#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/15/2011542.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_2011542
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 H2 Cl4 O4, 2C9 H9 N1 O1'
_chemical_formula_moiety         'C8 H2 Cl4 O4, 2C9 H9 N1 O1'
_chemical_formula_sum            'C26 H20 Cl4 N2 O6'
_chemical_formula_weight         598.27
_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                93.48(2)
_cell_angle_beta                 110.570(10)
_cell_angle_gamma                91.58(2)
_cell_formula_units_Z            2
_cell_length_a                   9.937(2)
_cell_length_b                   15.895(4)
_cell_length_c                   9.015(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.4
_cell_volume                     1328.8(5)
_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  .029
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6442
_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    .490
_exptl_absorpt_correction_T_max  .929
_exptl_absorpt_correction_T_min  .772
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .6
_exptl_crystal_size_min          .15
_refine_diff_density_max         .27
_refine_diff_density_min         -.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6092
_refine_ls_R_factor_gt           .038
_refine_ls_shift/su_max          .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0471P)²+0.6677P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .113
_reflns_number_gt                4659
_reflns_number_total             6092
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0400.cif
_cod_data_source_block           II
_cod_database_code               2011542
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 .49893(6) .23519(4) -.17381(6) .0550(2) Uani d . 1.00 . . Cl
Cl2 .64513(7) .41052(4) -.03325(7) .0635(2) Uani d . 1.00 . . Cl
Cl3 .65204(7) .48141(4) .29897(8) .0643(2) Uani d . 1.00 . . Cl
Cl4 .50722(7) .37683(4) .48784(7) .0607(2) Uani d . 1.00 . . Cl
O5 .4875(2) .17930(10) .4817(2) .0567(4) Uani d . 1.00 . . O
O6 .2718(2) .16860(10) .2854(2) .0551(4) Uani d . 1.00 . . O
O7 .4347(2) .07527(9) .1171(2) .0536(4) Uani d . 1.00 . . O
O8 .2709(2) .13090(10) -.0871(2) .0609(4) Uani d . 1.00 . . O
O9 .1870(2) .04000(10) .3962(2) .0590(4) Uani d . 1.00 . . O
O10 .2815(2) -.05220(10) .0875(2) .0695(5) Uani d . 1.00 . . O
N11 .3913(3) .0297(2) .6034(3) .0685(6) Uani d . 1.00 . . N
N12 .0986(2) -.02010(10) -.1292(3) .0569(5) Uani d . 1.00 . . N
C13 .4064(2) .19670(10) .3535(2) .0430(4) Uani d . 1.00 . . C
C14 .4556(2) .25340(10) .2517(2) .0383(4) Uani d . 1.00 . . C
C15 .5132(2) .33440(10) .3097(2) .0406(4) Uani d . 1.00 . . C
