#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225278.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_2225278
loop_
_publ_author_name
'Basu Baul, Tushar S.'
'Paul, Anup'
'Tiekink, Edward R. T.'
_publ_section_title
;
 4-[(E)-(5-tert-Butyl-2-hydroxyphenyl)diazenyl]benzoic
 acid benzene hemisolvate
;
_journal_coeditor_code           HG2642
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o540
_journal_paper_doi               10.1107/S1600536810003880
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H18 N2 O3, 0.5C6 H6'
_chemical_formula_moiety         'C17 H18 N2 O3, 0.5(C6 H6)'
_chemical_formula_sum            'C20 H21 N2 O3'
_chemical_formula_weight         337.39
_chemical_name_systematic
;
4-[(E)-(5-tert-Butyl-2-hydroxyphenyl)diazenyl]benzoic acid
benzene hemisolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.326(2)
_cell_angle_beta                 88.992(2)
_cell_angle_gamma                71.355(2)
_cell_formula_units_Z            2
_cell_length_a                   6.0960(2)
_cell_length_b                   7.3578(3)
_cell_length_c                   20.6562(7)
_cell_measurement_reflns_used    2230
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      3.0
_cell_volume                     867.37(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11445
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.0
_diffrn_standards_decay_%        <1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.101
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0815P)²+0.0458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.113
_refine_ls_wR_factor_ref         0.157
_reflns_number_gt                1888
_reflns_number_total             3053
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2642.cif
_cod_data_source_block           I
_cod_original_cell_volume        867.37(5)
_cod_database_code               2225278
_cod_database_fobs_code          2225278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.9406(3) 0.7864(2) 0.00097(8) 0.0270(5) Uani d . 1 . .
O O2 0.7757(3) 1.0387(2) 0.05359(8) 0.0270(5) Uani d . 1 . .
H H2O 0.8709 1.0827 0.0321 0.040 Uiso calc R 1 . .
O O3 0.0159(3) 0.2070(2) 0.17405(9) 0.0295(5) Uani d . 1 . .
H H3O 0.1019 0.2690 0.1569 0.044 Uiso calc R 1 . .
N N1 0.1696(3) 0.4998(3) 0.15671(9) 0.0214(5) Uani d . 1 . .
N N2 0.0282(3) 0.5895(3) 0.19601(9) 0.0214(5) Uani d . 1 . .
C C1 0.7939(4) 0.8718(4) 0.03965(11) 0.0200(6) Uani d . 1 . .
C C2 0.6296(4) 0.7767(3) 0.07027(11) 0.0186(6) Uani d . 1 . .
C C3 0.6505(4) 0.5880(4) 0.06190(11) 0.0215(6) Uani d . 1 . .
H H3 0.7704 0.5196 0.0362 0.026 Uiso calc R 1 . .
C C4 0.4971(4) 0.5002(4) 0.09100(11) 0.0224(6) Uani d . 1 . .
H H4 0.5120 0.3709 0.0856 0.027 Uiso calc R 1 . .
C C5 0.3208(4) 0.6011(4) 0.12827(11) 0.0187(6) Uani d . 1 . .
C C6 0.2955(4) 0.7910(4) 0.13581(11) 0.0210(6) Uani d . 1 . .
H H6 0.1722 0.8610 0.1602 0.025 Uiso calc R 1 . .
C C7 0.4513(4) 0.8766(4) 0.10745(11) 0.0224(6) Uani d . 1 . .
H H7 0.4371 1.0055 0.1133 0.027 Uiso calc R 1 . .
C C8 -0.1216(4) 0.4932(4) 0.22568(11) 0.0193(6) Uani d . 1 . .
C C9 -0.1262(4) 0.3104(4) 0.21544(12) 0.0215(6) Uani d . 1 . .
C C10 -0.2869(4) 0.2363(4) 0.24863(12) 0.0254(6) Uani d . 1 . .
H H10 -0.2942 0.1134 0.2419 0.030 Uiso calc R 1 . .
C C11 -0.4361(4) 0.3394(4) 0.29125(12) 0.0245(6) Uani d . 1 . .
H H11 -0.5437 0.2849 0.3134 0.029 Uiso calc R 1 . .
C C12 -0.4341(4) 0.5213(4) 0.30302(11) 0.0201(6) Uani d . 1 . .
