#------------------------------------------------------------------------------
#$Date: 2020-07-04 08:16:55 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253759 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243470.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243470
loop_
_publ_author_name
'Harish Chinthal, Chayanna'
'Yathirajan, Hemmige S.'
'Kavitha, Channappa N.'
'Foro, Sabine'
'Glidewell, Christopher'
_publ_section_title
;
 The crystal structures of salts of N-(4-fluorophenyl)piperazine
 with four aromatic carboxylic acids and with picric acid
;
_journal_coeditor_code           HB7928
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1179
_journal_page_last               1186
_journal_paper_doi               10.1107/S2056989020008749
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C10 H14 F N2 +, C7 H4 I O2 -'
_chemical_formula_moiety         'C10 H14 F N2 +, C7 H4 I O2 -'
_chemical_formula_sum            'C17 H18 F I N2 O2'
_chemical_formula_weight         428.23
_chemical_name_systematic
;
4-(4-Fluorophenyl)piperazin-1-ium 2-iodobenzoate
;
_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
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                106.776(5)
_cell_angle_beta                 93.327(4)
_cell_angle_gamma                104.874(4)
_cell_formula_units_Z            4
_cell_length_a                   9.8892(3)
_cell_length_b                   11.6831(7)
_cell_length_c                   16.4547(9)
_cell_measurement_reflns_used    7405
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.823
_cell_measurement_theta_min      2.612
_cell_volume                     1741.19(17)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur with Sapphire CCD
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.612
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.859
_exptl_absorpt_correction_T_max  0.411
_exptl_absorpt_correction_T_min  0.383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.480
_refine_diff_density_max         2.920
_refine_diff_density_min         -2.003
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         7396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0543P)²+4.1226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                5890
_reflns_number_total             7396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7928sup1.cif
_cod_data_source_block           III
_cod_original_cell_volume        1741.19(16)
_cod_database_code               2243470
_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   0.457
_shelx_estimated_absorpt_t_max   0.469
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N11 0.1718(4) 0.3441(4) 0.4399(3) 0.0473(9) Uani d 1 . .
H H111 0.168(6) 0.371(5) 0.490(4) 0.057 Uiso d 1 . .
H H112 0.156(6) 0.261(5) 0.425(3) 0.057 Uiso d 1 . .
C C12 0.3127(5) 0.4007(5) 0.4209(3) 0.0592(12) Uani d 1 . .
H H12A 0.3831 0.3744 0.4486 0.071 Uiso calc 1 . .
H H12B 0.3356 0.4909 0.4437 0.071 Uiso calc 1 . .
C C13 0.3165(5) 0.3626(5) 0.3258(3) 0.0546(12) Uani d 1 . .
H H13A 0.4093 0.4023 0.3146 0.066 Uiso calc 1 . .
H H13B 0.3000 0.2730 0.3037 0.066 Uiso calc 1 . .
N N14 0.2090(4) 0.3984(3) 0.2818(3) 0.0450(8) Uani d 1 . .
C C15 0.0698(5) 0.3408(5) 0.2987(4) 0.0579(12) Uani d 1 . .
H H15A 0.0483 0.2508 0.2752 0.069 Uiso calc 1 . .
H H15B -0.0002 0.3668 0.2704 0.069 Uiso calc 1 . .
C C16 0.0617(5) 0.3762(5) 0.3932(4) 0.0598(13) Uani d 1 . .
H H16A 0.0736 0.4652 0.4155 0.072 Uiso calc 1 . .
H H16B -0.0309 0.3330 0.4025 0.072 Uiso calc 1 . .
C C121 0.2253(5) 0.3925(4) 0.1963(3) 0.0487(10) Uani d 1 . .
C C122 0.3559(6) 0.4465(5) 0.1766(4) 0.0597(12) Uani d 1 . .
H H122 0.4329 0.4829 0.2199 0.072 Uiso calc 1 . .
C C123 0.3747(7) 0.4476(6) 0.0947(4) 0.0741(16) Uani d 1 . .
H H123 0.4631 0.4837 0.0823 0.089 Uiso calc 1 . .
C C124 0.2606(9) 0.3945(6) 0.0319(4) 0.0760(18) Uani d 1 . .
