#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/76/2017694.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_2017694
loop_
_publ_author_name
'Heilmann-Brohl, Julia'
'Wagner, Matthias'
'Lerner, Hans-Wolfram'
'Bolte, Michael'
_publ_section_title
;
 Structural comparison of three
 N-(4-halogenophenyl)-N'-[1-(2-pyridyl)ethylidene]hydrazine
 hydrochlorides
;
_journal_coeditor_code           DN3144
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o364
_journal_page_last               o368
_journal_paper_doi               10.1107/S0108270110019827
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H13 F N3 + , Cl - , 2C H4 O'
_chemical_formula_moiety         'C13 H13 F N3 + , Cl - , 2C H4 O'
_chemical_formula_sum            'C15 H21 Cl F N3 O2'
_chemical_formula_weight         329.80
_chemical_name_systematic
;
2-{1-[(4-Fluoroanilino)methylidene]ethyl}pyridinium chloride methanol
disolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                96.321(9)
_cell_angle_beta                 92.066(9)
_cell_angle_gamma                107.247(9)
_cell_formula_units_Z            4
_cell_length_a                   7.0088(8)
_cell_length_b                   11.7258(14)
_cell_length_c                   21.843(2)
_cell_measurement_reflns_used    12810
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.24
_cell_volume                     1699.5(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21250
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.19
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.9666
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         7158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0298
_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)+(0.0200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0584
_reflns_number_gt                4239
_reflns_number_total             7158
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3144.cif
_cod_data_source_block           III
_cod_original_cell_volume        1699.6(3)
_cod_database_code               2017694
_cod_database_fobs_code          2017694
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.06824(7) 0.39520(4) 0.835725(17) 0.04234(11) Uani d . 1 . .
Cl Cl2 0.70783(7) 0.36712(4) 0.328298(17) 0.04196(11) Uani d . 1 . .
N N1 0.7276(2) 0.48488(11) 0.94796(6) 0.0351(3) Uani d . 1 . .
H H1 0.683(3) 0.4436(15) 0.9145(8) 0.040(5) Uiso d . 1 . .
N N2 0.69117(19) 0.43426(11) 0.99985(5) 0.0315(3) Uani d . 1 . .
C C2 0.5986(2) 0.31994(13) 0.99561(6) 0.0326(3) Uani d . 1 . .
C C3 0.5307(3) 0.23792(14) 0.93617(7) 0.0449(4) Uani d . 1 . .
H H3A 0.6418 0.2494 0.9092 0.067 Uiso calc R 1 . .
H H3B 0.4189 0.2566 0.9157 0.067 Uiso calc R 1 . .
H H3C 0.4870 0.1541 0.9448 0.067 Uiso calc R 1 . .
C C11 0.8345(2) 0.60680(13) 0.95032(7) 0.0318(3) Uani d . 1 . .
C C12 0.9020(2) 0.68115(13) 1.00578(7) 0.0357(4) Uani d . 1 . .
H H12 0.8760 0.6496 1.0439 0.043 Uiso calc R 1 . .
C C13 1.0078(2) 0.80191(14) 1.00527(7) 0.0385(4) Uani d . 1 . .
H H13 1.0542 0.8538 1.0428 0.046 Uiso calc R 1 . .
C C14 1.0437(2) 0.84435(13) 0.94967(7) 0.0371(4) Uani d . 1 . .
F F14 1.14943(15) 0.96342(8) 0.94906(4) 0.0510(3) Uani d . 1 . .
C C15 0.9790(2) 0.77361(13) 0.89407(7) 0.0372(4) Uani d . 1 . .
H H15 1.0061 0.8063 0.8563 0.045 Uiso calc R 1 . .
C C16 0.8734(2) 0.65336(14) 0.89447(7) 0.0358(4) Uani d . 1 . .
H H16 0.8273 0.6025 0.8566 0.043 Uiso calc R 1 . .
C C21 0.5654(2) 0.27333(13) 1.05501(6) 0.0322(3) Uani d . 1 . .
N N22 0.6445(2) 0.34944(12) 1.10693(6) 0.0331(3) Uani d . 1 . .
