#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:59:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180406 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/75/7207511.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_7207511
loop_
_publ_author_name
'Holstein, Julian Jacob'
'Hübschle, Christian Bertram'
'Dittrich, Birger'
_publ_section_title
;
 Electrostatic properties of nine fluoroquinolone antibiotics derived
 directly from their crystal structure refinements
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2520
_journal_paper_doi               10.1039/c1ce05966a
_journal_volume                  14
_journal_year                    2012
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_moiety         'C16 H18 F N3 O3, 2(H2 O)'
_chemical_formula_sum            'C16 H22 F N3 O5'
_chemical_formula_weight         355.37
_chemical_name_common            Norfloxacin
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.6920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2477(6)
_cell_length_b                   21.6745(17)
_cell_length_c                   9.5199(7)
_cell_measurement_reflns_used    32868
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.27
_cell_measurement_theta_min      1.88
_cell_volume                     1592.0(2)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2008)'
_computing_molecular_graphics    'MolecoolQt (Huebschle et al, 2011)'
_computing_publication_material  'enCIFer 1.3, CCDC, 2008'
_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Apex 2 Diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_UB_11      -1.1892086e-001
_diffrn_orient_matrix_UB_12      -1.7360093e-003
_diffrn_orient_matrix_UB_13      -7.7544421e-002
_diffrn_orient_matrix_UB_21      5.0222732e-002
_diffrn_orient_matrix_UB_22      1.7276448e-003
_diffrn_orient_matrix_UB_23      -8.0976017e-002
_diffrn_orient_matrix_UB_31      6.3700578e-003
_diffrn_orient_matrix_UB_32      -4.6030153e-002
_diffrn_orient_matrix_UB_33      -1.1470664e-004
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32868
_diffrn_reflns_theta_full        33.27
_diffrn_reflns_theta_max         33.27
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS version 2008/2, multi-scan. (G. M. Sheldrick, 2008)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.1753
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4059
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
calc w1 = 1/[s²(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0261
_reflns_number_gt                4059
_reflns_number_total             6042
_reflns_threshold_expression     F>3(σ)F
_cod_data_source_file            c1ce05966a.txt
_cod_data_source_block           nor
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7207511
#BEGIN Tags that were not found in dictionaries:
