.6(13) . . . . ?
C5 C11 C10 C9 179.9(9) . . . . ?
C6 C11 C10 N3 -176.9(8) . . . . ?
C5 C11 C10 N3 2.4(12) . . . . ?
C3 N3 C10 C9 -178.8(10) . . . . ?
C2 N3 C10 C9 -8.7(13) . . . . ?
C3 N3 C10 C11 -1.3(14) . . . . ?
C2 N3 C10 C11 168.9(7) . . . . ?
C10 N3 C3 C4 -0.4(16) . . . . ?
C2 N3 C3 C4 -169.9(8) . . . . ?
C6 C7 C8 N1 177.3(10) . . . . ?
F1 C7 C8 N1 -2.4(13) . . . . ?
C6 C7 C8 C9 0.4(15) . . . . ?
F1 C7 C8 C9 -179.3(7) . . . . ?
C14 N1 C8 C7 138.9(9) . . . . ?
C17 N1 C8 C7 -86.3(11) . . . . ?
C14 N1 C8 C9 -44.6(14) . . . . ?
C17 N1 C8 C9 90.2(11) . . . . ?
N3 C3 C4 C5 1.0(15) . . . . ?
N3 C3 C4 C13 -178.0(10) . . . . ?
F1 C7 C6 C11 179.2(7) . . . . ?
C8 C7 C6 C11 -0.5(16) . . . . ?
C10 C11 C6 C7 0.0(13) . . . . ?
C5 C11 C6 C7 -179.3(9) . . . . ?
C1 O1 C9 C10 -24.8(12) . . . . ?
C1 O1 C9 C8 158.5(7) . . . . ?
C11 C10 C9 O1 -177.1(8) . . . . ?
N3 C10 C9 O1 0.3(15) . . . . ?
C11 C10 C9 C8 -0.7(15) . . . . ?
N3 C10 C9 C8 176.8(8) . . . . ?
C7 C8 C9 O1 176.9(8) . . . . ?
N1 C8 C9 O1 0.3(13) . . . . ?
C7 C8 C9 C10 0.2(14) . . . . ?
N1 C8 C9 C10 -176.4(9) . . . . ?
C3 C4 C13 O4 2.7(14) . . . . ?
C5 C4 C13 O4 -176.3(8) . . . . ?
C3 C4 C13 O3 -175.7(9) . . . . ?
C5 C4 C13 O3 5.2(13) . . . . ?
C18 N2 C16 C17 179.2(9) . . . . ?
C15 N2 C16 C17 -57.3(9) . . . . ?
C3 C4 C5 O2 176.1(9) . . . . ?
C13 C4 C5 O2 -4.9(14) . . . . ?
C3 C4 C5 C11 0.0(13) . . . . ?
C13 C4 C5 C11 179.1(8) . . . . ?
C10 C11 C5 O2 -177.9(9) . . . . ?
C6 C11 C5 O2 1.3(13) . . . . ?
C10 C11 C5 C4 -1.7(12) . . . . ?
C6 C11 C5 C4 177.5(8) . . . . ?
C9 O1 C1 C2 55.0(12) . . . . ?
C3 N3 C2 C12 83.2(12) . . . . ?
C10 N3 C2 C12 -86.5(11) . . . . ?
C3 N3 C2 C1 -151.5(10) . . . . ?
C10 N3 C2 C1 38.8(10) . . . . ?
O1 C1 C2 N3 -61.1(13) . . . . ?
O1 C1 C2 C12 63.6(14) . . . . ?
C8 N1 C17 C16 167.3(9) . . . . ?
C14 N1 C17 C16 -56.1(9) . . . . ?
N2 C16 C17 N1 54.7(12) . . . . ?
C18 N2 C15 C14 -176.9(8) . . . . ?
C16 N2 C15 C14 59.6(9) . . . . ?
C8 N1 C14 C15 -167.6(10) . . . . ?
C17 N1 C14 C15 57.6(9) . . . . ?
N2 C15 C14 N1 -58.6(11) . . . . ?