H H22 0.722(2) 0.4254(15) 1.1036(7) 0.036(4) Uiso d . 1 . .
C C23 0.6243(3) 0.31773(14) 1.16431(7) 0.0389(4) Uani d . 1 . .
H H23 0.6825 0.3753 1.1992 0.047 Uiso calc R 1 . .
C C24 0.5195(3) 0.20214(15) 1.17223(7) 0.0416(4) Uani d . 1 . .
H H24 0.5048 0.1784 1.2124 0.050 Uiso calc R 1 . .
C C25 0.4355(3) 0.12077(14) 1.12061(7) 0.0421(4) Uani d . 1 . .
H H25 0.3617 0.0404 1.1253 0.051 Uiso calc R 1 . .
C C26 0.4581(2) 0.15534(14) 1.06253(7) 0.0376(4) Uani d . 1 . .
H H26 0.4003 0.0987 1.0273 0.045 Uiso calc R 1 . .
N N1A 0.2446(2) 0.48192(11) 0.45536(6) 0.0343(3) Uani d . 1 . .
H H1A 0.226(2) 0.4372(14) 0.4218(8) 0.038(5) Uiso d . 1 . .
N N2A 0.18085(19) 0.43786(11) 0.50735(5) 0.0325(3) Uani d . 1 . .
C C2A 0.0736(2) 0.32604(13) 0.50393(7) 0.0330(3) Uani d . 1 . .
C C3A 0.0126(3) 0.24187(14) 0.44479(7) 0.0406(4) Uani d . 1 . .
H H3A1 -0.0501 0.2788 0.4149 0.061 Uiso calc R 1 . .
H H3A2 -0.0831 0.1661 0.4529 0.061 Uiso calc R 1 . .
H H3A3 0.1311 0.2258 0.4280 0.061 Uiso calc R 1 . .
C C11A 0.3642(2) 0.60216(13) 0.45792(7) 0.0319(3) Uani d . 1 . .
C C12A 0.4080(2) 0.68097(13) 0.51257(7) 0.0348(4) Uani d . 1 . .
H H12A 0.3597 0.6536 0.5501 0.042 Uiso calc R 1 . .
C C13A 0.5222(3) 0.79955(14) 0.51206(7) 0.0395(4) Uani d . 1 . .
H H13A 0.5529 0.8543 0.5490 0.047 Uiso calc R 1 . .
C C14A 0.5899(3) 0.83650(13) 0.45735(7) 0.0396(4) Uani d . 1 . .
F F14A 0.70313(17) 0.95385(8) 0.45658(4) 0.0582(3) Uani d . 1 . .
C C15A 0.5499(2) 0.76067(14) 0.40260(7) 0.0381(4) Uani d . 1 . .
H H15A 0.5998 0.7890 0.3654 0.046 Uiso calc R 1 . .
C C16A 0.4356(2) 0.64250(13) 0.40288(7) 0.0351(4) Uani d . 1 . .
H H16A 0.4055 0.5886 0.3656 0.042 Uiso calc R 1 . .
C C21A 0.0143(2) 0.28592(13) 0.56329(6) 0.0322(3) Uani d . 1 . .
N N22A 0.0658(2) 0.36833(12) 0.61436(6) 0.0333(3) Uani d . 1 . .
H H22A 0.135(3) 0.4436(16) 0.6114(8) 0.043(5) Uiso d . 1 . .
C C23A 0.0209(2) 0.34280(14) 0.67159(7) 0.0382(4) Uani d . 1 . .
H H23A 0.0601 0.4047 0.7056 0.046 Uiso calc R 1 . .
C C24A -0.0813(3) 0.22747(15) 0.68089(7) 0.0434(4) Uani d . 1 . .
H H24A -0.1134 0.2083 0.7212 0.052 Uiso calc R 1 . .
C C25A -0.1369(3) 0.13953(15) 0.63032(7) 0.0439(4) Uani d . 1 . .
H H25A -0.2075 0.0590 0.6358 0.053 Uiso calc R 1 . .