_computing_aspherical_atom_model 'Invariomtool (Huebschle et al, 2007)'
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
F(15) C(6) Z F(15) C(5) Y
O(13) C(11) X O(13) O(12) Y
O(12) C(11) X O(12) O(13) Y
O(14) C(4) X O(14) C(3) Y
O(2) DUM1 Z O(2) H(022) Y
O(3) DUM2 Z O(3) H(031) Y
N(23) DUM3 Z N(23) C(24) Y
N(1) C(2) X N(1) C(9) Y
N(20) C(7) X N(20) DUM4 Y
C(6) F(15) X C(6) C(5) Y
C(11) O(12) X C(11) O(13) Y
C(4) O(14) X C(4) C(3) Y
C(3) C(2) X C(3) C(4) Y
C(10) C(9) X C(10) C(5) Y
C(5) C(6) X C(5) C(10) Y
C(2) N(1) X C(2) C(3) Y
C(9) N(1) X C(9) C(10) Y
C(8) C(7) X C(8) C(9) Y
C(7) N(20) X C(7) C(8) Y
C(16) N(1) X C(16) C(17) Y
C(25) N(20) X C(25) C(24) Y
C(21) N(20) X C(21) C(22) Y
C(24) N(23) X C(24) C(25) Y
C(22) N(23) X C(22) C(21) Y
C(17) C(16) Z C(17) H(17A) X
H(23A) N(23) Z H(23A) C(24) Y
H(23B) N(23) Z H(23B) C(24) Y
H(5) C(5) Z H(5) C(6) Y
H(2) C(2) Z H(2) C(3) Y
H(8) C(8) Z H(8) C(7) Y
H(16A) C(16) Z H(16A) N(1) Y
H(16B) C(16) Z H(16B) N(1) Y
H(25A) C(25) Z H(25A) N(20) Y
H(25B) C(25) Z H(25B) N(20) Y
H(21A) C(21) Z H(21A) N(20) Y
H(21B) C(21) Z H(21B) N(20) Y
H(24A) C(24) Z H(24A) N(23) Y
H(24B) C(24) Z H(24B) N(23) Y
H(22A) C(22) Z H(22A) N(23) Y
H(22B) C(22) Z H(22B) N(23) Y
H(17A) C(17) Z H(17A) C(16) Y
H(17B) C(17) Z H(17B) C(16) Y
H(17C) C(17) Z H(17C) C(16) Y
H(21) O(2) Z H(021) H(022) Y
H(22) O(2) Z H(022) H(021) Y
H(31) O(3) Z H(031) H(032) Y
H(32) O(3) Z H(032) H(031) Y
loop_
_atom_rho_multipole_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa_prime
_atom_rho_multipole_kappa_dprime0
_atom_rho_multipole_kappa_dprime1
_atom_rho_multipole_kappa_dprime2
_atom_rho_multipole_kappa_dprime3
_atom_rho_multipole_kappa_dprime4
F(15) 7.09 0.00 0.00 0.00 -0.07 -0.11 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.00 1.18 1.20 1.20
1.20 1.20
O(13) 6.27 0.00 -0.08 0.00 0.00 -0.06 0.00 0.00 -0.07 0.00 0.00 -0.01 0.00 0.00
0.00 0.03 0.01 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.01 0.99 1.14 1.20
1.20 1.20 1.20
O(12) 6.27 0.00 -0.08 0.00 0.00 -0.06 0.00 0.00 -0.07 0.00 0.00 -0.01 0.00 0.00
0.00 0.03 0.01 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.01 0.99 1.14 1.20
1.20 1.20 1.20
O(14) 6.15 0.00 -0.08 0.00 0.00 -0.11 0.00 0.00 -0.07 0.00 0.00 -0.01 0.00 0.00
0.00 0.04 0.00 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.00 1.15 1.20
1.20 1.20 1.20
O(2) 5.77 0.00 0.00 0.00 -0.14 -0.01 0.00 0.00 0.12 0.00 -0.04 0.00 0.00 -0.07
0.00 0.00 0.00 -0.02 0.00 0.00 -0.03 0.00 0.00 0.00 0.01 0.00 1.02 1.11 1.20
1.20 1.20 1.20
O(3) 5.77 0.00 0.00 0.00 -0.14 -0.01 0.00 0.00 0.12 0.00 -0.04 0.00 0.00 -0.07
0.00 0.00 0.00 -0.02 0.00 0.00 -0.03 0.00 0.00 0.00 0.01 0.00 1.02 1.11 1.20
1.20 1.20 1.20
N(23) 4.88 0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 -0.22
