#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/95/2209533.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_2209533
loop_
_publ_author_name
Atalay,Şehriman
'Petek, Hande'
'Ocak Ískeleli, Nazan'
'Albayrak, Çiğdem'
'Ağar, Erbil'
_publ_section_title
;
 (E)-4-[(4-Chlorophenyl)diazenyl]-2-isopropylphenol
;
_journal_coeditor_code           HG2054
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3092
_journal_page_last               o3093
_journal_paper_doi               10.1107/S1600536806024408
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H15 Cl N2 O'
_chemical_formula_moiety         'C15 H15 Cl N2 O'
_chemical_formula_sum            'C15 H15 Cl N2 O'
_chemical_formula_weight         274.74
_chemical_name_systematic
;
(E)-4-[(4-Chlorophenyl)diazenyl]-2-isopropylphenol
;
_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                 91.585(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4856(5)
_cell_length_b                   11.1262(6)
_cell_length_c                   12.0768(5)
_cell_measurement_reflns_used    28365
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      1.94
_cell_volume                     1408.40(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS-II'
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19848
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9059
_exptl_absorpt_correction_T_min  0.8419
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.637
_exptl_crystal_size_min          0.510
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.333
_refine_ls_extinction_coef       0.071(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0412
_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)+(0.0683P)²+0.176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2455
_reflns_number_total             2762
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2054.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209533
_cod_database_fobs_code          2209533
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_occupancy
H H6 0.2347(17) 0.7464(16) 0.4732(15) 0.064(5) Uiso d 1
H H3 0.5500(16) 0.9049(15) 0.2665(15) 0.057(4) Uiso d 1
H H14 0.0271(18) 0.3487(18) -0.2116(17) 0.078(6) Uiso d 1
H H2B 0.484(2) 1.044(2) 0.1238(17) 0.084(6) Uiso d 1
H H9 0.3965(15) 0.6726(15) 0.1237(14) 0.058(4) Uiso d 1
H H1C 0.655(2) 0.879(2) 0.1013(19) 0.096(7) Uiso d 1
H H7 0.1672(17) 0.5767(15) 0.3727(14) 0.060(4) Uiso d 1
H H2A 0.371(2) 0.952(2) 0.087(2) 0.097(7) Uiso d 1
H H15 0.140(2) 0.5010(19) -0.1176(16) 0.079(6) Uiso d 1
H H12 0.0688(19) 0.1344(19) 0.0604(17) 0.078(6) Uiso d 1
H H1B 0.544(2) 0.795(2) 0.053(2) 0.098(7) Uiso d 1
H H11 0.1818(18) 0.2879(17) 0.1495(17) 0.072(5) Uiso d 1
H H1A 0.635(2) 0.746(3) 0.157(2) 0.100(8) Uiso d 1
H H2C 0.375(2) 1.018(2) 0.207(2) 0.097(7) Uiso d 1
H H1 0.352(2) 0.922(2) 0.4640(19) 0.085(6) Uiso d 1
Cl Cl1 -0.05269(5) 0.11757(4) -0.14832(4) 0.0815(2) Uani d 1
O O1 0.39874(12) 0.90860(10) 0.41089(9) 0.0614(3) Uani d 1
N N2 0.23314(11) 0.50803(10) 0.07837(9) 0.0495(3) Uani d 1
N N1 0.21547(11) 0.51304(11) 0.18066(9) 0.0504(3) Uani d 1
C C9 0.36370(13) 0.68802(13) 0.19424(11) 0.0476(3) Uani d 1
C C7 0.22621(15) 0.63320(14) 0.34187(12) 0.0526(3) Uani d 1
C C8 0.27153(13) 0.61174(12) 0.23668(11) 0.0466(3) Uani d 1
C C5 0.35605(13) 0.80956(13) 0.35630(11) 0.0484(3) Uani d 1
C C6 0.26741(15) 0.73222(14) 0.40071(11) 0.0540(4) Uani d 1
C C4 0.40717(12) 0.78721(12) 0.25185(10) 0.0466(3) Uani d 1
C C10 0.16971(13) 0.40833(12) 0.02605(11) 0.0493(3) Uani d 1