F F124 0.2786(6) 0.3960(4) -0.0494(2) 0.1097(15) Uani d 1 . .
C C125 0.1323(8) 0.3422(6) 0.0477(4) 0.0817(19) Uani d 1 . .
H H125 0.0563 0.3083 0.0037 0.098 Uiso calc 1 . .
C C126 0.1126(6) 0.3385(5) 0.1294(4) 0.0680(15) Uani d 1 . .
H H126 0.0238 0.2999 0.1400 0.082 Uiso calc 1 . .
N N21 0.3249(4) 0.1830(4) 0.5932(3) 0.0481(9) Uani d 1 . .
H H211 0.329(6) 0.157(5) 0.544(4) 0.058 Uiso d 1 . .
H H212 0.337(6) 0.261(6) 0.611(4) 0.058 Uiso d 1 . .
C C22 0.4376(5) 0.1501(6) 0.6362(3) 0.0589(13) Uani d 1 . .
H H22A 0.5290 0.1980 0.6284 0.071 Uiso calc 1 . .
H H22B 0.4291 0.0623 0.6100 0.071 Uiso calc 1 . .
C C23 0.4291(5) 0.1759(5) 0.7303(3) 0.0550(12) Uani d 1 . .
H H23A 0.5000 0.1479 0.7561 0.066 Uiso calc 1 . .
H H23B 0.4487 0.2651 0.7578 0.066 Uiso calc 1 . .
N N24 0.2907(4) 0.1127(3) 0.7441(2) 0.0445(8) Uani d 1 . .
C C25 0.1819(5) 0.1523(5) 0.7055(3) 0.0537(11) Uani d 1 . .
H H25A 0.1977 0.2412 0.7318 0.064 Uiso calc 1 . .
H H25B 0.0899 0.1096 0.7160 0.064 Uiso calc 1 . .
C C26 0.1841(5) 0.1235(5) 0.6102(3) 0.0604(13) Uani d 1 . .
H H26A 0.1602 0.0340 0.5832 0.072 Uiso calc 1 . .
H H26B 0.1141 0.1539 0.5859 0.072 Uiso calc 1 . .
C C221 0.2749(5) 0.0994(4) 0.8257(3) 0.0462(10) Uani d 1 . .
C C222 0.3844(6) 0.1474(5) 0.8936(3) 0.0604(13) Uani d 1 . .
H H222 0.4722 0.1944 0.8871 0.072 Uiso calc 1 . .
C C223 0.3638(7) 0.1256(6) 0.9712(4) 0.0739(16) Uani d 1 . .
H H223 0.4373 0.1580 1.0167 0.089 Uiso calc 1 . .
C C224 0.2374(8) 0.0578(6) 0.9801(4) 0.0749(17) Uani d 1 . .
F F224 0.2184(6) 0.0351(5) 1.0561(3) 0.1125(15) Uani d 1 . .
C C225 0.1270(7) 0.0094(6) 0.9158(4) 0.0711(15) Uani d 1 . .
H H225 0.0400 -0.0366 0.9240 0.085 Uiso calc 1 . .
C C226 0.1453(5) 0.0295(5) 0.8381(4) 0.0573(12) Uani d 1 . .
H H226 0.0703 -0.0041 0.7935 0.069 Uiso calc 1 . .
C C131 0.2741(4) 0.5826(4) 0.7440(3) 0.0436(9) Uani d 1 . .
C C132 0.3185(4) 0.7104(4) 0.7577(3) 0.0438(9) Uani d 1 . .
I I132 0.38641(4) 0.78363(3) 0.65990(2) 0.06260(12) Uani d 1 . .
C C133 0.3235(6) 0.7943(5) 0.8376(3) 0.0579(12) Uani d 1 . .
H H133 0.3542 0.8796 0.8461 0.069 Uiso calc 1 . .
C C134 0.2831(7) 0.7512(6) 0.9039(4) 0.0714(16) Uani d 1 . .
H H134 0.2850 0.8074 0.9574 0.086 Uiso calc 1 . .
C C135 0.2401(7) 0.6259(6) 0.8920(4) 0.0755(17) Uani d 1 . .
H H135 0.2128 0.5971 0.9374 0.091 Uiso calc 1 . .
C C136 0.2371(6) 0.5442(5) 0.8148(4) 0.0621(13) Uani d 1 . .
