#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/67/2016751.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_2016751
loop_
_publ_author_name
'Lemmerer, Andreas'
'Billing, David G.'
'Robinson, Janine M.'
_publ_section_title
;
 Hydrogen-bonding one-dimensional chains containing the
 R₄²(8) motif in the ammonium salts 1-naphthylammonium
 iodide and naphthalene-1,8-diyldiammonium diiodide
;
_journal_coeditor_code           DN3092
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o481
_journal_page_last               o484
_journal_paper_doi               10.1107/S0108270108023561
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H12 N2 2+, 2I -'
_chemical_formula_moiety         'C10 H12 N2 2+, 2(I -)'
_chemical_formula_sum            'C10 H12 I2 N2'
_chemical_formula_weight         414.02
_chemical_name_systematic
;
naphthalene-1,8-diyldiammonium diiodide
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                68.082(3)
_cell_angle_beta                 75.764(3)
_cell_angle_gamma                68.867(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2529(13)
_cell_length_b                   9.1586(17)
_cell_length_c                   10.897(2)
_cell_measurement_reflns_used    756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.921
_cell_measurement_theta_min      2.688
_cell_volume                     621.2(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3479
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.03
_exptl_absorpt_correction_T_max  0.8136
_exptl_absorpt_correction_T_min  0.1192
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'XPREP (Bruker, 1999)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.444
_refine_diff_density_min         -1.536
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0785P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                1901
_reflns_number_total             2288
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3092.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2016751
_cod_database_fobs_code          2016751
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
C C1 0.2687(9) 0.3364(7) 0.8021(6) 0.0321(12) Uani d . 1
C C2 0.2656(10) 0.4149(9) 0.8864(7) 0.0431(16) Uani d . 1
H H2 0.2757 0.5215 0.8515 0.052 Uiso calc R 1
C C3 0.2476(11) 0.3392(10) 1.0253(7) 0.0520(18) Uani d . 1
H H3 0.2388 0.3963 1.0824 0.062 Uiso calc R 1
C C4 0.2433(10) 0.1802(10) 1.0741(6) 0.0465(17) Uani d . 1
H H4 0.2374 0.127 1.1657 0.056 Uiso calc R 1
C C4A 0.2478(8) 0.0933(8) 0.9886(6) 0.0357(14) Uani d . 1
C C4B 0.2517(8) 0.1729(7) 0.8480(6) 0.0295(12) Uani d . 1
C C5 0.2467(9) -0.0741(9) 1.0438(7) 0.0466(17) Uani d . 1
H H5 0.2465 -0.1253 1.1353 0.056 Uiso calc R 1
C C6 0.2460(11) -0.1601(9) 0.9676(7) 0.0489(17) Uani d . 1
H H6 0.2516 -0.2707 1.0054 0.059 Uiso calc R 1
C C7 0.2366(10) -0.0816(8) 0.8303(7) 0.0423(15) Uani d . 1
H H7 0.229 -0.1388 0.7778 0.051 Uiso calc R 1
C C8 0.2386(9) 0.0799(7) 0.7730(6) 0.0313(12) Uani d . 1
N N1 0.2955(8) 0.4271(6) 0.6597(5) 0.0346(11) Uani d . 1
H H1A 0.1853 0.4513 0.6248 0.052 Uiso calc R 1
H H1B 0.3977 0.3653 0.6187 0.052 Uiso calc R 1
H H1C 0.32 0.52 0.6489 0.052 Uiso calc R 1
N N2 0.2103(8) 0.1536(6) 0.6314(5) 0.0368(12) Uani d . 1
H H2A 0.3155 0.1862 0.5843 0.055 Uiso calc R 1
