#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012983.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012983
loop_
_publ_author_name
'Huang, Xinjiang'
'Kuhn, Genevieve H.'
'Nesterov, Vladimir N.'
'Averkiev, Boris B.'
'Penn, Benjamin'
'Antipin, Mikhail Yu.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
(E)-(4-Hydroxyphenyl)(4-nitrophenyl)diazene,
(E)-(4-methoxyphenyl)(4-nitrophenyl)diazene and
(E)-[4-(6-bromohexyloxy)phenyl](4-cyanophenyl)diazene
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              o624
_journal_page_last               o628
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C19 H20 Br N3 O'
_chemical_formula_sum            'C19 H20 Br N3 O'
_chemical_formula_weight         386.29
_chemical_melting_point          376
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  -P1
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                86.502(5)
_cell_angle_beta                 80.511(5)
_cell_angle_gamma                87.604(5)
_cell_formula_units_Z            4
_cell_length_a                   7.4279(18)
_cell_length_b                   12.009(3)
_cell_length_c                   19.552(5)
_cell_measurement_temperature    110(2)
_cell_volume                     1716.2(7)
_diffrn_ambient_temperature      110(2)
_exptl_crystal_density_diffrn    1.495
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2012983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1A 0.06933(6) -0.11321(3) 0.07294(2) 0.03930(14) Uani d . 1 . . Br
O1A 0.5947(3) 0.25090(19) 0.25472(13) 0.0287(6) Uani d . 1 . . O
N1A -0.1448(5) 0.8239(3) 0.77340(17) 0.0388(9) Uani d . 1 . . N
N2A 0.2520(4) 0.4768(2) 0.52729(16) 0.0232(7) Uani d . 1 . . N
N3A 0.2536(4) 0.5135(2) 0.46568(16) 0.0225(7) Uani d . 1 . . N
C1A 0.0073(5) 0.6891(3) 0.68080(18) 0.0222(9) Uani d . 1 . . C
C2A 0.0242(5) 0.7274(3) 0.61082(18) 0.0233(9) Uani d . 1 . . C
H2AB -0.0189 0.8004 0.5988 0.028 Uiso calc R 1 . . H
C3A 0.1027(5) 0.6595(3) 0.56028(18) 0.0232(9) Uani d . 1 . . C
H3AB 0.1132 0.6852 0.5129 0.028 Uiso calc R 1 . . H
C4A 0.1677(5) 0.5529(3) 0.57728(19) 0.0220(9) Uani d . 1 . . C
C5A 0.1530(5) 0.5149(3) 0.64745(19) 0.0257(9) Uani d . 1 . . C
H5AA 0.1997 0.4428 0.6594 0.031 Uiso calc R 1 . . H
C6A 0.0707(5) 0.5827(3) 0.69868(19) 0.0258(9) Uani d . 1 . . C
H6AA 0.0573 0.5567 0.7461 0.031 Uiso calc R 1 . . H
C7A 0.3367(5) 0.4415(3) 0.41379(19) 0.0211(9) Uani d . 1 . . C
