#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229171.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_2229171
loop_
_publ_author_name
'Holakovský, Roman'
'Pojarová, Michaela'
'Dušek, Michal'
'Čejka, Jan'
'Císařová, Ivana'
_publ_section_title
;
 (R)-2,2'-Bis[N'-(3,5-dichlorophenyl)ureido]-1,1'-binaphthalene
 chloroform disolvate
;
_journal_coeditor_code           OM2383
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o384
_journal_page_last               o385
_journal_paper_doi               10.1107/S1600536810052657
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C34 H22 Cl4 N4 O2, 2C H Cl3'
_chemical_formula_moiety         'C34 H22 Cl4 N4 O2, 2(C H Cl3)'
_chemical_formula_sum            'C36 H24 Cl10 N4 O2'
_chemical_formula_weight         899.09
_chemical_name_systematic
;
(R)-2,2'-Bis[N'-(3,5-dichlorophenyl)ureido]-1,1'-binaphthalene
chloroform disolvate
;
_space_group_IT_number           1
_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                96.71(3)
_cell_angle_beta                 110.90(3)
_cell_angle_gamma                103.98(3)
_cell_formula_units_Z            2
_cell_length_a                   11.879(2)
_cell_length_b                   12.445(3)
_cell_length_c                   15.039(3)
_cell_measurement_reflns_used    16629
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      1.73
_cell_volume                     1964.3(10)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       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  0.037
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20566
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.584
_refine_ls_abs_structure_details 'Flack (1983), 7535 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     993
_refine_ls_number_reflns         16629
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0525P)²+1.6951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                13656
_reflns_number_total             16629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2383.cif
_cod_data_source_block           I
_cod_original_cell_volume        1964.4(9)
_cod_database_code               2229171
_cod_database_fobs_code          2229171
loop_
_symmetry_equiv_pos_as_xyz
'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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.26222(7) 0.20014(6) 0.38434(6) 0.04304(19) Uani d . 1 . .
Cl Cl2 -0.18934(8) 0.26670(8) 0.31225(7) 0.0613(2) Uani d . 1 . .
Cl Cl3 0.19698(7) 0.50494(6) 0.49404(5) 0.04183(18) Uani d . 1 . .
Cl Cl4 0.37139(10) 0.95394(8) 0.65451(6) 0.0624(3) Uani d . 1 . .
O O1 0.00094(17) 0.57167(15) 0.16079(14) 0.0331(4) Uani d . 1 . .
O O2 0.35517(17) 0.63877(15) 0.25092(13) 0.0295(4) Uani d . 1 . .
N N1 0.0937(2) 0.57038(19) 0.05171(17) 0.0331(5) Uani d . 1 . .
H H1A 0.1373 0.5364 0.0307 0.040 Uiso calc R 1 . .
N N2 0.0982(2) 0.43829(19) 0.14486(17) 0.0319(5) Uani d . 1 . .
H H2A 0.1398 0.4156 0.1140 0.038 Uiso calc R 1 . .
N N3 0.3489(2) 0.77884(18) 0.16653(15) 0.0269(5) Uani d . 1 . .
H H3A 0.3421 0.8460 0.1661 0.032 Uiso calc R 1 . .
N N4 0.3253(2) 0.80211(18) 0.31075(16) 0.0291(5) Uani d . 1 . .
H H4A 0.3222 0.8683 0.3010 0.035 Uiso calc R 1 . .
C C1 0.1508(2) 0.7245(2) -0.02232(19) 0.0264(6) Uani d . 1 . .
C C2 0.0655(2) 0.6619(2) 0.00973(19) 0.0285(6) Uani d . 1 . .
C C3 -0.0502(3) 0.6840(2) -0.0042(2) 0.0347(7) Uani d . 1 . .
H H3 -0.1056 0.6425 0.0191 0.042 Uiso calc R 1 . .
C C4 -0.0803(3) 0.7666(3) -0.0520(2) 0.0377(7) Uani d . 1 . .
H H4 -0.1563 0.7810 -0.0604 0.045 Uiso calc R 1 . .
C C5 0.0009(3) 0.8303(2) -0.0887(2) 0.0335(7) Uani d . 1 . .
