#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/03/2230316.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_2230316
loop_
_publ_author_name
'Subashini, Ashokkumar'
'Ramamurthi, Kandasamy'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 N,N'-Bis(4-chlorobenzylidene)-3,3'-dimethoxybiphenyl-4,4'-diamine
;
_journal_coeditor_code           FL2345
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1296
_journal_page_last               o1297
_journal_paper_doi               10.1107/S1600536811015467
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C28 H22 Cl2 N2 O2'
_chemical_formula_moiety         'C28 H22 Cl2 N2 O2'
_chemical_formula_sum            'C28 H22 Cl2 N2 O2'
_chemical_formula_weight         489.38
_chemical_name_systematic
;
N,N'-Bis(4-chlorobenzylidene)-3,3'-dimethoxybiphenyl-4,4'-
diamine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.810(4)
_cell_angle_beta                 80.326(4)
_cell_angle_gamma                79.288(4)
_cell_formula_units_Z            4
_cell_length_a                   9.2358(5)
_cell_length_b                   11.8559(6)
_cell_length_c                   23.5218(12)
_cell_measurement_reflns_used    16478
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      1.79
_cell_volume                     2433.1(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2009)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2009)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publcif (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            29251
_diffrn_reflns_theta_full        25.64
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULscanABS in PLATON; Spek, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         9183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0607P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                5705
_reflns_number_total             9183
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2345.cif
_cod_data_source_block           I
_cod_database_code               2230316
_cod_database_fobs_code          2230316
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_type_symbol
_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
Cl Cl1 -0.16693(10) 0.73278(7) -0.42605(3) 0.0557(3) Uani . . 1.000
Cl Cl2 0.76750(12) 0.00726(7) 0.47655(4) 0.0700(3) Uani . . 1.000
O O1 0.1449(2) 0.70175(15) -0.09211(8) 0.0440(7) Uani . . 1.000
O O2 0.2304(2) 0.10960(15) 0.19381(8) 0.0423(6) Uani . . 1.000
N N1 0.0777(3) 0.57226(18) -0.15956(9) 0.0379(7) Uani . . 1.000
N N2 0.4364(3) 0.19921(19) 0.22848(9) 0.0399(8) Uani . . 1.000
C C1 -0.1290(3) 0.6770(2) -0.35318(11) 0.0402(9) Uani . . 1.000
C C2 -0.2099(4) 0.5962(3) -0.31557(13) 0.0497(11) Uani . . 1.000
C C3 -0.1785(3) 0.5547(3) -0.25790(13) 0.0478(10) Uani . . 1.000
