#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/15/2011541.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_2011541
loop_
_publ_author_name
'Hosomi, Hiroyuki'
'Ohba, Shigeru'
'Ito, Yoshikatsu'
_publ_section_title
;
 4,5-Dichlorophthalic acid--trans-cinnamamide(1/2) and
 3,4,5,6-tetrachlorophthalic acid--trans-cinnamamide(1/2)
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e509
_journal_page_last               e510
_journal_paper_doi               10.1107/S010827010001338X
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          'C8 H4 Cl2 O4, 2C9 H9 N1 O1'
_chemical_formula_moiety         'C8 H4 Cl2 O4, 2C9 H9 N1 O1'
_chemical_formula_sum            'C26 H22 Cl2 N2 O6'
_chemical_formula_weight         529.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                93.611(5)
_cell_angle_beta                 105.676(5)
_cell_angle_gamma                100.636(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6821(7)
_cell_length_b                   18.4661(12)
_cell_length_c                   7.4203(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.3
_cell_volume                     1246.43(15)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_data_reduction
;TEXSAN
(Molecular Structure Corporation, 1999)
;
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .013
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6174
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .305
_exptl_absorpt_correction_T_max  .955
_exptl_absorpt_correction_T_min  .745
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate-like
_exptl_crystal_size_max          .7
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .15
_refine_diff_density_max         .48
_refine_diff_density_min         -.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.28
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5732
_refine_ls_R_factor_gt           .047
_refine_ls_shift/su_max          .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.10P)²+0.30P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .198
_reflns_number_gt                4328
_reflns_number_total             5732
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0400.cif
_cod_data_source_block           I
_cod_original_cell_volume        1246.4(2)
_cod_database_code               2011541
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
Cl1 .50890(10) .47673(4) .25080(10) .0701(3) Uani d . 1.00 . . Cl
Cl2 .19220(10) .46400(4) .30550(10) .0720(3) Uani d . 1.00 . . Cl
O3 .0256(2) .16630(10) .2483(3) .0586(5) Uani d . 1.00 . . O
O4 .2324(2) .13950(10) .4237(3) .0515(5) Uani d . 1.00 . . O
O5 .3583(2) .14440(10) .1204(3) .0535(5) Uani d . 1.00 . . O
O6 .5674(2) .18770(10) .3476(3) .0575(5) Uani d . 1.00 . . O
O7 .1236(2) .00050(10) .3819(3) .0514(4) Uani d . 1.00 . . O
O8 .3903(2) .01360(10) .1227(3) .0506(4) Uani d . 1.00 . . O
N9 -.0899(3) .0071(2) .1748(4) .0614(6) Uani d . 1.00 . . N