C C6 -0.0311(3) 0.9125(3) -0.1431(2) 0.0417(8) Uani d . 1 . .
H H6 -0.1081 0.9260 -0.1542 0.050 Uiso calc R 1 . .
C C7 0.0474(3) 0.9714(3) -0.1791(2) 0.0447(8) Uani d . 1 . .
H H7 0.0239 1.0241 -0.2151 0.054 Uiso calc R 1 . .
C C8 0.1652(3) 0.9530(2) -0.1621(2) 0.0407(8) Uani d . 1 . .
H H8 0.2194 0.9942 -0.1865 0.049 Uiso calc R 1 . .
C C9 0.2002(3) 0.8757(2) -0.1105(2) 0.0350(7) Uani d . 1 . .
H H9 0.2787 0.8655 -0.0990 0.042 Uiso calc R 1 . .
C C10 0.1188(3) 0.8101(2) -0.07356(19) 0.0291(6) Uani d . 1 . .
C C11 0.0591(2) 0.5303(2) 0.1218(2) 0.0291(6) Uani d . 1 . .
C C12 0.0774(2) 0.3766(2) 0.2139(2) 0.0282(6) Uani d . 1 . .
C C13 -0.0334(3) 0.3594(2) 0.2302(2) 0.0335(6) Uani d . 1 . .
H H13 -0.0941 0.3932 0.1995 0.040 Uiso calc R 1 . .
C C14 -0.0502(3) 0.2912(3) 0.2930(2) 0.0368(7) Uani d . 1 . .
C C15 0.0374(3) 0.2386(3) 0.3409(2) 0.0360(7) Uani d . 1 . .
H H15 0.0235 0.1919 0.3823 0.043 Uiso calc R 1 . .
C C16 0.1472(3) 0.2598(2) 0.3232(2) 0.0310(6) Uani d . 1 . .
C C17 0.1677(2) 0.3270(2) 0.2606(2) 0.0281(6) Uani d . 1 . .
H H17 0.2417 0.3390 0.2499 0.034 Uiso calc R 1 . .
C C18 0.2721(2) 0.6984(2) -0.00653(18) 0.0245(6) Uani d . 1 . .
C C19 0.3648(2) 0.7205(2) 0.08680(19) 0.0277(6) Uani d . 1 . .
C C20 0.4754(2) 0.6888(2) 0.1046(2) 0.0299(6) Uani d . 1 . .
H H20 0.5366 0.7053 0.1679 0.036 Uiso calc R 1 . .
C C21 0.4927(2) 0.6340(2) 0.0293(2) 0.0307(6) Uani d . 1 . .
H H21 0.5657 0.6127 0.0419 0.037 Uiso calc R 1 . .
C C22 0.4023(2) 0.6087(2) -0.06752(19) 0.0288(6) Uani d . 1 . .
C C23 0.4167(3) 0.5474(3) -0.1467(2) 0.0374(7) Uani d . 1 . .
H H23 0.4886 0.5245 -0.1351 0.045 Uiso calc R 1 . .
C C24 0.3276(3) 0.5223(3) -0.2383(2) 0.0435(8) Uani d . 1 . .
H H24 0.3387 0.4825 -0.2893 0.052 Uiso calc R 1 . .
C C25 0.2184(3) 0.5556(3) -0.2573(2) 0.0362(7) Uani d . 1 . .
H H25 0.1576 0.5375 -0.3209 0.043 Uiso calc R 1 . .
C C26 0.1997(3) 0.6143(2) -0.1841(2) 0.0322(6) Uani d . 1 . .
H H26 0.1267 0.6360 -0.1982 0.039 Uiso calc R 1 . .
C C27 0.2910(2) 0.6425(2) -0.08664(19) 0.0275(6) Uani d . 1 . .
C C28 0.3440(2) 0.7334(2) 0.24307(18) 0.0241(6) Uani d . 1 . .
C C29 0.3106(2) 0.7745(2) 0.39504(19) 0.0267(6) Uani d . 1 . .
C C30 0.2615(2) 0.6638(2) 0.40074(19) 0.0283(6) Uani d . 1 . .