C C4 -0.0646(3) 0.5919(2) -0.23855(11) 0.0393(9) Uani . . 1.000
C C5 0.0142(3) 0.6737(2) -0.27775(12) 0.0461(10) Uani . . 1.000
C C6 -0.0169(3) 0.7171(2) -0.33514(12) 0.0473(10) Uani . . 1.000
C C7 -0.0298(3) 0.5443(2) -0.17770(12) 0.0425(9) Uani . . 1.000
C C8 0.1164(3) 0.5157(2) -0.10280(11) 0.0348(8) Uani . . 1.000
C C9 0.1611(3) 0.5830(2) -0.06896(11) 0.0352(8) Uani . . 1.000
C C10 0.2146(3) 0.5283(2) -0.01568(11) 0.0361(9) Uani . . 1.000
C C11 0.2278(3) 0.4060(2) 0.00542(11) 0.0352(8) Uani . . 1.000
C C12 0.1835(3) 0.3401(2) -0.02828(11) 0.0395(9) Uani . . 1.000
C C13 0.1285(3) 0.3946(2) -0.08133(11) 0.0398(9) Uani . . 1.000
C C14 0.2887(3) 0.3500(2) 0.06174(11) 0.0352(8) Uani . . 1.000
C C15 0.4010(3) 0.3933(2) 0.07895(12) 0.0447(9) Uani . . 1.000
C C16 0.4541(3) 0.3410(2) 0.13245(12) 0.0454(10) Uani . . 1.000
C C17 0.3966(3) 0.2461(2) 0.17100(11) 0.0378(9) Uani . . 1.000
C C18 0.2828(3) 0.2025(2) 0.15388(11) 0.0359(8) Uani . . 1.000
C C19 0.2320(3) 0.2536(2) 0.09986(11) 0.0359(8) Uani . . 1.000
C C20 0.5723(4) 0.1773(2) 0.23557(12) 0.0470(10) Uani . . 1.000
C C21 0.6195(3) 0.1368(2) 0.29511(12) 0.0409(9) Uani . . 1.000
C C22 0.7661(3) 0.0873(3) 0.30185(14) 0.0519(11) Uani . . 1.000
C C23 0.8113(4) 0.0469(2) 0.35752(15) 0.0529(11) Uani . . 1.000
C C24 0.7101(4) 0.0574(2) 0.40639(13) 0.0466(10) Uani . . 1.000
C C25 0.5640(3) 0.1055(2) 0.40128(12) 0.0449(10) Uani . . 1.000
C C26 0.5199(3) 0.1443(2) 0.34562(12) 0.0417(9) Uani . . 1.000
C C27 0.1841(4) 0.7738(2) -0.05816(14) 0.0552(10) Uani . . 1.000
C C28 0.1111(3) 0.0658(3) 0.17929(13) 0.0509(10) Uani . . 1.000
Cl Cl3 0.72546(11) 0.22366(9) 0.91179(4) 0.0780(4) Uani . . 1.000
Cl Cl4 -0.40375(15) 0.99270(9) 0.05465(5) 0.1072(5) Uani . . 1.000
O O3 0.4123(2) 0.30306(14) 0.58097(8) 0.0405(6) Uani . . 1.000
O O4 0.1571(2) 0.91381(15) 0.32380(8) 0.0416(6) Uani . . 1.000
N N3 0.4599(3) 0.43315(19) 0.65042(9) 0.0392(8) Uani . . 1.000
N N4 -0.0211(3) 0.79885(18) 0.28786(9) 0.0371(7) Uani . . 1.000
C C29 0.6336(3) 0.2908(3) 0.85004(12) 0.0470(10) Uani . . 1.000
C C30 0.5040(3) 0.3671(3) 0.85675(12) 0.0533(11) Uani . . 1.000
C C31 0.4329(3) 0.4206(3) 0.80728(12) 0.0509(10) Uani . . 1.000
C C32 0.4907(3) 0.3992(2) 0.75239(11) 0.0373(9) Uani . . 1.000
C C33 0.6227(3) 0.3212(2) 0.74676(12) 0.0411(9) Uani . . 1.000
C C34 0.6943(3) 0.2663(3) 0.79566(13) 0.0490(10) Uani . . 1.000
C C35 0.4114(3) 0.4551(2) 0.70078(12) 0.0413(9) Uani . . 1.000
C C36 0.3826(3) 0.4902(2) 0.60174(10) 0.0338(8) Uani . . 1.000
C C37 0.3332(3) 0.6105(2) 0.58768(11) 0.0415(9) Uani . . 1.000
C C38 0.2646(3) 0.6615(2) 0.53740(11) 0.0410(9) Uani . . 1.000
C C39 0.2441(3) 0.5941(2) 0.49943(10) 0.0330(8) Uani . . 1.000
C C40 0.2939(3) 0.4727(2) 0.51341(10) 0.0331(8) Uani . . 1.000