H H136 0.2097 0.4594 0.8083 0.075 Uiso calc 1 . .
C C137 0.2666(5) 0.4864(4) 0.6585(3) 0.0456(10) Uani d 1 . .
O O131 0.3594(4) 0.4325(3) 0.6506(3) 0.0648(10) Uani d 1 . .
O O132 0.1659(5) 0.4666(4) 0.6041(3) 0.0837(13) Uani d 1 . .
C C231 0.2056(4) -0.0826(4) 0.3071(3) 0.0408(9) Uani d 1 . .
C C232 0.1850(4) -0.1973(4) 0.3215(3) 0.0454(10) Uani d 1 . .
I I232 0.18832(4) -0.21282(3) 0.44547(2) 0.06302(13) Uani d 1 . .
C C233 0.1639(6) -0.3058(5) 0.2536(4) 0.0684(15) Uani d 1 . .
H H233 0.1502 -0.3819 0.2640 0.082 Uiso calc 1 . .
C C234 0.1632(8) -0.3016(6) 0.1721(4) 0.0837(19) Uani d 1 . .
H H234 0.1488 -0.3748 0.1267 0.100 Uiso calc 1 . .
C C235 0.1838(7) -0.1889(6) 0.1561(4) 0.0732(16) Uani d 1 . .
H H235 0.1839 -0.1862 0.1002 0.088 Uiso calc 1 . .
C C236 0.2044(5) -0.0805(5) 0.2232(3) 0.0541(11) Uani d 1 . .
H H236 0.2175 -0.0050 0.2121 0.065 Uiso calc 1 . .
C C237 0.2275(5) 0.0386(4) 0.3779(3) 0.0434(9) Uani d 1 . .
O O231 0.1327(4) 0.0902(3) 0.3784(3) 0.0689(10) Uani d 1 . .
O O232 0.3391(4) 0.0769(3) 0.4284(2) 0.0619(9) Uani d 1 . .
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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 N11 C16 . . 110.2(4) ?
C12 N11 H111 . . 110(4) ?
C16 N11 H111 . . 108(4) ?
C12 N11 H112 . . 109(3) ?
C16 N11 H112 . . 111(3) ?
H111 N11 H112 . . 109(5) ?
N11 C12 C13 . . 110.8(4) ?
N11 C12 H12A . . 109.5 ?
C13 C12 H12A . . 109.5 ?
N11 C12 H12B . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
N14 C13 C12 . . 110.8(4) ?
N14 C13 H13A . . 109.5 ?
C12 C13 H13A . . 109.5 ?
N14 C13 H13B . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.1 ?
C121 N14 C15 . . 117.6(4) ?
C121 N14 C13 . . 114.6(4) ?
C15 N14 C13 . . 110.1(4) ?
N14 C15 C16 . . 111.3(4) ?
N14 C15 H15A . . 109.4 ?
C16 C15 H15A . . 109.4 ?
N14 C15 H15B . . 109.4 ?
C16 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
N11 C16 C15 . . 111.3(4) ?
N11 C16 H16A . . 109.4 ?
C15 C16 H16A . . 109.4 ?
N11 C16 H16B . . 109.4 ?
C15 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
C122 C121 C126 . . 117.4(5) ?
C122 C121 N14 . . 120.0(4) ?
C126 C121 N14 . . 122.6(5) ?
C123 C122 C121 . . 121.7(5) ?
C123 C122 H122 . . 119.1 ?
C121 C122 H122 . . 119.1 ?
C124 C123 C122 . . 118.5(6) ?
C124 C123 H123 . . 120.8 ?
C122 C123 H123 . . 120.8 ?
C125 C124 C123 . . 122.1(6) ?
C125 C124 F124 . . 119.2(7) ?
C123 C124 F124 . . 118.7(7) ?
C124 C125 C126 . . 120.0(6) ?
C124 C125 H125 . . 120.0 ?
C126 C125 H125 . . 120.0 ?
C125 C126 C121 . . 120.3(6) ?
C125 C126 H126 . . 119.9 ?
C121 C126 H126 . . 119.9 ?
C26 N21 C22 . . 112.1(4) ?
C26 N21 H211 . . 109(4) ?
