#------------------------------------------------------------------------------
#$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $
#$Revision: 134621 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/35/2003545.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_2003545
loop_
_publ_author_name
'Chebli, C.'
'Brisse, F.'
_publ_section_title
;
 4,4'-Azoxydianisole at 203 K
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1164
_journal_page_last               1167
_journal_paper_doi               10.1107/S0108270194012023
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C14 H14 N2 O3'
_chemical_formula_sum            'C14 H14 N2 O3'
_chemical_formula_weight         258.28
_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_type_scat_source
;Cromer & Mann (1968) for C, N, O and Stewart, Davidson & Simpson
for H atoms
;
_cell_angle_alpha                90.
_cell_angle_beta                 113.28(12)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   10.9822(22)
_cell_length_b                   8.0799(16)
_cell_length_c                   15.449(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    203
_cell_measurement_theta_max      24
_cell_measurement_theta_min      20
_cell_volume                     1259.3(12)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9667
_diffrn_reflns_theta_max         70.0
_diffrn_standards_decay_%        <=1.2
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.71
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      1.291
_exptl_crystal_description       platelet
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.68
_refine_ls_number_parameters     301
_refine_ls_number_reflns         1941
_refine_ls_R_factor_obs          0.052
_refine_ls_shift/esd_max         0.06
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(F) + 0.0001F^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.059
_reflns_number_observed          1941
_reflns_number_total             2384
_reflns_observed_criterion       I>=2.0\s(I)
_[local]_cod_data_source_file    fg1010.cif
_[local]_cod_data_source_block   fg1010a
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F) + 0.0001F^2^]'
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^(F) +
0.0001F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1259.3(4)
_cod_database_code               2003545
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,1/2-y,1/2+z
-x,-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
C(1) .4867(3) -.0489(3) .7657(2) 5.6(1)
O(2) .4639(2) .0860(2) .8165(1) 5.2(1)
C(3) .5457(4) .1102(5) .9063(3) 4.3(1)
C(4) .6556(4) .0157(5) .9586(3) 4.9(1)
C(5) .7323(3) .0579(4) 1.0519(2) 4.2(1)
C(6) .6988(3) .1944(4) 1.0923(2) 3.7(1)
C(7) .5893(3) .2872(4) 1.0403(2) 4.7(1)
C(8) .5133(3) .2456(4) .9478(2) 4.8(1)
N(9) .7756(3) .2377(3) 1.1895(2) 4.1(1)
N(10) .8791(3) .1501(3) 1.2332(2) 4.2(1)
O(11) .7371(2) .3595(2) 1.2261(1) 6.0(1)
C(12) .9550(3) .1779(4) 1.3312(2) 3.7(1)
C(13) 1.0777(3) .0958(4) 1.3643(2) 4.5(1)
C(14) 1.1575(3) .0988(4) 1.4591(2) 4.7(1)
C(15) 1.1182(4) .1774(5) 1.5229(3) 4.6(1)
C(16) .9962(4) .2584(4) 1.4893(3) 5.0(1)
C(17) .9156(3) .2594(4) 1.3942(2) 4.3(1)
O(18) 1.2049(1) .1671(2) 1.6149(1) 5.2(1)
C(19) 1.1697(2) .2396(3) 1.6861(2) 5.6(1)