C C13 -0.2753(4) 0.5933(4) 0.26916(12) 0.0213(6) Uani d . 1 . .
H H13 -0.2699 0.7169 0.2757 0.026 Uiso calc R 1 . .
C C14 -0.5974(4) 0.6396(4) 0.35012(12) 0.0241(6) Uani d . 1 . .
C C15 -0.7522(5) 0.5308(4) 0.38459(13) 0.0357(8) Uani d . 1 . .
H H15A -0.8514 0.5080 0.3520 0.053 Uiso calc R 1 . .
H H15B -0.8489 0.6083 0.4154 0.053 Uiso calc R 1 . .
H H15C -0.6557 0.4060 0.4085 0.053 Uiso calc R 1 . .
C C16 -0.4527(5) 0.6816(4) 0.40241(13) 0.0344(7) Uani d . 1 . .
H H16A -0.3585 0.5590 0.4281 0.052 Uiso calc R 1 . .
H H16B -0.5559 0.7619 0.4314 0.052 Uiso calc R 1 . .
H H16C -0.3511 0.7508 0.3811 0.052 Uiso calc R 1 . .
C C17 -0.7517(5) 0.8319(4) 0.31170(13) 0.0307(7) Uani d . 1 . .
H H17A -0.6543 0.9044 0.2899 0.046 Uiso calc R 1 . .
H H17B -0.8531 0.9088 0.3419 0.046 Uiso calc R 1 . .
H H17C -0.8462 0.8052 0.2787 0.046 Uiso calc R 1 . .
C C18 0.8298(5) 0.0370(4) 0.45204(13) 0.0313(7) Uani d . 1 . .
H H18 0.7123 0.0620 0.4192 0.038 Uiso calc R 1 . .
C C19 0.9784(5) 0.1460(4) 0.44705(13) 0.0305(7) Uani d . 1 . .
H H19 0.9640 0.2458 0.4108 0.037 Uiso calc R 1 . .
C C20 1.1478(5) 0.1084(4) 0.49518(13) 0.0334(7) Uani d . 1 . .
H H20 1.2501 0.1831 0.4920 0.040 Uiso calc R 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'
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
C1 O2 H2O . . 109.5 ?
C9 O3 H3O . . 109.5 ?
N2 N1 C5 . . 114.0(2) ?
N1 N2 C8 . . 115.6(2) ?
O1 C1 O2 . . 123.8(2) ?
O1 C1 C2 . . 119.2(2) ?
O2 C1 C2 . . 117.0(2) ?
C3 C2 C7 . . 119.5(2) ?
C3 C2 C1 . . 120.4(2) ?
C7 C2 C1 . . 120.1(2) ?
C4 C3 C2 . . 120.0(2) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 119.9(2) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 120.5(2) ?
C6 C5 N1 . . 123.0(2) ?
C4 C5 N1 . . 116.4(2) ?
C7 C6 C5 . . 119.2(2) ?
C7 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
C6 C7 C2 . . 120.8(2) ?
C6 C7 H7 . . 119.6 ?
C2 C7 H7 . . 119.6 ?
C13 C8 C9 . . 119.4(2) ?
C13 C8 N2 . . 114.9(2) ?
C9 C8 N2 . . 125.7(2) ?
O3 C9 C10 . . 119.3(2) ?
O3 C9 C8 . . 122.4(2) ?
C10 C9 C8 . . 118.3(2) ?
C11 C10 C9 . . 120.7(2) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 122.3(2) ?
C10 C11 H11 . . 118.8 ?
C12 C11 H11 . . 118.8 ?
C13 C12 C11 . . 116.1(2) ?
C13 C12 C14 . . 120.3(2) ?
C11 C12 C14 . . 123.6(2) ?
C12 C13 C8 . . 123.2(2) ?
C12 C13 H13 . . 118.4 ?
C8 C13 H13 . . 118.4 ?
C15 C14 C16 . . 108.3(2) ?
C15 C14 C17 . . 108.6(2) ?
C16 C14 C17 . . 109.4(2) ?
C15 C14 C12 . . 111.9(2) ?
C16 C14 C12 . . 109.1(2) ?
C17 C14 C12 . . 109.44(19) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C20 C18 C19 2_756 . 120.0(3) ?
C20 C18 H18 2_756 . 120.0 ?