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.040
_cell_measurement_pressure       1.24



# start Validation Reply Form
_vrf_ATOM007_OFLO_1p24           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_1p24           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_1p24           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_1p24           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_1p24           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_1p24           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_1p24           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_1p24           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_1p24           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_1p24           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_1p24           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_1p24           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_1p24           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_OFLO_4p47
_database_code_depnum_ccdc_archive 'CCDC 2481347'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_270522_run1_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   28.547(7)
_cell_length_b                   6.0686(5)
_cell_length_c                   15.8759(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.121(16)
_cell_angle_gamma                90
_cell_volume                     2678.6(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4915
_cell_measurement_theta_min      2.635
_cell_measurement_theta_max      23.269
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6788
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            4915
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.635
_diffrn_reflns_theta_max         23.269
_diffrn_reflns_theta_full        23.269
_diffrn_measured_fraction_theta_max 0.348
_diffrn_measured_fraction_theta_full 0.348
_diffrn_reflns_Laue_measured_fraction_max 0.348
_diffrn_reflns_Laue_measured_fraction_full 0.348
_diffrn_reflns_point_group_measured_fraction_max 0.348
_diffrn_reflns_point_group_measured_fraction_full 0.348
_reflns_number_total             672
_reflns_number_gt                478
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+9.9383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         672
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      0.905
_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
F1 F 0.5703(3) 0.7011(5) 0.7913(2) 0.020(6) Uani 1 1 d D . . . .
O1 O 0.6497(5) 0.5852(7) 0.5666(3) 0.034(5) Uani 1 1 d D . . . .
O4 O 0.4349(4) 0.8147(6) 0.2674(3) 0.023(7) Uani 1 1 d D . . . .
C11 C 0.5239(5) 0.7286(10) 0.5609(4) 0.026(4) Uani 1 1 d D . . . .
O2 O 0.4413(4) 0.8248(7) 0.5261(3) 0.030(5) Uani 1 1 d D . . . .
N3 N 0.5643(5) 0.6834(9) 0.4443(4) 0.030(5) Uani 1 1 d D . . . .
N1 N 0.6512(5) 0.6016(8) 0.7456(4) 0.028(5) Uani 1 1 d D . . . .
C7 C 0.5669(6) 0.6900(10) 0.7039(4) 0.020(5) Uani 1 1 d D . . . .
C10 C 0.5656(6) 0.6776(10) 0.5330(4) 0.027(5) Uani 1 1 d D . . . .
C3 C 0.5225(7) 0.7319(12) 0.3883(5) 0.028(5) Uani 1 1 d D . . . .
H3 H 0.522602 0.737531 0.329773 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6100(6) 0.6347(10) 0.6802(5) 0.025(4) Uani 1 1 d D . . . .
O3 O 0.3989(5) 0.8754(7) 0.3746(3) 0.034(5) Uani 1 1 d D . . . .
H3A H 0.405161 0.859035 0.427193 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4804(6) 0.7731(10) 0.4113(4) 0.026(5) Uani 1 1 d D . . . .
C6 C 0.5247(6) 0.7334(10) 0.6497(4) 0.026(5) Uani 1 1 d D . . . .
H6 H 0.497276 0.765180 0.669797 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6079(6) 0.6292(11) 0.5913(5) 0.027(5) Uani 1 1 d D . . . .
N2 N 0.7474(5) 0.5927(8) 0.8421(3) 0.027(5) Uani 1 1 d D . . . .
C13 C 0.4361(6) 0.8220(10) 0.3450(4) 0.027(5) Uani 1 1 d D . . . .
C16 C 0.7155(5) 0.7744(9) 0.8510(4) 0.028(6) Uani 1 1 d D . . . .
H16A H 0.734295 0.908207 0.864607 0.034 Uiso 1 1 calc R U . . .
H16B H 0.700363 0.743824 0.898555 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4779(5) 0.7762(10) 0.5001(4) 0.023(4) Uani 1 1 d D . . . .
C1 C 0.6444(6) 0.5201(9) 0.4780(4) 0.034(6) Uani 1 1 d D . . . .
H1A H 0.631335 0.371949 0.470136 0.041 Uiso 1 1 calc R U . . .
H1B H 0.675572 0.519351 0.463485 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6318(7) 0.9032(9) 0.4203(4) 0.039(8) Uani 1 1 d D . . . .
H12A H 0.609550 0.997454 0.382292 0.059 Uiso 1 1 calc R U . . .