C22 N21 H211 . . 105(4) ?
C26 N21 H212 . . 107(4) ?
C22 N21 H212 . . 110(4) ?
H211 N21 H212 . . 114(6) ?
N21 C22 C23 . . 111.3(4) ?
N21 C22 H22A . . 109.4 ?
C23 C22 H22A . . 109.4 ?
N21 C22 H22B . . 109.4 ?
C23 C22 H22B . . 109.4 ?
H22A C22 H22B . . 108.0 ?
N24 C23 C22 . . 110.7(4) ?
N24 C23 H23A . . 109.5 ?
C22 C23 H23A . . 109.5 ?
N24 C23 H23B . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 108.1 ?
C221 N24 C23 . . 118.0(4) ?
C221 N24 C25 . . 116.3(4) ?
C23 N24 C25 . . 110.7(4) ?
N24 C25 C26 . . 110.6(4) ?
N24 C25 H25A . . 109.5 ?
C26 C25 H25A . . 109.5 ?
N24 C25 H25B . . 109.5 ?
C26 C25 H25B . . 109.5 ?
H25A C25 H25B . . 108.1 ?
N21 C26 C25 . . 110.2(4) ?
N21 C26 H26A . . 109.6 ?
C25 C26 H26A . . 109.6 ?
N21 C26 H26B . . 109.6 ?
C25 C26 H26B . . 109.6 ?
H26A C26 H26B . . 108.1 ?
C222 C221 C226 . . 117.9(5) ?
C222 C221 N24 . . 123.2(4) ?
C226 C221 N24 . . 118.8(4) ?
C221 C222 C223 . . 120.3(5) ?
C221 C222 H222 . . 119.8 ?
C223 C222 H222 . . 119.8 ?
C224 C223 C222 . . 119.6(6) ?
C224 C223 H223 . . 120.2 ?
C222 C223 H223 . . 120.2 ?
C223 C224 C225 . . 122.3(6) ?
C223 C224 F224 . . 119.3(6) ?
C225 C224 F224 . . 118.4(6) ?
C224 C225 C226 . . 119.1(6) ?
C224 C225 H225 . . 120.5 ?
C226 C225 H225 . . 120.5 ?
C225 C226 C221 . . 120.8(5) ?
C225 C226 H226 . . 119.6 ?
C221 C226 H226 . . 119.6 ?
C132 C131 C136 . . 116.7(4) ?
C132 C131 C137 . . 123.5(4) ?
C136 C131 C137 . . 119.8(4) ?
C133 C132 C131 . . 120.9(4) ?
C133 C132 I132 . . 117.5(4) ?
C131 C132 I132 . . 121.6(3) ?
C134 C133 C132 . . 119.7(5) ?
C134 C133 H133 . . 120.1 ?
C132 C133 H133 . . 120.1 ?
C135 C134 C133 . . 120.3(5) ?
C135 C134 H134 . . 119.8 ?
C133 C134 H134 . . 119.8 ?
C136 C135 C134 . . 120.1(6) ?
C136 C135 H135 . . 120.0 ?
C134 C135 H135 . . 120.0 ?
C135 C136 C131 . . 122.2(5) ?
C135 C136 H136 . . 118.9 ?
C131 C136 H136 . . 118.9 ?
O132 C137 O131 . . 126.0(5) ?
O132 C137 C131 . . 116.7(4) ?
O131 C137 C131 . . 117.3(4) ?
C236 C231 C232 . . 118.2(4) ?
C236 C231 C237 . . 118.5(4) ?
C232 C231 C237 . . 123.3(4) ?
C233 C232 C231 . . 120.7(5) ?
C233 C232 I232 . . 117.4(4) ?
C231 C232 I232 . . 121.9(3) ?
C234 C233 C232 . . 120.2(5) ?
C234 C233 H233 . . 119.9 ?
C232 C233 H233 . . 119.9 ?
C233 C234 C235 . . 120.3(5) ?
C233 C234 H234 . . 119.9 ?
C235 C234 H234 . . 119.9 ?
C236 C235 C234 . . 119.9(5) ?
C236 C235 H235 . . 120.0 ?
C234 C235 H235 . . 120.0 ?
C235 C236 C231 . . 120.8(5) ?
C235 C236 H236 . . 119.6 ?