C16 .5719(2) .38350(10) .2217(3) .0432(4) Uani d . 1.00 . . C
C17 .5685(2) .35180(10) .0734(2) .0427(4) Uani d . 1.00 . . C
C18 .5043(2) .27210(10) .0119(2) .0401(4) Uani d . 1.00 . . C
C19 .4483(2) .22260(10) .1004(2) .0383(4) Uani d . 1.00 . . C
C20 .3764(2) .13670(10) .0330(2) .0424(4) Uani d . 1.00 . . C
C21 .2616(3) .00150(10) .5111(3) .0497(5) Uani d . 1.00 . . C
C22 .2127(3) -.0784(2) .5549(3) .0558(6) Uani d . 1.00 . . C
C23 .0864(3) -.1170(2) .4802(3) .0540(5) Uani d . 1.00 . . C
C24 .0322(2) -.19660(10) .5209(3) .0497(5) Uani d . 1.00 . . C
C25 -.1025(3) -.2299(2) .4246(3) .0565(6) Uani d . 1.00 . . C
C26 -.1583(3) -.3039(2) .4577(4) .0659(7) Uani d . 1.00 . . C
C27 -.0817(3) -.3456(2) .5868(4) .0678(7) Uani d . 1.00 . . C
C28 .0522(3) -.3132(2) .6834(4) .0688(7) Uani d . 1.00 . . C
C29 .1096(3) -.2390(2) .6514(3) .0610(6) Uani d . 1.00 . . C
C30 .1571(2) -.06900(10) -.0148(3) .0488(5) Uani d . 1.00 . . C
C31 .0757(3) -.14590(10) -.0068(3) .0520(5) Uani d . 1.00 . . C
C32 .1273(3) -.19610(10) .1102(3) .0497(5) Uani d . 1.00 . . C
C33 .0623(2) -.27700(10) .1278(3) .0493(5) Uani d . 1.00 . . C
C34 -.0698(3) -.3102(2) .0222(4) .0637(7) Uani d . 1.00 . . C
C35 -.1225(3) -.3881(2) .0424(4) .0822(9) Uani d . 1.00 . . C
C36 -.0447(4) -.4341(2) .1665(5) .0823(9) Uani d . 1.00 . . C
C37 .0843(4) -.4016(2) .2715(4) .0767(8) Uani d . 1.00 . . C
C38 .1376(3) -.3229(2) .2528(3) .0601(6) Uani d . 1.00 . . C
H6 .251(4) .128(2) .345(4) .09620(10) Uiso d . 1.00 . . H
H7 .367(4) .022(2) .089(4) .1159(2) Uiso d . 1.00 . . H
H11A .422(3) .073(2) .582(3) .06250(10) Uiso d . 1.00 . . H
H11B .439(4) -.002(2) .681(5) .1079(2) Uiso d . 1.00 . . H
H12A .144(3) .028(2) -.133(3) .06037(9) Uiso d . 1.00 . . H
H12B .014(4) -.034(2) -.203(4) .08500(10) Uiso d . 1.00 . . H
H22 .278(4) -.104(2) .640(4) .10720(10) Uiso d . 1.00 . . H
H23 .023(3) -.089(2) .389(4) .08090(10) Uiso d . 1.00 . . H
H25 -.156(3) -.201(2) .335(4) .07560(10) Uiso d . 1.00 . . H
H26 -.248(4) -.326(2) .392(4) .09050(10) Uiso d . 1.00 . . H
H27 -.119(3) -.396(2) .609(4) .08290(10) Uiso d . 1.00 . . H
H28 .101(3) -.336(2) .769(3) .07150(10) Uiso d . 1.00 . . H
H29 .204(3) -.217(2) .723(3) .07180(10) Uiso d . 1.00 . . H
H31 -.017(3) -.160(2) -.092(3) .07510(10) Uiso d . 1.00 . . H
H32 .223(3) -.180(2) .196(3) .06392(9) Uiso d . 1.00 . . H
H34 -.123(3) -.280(2) -.064(3) .07240(10) Uiso d . 1.00 . . H
H35 -.215(4) -.411(2) -.035(4) .1119(2) Uiso d . 1.00 . . H
H36 -.081(4) -.493(2) .170(4) .10160(10) Uiso d . 1.00 . . H
H37 .138(3) -.431(2) .355(4) .08620(10) Uiso d . 1.00 . . H
H38 .224(3) -.301(2) .326(3) .06197(9) 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
C13 O6 H6 1_555 1_555 1_555 109.0(10) no
