#------------------------------------------------------------------------------
#$Date: 2020-03-21 03:54:10 +0100 (Sat 21 de Mar de 2020) $
#$Revision: 249598 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/01/7240152.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_7240152
loop_
_publ_author_name
'Putra, Okky Dwichandra'
'Pettersen, Anna'
'Yonemochi, Etsuo'
'Uekusa, Hidehiro'
_publ_section_title
;
 Structural Origin of Physicochemical Properties Differences upon
 Dehydration and Polymorphic Transformation of Ciprofloxacin Hydrochloride
 Revealed by Structure Determination from Powder X-ray Diffraction Data
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00261E
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         ' C17 H19 F N3 O3, Cl  '
_chemical_formula_sum            'C17 H19 Cl F N3 O3'
_chemical_formula_weight         367.80
_chemical_name_common
'Ciprofloxacin Hydrochloride Anhydrous Form II'
_chemical_name_systematic
'Ciprofloxacin Hydrochloride Anhydrous Form II'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-02-06 deposited with the CCDC.	2020-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.2940(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4523(2)
_cell_length_b                   6.91819(13)
_cell_length_c                   19.4137(4)
_cell_measurement_reflns_used    17887
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.240
_cell_measurement_theta_min      3.620
_cell_volume                     1640.05(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/7 (Sheldrick, 2013)'
_diffrn_ambient_pressure         101.3
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID II'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17887
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.620
_diffrn_source                   'rotating anode X-ray'
_diffrn_source_type              RIGAKU
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'abscor, T.Higashi RIGAKU'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'Diffusion method using Ethanol-Acetone'
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0497
_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)+(0.0705P)²+0.2511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2283
_reflns_number_total             2980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00261e2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240152
_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.
;
_shelx_estimated_absorpt_t_min   0.715
_shelx_estimated_absorpt_t_max   0.930
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
H1B H 0.996(3) 0.744(4) -0.1885(15) 0.053(9) Uiso 1 1 d . . . . .
H1A H 0.912(3) 0.585(5) -0.2153(17) 0.067(10) Uiso 1 1 d . . . . .
H3 H 0.383(3) 0.658(5) 0.1153(18) 0.078(12) Uiso 1 1 d . . . . .
Cl1 Cl 0.85801(6) 0.14352(12) 0.21451(4) 0.0497(3) Uani 1 1 d . . . . .
C1 C 0.78378(18) 0.8185(3) 0.03193(12) 0.0277(5) Uani 1 1 d . . . . .
C2 C 0.69704(19) 0.7804(3) 0.06216(12) 0.0274(5) Uani 1 1 d . . . . .
H2 H 0.7075 0.7588 0.1113 0.033 Uiso 1 1 calc R U . . .
C3 C 0.59040(18) 0.7729(3) 0.01999(11) 0.0237(5) Uani 1 1 d . . . . .
C4 C 0.57851(18) 0.8118(3) -0.05173(11) 0.0220(5) Uani 1 1 d . . . . .
C5 C 0.66929(19) 0.8597(3) -0.08100(12) 0.0251(5) Uani 1 1 d . . . . .
H5 H 0.6585 0.8943 -0.1292 0.030 Uiso 1 1 calc R U . . .
C6 C 0.77532(18) 0.8577(3) -0.04068(12) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.49682(19) 0.7261(3) 0.05085(11) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.39330(18) 0.7146(3) 0.00347(11) 0.0233(5) Uani 1 1 d . . . . .
C9 C 0.38655(18) 0.7510(3) -0.06667(12) 0.0247(5) Uani 1 1 d . . . . .
H9 H 0.3168 0.7440 -0.0969 0.030 Uiso 1 1 calc R U . . .
C10 C 0.2913(2) 0.6627(3) 0.02846(13) 0.0291(6) Uani 1 1 d . . . . .
C11 C 0.45866(19) 0.8371(3) -0.16982(11) 0.0261(5) Uani 1 1 d . . . . .
H11 H 0.4518 0.9766 -0.1835 0.031 Uiso 1 1 calc R U . . .
C12 C 0.5139(2) 0.7094(4) -0.21482(12) 0.0309(6) Uani 1 1 d . . . . .
H12A H 0.5414 0.7702 -0.2542 0.037 Uiso 1 1 calc R U . . .
H12B H 0.5589 0.6009 -0.1917 0.037 Uiso 1 1 calc R U . . .
C13 C 0.3924(2) 0.6980(4) -0.22013(13) 0.0343(6) Uani 1 1 d . . . . .
H13A H 0.3450 0.7518 -0.2628 0.041 Uiso 1 1 calc R U . . .
H13B H 0.3626 0.5825 -0.2003 0.041 Uiso 1 1 calc R U . . .
