#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/73/2007375.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_2007375
loop_
_publ_author_name
'Işik, Şamil'
'Aygün, Muhittin'
'Kocaokutgen, Hasan'
'Tahir, M. Nawaz'
'Büyükgüngör, Orhan'
'Erdönmez, Ahmet'
_publ_section_title
;
 3-tert-Butyl-2hydroxy-5-methoxyazobenzene
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              859
_journal_page_last               860
_journal_paper_doi               10.1107/S0108270198000286
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C17 H20 N2 O2'
_chemical_formula_sum            'C17 H20 N2 O2'
_chemical_formula_weight         284.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.984(2)
_cell_length_b                   6.8930(10)
_cell_length_c                   17.224(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.29
_cell_measurement_theta_min      8.64
_cell_volume                     1541.5(4)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'OrtepII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2321
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        1.2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      1.233
_exptl_crystal_density_method    pycnometry
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.159
_refine_ls_extinction_coef       0.0032(9)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   1.055
_refine_ls_goodness_of_fit_obs   1.219
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_restrained_S_obs      1.219
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_obs          .044
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.058P)²+0.081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.113
_refine_ls_wR_factor_obs         .1032
_reflns_number_observed          953
_reflns_number_total             1451
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sk1089.cif
_cod_data_source_block           hk1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.058P)^2^+0.081P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.058P)^2^+0.081P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2007375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 .41453(14) .2500 .36835(9) .0560(5) Uani d S 1 . O
H1 .348(2) .2500 .4005(16) .084 Uiso d S 1 . H
O2 .72672(13) .2500 .58460(10) .0660(6) Uani d S 1 . O
N1 .29274(15) .2500 .48332(11) .0467(5) Uani d S 1 . N
N2 .36590(15) .2500 .53261(11) .0429(5) Uani d S 1 . N
C1 .1920(2) .2500 .51518(15) .0483(6) Uani d S 1 . C
C2 .1710(2) .2500 .5939(2) .0652(8) Uani d S 1 . C
H2 .2245(2) .2500 .6298(2) .078 Uiso calc SR 1 . H
C3 .0701(2) .2500 .6186(2) .0836(10) Uani d S 1 . C
H3 .0557(2) .2500 .6715(2) .100 Uiso calc SR 1 . H
C4 -.0088(2) .2500 .5667(2) .0848(11) Uani d S 1 . C
H4 -.0766(2) .2500 .5840(2) .102 Uiso calc SR 1 . H
C5 .0120(2) .2500 .4893(3) .0896(11) Uani d S 1 . C
H5 -.0419(2) .2500 .4537(3) .108 Uiso calc SR 1 . H
C6 .1125(2) .2500 .4629(2) .0709(9) Uani d S 1 . C
H6 .1261(2) .2500 .4099(2) .085 Uiso calc SR 1 . H
C7 .4658(2) .2500 .50181(13) .0383(6) Uani d S 1 . C
C8 .5432(2) .2500 .55806(13) .0432(6) Uani d S 1 . C
H8 .5263(2) .2500 .61055(13) .052 Uiso calc SR 1 . H
C9 .6437(2) .2500 .53521(14) .0460(6) Uani d S 1 . C
C10 .6674(2) .2500 .45612(15) .0500(7) Uani d S 1 . C
H10 .7364(2) .2500 .44173(15) .060 Uiso calc SR 1 . H
C11 .5945(2) .2500 .39853(13) .0450(6) Uani d S 1 . C
C12 .4900(2) .2500 .42208(12) .0416(6) Uani d S 1 . C
C13 .6235(2) .2500 .31179(14) .0545(7) Uani d S 1 . C
C14 .5803(2) .0673(3) .27264(10) .0723(7) Uani d . 1 . C
H14A .5064(2) .0686(8) .2757(5) .096(8) Uiso calc R 1 . H
H14B .6063(7) -.0458(3) .2986(4) .089(7) Uiso calc R 1 . H
H14C .6011(7) .0648(9) .2192(2) .080(6) Uiso calc R 1 . H
C15 .7404(3) .2500 .3004(2) .0758(10) Uani d S 1 . C
H15A .754(2) .2500 .2452(18) .085(9) Uiso d S 1 . H
H15B .7721(16) .134(3) .3215(11) .085(7) Uiso d . 1 . H
C16 .7042(3) .2500 .6654(2) .0702(9) Uani d S 1 . C
H16A .773(2) .2500 .6916(15) .078(9) Uiso d S 1 . H
H16B .6637(17) .127(3) .6796(12) .096(7) 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'
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'
H H 0.0000 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
C12 O1 H1 . . 103.8(16) yes
C9 O2 C16 . . 116.4(2) ?
N2 N1 C1 . . 115.5(2) yes
N1 N2 C7 . . 116.0(2) yes
C6 C1 C2 . . 119.7(3) ?
C6 C1 N1 . . 116.2(2) yes
C2 C1 N1 . . 124.1(2) yes
C3 C2 C1 . . 119.3(3) ?
C3 C2 H2 . . 120.3(2) ?
C1 C2 H2 . . 120.3(2) ?
C4 C3 C2 . . 120.9(3) ?
C4 C3 H3 . . 119.5(2) ?
C2 C3 H3 . . 119.5(2) ?
C5 C4 C3 . . 119.6(3) ?
C5 C4 H4 . . 120.2(2) ?
C3 C4 H4 . . 120.2(2) ?
