#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238044.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_2238044
loop_
_publ_author_name
'Benaouida, Mohamed Amine'
'Chetioui, Souheyla'
'Bouaoud, Salah Eddine'
_publ_section_title
;
 1-(4-Hydroxyphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium methanol
 hemisolvate
;
_journal_coeditor_code           SU2594
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o867
_journal_page_last               o868
_journal_paper_doi               10.1107/S1600536813012245
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H12 N2 O2, 0.5C H4 O'
_chemical_formula_moiety         'C16 H12 N2 O2, 0.5(C H4 O)'
_chemical_formula_sum            'C16.5 H14 N2 O2.5'
_chemical_formula_weight         280.30
_chemical_name_systematic
;
1-(4-Hydroxyphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium methanol hemisolvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.985(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.942(7)
_cell_length_b                   6.3479(17)
_cell_length_c                   17.579(5)
_cell_measurement_reflns_used    1832
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.40
_cell_volume                     2746.8(13)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12992
_diffrn_reflns_theta_full        30.74
_diffrn_reflns_theta_max         30.74
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0524
_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)+(0.0652P)²+0.3604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                2286
_reflns_number_total             4212
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2594.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C16.50 H14 N2 O2.50'
_cod_database_code               2238044
_cod_database_fobs_code          2238044
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.05411(5) 0.9010(2) 0.10115(8) 0.0693(5) Uani d . 1.000
O O2 0.09325(5) 1.7942(2) -0.17549(9) 0.0775(5) Uani d . 1.000
N N1 0.13875(5) 0.98315(19) 0.04654(7) 0.0426(4) Uani d . 1.000
N N2 0.09869(5) 1.1128(2) 0.02339(7) 0.0454(4) Uani d . 1.000
C C1 0.13793(5) 0.8158(2) 0.09375(8) 0.0408(4) Uani d . 1.000
C C2 0.09520(6) 0.7749(3) 0.12016(10) 0.0516(5) Uani d . 1.000
C C3 0.09810(7) 0.5873(3) 0.16635(10) 0.0563(6) Uani d . 1.000
C C4 0.13956(6) 0.4517(3) 0.18484(9) 0.0510(5) Uani d . 1.000
C C5 0.18354(6) 0.4878(2) 0.16088(8) 0.0439(5) Uani d . 1.000
C C6 0.18351(5) 0.6722(2) 0.11622(8) 0.0402(4) Uani d . 1.000
C C7 0.22698(6) 0.3453(3) 0.18175(9) 0.0529(5) Uani d . 1.000
C C8 0.26920(7) 0.3855(3) 0.16014(10) 0.0590(6) Uani d . 1.000
C C9 0.26971(6) 0.5681(3) 0.11681(10) 0.0565(6) Uani d . 1.000
C C10 0.22765(6) 0.7090(3) 0.09506(9) 0.0482(5) Uani d . 1.000
C C11 0.09846(5) 1.2857(2) -0.02644(8) 0.0421(4) Uani d . 1.000