C C26A -0.0901(3) 0.16818(14) 0.57208(7) 0.0387(4) Uani d . 1 . .
H H26A -0.1293 0.1073 0.5376 0.046 Uiso calc R 1 . .
O O1M 0.5121(2) 0.40944(12) 0.82663(5) 0.0540(3) Uani d . 1 . .
H H1M 0.377(4) 0.393(2) 0.8300(11) 0.089(8) Uiso d . 1 . .
C C1M 0.5448(4) 0.3692(3) 0.76751(9) 0.0896(8) Uani d . 1 . .
H H1M1 0.4621 0.3944 0.7379 0.134 Uiso calc R 1 . .
H H1M2 0.5090 0.2811 0.7623 0.134 Uiso calc R 1 . .
H H1M3 0.6865 0.4032 0.7603 0.134 Uiso calc R 1 . .
O O2M -0.1240(3) 0.11921(14) 0.83089(7) 0.0780(5) Uani d . 1 . .
H H2M -0.070(4) 0.200(3) 0.8328(12) 0.108(9) Uiso d . 1 . .
C C2M 0.0255(4) 0.0708(2) 0.80911(11) 0.0791(7) Uani d . 1 . .
H H2M1 0.1195 0.1295 0.7873 0.119 Uiso calc R 1 . .
H H2M2 -0.0364 -0.0030 0.7808 0.119 Uiso calc R 1 . .
H H2M3 0.0976 0.0522 0.8441 0.119 Uiso calc R 1 . .
O O3M 0.2720(2) 0.36917(12) 0.33337(5) 0.0551(3) Uani d . 1 . .
H H3M 0.396(4) 0.3716(19) 0.3358(10) 0.074(7) Uiso d . 1 . .
C C3M 0.1617(3) 0.2922(2) 0.28236(10) 0.0819(8) Uani d . 1 . .
H H3MB 0.0226 0.2936 0.2818 0.123 Uiso calc R 1 . .
H H3MC 0.1654 0.2100 0.2852 0.123 Uiso calc R 1 . .
H H3MD 0.2200 0.3189 0.2443 0.123 Uiso calc R 1 . .
O O4M 0.4818(3) 0.09243(15) 0.32573(8) 0.0804(5) Uani d . 1 . .
H H4M 0.533(4) 0.168(2) 0.3318(11) 0.092(8) Uiso d . 1 . .
C C4M 0.6154(4) 0.0320(2) 0.30259(11) 0.0806(7) Uani d . 1 . .
H H4M1 0.6922 0.0761 0.2714 0.121 Uiso calc R 1 . .
H H4M2 0.5397 -0.0495 0.2838 0.121 Uiso calc R 1 . .
H H4M3 0.7074 0.0274 0.3365 0.121 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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'
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
N2 N1 C11 . . 120.48(12) ?
N2 N1 H1 . . 119.0(12) ?
C11 N1 H1 . . 120.5(12) ?
C2 N2 N1 . . 118.58(12) ?
N2 C2 C21 . . 114.35(13) ?
N2 C2 C3 . . 124.89(14) ?
C21 C2 C3 . . 120.75(14) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C12 C11 C16 . . 119.93(15) ?
C12 C11 N1 . . 122.36(14) ?
C16 C11 N1 . . 117.71(13) ?
C11 C12 C13 . . 119.80(15) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C14 C13 C12 . . 118.67(14) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
C13 C14 C15 . . 123.09(15) ?
C13 C14 F14 . . 118.76(13) ?
C15 C14 F14 . . 118.15(14) ?
C14 C15 C16 . . 118.34(15) ?
C14 C15 H15 . . 120.8 ?
C16 C15 H15 . . 120.8 ?
C15 C16 C11 . . 120.17(14) ?
C15 C16 H16 . . 119.9 ?
C11 C16 H16 . . 119.9 ?
N22 C21 C26 . . 116.93(14) ?
N22 C21 C2 . . 118.06(14) ?
C26 C21 C2 . . 125.01(13) ?
C23 N22 C21 . . 123.83(15) ?
C23 N22 H22 . . 116.9(10) ?