N10 .6071(3) .03450(10) .3462(4) .0533(6) Uani d . 1.00 . . N
C11 .1560(3) .18250(10) .3226(3) .0412(5) Uani d . 1.00 . . C
C12 .2470(3) .25550(10) .3088(3) .0413(5) Uani d . 1.00 . . C
C13 .1900(3) .3187(2) .3190(4) .0472(5) Uani d . 1.00 . . C
C14 .2698(3) .38680(10) .3026(4) .0488(6) Uani d . 1.00 . . C
C15 .4096(3) .39300(10) .2793(4) .0487(6) Uani d . 1.00 . . C
C16 .4678(3) .3299(2) .2706(4) .0472(5) Uani d . 1.00 . . C
C17 .3867(3) .26170(10) .2826(3) .0407(5) Uani d . 1.00 . . C
C18 .4477(3) .19380(10) .2552(3) .0417(5) Uani d . 1.00 . . C
C19 .0025(3) -.0316(2) .2704(3) .0471(5) Uani d . 1.00 . . C
C20 -.0452(3) -.1135(2) .2399(4) .0558(7) Uani d . 1.00 . . C
C21 .0356(3) -.1576(2) .3216(4) .0538(6) Uani d . 1.00 . . C
C22 -.0054(3) -.2396(2) .3044(4) .0523(6) Uani d . 1.00 . . C
C23 .0999(4) -.2788(2) .3870(5) .0636(7) Uani d . 1.00 . . C
C24 .0667(5) -.3556(2) .3740(6) .0761(9) Uani d . 1.00 . . C
C25 -.0724(5) -.3943(2) .2790(5) .0754(10) Uani d . 1.00 . . C
C26 -.1775(4) -.3566(2) .1979(5) .0744(10) Uani d . 1.00 . . C
C27 -.1460(4) -.2796(2) .2101(5) .0646(8) Uani d . 1.00 . . C
C28 .4910(3) -.01060(10) .2291(3) .0427(5) Uani d . 1.00 . . C
C29 .4840(3) -.09150(10) .2272(4) .0480(6) Uani d . 1.00 . . C
C30 .3745(3) -.14030(10) .1118(4) .0465(5) Uani d . 1.00 . . C
C31 .3543(3) -.22120(10) .0949(4) .0458(5) Uani d . 1.00 . . C
C32 .4541(4) -.2569(2) .2086(4) .0568(7) Uani d . 1.00 . . C
C33 .4290(4) -.3338(2) .1909(5) .0651(8) Uani d . 1.00 . . C
C34 .3065(4) -.3754(2) .0594(5) .0616(7) Uani d . 1.00 . . C
C35 .2084(4) -.3415(2) -.0555(6) .0685(8) Uani d . 1.00 . . C
C36 .2319(3) -.2642(2) -.0370(5) .0621(7) Uani d . 1.00 . . C
H4 .175(4) .099(2) .411(5) .07450(10) Uiso d . 1.00 . . H
H5 .392(4) .105(2) .125(5) .07310(10) Uiso d . 1.00 . . H
H9A -.062(6) .066(2) .196(7) .1271(2) Uiso d . 1.00 . . H
H9B -.168(6) -.020(3) .096(7) .1089(2) Uiso d . 1.00 . . H
H10A .612(3) .090(2) .353(4) .05770(10) Uiso d . 1.00 . . H
H10B .673(4) .024(2) .419(6) .07300(10) Uiso d . 1.00 . . H
H13 .096(4) .312(2) .337(4) .05800(10) Uiso d . 1.00 . . H
H16 .560(4) .336(2) .251(4) .05740(10) Uiso d . 1.00 . . H
H20 -.136(4) -.127(2) .161(5) .06470(10) Uiso d . 1.00 . . H
H21 .131(4) -.139(2) .400(5) .06310(10) Uiso d . 1.00 . . H
H23 .205(5) -.252(2) .453(6) .0886(2) Uiso d . 1.00 . . H
H24 .138(5) -.380(2) .415(6) .0895(2) Uiso d . 1.00 . . H
H25 -.104(5) -.453(3) .269(7) .1077(2) Uiso d . 1.00 . . H
H26 -.279(5) -.380(3) .134(6) .0922(2) Uiso d . 1.00 . . H
H27 -.218(4) -.257(2) .152(6) .07970(10) Uiso d . 1.00 . . H
H29 .568(3) -.106(2) .316(4) .04689(9) Uiso d . 1.00 . . H
H30 .299(4) -.119(2) .029(4) .05500(10) Uiso d . 1.00 . . H
H32 .546(5) -.224(2) .307(6) .0936(2) Uiso d . 1.00 . . H
H33 .507(4) -.354(2) .271(5) .07760(10) Uiso d . 1.00 . . H
H34 .290(4) -.432(2) .042(5) .07190(10) Uiso d . 1.00 . . H
H35 .124(5) -.369(3) -.139(6) .1004(2) Uiso d . 1.00 . . H
