#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/27/2222740.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_2222740
loop_
_publ_author_name
'Yu, Yan-Hong'
'Qian, Kun'
_publ_section_title
;
 1-(4-Cyanophenyldiazen-2-ium-1-yl)-2-naphtholate
;
_journal_coeditor_code           HK2742
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2033
_journal_paper_doi               10.1107/S1600536809028438
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H11 N3 O'
_chemical_formula_moiety         'C17 H11 N3 O'
_chemical_formula_sum            'C17 H11 N3 O'
_chemical_formula_weight         273.29
_chemical_name_systematic
;
1-(4-Cyanophenyldiazen-2-ium-1-yl)-2-naphtholate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.13(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2673(11)
_cell_length_b                   9.910(2)
_cell_length_c                   25.239(6)
_cell_measurement_reflns_used    1658
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.87
_cell_measurement_theta_min      3.18
_cell_volume                     1309.9(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω
_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  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13086
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3500
_exptl_crystal_size_mid          0.1000
_exptl_crystal_size_min          0.1000
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0541
_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)+(0.0717P)²+0.0861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                1941
_reflns_number_total             2998
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2742.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222740
_cod_database_fobs_code          2222740
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2630(3) -0.03169(14) 0.45197(5) 0.0627(4) Uani d . 1 . .
N N1 0.3499(3) 0.15188(14) 0.36889(6) 0.0424(4) Uani d . 1 . .
N N2 0.5123(3) 0.16008(14) 0.41170(5) 0.0444(4) Uani d . 1 . .
H H2A 0.4994 0.1072 0.4383 0.053 Uiso d R 1 . .
N N3 1.4464(4) 0.62761(18) 0.42541(8) 0.0731(5) Uani d . 1 . .
C C1 0.1628(3) 0.06230(17) 0.36607(7) 0.0427(4) Uani d . 1 . .
C C2 0.1200(4) -0.03101(18) 0.40895(7) 0.0503(5) Uani d . 1 . .
C C3 -0.0963(4) -0.12070(19) 0.39970(8) 0.0576(5) Uani d . 1 . .
H H3A -0.1284 -0.1821 0.4261 0.069 Uiso calc R 1 . .
C C4 -0.2519(4) -0.11777(18) 0.35418(8) 0.0542(5) Uani d . 1 . .
H H4A -0.3884 -0.1777 0.3501 0.065 Uiso calc R 1 . .
C C5 -0.2179(3) -0.02633(17) 0.31131(7) 0.0456(4) Uani d . 1 . .
C C6 -0.3895(3) -0.02176(19) 0.26515(7) 0.0534(5) Uani d . 1 . .
H H6A -0.5266 -0.0814 0.2614 0.064 Uiso calc R 1 . .
C C7 -0.3597(4) 0.0688(2) 0.22535(7) 0.0554(5) Uani d . 1 . .
H H7A -0.4760 0.0711 0.1949 0.066 Uiso calc R 1 . .
C C8 -0.1543(4) 0.15722(19) 0.23078(7) 0.0514(5) Uani d . 1 . .
H H8A -0.1329 0.2185 0.2037 0.062 Uiso calc R 1 . .
C C9 0.0175(3) 0.15515(18) 0.27562(7) 0.0474(4) Uani d . 1 . .
H H9A 0.1544 0.2149 0.2786 0.057 Uiso calc R 1 . .
C C10 -0.0106(3) 0.06409(16) 0.31707(6) 0.0410(4) Uani d . 1 . .
C C11 0.7076(3) 0.25635(16) 0.41359(6) 0.0398(4) Uani d . 1 . .
C C12 0.8755(3) 0.26618(19) 0.45927(7) 0.0505(5) Uani d . 1 . .
H H12A 0.8579 0.2089 0.4878 0.061 Uiso calc R 1 . .
C C13 1.0691(4) 0.36029(19) 0.46282(7) 0.0514(5) Uani d . 1 . .
H H13A 1.1819 0.3666 0.4937 0.062 Uiso calc R 1 . .
C C14 1.0948(3) 0.44545(17) 0.42018(7) 0.0446(4) Uani d . 1 . .