H12B H 0.661495 0.897078 0.401668 0.059 Uiso 1 1 calc R U . . .
H12C H 0.637715 0.960447 0.478156 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6111(6) 0.6771(10) 0.4186(4) 0.030(5) Uani 1 1 d D . . . .
H2 H 0.605653 0.620382 0.359395 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6775(5) 0.8092(9) 0.7701(3) 0.027(6) Uani 1 1 d D . . . .
H17A H 0.655353 0.922839 0.779626 0.033 Uiso 1 1 calc R U . . .
H17B H 0.692159 0.857200 0.723803 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7200(5) 0.3889(9) 0.8183(3) 0.026(6) Uani 1 1 d D . . . .
H15A H 0.703961 0.348195 0.863762 0.031 Uiso 1 1 calc R U . . .
H15B H 0.741642 0.270367 0.811629 0.031 Uiso 1 1 calc R U . . .
C18 C 0.7840(5) 0.5593(11) 0.9217(4) 0.032(6) Uani 1 1 d D . . . .
H18A H 0.802888 0.690827 0.935174 0.047 Uiso 1 1 calc R U . . .
H18B H 0.804428 0.438901 0.914128 0.047 Uiso 1 1 calc R U . . .
H18C H 0.768660 0.526343 0.968156 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6834(5) 0.4221(10) 0.7351(4) 0.031(6) Uani 1 1 d D . . . .
H14A H 0.699417 0.457259 0.689101 0.038 Uiso 1 1 calc R U . . .
H14B H 0.665035 0.287757 0.719585 0.038 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 C7 1.372(6) . ?
O1 C9 1.367(15) . ?
O1 C1 1.434(6) . ?
O4 C13 1.226(7) . ?
C11 C10 1.395(13) . ?
C11 C6 1.405(8) . ?
C11 C5 1.472(11) . ?
O2 C5 1.241(14) . ?
N3 C3 1.347(16) . ?
N3 C10 1.401(8) . ?
N3 C2 1.483(17) . ?
N1 C8 1.395(16) . ?
N1 C14 1.459(12) . ?
N1 C17 1.473(11) . ?
C7 C6 1.338(16) . ?
C7 C8 1.406(18) . ?
C10 C9 1.376(16) . ?
C3 C4 1.358(18) . ?
C3 H3 0.9300 . ?
C8 C9 1.399(9) . ?
O3 C13 1.294(16) . ?
O3 H3A 0.8200 . ?
C4 C5 1.428(9) . ?
C4 C13 1.481(15) . ?
C6 H6 0.9300 . ?
N2 C16 1.456(12) . ?
N2 C18 1.459(10) . ?
N2 C15 1.467(11) . ?
C16 C17 1.496(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.515(15) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.492(12) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.500(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 115.4(11) . . ?
C10 C11 C6 120.2(11) . . ?
C10 C11 C5 122.3(6) . . ?
C6 C11 C5 117.5(10) . . ?
C3 N3 C10 119.1(12) . . ?
C3 N3 C2 122.8(7) . . ?
C10 N3 C2 117.1(12) . . ?
C8 N1 C14 118.0(6) . . ?
C8 N1 C17 111.5(6) . . ?
C14 N1 C17 111.9(10) . . ?
C6 C7 F1 119.2(11) . . ?
C6 C7 C8 126.2(8) . . ?
F1 C7 C8 114.6(11) . . ?
C9 C10 C11 120.9(7) . . ?
C9 C10 N3 120.1(12) . . ?
C11 C10 N3 118.9(11) . . ?
N3 C3 C4 124.6(7) . . ?
N3 C3 H3 117.7 . . ?
C4 C3 H3 117.7 . . ?
N1 C8 C9 125.7(13) . . ?
N1 C8 C7 118.5(7) . . ?
C9 C8 C7 115.7(13) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 121.0(13) . . ?
C3 C4 C13 120.8(7) . . ?
C5 C4 C13 118.2(12) . . ?
C7 C6 C11 116.6(12) . . ?
C7 C6 H6 121.7 . . ?
C11 C6 H6 121.7 . . ?
O1 C9 C10 122.6(7) . . ?
O1 C9 C8 117.0(12) . . ?
C10 C9 C8 120.3(12) . . ?