C C41 0.3628(3) 0.4211(2) 0.56359(11) 0.0329(8) Uani . . 1.000
C C42 0.1699(3) 0.6476(2) 0.44576(10) 0.0324(8) Uani . . 1.000
C C43 0.0753(3) 0.5893(2) 0.42723(11) 0.0371(8) Uani . . 1.000
C C44 0.0071(3) 0.6402(2) 0.37685(11) 0.0363(8) Uani . . 1.000
C C45 0.0340(3) 0.7494(2) 0.34255(10) 0.0333(8) Uani . . 1.000
C C46 0.1313(3) 0.8083(2) 0.36068(11) 0.0332(8) Uani . . 1.000
C C47 0.1964(3) 0.7585(2) 0.41185(10) 0.0333(8) Uani . . 1.000
C C48 -0.1580(3) 0.7995(2) 0.28454(12) 0.0419(9) Uani . . 1.000
C C49 -0.2182(3) 0.8436(2) 0.22789(13) 0.0410(9) Uani . . 1.000
C C50 -0.3700(4) 0.8773(3) 0.22698(16) 0.0584(12) Uani . . 1.000
C C51 -0.4283(4) 0.9242(3) 0.17360(19) 0.0694(14) Uani . . 1.000
C C52 -0.3328(5) 0.9342(3) 0.12174(17) 0.0634(13) Uani . . 1.000
C C53 -0.1824(4) 0.8986(3) 0.12114(14) 0.0577(13) Uani . . 1.000
C C54 -0.1256(4) 0.8540(2) 0.17442(12) 0.0464(10) Uani . . 1.000
C C55 0.3890(4) 0.2297(2) 0.54500(13) 0.0507(10) Uani . . 1.000
C C56 0.2591(4) 0.9755(2) 0.33901(13) 0.0493(10) Uani . . 1.000
H H2 -0.28600 0.56920 -0.32890 0.0600 Uiso calc R 1.000
H H3 -0.23530 0.50020 -0.23120 0.0570 Uiso calc R 1.000
H H5 0.09120 0.70050 -0.26490 0.0550 Uiso calc R 1.000
H H6 0.03760 0.77340 -0.36170 0.0570 Uiso calc R 1.000
H H7 -0.08930 0.49140 -0.15130 0.0510 Uiso calc R 1.000
H H10 0.24300 0.57480 0.00700 0.0430 Uiso calc R 1.000
H H12 0.19100 0.25710 -0.01490 0.0470 Uiso calc R 1.000
H H13 0.09830 0.34790 -0.10350 0.0480 Uiso calc R 1.000
H H15 0.44130 0.45910 0.05390 0.0540 Uiso calc R 1.000
H H16 0.53190 0.37090 0.14310 0.0540 Uiso calc R 1.000
H H19 0.15660 0.22220 0.08850 0.0430 Uiso calc R 1.000
H H20 0.64560 0.18710 0.20190 0.0570 Uiso calc R 1.000
H H22 0.83620 0.08100 0.26780 0.0620 Uiso calc R 1.000
H H23 0.91140 0.01230 0.36170 0.0630 Uiso calc R 1.000
H H25 0.49460 0.11180 0.43550 0.0540 Uiso calc R 1.000
H H26 0.41900 0.17690 0.34190 0.0500 Uiso calc R 1.000
H H27A 0.28880 0.74970 -0.05210 0.0830 Uiso calc R 1.000
H H27B 0.12170 0.76480 -0.01980 0.0830 Uiso calc R 1.000
H H27C 0.16880 0.85640 -0.07940 0.0830 Uiso calc R 1.000
H H28A 0.14360 0.03600 0.14310 0.0760 Uiso calc R 1.000
H H28B 0.02690 0.12930 0.17300 0.0760 Uiso calc R 1.000
H H28C 0.08070 0.00190 0.21180 0.0760 Uiso calc R 1.000
H H30 0.46380 0.38300 0.89440 0.0640 Uiso calc R 1.000
H H31 0.34250 0.47300 0.81140 0.0610 Uiso calc R 1.000
H H33 0.66370 0.30580 0.70910 0.0490 Uiso calc R 1.000
H H34 0.78360 0.21250 0.79200 0.0590 Uiso calc R 1.000
H H35 0.32230 0.50870 0.70540 0.0500 Uiso calc R 1.000
H H37 0.34660 0.65840 0.61280 0.0500 Uiso calc R 1.000
H H38 0.23110 0.74380 0.52870 0.0490 Uiso calc R 1.000
H H40 0.28020 0.42500 0.48820 0.0400 Uiso calc R 1.000
H H43 0.05700 0.51360 0.44940 0.0450 Uiso calc R 1.000