H H30 0.2361 0.6035 0.3480 0.034 Uiso calc R 1 . .
C C31 0.2512(2) 0.6454(2) 0.4867(2) 0.0305(6) Uani d . 1 . .
C C32 0.2831(3) 0.7321(3) 0.5661(2) 0.0346(7) Uani d . 1 . .
H H32 0.2730 0.7178 0.6226 0.042 Uiso calc R 1 . .
C C33 0.3309(3) 0.8411(3) 0.5570(2) 0.0400(8) Uani d . 1 . .
C C34 0.3465(3) 0.8651(2) 0.4750(2) 0.0326(7) Uani d . 1 . .
H H34 0.3800 0.9397 0.4720 0.039 Uiso calc R 1 . .
Cl Cl5 0.57394(13) 0.34425(10) 0.69746(8) 0.0873(3) Uani d . 1 . .
Cl Cl6 0.60915(9) 0.78573(9) 0.73187(6) 0.0607(3) Uani d . 1 . .
Cl Cl7 0.73123(14) 0.08571(9) 0.71486(7) 0.0854(4) Uani d . 1 . .
Cl Cl8 0.69612(8) -0.20657(7) 0.40606(7) 0.0537(2) Uani d . 1 . .
O O3 0.58803(17) 0.40229(15) 0.37528(13) 0.0305(4) Uani d . 1 . .
O O4 0.38945(18) 0.01114(15) 0.25737(14) 0.0315(5) Uani d . 1 . .
N N5 0.47199(19) 0.46681(18) 0.24838(15) 0.0259(5) Uani d . 1 . .
H H5A 0.4076 0.4909 0.2261 0.031 Uiso calc R 1 . .
N N6 0.4839(2) 0.52764(19) 0.40193(16) 0.0320(6) Uani d . 1 . .
H H6A 0.4352 0.5656 0.3741 0.038 Uiso calc R 1 . .
N N7 0.4394(2) 0.18812(18) 0.22683(16) 0.0277(5) Uani d . 1 . .
H H7A 0.5038 0.2464 0.2402 0.033 Uiso calc R 1 . .
N N8 0.5607(2) 0.15267(19) 0.36835(16) 0.0308(6) Uani d . 1 . .
H H8A 0.5976 0.2248 0.3857 0.037 Uiso calc R 1 . .
C C35 0.4606(2) 0.3404(2) 0.10734(18) 0.0247(6) Uani d . 1 . .
C C36 0.5279(2) 0.4320(2) 0.18452(18) 0.0248(6) Uani d . 1 . .
C C37 0.6511(2) 0.4978(2) 0.2005(2) 0.0274(6) Uani d . 1 . .
H H37 0.6955 0.5590 0.2540 0.033 Uiso calc R 1 . .
C C38 0.7056(2) 0.4725(2) 0.1385(2) 0.0313(6) Uani d . 1 . .
H H38 0.7868 0.5163 0.1497 0.038 Uiso calc R 1 . .
C C39 0.6394(2) 0.3800(2) 0.0573(2) 0.0306(6) Uani d . 1 . .
C C40 0.6942(3) 0.3511(3) -0.0096(2) 0.0384(7) Uani d . 1 . .
H H40 0.7750 0.3947 0.0003 0.046 Uiso calc R 1 . .
C C41 0.6301(3) 0.2610(3) -0.0869(2) 0.0467(8) Uani d . 1 . .
H H41 0.6669 0.2431 -0.1295 0.056 Uiso calc R 1 . .
C C42 0.5080(3) 0.1948(3) -0.1025(2) 0.0459(8) Uani d . 1 . .
H H42 0.4648 0.1332 -0.1558 0.055 Uiso calc R 1 . .
C C43 0.4513(3) 0.2185(3) -0.0415(2) 0.0357(7) Uani d . 1 . .
H H43 0.3702 0.1735 -0.0536 0.043 Uiso calc R 1 . .
C C44 0.5155(2) 0.3116(2) 0.04026(19) 0.0282(6) Uani d . 1 . .
C C45 0.5200(2) 0.4621(2) 0.34418(19) 0.0257(6) Uani d . 1 . .
