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#$Date: 2022-09-26 12:34:48 +0300 (Mon, 26 Sep 2022) $
#$Revision: 278183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/58/8105873.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_8105873
loop_
_publ_author_name
'Said, Musa A.'
'Hughes, David L.'
'Almutairi, Saud M.'
'Aouad, Mohamed Reda'
'Messali, Mouslim'
_publ_section_title
;
 Crystal structure of 1-nonylpyridazin-1-ium iodide, C13H23N2I
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              857
_journal_page_last               859
_journal_paper_doi               10.1515/ncrs-2019-0024
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C13 H23 N2, I'
_chemical_formula_structural     'n-nonyl-pyridazinium iodide'
_chemical_formula_sum            'C13 H23 I N2'
_chemical_formula_weight         334.23
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                83.341(4)
_cell_angle_beta                 89.534(4)
_cell_angle_gamma                82.491(4)
_cell_formula_units_Z            2
_cell_length_a                   5.6693(3)
_cell_length_b                   8.9457(4)
_cell_length_c                   16.2919(7)
_cell_measurement_reflns_used    3176
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3900
_cell_measurement_theta_min      3.2070
_cell_volume                     813.63(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material
'SHELXL-2014/7 (Sheldrick, 2015b) and WINGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      293(1)
_diffrn_detector_area_resol_mean 16.0050
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/Sapphire3 CCD'
_diffrn_measurement_method       'Thin slice φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10743
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         3.611
_exptl_absorpt_coefficient_mu    1.950
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
 Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0446
_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)+(0.0330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0873
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2345
_reflns_number_total             2866
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0024_suppl.cif
_cod_data_source_block           musa37
_cod_database_code               8105873
_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.
;
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_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_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
I I 0.11316(6) 0.74147(3) 0.42796(2) 0.06645(16) Uani 1 1 d . . . . .
N1 N 0.3798(7) 0.6652(4) 0.6368(2) 0.0559(10) Uani 1 1 d . . . . .
N2 N 0.2229(7) 0.7671(4) 0.6679(3) 0.0639(11) Uani 1 1 d . . . . .
C3 C 0.2714(10) 0.9060(6) 0.6580(3) 0.0751(15) Uani 1 1 d . . . . .
H3 H 0.1651 0.9803 0.6789 0.090 Uiso 1 1 calc R U . . .
C4 C 0.4726(10) 0.9501(6) 0.6180(3) 0.0725(15) Uani 1 1 d . . . . .
H4 H 0.5005 1.0509 0.6124 0.087 Uiso 1 1 calc R U . . .
C5 C 0.6252(9) 0.8435(7) 0.5878(3) 0.0702(14) Uani 1 1 d . . . . .
H5 H 0.7635 0.8676 0.5613 0.084 Uiso 1 1 calc R U . . .
C6 C 0.5710(9) 0.6964(6) 0.5972(3) 0.0651(13) Uani 1 1 d . . . . .
H6 H 0.6706 0.6200 0.5754 0.078 Uiso 1 1 calc R U . . .
C11 C 0.3125(10) 0.5107(5) 0.6461(3) 0.0749(15) Uani 1 1 d . . . . .
H11A H 0.4314 0.4441 0.6199 0.090 Uiso 1 1 calc R U . . .
H11B H 0.1618 0.5119 0.6180 0.090 Uiso 1 1 calc R U . . .
C12 C 0.2904(11) 0.4490(7) 0.7349(4) 0.0850(17) Uani 1 1 d . . . . .
H12A H 0.2360 0.3502 0.7376 0.102 Uiso 1 1 calc R U . . .
H12B H 0.1708 0.5156 0.7608 0.102 Uiso 1 1 calc R U . . .
C13 C 0.5189(11) 0.4337(7) 0.7827(4) 0.0915(18) Uani 1 1 d . . . . .
H13A H 0.5616 0.5342 0.7864 0.110 Uiso 1 1 calc R U . . .
H13B H 0.6436 0.3791 0.7525 0.110 Uiso 1 1 calc R U . . .
C14 C 0.5080(12) 0.3514(8) 0.8698(4) 0.101(2) Uani 1 1 d . . . . .
H14A H 0.3866 0.4074 0.9007 0.121 Uiso 1 1 calc R U . . .
H14B H 0.4616 0.2516 0.8664 0.121 Uiso 1 1 calc R U . . .
C15 C 0.7394(13) 0.3337(8) 0.9156(4) 0.111(2) Uani 1 1 d . . . . .
H15A H 0.7811 0.4338 0.9214 0.133 Uiso 1 1 calc R U . . .
H15B H 0.8623 0.2830 0.8829 0.133 Uiso 1 1 calc R U . . .
C16 C 0.7371(13) 0.2453(9) 1.0001(4) 0.115(2) Uani 1 1 d . . . . .
H16A H 0.6902 0.1465 0.9945 0.138 Uiso 1 1 calc R U . . .
H16B H 0.6183 0.2979 1.0335 0.138 Uiso 1 1 calc R U . . .
C17 C 0.9766(14) 0.2234(9) 1.0449(4) 0.120(2) Uani 1 1 d . . . . .
H17A H 1.0963 0.1747 1.0103 0.144 Uiso 1 1 calc R U . . .
