#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/68/2206831.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_2206831
loop_
_publ_author_name
'Deveci, Özlem'
'Işık, Şamil'
'Albayrak, Çiǧdem'
'Ağar, Erbil'
_publ_section_title
;
 4-[2-Methyl-4-(4-methylphenyldiazenyl)phenoxy]phthalonitrile
;
_journal_coeditor_code           AC6181
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3327
_journal_page_last               o3329
_journal_paper_doi               10.1107/S1600536805029053
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C22 H16 N4 O'
_chemical_formula_moiety         'C22 H16 N4 O'
_chemical_formula_sum            'C22 H16 N4 O'
_chemical_formula_weight         352.39
_chemical_name_systematic
;
4-[2-Methyl-4-(4-methylphenyldiazenyl)phenoxy]phtalonitrile
;
_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                90.00
_cell_angle_beta                 119.050(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7084(10)
_cell_length_b                   8.0446(9)
_cell_length_c                   20.2971(16)
_cell_measurement_reflns_used    13869
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      1.83
_cell_volume                     1814.0(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         ' sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17432
_diffrn_reflns_theta_full        27.80
_diffrn_reflns_theta_max         27.80
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         17432
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism.
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.210
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0530
_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)+(0.0805P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1565
_reflns_number_gt                1998
_reflns_number_total             4285
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6181.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206831
_cod_database_fobs_code          2206831
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
C1 0.3345(2) 0.3867(3) 0.23129(13) 0.0569(6) Uani d . 1 C
C2 0.22959(19) 0.4437(3) 0.22799(12) 0.0507(5) Uani d . 1 C
C3 0.1716(2) 0.5822(3) 0.18615(13) 0.0553(6) Uani d . 1 C
C4 0.2187(2) 0.6653(3) 0.14674(13) 0.0567(6) Uani d . 1 C
C5 0.32372(19) 0.6113(3) 0.14962(12) 0.0545(4) Uani d . 1 C
C6 0.38272(19) 0.4719(3) 0.19314(11) 0.0521(5) Uani d . 1 C
C7 0.4958(2) 0.4225(3) 0.19989(14) 0.0678(7) Uani d . 1 C
C8 0.3745(2) 0.6987(3) 0.11033(12) 0.0545(4) Uani d . 1 C
C9 0.1391(2) 0.6045(3) 0.39910(15) 0.0614(3) Uani d . 1 C
C10 0.0191(2) 0.5799(3) 0.37385(13) 0.0614(3) Uani d . 1 C
C11 -0.0488(2) 0.4847(3) 0.31002(13) 0.0614(3) Uani d . 1 C
C12 0.0079(2) 0.4130(3) 0.27338(15) 0.0608(6) Uani d . 1 C
C13 0.1288(2) 0.4377(3) 0.30063(12) 0.0524(5) Uani d . 1 C
C14 0.1985(2) 0.5340(3) 0.36421(12) 0.0541(5) Uani d . 1 C
C15 0.3310(2) 0.5592(5) 0.39446(18) 0.0699(7) Uani d . 1 C
C16 -0.3294(2) 0.7384(4) 0.47598(15) 0.0701(7) Uani d . 1 C
C17 -0.2813(2) 0.6619(3) 0.43649(15) 0.0660(3) Uani d . 1 C
C18 -0.1680(2) 0.7045(3) 0.45024(14) 0.0660(3) Uani d . 1 C
C19 -0.1054(2) 0.8267(3) 0.50270(14) 0.0660(3) Uani d . 1 C
H19 -0.0292 0.8583 0.5117 0.079 Uiso calc R 1 H
C20 -0.1564(2) 0.9020(4) 0.54192(16) 0.0716(7) Uani d . 1 C
C21 -0.2688(2) 0.8579(3) 0.52950(14) 0.0608(6) Uani d . 1 C
C22 -0.3226(3) 0.9391(4) 0.57321(17) 0.0913(9) Uani d . 1 C
H22A -0.2717 0.9188 0.6261 0.137 Uiso calc R 1 H
H22B -0.4010 0.8934 0.5575 0.137 Uiso calc R 1 H
H22C -0.3292 1.0566 0.5639 0.137 Uiso calc R 1 H
N1 0.5869(2) 0.3875(4) 0.20607(14) 0.0996(9) Uani d . 1 N
N2 0.4172(2) 0.7694(3) 0.08035(13) 0.0838(7) Uani d . 1 N
N3 -0.02561(18) 0.6637(2) 0.41914(11) 0.0614(3) Uani d . 1 N
N4 -0.12549(18) 0.6172(3) 0.40522(11) 0.0660(3) Uani d . 1 N
O1 0.18625(14) 0.35213(18) 0.26680(9) 0.0622(4) Uani d . 1 O
H1 0.374(2) 0.291(3) 0.2605(14) 0.077(8) Uiso d . 1 H
H3 0.101(2) 0.615(3) 0.1860(13) 0.066(7) Uiso d . 1 H
H4 0.1753(19) 0.762(3) 0.1166(12) 0.062(6) Uiso d . 1 H
H9 0.183(2) 0.675(3) 0.4420(15) 0.087(8) Uiso d . 1 H
H11 -0.140(2) 0.467(3) 0.2877(13) 0.077(7) Uiso d . 1 H
H12 -0.034(2) 0.355(3) 0.2301(14) 0.068(7) Uiso d . 1 H
H15A 0.367(2) 0.606(3) 0.4437(16) 0.083(8) Uiso d . 1 H
H15B 0.367(3) 0.462(4) 0.3897(18) 0.114(12) Uiso d . 1 H
H15C 0.348(2) 0.640(4) 0.3650(15) 0.083(8) Uiso d . 1 H
H16 -0.410(3) 0.707(3) 0.4649(15) 0.092(9) Uiso d . 1 H
H17 -0.327(3) 0.567(4) 0.3954(17) 0.109(10) Uiso d . 1 H
H20 -0.120(3) 0.980(4) 0.5761(16) 0.089(10) Uiso d . 1 H
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
_geom_angle_publ_flag
C6 C1 C2 119.3(2) yes
C6 C1 H1 120.7(15) ?