C C46 0.5201(2) 0.5380(2) 0.5033(2) 0.0316(6) Uani d . 1 . .
C C47 0.5281(3) 0.4448(3) 0.5451(2) 0.0400(7) Uani d . 1 . .
H H47 0.5087 0.3732 0.5068 0.048 Uiso calc R 1 . .
C C48 0.5655(3) 0.4610(3) 0.6453(2) 0.0496(8) Uani d . 1 . .
C C49 0.5941(3) 0.5648(4) 0.7049(2) 0.0521(9) Uani d . 1 . .
H H49 0.6217 0.5743 0.7723 0.062 Uiso calc R 1 . .
C C50 0.5800(3) 0.6546(3) 0.6602(2) 0.0431(8) Uani d . 1 . .
C C51 0.5458(2) 0.6426(3) 0.5610(2) 0.0328(7) Uani d . 1 . .
H H51 0.5401 0.7050 0.5331 0.039 Uiso calc R 1 . .
C C52 0.3332(2) 0.2647(2) 0.09375(18) 0.0242(6) Uani d . 1 . .
C C53 0.3265(2) 0.1840(2) 0.14977(18) 0.0257(6) Uani d . 1 . .
C C54 0.2083(2) 0.1063(2) 0.1341(2) 0.0293(6) Uani d . 1 . .
H H54 0.2051 0.0504 0.1699 0.035 Uiso calc R 1 . .
C C55 0.1008(3) 0.1138(2) 0.0669(2) 0.0326(7) Uani d . 1 . .
H H55 0.0240 0.0622 0.0571 0.039 Uiso calc R 1 . .
C C56 0.1008(3) 0.1980(2) 0.0108(2) 0.0301(6) Uani d . 1 . .
C C57 -0.0113(3) 0.2103(3) -0.0556(2) 0.0394(8) Uani d . 1 . .
H H57 -0.0890 0.1631 -0.0624 0.047 Uiso calc R 1 . .
C C58 -0.0077(3) 0.2909(3) -0.1105(2) 0.0457(9) Uani d . 1 . .
H H58 -0.0825 0.2986 -0.1537 0.055 Uiso calc R 1 . .
C C59 0.1091(3) 0.3610(3) -0.1008(2) 0.0402(8) Uani d . 1 . .
H H59 0.1112 0.4134 -0.1400 0.048 Uiso calc R 1 . .
C C60 0.2204(3) 0.3545(2) -0.0352(2) 0.0319(7) Uani d . 1 . .
H H60 0.2969 0.4037 -0.0289 0.038 Uiso calc R 1 . .
C C61 0.2197(2) 0.2725(2) 0.02373(19) 0.0272(6) Uani d . 1 . .
C C62 0.4579(2) 0.1102(2) 0.28235(19) 0.0274(6) Uani d . 1 . .
C C63 0.6103(3) 0.0830(2) 0.4313(2) 0.0318(7) Uani d . 1 . .
C C64 0.6429(3) 0.1150(3) 0.5305(2) 0.0409(8) Uani d . 1 . .
H H64 0.6321 0.1813 0.5567 0.049 Uiso calc R 1 . .
C C65 0.6920(3) 0.0463(3) 0.5902(2) 0.0459(9) Uani d . 1 . .
C C66 0.7090(3) -0.0520(3) 0.5542(2) 0.0418(8) Uani d . 1 . .
H H66 0.7421 -0.0969 0.5954 0.050 Uiso calc R 1 . .
C C67 0.6757(3) -0.0823(2) 0.4553(2) 0.0370(7) Uani d . 1 . .
C C68 0.6273(3) -0.0162(2) 0.3914(2) 0.0357(7) Uani d . 1 . .
H H68 0.6071 -0.0374 0.3249 0.043 Uiso calc R 1 . .