C19 C18 H18 . . 120.0 ?
C20 C19 C18 . . 119.3(3) ?
C20 C19 H19 . . 120.3 ?
C18 C19 H19 . . 120.3 ?
C19 C20 C18 . 2_756 120.7(3) ?
C19 C20 H20 . . 119.7 ?
C18 C20 H20 2_756 . 119.7 ?
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 C1 . 1.265(3) ?
O2 C1 . 1.274(3) ?
O2 H2O . 0.8400 ?
O3 C9 . 1.345(3) ?
O3 H3O . 0.8400 ?
N1 N2 . 1.269(3) ?
N1 C5 . 1.427(3) ?
N2 C8 . 1.406(3) ?
C1 C2 . 1.478(3) ?
C2 C3 . 1.390(3) ?
C2 C7 . 1.393(3) ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.390(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.389(3) ?
C6 C7 . 1.376(3) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C13 . 1.398(3) ?
C8 C9 . 1.401(3) ?
C9 C10 . 1.390(3) ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.400(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.379(3) ?
C12 C14 . 1.537(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.526(3) ?
C14 C16 . 1.533(4) ?
C14 C17 . 1.534(4) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C20 2_756 1.383(4) ?
C18 C19 . 1.383(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.379(4) ?
C19 H19 . 0.9500 ?
C20 C18 2_756 1.383(4) ?
C20 H20 . 0.9500 ?
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
O3 H3o N1 1_555 0.84 1.87 2.587(3) 142
O2 H2o O1 2_775 0.84 1.79 2.614(3) 167
C3 H3 O1 2_765 0.95 2.59 3.473(3) 155
C6 H6 O3 1_565 0.95 2.48 3.201(3) 133
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 C8 . . . . -179.2(2) ?
O1 C1 C2 C3 . . . . 6.4(4) ?
O2 C1 C2 C3 . . . . -174.6(2) ?
O1 C1 C2 C7 . . . . -173.2(2) ?
O2 C1 C2 C7 . . . . 5.8(4) ?
C7 C2 C3 C4 . . . . -0.8(4) ?
C1 C2 C3 C4 . . . . 179.6(2) ?
C2 C3 C4 C5 . . . . 0.5(4) ?
C3 C4 C5 C6 . . . . 0.9(4) ?
C3 C4 C5 N1 . . . . -180.0(2) ?
N2 N1 C5 C6 . . . . -8.3(3) ?
N2 N1 C5 C4 . . . . 172.6(2) ?
C4 C5 C6 C7 . . . . -1.8(4) ?
N1 C5 C6 C7 . . . . 179.1(2) ?
C5 C6 C7 C2 . . . . 1.5(4) ?
C3 C2 C7 C6 . . . . -0.2(4) ?
C1 C2 C7 C6 . . . . 179.4(2) ?
N1 N2 C8 C13 . . . . 179.6(2) ?
N1 N2 C8 C9 . . . . 0.1(4) ?
C13 C8 C9 O3 . . . . 179.6(2) ?
N2 C8 C9 O3 . . . . -0.9(4) ?
C13 C8 C9 C10 . . . . 0.8(4) ?
N2 C8 C9 C10 . . . . -179.7(2) ?
O3 C9 C10 C11 . . . . -179.7(2) ?
C8 C9 C10 C11 . . . . -0.8(4) ?
C9 C10 C11 C12 . . . . 0.2(4) ?
C10 C11 C12 C13 . . . . 0.5(4) ?
C10 C11 C12 C14 . . . . -179.9(2) ?
C11 C12 C13 C8 . . . . -0.5(4) ?
C14 C12 C13 C8 . . . . 179.9(2) ?
C9 C8 C13 C12 . . . . -0.1(4) ?
N2 C8 C13 C12 . . . . -179.7(2) ?
C13 C12 C14 C15 . . . . -177.7(2) ?
C11 C12 C14 C15 . . . . 2.7(4) ?
C13 C12 C14 C16 . . . . -57.8(3) ?
C11 C12 C14 C16 . . . . 122.6(3) ?
C13 C12 C14 C17 . . . . 61.9(3) ?
C11 C12 C14 C17 . . . . -117.7(3) ?
C20 C18 C19 C20 2_756 . . . -0.2(4) ?
C18 C19 C20 C18 . . . 2_756 0.2(4) ?