H H44 -0.05920 0.59960 0.36560 0.0440 Uiso calc R 1.000
H H47 0.25980 0.80010 0.42410 0.0400 Uiso calc R 1.000
H H48 -0.22170 0.77090 0.31920 0.0500 Uiso calc R 1.000
H H50 -0.43510 0.86850 0.26310 0.0700 Uiso calc R 1.000
H H51 -0.53210 0.94880 0.17320 0.0830 Uiso calc R 1.000
H H53 -0.11830 0.90450 0.08480 0.0690 Uiso calc R 1.000
H H54 -0.02160 0.83010 0.17440 0.0560 Uiso calc R 1.000
H H55A 0.43770 0.25550 0.50470 0.0760 Uiso calc R 1.000
H H55B 0.28220 0.23480 0.54430 0.0760 Uiso calc R 1.000
H H55C 0.43100 0.14810 0.56120 0.0760 Uiso calc R 1.000
H H56A 0.35490 0.92420 0.34290 0.0740 Uiso calc R 1.000
H H56B 0.21950 0.99830 0.37660 0.0740 Uiso calc R 1.000
H H56C 0.27280 1.04610 0.30790 0.0740 Uiso calc R 1.000
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
C9 O1 C27 . . . 117.1(2) no
C18 O2 C28 . . . 117.0(2) no
C41 O3 C55 . . . 116.9(2) no
C46 O4 C56 . . . 117.7(2) no
C7 N1 C8 . . . 119.7(2) no
C17 N2 C20 . . . 119.2(2) no
C35 N3 C36 . . . 119.7(2) no
C45 N4 C48 . . . 119.0(2) no
Cl1 C1 C6 . . . 118.0(2) no
C2 C1 C6 . . . 121.8(3) no
Cl1 C1 C2 . . . 120.2(2) no
C1 C2 C3 . . . 118.9(3) no
C2 C3 C4 . . . 120.8(3) no
C3 C4 C5 . . . 118.6(2) no
C3 C4 C7 . . . 120.1(2) no
C5 C4 C7 . . . 121.3(2) no
C4 C5 C6 . . . 121.4(3) no
C1 C6 C5 . . . 118.6(2) no
N1 C7 C4 . . . 121.6(2) no
N1 C8 C9 . . . 118.5(2) no
N1 C8 C13 . . . 123.1(2) no
C9 C8 C13 . . . 118.1(2) no
C8 C9 C10 . . . 120.1(2) no
O1 C9 C8 . . . 115.3(2) no
O1 C9 C10 . . . 124.6(2) no
C9 C10 C11 . . . 121.5(2) no
C10 C11 C12 . . . 118.1(2) no
C10 C11 C14 . . . 120.2(2) no
C12 C11 C14 . . . 121.7(2) no
C11 C12 C13 . . . 120.6(2) no
C8 C13 C12 . . . 121.7(2) no
C11 C14 C19 . . . 120.5(2) no
C15 C14 C19 . . . 118.1(2) no
C11 C14 C15 . . . 121.4(2) no
C14 C15 C16 . . . 120.4(2) no
C15 C16 C17 . . . 121.8(3) no
N2 C17 C18 . . . 118.6(2) no
C16 C17 C18 . . . 118.0(2) no
N2 C17 C16 . . . 123.2(2) no
C17 C18 C19 . . . 120.0(2) no
O2 C18 C19 . . . 124.8(2) no
O2 C18 C17 . . . 115.2(2) no
C14 C19 C18 . . . 121.7(3) no
N2 C20 C21 . . . 121.4(3) no
C20 C21 C22 . . . 120.3(3) no
C20 C21 C26 . . . 121.6(3) no
C22 C21 C26 . . . 118.1(3) no
C21 C22 C23 . . . 120.9(3) no
C22 C23 C24 . . . 119.3(3) no
Cl2 C24 C25 . . . 119.5(2) no
C23 C24 C25 . . . 121.3(3) no
Cl2 C24 C23 . . . 119.2(3) no
C24 C25 C26 . . . 118.9(3) no
C21 C26 C25 . . . 121.5(3) no
C3 C2 H2 . . . 121.00 no
C1 C2 H2 . . . 121.00 no
C4 C3 H3 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C5 H5 . . . 119.00 no
C6 C5 H5 . . . 119.00 no
C1 C6 H6 . . . 121.00 no
C5 C6 H6 . . . 121.00 no
N1 C7 H7 . . . 119.00 no
C4 C7 H7 . . . 119.00 no
C11 C10 H10 . . . 119.00 no
C9 C10 H10 . . . 119.00 no
C11 C12 H12 . . . 120.00 no
C13 C12 H12 . . . 120.00 no
C12 C13 H13 . . . 119.00 no
C8 C13 H13 . . . 119.00 no
