#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/31/2203125.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_2203125
loop_
_publ_author_name
'Bernès, Sylvain'
'Rodríguez Pastrana, Modesto'
'Huerta Sánchez, Enrique'
'Gutiérrez Pérez, René'
_publ_section_title
;
 1,5-Diaminonaphthalene
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o45
_journal_page_last               o47
_journal_paper_doi               10.1107/S1600536803026643
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H10 N2'
_chemical_formula_moiety         'C10 H10 N2'
_chemical_formula_sum            'C10 H10 N2'
_chemical_formula_weight         158.20
_chemical_melting_point          458
_chemical_name_common            1,5-Diaminonaphthalene
_chemical_name_systematic        1,5-Diaminonaphthalene
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-Plus
_cell_angle_alpha                90
_cell_angle_beta                 90.679(10)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   5.1790(7)
_cell_length_b                   11.0081(18)
_cell_length_c                   21.238(3)
_cell_measurement_reflns_used    75
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      11.88
_cell_measurement_theta_min      5.13
_cell_volume                     1210.7(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1998)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.042
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3277
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.13
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL-Plus (Sheldrick, 1998)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.081
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0551P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.118
_reflns_number_gt                1259
_reflns_number_total             2117
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6193.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom + difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2203125
_cod_database_fobs_code          2203125
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_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_type_symbol
N1 0.1882(4) 0.7292(2) 0.14149(12) 0.0745(6) Uani d . 1 N
H1A 0.130(5) 0.764(2) 0.1771(12) 0.089(9) Uiso d . 1 H
H1B 0.076(4) 0.723(2) 0.1124(10) 0.081(8) Uiso d . 1 H
C1 0.3564(4) 0.63152(18) 0.14524(9) 0.0594(6) Uani d . 1 C
C2 0.3801(5) 0.5513(2) 0.09579(9) 0.0722(6) Uani d . 1 C
H2A 0.2713 0.5587 0.0608 0.087 Uiso calc R 1 H
C3 0.5650(5) 0.4593(2) 0.09746(10) 0.0759(7) Uani d . 1 C
H3A 0.5775 0.4066 0.0634 0.091 Uiso calc R 1 H
C4 0.7272(4) 0.44450(18) 0.14756(9) 0.0661(6) Uani d . 1 C
H4A 0.8502 0.3830 0.1473 0.079 Uiso calc R 1 H
C5 0.8711(4) 0.51086(18) 0.25458(9) 0.0564(5) Uani d . 1 C
N5 1.0532(4) 0.41626(19) 0.25897(13) 0.0747(6) Uani d . 1 N
H5A 1.108(5) 0.397(2) 0.2196(12) 0.104(10) Uiso d . 1 H
H5B 1.158(5) 0.430(2) 0.2900(11) 0.085(9) Uiso d . 1 H
C6 0.8388(4) 0.58686(19) 0.30511(9) 0.0632(6) Uani d . 1 C
H6A 0.9440 0.5777 0.3406 0.076 Uiso calc R 1 H
C7 0.6508(4) 0.67771(19) 0.30422(9) 0.0614(6) Uani d . 1 C
H7A 0.6322 0.7278 0.3392 0.074 Uiso calc R 1 H
C8 0.4946(4) 0.69413(18) 0.25311(9) 0.0583(5) Uani d . 1 C
H8A 0.3712 0.7555 0.2531 0.070 Uiso calc R 1 H
C9 0.5196(4) 0.61744(16) 0.19953(8) 0.0507(5) Uani d . 1 C
C10 0.7086(4) 0.52369(17) 0.20057(8) 0.0528(5) Uani d . 1 C
N11 0.5825(4) 0.5536(3) 0.59806(9) 0.0740(6) Uani d . 1 N
H11A 0.534(5) 0.481(2) 0.5995(11) 0.089(9) Uiso d . 1 H
H11B 0.462(5) 0.614(2) 0.6061(10) 0.091(8) Uiso d . 1 H
C11 0.7452(4) 0.5774(2) 0.54805(8) 0.0566(5) Uani d . 1 C