C16 N2 C18 111.2(5) . . ?
C16 N2 C15 110.8(10) . . ?
C18 N2 C15 110.0(6) . . ?
O4 C13 O3 122.3(13) . . ?
O4 C13 C4 122.2(12) . . ?
O3 C13 C4 115.5(7) . . ?
N2 C16 C17 111.8(6) . . ?
N2 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N2 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
O2 C5 C4 124.4(12) . . ?
O2 C5 C11 121.5(7) . . ?
C4 C5 C11 114.0(11) . . ?
O1 C1 C2 110.5(7) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C12 110.5(9) . . ?
N3 C2 C1 108.8(7) . . ?
C12 C2 C1 112.1(12) . . ?
N3 C2 H2 108.4 . . ?
C12 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
N1 C17 C16 109.4(6) . . ?
N1 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N1 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
N2 C15 C14 109.8(6) . . ?
N2 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 109.3(6) . . ?
N1 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
N1 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
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
C6 C11 C10 C9 0.6(11) . . . . ?
C5 C11 C10 C9 -178.6(7) . . . . ?
C6 C11 C10 N3 -177.2(7) . . . . ?
C5 C11 C10 N3 3.5(10) . . . . ?
C3 N3 C10 C9 -179.8(7) . . . . ?
C2 N3 C10 C9 -11.0(10) . . . . ?
C3 N3 C10 C11 -1.9(11) . . . . ?
C2 N3 C10 C11 166.9(6) . . . . ?
C10 N3 C3 C4 -1.2(13) . . . . ?
C2 N3 C3 C4 -169.2(7) . . . . ?
C14 N1 C8 C9 -43.3(11) . . . . ?
C17 N1 C8 C9 88.2(9) . . . . ?
C14 N1 C8 C7 140.3(8) . . . . ?
C17 N1 C8 C7 -88.2(9) . . . . ?
C6 C7 C8 N1 177.9(7) . . . . ?
F1 C7 C8 N1 -1.3(10) . . . . ?
C6 C7 C8 C9 1.2(12) . . . . ?
F1 C7 C8 C9 -178.0(6) . . . . ?
N3 C3 C4 C5 2.5(13) . . . . ?
N3 C3 C4 C13 -179.1(7) . . . . ?
F1 C7 C6 C11 177.4(6) . . . . ?
C8 C7 C6 C11 -1.8(12) . . . . ?
C10 C11 C6 C7 0.8(11) . . . . ?
C5 C11 C6 C7 -179.9(6) . . . . ?
C1 O1 C9 C10 -20.0(10) . . . . ?
C1 O1 C9 C8 163.2(5) . . . . ?
C11 C10 C9 O1 -177.9(7) . . . . ?
N3 C10 C9 O1 0.0(12) . . . . ?
C11 C10 C9 C8 -1.3(11) . . . . ?
N3 C10 C9 C8 176.6(6) . . . . ?
N1 C8 C9 O1 0.8(11) . . . . ?
C7 C8 C9 O1 177.3(7) . . . . ?
N1 C8 C9 C10 -176.1(7) . . . . ?
C7 C8 C9 C10 0.4(11) . . . . ?
C3 C4 C13 O4 4.4(11) . . . . ?
C5 C4 C13 O4 -177.3(7) . . . . ?
C3 C4 C13 O3 -174.9(8) . . . . ?
C5 C4 C13 O3 3.5(9) . . . . ?
C18 N2 C16 C17 -179.4(7) . . . . ?
C15 N2 C16 C17 -56.8(7) . . . . ?
C3 C4 C5 O2 175.8(7) . . . . ?
C13 C4 C5 O2 -2.6(11) . . . . ?
C3 C4 C5 C11 -0.8(10) . . . . ?
C13 C4 C5 C11 -179.2(6) . . . . ?
C10 C11 C5 O2 -178.8(7) . . . . ?
C6 C11 C5 O2 1.9(10) . . . . ?
C10 C11 C5 C4 -2.1(9) . . . . ?
C6 C11 C5 C4 178.6(6) . . . . ?
C9 O1 C1 C2 48.6(11) . . . . ?
C3 N3 C2 C12 83.4(10) . . . . ?
C10 N3 C2 C12 -84.9(9) . . . . ?