H H2B 0.1011 0.24 0.6214 0.055 Uiso calc R 1
H H2C 0.1973 0.0791 0.6026 0.055 Uiso calc R 1
I I1 -0.21945(6) 0.50509(5) 0.67326(4) 0.03958(18) Uani d . 1
I I2 0.71599(6) 0.15113(5) 0.52851(4) 0.04057(18) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.033(3) 0.033(3) 0.027(3) -0.008(3) -0.004(2) -0.008(2)
C2 0.049(4) 0.048(4) 0.035(4) -0.017(3) -0.002(3) -0.017(3)
C3 0.057(4) 0.073(5) 0.032(4) -0.015(4) -0.005(3) -0.028(4)
C4 0.048(4) 0.070(5) 0.019(3) -0.021(4) -0.005(3) -0.007(3)
C4A 0.027(3) 0.043(4) 0.026(3) -0.004(3) -0.006(3) -0.003(3)
C4B 0.024(3) 0.034(3) 0.027(3) -0.006(2) -0.001(2) -0.010(2)
C5 0.038(3) 0.047(4) 0.031(4) -0.010(3) -0.006(3) 0.011(3)
C6 0.053(4) 0.036(4) 0.040(4) -0.016(3) -0.005(3) 0.007(3)
C7 0.052(4) 0.037(3) 0.036(4) -0.019(3) 0.004(3) -0.010(3)
C8 0.036(3) 0.032(3) 0.022(3) -0.012(3) -0.004(2) -0.001(2)
N1 0.049(3) 0.028(2) 0.024(3) -0.016(2) 0.000(2) -0.003(2)
N2 0.056(3) 0.034(3) 0.022(3) -0.019(3) -0.004(2) -0.006(2)
I1 0.0487(3) 0.0442(3) 0.0232(3) -0.0154(2) -0.00624(19) -0.00518(19)
I2 0.0446(3) 0.0342(3) 0.0411(3) -0.0093(2) -0.0034(2) -0.0136(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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C2 C1 C4B 122.6(6)
C2 C1 N1 116.0(5)
C4B C1 N1 121.4(5)
C1 C2 C3 121.6(7)
C1 C2 H2 119.2
C3 C2 H2 119.2
C4 C3 C2 118.3(6)
C4 C3 H3 120.9
C2 C3 H3 120.9
C3 C4 C4A 121.6(6)
C3 C4 H4 119.2
C4A C4 H4 119.2
C4 C4A C5 119.7(6)
C4 C4A C4B 120.5(6)
C5 C4A C4B 119.8(6)
C8 C4B C4A 116.0(5)
C8 C4B C1 128.9(5)
C4A C4B C1 115.1(5)
C6 C5 C4A 121.9(6)
C6 C5 H5 119.1
C4A C5 H5 119.1
C5 C6 C7 119.5(6)
C5 C6 H6 120.3
C7 C6 H6 120.3
C8 C7 C6 120.3(6)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C4B 122.3(6)
C7 C8 N2 115.4(5)
C4B C8 N2 122.1(5)
C1 N1 H1A 109.5
C1 N1 H1B 109.5
H1A N1 H1B 109.5
C1 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C8 N2 H2A 109.5
C8 N2 H2B 109.5
H2A N2 H2B 109.5
C8 N2 H2C 109.5
H2A N2 H2C 109.5
H2B N2 H2C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.353(8)
C1 C4B 1.432(8)
C1 N1 1.464(7)
C2 C3 1.405(10)
C2 H2 0.93
C3 C4 1.360(10)
C3 H3 0.93
C4 C4A 1.423(9)
C4 H4 0.93
C4A C5 1.424(9)
C4A C4B 1.428(8)
C4B C8 1.421(8)
C5 C6 1.344(10)
C5 H5 0.93
C6 C7 1.404(9)
C6 H6 0.93
C7 C8 1.378(9)
C7 H7 0.93
C8 N2 1.468(7)
N1 H1A 0.89
N1 H1B 0.89
N1 H1C 0.89
N2 H2A 0.89
N2 H2B 0.89
N2 H2C 0.89
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 H1A I1 . 0.89 2.74 3.517(5) 146
N1 H1B I2 . 0.89 2.68 3.568(5) 172
N1 H1C I2 2_666 0.89 2.87 3.615(5) 143
N2 H2A I2 . 0.89 2.74 3.556(5) 153
N2 H2B I1 . 0.89 2.82 3.668(5) 161
N2 H2C I2 2_656 0.89 2.78 3.634(5) 161
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
C4B C1 C2 C3 0.7(10)
N1 C1 C2 C3 -177.8(6)
C1 C2 C3 C4 3.3(11)
C2 C3 C4 C4A -2.8(11)
C3 C4 C4A C5 178.9(6)
C3 C4 C4A C4B -1.6(10)
C4 C4A C4B C8 -174.8(5)
C5 C4A C4B C8 4.7(8)
C4 C4A C4B C1 5.3(8)
C5 C4A C4B C1 -175.2(5)
C2 C1 C4B C8 175.2(6)
N1 C1 C4B C8 -6.4(9)
C2 C1 C4B C4A -4.9(9)
N1 C1 C4B C4A 173.5(5)
C4 C4A C5 C6 178.4(6)
C4B C4A C5 C6 -1.1(10)
C4A C5 C6 C7 -3.0(11)
C5 C6 C7 C8 3.4(11)
C6 C7 C8 C4B 0.5(10)
C6 C7 C8 N2 -174.8(6)
C4A C4B C8 C7 -4.5(9)
C1 C4B C8 C7 175.4(6)
C4A C4B C8 N2 170.6(5)
C1 C4B C8 N2 -9.5(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654120