C20 O7 H7 1_555 1_555 1_555 111.0(10) no
C21 N11 H11A 1_555 1_555 1_555 117.0(10) no
C21 N11 H11B 1_555 1_555 1_555 117(2) no
H11A N11 H11B 1_555 1_555 1_555 125(2) no
C30 N12 H12A 1_555 1_555 1_555 119.0(10) no
C30 N12 H12B 1_555 1_555 1_555 121(2) no
H12A N12 H12B 1_555 1_555 1_555 119(2) no
O5 C13 O6 1_555 1_555 1_555 125.7(2) no
O5 C13 C14 1_555 1_555 1_555 121.4(2) no
O6 C13 C14 1_555 1_555 1_555 112.9(2) no
C13 C14 C15 1_555 1_555 1_555 120.5(2) no
C13 C14 C19 1_555 1_555 1_555 119.6(2) no
C15 C14 C19 1_555 1_555 1_555 119.9(2) no
Cl4 C15 C14 1_555 1_555 1_555 120.2(2) no
Cl4 C15 C16 1_555 1_555 1_555 119.40(10) no
C14 C15 C16 1_555 1_555 1_555 120.4(2) no
Cl3 C16 C15 1_555 1_555 1_555 120.1(2) no
Cl3 C16 C17 1_555 1_555 1_555 120.2(2) no
C15 C16 C17 1_555 1_555 1_555 119.6(2) no
Cl2 C17 C16 1_555 1_555 1_555 120.0(2) no
Cl2 C17 C18 1_555 1_555 1_555 120.1(2) no
C16 C17 C18 1_555 1_555 1_555 119.9(2) no
Cl1 C18 C17 1_555 1_555 1_555 118.9(2) no
Cl1 C18 C19 1_555 1_555 1_555 120.60(10) no
C17 C18 C19 1_555 1_555 1_555 120.5(2) no
C14 C19 C18 1_555 1_555 1_555 119.6(2) no
C14 C19 C20 1_555 1_555 1_555 119.8(2) no
C18 C19 C20 1_555 1_555 1_555 120.6(2) no
O7 C20 O8 1_555 1_555 1_555 126.2(2) no
O7 C20 C19 1_555 1_555 1_555 114.20(10) no
O8 C20 C19 1_555 1_555 1_555 119.6(2) no
O9 C21 N11 1_555 1_555 1_555 122.1(2) no
O9 C21 C22 1_555 1_555 1_555 123.5(2) no
N11 C21 C22 1_555 1_555 1_555 114.4(2) no
C21 C22 C23 1_555 1_555 1_555 124.5(2) no
C21 C22 H22 1_555 1_555 1_555 117(2) no
C23 C22 H22 1_555 1_555 1_555 117(2) no
C22 C23 C24 1_555 1_555 1_555 126.3(2) no
C22 C23 H23 1_555 1_555 1_555 115.0(10) no
C24 C23 H23 1_555 1_555 1_555 118.0(10) no
C23 C24 C25 1_555 1_555 1_555 118.3(2) no
C23 C24 C29 1_555 1_555 1_555 123.1(2) no
C25 C24 C29 1_555 1_555 1_555 118.6(2) no
C24 C25 C26 1_555 1_555 1_555 120.6(2) no
C24 C25 H25 1_555 1_555 1_555 118.0(10) no
C26 C25 H25 1_555 1_555 1_555 120.0(10) no
C25 C26 C27 1_555 1_555 1_555 120.7(2) no
C25 C26 H26 1_555 1_555 1_555 120(2) no
C27 C26 H26 1_555 1_555 1_555 119(2) no
C26 C27 C28 1_555 1_555 1_555 119.2(3) no
C26 C27 H27 1_555 1_555 1_555 120.0(10) no
C28 C27 H27 1_555 1_555 1_555 119.0(10) no
C27 C28 C29 1_555 1_555 1_555 120.7(3) no
C27 C28 H28 1_555 1_555 1_555 121.0(10) no
C29 C28 H28 1_555 1_555 1_555 117.0(10) no
C24 C29 C28 1_555 1_555 1_555 120.2(2) no
C24 C29 H29 1_555 1_555 1_555 120.0(10) no
C28 C29 H29 1_555 1_555 1_555 119.0(10) no
O10 C30 N12 1_555 1_555 1_555 121.9(2) no
O10 C30 C31 1_555 1_555 1_555 119.5(2) no
N12 C30 C31 1_555 1_555 1_555 118.5(2) no
C30 C31 C32 1_555 1_555 1_555 121.1(2) no
C30 C31 H31 1_555 1_555 1_555 118.0(10) no
C32 C31 H31 1_555 1_555 1_555 120.0(10) no