C14 C 0.96228(19) 0.7684(4) -0.05426(13) 0.0327(6) Uani 1 1 d . . . . .
H14A H 0.9699 0.7138 -0.0064 0.039 Uiso 1 1 calc R U . . .
H14B H 1.0299 0.8415 -0.0564 0.039 Uiso 1 1 calc R U . . .
C15 C 0.9492(2) 0.6051(4) -0.10727(13) 0.0355(6) Uani 1 1 d . . . . .
H15A H 1.0154 0.5226 -0.0983 0.043 Uiso 1 1 calc R U . . .
H15B H 0.8856 0.5243 -0.1022 0.043 Uiso 1 1 calc R U . . .
C16 C 0.8404(2) 0.8264(4) -0.19558(14) 0.0375(7) Uani 1 1 d . . . . .
H16A H 0.7698 0.7591 -0.1974 0.045 Uiso 1 1 calc R U . . .
H16B H 0.8391 0.8877 -0.2418 0.045 Uiso 1 1 calc R U . . .
C17 C 0.85533(19) 0.9807(4) -0.13860(12) 0.0319(6) Uani 1 1 d . . . . .
H17A H 0.9209 1.0588 -0.1416 0.038 Uiso 1 1 calc R U . . .
H17B H 0.7911 1.0680 -0.1473 0.038 Uiso 1 1 calc R U . . .
F1 F 0.88485(11) 0.8233(2) 0.07412(7) 0.0380(4) Uani 1 1 d . . . . .
N1 N 0.47410(15) 0.7963(3) -0.09487(9) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.86785(15) 0.9006(3) -0.06782(10) 0.0291(5) Uani 1 1 d . . . . .
N3 N 0.93239(19) 0.6839(4) -0.18033(12) 0.0366(5) Uani 1 1 d . . . . .
O1 O 0.50728(13) 0.6953(2) 0.11657(8) 0.0320(4) Uani 1 1 d . . . . .
O2 O 0.30464(16) 0.6390(2) 0.09825(9) 0.0347(4) Uani 1 1 d . . . . .
O3 O 0.20288(14) 0.6418(3) -0.00955(9) 0.0378(5) Uani 1 1 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 '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
C2 C1 F1 117.8(2) . . ?
C2 C1 C6 123.9(2) . . ?
F1 C1 C6 118.2(2) . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 118.2(2) . . ?
C4 C3 C7 121.2(2) . . ?
C2 C3 C7 120.5(2) . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 N1 118.96(19) . . ?
C5 C4 N1 120.1(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N2 C6 C5 123.3(2) . . ?
N2 C6 C1 120.8(2) . . ?
C5 C6 C1 115.9(2) . . ?
O1 C7 C8 122.4(2) . . ?
O1 C7 C3 121.3(2) . . ?
C8 C7 C3 116.3(2) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 C10 118.5(2) . . ?
C7 C8 C10 121.5(2) . . ?
N1 C9 C8 123.3(2) . . ?
N1 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
O3 C10 O2 121.4(2) . . ?
O3 C10 C8 124.3(2) . . ?
O2 C10 C8 114.4(2) . . ?
N1 C11 C13 118.3(2) . . ?
N1 C11 C12 118.77(19) . . ?
C13 C11 C12 59.95(16) . . ?
N1 C11 H11 116.0 . . ?
C13 C11 H11 116.0 . . ?
C12 C11 H11 116.0 . . ?
C13 C12 C11 59.94(16) . . ?
C13 C12 H12A 117.8 . . ?
C11 C12 H12A 117.8 . . ?
C13 C12 H12B 117.8 . . ?
C11 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C11 C13 C12 60.11(15) . . ?
C11 C13 H13A 117.8 . . ?
C12 C13 H13A 117.8 . . ?
C11 C13 H13B 117.8 . . ?
C12 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
N2 C14 C15 111.46(19) . . ?
N2 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 110.4(2) . . ?
N3 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N3 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 109.8(2) . . ?
N3 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
N3 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N2 C17 C16 113.1(2) . . ?
N2 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
N2 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C9 N1 C4 120.16(19) . . ?
C9 N1 C11 119.40(18) . . ?
C4 N1 C11 120.38(18) . . ?
C6 N2 C17 119.59(18) . . ?
C6 N2 C14 119.5(2) . . ?
C17 N2 C14 109.76(18) . . ?
C15 N3 C16 112.78(19) . . ?
C15 N3 H1B 110.9(18) . . ?
C16 N3 H1B 108.3(18) . . ?
C15 N3 H1A 112.4(19) . . ?
C16 N3 H1A 104.0(19) . . ?
H1B N3 H1A 108(3) . . ?