C12 0.7622(4) 0.69414(19) 0.52448(9) 0.0638(6) Uani d . 1 C
H12A 0.6519 0.7540 0.5394 0.077 Uiso calc R 1 H
C13 0.9433(4) 0.7233(2) 0.47848(9) 0.0660(6) Uani d . 1 C
H13A 0.9521 0.8024 0.4632 0.079 Uiso calc R 1 H
C14 1.1068(4) 0.63739(19) 0.45573(9) 0.0610(6) Uani d . 1 C
H14A 1.2299 0.6590 0.4262 0.073 Uiso calc R 1 H
C20 1.0915(3) 0.51567(18) 0.47650(8) 0.0509(5) Uani d . 1 C
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 1 3
-1 -2 2
1 0 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
C1 N1 H1A . . 119.7(15) y
C1 N1 H1B . . 113.7(16) y
H1A N1 H1B . . 114(2) y
C2 C1 N1 . . 121.0(2) n
C2 C1 C9 . . 119.2(2) n
N1 C1 C9 . . 119.72(19) n
C1 C2 C3 . . 120.9(2) n
C1 C2 H2A . . 119.6 n
C3 C2 H2A . . 119.6 n
C4 C3 C2 . . 121.7(2) n
C4 C3 H3A . . 119.1 n
C2 C3 H3A . . 119.1 n
C3 C4 C10 . . 119.9(2) n
C3 C4 H4A . . 120.1 n
C10 C4 H4A . . 120.1 n
C6 C5 N5 . . 119.1(2) n
C6 C5 C10 . . 119.60(18) n
N5 C5 C10 . . 121.1(2) n
C5 N5 H5A . . 108.9(16) y
C5 N5 H5B . . 109.6(17) y
H5A N5 H5B . . 123(2) y
C5 C6 C7 . . 121.17(19) n
C5 C6 H6A . . 119.4 n
C7 C6 H6A . . 119.4 n
C8 C7 C6 . . 121.00(18) n
C8 C7 H7A . . 119.5 n
C6 C7 H7A . . 119.5 n
C7 C8 C9 . . 120.05(19) n
C7 C8 H8A . . 120.0 n
C9 C8 H8A . . 120.0 n
C10 C9 C8 . . 119.13(17) n
C10 C9 C1 . . 119.43(17) n
C8 C9 C1 . . 121.43(19) n
C5 C10 C9 . . 119.04(17) n
C5 C10 C4 . . 122.05(19) n
C9 C10 C4 . . 118.90(18) n
C11 N11 H11A . . 113.1(17) y
C11 N11 H11B . . 114.8(14) y
H11A N11 H11B . . 118(2) y
C12 C11 N11 . . 119.6(2) n
C12 C11 C20 . 3_766 119.55(18) n
N11 C11 C20 . 3_766 120.7(2) n
C11 C12 C13 . . 120.8(2) n
C11 C12 H12A . . 119.6 n
C13 C12 H12A . . 119.6 n
C14 C13 C12 . . 120.8(2) n
C14 C13 H13A . . 119.6 n
C12 C13 H13A . . 119.6 n
C13 C14 C20 . . 120.69(19) n
C13 C14 H14A . . 119.7 n
C20 C14 H14A . . 119.7 n
C14 C20 C20 . 3_766 119.2(2) n
C14 C20 C11 . 3_766 121.97(18) n
C20 C20 C11 3_766 3_766 118.8(2) n
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 C1 . 1.385(3) y
N1 H1A . 0.90(2) y
N1 H1B . 0.85(2) y
C1 C2 . 1.379(3) n
C1 C9 . 1.430(3) n
C2 C3 . 1.394(3) n
C2 H2A . 0.9300 n
C3 C4 . 1.358(3) n
C3 H3A . 0.9300 n
C4 C10 . 1.428(3) n
C4 H4A . 0.9300 n
C5 C6 . 1.373(3) n
C5 N5 . 1.407(3) y
C5 C10 . 1.421(3) n
N5 H5A . 0.91(2) y
N5 H5B . 0.86(2) y
C6 C7 . 1.396(3) n
C6 H6A . 0.9300 n
C7 C8 . 1.358(3) n
C7 H7A . 0.9300 n
C8 C9 . 1.424(2) n
C8 H8A . 0.9300 n
C9 C10 . 1.423(3) n
N11 C11 . 1.388(3) y
N11 H11A . 0.84(3) y
N11 H11B . 0.93(3) y
C11 C12 . 1.383(3) n
C11 C20 3_766 1.431(3) n
C12 C13 . 1.400(3) n
C12 H12A . 0.9300 n
C13 C14 . 1.362(3) n
C13 H13A . 0.9300 n
C14 C20 . 1.413(3) n
C14 H14A . 0.9300 n
C20 C20 3_766 1.427(4) n
C20 C11 3_766 1.431(3) n
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_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . 174.46(19) n
C9 C1 C2 C3 . . -1.7(3) n
C1 C2 C3 C4 . . 0.3(3) n
C2 C3 C4 C10 . . 0.7(3) n
N5 C5 C6 C7 . . -176.45(19) n
C10 C5 C6 C7 . . -0.7(3) n
C5 C6 C7 C8 . . -0.3(3) n
C6 C7 C8 C9 . . 0.5(3) n
C7 C8 C9 C10 . . 0.3(3) n
C7 C8 C9 C1 . . 179.34(17) n
C2 C1 C9 C10 . . 2.1(3) n
N1 C1 C9 C10 . . -174.14(17) n
C2 C1 C9 C8 . . -176.94(17) n
N1 C1 C9 C8 . . 6.8(3) n
C6 C5 C10 C9 . . 1.5(3) n
N5 C5 C10 C9 . . 177.18(17) n
C6 C5 C10 C4 . . -177.73(17) n
N5 C5 C10 C4 . . -2.1(3) n
C8 C9 C10 C5 . . -1.3(3) n
C1 C9 C10 C5 . . 179.61(16) n
C8 C9 C10 C4 . . 177.96(16) n
C1 C9 C10 C4 . . -1.1(3) n
C3 C4 C10 C5 . . 178.98(18) n
C3 C4 C10 C9 . . -0.3(3) n
N11 C11 C12 C13 . . 173.49(18) n
C20 C11 C12 C13 3_766 . -2.2(3) n
C11 C12 C13 C14 . . 0.1(3) n
C12 C13 C14 C20 . . 2.2(3) n
C13 C14 C20 C20 . 3_766 -2.3(3) n
C13 C14 C20 C11 . 3_766 177.89(17) n