C14 C15 H15 . . . 120.00 no
C16 C15 H15 . . . 120.00 no
C17 C16 H16 . . . 119.00 no
C15 C16 H16 . . . 119.00 no
C14 C19 H19 . . . 119.00 no
C18 C19 H19 . . . 119.00 no
N2 C20 H20 . . . 119.00 no
C21 C20 H20 . . . 119.00 no
C21 C22 H22 . . . 120.00 no
C23 C22 H22 . . . 120.00 no
C24 C23 H23 . . . 120.00 no
C22 C23 H23 . . . 120.00 no
C24 C25 H25 . . . 121.00 no
C26 C25 H25 . . . 121.00 no
C25 C26 H26 . . . 119.00 no
C21 C26 H26 . . . 119.00 no
O1 C27 H27B . . . 110.00 no
O1 C27 H27C . . . 109.00 no
H27A C27 H27B . . . 110.00 no
H27A C27 H27C . . . 109.00 no
O1 C27 H27A . . . 109.00 no
H27B C27 H27C . . . 109.00 no
H28A C28 H28C . . . 109.00 no
H28B C28 H28C . . . 109.00 no
H28A C28 H28B . . . 110.00 no
O2 C28 H28A . . . 109.00 no
O2 C28 H28B . . . 109.00 no
O2 C28 H28C . . . 109.00 no
Cl3 C29 C30 . . . 119.1(2) no
Cl3 C29 C34 . . . 119.2(2) no
C30 C29 C34 . . . 121.8(3) no
C29 C30 C31 . . . 118.5(3) no
C30 C31 C32 . . . 121.4(3) no
C31 C32 C33 . . . 119.0(3) no
C31 C32 C35 . . . 120.3(2) no
C33 C32 C35 . . . 120.6(2) no
C32 C33 C34 . . . 120.4(3) no
C29 C34 C33 . . . 119.0(3) no
N3 C35 C32 . . . 121.2(2) no
N3 C36 C37 . . . 123.9(2) no
N3 C36 C41 . . . 117.4(2) no
C37 C36 C41 . . . 118.6(2) no
C36 C37 C38 . . . 120.8(2) no
C37 C38 C39 . . . 121.1(2) no
C38 C39 C40 . . . 118.3(2) no
C38 C39 C42 . . . 121.6(2) no
C40 C39 C42 . . . 120.2(2) no
C39 C40 C41 . . . 120.9(2) no
O3 C41 C36 . . . 115.1(2) no
O3 C41 C40 . . . 124.6(2) no
C36 C41 C40 . . . 120.3(2) no
C39 C42 C43 . . . 121.5(2) no
C39 C42 C47 . . . 120.1(2) no
C43 C42 C47 . . . 118.4(2) no
C42 C43 C44 . . . 120.9(2) no
C43 C44 C45 . . . 121.2(2) no
N4 C45 C44 . . . 122.9(2) no
N4 C45 C46 . . . 118.6(2) no
C44 C45 C46 . . . 118.2(2) no
O4 C46 C45 . . . 115.3(2) no
O4 C46 C47 . . . 124.3(2) no
C45 C46 C47 . . . 120.5(2) no
C42 C47 C46 . . . 120.9(2) no
N4 C48 C49 . . . 120.9(2) no
C48 C49 C50 . . . 120.1(3) no
C48 C49 C54 . . . 121.3(3) no
C50 C49 C54 . . . 118.6(3) no
C49 C50 C51 . . . 120.8(3) no
C50 C51 C52 . . . 118.8(4) no
Cl4 C52 C51 . . . 119.4(3) no
Cl4 C52 C53 . . . 118.9(3) no
C51 C52 C53 . . . 121.8(4) no
C52 C53 C54 . . . 118.9(3) no
C49 C54 C53 . . . 121.1(3) no
C29 C30 H30 . . . 121.00 no
C31 C30 H30 . . . 121.00 no
C30 C31 H31 . . . 119.00 no
C32 C31 H31 . . . 119.00 no
C32 C33 H33 . . . 120.00 no
C34 C33 H33 . . . 120.00 no
C29 C34 H34 . . . 121.00 no
C33 C34 H34 . . . 121.00 no
N3 C35 H35 . . . 119.00 no
C32 C35 H35 . . . 119.00 no
C36 C37 H37 . . . 120.00 no
C38 C37 H37 . . . 120.00 no
C37 C38 H38 . . . 120.00 no
C39 C38 H38 . . . 119.00 no
C39 C40 H40 . . . 120.00 no
C41 C40 H40 . . . 120.00 no
C42 C43 H43 . . . 120.00 no
C44 C43 H43 . . . 120.00 no
C43 C44 H44 . . . 119.00 no
C45 C44 H44 . . . 119.00 no
C42 C47 H47 . . . 120.00 no
C46 C47 H47 . . . 120.00 no