Cl Cl10 0.53490(16) 0.01074(15) 0.09971(13) 0.0546(4) Uani d PD 0.60 A 1
Cl Cl12 0.79357(19) 0.0613(2) 0.11063(18) 0.0980(7) Uani d PD 0.60 A 1
Cl Cl11 0.5872(2) -0.0818(3) -0.06273(18) 0.0971(8) Uani d PD 0.60 A 1
C C100 0.6370(5) 0.0287(5) 0.0408(4) 0.0498(12) Uani d PD 0.60 A 1
H H100 0.6287 0.0959 0.0141 0.060 Uiso calc PR 0.60 A 1
Cl Cl13 0.5597(3) -0.0111(3) 0.1169(2) 0.0546(4) Uani d PD 0.40 B 2
Cl Cl14 0.7862(4) 0.0531(4) 0.0786(3) 0.0971(8) Uani d PD 0.40 B 2
Cl Cl15 0.5513(3) -0.0905(4) -0.0699(3) 0.0980(7) Uani d PD 0.40 B 2
C C101 0.6412(7) -0.0388(8) 0.0563(6) 0.0498(12) Uani d PD 0.40 B 2
H H101 0.6623 -0.1056 0.0774 0.060 Uiso calc PR 0.40 B 2
Cl Cl20 0.82035(18) 0.77629(17) 0.17030(17) 0.0558(4) Uani d PD 0.58 C 1
Cl Cl21 0.96509(17) 0.73874(16) 0.35521(16) 0.0570(3) Uani d PD 0.58 C 1
Cl Cl22 1.0749(2) 0.92854(18) 0.2861(2) 0.0697(3) Uani d PD 0.58 C 1
C C200 0.9738(6) 0.7888(5) 0.2535(5) 0.0436(9) Uani d PD 0.58 C 1
H H200 1.0083 0.7401 0.2214 0.052 Uiso calc PR 0.58 C 1
Cl Cl23 0.8182(3) 0.7926(3) 0.1869(3) 0.0558(4) Uani d PD 0.42 D 2
Cl Cl25 1.0739(4) 0.9381(3) 0.2815(4) 0.0697(3) Uani d PD 0.42 D 2
Cl Cl24 0.9869(3) 0.7649(3) 0.3707(2) 0.0570(3) Uani d PD 0.42 D 2
C C201 0.9742(9) 0.8007(8) 0.2597(7) 0.0436(9) Uani d PD 0.42 D 2
H H201 1.0011 0.7477 0.2245 0.052 Uiso calc PR 0.42 D 2
Cl Cl30 0.9302(4) 0.5635(5) 0.5023(3) 0.1098(6) Uani d PD 0.50 E 1
Cl Cl31 0.8503(3) 0.4372(3) 0.6273(4) 0.1080(6) Uani d PD 0.50 E 1
Cl Cl32 0.8902(3) 0.6767(4) 0.6599(3) 0.0959(5) Uani d PD 0.50 E 1
C C300 0.8422(8) 0.5524(7) 0.5724(6) 0.0608(11) Uani d PD 0.50 E 1
H H300 0.7537 0.5393 0.5291 0.073 Uiso calc PR 0.50 E 1
Cl Cl33 0.9259(4) 0.5540(6) 0.5012(4) 0.1098(6) Uani d PD 0.50 F 2
Cl Cl35 0.8991(4) 0.6884(4) 0.6568(3) 0.0959(5) Uani d PD 0.50 F 2
Cl Cl34 0.8638(4) 0.4516(4) 0.6438(4) 0.1080(6) Uani d PD 0.50 F 2
C C301 0.8468(9) 0.5568(8) 0.5774(7) 0.0608(11) Uani d PD 0.50 F 2
H H301 0.7567 0.5407 0.5370 0.073 Uiso calc PR 0.50 F 2
Cl Cl40 1.01580(19) 0.25846(16) 0.58778(16) 0.0958(5) Uani d PD 0.77 G 1
Cl Cl41 1.0437(2) 0.03823(16) 0.54162(17) 0.1061(7) Uani d PD 0.77 G 1
Cl Cl42 1.22528(18) 0.20149(14) 0.71565(12) 0.0890(5) Uani d PD 0.77 G 1
C C400 1.1179(9) 0.1762(6) 0.6000(6) 0.134(4) Uani d PD 0.77 G 1
H H400 1.1683 0.2055 0.5638 0.161 Uiso calc PR 0.77 G 1
Cl Cl45 1.2546(6) 0.2198(5) 0.6413(4) 0.0890(5) Uani d PD 0.23 H 2
C C401 1.1031(13) 0.1494(12) 0.6348(17) 0.134(4) Uani d PD 0.23 H 2
H H401 1.1074 0.1547 0.7015 0.161 Uiso calc PR 0.23 H 2
Cl Cl44 1.0423(9) 0.0034(6) 0.5739(6) 0.1061(7) Uani d PD 0.23 H 2
Cl Cl43 0.9875(7) 0.2056(6) 0.5716(6) 0.0958(5) Uani d PD 0.23 H 2
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'
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'
Cl Cl 0.1484 0.1585 '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_3
_geom_angle
_geom_angle_publ_flag
C11 N1 C2 . . 127.1(3) ?