C C12 0.05513(6) 1.4243(3) -0.04920(10) 0.0505(5) Uani d . 1.000
C C13 0.05257(6) 1.5962(3) -0.09868(10) 0.0555(5) Uani d . 1.000
C C14 0.09319(6) 1.6298(2) -0.12578(9) 0.0507(5) Uani d . 1.000
C C15 0.13698(6) 1.4922(2) -0.10218(9) 0.0497(5) Uani d . 1.000
C C16 0.13961(6) 1.3214(2) -0.05285(9) 0.0467(5) Uani d . 1.000
O O1S -0.00722(9) 2.0049(3) -0.21505(14) 0.0490(7) Uani d P 0.500
C C1S 0.00000 2.1846(5) -0.25000 0.0803(14) Uani d S 1.000
H H2A 0.07230 1.09380 0.03830 0.0540 Uiso c R 1.000
H H2B 0.06390 1.85490 -0.19190 0.1160 Uiso c R 1.000
H H3A 0.07060 0.55830 0.18400 0.0680 Uiso c R 1.000
H H4A 0.13970 0.32990 0.21430 0.0610 Uiso c R 1.000
H H7A 0.22690 0.22250 0.21060 0.0630 Uiso c R 1.000
H H8A 0.29780 0.29040 0.17440 0.0710 Uiso c R 1.000
H H9A 0.29880 0.59470 0.10250 0.0680 Uiso c R 1.000
H H10A 0.22840 0.83040 0.06590 0.0580 Uiso c R 1.000
H H12A 0.02760 1.40130 -0.03110 0.0610 Uiso c R 1.000
H H13A 0.02350 1.68920 -0.11370 0.0670 Uiso c R 1.000
H H15A 0.16470 1.51600 -0.11990 0.0600 Uiso c R 1.000
H H16A 0.16900 1.22980 -0.03720 0.0560 Uiso c R 1.000
H H1SA -0.035(2) 2.289(9) -0.284(3) 0.1210 Uiso d P 0.500
H H1O -0.02100 2.04990 -0.17790 0.0740 Uiso d RP 0.500
H H1SB 0.0081(13) 2.124(4) -0.2876(18) 0.1210 Uiso d . 1.000
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'
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
C14 O2 H2B . . 109.00 no
C1S O1S H1O . . 104.00 no
C1S O1S H1SB . 2_554 37(2) no
H1O O1S H1SB . 2_554 67.00 no
N2 N1 C1 . . 118.42(14) no
N1 N2 C11 . . 119.27(13) no
N1 N2 H2A . . 120.00 no
C11 N2 H2A . . 120.00 no
C2 C1 C6 . . 120.15(13) no
N1 C1 C2 . . 123.90(14) no
N1 C1 C6 . . 115.94(13) no
O1 C2 C1 . . 121.39(16) no
O1 C2 C3 . . 120.43(16) no
C1 C2 C3 . . 118.16(16) no
C2 C3 C4 . . 121.44(18) no
C3 C4 C5 . . 122.32(16) no
C4 C5 C7 . . 121.51(14) no
C6 C5 C7 . . 119.48(15) no
C4 C5 C6 . . 119.01(14) no
C1 C6 C5 . . 118.87(13) no
C1 C6 C10 . . 122.60(13) no
C5 C6 C10 . . 118.53(14) no
C5 C7 C8 . . 120.54(16) no
C7 C8 C9 . . 120.30(18) no
C8 C9 C10 . . 120.39(17) no
C6 C10 C9 . . 120.76(16) no
N2 C11 C12 . . 117.83(14) no
N2 C11 C16 . . 122.48(13) no
C12 C11 C16 . . 119.70(13) no
C11 C12 C13 . . 120.33(16) no
C12 C13 C14 . . 119.86(16) no
O2 C14 C13 . . 123.34(15) no
C13 C14 C15 . . 119.84(14) no
O2 C14 C15 . . 116.82(15) no
C14 C15 C16 . . 120.34(16) no
C11 C16 C15 . . 119.93(14) no
C4 C3 H3A . . 119.00 no
C2 C3 H3A . . 119.00 no
C3 C4 H4A . . 119.00 no
C5 C4 H4A . . 119.00 no
C5 C7 H7A . . 120.00 no
C8 C7 H7A . . 120.00 no
C9 C8 H8A . . 120.00 no
C7 C8 H8A . . 120.00 no
C8 C9 H9A . . 120.00 no
C10 C9 H9A . . 120.00 no
C6 C10 H10A . . 120.00 no
C9 C10 H10A . . 120.00 no
C11 C12 H12A . . 120.00 no
C13 C12 H12A . . 120.00 no
C12 C13 H13A . . 120.00 no
C14 C13 H13A . . 120.00 no
C16 C15 H15A . . 120.00 no
C14 C15 H15A . . 120.00 no
C11 C16 H16A . . 120.00 no
