#------------------------------------------------------------------------------
#$Date: 2020-09-06 12:35:05 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/47/7704738.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7704738
loop_
_publ_author_name
'Chrysouli, M. P.'
'Banti, C. N.'
'Kourkoumelis, N.'
'Moushi, E. E.'
'Tasiopoulos, A. J.'
'Douvalis, A.'
'Papachristodoulou, C.'
'Hatzidimitriou, A. G.'
'Bakas, T.'
'Hadjikakou, S. K.'
_publ_section_title
;
 Ciprofloxacin conjugated to diphenyltin(IV): a novel formulation with
 enhanced antimicrobial activity.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11522
_journal_page_last               11535
_journal_paper_doi               10.1039/d0dt01665a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C17 H18 F N3 O3'
_chemical_formula_sum            'C17 H18 F N3 O3'
_chemical_formula_weight         331.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-05-07 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                87.440(7)
_cell_angle_beta                 84.496(7)
_cell_angle_gamma                88.912(7)
_cell_formula_units_Z            2
_cell_length_a                   7.8945(7)
_cell_length_b                   8.5010(7)
_cell_length_c                   10.7522(9)
_cell_measurement_reflns_used    1599
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8520
_cell_measurement_theta_min      4.0850
_cell_volume                     717.47(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4223
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4189
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.993
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_min         4.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       Polyhedral
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0511
_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)+(0.0632P)²+0.4091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1996
_reflns_number_total             2531
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01665a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7704737--7704738.cif.'
_cod_database_code               7704738
_shelx_shelxl_version_number     2014/7
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.691
_oxdiff_exptl_absorpt_empirical_full_max 1.909
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7362(3) 0.2773(3) 0.7555(2) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.8040(3) 0.1989(3) 0.6437(2) 0.0166(5) Uani 1 1 d . . . . .
C3 C 0.6820(3) 0.1883(3) 0.5492(2) 0.0162(5) Uani 1 1 d . . . . .
C4 C 0.5164(3) 0.2518(3) 0.5658(2) 0.0159(5) Uani 1 1 d . . . . .
C5 C 0.5721(3) 0.3321(3) 0.7656(2) 0.0163(5) Uani 1 1 d . . . . .
H5 H 0.5330 0.3808 0.8388 0.020 Uiso 1 1 calc R U . . .
C6 C 0.7290(3) 0.1115(3) 0.4377(2) 0.0166(5) Uani 1 1 d . . . . .
H6 H 0.8363 0.0645 0.4250 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6191(3) 0.1054(3) 0.3484(2) 0.0164(5) Uani 1 1 d . . . . .
C8 C 0.4546(3) 0.1762(3) 0.3591(2) 0.0166(5) Uani 1 1 d . . . . .
C9 C 0.4065(3) 0.2473(3) 0.4714(2) 0.0167(5) Uani 1 1 d . . . . .
H9 H 0.2985 0.2930 0.4840 0.020 Uiso 1 1 calc R U . . .
C10 C 0.4125(3) 0.2162(3) 0.1381(2) 0.0180(5) Uani 1 1 d . . . . .
H10A H 0.5235 0.1676 0.1185 0.022 Uiso 1 1 calc R U . . .
H10B H 0.4263 0.3295 0.1339 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2938(3) 0.1713(3) 0.0433(2) 0.0196(5) Uani 1 1 d . . . . .
H11A H 0.3397 0.2066 -0.0400 0.023 Uiso 1 1 calc R U . . .
H11B H 0.2834 0.0577 0.0448 0.023 Uiso 1 1 calc R U . . .
C12 C 0.0534(3) 0.1854(3) 0.1994(2) 0.0172(5) Uani 1 1 d . . . . .
H12A H 0.0411 0.0720 0.1995 0.021 Uiso 1 1 calc R U . . .
H12B H -0.0583 0.2322 0.2199 0.021 Uiso 1 1 calc R U . . .
C13 C 0.1714(3) 0.2263(3) 0.2966(2) 0.0174(5) Uani 1 1 d . . . . .
H13A H 0.1753 0.3399 0.3014 0.021 Uiso 1 1 calc R U . . .
H13B H 0.1268 0.1830 0.3779 0.021 Uiso 1 1 calc R U . . .
C14 C 0.8359(3) 0.2985(3) 0.8664(2) 0.0175(5) Uani 1 1 d . . . . .
C15 C 0.2808(3) 0.3495(3) 0.7100(2) 0.0169(5) Uani 1 1 d . . . . .
H15 H 0.2118 0.2549 0.7265 0.020 Uiso 1 1 calc R U . . .
C16 C 0.1941(3) 0.4874(3) 0.6508(2) 0.0210(5) Uani 1 1 d . . . . .
H16A H 0.0781 0.4743 0.6310 0.025 Uiso 1 1 calc R U . . .
H16B H 0.2627 0.5562 0.5926 0.025 Uiso 1 1 calc R U . . .
C17 C 0.2257(3) 0.4869(3) 0.7870(2) 0.0204(5) Uani 1 1 d . . . . .
H17A H 0.3132 0.5553 0.8105 0.024 Uiso 1 1 calc R U . . .