C31 C32 C33 1_555 1_555 1_555 126.9(2) no
C31 C32 H32 1_555 1_555 1_555 118.0(10) no
C33 C32 H32 1_555 1_555 1_555 114.0(10) no
C32 C33 C34 1_555 1_555 1_555 123.0(2) no
C32 C33 C38 1_555 1_555 1_555 118.2(2) no
C34 C33 C38 1_555 1_555 1_555 118.8(2) no
C33 C34 C35 1_555 1_555 1_555 120.0(3) no
C33 C34 H34 1_555 1_555 1_555 119.0(10) no
C35 C34 H34 1_555 1_555 1_555 119.0(10) no
C34 C35 C36 1_555 1_555 1_555 120.6(3) no
C34 C35 H35 1_555 1_555 1_555 118(2) no
C36 C35 H35 1_555 1_555 1_555 121(2) no
C35 C36 C37 1_555 1_555 1_555 119.7(3) no
C35 C36 H36 1_555 1_555 1_555 118.0(10) no
C37 C36 H36 1_555 1_555 1_555 121.0(10) no
C36 C37 C38 1_555 1_555 1_555 120.1(3) no
C36 C37 H37 1_555 1_555 1_555 120.0(10) no
C38 C37 H37 1_555 1_555 1_555 119.0(10) no
C33 C38 C37 1_555 1_555 1_555 120.8(2) no
C33 C38 H38 1_555 1_555 1_555 120.0(10) no
C37 C38 H38 1_555 1_555 1_555 118.0(10) 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 C18 . . 1.722(2) yes
Cl2 C17 . . 1.720(3) yes
Cl3 C16 . . 1.718(2) yes
Cl4 C15 . . 1.725(2) yes
O5 C13 . . 1.208(2) yes
O6 C13 . . 1.312(2) yes
O6 H6 . . .93(4) no
O7 C20 . . 1.294(2) yes
O7 H7 . . 1.03(4) no
O8 C20 . . 1.210(2) yes
O9 C21 . . 1.249(3) yes
O10 C30 . . 1.265(3) yes
N11 C21 . . 1.313(3) yes
N11 H11A . . .81(3) no
N11 H11B . . .89(4) no
N12 C30 . . 1.306(3) yes
N12 H12A . . .88(3) no
N12 H12B . . .88(3) no
C13 C14 . . 1.511(3) no
C14 C15 . . 1.389(3) no
C14 C19 . . 1.397(3) no
C15 C16 . . 1.397(3) no
C16 C17 . . 1.389(3) no
C17 C18 . . 1.393(3) no
C18 C19 . . 1.389(3) no
C19 C20 . . 1.511(3) no
C21 C22 . . 1.472(4) yes
C22 C23 . . 1.311(3) yes
C22 H22 . . .94(3) no
C23 C24 . . 1.477(4) no
C23 H23 . . .99(3) no
C24 C25 . . 1.383(3) no
C24 C29 . . 1.385(3) no
C25 C26 . . 1.379(4) no
C25 H25 . . .95(3) no
C26 C27 . . 1.369(4) no
C26 H26 . . .93(3) no
C27 C28 . . 1.375(4) no
C27 H27 . . .94(3) no
C28 C29 . . 1.385(4) no
C28 H28 . . .87(3) no
C29 H29 . . .97(3) no
C30 C31 . . 1.467(3) yes
C31 C32 . . 1.326(3) yes
C31 H31 . . .98(3) no
C32 C33 . . 1.465(3) no
C32 H32 . . 1.01(2) no
C33 C34 . . 1.390(3) no
C33 C38 . . 1.378(3) no
C34 C35 . . 1.379(4) no
C34 H34 . . .94(3) no
C35 C36 . . 1.381(5) no
C35 H35 . . .98(3) no
C36 C37 . . 1.363(4) no
C36 H36 . . 1.01(4) no
C37 C38 . . 1.388(4) no
C37 H37 . . .92(3) no
C38 H38 . . .92(2) 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
O6 H6 O9 . .93(4) 1.68(4) 2.575(3) 163(3)
O7 H7 O10 . 1.03(4) 1.43(4) 2.444(2) 167(4)
N11 H11A O5 . .81(3) 2.15(3) 2.949(3) 169(3)
N11 H11B O7 2_656 .89(4) 2.23(4) 3.120(3) 177(3)
N12 H12A O8 . .88(3) 1.97(3) 2.835(3) 166(2)
N12 H12B O9 2_555 .88(3) 2.14(3) 3.001(2) 167(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652311