C11 N1 H1A . . 116.4 ?
C2 N1 H1A . . 116.4 ?
C11 N2 C12 . . 127.1(2) ?
C11 N2 H2A . . 116.4 ?
C12 N2 H2A . . 116.4 ?
C28 N3 C19 . . 123.0(2) ?
C28 N3 H3A . . 118.5 ?
C19 N3 H3A . . 118.5 ?
C28 N4 C29 . . 126.0(2) ?
C28 N4 H4A . . 117.0 ?
C29 N4 H4A . . 117.0 ?
C2 C1 C10 . . 119.2(2) ?
C2 C1 C18 . . 119.6(2) ?
C10 C1 C18 . . 121.1(2) ?
C1 C2 C3 . . 121.1(3) ?
C1 C2 N1 . . 118.2(2) ?
C3 C2 N1 . . 120.6(2) ?
C4 C3 C2 . . 119.8(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 121.6(3) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C4 C5 C6 . . 122.6(3) ?
C4 C5 C10 . . 119.1(3) ?
C6 C5 C10 . . 118.2(3) ?
C7 C6 C5 . . 121.6(3) ?
C7 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
C6 C7 C8 . . 120.0(3) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 120.6(3) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C8 C9 C10 . . 121.1(3) ?
C8 C9 H9 . . 119.4 ?
C10 C9 H9 . . 119.4 ?
C9 C10 C5 . . 118.4(3) ?
C9 C10 C1 . . 122.4(3) ?
C5 C10 C1 . . 119.2(3) ?
O1 C11 N1 . . 124.1(3) ?
O1 C11 N2 . . 123.0(3) ?
N1 C11 N2 . . 112.8(3) ?
C17 C12 C13 . . 120.5(3) ?
C17 C12 N2 . . 117.5(3) ?
C13 C12 N2 . . 121.8(3) ?
C14 C13 C12 . . 118.1(3) ?
C14 C13 H13 . . 120.9 ?
C12 C13 H13 . . 120.9 ?
C13 C14 C15 . . 123.5(3) ?
C13 C14 Cl2 . . 118.7(2) ?
C15 C14 Cl2 . . 117.8(2) ?
C14 C15 C16 . . 116.1(3) ?
C14 C15 H15 . . 121.9 ?
C16 C15 H15 . . 121.9 ?
C17 C16 C15 . . 122.4(3) ?
C17 C16 Cl1 . . 119.5(2) ?
C15 C16 Cl1 . . 118.1(2) ?
C16 C17 C12 . . 119.4(3) ?
C16 C17 H17 . . 120.3 ?
C12 C17 H17 . . 120.3 ?
C19 C18 C27 . . 118.6(2) ?
C19 C18 C1 . . 120.5(2) ?
C27 C18 C1 . . 120.7(2) ?
C18 C19 C20 . . 121.7(3) ?
C18 C19 N3 . . 119.2(2) ?
C20 C19 N3 . . 119.1(2) ?
C21 C20 C19 . . 119.9(2) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C20 C21 C22 . . 121.4(3) ?
C20 C21 H21 . . 119.3 ?
C22 C21 H21 . . 119.3 ?
C21 C22 C23 . . 122.1(3) ?
C21 C22 C27 . . 119.1(3) ?
C23 C22 C27 . . 118.8(2) ?
C24 C23 C22 . . 120.9(3) ?
C24 C23 H23 . . 119.5 ?
C22 C23 H23 . . 119.5 ?