H17B H 0.1286 0.4735 0.8488 0.024 Uiso 1 1 calc R U . . .
N1 N 0.4618(3) 0.3212(2) 0.67766(19) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.3438(3) 0.1642(2) 0.26578(19) 0.0171(4) Uani 1 1 d . . . . .
N3 N 0.1243(3) 0.2452(3) 0.0736(2) 0.0184(5) Uani 1 1 d D . . . .
O1 O 0.8127(2) 0.4222(2) 0.92428(17) 0.0227(4) Uani 1 1 d . . . . .
O2 O 0.9335(2) 0.1855(2) 0.89512(17) 0.0230(4) Uani 1 1 d . . . . .
O3 O 0.9525(2) 0.1495(2) 0.62332(17) 0.0206(4) Uani 1 1 d . . . . .
F1 F 0.66601(18) 0.02157(16) 0.24552(13) 0.0197(3) Uani 1 1 d . . . . .
H3A H 0.135(5) 0.353(4) 0.076(3) 0.039(10) Uiso 1 1 d . . . . .
H3B H 0.055(3) 0.225(4) 0.019(2) 0.029(8) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 119.8(2) . . ?
C5 C1 C14 116.5(2) . . ?
C2 C1 C14 123.7(2) . . ?
O3 C2 C1 125.0(2) . . ?
O3 C2 C3 120.9(2) . . ?
C1 C2 C3 114.0(2) . . ?
C4 C3 C6 117.5(2) . . ?
C4 C3 C2 122.4(2) . . ?
C6 C3 C2 120.1(2) . . ?
N1 C4 C9 119.7(2) . . ?
N1 C4 C3 119.3(2) . . ?
C9 C4 C3 121.0(2) . . ?
N1 C5 C1 125.3(2) . . ?
N1 C5 H5 117.4 . . ?
C1 C5 H5 117.4 . . ?
C7 C6 C3 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C3 C6 H6 119.8 . . ?
C6 C7 F1 118.4(2) . . ?
C6 C7 C8 123.4(2) . . ?
F1 C7 C8 118.1(2) . . ?
C9 C8 N2 122.5(2) . . ?
C9 C8 C7 115.8(2) . . ?
N2 C8 C7 121.5(2) . . ?
C8 C9 C4 121.6(2) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
N2 C10 C11 110.48(19) . . ?
N2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N3 C11 C10 109.5(2) . . ?
N3 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N3 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
N3 C12 C13 109.79(19) . . ?
N3 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 C12 111.4(2) . . ?
N2 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O1 C14 O2 125.3(2) . . ?
O1 C14 C1 118.2(2) . . ?
O2 C14 C1 116.5(2) . . ?
N1 C15 C16 119.8(2) . . ?
N1 C15 C17 119.0(2) . . ?
C16 C15 C17 60.58(16) . . ?
N1 C15 H15 115.5 . . ?
C16 C15 H15 115.5 . . ?
C17 C15 H15 115.5 . . ?
C15 C16 C17 59.77(16) . . ?
C15 C16 H16A 117.8 . . ?
C17 C16 H16A 117.8 . . ?
C15 C16 H16B 117.8 . . ?
C17 C16 H16B 117.8 . . ?
H16A C16 H16B 114.9 . . ?
C15 C17 C16 59.65(16) . . ?
C15 C17 H17A 117.8 . . ?
C16 C17 H17A 117.8 . . ?
C15 C17 H17B 117.8 . . ?
C16 C17 H17B 117.8 . . ?
H17A C17 H17B 114.9 . . ?
C5 N1 C4 119.1(2) . . ?
C5 N1 C15 119.9(2) . . ?
C4 N1 C15 119.6(2) . . ?
C8 N2 C13 115.3(2) . . ?
C8 N2 C10 115.70(19) . . ?
C13 N2 C10 111.57(18) . . ?
C11 N3 C12 108.97(18) . . ?
C11 N3 H3A 110(2) . . ?
C12 N3 H3A 108(2) . . ?
C11 N3 H3B 112(2) . . ?
C12 N3 H3B 110(2) . . ?
H3A N3 H3B 109(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.364(3) . ?
C1 C2 1.453(3) . ?
C1 C14 1.509(3) . ?
C2 O3 1.240(3) . ?
C2 C3 1.472(3) . ?
C3 C4 1.403(3) . ?
C3 C6 1.406(4) . ?
C4 N1 1.391(3) . ?
C4 C9 1.400(4) . ?
C5 N1 1.353(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.358(4) . ?
C6 H6 0.9300 . ?
C7 F1 1.360(3) . ?
C7 C8 1.417(3) . ?
C8 C9 1.391(4) . ?
C8 N2 1.402(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.479(3) . ?
C10 C11 1.515(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.482(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.485(3) . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.464(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O1 1.248(3) . ?
C14 O2 1.266(3) . ?
C15 N1 1.456(3) . ?
C15 C16 1.495(3) . ?
C15 C17 1.497(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.509(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N3 H3A 0.92(4) . ?
N3 H3B 0.862(10) . ?