0.00 0.00 0.00 -0.04 0.00 0.00 0.02 0.00 0.00 0.00 0.03 0.00 1.01 1.14 1.20
1.20 1.20 1.20
N(1) 5.09 0.00 0.01 0.01 0.00 0.03 0.00 0.00 0.01 -0.01 0.00 0.01 0.01 0.00
0.00 0.17 0.01 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.01 0.02 1.01 1.05 1.20 1.20
1.20 1.20
N(20) 5.13 0.00 0.01 -0.04 0.00 -0.06 0.00 0.00 -0.07 0.02 0.00 -0.16 0.04 0.00
0.00 0.04 0.02 0.01 0.00 0.00 0.00 -0.02 0.00 0.00 0.01 0.01 1.00 1.00 1.00
1.00 1.00 1.00
C(6) 4.06 0.00 -0.11 0.03 0.00 -0.11 0.00 0.00 -0.13 -0.03 0.00 -0.07 0.02 0.00
0.00 0.28 0.01 0.03 0.00 0.00 -0.03 -0.01 0.00 0.00 0.04 0.00 1.01 1.00 1.00
1.00 1.00 1.00
C(11) 4.06 0.00 0.02 0.04 0.00 -0.23 0.00 0.00 0.07 -0.08 0.00 0.00 0.00 0.00
0.00 0.28 0.07 0.00 0.00 0.00 0.02 -0.02 0.00 0.00 -0.01 -0.05 1.01 1.00 1.00
1.00 1.00 1.00
C(4) 3.98 0.00 0.06 0.00 0.00 -0.24 0.00 0.00 0.07 0.00 0.00 0.01 0.00 0.00
0.00 0.28 0.00 0.01 0.00 0.00 0.02 0.00 0.00 0.00 -0.02 0.00 1.02 1.00 1.00
1.00 1.00 1.00
C(3) 4.08 0.00 0.02 0.01 0.00 -0.14 0.00 0.00 0.02 0.00 0.00 0.04 0.01 0.00
0.00 0.23 0.00 0.02 0.00 0.00 0.01 0.01 0.00 0.00 0.00 0.00 1.02 1.00 1.00 1.00
1.00 1.00
C(10) 4.05 0.00 0.02 0.00 0.00 -0.15 0.00 0.00 0.02 0.00 0.00 0.01 0.01 0.00
0.00 0.22 0.00 0.02 0.00 0.00 0.01 -0.01 0.00 0.00 0.01 0.01 1.02 1.00 1.00
1.00 1.00 1.00
C(5) 3.94 0.00 0.02 0.02 0.00 -0.15 0.00 0.00 0.00 -0.01 0.00 0.01 0.03 0.00
0.00 0.22 -0.01 0.03 0.00 0.00 0.00 0.00 0.00 0.00 0.01 -0.01 1.02 1.00 1.00
1.00 1.00 1.00
C(2) 3.95 0.00 -0.05 0.04 0.00 -0.16 0.00 0.00 -0.05 -0.06 0.00 -0.03 0.04 0.00
0.00 0.24 0.04 0.02 0.00 0.00 0.00 -0.02 0.00 0.00 0.02 -0.02 1.02 1.00 1.00
1.00 1.00 1.00
C(9) 4.02 0.00 -0.06 0.00 0.00 -0.16 0.00 0.00 -0.06 0.00 0.00 -0.03 0.00 0.00
0.00 0.25 0.01 0.01 0.00 0.00 -0.01 0.00 0.00 0.00 0.01 0.00 1.02 1.00 1.00
1.00 1.00 1.00
C(8) 4.01 0.00 0.02 0.03 0.00 -0.11 0.00 0.00 0.01 -0.02 0.00 0.01 0.02 0.00
0.00 0.22 0.00 0.02 0.00 0.00 0.00 -0.01 0.00 0.00 0.00 0.00 1.02 1.00 1.00
1.00 1.00 1.00
C(7) 4.04 0.00 -0.04 0.03 0.00 -0.17 0.00 0.00 -0.03 -0.03 0.00 -0.04 0.02 0.00
0.00 0.26 0.02 0.01 0.00 0.00 0.01 -0.01 0.00 0.00 0.02 0.00 1.02 1.00 1.00
1.00 1.00 1.00
C(16) 3.92 0.00 -0.05 0.00 0.00 0.05 0.00 0.00 -0.07 -0.01 0.00 -0.13 -0.19
0.00 0.00 0.18 -0.03 0.02 0.00 0.00 -0.05 0.07 0.00 0.00 0.04 0.02 1.01 1.00
1.00 1.00 1.00 1.00
C(25) 3.87 0.00 -0.02 0.01 0.00 0.02 0.00 0.00 -0.03 -0.01 0.00 -0.13 -0.17
0.00 0.00 0.18 -0.04 0.01 0.00 0.00 -0.03 0.07 0.00 0.00 0.03 0.02 1.01 1.00
1.00 1.00 1.00 1.00
C(21) 3.87 0.00 -0.02 0.01 0.00 0.02 0.00 0.00 -0.03 -0.01 0.00 -0.13 -0.17
0.00 0.00 0.18 -0.04 0.01 0.00 0.00 -0.03 0.07 0.00 0.00 0.03 0.02 1.01 1.00
1.00 1.00 1.00 1.00
C(24) 3.87 0.00 -0.02 0.01 0.00 0.02 0.00 0.00 -0.03 -0.01 0.00 -0.13 -0.17
0.00 0.00 0.18 -0.04 0.01 0.00 0.00 -0.03 0.07 0.00 0.00 0.03 0.02 1.01 1.00
