#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:05:03 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229005 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/98/7229842.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_7229842
loop_
_publ_author_name
'Surov, Artem O.'
'Voronin, Alexander P.'
'Drozd, Ksenia V.'
'Churakov, Andrei V.'
'Roussel, Pascal'
'Perlovich, German L.'
_publ_section_title
;
 Diversity of crystal structures and physicochemical properties of
 ciprofloxacin and norfloxacin salts with fumaric acid
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              755
_journal_paper_doi               10.1039/C7CE02033C
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         '2(C16 H19 F N3 O3), C4 H2 O4, 2(H2 O)'
_chemical_formula_sum            'C36 H44 F2 N6 O12'
_chemical_formula_weight         790.77
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-08-07 deposited with the CCDC.
2017-12-29 downloaded from the CCDC.
;
_cell_angle_alpha                93.6351(9)
_cell_angle_beta                 92.6297(9)
_cell_angle_gamma                110.9168(9)
_cell_formula_units_Z            1
_cell_length_a                   6.7869(4)
_cell_length_b                   9.3544(6)
_cell_length_c                   15.7300(9)
_cell_measurement_reflns_used    5555
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.586
_cell_measurement_theta_min      2.339
_cell_volume                     928.45(10)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10525
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0576P)²+0.2112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                4275
_reflns_number_total             4924
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c7ce02033c2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7229840--7229842.cif.'
_cod_database_code               7229842
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
F1 F 0.47754(10) 0.45281(6) 0.39767(4) 0.02441(15) Uani 1 1 d
O1 O 0.09547(14) -0.38115(10) 0.62947(6) 0.0319(2) Uani 1 1 d
O2 O 0.26627(13) -0.15513(10) 0.70231(5) 0.02678(18) Uani 1 1 d
H2 H 0.320(3) -0.049(2) 0.6880(13) 0.063(6) Uiso 1 1 d
O3 O 0.36892(12) 0.08804(9) 0.62661(5) 0.02219(16) Uani 1 1 d
N1 N 0.07738(13) -0.17237(9) 0.40497(5) 0.01512(16) Uani 1 1 d
N2 N 0.29483(13) 0.28633(9) 0.24754(5) 0.01710(17) Uani 1 1 d
N3 N 0.31196(14) 0.43927(10) 0.09671(5) 0.01851(17) Uani 1 1 d
H31 H 0.288(2) 0.5228(19) 0.0717(10) 0.041(4) Uiso 1 1 d
H32 H 0.357(2) 0.3856(17) 0.0571(9) 0.030(4) Uiso 1 1 d
C1 C 0.17395(16) -0.24217(12) 0.63063(7) 0.0222(2) Uani 1 1 d
C2 C 0.17846(15) -0.15635(11) 0.55407(6) 0.01704(19) Uani 1 1 d
C3 C 0.28159(14) 0.00707(11) 0.55808(6) 0.01596(18) Uani 1 1 d