N4 C48 H48 . . . 120.00 no
C49 C48 H48 . . . 120.00 no
C49 C50 H50 . . . 120.00 no
C51 C50 H50 . . . 120.00 no
C50 C51 H51 . . . 121.00 no
C52 C51 H51 . . . 121.00 no
C52 C53 H53 . . . 121.00 no
C54 C53 H53 . . . 120.00 no
C49 C54 H54 . . . 119.00 no
C53 C54 H54 . . . 119.00 no
O3 C55 H55A . . . 109.00 no
O3 C55 H55B . . . 109.00 no
O3 C55 H55C . . . 109.00 no
H55A C55 H55B . . . 109.00 no
H55A C55 H55C . . . 110.00 no
H55B C55 H55C . . . 109.00 no
O4 C56 H56A . . . 109.00 no
O4 C56 H56B . . . 109.00 no
O4 C56 H56C . . . 109.00 no
H56A C56 H56B . . . 110.00 no
H56A C56 H56C . . . 109.00 no
H56B C56 H56C . . . 110.00 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 C1 . . 1.749(3) no
Cl2 C24 . . 1.748(3) no
Cl3 C29 . . 1.749(3) no
Cl4 C52 . . 1.744(4) no
O1 C9 . . 1.369(3) no
O1 C27 . . 1.430(3) no
O2 C28 . . 1.424(4) no
O2 C18 . . 1.367(3) no
O3 C41 . . 1.371(3) no
O3 C55 . . 1.418(3) no
O4 C46 . . 1.372(3) no
O4 C56 . . 1.431(4) no
N1 C7 . . 1.270(4) no
N1 C8 . . 1.412(3) no
N2 C17 . . 1.412(3) no
N2 C20 . . 1.264(5) no
N3 C35 . . 1.265(3) no
N3 C36 . . 1.412(3) no
N4 C45 . . 1.413(3) no
N4 C48 . . 1.278(4) no
C1 C2 . . 1.374(4) no
C1 C6 . . 1.381(4) no
C2 C3 . . 1.385(4) no
C3 C4 . . 1.393(4) no
C4 C7 . . 1.470(4) no
C4 C5 . . 1.385(4) no
C5 C6 . . 1.380(4) no
C8 C9 . . 1.409(4) no
C8 C13 . . 1.390(3) no
C9 C10 . . 1.388(4) no
C10 C11 . . 1.402(3) no
C11 C14 . . 1.481(4) no
C11 C12 . . 1.392(4) no
C12 C13 . . 1.389(4) no
C14 C15 . . 1.394(4) no
C14 C19 . . 1.395(4) no
C15 C16 . . 1.386(4) no
C16 C17 . . 1.389(4) no
C17 C18 . . 1.407(4) no
C18 C19 . . 1.385(4) no
C20 C21 . . 1.476(4) no
C21 C22 . . 1.391(4) no
C21 C26 . . 1.386(4) no
C22 C23 . . 1.386(5) no
C23 C24 . . 1.370(5) no
C24 C25 . . 1.377(5) no
C25 C26 . . 1.381(4) no
C2 H2 . . 0.9500 no
C3 H3 . . 0.9500 no
C5 H5 . . 0.9500 no
C6 H6 . . 0.9500 no
C7 H7 . . 0.9500 no
C10 H10 . . 0.9500 no
C12 H12 . . 0.9500 no
C13 H13 . . 0.9500 no
C15 H15 . . 0.9500 no
C16 H16 . . 0.9500 no
C19 H19 . . 0.9500 no
C20 H20 . . 0.9500 no
C22 H22 . . 0.9500 no
C23 H23 . . 0.9500 no
C25 H25 . . 0.9500 no
C26 H26 . . 0.9500 no
C27 H27C . . 0.9800 no
C27 H27B . . 0.9800 no
C27 H27A . . 0.9800 no
C28 H28A . . 0.9800 no
C28 H28B . . 0.9800 no
C28 H28C . . 0.9800 no
C29 C30 . . 1.371(5) no
C29 C34 . . 1.384(4) no
C30 C31 . . 1.388(4) no
C31 C32 . . 1.377(4) no
C32 C33 . . 1.395(4) no
C32 C35 . . 1.474(4) no
C33 C34 . . 1.383(4) no
C36 C37 . . 1.389(3) no
C36 C41 . . 1.408(3) no
C37 C38 . . 1.387(4) no
C38 C39 . . 1.391(3) no
C39 C40 . . 1.401(3) no
C39 C42 . . 1.484(3) no
C40 C41 . . 1.388(4) no
C42 C43 . . 1.390(4) no
C42 C47 . . 1.402(3) no
C43 C44 . . 1.387(4) no
C44 C45 . . 1.389(3) no
C45 C46 . . 1.409(4) no
C46 C47 . . 1.386(4) no
C48 C49 . . 1.469(4) no