C8A 0.3483(5) 0.4841(3) 0.34616(19) 0.0234(9) Uani d . 1 . . C
H8AA 0.2998 0.5569 0.3371 0.028 Uiso calc R 1 . . H
C9A 0.4303(5) 0.4219(3) 0.29110(19) 0.0250(9) Uani d . 1 . . C
H9AA 0.4355 0.4513 0.2446 0.030 Uiso calc R 1 . . H
C10A 0.5043(5) 0.3164(3) 0.30449(19) 0.0243(9) Uani d . 1 . . C
C11A 0.4877(5) 0.2714(3) 0.37308(19) 0.0259(9) Uani d . 1 . . C
H11A 0.5331 0.1977 0.3822 0.031 Uiso calc R 1 . . H
C12A 0.4057(5) 0.3337(3) 0.42727(19) 0.0234(9) Uani d . 1 . . C
H12A 0.3961 0.3035 0.4737 0.028 Uiso calc R 1 . . H
C13A -0.0769(5) 0.7636(3) 0.7332(2) 0.0269(9) Uani d . 1 . . C
C14A 0.6199(5) 0.2953(3) 0.18423(18) 0.0273(9) Uani d . 1 . . C
H14A 0.6842 0.3666 0.1802 0.033 Uiso calc R 1 . . H
H14B 0.5000 0.3098 0.1690 0.033 Uiso calc R 1 . . H
C15A 0.7316(5) 0.2108(3) 0.1394(2) 0.0347(10) Uani d . 1 . . C
H15A 0.7619 0.2439 0.0915 0.042 Uiso calc R 1 . . H
H15B 0.8477 0.1941 0.1571 0.042 Uiso calc R 1 . . H
C16A 0.6353(5) 0.1029(3) 0.13753(19) 0.0295(10) Uani d . 1 . . C
H16A 0.5849 0.0770 0.1856 0.035 Uiso calc R 1 . . H
H16B 0.7258 0.0455 0.1181 0.035 Uiso calc R 1 . . H
C17A 0.4806(5) 0.1130(3) 0.09452(19) 0.0286(9) Uani d . 1 . . C
H17A 0.5329 0.1281 0.0450 0.034 Uiso calc R 1 . . H
H17B 0.3988 0.1772 0.1096 0.034 Uiso calc R 1 . . H
C18A 0.3691(5) 0.0075(3) 0.10173(19) 0.0282(9) Uani d . 1 . . C
H18A 0.4483 -0.0559 0.0834 0.034 Uiso calc R 1 . . H
H18B 0.3230 -0.0107 0.1514 0.034 Uiso calc R 1 . . H
C19A 0.2112(5) 0.0234(3) 0.0628(2) 0.0322(10) Uani d . 1 . . C
H19A 0.2570 0.0413 0.0131 0.039 Uiso calc R 1 . . H
H19B 0.1317 0.0867 0.0811 0.039 Uiso calc R 1 . . H
Br1B 0.90469(5) 0.58117(3) 0.90418(2) 0.03685(14) Uani d . 1 . . Br
O1B 0.4040(3) 0.27510(19) 0.72551(12) 0.0265(6) Uani d . 1 . . O
N1B 1.1512(4) -0.3268(3) 0.22147(16) 0.0334(9) Uani d . 1 . . N
N2B 0.7523(4) 0.0223(2) 0.46623(16) 0.0241(7) Uani d . 1 . . N
N3B 0.7438(4) -0.0135(2) 0.52915(16) 0.0241(7) Uani d . 1 . . N
C1B 0.9971(4) -0.1935(3) 0.31539(19) 0.0223(9) Uani d . 1 . . C
C2B 0.9820(5) -0.2303(3) 0.38463(18) 0.0219(9) Uani d . 1 . . C
H2BB 1.0272 -0.3027 0.3969 0.026 Uiso calc R 1 . . H
C3B 0.9017(5) -0.1619(3) 0.43503(18) 0.0236(9) Uani d . 1 . . C
H3BB 0.8889 -0.1876 0.4825 0.028 Uiso calc R 1 . . H
C4B 0.8382(5) -0.0547(3) 0.41744(19) 0.0217(9) Uani d . 1 . . C
C5B 0.8551(5) -0.0185(3) 0.34788(19) 0.0239(9) Uani d . 1 . . C
H5BA 0.8103 0.0541 0.3358 0.029 Uiso calc R 1 . . H