C4 C -0.02612(16) -0.27295(11) 0.32681(7) 0.0196(2) Uani 1 1 d
C5 C 0.1338(2) -0.31430(13) 0.27620(7) 0.0276(2) Uani 1 1 d
C6 C 0.50105(15) 0.37765(11) 0.21840(6) 0.01839(19) Uani 1 1 d
C7 C 0.47753(16) 0.50543(11) 0.16915(7) 0.0196(2) Uani 1 1 d
C8 C 0.10799(16) 0.33121(11) 0.12448(6) 0.01922(19) Uani 1 1 d
C9 C 0.14369(16) 0.20890(11) 0.17514(6) 0.01782(19) Uani 1 1 d
C10 C 0.08263(15) -0.23749(11) 0.47823(6) 0.01734(19) Uani 1 1 d
C11 C 0.18040(14) -0.01450(10) 0.40203(6) 0.01338(17) Uani 1 1 d
C12 C 0.28189(14) 0.07539(10) 0.47771(6) 0.01377(18) Uani 1 1 d
C13 C 0.38457(15) 0.23504(11) 0.47471(6) 0.01604(18) Uani 1 1 d
C14 C 0.38558(15) 0.29834(10) 0.39935(6) 0.01636(18) Uani 1 1 d
C15 C 0.28994(14) 0.21083(10) 0.32142(6) 0.01474(18) Uani 1 1 d
C16 C 0.18544(14) 0.05378(10) 0.32439(6) 0.01457(18) Uani 1 1 d
H10 H 0.016(2) -0.3448(16) 0.4743(8) 0.025(3) Uiso 1 1 d
H13 H 0.451(2) 0.2961(17) 0.5252(9) 0.032(4) Uiso 1 1 d
H16 H 0.124(2) -0.0057(15) 0.2713(9) 0.022(3) Uiso 1 1 d
H41 H -0.103(2) -0.2217(15) 0.2947(8) 0.023(3) Uiso 1 1 d
H42 H -0.130(2) -0.3623(16) 0.3475(9) 0.024(3) Uiso 1 1 d
H51 H 0.198(3) -0.3780(19) 0.3083(10) 0.041(4) Uiso 1 1 d
H52 H 0.062(3) -0.3726(19) 0.2231(11) 0.042(4) Uiso 1 1 d
H53 H 0.244(3) -0.2240(19) 0.2598(10) 0.037(4) Uiso 1 1 d
H61 H 0.602(2) 0.4202(15) 0.2674(8) 0.021(3) Uiso 1 1 d
H62 H 0.552(2) 0.3070(16) 0.1808(9) 0.024(3) Uiso 1 1 d
H71 H 0.435(2) 0.5737(16) 0.2056(9) 0.023(3) Uiso 1 1 d
H72 H 0.610(2) 0.5606(16) 0.1459(9) 0.024(3) Uiso 1 1 d
H81 H 0.050(2) 0.3906(16) 0.1622(9) 0.024(3) Uiso 1 1 d
H82 H 0.018(2) 0.2870(15) 0.0726(9) 0.025(3) Uiso 1 1 d
H91 H 0.007(2) 0.1468(16) 0.1966(9) 0.026(3) Uiso 1 1 d
H92 H 0.194(2) 0.1414(15) 0.1390(8) 0.021(3) Uiso 1 1 d
O21 O 0.23702(12) 0.69211(8) 0.04637(5) 0.02481(17) Uani 1 1 d
O22 O 0.57198(12) 0.75339(8) 0.01313(5) 0.02310(17) Uani 1 1 d
C21 C 0.40962(16) 0.78555(11) 0.02512(6) 0.01787(19) Uani 1 1 d
C22 C 0.41737(16) 0.94593(11) 0.01341(7) 0.0203(2) Uani 1 1 d
H22 H 0.293(2) 0.9663(17) 0.0244(9) 0.033(4) Uiso 1 1 d
O11 O 0.94769(16) 0.82291(12) 0.12373(6) 0.0381(2) Uani 1 1 d
H11 H 0.838(3) 0.810(2) 0.0853(13) 0.058(5) Uiso 1 1 d
H12 H 1.023(3) 0.767(2) 0.0950(13) 0.071(6) Uiso 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 O2 H2 107.2(11) .
C10 N1 C11 120.18(8) .
C10 N1 C4 118.53(8) .
C11 N1 C4 121.14(8) .
C15 N2 C9 119.12(8) .
C15 N2 C6 118.58(8) .
C9 N2 C6 110.93(8) .
C7 N3 C8 112.75(8) .
C7 N3 H31 107.7(9) .
C8 N3 H31 109.7(10) .
C7 N3 H32 109.9(9) .
C8 N3 H32 107.2(9) .
H31 N3 H32 109.6(13) .
O1 C1 O2 121.42(9) .
O1 C1 C2 123.63(10) .
O2 C1 C2 114.94(9) .
C10 C2 C3 120.16(9) .
C10 C2 C1 118.44(9) .
C3 C2 C1 121.39(9) .