C23 C24 C25 . . 120.4(3) ?
C23 C24 H24 . . 119.8 ?
C25 C24 H24 . . 119.8 ?
C26 C25 C24 . . 121.1(3) ?
C26 C25 H25 . . 119.5 ?
C24 C25 H25 . . 119.5 ?
C25 C26 C27 . . 120.3(3) ?
C25 C26 H26 . . 119.8 ?
C27 C26 H26 . . 119.8 ?
C26 C27 C22 . . 118.5(3) ?
C26 C27 C18 . . 122.3(3) ?
C22 C27 C18 . . 119.2(2) ?
O2 C28 N3 . . 123.1(2) ?
O2 C28 N4 . . 123.1(2) ?
N3 C28 N4 . . 113.8(2) ?
C30 C29 C34 . . 120.1(3) ?
C30 C29 N4 . . 122.7(2) ?
C34 C29 N4 . . 117.3(2) ?
C31 C30 C29 . . 118.3(3) ?
C31 C30 H30 . . 120.8 ?
C29 C30 H30 . . 120.8 ?
C30 C31 C32 . . 123.3(3) ?
C30 C31 Cl3 . . 117.3(2) ?
C32 C31 Cl3 . . 119.4(2) ?
C33 C32 C31 . . 116.3(3) ?
C33 C32 H32 . . 121.9 ?
C31 C32 H32 . . 121.9 ?
C34 C33 C32 . . 123.4(3) ?
C34 C33 Cl4 . . 118.4(2) ?
C32 C33 Cl4 . . 118.3(2) ?
C33 C34 C29 . . 118.5(3) ?
C33 C34 H34 . . 120.7 ?
C29 C34 H34 . . 120.7 ?
C45 N5 C36 . . 120.5(2) ?
C45 N5 H5A . . 119.7 ?
C36 N5 H5A . . 119.7 ?
C45 N6 C46 . . 125.3(2) ?
C45 N6 H6A . . 117.3 ?
C46 N6 H6A . . 117.3 ?
C62 N7 C53 . . 127.2(2) ?
C62 N7 H7A . . 116.4 ?
C53 N7 H7A . . 116.4 ?
C62 N8 C63 . . 122.9(2) ?
C62 N8 H8A . . 118.5 ?
C63 N8 H8A . . 118.5 ?
C36 C35 C44 . . 119.5(2) ?
C36 C35 C52 . . 121.7(2) ?
C44 C35 C52 . . 118.8(2) ?
C35 C36 C37 . . 121.2(3) ?
C35 C36 N5 . . 120.4(2) ?
C37 C36 N5 . . 118.3(2) ?
C38 C37 C36 . . 120.6(2) ?
C38 C37 H37 . . 119.7 ?
C36 C37 H37 . . 119.7 ?
C37 C38 C39 . . 120.2(2) ?
C37 C38 H38 . . 119.9 ?
C39 C38 H38 . . 119.9 ?
C38 C39 C44 . . 120.2(3) ?
C38 C39 C40 . . 121.5(2) ?
C44 C39 C40 . . 118.3(2) ?
C41 C40 C39 . . 121.0(3) ?
C41 C40 H40 . . 119.5 ?
C39 C40 H40 . . 119.5 ?
C40 C41 C42 . . 119.9(3) ?
C40 C41 H41 . . 120.0 ?
C42 C41 H41 . . 120.0 ?
C43 C42 C41 . . 121.6(3) ?
C43 C42 H42 . . 119.2 ?
C41 C42 H42 . . 119.2 ?
C42 C43 C44 . . 120.2(3) ?
C42 C43 H43 . . 119.9 ?
C44 C43 H43 . . 119.9 ?
C43 C44 C39 . . 119.1(3) ?
C43 C44 C35 . . 122.6(2) ?
C39 C44 C35 . . 118.3(2) ?
O3 C45 N5 . . 122.8(3) ?
O3 C45 N6 . . 123.4(2) ?
N5 C45 N6 . . 113.8(2) ?
C51 C46 C47 . . 119.9(3) ?
C51 C46 N6 . . 118.8(3) ?
C47 C46 N6 . . 121.3(3) ?
C48 C47 C46 . . 118.4(3) ?