1.00 1.00 1.00 1.00
C(22) 3.87 0.00 -0.02 0.01 0.00 0.02 0.00 0.00 -0.03 -0.01 0.00 -0.13 -0.17
0.00 0.00 0.18 -0.04 0.01 0.00 0.00 -0.03 0.07 0.00 0.00 0.03 0.02 1.01 1.00
1.00 1.00 1.00 1.00
C(17) 4.00 0.00 0.00 0.00 -0.01 -0.01 0.00 0.00 0.00 0.00 0.23 0.00 0.00 0.00
0.00 0.19 0.00 0.03 0.00 0.00 0.00 0.00 -0.09 0.00 0.00 0.00 1.01 1.00 1.00
1.00 1.00 1.00
H(23A) 0.81 0.00 0.00 0.00 0.18 0.09 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.18 1.20 1.20 1.20
1.20 0.00
H(23B) 0.81 0.00 0.00 0.00 0.18 0.09 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.18 1.20 1.20 1.20
1.20 0.00
H(5) 0.97 0.00 0.00 0.00 0.15 0.06 0.00 0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.14 1.20 1.20 1.20 1.20
0.00
H(2) 0.97 0.00 0.00 0.00 0.15 0.06 0.00 0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.14 1.20 1.20 1.20 1.20
0.00
H(8) 0.97 0.00 0.00 0.00 0.15 0.06 0.00 0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.14 1.20 1.20 1.20 1.20
0.00
H(16A) 0.95 0.00 0.00 0.00 0.15 0.07 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.15 1.20 1.20 1.20
1.20 1.200000(0)
H(16B) 0.95 0.00 0.00 0.00 0.15 0.07 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.15 1.20 1.20 1.20
1.20 1.200000(0)
H(25A) 1.03 0.00 0.00 0.00 0.15 0.08 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.11 1.20 1.20 1.20
1.20 1.200000(0)
H(25B) 1.03 0.00 0.00 0.00 0.15 0.08 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.11 1.20 1.20 1.20
1.20 1.200000(0)
H(21A) 1.03 0.00 0.00 0.00 0.15 0.08 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.11 1.20 1.20 1.20
1.20 1.200000(0)
H(21B) 1.03 0.00 0.00 0.00 0.15 0.08 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.11 1.20 1.20 1.20
1.20 1.200000(0)
H(24A) 1.03 0.00 0.00 0.00 0.15 0.08 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.11 1.20 1.20 1.20
1.20 1.200000(0)
H(24B) 1.03 0.00 0.00 0.00 0.15 0.08 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.11 1.20 1.20 1.20
1.20 1.200000(0)
H(22A) 1.03 0.00 0.00 0.00 0.15 0.08 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.11 1.20 1.20 1.20
1.20 1.200000(0)
H(22B) 1.03 0.00 0.00 0.00 0.15 0.08 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.11 1.20 1.20 1.20
1.20 1.200000(0)
H(17A) 0.96 0.00 0.00 0.00 0.13 0.05 0.00 0.00 0.00 0.00 0.01 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.14 1.20 1.20 1.20
1.20 1.200000(0)
H(17B) 0.96 0.00 0.00 0.00 0.13 0.05 0.00 0.00 0.00 0.00 0.01 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.14 1.20 1.20 1.20
1.20 1.200000(0)
H(17C) 0.96 0.00 0.00 0.00 0.13 0.05 0.00 0.00 0.00 0.00 0.01 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.14 1.20 1.20 1.20
1.20 1.200000(0)
H(21) 1.11 0.00 0.00 0.00 0.25 0.12 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.05 1.20 1.20