C231 C236 H236 . . 119.6 ?
O231 C237 O232 . . 127.0(4) ?
O231 C237 C231 . . 116.2(4) ?
O232 C237 C231 . . 116.7(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N11 C12 . 1.474(6) ?
N11 C16 . 1.483(6) ?
N11 H111 . 0.80(6) ?
N11 H112 . 0.89(6) ?
C12 C13 . 1.505(7) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 N14 . 1.463(5) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
N14 C121 . 1.410(6) ?
N14 C15 . 1.450(6) ?
C15 C16 . 1.501(8) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C121 C122 . 1.385(7) ?
C121 C126 . 1.395(7) ?
C122 C123 . 1.374(8) ?
C122 H122 . 0.9300 ?
C123 C124 . 1.364(10) ?
C123 H123 . 0.9300 ?
C124 C125 . 1.335(10) ?
C124 F124 . 1.364(7) ?
C125 C126 . 1.381(9) ?
C125 H125 . 0.9300 ?
C126 H126 . 0.9300 ?
N21 C26 . 1.470(7) ?
N21 C22 . 1.475(6) ?
N21 H211 . 0.78(6) ?
N21 H212 . 0.84(6) ?
C22 C23 . 1.502(7) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 N24 . 1.444(6) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
N24 C221 . 1.408(6) ?
N24 C25 . 1.456(6) ?
C25 C26 . 1.509(7) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
C221 C222 . 1.387(7) ?
C221 C226 . 1.394(7) ?
C222 C223 . 1.389(8) ?
C222 H222 . 0.9300 ?
C223 C224 . 1.338(9) ?
C223 H223 . 0.9300 ?
C224 C225 . 1.354(9) ?
C224 F224 . 1.366(7) ?
C225 C226 . 1.378(8) ?
C225 H225 . 0.9300 ?
C226 H226 . 0.9300 ?
C131 C132 . 1.389(6) ?
C131 C136 . 1.400(7) ?
C131 C137 . 1.510(6) ?
C132 C133 . 1.383(7) ?
C132 I132 . 2.097(5) ?
C133 C134 . 1.367(8) ?
C133 H133 . 0.9300 ?
C134 C135 . 1.366(9) ?
C134 H134 . 0.9300 ?
C135 C136 . 1.344(8) ?
C135 H135 . 0.9300 ?
C136 H136 . 0.9300 ?
C137 O132 . 1.228(6) ?
C137 O131 . 1.232(5) ?
C231 C236 . 1.388(7) ?
C231 C232 . 1.393(6) ?
C231 C237 . 1.507(6) ?
C232 C233 . 1.385(7) ?
C232 I232 . 2.099(5) ?
C233 C234 . 1.357(9) ?
C233 H233 . 0.9300 ?
C234 C235 . 1.383(9) ?
C234 H234 . 0.9300 ?
C235 C236 . 1.377(7) ?
C235 H235 . 0.9300 ?
C236 H236 . 0.9300 ?
C237 O231 . 1.237(6) ?
C237 O232 . 1.238(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N11 H111 O132 . 0.80(6) 1.89(6) 2.680(7) 168(6) no
N11 H112 O231 . 0.90(6) 1.87(6) 2.758(6) 171(4) no
N21 H211 O232 . 0.79(6) 1.88(6) 2.665(6) 173(6) no
N21 H212 O131 . 0.85(7) 1.87(7) 2.714(6) 179(8) no
C13 H13A O131 2_666 0.97 2.50 3.396(7) 154 no
C133 H133 Cg2 1_565 0.93 2.69 3.433(6) 137 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 N11 C12 C13 . . . . -55.3(6) ?
N11 C12 C13 N14 . . . . 57.8(6) ?
C12 C13 N14 C121 . . . . 166.2(4) ?
C12 C13 N14 C15 . . . . -58.5(5) ?
C121 N14 C15 C16 . . . . -168.6(4) ?
C13 N14 C15 C16 . . . . 57.6(5) ?
C12 N11 C16 C15 . . . . 54.5(6) ?
N14 C15 C16 N11 . . . . -56.1(6) ?
C15 N14 C121 C122 . . . . 179.7(4) ?
C13 N14 C121 C122 . . . . -48.5(6) ?