C3 N3 C2 C1 -153.1(7) . . . . ?
C10 N3 C2 C1 38.6(8) . . . . ?
O1 C1 C2 N3 -56.8(11) . . . . ?
O1 C1 C2 C12 65.7(13) . . . . ?
C8 N1 C17 C16 169.1(8) . . . . ?
C14 N1 C17 C16 -56.4(7) . . . . ?
N2 C16 C17 N1 54.8(9) . . . . ?
C16 N2 C15 C14 58.3(7) . . . . ?
C18 N2 C15 C14 -178.4(7) . . . . ?
C8 N1 C14 C15 -169.8(8) . . . . ?
C17 N1 C14 C15 58.9(7) . . . . ?
N2 C15 C14 N1 -59.0(10) . . . . ?
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.037
_cell_measurement_pressure       4.47

# start Validation Reply Form
_vrf_ATOM007_OFLO_4p47           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_4p47           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_4p47           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_4p47           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_4p47           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_4p47           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_4p47           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_4p47           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_4p47           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_4p47           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_4p47           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_4p47           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_4p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
####################################################################### 
# 
# 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_OFLO_2p47
_database_code_depnum_ccdc_archive 'CCDC 2481344'
loop_
_audit_author_name
_audit_author_address
'Iain Douglas Hood Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
#data_mo_OFLO_230522_run1_0m

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ofloxacin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   28.984(8)
_cell_length_b                   6.2603(6)
_cell_length_c                   16.1666(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.600(18)
_cell_angle_gamma                90
_cell_volume                     2851.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5267
_cell_measurement_theta_min      2.592
_cell_measurement_theta_max      23.262
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.6696
_exptl_absorpt_correction_t_max  0.7449
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            5267
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         23.262
_diffrn_reflns_theta_full        23.262
_diffrn_measured_fraction_theta_max 0.350
_diffrn_measured_fraction_theta_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.350
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.350
_diffrn_reflns_point_group_measured_fraction_full 0.349
_reflns_number_total             714
_reflns_number_gt                495
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_refine_special_details          'CX-ASAP (Thompson, 2023)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0201P)²+5.3119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         714
_refine_ls_number_parameters     238
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      0.954
_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
F1 F 0.5702(3) 0.7037(4) 0.78698(19) 0.039(5) Uani 1 1 d D . . . .
O1 O 0.6481(4) 0.5989(6) 0.5663(3) 0.035(5) Uani 1 1 d D . . . .
O4 O 0.4358(4) 0.8066(5) 0.2688(2) 0.030(6) Uani 1 1 d D . . . .
C11 C 0.5238(5) 0.7297(9) 0.5594(4) 0.023(4) Uani 1 1 d D . . . .
O2 O 0.4430(4) 0.8217(6) 0.5242(3) 0.030(5) Uani 1 1 d D . . . .
N3 N 0.5636(5) 0.6879(8) 0.4455(3) 0.025(4) Uani 1 1 d D . . . .
N1 N 0.6511(5) 0.6117(7) 0.7430(3) 0.025(4) Uani 1 1 d D . . . .
C7 C 0.5678(6) 0.6942(10) 0.7013(4) 0.020(4) Uani 1 1 d D . . . .
C10 C 0.5644(5) 0.6812(9) 0.5325(4) 0.020(4) Uani 1 1 d D . . . .
C3 C 0.5230(6) 0.7308(10) 0.3902(5) 0.024(4) Uani 1 1 d D . . . .
H3 H 0.523067 0.732830 0.332769 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6096(6) 0.6446(9) 0.6785(4) 0.020(4) Uani 1 1 d D . . . .
O3 O 0.4000(4) 0.8673(6) 0.3727(3) 0.035(5) Uani 1 1 d D . . . .
H3A H 0.406466 0.862166 0.424847 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4810(6) 0.7722(9) 0.4117(4) 0.024(4) Uani 1 1 d D . . . .
C6 C 0.5254(5) 0.7354(9) 0.6473(4) 0.022(5) Uani 1 1 d D . . . .
H6 H 0.498596 0.766230 0.667234 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6062(5) 0.6385(11) 0.5900(4) 0.027(4) Uani 1 1 d D . . . .