C6B 0.9354(5) -0.0856(3) 0.29638(19) 0.0250(9) Uani d . 1 . . C
H6BA 0.9490 -0.0598 0.2490 0.030 Uiso calc R 1 . . H
C7B 0.6596(5) 0.0621(3) 0.57813(19) 0.0208(9) Uani d . 1 . . C
C8B 0.6449(5) 0.0283(3) 0.64709(19) 0.0252(9) Uani d . 1 . . C
H8BA 0.6927 -0.0432 0.6599 0.030 Uiso calc R 1 . . H
C9B 0.5607(5) 0.0975(3) 0.69883(19) 0.0243(9) Uani d . 1 . . C
H9BA 0.5504 0.0736 0.7465 0.029 Uiso calc R 1 . . H
C10B 0.4924(5) 0.2016(3) 0.67924(19) 0.0234(9) Uani d . 1 . . C
C11B 0.5102(5) 0.2373(3) 0.60966(18) 0.0214(9) Uani d . 1 . . C
H11B 0.4658 0.3095 0.5967 0.026 Uiso calc R 1 . . H
C12B 0.5915(5) 0.1686(3) 0.55995(18) 0.0223(9) Uani d . 1 . . C
H12B 0.6022 0.1931 0.5124 0.027 Uiso calc R 1 . . H
C13B 1.0837(5) -0.2672(3) 0.2627(2) 0.0258(9) Uani d . 1 . . C
C14B 0.3921(5) 0.2462(3) 0.79858(18) 0.0275(9) Uani d . 1 . . C
H14C 0.5156 0.2308 0.8104 0.033 Uiso calc R 1 . . H
H14D 0.3193 0.1787 0.8115 0.033 Uiso calc R 1 . . H
C15B 0.3010(5) 0.3444(3) 0.83716(18) 0.0271(9) Uani d . 1 . . C
H15C 0.3627 0.4134 0.8174 0.033 Uiso calc R 1 . . H
H15D 0.1723 0.3519 0.8298 0.033 Uiso calc R 1 . . H
C16B 0.3054(5) 0.3335(3) 0.91401(19) 0.0323(10) Uani d . 1 . . C
H16C 0.2497 0.2622 0.9328 0.039 Uiso calc R 1 . . H
H16D 0.2280 0.3946 0.9363 0.039 Uiso calc R 1 . . H
C17B 0.4943(5) 0.3365(3) 0.93525(19) 0.0282(9) Uani d . 1 . . C
H17C 0.4812 0.3259 0.9864 0.034 Uiso calc R 1 . . H
H17D 0.5710 0.2736 0.9149 0.034 Uiso calc R 1 . . H
C18B 0.5911(5) 0.4451(3) 0.91217(19) 0.0262(9) Uani d . 1 . . C
H18C 0.6046 0.4567 0.8610 0.031 Uiso calc R 1 . . H
H18D 0.5169 0.5085 0.9331 0.031 Uiso calc R 1 . . H
C19B 0.7783(5) 0.4415(3) 0.93413(19) 0.0297(9) Uani d . 1 . . C
H19C 0.8522 0.3779 0.9133 0.036 Uiso calc R 1 . . H
H19D 0.7647 0.4302 0.9853 0.036 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1A 0.0309(3) 0.0316(3) 0.0571(3) -0.0023(2) -0.0119(2) -0.0021(2)
O1A 0.0300(16) 0.0271(15) 0.0306(16) 0.0037(12) -0.0064(13) -0.0139(13)
N1A 0.049(2) 0.035(2) 0.028(2) 0.0147(18) 0.0047(19) -0.0083(17)
N2A 0.0214(18) 0.0230(18) 0.0249(19) 0.0009(14) -0.0026(15) -0.0024(15)
N3A 0.0187(17) 0.0226(18) 0.0261(19) 0.0002(14) -0.0022(15) -0.0059(15)
C1A 0.018(2) 0.020(2) 0.028(2) -0.0020(16) -0.0001(18) -0.0052(18)
C2A 0.019(2) 0.020(2) 0.032(2) -0.0025(16) -0.0052(19) -0.0041(18)
C3A 0.023(2) 0.023(2) 0.024(2) 0.0001(17) -0.0069(19) -0.0032(18)
C4A 0.015(2) 0.021(2) 0.028(2) -0.0012(16) 0.0012(18) -0.0064(18)