C49 C50 . . 1.387(5) no
C49 C54 . . 1.389(4) no
C50 C51 . . 1.396(6) no
C51 C52 . . 1.374(6) no
C52 C53 . . 1.373(6) no
C53 C54 . . 1.385(4) no
C30 H30 . . 0.9500 no
C31 H31 . . 0.9500 no
C33 H33 . . 0.9500 no
C34 H34 . . 0.9500 no
C35 H35 . . 0.9500 no
C37 H37 . . 0.9500 no
C38 H38 . . 0.9500 no
C40 H40 . . 0.9500 no
C43 H43 . . 0.9500 no
C44 H44 . . 0.9500 no
C47 H47 . . 0.9500 no
C48 H48 . . 0.9500 no
C50 H50 . . 0.9500 no
C51 H51 . . 0.9500 no
C53 H53 . . 0.9500 no
C54 H54 . . 0.9500 no
C55 H55A . . 0.9800 no
C55 H55B . . 0.9800 no
C55 H55C . . 0.9800 no
C56 H56A . . 0.9800 no
C56 H56B . . 0.9800 no
C56 H56C . . 0.9800 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 Cl2 3.5048(12) . 1_464 no
Cl4 Cl4 3.3173(18) . 2_475 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
_geom_hbond_publ_flag
C23 H23 O4 1_645 0.95 2.48 3.348(4) 152 yes
C31 H31 N1 1_556 0.95 2.57 3.498(4) 166 yes
C3 H3 Cg5 1_454 0.95 2.75 3.642(3) 156 yes
C30 H30 Cg2 1_556 0.95 2.90 3.641(3) 136 yes
C33 H33 Cg7 2_666 0.95 2.97 3.850(3) 154 yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C27 O1 C9 C8 . . . . 177.9(3) no
C27 O1 C9 C10 . . . . -1.0(4) no
C28 O2 C18 C17 . . . . 177.6(2) no
C28 O2 C18 C19 . . . . -2.5(4) no
C55 O3 C41 C40 . . . . -0.8(4) no
C55 O3 C41 C36 . . . . 177.5(2) no
C56 O4 C46 C47 . . . . 0.7(4) no
C56 O4 C46 C45 . . . . -177.9(2) no
C8 N1 C7 C4 . . . . -173.7(2) no
C7 N1 C8 C13 . . . . 45.5(4) no
C7 N1 C8 C9 . . . . -141.9(3) no
C20 N2 C17 C18 . . . . 138.2(3) no
C17 N2 C20 C21 . . . . 175.3(2) no
C20 N2 C17 C16 . . . . -48.2(4) no
C35 N3 C36 C41 . . . . -136.3(3) no
C36 N3 C35 C32 . . . . -178.7(2) no
C35 N3 C36 C37 . . . . 47.5(4) no
C45 N4 C48 C49 . . . . -176.4(2) no
C48 N4 C45 C46 . . . . -137.8(3) no
C48 N4 C45 C44 . . . . 48.1(4) no
C2 C1 C6 C5 . . . . 0.4(4) no
Cl1 C1 C2 C3 . . . . -179.2(3) no
Cl1 C1 C6 C5 . . . . -180.0(2) no
C6 C1 C2 C3 . . . . 0.5(5) no
C1 C2 C3 C4 . . . . -1.5(5) no
C2 C3 C4 C5 . . . . 1.7(5) no
C2 C3 C4 C7 . . . . -178.2(3) no
C3 C4 C5 C6 . . . . -0.8(4) no
C5 C4 C7 N1 . . . . -3.2(4) no
C7 C4 C5 C6 . . . . 179.0(2) no
C3 C4 C7 N1 . . . . 176.7(3) no
C4 C5 C6 C1 . . . . -0.2(4) no
C13 C8 C9 O1 . . . . -179.3(2) no
N1 C8 C9 O1 . . . . 7.7(4) no
N1 C8 C9 C10 . . . . -173.3(3) no
C9 C8 C13 C12 . . . . -0.3(4) no
C13 C8 C9 C10 . . . . -0.4(4) no
N1 C8 C13 C12 . . . . 172.3(3) no
C8 C9 C10 C11 . . . . 1.0(4) no
O1 C9 C10 C11 . . . . 179.8(3) no
C9 C10 C11 C12 . . . . -0.9(4) no
C9 C10 C11 C14 . . . . 178.5(3) no
C10 C11 C12 C13 . . . . 0.3(4) no
C10 C11 C14 C15 . . . . -34.9(4) no
C10 C11 C14 C19 . . . . 143.5(3) no
C12 C11 C14 C15 . . . . 144.5(3) no
C12 C11 C14 C19 . . . . -37.1(4) no
C14 C11 C12 C13 . . . . -179.2(3) no
C11 C12 C13 C8 . . . . 0.4(4) no
C11 C14 C15 C16 . . . . 178.6(2) no