C15 N14 C121 C126 . . . . 2.6(6) ?
C13 N14 C121 C126 . . . . 134.4(5) ?
C126 C121 C122 C123 . . . . 0.2(8) ?
N14 C121 C122 C123 . . . . -177.1(5) ?
C121 C122 C123 C124 . . . . 0.4(9) ?
C122 C123 C124 C125 . . . . 0.2(10) ?
C122 C123 C124 F124 . . . . 179.6(5) ?
C123 C124 C125 C126 . . . . -1.3(10) ?
F124 C124 C125 C126 . . . . 179.2(5) ?
C124 C125 C126 C121 . . . . 1.9(10) ?
C122 C121 C126 C125 . . . . -1.3(8) ?
N14 C121 C126 C125 . . . . 175.9(5) ?
C26 N21 C22 C23 . . . . -53.0(6) ?
N21 C22 C23 N24 . . . . 55.1(6) ?
C22 C23 N24 C221 . . . . 163.7(4) ?
C22 C23 N24 C25 . . . . -58.7(5) ?
C221 N24 C25 C26 . . . . -161.9(4) ?
C23 N24 C25 C26 . . . . 59.8(5) ?
C22 N21 C26 C25 . . . . 53.6(6) ?
N24 C25 C26 N21 . . . . -56.6(6) ?
C23 N24 C221 C222 . . . . 2.1(7) ?
C25 N24 C221 C222 . . . . -133.2(5) ?
C23 N24 C221 C226 . . . . -174.5(4) ?
C25 N24 C221 C226 . . . . 50.2(6) ?
C226 C221 C222 C223 . . . . -0.1(8) ?
N24 C221 C222 C223 . . . . -176.7(5) ?
C221 C222 C223 C224 . . . . 0.1(9) ?
C222 C223 C224 C225 . . . . -0.4(10) ?
C222 C223 C224 F224 . . . . 179.0(5) ?
C223 C224 C225 C226 . . . . 0.7(10) ?
F224 C224 C225 C226 . . . . -178.7(5) ?
C224 C225 C226 C221 . . . . -0.6(8) ?
C222 C221 C226 C225 . . . . 0.3(7) ?
N24 C221 C226 C225 . . . . 177.1(5) ?
C136 C131 C132 C133 . . . . -0.9(6) ?
C137 C131 C132 C133 . . . . -179.8(4) ?
C136 C131 C132 I132 . . . . 177.2(3) ?
C137 C131 C132 I132 . . . . -1.8(6) ?
C131 C132 C133 C134 . . . . -0.5(7) ?
I132 C132 C133 C134 . . . . -178.6(4) ?
C132 C133 C134 C135 . . . . 1.0(9) ?
C133 C134 C135 C136 . . . . 0.0(10) ?
C134 C135 C136 C131 . . . . -1.5(10) ?
C132 C131 C136 C135 . . . . 1.9(8) ?
C137 C131 C136 C135 . . . . -179.1(5) ?
C132 C131 C137 O132 . . . . -77.1(6) ?
C136 C131 C137 O132 . . . . 103.9(6) ?
C132 C131 C137 O131 . . . . 104.8(5) ?
C136 C131 C137 O131 . . . . -74.1(6) ?
C236 C231 C232 C233 . . . . 0.0(7) ?
C237 C231 C232 C233 . . . . 179.3(5) ?
C236 C231 C232 I232 . . . . 178.8(3) ?
C237 C231 C232 I232 . . . . -1.8(6) ?
C231 C232 C233 C234 . . . . 0.1(8) ?
I232 C232 C233 C234 . . . . -178.8(5) ?
C232 C233 C234 C235 . . . . 0.1(10) ?
C233 C234 C235 C236 . . . . -0.4(10) ?
C234 C235 C236 C231 . . . . 0.4(9) ?
C232 C231 C236 C235 . . . . -0.2(7) ?
C237 C231 C236 C235 . . . . -179.6(5) ?
C236 C231 C237 O231 . . . . 66.0(6) ?
C232 C231 C237 O231 . . . . -113.4(5) ?
C236 C231 C237 O232 . . . . -112.9(5) ?
C232 C231 C237 O232 . . . . 67.8(6) ?

_cod_database_fobs_code 2243470