C5A 0.022(2) 0.018(2) 0.037(2) 0.0019(16) -0.006(2) -0.0047(19)
C6A 0.032(2) 0.026(2) 0.020(2) -0.0012(18) -0.0044(19) -0.0028(18)
C7A 0.015(2) 0.021(2) 0.028(2) -0.0022(16) -0.0037(18) -0.0066(18)
C8A 0.019(2) 0.018(2) 0.033(2) 0.0021(16) -0.0062(19) -0.0037(18)
C9A 0.029(2) 0.025(2) 0.020(2) -0.0013(17) -0.0024(18) -0.0002(18)
C10A 0.019(2) 0.027(2) 0.026(2) -0.0031(17) 0.0013(18) -0.0076(19)
C11A 0.022(2) 0.022(2) 0.036(2) 0.0057(17) -0.0095(19) -0.0075(19)
C12A 0.022(2) 0.024(2) 0.025(2) 0.0030(17) -0.0062(18) -0.0027(18)
C13A 0.024(2) 0.029(2) 0.029(2) -0.0039(18) -0.009(2) 0.0016(19)
C14A 0.032(2) 0.028(2) 0.022(2) -0.0082(18) 0.0005(19) -0.0077(18)
C15A 0.023(2) 0.040(3) 0.041(3) -0.0014(19) -0.001(2) -0.010(2)
C16A 0.034(2) 0.023(2) 0.033(2) 0.0057(18) -0.006(2) -0.0102(18)
C17A 0.026(2) 0.027(2) 0.033(2) 0.0046(17) -0.004(2) -0.0096(18)
C18A 0.023(2) 0.027(2) 0.036(2) 0.0025(17) -0.009(2) -0.0058(19)
C19A 0.026(2) 0.027(2) 0.044(3) 0.0019(17) -0.007(2) -0.0076(19)
Br1B 0.0338(3) 0.0364(3) 0.0393(3) -0.0085(2) 0.0007(2) -0.0060(2)
O1B 0.0245(15) 0.0263(15) 0.0284(15) 0.0026(11) -0.0007(13) -0.0122(12)
N1B 0.038(2) 0.034(2) 0.028(2) 0.0033(16) -0.0022(18) -0.0039(17)
N2B 0.0229(18) 0.0219(18) 0.0271(19) 0.0004(14) -0.0031(16) -0.0034(15)
N3B 0.0192(18) 0.0212(18) 0.032(2) 0.0016(14) -0.0021(16) -0.0072(16)
C1B 0.014(2) 0.022(2) 0.031(2) -0.0006(16) -0.0016(18) -0.0075(18)
C2B 0.020(2) 0.021(2) 0.025(2) 0.0035(16) -0.0050(18) -0.0029(18)
C3B 0.022(2) 0.027(2) 0.023(2) 0.0007(17) -0.0067(19) -0.0023(19)
C4B 0.016(2) 0.019(2) 0.030(2) 0.0004(16) -0.0020(18) -0.0043(18)
C5B 0.023(2) 0.019(2) 0.030(2) 0.0006(17) -0.0061(19) -0.0025(18)
C6B 0.026(2) 0.026(2) 0.023(2) -0.0019(18) -0.0052(19) -0.0016(18)
C7B 0.015(2) 0.023(2) 0.025(2) 0.0011(16) -0.0037(17) -0.0067(18)
C8B 0.023(2) 0.020(2) 0.034(2) 0.0008(17) -0.010(2) -0.0023(19)
C9B 0.023(2) 0.024(2) 0.026(2) -0.0033(17) -0.0027(18) -0.0014(18)
C10B 0.016(2) 0.023(2) 0.032(2) 0.0017(16) -0.0048(18) -0.0109(19)
C11B 0.018(2) 0.018(2) 0.028(2) 0.0025(16) -0.0044(18) -0.0017(18)
C12B 0.025(2) 0.018(2) 0.024(2) 0.0036(16) -0.0049(19) -0.0029(17)
C13B 0.026(2) 0.028(2) 0.025(2) -0.0019(18) -0.0077(19) 0.0035(19)
C14B 0.032(2) 0.027(2) 0.024(2) 0.0040(18) -0.0055(19) -0.0117(18)
C15B 0.024(2) 0.031(2) 0.026(2) 0.0007(18) -0.0037(19) -0.0058(19)
C16B 0.025(2) 0.033(2) 0.037(3) -0.0014(18) 0.002(2) -0.011(2)