O3 C3 C2 122.86(9) .
O3 C3 C12 121.54(9) .
C2 C3 C12 115.59(8) .
N1 C4 C5 111.02(9) .
N1 C4 H41 108.0(8) .
C5 C4 H41 113.5(8) .
N1 C4 H42 104.5(8) .
C5 C4 H42 112.0(8) .
H41 C4 H42 107.3(11) .
C4 C5 H51 111.8(9) .
C4 C5 H52 108.3(10) .
H51 C5 H52 108.9(13) .
C4 C5 H53 111.7(9) .
H51 C5 H53 109.9(13) .
H52 C5 H53 106.0(13) .
N2 C6 C7 109.09(8) .
N2 C6 H61 109.5(8) .
C7 C6 H61 110.3(8) .
N2 C6 H62 108.5(8) .
C7 C6 H62 111.0(8) .
H61 C6 H62 108.4(11) .
N3 C7 C6 109.96(8) .
N3 C7 H71 108.3(8) .
C6 C7 H71 110.4(8) .
N3 C7 H72 108.4(8) .
C6 C7 H72 109.3(8) .
H71 C7 H72 110.4(11) .
N3 C8 C9 111.17(8) .
N3 C8 H81 107.8(8) .
C9 C8 H81 107.5(8) .
N3 C8 H82 106.1(8) .
C9 C8 H82 111.8(8) .
H81 C8 H82 112.5(11) .
N2 C9 C8 107.88(8) .
N2 C9 H91 109.2(8) .
C8 C9 H91 108.0(8) .
N2 C9 H92 111.7(8) .
C8 C9 H92 110.9(8) .
H91 C9 H92 109.0(11) .
N1 C10 C2 123.68(9) .
N1 C10 H10 115.1(8) .
C2 C10 H10 121.3(8) .
N1 C11 C12 118.91(8) .
N1 C11 C16 120.61(8) .
C12 C11 C16 120.48(8) .
C11 C12 C13 118.80(8) .
C11 C12 C3 121.39(8) .
C13 C12 C3 119.80(8) .
C14 C13 C12 119.63(9) .
C14 C13 H13 121.1(9) .
C12 C13 H13 119.3(9) .
F1 C14 C13 119.22(8) .
F1 C14 C15 117.64(8) .
C13 C14 C15 123.12(8) .
C16 C15 N2 123.45(8) .
C16 C15 C14 117.40(8) .
N2 C15 C14 119.05(8) .
C15 C16 C11 120.54(8) .
C15 C16 H16 117.3(8) .
C11 C16 H16 122.1(8) .
O22 C21 O21 124.67(9) .
O22 C21 C22 118.96(9) .
O21 C21 C22 116.37(9) .
C22 C22 C21 123.46(12) 2_675
C22 C22 H22 120.1(9) 2_675
C21 C22 H22 116.4(9) .
H11 O11 H12 102.1(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C14 1.3567(10) .
O1 C1 1.2148(13) .
O2 C1 1.3346(14) .
O2 H2 0.98(2) .
O3 C3 1.2666(12) .
N1 C10 1.3420(12) .
N1 C11 1.3951(11) .
N1 C4 1.4807(12) .
N2 C15 1.3933(12) .
N2 C9 1.4600(12) .
N2 C6 1.4675(12) .
N3 C7 1.4969(13) .
N3 C8 1.4971(13) .
N3 H31 0.956(17) .
N3 H32 0.908(16) .
C1 C2 1.4847(13) .
C2 C10 1.3725(14) .
C2 C3 1.4320(13) .
C3 C12 1.4521(13) .
C4 C5 1.5169(15) .
C4 H41 0.970(14) .
C4 H42 0.967(14) .
C5 H51 1.001(17) .
C5 H52 0.975(17) .
C5 H53 0.966(16) .
C6 C7 1.5155(13) .
C6 H61 0.970(13) .
C6 H62 1.020(14) .
C7 H71 0.957(14) .
C7 H72 0.965(14) .