N2 N 0.7458(4) 0.6036(7) 0.8408(3) 0.030(5) Uani 1 1 d D . . . .
C13 C 0.4374(6) 0.8151(10) 0.3450(4) 0.026(5) Uani 1 1 d D . . . .
C16 C 0.7139(4) 0.7805(9) 0.8494(3) 0.032(5) Uani 1 1 d D . . . .
H16A H 0.732327 0.910395 0.863422 0.038 Uiso 1 1 calc R U . . .
H16B H 0.698856 0.749835 0.895708 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4790(5) 0.7774(9) 0.4993(4) 0.022(4) Uani 1 1 d D . . . .
C1 C 0.6419(5) 0.5245(8) 0.4793(3) 0.031(6) Uani 1 1 d D . . . .
H1A H 0.628236 0.382264 0.473726 0.038 Uiso 1 1 calc R U . . .
H1B H 0.672412 0.517859 0.464565 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6301(6) 0.8971(8) 0.4205(4) 0.031(7) Uani 1 1 d D . . . .
H12A H 0.608780 0.985826 0.380434 0.046 Uiso 1 1 calc R U . . .
H12B H 0.660069 0.889004 0.405153 0.046 Uiso 1 1 calc R U . . .
H12C H 0.634597 0.957108 0.476497 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6093(6) 0.6764(9) 0.4197(4) 0.029(5) Uani 1 1 d D . . . .
H2 H 0.603493 0.619422 0.361709 0.035 Uiso 1 1 calc R U . . .
C17 C 0.6764(4) 0.8143(8) 0.7690(3) 0.029(5) Uani 1 1 d D . . . .
H17A H 0.654095 0.922169 0.778182 0.035 Uiso 1 1 calc R U . . .
H17B H 0.690924 0.864120 0.724226 0.035 Uiso 1 1 calc R U . . .
C15 C 0.7187(4) 0.4074(8) 0.8160(3) 0.025(5) Uani 1 1 d D . . . .
H15A H 0.702187 0.368578 0.859459 0.031 Uiso 1 1 calc R U . . .
H15B H 0.740193 0.291975 0.810846 0.031 Uiso 1 1 calc R U . . .
C18 C 0.7818(5) 0.5704(10) 0.9194(4) 0.043(6) Uani 1 1 d D . . . .
H18A H 0.801251 0.695724 0.932011 0.065 Uiso 1 1 calc R U . . .
H18B H 0.801145 0.450185 0.912924 0.065 Uiso 1 1 calc R U . . .
H18C H 0.766587 0.543610 0.965198 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6834(4) 0.4394(9) 0.7323(3) 0.029(5) Uani 1 1 d D . . . .
H14A H 0.699701 0.476793 0.688386 0.035 Uiso 1 1 calc R U . . .
H14B H 0.665646 0.308721 0.715478 0.035 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 C7 1.372(6) . ?
O1 C9 1.377(14) . ?
O1 C1 1.453(6) . ?
O4 C13 1.223(6) . ?
C11 C10 1.381(13) . ?
C11 C6 1.410(7) . ?
C11 C5 1.458(11) . ?
O2 C5 1.236(13) . ?
N3 C3 1.328(16) . ?
N3 C10 1.403(7) . ?
N3 C2 1.481(16) . ?
N1 C8 1.409(16) . ?
N1 C14 1.464(11) . ?
N1 C17 1.476(10) . ?
C7 C6 1.354(16) . ?
C7 C8 1.382(17) . ?
C10 C9 1.370(15) . ?
C3 C4 1.366(17) . ?
C3 H3 0.9300 . ?
C8 C9 1.412(8) . ?
O3 C13 1.310(15) . ?
O3 H3A 0.8200 . ?
C4 C5 1.430(8) . ?
C4 C13 1.480(14) . ?
C6 H6 0.9300 . ?
N2 C18 1.457(9) . ?
N2 C15 1.461(10) . ?
N2 C16 1.469(11) . ?
C16 C17 1.502(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.514(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.505(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.506(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 O1 C1 114.2(9) . . ?
C10 C11 C6 119.5(10) . . ?
C10 C11 C5 121.7(6) . . ?
C6 C11 C5 118.8(9) . . ?
C3 N3 C10 118.8(11) . . ?