C17B 0.030(2) 0.028(2) 0.028(2) 0.0043(18) -0.0039(19) -0.0120(18)
C18B 0.024(2) 0.024(2) 0.031(2) 0.0071(16) -0.0049(19) -0.0063(18)
C19B 0.032(2) 0.024(2) 0.034(2) -0.0040(17) -0.008(2) -0.0034(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C19A . . 1.970(3) no
O1A C10A . . 1.360(4) no
O1A C14A . . 1.433(4) no
N1A C13A . . 1.143(4) no
N2A N3A . . 1.256(4) yes
N2A C4A . . 1.430(4) yes
N3A C7A . . 1.420(4) yes
C1A C6A . . 1.388(5) no
C1A C2A . . 1.404(5) no
C1A C13A . . 1.447(5) no
C2A C3A . . 1.360(4) no
C2A H2AB . . 0.9500 no
C3A C4A . . 1.390(5) no
C3A H3AB . . 0.9500 no
C4A C5A . . 1.407(5) no
C5A C6A . . 1.377(4) no
C5A H5AA . . 0.9500 no
C6A H6AA . . 0.9500 no
C7A C8A . . 1.379(5) no
C7A C12A . . 1.398(5) no
C8A C9A . . 1.390(4) no
C8A H8AA . . 0.9500 no
C9A C10A . . 1.387(5) no
C9A H9AA . . 0.9500 no
C10A C11A . . 1.403(5) no
C11A C12A . . 1.379(4) no
C11A H11A . . 0.9500 no
C12A H12A . . 0.9500 no
C14A C15A . . 1.512(5) no
C14A H14A . . 0.9900 no
C14A H14B . . 0.9900 no
C15A C16A . . 1.511(5) no
C15A H15A . . 0.9900 no
C15A H15B . . 0.9900 no
C16A C17A . . 1.529(5) no
C16A H16A . . 0.9900 no
C16A H16B . . 0.9900 no
C17A C18A . . 1.530(4) no
C17A H17A . . 0.9900 no
C17A H17B . . 0.9900 no
C18A C19A . . 1.499(5) no
C18A H18A . . 0.9900 no
C18A H18B . . 0.9900 no
C19A H19A . . 0.9900 no
C19A H19B . . 0.9900 no
Br1B C19B . . 1.966(3) no
O1B C10B . . 1.372(4) no
O1B C14B . . 1.439(4) no
N1B C13B . . 1.150(4) no
N2B N3B . . 1.271(4) yes
N2B C4B . . 1.425(4) yes
N3B C7B . . 1.412(4) yes
C1B C2B . . 1.386(5) no
C1B C6B . . 1.405(5) no
C1B C13B . . 1.450(5) no
C2B C3B . . 1.366(4) no
C2B H2BB . . 0.9500 no
C3B C4B . . 1.396(5) no
C3B H3BB . . 0.9500 no
C4B C5B . . 1.389(5) no
C5B C6B . . 1.371(4) no
C5B H5BA . . 0.9500 no
C6B H6BA . . 0.9500 no
C7B C8B . . 1.373(5) no
C7B C12B . . 1.403(5) no
C8B C9B . . 1.399(5) no
C8B H8BA . . 0.9500 no
C9B C10B . . 1.386(5) no
C9B H9BA . . 0.9500 no
C10B C11B . . 1.388(5) no
C11B C12B . . 1.361(4) no
C11B H11B . . 0.9500 no
C12B H12B . . 0.9500 no
C14B C15B . . 1.513(4) no
C14B H14C . . 0.9900 no
C14B H14D . . 0.9900 no
C15B C16B . . 1.506(5) no
C15B H15C . . 0.9900 no
C15B H15D . . 0.9900 no
C16B C17B . . 1.530(5) no
C16B H16C . . 0.9900 no
C16B H16D . . 0.9900 no
C17B C18B . . 1.523(5) no
C17B H17C . . 0.9900 no
C17B H17D . . 0.9900 no
C18B C19B . . 1.520(5) no
C18B H18C . . 0.9900 no
C18B H18D . . 0.9900 no
C19B H19C . . 0.9900 no
C19B H19D . . 0.9900 no