H17B H 1.0201 0.3224 1.0522 0.144 Uiso 1 1 calc R U . . .
C18 C 0.9802(14) 0.1309(11) 1.1273(4) 0.140(3) Uani 1 1 d . . . . .
H18A H 0.9368 0.0319 1.1200 0.168 Uiso 1 1 calc R U . . .
H18B H 0.8604 0.1795 1.1619 0.168 Uiso 1 1 calc R U . . .
C19 C 1.2147(15) 0.1097(11) 1.1712(5) 0.159(4) Uani 1 1 d . . . . .
H19A H 1.2032 0.0494 1.2234 0.238 Uiso 1 1 calc R U . . .
H19B H 1.3340 0.0591 1.1382 0.238 Uiso 1 1 calc R U . . .
H19C H 1.2575 0.2069 1.1801 0.238 Uiso 1 1 calc R U . . .
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'
I I -0.4742 1.8119 '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
C6 N1 N2 124.6(4) . .
C6 N1 C11 121.3(4) . .
N2 N1 C11 114.0(4) . .
C3 N2 N1 115.9(4) . .
N2 C3 C4 123.8(5) . .
N2 C3 H3 118.1 . .
C4 C3 H3 118.1 . .
C5 C4 C3 118.1(5) . .
C5 C4 H4 120.9 . .
C3 C4 H4 120.9 . .
C4 C5 C6 117.9(5) . .
C4 C5 H5 121.1 . .
C6 C5 H5 121.1 . .
N1 C6 C5 119.7(5) . .
N1 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
N1 C11 C12 112.2(4) . .
N1 C11 H11A 109.2 . .
C12 C11 H11A 109.2 . .
N1 C11 H11B 109.2 . .
C12 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
C11 C12 C13 113.4(5) . .
C11 C12 H12A 108.9 . .
C13 C12 H12A 108.9 . .
C11 C12 H12B 108.9 . .
C13 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C12 C13 C14 113.9(5) . .
C12 C13 H13A 108.8 . .
C14 C13 H13A 108.8 . .
C12 C13 H13B 108.8 . .
C14 C13 H13B 108.8 . .
H13A C13 H13B 107.7 . .
C15 C14 C13 113.0(5) . .
C15 C14 H14A 109.0 . .
C13 C14 H14A 109.0 . .
C15 C14 H14B 109.0 . .
C13 C14 H14B 109.0 . .
H14A C14 H14B 107.8 . .
C14 C15 C16 114.1(6) . .
C14 C15 H15A 108.7 . .
C16 C15 H15A 108.7 . .
C14 C15 H15B 108.7 . .
C16 C15 H15B 108.7 . .
H15A C15 H15B 107.6 . .
C15 C16 C17 113.6(6) . .
C15 C16 H16A 108.9 . .
C17 C16 H16A 108.9 . .
C15 C16 H16B 108.9 . .
C17 C16 H16B 108.9 . .
H16A C16 H16B 107.7 . .
C18 C17 C16 114.3(7) . .
C18 C17 H17A 108.7 . .
C16 C17 H17A 108.7 . .
C18 C17 H17B 108.7 . .
C16 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C17 C18 C19 114.3(7) . .
C17 C18 H18A 108.7 . .
C19 C18 H18A 108.7 . .
C17 C18 H18B 108.7 . .
C19 C18 H18B 108.7 . .
H18A C18 H18B 107.6 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.302(6) .
N1 N2 1.329(5) .
N1 C11 1.472(6) .
N2 C3 1.300(6) .
C3 C4 1.388(7) .
C3 H3 0.9300 .
C4 C5 1.336(7) .
C4 H4 0.9300 .
C5 C6 1.381(7) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C11 C12 1.498(7) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.499(8) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.527(8) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.495(8) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.507(9) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.526(9) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.492(9) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.494(10) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
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
C3 H3 I 0.93 3.12 3.726(5) 124.5 2_576
C4 H4 I 0.93 3.07 3.857(5) 143.2 2_676
C5 H5 I 0.93 3.14 3.879(6) 138.1 1_655
C6 H6 I 0.93 3.31 4.153(5) 151.5 2_666
C11 H11A I 0.97 3.03 3.974(6) 165.0 2_666
C11 H11B I 0.97 3.08 3.803(5) 132.8 2_566
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
C6 N1 N2 C3 -1.1(7) . . . .
C11 N1 N2 C3 -177.4(4) . . . .
N1 N2 C3 C4 -0.1(8) . . . .
N2 C3 C4 C5 0.1(8) . . . .
C3 C4 C5 C6 1.0(8) . . . .
N2 N1 C6 C5 2.2(7) . . . .
C11 N1 C6 C5 178.3(4) . . . .
C4 C5 C6 N1 -2.1(7) . . . .
C6 N1 C11 C12 122.2(5) . . . .
N2 N1 C11 C12 -61.4(6) . . . .
N1 C11 C12 C13 -62.3(6) . . . .
C11 C12 C13 C14 -172.1(5) . . . .
C12 C13 C14 C15 178.5(6) . . . .
C13 C14 C15 C16 -176.8(6) . . . .
C14 C15 C16 C17 178.0(6) . . . .
C15 C16 C17 C18 -177.7(7) . . . .
C16 C17 C18 C19 -179.9(8) . . . .