C3 N3 C2 122.1(6) . . ?
C10 N3 C2 118.5(11) . . ?
C8 N1 C14 118.5(6) . . ?
C8 N1 C17 111.4(6) . . ?
C14 N1 C17 112.3(10) . . ?
C6 C7 F1 117.8(10) . . ?
C6 C7 C8 126.1(7) . . ?
F1 C7 C8 116.0(11) . . ?
C9 C10 C11 120.9(6) . . ?
C9 C10 N3 119.2(11) . . ?
C11 C10 N3 119.8(11) . . ?
N3 C3 C4 124.8(7) . . ?
N3 C3 H3 117.6 . . ?
C4 C3 H3 117.6 . . ?
C7 C8 N1 119.0(6) . . ?
C7 C8 C9 114.8(12) . . ?
N1 C8 C9 126.1(12) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.1(12) . . ?
C3 C4 C13 120.5(7) . . ?
C5 C4 C13 119.4(11) . . ?
C7 C6 C11 117.1(11) . . ?
C7 C6 H6 121.4 . . ?
C11 C6 H6 121.4 . . ?
C10 C9 O1 123.0(6) . . ?
C10 C9 C8 121.4(11) . . ?
O1 C9 C8 115.5(11) . . ?
C18 N2 C15 110.4(5) . . ?
C18 N2 C16 111.2(5) . . ?
C15 N2 C16 110.5(9) . . ?
O4 C13 O3 121.2(12) . . ?
O4 C13 C4 123.4(11) . . ?
O3 C13 C4 115.4(7) . . ?
N2 C16 C17 111.6(5) . . ?
N2 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N2 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
O2 C5 C4 124.1(12) . . ?
O2 C5 C11 121.1(7) . . ?
C4 C5 C11 114.8(10) . . ?
O1 C1 C2 109.4(6) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C12 109.6(8) . . ?
N3 C2 C1 108.4(7) . . ?
C12 C2 C1 112.5(11) . . ?
N3 C2 H2 108.8 . . ?
C12 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
N1 C17 C16 109.6(6) . . ?
N1 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N1 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
N2 C15 C14 110.1(5) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 108.1(5) . . ?
N1 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
N1 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
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
C6 C11 C10 C9 0.0(10) . . . . ?
C5 C11 C10 C9 179.5(7) . . . . ?
C6 C11 C10 N3 -176.2(6) . . . . ?
C5 C11 C10 N3 3.3(9) . . . . ?
C3 N3 C10 C9 -179.5(7) . . . . ?
C2 N3 C10 C9 -7.9(9) . . . . ?
C3 N3 C10 C11 -3.3(11) . . . . ?
C2 N3 C10 C11 168.4(6) . . . . ?
C10 N3 C3 C4 0.8(12) . . . . ?
C2 N3 C3 C4 -170.6(6) . . . . ?
C6 C7 C8 N1 178.2(7) . . . . ?
F1 C7 C8 N1 -1.1(10) . . . . ?
C6 C7 C8 C9 0.1(12) . . . . ?
F1 C7 C8 C9 -179.2(5) . . . . ?
C14 N1 C8 C7 140.1(7) . . . . ?
C17 N1 C8 C7 -87.3(9) . . . . ?
C14 N1 C8 C9 -42.0(10) . . . . ?
C17 N1 C8 C9 90.6(8) . . . . ?
N3 C3 C4 C5 1.8(12) . . . . ?
N3 C3 C4 C13 -179.1(7) . . . . ?
F1 C7 C6 C11 178.6(5) . . . . ?
C8 C7 C6 C11 -0.7(12) . . . . ?
C10 C11 C6 C7 0.6(10) . . . . ?
C5 C11 C6 C7 -178.8(6) . . . . ?
C11 C10 C9 O1 -177.0(6) . . . . ?
N3 C10 C9 O1 -0.8(11) . . . . ?
C11 C10 C9 C8 -0.7(11) . . . . ?
N3 C10 C9 C8 175.6(6) . . . . ?
C1 O1 C9 C10 -22.7(9) . . . . ?
C1 O1 C9 C8 160.8(5) . . . . ?
C7 C8 C9 C10 0.6(11) . . . . ?
N1 C8 C9 C10 -177.4(7) . . . . ?