H36 .163(5) -.240(2) -.111(6) .0916(2) Uiso d . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .003 .002
;International Tables for Crystallography
(1992, Vol. C)
;
H H .000 .000
;International Tables for Crystallography
(1992, Vol. C)
;
Cl Cl .148 .159
;International Tables for Crystallography
(1992, Vol. C)
;
N N .006 .003
;International Tables for Crystallography
(1992, Vol. C)
;
O O .011 .006
;International Tables for Crystallography
(1992, Vol. C)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O4 H4 1_555 1_555 1_555 105(2) no
C18 O5 H5 1_555 1_555 1_555 107(2) no
C19 N9 H9A 1_555 1_555 1_555 119(2) no
C19 N9 H9B 1_555 1_555 1_555 113(3) no
H9A N9 H9B 1_555 1_555 1_555 126(4) no
C28 N10 H10A 1_555 1_555 1_555 118.0(10) no
C28 N10 H10B 1_555 1_555 1_555 128(2) no
H10A N10 H10B 1_555 1_555 1_555 112(3) no
O3 C11 O4 1_555 1_555 1_555 124.6(2) no
O3 C11 C12 1_555 1_555 1_555 122.1(2) no
O4 C11 C12 1_555 1_555 1_555 113.3(2) no
C11 C12 C13 1_555 1_555 1_555 118.7(2) no
C11 C12 C17 1_555 1_555 1_555 122.1(2) no
C13 C12 C17 1_555 1_555 1_555 119.2(2) no
C12 C13 C14 1_555 1_555 1_555 120.2(3) no
C12 C13 H13 1_555 1_555 1_555 116(2) no
C14 C13 H13 1_555 1_555 1_555 123(2) no
Cl2 C14 C13 1_555 1_555 1_555 119.0(2) no
Cl2 C14 C15 1_555 1_555 1_555 120.5(2) no
C13 C14 C15 1_555 1_555 1_555 120.5(3) no
Cl1 C15 C14 1_555 1_555 1_555 121.4(2) no
Cl1 C15 C16 1_555 1_555 1_555 119.0(2) no
C14 C15 C16 1_555 1_555 1_555 119.6(2) no
C15 C16 C17 1_555 1_555 1_555 119.9(3) no
C15 C16 H16 1_555 1_555 1_555 116(2) no
C17 C16 H16 1_555 1_555 1_555 123(2) no
C12 C17 C16 1_555 1_555 1_555 120.6(2) no
C12 C17 C18 1_555 1_555 1_555 120.9(2) no
C16 C17 C18 1_555 1_555 1_555 118.4(2) no
O5 C18 O6 1_555 1_555 1_555 125.0(3) no
O5 C18 C17 1_555 1_555 1_555 112.6(2) no
O6 C18 C17 1_555 1_555 1_555 122.4(2) no
O7 C19 N9 1_555 1_555 1_555 120.8(3) no
O7 C19 C20 1_555 1_555 1_555 122.1(2) no
N9 C19 C20 1_555 1_555 1_555 117.1(2) no
C19 C20 C21 1_555 1_555 1_555 123.2(2) no
C19 C20 H20 1_555 1_555 1_555 110(2) no
C21 C20 H20 1_555 1_555 1_555 126(2) no
C20 C21 C22 1_555 1_555 1_555 126.7(2) no
C20 C21 H21 1_555 1_555 1_555 120(2) no
C22 C21 H21 1_555 1_555 1_555 112(2) no
C21 C22 C23 1_555 1_555 1_555 119.0(2) no
C21 C22 C27 1_555 1_555 1_555 122.9(3) no
C23 C22 C27 1_555 1_555 1_555 118.1(3) no
C22 C23 C24 1_555 1_555 1_555 121.1(3) no
C22 C23 H23 1_555 1_555 1_555 120(2) no
C24 C23 H23 1_555 1_555 1_555 117(2) no
C23 C24 C25 1_555 1_555 1_555 120.1(4) no
C23 C24 H24 1_555 1_555 1_555 119(2) no
C25 C24 H24 1_555 1_555 1_555 119(2) no
C24 C25 C26 1_555 1_555 1_555 119.5(3) no
C24 C25 H25 1_555 1_555 1_555 122(2) no
C26 C25 H25 1_555 1_555 1_555 117(2) no
C25 C26 C27 1_555 1_555 1_555 121.0(3) no
C25 C26 H26 1_555 1_555 1_555 124(2) no
C27 C26 H26 1_555 1_555 1_555 114(2) no
C22 C27 C26 1_555 1_555 1_555 120.2(3) no
C22 C27 H27 1_555 1_555 1_555 121(2) no
C26 C27 H27 1_555 1_555 1_555 117(2) no