C10 O2 H3 104(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.352(3) . ?
C1 F1 1.361(2) . ?
C1 C6 1.419(3) . ?
C2 C3 1.418(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(3) . ?
C3 C7 1.447(3) . ?
C4 C5 1.401(3) . ?
C4 N1 1.406(3) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 N2 1.390(3) . ?
C7 O1 1.275(3) . ?
C7 C8 1.432(3) . ?
C8 C9 1.371(3) . ?
C8 C10 1.490(3) . ?
C9 N1 1.349(3) . ?
C9 H9 0.9500 . ?
C10 O3 1.208(3) . ?
C10 O2 1.342(3) . ?
C11 N1 1.457(3) . ?
C11 C13 1.498(3) . ?
C11 C12 1.501(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.498(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N2 1.472(3) . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N3 1.495(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.496(3) . ?
C16 C17 1.522(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N2 1.461(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N3 H1B 0.93(3) . ?
N3 H1A 0.96(3) . ?
O2 H3 0.97(4) . ?
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
N3 H1A Cl1 0.96(3) 2.11(4) 3.069(3) 174(3) 4_565
O2 H3 O1 0.97(4) 1.57(4) 2.509(2) 161(3) .
C12 H12A O1 0.99 2.47 3.324(3) 143.8 4_575
C14 H14A F1 0.99 2.19 2.868(3) 124.6 .
C9 H9 O3 0.95 2.52 2.833(3) 99.5 .
C14 H14B O3 0.99 2.57 3.079(3) 111.8 1_655
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 C1 C2 C3 -179.6(2) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
C1 C2 C3 C7 178.0(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C7 C3 C4 C5 179.1(2) . . . . ?
C2 C3 C4 N1 177.1(2) . . . . ?
C7 C3 C4 N1 -2.9(3) . . . . ?
C3 C4 C5 C6 4.3(3) . . . . ?
N1 C4 C5 C6 -173.70(19) . . . . ?
C4 C5 C6 N2 178.7(2) . . . . ?
C4 C5 C6 C1 -4.4(3) . . . . ?
C2 C1 C6 N2 178.3(2) . . . . ?
F1 C1 C6 N2 -0.2(3) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
F1 C1 C6 C5 -177.13(19) . . . . ?
C4 C3 C7 O1 -178.2(2) . . . . ?
C2 C3 C7 O1 1.7(3) . . . . ?
C4 C3 C7 C8 2.4(3) . . . . ?
C2 C3 C7 C8 -177.6(2) . . . . ?
O1 C7 C8 C9 179.4(2) . . . . ?
C3 C7 C8 C9 -1.3(3) . . . . ?
O1 C7 C8 C10 -0.9(3) . . . . ?
C3 C7 C8 C10 178.4(2) . . . . ?
C7 C8 C9 N1 0.8(3) . . . . ?
C10 C8 C9 N1 -179.0(2) . . . . ?
C9 C8 C10 O3 3.5(3) . . . . ?
C7 C8 C10 O3 -176.3(2) . . . . ?
C9 C8 C10 O2 -176.9(2) . . . . ?
C7 C8 C10 O2 3.4(3) . . . . ?
N1 C11 C12 C13 107.9(2) . . . . ?
N1 C11 C13 C12 -108.6(2) . . . . ?
N2 C14 C15 N3 56.4(3) . . . . ?
N3 C16 C17 N2 -54.3(3) . . . . ?
C8 C9 N1 C4 -1.2(3) . . . . ?
C8 C9 N1 C11 -178.6(2) . . . . ?
C3 C4 N1 C9 2.2(3) . . . . ?
C5 C4 N1 C9 -179.7(2) . . . . ?
C3 C4 N1 C11 179.6(2) . . . . ?
C5 C4 N1 C11 -2.3(3) . . . . ?
C13 C11 N1 C9 -49.0(3) . . . . ?
C12 C11 N1 C9 -118.3(2) . . . . ?
C13 C11 N1 C4 133.7(2) . . . . ?
C12 C11 N1 C4 64.3(3) . . . . ?
C5 C6 N2 C17 9.8(3) . . . . ?
C1 C6 N2 C17 -166.8(2) . . . . ?
C5 C6 N2 C14 -130.3(2) . . . . ?
C1 C6 N2 C14 53.1(3) . . . . ?
C16 C17 N2 C6 -85.7(3) . . . . ?
C16 C17 N2 C14 58.0(2) . . . . ?
C15 C14 N2 C6 85.1(3) . . . . ?
C15 C14 N2 C17 -58.5(3) . . . . ?
C14 C15 N3 C16 -53.4(3) . . . . ?
C17 C16 N3 C15 51.6(3) . . . . ?