C C14 0.05854(16) 0.33525(15) -0.13611(14) 0.0602(4) Uani d 1
C C13 0.03752(14) 0.22888(14) -0.08216(13) 0.0575(4) Uani d 1
C C15 0.12646(16) 0.42496(15) -0.08207(12) 0.0574(4) Uani d 1
C C12 0.08494(18) 0.20888(16) 0.02394(15) 0.0668(4) Uani d 1
C C11 0.15018(17) 0.29976(15) 0.07856(13) 0.0617(4) Uani d 1
C C3 0.50135(15) 0.87509(15) 0.20465(13) 0.0571(4) Uani d 1
C C2 0.4300(2) 0.98012(18) 0.15176(18) 0.0759(5) Uani d 1
C C1 0.5913(2) 0.8181(2) 0.1231(2) 0.0843(6) 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 0.0016 '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'
Cl Cl 0.1484 0.1585 '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
C5 O1 H1 109.2(16)
N1 N2 C10 112.91(11)
N2 N1 C8 115.84(11)
C4 C9 C8 121.72(12)
C4 C9 H9 118.6(10)
C8 C9 H9 119.7(10)
C6 C7 C8 120.00(13)
C6 C7 H7 121.3(10)
C8 C7 H7 118.7(10)
C7 C8 C9 119.32(13)
C7 C8 N1 115.09(12)
C9 C8 N1 125.58(12)
O1 C5 C6 122.23(12)
O1 C5 C4 116.85(12)
C6 C5 C4 120.92(13)
C7 C6 C5 120.16(12)
C7 C6 H6 119.2(11)
C5 C6 H6 120.7(11)
C9 C4 C5 117.80(12)
C9 C4 C3 122.60(12)
C5 C4 C3 119.52(12)
C11 C10 C15 120.08(14)
C11 C10 N2 123.21(13)
C15 C10 N2 116.71(12)
C13 C14 C15 119.15(15)
C13 C14 H14 121.5(12)
C15 C14 H14 119.3(12)
C14 C13 C12 121.45(15)
C14 C13 Cl1 119.25(12)
C12 C13 Cl1 119.30(13)
C14 C15 C10 120.09(15)
C14 C15 H15 120.5(12)
C10 C15 H15 119.4(12)
C11 C12 C13 119.17(16)
C11 C12 H12 120.5(12)
C13 C12 H12 120.3(12)
C12 C11 C10 119.96(15)
C12 C11 H11 120.1(12)
C10 C11 H11 119.9(12)
C4 C3 C2 109.66(14)
C4 C3 C1 113.45(15)
C2 C3 C1 110.83(17)
C4 C3 H3 105.7(10)
C2 C3 H3 108.0(10)
C1 C3 H3 109.0(10)
C3 C2 H2B 114.6(13)
C3 C2 H2A 111.1(13)
H2B C2 H2A 107.7(18)
C3 C2 H2C 109.5(14)
H2B C2 H2C 106.1(18)
H2A C2 H2C 107(2)
C3 C1 H1C 108.9(13)
C3 C1 H1B 110.6(14)
H1C C1 H1B 105.7(19)
C3 C1 H1A 110.4(14)
H1C C1 H1A 110.5(19)
H1B C1 H1A 111(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C13 1.7392(15) y
O1 C5 1.3539(17) y
O1 H1 0.84(2) ?
N2 N1 1.2554(16) y
N2 C10 1.4314(18) y
N1 C8 1.4096(17) y
C9 C4 1.3756(19) ?
C9 C8 1.3944(19) ?
C9 H9 0.944(17) ?
C7 C6 1.374(2) ?
C7 C8 1.3893(19) ?
C7 H7 0.965(18) ?
C5 C6 1.385(2) ?
C5 C4 1.4063(18) ?
C6 H6 0.962(18) ?
C4 C3 1.5124(19) y
C10 C11 1.382(2) ?
C10 C15 1.383(2) ?
C14 C13 1.372(2) ?
C14 C15 1.380(2) ?
C14 H14 0.97(2) ?
C13 C12 1.380(2) ?
C15 H15 0.96(2) ?
C12 C11 1.379(2) ?
C12 H12 0.96(2) ?
C11 H11 0.92(2) ?
C3 C2 1.519(3) ?
C3 C1 1.521(3) ?
C3 H3 0.952(18) ?
C2 H2B 0.98(2) ?
C2 H2A 1.03(3) ?
C2 H2C 0.99(2) ?
C1 H1C 0.99(3) ?
C1 H1B 1.00(2) ?
C1 H1A 1.00(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
O1 H1 N2 4_576 0.84(2) 2.04(2) 2.8566(16) 168(2)
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
C10 N2 N1 C8 -177.76(11) y
C6 C7 C8 C9 3.3(2) ?
C6 C7 C8 N1 -175.29(13) ?
C4 C9 C8 C7 -2.8(2) ?
C4 C9 C8 N1 175.57(13) ?
N2 N1 C8 C7 164.67(13) ?
N2 N1 C8 C9 -13.8(2) y
C8 C7 C6 C5 -1.3(2) ?
O1 C5 C6 C7 179.54(14) ?
C4 C5 C6 C7 -1.3(2) ?
C8 C9 C4 C5 0.4(2) ?
C8 C9 C4 C3 -176.37(13) ?
O1 C5 C4 C9 -179.05(12) ?
C6 C5 C4 C9 1.7(2) ?
O1 C5 C4 C3 -2.2(2) y
C6 C5 C4 C3 178.53(14) ?
N1 N2 C10 C11 -31.99(19) ?
N1 N2 C10 C15 147.60(13) ?
C15 C14 C13 C12 -1.3(2) ?
C15 C14 C13 Cl1 177.82(12) y
C13 C14 C15 C10 -1.6(2) ?
C11 C10 C15 C14 3.0(2) ?
N2 C10 C15 C14 -176.60(14) ?
C14 C13 C12 C11 2.8(3) ?
Cl1 C13 C12 C11 -176.32(13) ?
C13 C12 C11 C10 -1.4(3) ?
C15 C10 C11 C12 -1.5(2) ?
N2 C10 C11 C12 178.09(15) ?
C9 C4 C3 C2 95.11(18) ?
C5 C4 C3 C2 -81.56(17) ?
C9 C4 C3 C1 -29.4(2) ?
C5 C4 C3 C1 153.93(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179124