C15 C16 H16A . . 120.00 no
O1S C1S O1S . 2_554 64.2(2) no
O1S C1S H1SA . . 120(3) no
O1S C1S H1SB . . 95.7(18) no
O1S C1S H1SA . 2_554 121(3) no
O1S C1S H1SB . 2_554 31.5(18) no
H1SA C1S H1SB . . 106(3) no
O1S C1S H1SA 2_554 . 121(3) no
H1SA C1S H1SA . 2_554 107(4) no
H1SA C1S H1SB . 2_554 105(4) no
O1S C1S H1SB 2_554 . 31.5(18) no
H1SA C1S H1SB 2_554 . 105(4) no
H1SB C1S H1SB . 2_554 127(3) no
O1S C1S H1SA 2_554 2_554 120(3) no
O1S C1S H1SB 2_554 2_554 95.7(18) no
H1SA C1S H1SB 2_554 2_554 106(3) no
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
O1 C2 . 1.295(2) no
O2 C14 . 1.362(2) no
O2 H2B . 0.8200 no
O1S C1S . 1.347(3) no
O1S H1SB 2_554 0.76(3) no
O1S H1O . 0.9200 no
N1 N2 . 1.2848(19) no
N1 C1 . 1.3538(18) no
N2 C11 . 1.4027(18) no
N2 H2A . 0.8600 no
C1 C6 . 1.449(2) no
C1 C2 . 1.429(2) no
C2 C3 . 1.426(3) no
C3 C4 . 1.341(3) no
C4 C5 . 1.428(2) no
C5 C7 . 1.405(2) no
C5 C6 . 1.4093(19) no
C6 C10 . 1.402(2) no
C7 C8 . 1.362(3) no
C8 C9 . 1.390(3) no
C9 C10 . 1.370(3) no
C11 C16 . 1.384(2) no
C11 C12 . 1.385(2) no
C12 C13 . 1.380(3) no
C13 C14 . 1.376(2) no
C14 C15 . 1.389(2) no
C15 C16 . 1.372(2) no
C3 H3A . 0.9300 no
C4 H4A . 0.9300 no
C7 H7A . 0.9300 no
C8 H8A . 0.9300 no
C9 H9A . 0.9300 no
C10 H10A . 0.9300 no
C12 H12A . 0.9300 no
C13 H13A . 0.9300 no
C15 H15A . 0.9300 no
C16 H16A . 0.9300 no
C1S H1SA . 1.11(6) no
C1S H1SB . 0.87(3) no
C1S H1SA 2_554 1.11(6) no
C1S H1SB 2_554 0.87(3) no
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
_geom_hbond_publ_flag
O1S H1O O1 3_585 0.92 1.92 2.832(3) 171 yes
N2 H2A O1 . 0.86 1.84 2.540(2) 137 yes
O2 H2B O1S . 0.82 2.03 2.841(3) 172 yes
O2 H2B O1S 2_554 0.82 1.97 2.690(3) 146 yes
C1S H1SA Cg3 2_564 1.11(6) 2.58(5) 3.555(2) 147(4) yes
C7 H7A Cg2 6_545 0.93 2.73 3.521(2) 144 yes
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_publ_flag
C1 N1 N2 C11 -179.19(12) no
N2 N1 C1 C2 -0.5(2) no
N2 N1 C1 C6 178.51(12) no
N1 N2 C11 C12 -178.98(13) no
N1 N2 C11 C16 0.9(2) no
N1 C1 C2 O1 -1.3(2) no
N1 C1 C2 C3 177.00(14) no
C6 C1 C2 O1 179.78(14) no
C6 C1 C2 C3 -2.0(2) no
N1 C1 C6 C5 -176.08(12) no
N1 C1 C6 C10 3.72(19) no
C2 C1 C6 C5 2.97(19) no
C2 C1 C6 C10 -177.23(14) no
O1 C2 C3 C4 178.23(16) no
C1 C2 C3 C4 0.0(2) no
C2 C3 C4 C5 1.1(3) no
C3 C4 C5 C6 0.0(2) no
C3 C4 C5 C7 179.16(15) no
C4 C5 C6 C1 -1.97(19) no
C4 C5 C6 C10 178.22(13) no
C7 C5 C6 C1 178.85(13) no
C7 C5 C6 C10 -1.0(2) no
C4 C5 C7 C8 -178.29(15) no
C6 C5 C7 C8 0.9(2) no
C1 C6 C10 C9 -179.35(14) no
C5 C6 C10 C9 0.5(2) no
C5 C7 C8 C9 -0.2(2) no
C7 C8 C9 C10 -0.3(3) no
C8 C9 C10 C6 0.2(2) no
N2 C11 C12 C13 -179.50(14) no
C16 C11 C12 C13 0.7(2) no
N2 C11 C16 C15 179.40(13) no
C12 C11 C16 C15 -0.8(2) no
C11 C12 C13 C14 0.2(2) no
C12 C13 C14 O2 179.21(15) no
C12 C13 C14 C15 -0.9(2) no
O2 C14 C15 C16 -179.31(13) no
C13 C14 C15 C16 0.8(2) no
C14 C15 C16 C11 0.0(2) no