C21 N22 H22 . . 119.1(10) ?
N22 C23 C24 . . 119.74(15) ?
N22 C23 H23 . . 120.1 ?
C24 C23 H23 . . 120.1 ?
C23 C24 C25 . . 118.71(15) ?
C23 C24 H24 . . 120.6 ?
C25 C24 H24 . . 120.6 ?
C26 C25 C24 . . 120.45(16) ?
C26 C25 H25 . . 119.8 ?
C24 C25 H25 . . 119.8 ?
C25 C26 C21 . . 120.34(14) ?
C25 C26 H26 . . 119.8 ?
C21 C26 H26 . . 119.8 ?
N2A N1A C11A . . 119.75(13) ?
N2A N1A H1A . . 121.1(12) ?
C11A N1A H1A . . 118.8(12) ?
C2A N2A N1A . . 118.60(13) ?
N2A C2A C21A . . 114.45(13) ?
N2A C2A C3A . . 124.25(14) ?
C21A C2A C3A . . 121.30(14) ?
C2A C3A H3A1 . . 109.5 ?
C2A C3A H3A2 . . 109.5 ?
H3A1 C3A H3A2 . . 109.5 ?
C2A C3A H3A3 . . 109.5 ?
H3A1 C3A H3A3 . . 109.5 ?
H3A2 C3A H3A3 . . 109.5 ?
C12A C11A C16A . . 120.06(14) ?
C12A C11A N1A . . 122.20(15) ?
C16A C11A N1A . . 117.72(13) ?
C13A C12A C11A . . 119.73(15) ?
C13A C12A H12A . . 120.1 ?
C11A C12A H12A . . 120.1 ?
C14A C13A C12A . . 118.86(14) ?
C14A C13A H13A . . 120.6 ?
C12A C13A H13A . . 120.6 ?
C13A C14A F14A . . 119.12(14) ?
C13A C14A C15A . . 122.80(15) ?
F14A C14A C15A . . 118.09(15) ?
C14A C15A C16A . . 118.51(15) ?
C14A C15A H15A . . 120.7 ?
C16A C15A H15A . . 120.7 ?
C15A C16A C11A . . 120.03(14) ?
C15A C16A H16A . . 120.0 ?
C11A C16A H16A . . 120.0 ?
N22A C21A C26A . . 116.73(14) ?
N22A C21A C2A . . 118.07(14) ?
C26A C21A C2A . . 125.19(14) ?
C23A N22A C21A . . 123.85(14) ?
C23A N22A H22A . . 115.9(11) ?
C21A N22A H22A . . 120.2(11) ?
N22A C23A C24A . . 120.02(15) ?
N22A C23A H23A . . 120.0 ?
C24A C23A H23A . . 120.0 ?
C23A C24A C25A . . 118.54(16) ?
C23A C24A H24A . . 120.7 ?
C25A C24A H24A . . 120.7 ?
C26A C25A C24A . . 120.30(16) ?
C26A C25A H25A . . 119.8 ?
C24A C25A H25A . . 119.8 ?
C25A C26A C21A . . 120.55(15) ?
C25A C26A H26A . . 119.7 ?
C21A C26A H26A . . 119.7 ?
C1M O1M H1M . . 109.0(15) ?
O1M C1M H1M1 . . 109.5 ?
O1M C1M H1M2 . . 109.5 ?
H1M1 C1M H1M2 . . 109.5 ?
O1M C1M H1M3 . . 109.5 ?
H1M1 C1M H1M3 . . 109.5 ?
H1M2 C1M H1M3 . . 109.5 ?
C2M O2M H2M . . 105.1(19) ?
O2M C2M H2M1 . . 109.5 ?
O2M C2M H2M2 . . 109.5 ?
H2M1 C2M H2M2 . . 109.5 ?
O2M C2M H2M3 . . 109.5 ?
H2M1 C2M H2M3 . . 109.5 ?
H2M2 C2M H2M3 . . 109.5 ?
C3M O3M H3M . . 113.1(14) ?
O3M C3M H3MB . . 109.5 ?