C(3') .5570(6) .1101(8) .9080(5) 4.0(2)
C(4') .6583(7) -.0053(8) .9480(5) 4.0(2)
C(5') .7461(7) .0111(8) 1.0419(5) 4.6(2)
C(6') .7327(7) .1430(8) 1.0958(5) 2.8(2)
C(7') .6314(7) .2584(8) 1.0557(5) 4.4(2)
C(8') .5435(7) .2420(8) .9619(5) 5.3(2)
N(9') .8302(8) .1384(9) 1.1887(6) 4.4(2)
N(10') .8293(8) .2438(9) 1.2496(6) 4.4(2)
C(12') .9263(6) .2223(7) 1.3427(4) 2.8(2)
C(13') 1.0399(6) .1278(7) 1.3601(4) 3.4(2)
C(14') 1.1334(6) .1086(7) 1.4521(4) 5.4(2)
C(15') 1.1134(6) .1839(7) 1.5267(4) 3.2(2)
C(16') .9999(6) .2785(7) 1.5092(4) 3.6(2)
C(17') .9063(6) .2976(7) 1.4172(4) 3.8(2)
H(1A)* .4204 -.0489 .7034 5.8(2)
H(1B)* .4834 -.1499 .7963 9.3(2)
H(1C)* .5715 -.0373 .7635 6.9(2)
H(4) .6787 -.0779 .9311 7.1(2)
H(5) .8076 -.0068 1.0880 8.3(2)
H(7) .5658 .3804 1.0680 6.8(2)
H(8) .4377 .3101 .9122 7.5(2)
H(13) 1.1057 .0382 1.3218 5.6(2)
H(14) 1.2415 .0458 1.4812 7.4(2)
H(16) .9678 .3145 1.5321 6.5(2)
H(17) .8330 .3158 1.3719 5.4(2)
H(19A)* 1.2392 .2225 1.7461 6.2(2)
H(19B)* 1.0907 .1897 1.6849 5.7(2)
H(19C)* 1.1556 .3550 1.6747 10.2(2)
H(4') .6675 -.0951 .9114 7.5(2)
H(5') .8151 -.0675 1.0692 6.3(2)
H(7') .6222 .3482 1.0924 6.0(2)
H(8') .4746 .3206 .9346 6.0(2)
H(13') 1.0535 .0765 1.3093 6.8(2)
H(14') 1.2108 .0442 1.4640 6.2(2)
H(16') .9863 .3298 1.5600 5.3(2)
H(17') .8290 .3620 1.4054 5.9(2)
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
C(1) O(2) C(3) 119.4(2) yes
O(2) C(3) C(4) 126.8(4) yes
O(2) C(3) C(8) 113.8(3) yes
C(4) C(3) C(8) 119.3(4) yes
C(3) C(4) C(5) 119.9(4) yes
C(4) C(5) C(6) 119.9(3) yes
C(5) C(6) C(7) 119.9(3) yes
C(5) C(6) N(9) 120.7(3) yes
C(7) C(6) N(9) 119.5(3) yes
C(6) C(7) C(8) 120.2(3) yes
C(3) C(8) C(7) 120.7(3) yes
N(10) N(9) O(11) 124.6(3) yes
N(9) N(10) C(12) 119.8(3) yes
N(10) C(12) C(13) 112.7(3) yes
N(10) C(12) C(17) 127.5(3) yes
C(13) C(12) C(17) 119.4(3) yes
C(12) C(13) C(14) 119.6(3) yes
C(13) C(14) C(15) 121.4(4) yes
C(14) C(15) C(16) 118.5(4) yes
C(14) C(15) O(18) 115.5(3) yes
C(16) C(15) O(18) 126.1(4) yes
C(15) C(16) C(17) 121.0(4) yes
C(6) N(9) N(10) 116.5(3) yes
C(6) N(9) O(11) 118.9(3) yes
C(1) O(2) C(3') 116.6(3) yes
O(2) C(3') C(4') 119.5(6) yes
O(2) C(3') C(8') 120.3(6) yes
C(5') C(6') N(9') 111.7(7) yes
C(14') C(15') O(18) 119.7(5) yes
C(16') C(15') O(18) 120.3(5) yes
C(15') O(18) C(19) 114.7(3) yes
C(12) C(17) C(16) 120.0(3) yes
C(15) O(18) C(19) 119.1(2) yes
C(12') N(10') O(11) 123.4(7) yes
N(9') N(10') C(12') 116.4(7) yes
N(10') C(12') C(13') 121.1(6) yes
C(7') C(6') N(9') 128.4(7) yes
C(6') N(9') N(10') 120.6(8) yes
O(11) N(10') N(9') 120.1(7) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) O(2) 1.423(4) yes
O(2) C(3) 1.337(3) yes
C(3) C(4) 1.384(6) yes
C(3) C(8) 1.385(5) yes
C(4) C(5) 1.394(5) yes
C(5) C(6) 1.387(5) yes
C(6) C(7) 1.375(5) yes
C(6) N(9) 1.445(4) yes
C(7) C(8) 1.382(5) yes
N(9) N(10) 1.281(4) yes
O(2) C(3') 1.392(7) yes
C(6') N(9') 1.412(9) yes
N(9') N(10') 1.272(9) yes
N(9) O(11) 1.288(3) yes
N(10) C(12) 1.428(4) yes
C(12) C(13) 1.404(5) yes
C(12) C(17) 1.378(5) yes
C(13) C(14) 1.378(4) yes
C(14) C(15) 1.377(6) yes
C(15) C(16) 1.394(6) yes
C(15) O(18) 1.365(4) yes
C(16) C(17) 1.383(5) yes
O(18) C(19) 1.428(3) yes
N(10') C(12') 1.422(9) yes
C(15') O(18) 1.342(6) yes
N(10') O(11) 1.319(8) yes