C C15 0.9273(3) 0.43388(19) 0.37409(7) 0.0509(5) Uani d . 1 . .
H H15A 0.9456 0.4904 0.3453 0.061 Uiso calc R 1 . .
C C16 0.7350(3) 0.33980(18) 0.37050(7) 0.0477(4) Uani d . 1 . .
H H16A 0.6240 0.3321 0.3394 0.057 Uiso calc R 1 . .
C C17 1.2921(4) 0.5465(2) 0.42332(7) 0.0533(5) Uani d . 1 . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N2 N1 C1 . . 120.28(14) ?
N1 N2 C11 . . 118.95(14) ?
N1 N2 H2A . . 120.5 ?
C11 N2 H2A . . 120.5 ?
N1 C1 C10 . . 115.69(15) ?
N1 C1 C2 . . 123.97(16) ?
C10 C1 C2 . . 120.31(15) ?
O1 C2 C3 . . 121.83(17) ?
O1 C2 C1 . . 121.30(16) ?
C3 C2 C1 . . 116.86(17) ?
C4 C3 C2 . . 121.70(18) ?
C4 C3 H3A . . 119.1 ?
C2 C3 H3A . . 119.1 ?
C3 C4 C5 . . 123.09(17) ?
C3 C4 H4A . . 118.5 ?
C5 C4 H4A . . 118.5 ?
C6 C5 C10 . . 119.42(16) ?
C6 C5 C4 . . 121.78(16) ?
C10 C5 C4 . . 118.76(16) ?
C7 C6 C5 . . 121.22(17) ?
C7 C6 H6A . . 119.4 ?
C5 C6 H6A . . 119.4 ?
C6 C7 C8 . . 119.42(18) ?
C6 C7 H7A . . 120.3 ?
C8 C7 H7A . . 120.3 ?
C9 C8 C7 . . 120.72(18) ?
C9 C8 H8A . . 119.6 ?
C7 C8 H8A . . 119.6 ?
C8 C9 C10 . . 120.83(17) ?
C8 C9 H9A . . 119.6 ?
C10 C9 H9A . . 119.6 ?
C9 C10 C5 . . 118.39(16) ?
C9 C10 C1 . . 122.33(15) ?
C5 C10 C1 . . 119.27(15) ?
C12 C11 C16 . . 120.16(16) ?
C12 C11 N2 . . 118.66(15) ?
C16 C11 N2 . . 121.18(16) ?
C13 C12 C11 . . 120.41(16) ?
C13 C12 H12A . . 119.8 ?
C11 C12 H12A . . 119.8 ?
C12 C13 C14 . . 119.67(17) ?
C12 C13 H13A . . 120.2 ?
C14 C13 H13A . . 120.2 ?
C13 C14 C15 . . 119.65(16) ?
C13 C14 C17 . . 120.72(17) ?
C15 C14 C17 . . 119.63(16) ?
C16 C15 C14 . . 120.67(16) ?
C16 C15 H15A . . 119.7 ?
C14 C15 H15A . . 119.7 ?
C15 C16 C11 . . 119.44(16) ?
C15 C16 H16A . . 120.3 ?
C11 C16 H16A . . 120.3 ?
N3 C17 C14 . . 179.1(2) ?
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 . 1.254(2) ?
N1 N2 . 1.3072(19) ?
N1 C1 . 1.323(2) ?
N2 C11 . 1.400(2) ?
N2 H2A . 0.8600 ?
N3 C17 . 1.141(2) ?
C1 C10 . 1.457(2) ?
C1 C2 . 1.459(2) ?
C2 C3 . 1.444(3) ?
C3 C4 . 1.338(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.437(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.397(2) ?
C5 C10 . 1.408(2) ?
C6 C7 . 1.369(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.387(3) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.372(2) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.401(2) ?
C9 H9A . 0.9300 ?
C11 C12 . 1.380(2) ?
C11 C16 . 1.386(2) ?
C12 C13 . 1.378(2) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.386(2) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.387(2) ?
C14 C17 . 1.439(3) ?
C15 C16 . 1.373(2) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
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
N2 H2A O1 . 0.86 1.91 2.580(2) 133 yes
C12 H12A O1 3_656 0.93 2.45 3.362(2) 166 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7877269