1.20 1.20 1.200000(0)
H(22) 1.11 0.00 0.00 0.00 0.25 0.12 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.05 1.20 1.20
1.20 1.20 1.200000(0)
H(31) 1.11 0.00 0.00 0.00 0.25 0.12 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.05 1.20 1.20
1.20 1.20 1.200000(0)
H(32) 1.11 0.00 0.00 0.00 0.25 0.12 0.00 0.00 0.00 0.00 0.03 0.00 0.00 0.00
0.00 0.00 0.00 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.05 1.20 1.20
1.20 1.20 1.200000(0)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
F(15) -0.18487(4) 0.00797(1) 0.08868(3) 1.0000 0.015
O(13) 0.34294(5) -0.20792(2) 0.71681(4) 1.0000 0.015
O(12) 0.49910(5) -0.14163(2) 0.89217(4) 1.0000 0.023
O(14) 0.07584(5) -0.14814(2) 0.48094(4) 1.0000 0.014
O(2) 0.55288(5) 0.20112(2) 0.55094(5) 1.0000 0.022
O(3) 0.26599(5) 0.27789(2) 0.45730(4) 1.0000 0.022
N(23) -0.04578(6) 0.22610(2) -0.00694(5) 1.0000 0.012
N(1) 0.38052(6) 0.00653(2) 0.61601(5) 1.0000 0.010
N(20) 0.00475(6) 0.11660(2) 0.17176(5) 1.0000 0.011
C(6) -0.04166(7) 0.00805(2) 0.21481(6) 1.0000 0.011
C(11) 0.39251(7) -0.15394(2) 0.76416(6) 1.0000 0.013
C(4) 0.17442(7) -0.10276(2) 0.52404(6) 1.0000 0.010
C(3) 0.32508(7) -0.10019(2) 0.65976(6) 1.0000 0.011
C(10) 0.13945(7) -0.04585(2) 0.43513(6) 1.0000 0.009
C(5) -0.00185(7) -0.04457(2) 0.29877(6) 1.0000 0.010
C(2) 0.41590(7) -0.04572(2) 0.69806(6) 1.0000 0.011
C(9) 0.24031(7) 0.00769(2) 0.48113(5) 1.0000 0.009
C(8) 0.20050(7) 0.06104(2) 0.39072(6) 1.0000 0.010
C(7) 0.05744(7) 0.06283(2) 0.25649(6) 1.0000 0.010
C(16) 0.48930(7) 0.06191(2) 0.67309(6) 1.0000 0.012
C(25) -0.02267(7) 0.11324(2) 0.01092(6) 1.0000 0.014
C(21) 0.09466(7) 0.17334(2) 0.23816(6) 1.0000 0.012
C(24) -0.13407(8) 0.16721(2) -0.07069(6) 1.0000 0.015
C(22) -0.00939(7) 0.22888(2) 0.15823(6) 1.0000 0.013
C(17) 0.40472(7) 0.10860(3) 0.74485(6) 1.0000 0.017
H(23A) 0.06868(6) 0.22911(2) -0.02546(5) 1.0000 0.040(2)
H(23B) -0.11505(6) 0.26432(2) -0.05641(5) 1.0000 0.037(2)
H(5) -0.07972(7) -0.08571(2) 0.26196(6) 1.0000 0.021(2)
H(2) 0.52562(7) -0.04317(2) 0.80223(6) 1.0000 0.020(2)
H(8) 0.28092(7) 0.10167(2) 0.42624(6) 1.0000 0.022(2)
H(16A) 0.52054(7) 0.08160(2) 0.58065(6) 1.0000 0.024(2)
H(16B) 0.61087(7) 0.04404(2) 0.75142(6) 1.0000 0.026(2)
H(25A) -0.08414(7) 0.06893(2) -0.03389(6) 1.0000 0.027(2)
H(25B) 0.10310(7) 0.11434(2) -0.00477(6) 1.0000 0.029(2)
H(21A) 0.22508(7) 0.17643(2) 0.23214(6) 1.0000 0.032(2)
H(21B) 0.10055(7) 0.17485(2) 0.35529(6) 1.0000 0.022(2)
H(24A) -0.15438(8) 0.16558(2) -0.19114(6) 1.0000 0.033(2)
H(24B) -0.25956(8) 0.16619(2) -0.05448(6) 1.0000 0.029(2)
H(22A) -0.13666(7) 0.22956(2) 0.17116(6) 1.0000 0.027(2)
H(22B) 0.05915(7) 0.27228(2) 0.20119(6) 1.0000 0.032(2)
H(17A) 0.48761(7) 0.14921(3) 0.77918(6) 1.0000 0.036(2)
H(17B) 0.38387(7) 0.09092(3) 0.84447(6) 1.0000 0.031(2)