O8 C28 N10 1_555 1_555 1_555 121.6(2) no
O8 C28 C29 1_555 1_555 1_555 120.7(2) no
N10 C28 C29 1_555 1_555 1_555 117.7(2) no
C28 C29 C30 1_555 1_555 1_555 121.8(2) no
C28 C29 H29 1_555 1_555 1_555 115.0(10) no
C30 C29 H29 1_555 1_555 1_555 122.0(10) no
C29 C30 C31 1_555 1_555 1_555 127.4(2) no
C29 C30 H30 1_555 1_555 1_555 115.0(10) no
C31 C30 H30 1_555 1_555 1_555 117.0(10) no
C30 C31 C32 1_555 1_555 1_555 122.1(2) no
C30 C31 C36 1_555 1_555 1_555 119.4(2) no
C32 C31 C36 1_555 1_555 1_555 118.5(3) no
C31 C32 C33 1_555 1_555 1_555 120.2(2) no
C31 C32 H32 1_555 1_555 1_555 117(2) no
C33 C32 H32 1_555 1_555 1_555 121(2) no
C32 C33 C34 1_555 1_555 1_555 120.4(3) no
C32 C33 H33 1_555 1_555 1_555 114(2) no
C34 C33 H33 1_555 1_555 1_555 124(2) no
C33 C34 C35 1_555 1_555 1_555 120.4(3) no
C33 C34 H34 1_555 1_555 1_555 120.0(10) no
C35 C34 H34 1_555 1_555 1_555 118.0(10) no
C34 C35 C36 1_555 1_555 1_555 119.6(3) no
C34 C35 H35 1_555 1_555 1_555 120(3) no
C36 C35 H35 1_555 1_555 1_555 119(3) no
C31 C36 C35 1_555 1_555 1_555 120.9(3) no
C31 C36 H36 1_555 1_555 1_555 118(2) no
C35 C36 H36 1_555 1_555 1_555 120(2) no
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
Cl1 C15 . . 1.720(3) yes
Cl2 C14 . . 1.731(3) yes
O3 C11 . . 1.204(3) yes
O4 C11 . . 1.317(3) yes
O4 H4 . . .83(4) no
O5 C18 . . 1.307(3) yes
O5 H5 . . .85(4) no
O6 C18 . . 1.206(3) yes
O7 C19 . . 1.252(3) yes
O8 C28 . . 1.251(3) yes
N9 C19 . . 1.331(4) yes
N9 H9A . . 1.06(3) no
N9 H9B . . .87(4) no
N10 C28 . . 1.322(3) yes
N10 H10A . . 1.01(4) no
N10 H10B . . .78(4) no
C11 C12 . . 1.494(3) no
C12 C13 . . 1.388(4) no
C12 C17 . . 1.402(4) no
C13 C14 . . 1.380(4) no
C13 H13 . . .94(4) no
C14 C15 . . 1.395(4) no
C15 C16 . . 1.391(4) no
C16 C17 . . 1.378(4) no
C16 H16 . . .93(4) no
C17 C18 . . 1.507(4) no
C19 C20 . . 1.482(4) yes
C20 C21 . . 1.298(4) yes
C20 H20 . . .89(3) no
C21 C22 . . 1.481(4) no
C21 H21 . . .94(3) no
C22 C23 . . 1.389(5) no
C22 C27 . . 1.391(4) no
C23 C24 . . 1.386(5) no
C23 H23 . . 1.01(4) no
C24 C25 . . 1.376(5) no
C24 H24 . . .89(5) no
C25 C26 . . 1.366(6) no
C25 H25 . . 1.06(5) no
C26 C27 . . 1.390(5) no
C26 H26 . . .97(4) no
C27 H27 . . .90(4) no
C28 C29 . . 1.481(4) yes
C29 C30 . . 1.315(3) yes
C29 H29 . . .99(3) no
C30 C31 . . 1.464(4) no
C30 H30 . . .97(3) no
C31 C32 . . 1.394(4) no
C31 C36 . . 1.386(3) no
C32 C33 . . 1.386(4) no
C32 H32 . . 1.04(4) no
C33 C34 . . 1.376(4) no
C33 H33 . . .97(4) no
C34 C35 . . 1.369(5) no
C34 H34 . . 1.02(4) no
C35 C36 . . 1.395(4) no
C35 H35 . . .92(4) no
C36 H36 . . .94(5) no
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
O4 H4 O7 . .83(4) 1.78(4) 2.553(3) 155(5)
O5 H5 O8 . .84(4) 1.69(4) 2.491(3) 158(4)
N9 H9A O3 . 1.06(3) 1.86(3) 2.905(4) 168(5)
N9 H9B O8 2_555 .87(4) 2.35(5) 3.081(3) 142(5)
N10 H10A O6 . 1.01(4) 1.94(4) 2.923(3) 165(3)
N10 H10B O7 2_656 .78(4) 2.27(4) 3.039(3) 175(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652310