O3M C3M H3MC . . 109.5 ?
H3MB C3M H3MC . . 109.5 ?
O3M C3M H3MD . . 109.5 ?
H3MB C3M H3MD . . 109.5 ?
H3MC C3M H3MD . . 109.5 ?
C4M O4M H4M . . 113.1(18) ?
O4M C4M H4M1 . . 109.5 ?
O4M C4M H4M2 . . 109.5 ?
H4M1 C4M H4M2 . . 109.5 ?
O4M C4M H4M3 . . 109.5 ?
H4M1 C4M H4M3 . . 109.5 ?
H4M2 C4M H4M3 . . 109.5 ?
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
N1 N2 . 1.3348(17) ?
N1 C11 . 1.398(2) ?
N1 H1 . 0.826(16) ?
N2 C2 . 1.2957(19) ?
C2 C21 . 1.462(2) ?
C2 C3 . 1.499(2) ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C11 C12 . 1.390(2) ?
C11 C16 . 1.394(2) ?
C12 C13 . 1.392(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.366(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.372(2) ?
C14 F14 . 1.3749(18) ?
C15 C16 . 1.386(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 N22 . 1.3521(18) ?
C21 C26 . 1.396(2) ?
N22 C23 . 1.347(2) ?
N22 H22 . 0.907(17) ?
C23 C24 . 1.370(2) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.382(2) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.374(2) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
N1A N2A . 1.3360(18) ?
N1A C11A . 1.404(2) ?
N1A H1A . 0.834(16) ?
N2A C2A . 1.296(2) ?
C2A C21A . 1.460(2) ?
C2A C3A . 1.502(2) ?
C3A H3A1 . 0.9800 ?
C3A H3A2 . 0.9800 ?
C3A H3A3 . 0.9800 ?
C11A C12A . 1.391(2) ?
C11A C16A . 1.396(2) ?
C12A C13A . 1.385(2) ?
C12A H12A . 0.9500 ?
C13A C14A . 1.369(2) ?
C13A H13A . 0.9500 ?
C14A F14A . 1.3719(18) ?
C14A C15A . 1.376(2) ?
C15A C16A . 1.380(2) ?
C15A H15A . 0.9500 ?
C16A H16A . 0.9500 ?
C21A N22A . 1.3548(18) ?
C21A C26A . 1.396(2) ?
N22A C23A . 1.344(2) ?
N22A H22A . 0.883(18) ?
C23A C24A . 1.371(2) ?
C23A H23A . 0.9500 ?
C24A C25A . 1.384(2) ?
C24A H24A . 0.9500 ?
C25A C26A . 1.378(2) ?
C25A H25A . 0.9500 ?
C26A H26A . 0.9500 ?
O1M C1M . 1.376(2) ?
O1M H1M . 0.92(3) ?
C1M H1M1 . 0.9800 ?
C1M H1M2 . 0.9800 ?
C1M H1M3 . 0.9800 ?
O2M C2M . 1.405(3) ?
O2M H2M . 0.91(3) ?
C2M H2M1 . 0.9800 ?
C2M H2M2 . 0.9800 ?
C2M H2M3 . 0.9800 ?
O3M C3M . 1.399(2) ?
O3M H3M . 0.86(2) ?
C3M H3MB . 0.9800 ?
C3M H3MC . 0.9800 ?
C3M H3MD . 0.9800 ?
O4M C4M . 1.408(3) ?
O4M H4M . 0.85(3) ?
C4M H4M1 . 0.9800 ?
C4M H4M2 . 0.9800 ?
C4M H4M3 . 0.9800 ?