H(17C) 0.28153(7) 0.12484(3) 0.66465(6) 1.0000 0.041(2)
H(21) 0.60583(5) 0.21005(2) 0.47798(5) 1.0000 0.036(2)
H(22) 0.59536(5) 0.23376(2) 0.62307(5) 1.0000 0.040(2)
H(31) 0.33900(5) 0.24196(2) 0.48297(4) 1.0000 0.039(2)
H(32) 0.34226(5) 0.31021(2) 0.51180(4) 1.0000 0.043(2)
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 'Invariom modelling (Acta Cryst. A61, 314--320)'
H H 0.0000 0.0000 'Invariom modelling (Acta Cryst. A61, 314--320)'
N N 0.0061 0.0033 'Invariom modelling (Acta Cryst. A61, 314--320)'
O O 0.0106 0.0060 'Invariom modelling (Acta Cryst. A61, 314--320)'
F F 0.0171 0.0103 'Invariom modelling (Acta Cryst. A61, 314--320)'
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H(21) O(2) H(22) 102.93(6) 1_555 1_555 1_555 yes
H(31) O(3) H(32) 102.79(5) 1_555 1_555 1_555 yes
H(23A) N(23) H(23B) 105.60(6) 1_555 1_555 1_555 yes
C(2) N(1) C(9) 119.27(5) 1_555 1_555 1_555 yes
C(7) N(20) C(25) 117.56(4) 1_555 1_555 1_555 yes
C(7) N(20) C(21) 116.50(4) 1_555 1_555 1_555 yes
C(25) N(20) C(21) 111.16(4) 1_555 1_555 1_555 yes
F(15) C(6) C(5) 118.18(5) 1_555 1_555 1_555 yes
F(15) C(6) C(7) 119.05(4) 1_555 1_555 1_555 yes
C(5) C(6) C(7) 122.75(5) 1_555 1_555 1_555 yes
O(13) C(11) O(12) 124.67(5) 1_555 1_555 1_555 yes
O(13) C(11) C(3) 118.81(5) 1_555 1_555 1_555 yes
O(12) C(11) C(3) 116.48(5) 1_555 1_555 1_555 yes
O(14) C(4) C(3) 125.38(5) 1_555 1_555 1_555 yes
O(14) C(4) C(10) 120.02(5) 1_555 1_555 1_555 yes
C(3) C(4) C(10) 114.59(5) 1_555 1_555 1_555 yes
C(11) C(3) C(4) 124.19(5) 1_555 1_555 1_555 yes
C(11) C(3) C(2) 116.72(5) 1_555 1_555 1_555 yes
C(4) C(3) C(2) 119.09(5) 1_555 1_555 1_555 yes
C(4) C(10) C(5) 118.68(5) 1_555 1_555 1_555 yes
C(4) C(10) C(9) 122.76(5) 1_555 1_555 1_555 yes
C(5) C(10) C(9) 118.56(5) 1_555 1_555 1_555 yes
C(6) C(5) C(10) 120.46(5) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 120.43(3) 1_555 1_555 1_555 yes
C(10) C(5) H(5) 119.10(3) 1_555 1_555 1_555 yes
N(1) C(2) C(3) 125.52(5) 1_555 1_555 1_555 yes
N(1) C(2) H(2) 115.33(3) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 119.15(3) 1_555 1_555 1_555 yes
N(1) C(9) C(10) 118.70(5) 1_555 1_555 1_555 yes
N(1) C(9) C(8) 121.10(5) 1_555 1_555 1_555 yes
C(10) C(9) C(8) 120.20(5) 1_555 1_555 1_555 yes
C(9) C(8) C(7) 121.29(5) 1_555 1_555 1_555 yes
C(9) C(8) H(8) 119.47(3) 1_555 1_555 1_555 yes
C(7) C(8) H(8) 119.23(3) 1_555 1_555 1_555 yes
N(20) C(7) C(6) 120.46(5) 1_555 1_555 1_555 yes
N(20) C(7) C(8) 122.69(5) 1_555 1_555 1_555 yes
C(6) C(7) C(8) 116.69(5) 1_555 1_555 1_555 yes
C(17) C(16) H(16A) 112.31(3) 1_555 1_555 1_555 yes
C(17) C(16) H(16B) 112.76(3) 1_555 1_555 1_555 yes
H(16A) C(16) H(16B) 105.66(6) 1_555 1_555 1_555 yes
N(20) C(25) C(24) 109.70(4) 1_555 1_555 1_555 yes
N(20) C(25) H(25A) 109.15(3) 1_555 1_555 1_555 yes
N(20) C(25) H(25B) 109.61(3) 1_555 1_555 1_555 yes