C2 C1 H1 120.0(15) ?
O1 C2 C3 122.9(2) ?
O1 C2 C1 116.1(2) ?
C3 C2 C1 120.9(2) yes
C2 C3 C4 119.7(2) ?
C2 C3 H3 117.2(15) ?
C4 C3 H3 123.1(15) ?
C5 C4 C3 120.4(2) ?
C5 C4 H4 121.1(13) ?
C3 C4 H4 118.5(13) ?
C4 C5 C6 119.4(2) yes
C4 C5 C8 120.8(2) ?
C6 C5 C8 119.8(2) ?
C1 C6 C5 120.3(2) ?
C1 C6 C7 120.5(2) ?
C5 C6 C7 119.2(2) ?
N1 C7 C6 178.1(3) ?
N2 C8 C5 178.6(3) ?
C10 C9 C14 122.4(2) yes
C10 C9 H9 118.8(16) ?
C14 C9 H9 118.8(16) ?
C9 C10 C11 120.3(2) ?
C9 C10 N3 113.7(2) ?
C11 C10 N3 126.0(2) ?
C10 C11 C12 118.7(2) yes
C10 C11 H11 123.2(13) ?
C12 C11 H11 118.1(14) ?
C13 C12 C11 119.7(2) ?
C13 C12 H12 118.8(15) ?
C11 C12 H12 121.4(15) ?
C12 C13 C14 122.6(2) yes
C12 C13 O1 118.6(2) ?
C14 C13 O1 118.59(19) ?
C9 C14 C13 116.3(2) ?
C9 C14 C15 121.2(2) ?
C13 C14 C15 122.5(2) ?
C14 C15 H15A 110.7(16) ?
C14 C15 H15B 110(2) ?
H15A C15 H15B 116(3) ?
C14 C15 H15C 111.9(16) ?
H15A C15 H15C 104(2) ?
H15B C15 H15C 104(3) ?
C17 C16 C21 122.6(2) ?
C17 C16 H16 117.9(16) ?
C21 C16 H16 119.4(16) ?
C16 C17 C18 119.6(3) ?
C16 C17 H17 123.0(16) ?
C18 C17 H17 117.4(16) ?
C17 C18 C19 119.3(2) yes
C17 C18 N4 115.3(2) ?
C19 C18 N4 125.4(2) ?
C18 C19 C20 119.9(2) ?
C18 C19 H19 120.0 ?
C20 C19 H19 120.0 ?
C21 C20 C19 121.1(3) yes
C21 C20 H20 115.8(19) ?
C19 C20 H20 123.0(19) ?
C20 C21 C16 117.4(2) yes
C20 C21 C22 120.7(3) ?
C16 C21 C22 121.9(2) ?
C21 C22 H22A 109.5 ?
C21 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C21 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
N4 N3 C10 113.1(2) yes
N3 N4 C18 111.7(2) yes
C2 O1 C13 117.82(17) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.380(3) yes
C1 C2 1.380(3) yes
C1 H1 0.95(3) ?
C2 O1 1.374(3) ?
C2 C3 1.377(3) ?
C3 C4 1.382(3) yes
C3 H3 0.93(2) ?
C4 C5 1.378(3) ?
C4 H4 0.98(2) ?
C5 C6 1.399(3) yes
C5 C8 1.431(3) yes
C6 C7 1.432(3) yes
C7 N1 1.138(3) ?
C8 N2 1.144(3) ?
C9 C10 1.367(3) ?
C9 C14 1.383(3) yes
C9 H9 0.96(3) ?
C10 C11 1.387(3) yes
C10 N3 1.459(3) ?
C11 C12 1.388(3) yes
C11 H11 1.02(2) ?
C12 C13 1.371(3) ?
C12 H12 0.90(2) ?
C13 C14 1.393(3) yes
C13 O1 1.402(3) ?
C14 C15 1.500(3) ?
C15 H15A 0.95(3) ?
C15 H15B 0.94(4) ?
C15 H15C 0.97(3) ?
C16 C17 1.368(4) ?
C16 C21 1.373(4) ?
C16 H16 0.97(3) ?
C17 C18 1.370(3) ?
C17 H17 1.07(3) ?
C18 C19 1.382(4) yes
C18 N4 1.449(3) ?
C19 C20 1.386(4) yes
C19 H19 0.9300 ?
C20 C21 1.372(4) ?
C20 H20 0.88(3) ?
C21 C22 1.506(3) ?
C22 H22A 0.9600 ?
C22 H22B 0.9600 ?
C22 H22C 0.9600 ?
N3 N4 1.218(3) ?
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
C19 H19 N3 . 0.93 2.46 2.701(3) 95
C15 H15A N2 4_576 0.96(3) 2.71(3) 3.649(4) 166(2)
C17 H17 N2 2_545 1.07(3) 2.79(3) 3.534(4) 127(2)
C22 H22A O1 3_566 0.96 2.90 3.684(3) 140
C12 H12 Cg2 2_545 0.90(2) 3.03(2) 3.796(3) 144.2(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180322