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
N1 H1 O1M . 0.826(16) 2.158(16) 2.9136(17) 152.1(14)
N22 H22 Cl1 2_667 0.907(17) 2.401(16) 3.1633(15) 141.8(13)
N1A H1A O3M . 0.834(16) 2.081(17) 2.8806(18) 160.4(16)
N22A H22A Cl2 2_666 0.883(18) 2.382(18) 3.1292(15) 142.5(15)
O1M H1M Cl1 . 0.92(3) 2.18(3) 3.0807(16) 168(2)
O2M H2M Cl1 . 0.91(3) 2.19(3) 3.1029(17) 178(3)
O3M H3M Cl2 . 0.86(2) 2.21(2) 3.0678(16) 172(2)
O4M H4M Cl2 . 0.85(3) 2.30(3) 3.1329(18) 167(2)
C25 H25 O2M 2_557 0.9500 2.4200 3.315(2) 157.00
C25A H25A O4M 2_556 0.9500 2.4400 3.318(3) 153.00
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
C11 N1 N2 C2 . . . . -177.23(15) ?
N1 N2 C2 C21 . . . . -179.79(13) ?
N1 N2 C2 C3 . . . . 1.0(2) ?
N2 N1 C11 C12 . . . . -2.0(2) ?
N2 N1 C11 C16 . . . . 177.91(14) ?
C16 C11 C12 C13 . . . . 0.1(2) ?
N1 C11 C12 C13 . . . . -179.99(15) ?
C11 C12 C13 C14 . . . . -0.3(2) ?
C12 C13 C14 C15 . . . . 0.4(3) ?
C12 C13 C14 F14 . . . . -179.52(14) ?
C13 C14 C15 C16 . . . . -0.3(2) ?
F14 C14 C15 C16 . . . . 179.62(14) ?
C14 C15 C16 C11 . . . . 0.1(2) ?
C12 C11 C16 C15 . . . . 0.0(2) ?
N1 C11 C16 C15 . . . . -179.91(15) ?
N2 C2 C21 N22 . . . . -4.6(2) ?
C3 C2 C21 N22 . . . . 174.62(14) ?
N2 C2 C21 C26 . . . . 175.62(15) ?
C3 C2 C21 C26 . . . . -5.2(2) ?
C26 C21 N22 C23 . . . . -0.3(2) ?
C2 C21 N22 C23 . . . . 179.86(15) ?
C21 N22 C23 C24 . . . . 0.4(2) ?
N22 C23 C24 C25 . . . . -0.4(3) ?
C23 C24 C25 C26 . . . . 0.4(3) ?
C24 C25 C26 C21 . . . . -0.3(3) ?
N22 C21 C26 C25 . . . . 0.3(2) ?
C2 C21 C26 C25 . . . . -179.95(16) ?
C11A N1A N2A C2A . . . . -178.80(14) ?
N1A N2A C2A C21A . . . . 178.98(13) ?
N1A N2A C2A C3A . . . . -1.0(2) ?
N2A N1A C11A C12A . . . . -4.7(2) ?
N2A N1A C11A C16A . . . . 176.85(13) ?
C16A C11A C12A C13A . . . . 0.2(2) ?
N1A C11A C12A C13A . . . . -178.22(14) ?
C11A C12A C13A C14A . . . . -0.1(2) ?
C12A C13A C14A F14A . . . . -179.98(14) ?
C12A C13A C14A C15A . . . . -0.2(2) ?
C13A C14A C15A C16A . . . . 0.4(2) ?
F14A C14A C15A C16A . . . . -179.82(14) ?
C14A C15A C16A C11A . . . . -0.3(2) ?
C12A C11A C16A C15A . . . . 0.0(2) ?
N1A C11A C16A C15A . . . . 178.49(14) ?
N2A C2A C21A N22A . . . . 3.5(2) ?
C3A C2A C21A N22A . . . . -176.59(13) ?
N2A C2A C21A C26A . . . . -175.71(15) ?
C3A C2A C21A C26A . . . . 4.2(2) ?
C26A C21A N22A C23A . . . . -0.5(2) ?
C2A C21A N22A C23A . . . . -179.70(14) ?
C21A N22A C23A C24A . . . . 0.6(2) ?
N22A C23A C24A C25A . . . . -0.2(2) ?
C23A C24A C25A C26A . . . . -0.2(3) ?
C24A C25A C26A C21A . . . . 0.2(3) ?
N22A C21A C26A C25A . . . . 0.1(2) ?
C2A C21A C26A C25A . . . . 179.24(15) ?