C(24) C(25) H(25A) 111.18(3) 1_555 1_555 1_555 yes
C(24) C(25) H(25B) 110.04(3) 1_555 1_555 1_555 yes
H(25A) C(25) H(25B) 107.11(6) 1_555 1_555 1_555 yes
N(20) C(21) C(22) 109.90(4) 1_555 1_555 1_555 yes
N(20) C(21) H(21A) 112.68(3) 1_555 1_555 1_555 yes
N(20) C(21) H(21B) 107.33(3) 1_555 1_555 1_555 yes
C(22) C(21) H(21A) 108.42(3) 1_555 1_555 1_555 yes
C(22) C(21) H(21B) 107.43(3) 1_555 1_555 1_555 yes
H(21A) C(21) H(21B) 110.96(6) 1_555 1_555 1_555 yes
C(25) C(24) H(24A) 110.49(3) 1_555 1_555 1_555 yes
C(25) C(24) H(24B) 109.98(3) 1_555 1_555 1_555 yes
H(24A) C(24) H(24B) 109.99(6) 1_555 1_555 1_555 yes
C(21) C(22) H(22A) 110.34(3) 1_555 1_555 1_555 yes
C(21) C(22) H(22B) 111.53(3) 1_555 1_555 1_555 yes
H(22A) C(22) H(22B) 109.44(6) 1_555 1_555 1_555 yes
C(16) C(17) H(17A) 109.44(3) 1_555 1_555 1_555 yes
C(16) C(17) H(17B) 113.25(3) 1_555 1_555 1_555 yes
C(16) C(17) H(17C) 111.20(3) 1_555 1_555 1_555 yes
H(17A) C(17) H(17B) 107.30(7) 1_555 1_555 1_555 yes
H(17A) C(17) H(17C) 106.20(7) 1_555 1_555 1_555 yes
H(17B) C(17) H(17C) 109.12(7) 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F(15) C(6) 1.3545(6) 1_555 1_555 yes
O(13) C(11) 1.2685(6) 1_555 1_555 yes
O(12) C(11) 1.2538(6) 1_555 1_555 yes
O(14) C(4) 1.2495(6) 1_555 1_555 yes
O(2) H(21) 0.9618(6) 1_555 1_555 yes
O(2) H(22) 0.9618(6) 1_555 1_555 yes
O(3) H(31) 0.9618(6) 1_555 1_555 yes
O(3) H(32) 0.9618(6) 1_555 1_555 yes
N(23) H(23A) 1.0219(6) 1_555 1_555 yes
N(23) H(23B) 1.0219(6) 1_555 1_555 yes
N(1) C(2) 1.3479(6) 1_555 1_555 yes
N(1) C(9) 1.3919(6) 1_555 1_555 yes
N(20) C(7) 1.3965(6) 1_555 1_555 yes
N(20) C(25) 1.4684(6) 1_555 1_555 yes
N(20) C(21) 1.4596(6) 1_555 1_555 yes
C(6) C(5) 1.3645(7) 1_555 1_555 yes
C(6) C(7) 1.4164(7) 1_555 1_555 yes
C(11) C(3) 1.5046(7) 1_555 1_555 yes
C(4) C(3) 1.4429(7) 1_555 1_555 yes
C(4) C(10) 1.4658(7) 1_555 1_555 yes
C(3) C(2) 1.3765(7) 1_555 1_555 yes
C(10) C(5) 1.4053(7) 1_555 1_555 yes
C(10) C(9) 1.4047(7) 1_555 1_555 yes
C(5) H(5) 1.0822(7) 1_555 1_555 yes
C(2) H(2) 1.0822(7) 1_555 1_555 yes
C(9) C(8) 1.4093(7) 1_555 1_555 yes
C(8) C(7) 1.4004(7) 1_555 1_555 yes
C(8) H(8) 1.0823(7) 1_555 1_555 yes
C(16) C(17) 1.5212(7) 1_555 1_555 yes
C(16) H(16A) 1.0877(7) 1_555 1_555 yes
C(16) H(16B) 1.0877(7) 1_555 1_555 yes
C(25) C(24) 1.5205(7) 1_555 1_555 yes
C(25) H(25A) 1.0993(7) 1_555 1_555 yes
C(25) H(25B) 1.0993(7) 1_555 1_555 yes
C(21) C(22) 1.5177(7) 1_555 1_555 yes
C(21) H(21A) 1.0993(7) 1_555 1_555 yes
C(21) H(21B) 1.0993(7) 1_555 1_555 yes
C(24) H(24A) 1.0993(7) 1_555 1_555 yes
C(24) H(24B) 1.0993(7) 1_555 1_555 yes
C(22) H(22A) 1.0993(7) 1_555 1_555 yes
C(22) H(22B) 1.0993(7) 1_555 1_555 yes
C(17) H(17A) 1.0913(7) 1_555 1_555 yes
C(17) H(17B) 1.0914(7) 1_555 1_555 yes
C(17) H(17C) 1.0913(7) 1_555 1_555 yes