C15 C14 C19 C18 . . . . 1.1(4) no
C11 C14 C19 C18 . . . . -177.4(2) no
C19 C14 C15 C16 . . . . 0.2(4) no
C14 C15 C16 C17 . . . . -1.2(4) no
C15 C16 C17 C18 . . . . 0.9(4) no
C15 C16 C17 N2 . . . . -172.7(2) no
N2 C17 C18 O2 . . . . -5.7(3) no
N2 C17 C18 C19 . . . . 174.3(2) no
C16 C17 C18 O2 . . . . -179.7(2) no
C16 C17 C18 C19 . . . . 0.4(4) no
C17 C18 C19 C14 . . . . -1.4(4) no
O2 C18 C19 C14 . . . . 178.7(2) no
N2 C20 C21 C22 . . . . 164.9(3) no
N2 C20 C21 C26 . . . . -13.7(4) no
C26 C21 C22 C23 . . . . -0.2(4) no
C20 C21 C22 C23 . . . . -178.8(3) no
C22 C21 C26 C25 . . . . 0.9(4) no
C20 C21 C26 C25 . . . . 179.5(2) no
C21 C22 C23 C24 . . . . -0.8(5) no
C22 C23 C24 C25 . . . . 1.1(4) no
C22 C23 C24 Cl2 . . . . -179.6(2) no
Cl2 C24 C25 C26 . . . . -179.7(2) no
C23 C24 C25 C26 . . . . -0.4(4) no
C24 C25 C26 C21 . . . . -0.6(4) no
Cl3 C29 C30 C31 . . . . 179.4(3) no
C34 C29 C30 C31 . . . . 0.0(5) no
Cl3 C29 C34 C33 . . . . -178.9(2) no
C30 C29 C34 C33 . . . . 0.6(5) no
C29 C30 C31 C32 . . . . -0.6(5) no
C30 C31 C32 C33 . . . . 0.6(4) no
C30 C31 C32 C35 . . . . 178.7(3) no
C31 C32 C33 C34 . . . . 0.0(4) no
C35 C32 C33 C34 . . . . -178.1(3) no
C31 C32 C35 N3 . . . . -177.4(3) no
C33 C32 C35 N3 . . . . 0.7(4) no
C32 C33 C34 C29 . . . . -0.6(4) no
N3 C36 C37 C38 . . . . 176.7(3) no
C41 C36 C37 C38 . . . . 0.6(4) no
N3 C36 C41 O3 . . . . 4.6(4) no
N3 C36 C41 C40 . . . . -177.0(3) no
C37 C36 C41 O3 . . . . -179.0(2) no
C37 C36 C41 C40 . . . . -0.6(4) no
C36 C37 C38 C39 . . . . -0.4(4) no
C37 C38 C39 C40 . . . . 0.4(4) no
C37 C38 C39 C42 . . . . 179.6(3) no
C38 C39 C40 C41 . . . . -0.4(4) no
C42 C39 C40 C41 . . . . -179.7(3) no
C38 C39 C42 C43 . . . . -142.5(3) no
C38 C39 C42 C47 . . . . 38.6(4) no
C40 C39 C42 C43 . . . . 36.7(4) no
C40 C39 C42 C47 . . . . -142.2(3) no
C39 C40 C41 O3 . . . . 178.8(2) no
C39 C40 C41 C36 . . . . 0.6(4) no
C39 C42 C43 C44 . . . . -179.8(2) no
C47 C42 C43 C44 . . . . -0.9(4) no
C39 C42 C47 C46 . . . . 178.2(2) no
C43 C42 C47 C46 . . . . -0.8(4) no
C42 C43 C44 C45 . . . . 1.7(4) no
C43 C44 C45 N4 . . . . 173.4(2) no
C43 C44 C45 C46 . . . . -0.8(4) no
N4 C45 C46 O4 . . . . 3.4(3) no
N4 C45 C46 C47 . . . . -175.3(2) no
C44 C45 C46 O4 . . . . 177.9(2) no
C44 C45 C46 C47 . . . . -0.8(4) no
O4 C46 C47 C42 . . . . -176.9(2) no
C45 C46 C47 C42 . . . . 1.6(4) no
N4 C48 C49 C50 . . . . -160.4(3) no
N4 C48 C49 C54 . . . . 18.7(4) no
C48 C49 C50 C51 . . . . 177.2(3) no
C54 C49 C50 C51 . . . . -2.0(5) no
C48 C49 C54 C53 . . . . -178.2(3) no
C50 C49 C54 C53 . . . . 0.9(4) no
C49 C50 C51 C52 . . . . 1.3(5) no
C50 C51 C52 Cl4 . . . . -180.0(3) no
C50 C51 C52 C53 . . . . 0.5(6) no
Cl4 C52 C53 C54 . . . . 178.9(3) no
C51 C52 C53 C54 . . . . -1.5(5) no
C52 C53 C54 C49 . . . . 0.8(5) no