C7 C8 C9 O1 177.2(6) . . . . ?
N1 C8 C9 O1 -0.8(10) . . . . ?
C3 C4 C13 O4 3.5(11) . . . . ?
C5 C4 C13 O4 -177.4(6) . . . . ?
C3 C4 C13 O3 -175.5(7) . . . . ?
C5 C4 C13 O3 3.6(9) . . . . ?
C18 N2 C16 C17 -179.4(7) . . . . ?
C15 N2 C16 C17 -56.5(7) . . . . ?
C3 C4 C5 O2 177.1(7) . . . . ?
C13 C4 C5 O2 -2.1(11) . . . . ?
C3 C4 C5 C11 -1.8(10) . . . . ?
C13 C4 C5 C11 179.1(5) . . . . ?
C10 C11 C5 O2 -179.6(7) . . . . ?
C6 C11 C5 O2 -0.2(10) . . . . ?
C10 C11 C5 C4 -0.7(9) . . . . ?
C6 C11 C5 C4 178.7(6) . . . . ?
C9 O1 C1 C2 52.0(10) . . . . ?
C3 N3 C2 C12 85.1(9) . . . . ?
C10 N3 C2 C12 -86.3(8) . . . . ?
C3 N3 C2 C1 -151.8(7) . . . . ?
C10 N3 C2 C1 36.8(8) . . . . ?
O1 C1 C2 N3 -57.8(10) . . . . ?
O1 C1 C2 C12 63.6(11) . . . . ?
C8 N1 C17 C16 167.9(7) . . . . ?
C14 N1 C17 C16 -56.5(7) . . . . ?
N2 C16 C17 N1 53.8(9) . . . . ?
C18 N2 C15 C14 -177.0(7) . . . . ?
C16 N2 C15 C14 59.6(7) . . . . ?
C8 N1 C14 C15 -168.3(7) . . . . ?
C17 N1 C14 C15 59.5(7) . . . . ?
N2 C15 C14 N1 -60.4(9) . . . . ?
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.032
_cell_measurement_pressure       2.47


# start Validation Reply Form
_vrf_ATOM007_OFLO_2p47           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT029_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available data.
This is exacerbated by the structure being C2/c.
;
_vrf_PLAT201_OFLO_2p47           
;
RESPONSE: The structure was refined isotropically due to the number of data for high 
pressure structure determination
;
_vrf_PLAT084_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT089_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT250_OFLO_2p47           
;
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.

;
_vrf_PLAT155_OFLO_2p47           
;
RESPONSE: We have followed previous literature for comparison.
;
_vrf_PLAT241_OFLO_2p47           
;
RESPONSE: Structure at high pressure with limitation of data. We have used distance restraints to ensure the 
model is chemically reasonable
;
_vrf_PLAT242_OFLO_2p47           
;
RESPONSE: Structure at high pressure with limitation of data. We have used 
distance restraints to ensure the 
model is chemically reasonable.
;
_vrf_PLAT411_OFLO_2p47           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT414_OFLO_2p47           
;
RESPONSE: Structure at high pressure
;
_vrf_PLAT906_OFLO_2p47           
;
RESPONSE: These can be attributed to the weak data. All other sets are okay.
The most common place for a high value of K is in the lowest-intensity bin in 
the table as is the case here. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of Fo, thus 
the high value of Fo/Fc. This is most obvious in the weakest intensities, 
since the small addition to Fo becomes insignificant in the ratio when Fo 
is large.
;
_vrf_PLAT910_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_PLAT913_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to
the data collected e.g. Tungsten powder rings, diamond reflections.
;
_vrf_THETM01_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT023_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT088_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT210_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data hence
isotropic refinement was the limited of modelling the system.
;
_vrf_PLAT193_OFLO_2p47           
;
RESPONSE: This is a rounding issue. The s.u. on Temperature is 2degC
;
_vrf_PLAT340_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so
impacts on the precision of the bonds lengths
;
_vrf_PLAT911_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;

_vrf_PLAT761_OFLO_2p47           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT762_OFLO_2p47           
;
RESPONSE: Noted, no action taken
;
_vrf_PLAT035_OFLO_2p47           
;
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data. Do not have enough data to provide configuration using
MO radiation
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitrobenzene'