C8 C9 1.5161(13) .
C8 H81 0.977(14) .
C8 H82 0.971(14) .
C9 H91 0.990(14) .
C9 H92 0.982(13) .
C10 H10 0.939(14) .
C11 C12 1.4081(12) .
C11 C16 1.4099(13) .
C12 C13 1.4096(12) .
C13 C14 1.3575(13) .
C13 H13 0.941(15) .
C14 C15 1.4193(13) .
C15 C16 1.3897(12) .
C16 H16 0.962(14) .
O21 C21 1.2609(12) .
O22 C21 1.2605(12) .
C21 C22 1.5057(13) .
C22 C22 1.322(2) 2_675
C22 H22 0.950(15) .
O11 H11 0.90(2) .
O11 H12 0.96(2) .
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
O2 H2 O3 0.98(2) 1.60(2) 2.5230(11) 156.0(18) .
N3 H31 O21 0.956(17) 1.803(17) 2.7459(11) 168.4(14) .
N3 H32 O22 0.908(16) 1.858(16) 2.7563(11) 170.0(14) 2_665
O11 H11 O22 0.90(2) 1.97(2) 2.8665(13) 170.4(18) .
O11 H12 O21 0.96(2) 1.99(2) 2.9291(13) 166.9(18) 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_4
O1 C1 C2 C10 2.29(15) .
O2 C1 C2 C10 -178.60(8) .
O1 C1 C2 C3 -177.09(9) .
O2 C1 C2 C3 2.03(14) .
C10 C2 C3 O3 178.59(9) .
C1 C2 C3 O3 -2.04(15) .
C10 C2 C3 C12 -1.95(13) .
C1 C2 C3 C12 177.42(8) .
C10 N1 C4 C5 -93.84(10) .
C11 N1 C4 C5 81.75(11) .
C15 N2 C6 C7 -152.22(8) .
C9 N2 C6 C7 64.49(10) .
C8 N3 C7 C6 51.63(11) .
N2 C6 C7 N3 -56.42(10) .
C7 N3 C8 C9 -52.35(11) .
C15 N2 C9 C8 153.10(8) .
C6 N2 C9 C8 -63.83(10) .
N3 C8 C9 N2 56.72(10) .
C11 N1 C10 C2 2.74(14) .
C4 N1 C10 C2 178.38(9) .
C3 C2 C10 N1 -0.38(15) .
C1 C2 C10 N1 -179.76(8) .
C10 N1 C11 C12 -2.55(13) .
C4 N1 C11 C12 -178.08(8) .
C10 N1 C11 C16 176.58(8) .
C4 N1 C11 C16 1.06(13) .
N1 C11 C12 C13 -179.54(8) .
C16 C11 C12 C13 1.32(13) .
N1 C11 C12 C3 0.14(13) .
C16 C11 C12 C3 -178.99(8) .
O3 C3 C12 C11 -178.50(8) .
C2 C3 C12 C11 2.04(13) .
O3 C3 C12 C13 1.18(14) .
C2 C3 C12 C13 -178.28(8) .
C11 C12 C13 C14 -0.70(14) .
C3 C12 C13 C14 179.61(8) .
C12 C13 C14 F1 177.43(8) .
C12 C13 C14 C15 -1.03(15) .
C9 N2 C15 C16 15.89(14) .
C6 N2 C15 C16 -124.39(10) .
C9 N2 C15 C14 -160.37(9) .
C6 N2 C15 C14 59.36(12) .
F1 C14 C15 C16 -176.39(8) .
C13 C14 C15 C16 2.08(14) .
F1 C14 C15 N2 0.09(13) .
C13 C14 C15 N2 178.56(9) .
N2 C15 C16 C11 -177.72(8) .
C14 C15 C16 C11 -1.41(13) .
N1 C11 C16 C15 -179.35(8) .
C12 C11 C16 C15 -0.24(14) .
O22 C21 C22 C22 3.76(19) 2_675
O21 C21 C22 C22 -176.03(13) 2_675