C4 C5 C6 . . 120.6(3) ?
C4 C5 H5 . . 119.7(2) ?
C6 C5 H5 . . 119.7(2) ?
C1 C6 C5 . . 119.7(3) ?
C1 C6 H6 . . 120.1(2) ?
C5 C6 H6 . . 120.1(2) ?
C8 C7 N2 . . 113.8(2) yes
C8 C7 C12 . . 121.0(2) ?
N2 C7 C12 . . 125.2(2) yes
C9 C8 C7 . . 119.3(2) ?
C9 C8 H8 . . 120.37(14) ?
C7 C8 H8 . . 120.37(13) ?
C8 C9 O2 . . 124.9(2) yes
C8 C9 C10 . . 119.5(2) ?
O2 C9 C10 . . 115.5(2) yes
C11 C10 C9 . . 123.6(2) ?
C11 C10 H10 . . 118.18(14) ?
C9 C10 H10 . . 118.18(15) ?
C10 C11 C12 . . 117.0(2) ?
C10 C11 C13 . . 122.3(2) ?
C12 C11 C13 . . 120.8(2) ?
O1 C12 C7 . . 120.4(2) yes
O1 C12 C11 . . 120.0(2) yes
C7 C12 C11 . . 119.6(2) ?
C15 C13 C14 . . 107.8(2) ?
C15 C13 C14 . 7_565 107.8(2) ?
C14 C13 C14 . 7_565 110.3(2) ?
C15 C13 C11 . . 111.5(2) ?
C14 C13 C11 . . 109.69(13) ?
C14 C13 C11 7_565 . 109.69(13) ?
C13 C14 H14A . . 109.47(13) ?
C13 C14 H14B . . 109.47(12) ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.47(11) ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 108.0(18) ?
C13 C15 H15B . . 111.8(12) ?
H15A C15 H15B . . 106.8(15) ?
O2 C16 H16A . . 105.0(15) ?
O2 C16 H16B . . 109.7(12) ?
H16A C16 H16B . . 110.5(14) ?
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 C12 . 1.348(3) yes
O1 H1 . 1.02(3) ?
O2 C9 . 1.374(3) yes
O2 C16 . 1.422(3) yes
N1 N2 . 1.274(3) yes
N1 C1 . 1.419(3) yes
N2 C7 . 1.401(3) yes
C1 C6 . 1.369(3) ?
C1 C2 . 1.383(3) ?
C2 C3 . 1.378(4) ?
C2 H2 . .93 ?
C3 C4 . 1.359(4) ?
C3 H3 . .93 ?
C4 C5 . 1.361(5) ?
C4 H4 . .93 ?
C5 C6 . 1.381(4) ?
C5 H5 . .93 ?
C6 H6 . .93 ?
C7 C8 . 1.396(3) ?
C7 C12 . 1.409(3) ?
C8 C9 . 1.363(3) ?
C8 H8 . .93 ?
C9 C10 . 1.397(3) ?
C10 C11 . 1.370(3) ?
C10 H10 . .93 ?
C11 C12 . 1.416(3) ?
C11 C13 . 1.541(3) yes
C13 C15 . 1.531(4) yes
C13 C14 . 1.535(2) yes
C13 C14 7_565 1.535(2) yes
C14 H14A . .96 ?
C14 H14B . .96 ?
C14 H14C . .96 ?
C15 H15A . .97(3) ?
C15 H15B . .97(2) ?
C16 H16A . 1.00(3) ?
C16 H16B . 1.03(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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C7 . 180.0 yes
N2 N1 C1 C6 . 180.0 ?
N2 N1 C1 C2 . 0.0 ?
C6 C1 C2 C3 . 0.0 ?
N1 C1 C2 C3 . 180.0 ?
C1 C2 C3 C4 . 0.0 ?
C2 C3 C4 C5 . 0.0 ?
C3 C4 C5 C6 . 0.0 ?
C2 C1 C6 C5 . 0.0 ?
N1 C1 C6 C5 . 180.0 ?
C4 C5 C6 C1 . 0.0 ?
N1 N2 C7 C8 . 180.0 ?
N1 N2 C7 C12 . 0.0 ?
N2 C7 C8 C9 . 180.0 ?
C12 C7 C8 C9 . 0.0 ?
C7 C8 C9 O2 . 180.0 ?
C7 C8 C9 C10 . 0.0 ?
C16 O2 C9 C8 . 0.0 ?
C16 O2 C9 C10 . 180.0 ?
C8 C9 C10 C11 . 0.0 ?
O2 C9 C10 C11 . 180.0 ?
C9 C10 C11 C12 . 0.0 ?
C9 C10 C11 C13 . 180.0 ?
C8 C7 C12 O1 . 180.0 ?
N2 C7 C12 O1 . 0.0 ?
C8 C7 C12 C11 . 0.0 ?
N2 C7 C12 C11 . 180.0 ?
C10 C11 C12 O1 . 180.0 ?
C13 C11 C12 O1 . 0.0 ?
C10 C11 C12 C7 . 0.0 ?
C13 C11 C12 C7 . 180.0 ?
C10 C11 C13 C15 . 0.0 ?
C12 C11 C13 C15 . 180.0 ?
C10 C11 C13 C14 . 119.4(2) yes
C12 C11 C13 C14 . -60.6(2) yes
C10 C11 C13 C14 7_565 -119.4(2) yes
C12 C11 C13 C14 7_565 60.6(2) yes
