#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/09/2210970.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_2210970
loop_
_publ_author_name
'Boufas, Sihem'
'Merazig, Hocine'
'Bendjeddou, Lamia'
'Beghidja, Adel'
'Dénés, Georges'
_publ_section_title
;
 Naphthalene-1,5-diammonium dichloride
;
_journal_coeditor_code           DN2077
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5268
_journal_page_last               o5270
_journal_paper_doi               10.1107/S1600536806043868
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H12 N2 2+, 2Cl -'
_chemical_formula_moiety         'C10 H12 N2 2+, 2Cl -'
_chemical_formula_structural     'C10 H12 N2, Cl2'
_chemical_formula_sum            'C10 H12 Cl2 N2'
_chemical_formula_weight         231.12
_chemical_name_common            'Naphthalene-1,5-diammonium dichloride'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.3940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5766(4)
_cell_length_b                   5.1650(4)
_cell_length_c                   12.2001(7)
_cell_measurement_reflns_used    4491
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     527.85(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 1997)'
_computing_data_reduction
'HKL Denzo (Otwinowski & Minor 1997) and Scalepack'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,  2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and Parst (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       φ
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_theta_full        29.94
_diffrn_reflns_theta_max         29.94
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         1523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0161P)²+0.2248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                1265
_reflns_number_total             1523
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2077.cif
_cod_data_source_block           I
_cod_database_code               2210970
_cod_database_fobs_code          2210970
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_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
Cl Cl1 0.44779(5) 0.21431(7) 0.35441(3) 0.02071(13) Uani d . 1
N N1 0.34394(15) 0.2116(2) 0.08241(11) 0.0184(3) Uani d . 1
C C1 0.08397(17) 0.0054(3) 0.00288(13) 0.0148(3) Uani d . 1
C C2 0.17249(17) 0.1932(3) 0.07625(13) 0.0156(3) Uani d . 1
C C3 0.10277(19) 0.3564(3) 0.13922(13) 0.0189(3) Uani d . 1
C C4 -0.06309(19) 0.3425(3) 0.13258(13) 0.0197(3) Uani d . 1
C C5 -0.15455(19) 0.1658(3) 0.06337(13) 0.0185(3) Uani d . 1
H H1 -0.2639 0.1581 0.0598 0.022 Uiso calc R 1
H H2 -0.1108 0.4541 0.1755 0.024 Uiso calc R 1
H H3 0.1644 0.4765 0.1864 0.023 Uiso calc R 1
H H4 0.3615 0.2372 0.0139 0.035(6) Uiso calc R 1
H H5 0.391 0.0653 0.1105 0.035(5) Uiso calc R 1
H H6 0.3838 0.3435 0.1265 0.045(6) Uiso calc R 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
Cl1 0.0229(2) 0.0219(2) 0.0170(2) 0.00300(14) 0.00343(15) 0.00044(14)
N1 0.0157(6) 0.0213(7) 0.0174(7) -0.0035(5) 0.0021(5) -0.0014(5)
C1 0.0154(7) 0.0150(7) 0.0140(7) -0.0002(5) 0.0030(6) 0.0026(5)
C2 0.0138(7) 0.0175(7) 0.0150(7) -0.0015(5) 0.0019(6) 0.0025(6)
C3 0.0214(8) 0.0176(7) 0.0163(8) -0.0030(6) 0.0012(6) -0.0013(6)
C4 0.0221(8) 0.0186(8) 0.0192(8) 0.0025(6) 0.0059(6) -0.0018(6)
C5 0.0158(7) 0.0205(8) 0.0194(8) 0.0002(6) 0.0041(6) 0.0008(6)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_reflns_number
4124
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
C2 N1 H4 . . 109.5
C2 N1 H5 . . 109.5
H4 N1 H5 . . 109.5
C2 N1 H6 . . 109.5
H4 N1 H6 . . 109.5
H5 N1 H6 . . 109.5
C5 C1 C2 3 . 123.22(14)
C5 C1 C1 3 3 119.81(17)
C2 C1 C1 . 3 116.97(17)
C3 C2 C1 . . 122.47(14)
C3 C2 N1 . . 119.34(13)
C1 C2 N1 . . 118.18(13)
C2 C3 C4 . . 119.74(14)
C2 C3 H3 . . 120.1
C4 C3 H3 . . 120.1
C5 C4 C3 . . 120.44(15)
C5 C4 H2 . . 119.8
C3 C4 H2 . . 119.8
C4 C5 C1 . 3 120.58(14)
C4 C5 H1 . . 119.7
C1 C5 H1 3 . 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.4593(19)
N1 H4 . 0.89
N1 H5 . 0.89
N1 H6 . 0.89
C1 C1 3 1.428(3)
C1 C2 . 1.424(2)
C3 C2 . 1.362(2)
C3 C4 . 1.409(2)
C3 H3 . 0.93
C4 C5 . 1.370(2)
C4 H2 . 0.93
C5 C1 3 1.418(2)
C5 H1 . 0.93
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
N(1) H(4) Cl(1) 4_565 0.8900 2.2400 3.1210(14) 171.00
N(1) H(5) Cl(1) 2_645 0.8900 2.2600 3.1291(12) 164.00
N(1) H(6) Cl(1) 1_555 0.8900 2.8000 3.2460(14) 113.00
N(1) H(6) Cl(1) 2_655 0.8900 2.3800 3.1521(12) 145.00