C48 C47 H47 . . 120.8 ?
C46 C47 H47 . . 120.8 ?
C49 C48 C47 . . 122.9(3) ?
C49 C48 Cl5 . . 118.7(3) ?
C47 C48 Cl5 . . 118.4(3) ?
C48 C49 C50 . . 117.0(3) ?
C48 C49 H49 . . 121.5 ?
C50 C49 H49 . . 121.5 ?
C51 C50 C49 . . 121.8(3) ?
C51 C50 Cl6 . . 119.6(3) ?
C49 C50 Cl6 . . 118.6(3) ?
C46 C51 C50 . . 119.9(3) ?
C46 C51 H51 . . 120.1 ?
C50 C51 H51 . . 120.1 ?
C53 C52 C61 . . 119.1(2) ?
C53 C52 C35 . . 119.4(2) ?
C61 C52 C35 . . 121.4(2) ?
C52 C53 N7 . . 117.5(2) ?
C52 C53 C54 . . 120.7(2) ?
N7 C53 C54 . . 121.6(2) ?
C55 C54 C53 . . 119.7(3) ?
C55 C54 H54 . . 120.2 ?
C53 C54 H54 . . 120.2 ?
C54 C55 C56 . . 122.3(2) ?
C54 C55 H55 . . 118.9 ?
C56 C55 H55 . . 118.9 ?
C57 C56 C55 . . 122.6(3) ?
C57 C56 C61 . . 119.6(3) ?
C55 C56 C61 . . 117.8(2) ?
C58 C57 C56 . . 121.1(3) ?
C58 C57 H57 . . 119.5 ?
C56 C57 H57 . . 119.5 ?
C57 C58 C59 . . 119.4(3) ?
C57 C58 H58 . . 120.3 ?
C59 C58 H58 . . 120.3 ?
C60 C59 C58 . . 121.6(3) ?
C60 C59 H59 . . 119.2 ?
C58 C59 H59 . . 119.2 ?
C59 C60 C61 . . 120.2(3) ?
C59 C60 H60 . . 119.9 ?
C61 C60 H60 . . 119.9 ?
C52 C61 C56 . . 120.2(2) ?
C52 C61 C60 . . 121.8(2) ?
C56 C61 C60 . . 118.0(2) ?
O4 C62 N8 . . 123.2(2) ?
O4 C62 N7 . . 123.7(2) ?
N8 C62 N7 . . 113.1(2) ?
C64 C63 C68 . . 120.9(3) ?
C64 C63 N8 . . 119.9(3) ?
C68 C63 N8 . . 119.2(3) ?
C63 C64 C65 . . 118.8(3) ?
C63 C64 H64 . . 120.6 ?
C65 C64 H64 . . 120.6 ?
C66 C65 C64 . . 122.3(3) ?
C66 C65 Cl7 . . 119.0(3) ?
C64 C65 Cl7 . . 118.7(3) ?
C65 C66 C67 . . 118.0(3) ?
C65 C66 H66 . . 121.0 ?
C67 C66 H66 . . 121.0 ?
C66 C67 C68 . . 122.6(3) ?
C66 C67 Cl8 . . 119.6(2) ?
C68 C67 Cl8 . . 117.8(3) ?
C67 C68 C63 . . 117.5(3) ?
C67 C68 H68 . . 121.3 ?
C63 C68 H68 . . 121.3 ?
Cl12 C100 Cl10 . . 117.4(3) ?
Cl12 C100 Cl11 . . 112.0(4) ?
Cl10 C100 Cl11 . . 112.6(3) ?
Cl12 C100 H100 . . 104.4 ?
Cl10 C100 H100 . . 104.4 ?
Cl11 C100 H100 . . 104.4 ?
Cl13 C101 Cl14 . . 121.0(5) ?
Cl13 C101 Cl15 . . 113.7(5) ?
Cl14 C101 Cl15 . . 111.0(5) ?
Cl13 C101 H101 . . 102.8 ?
Cl14 C101 H101 . . 102.8 ?
Cl15 C101 H101 . . 102.8 ?
Cl21 C200 Cl22 . . 112.0(4) ?
Cl21 C200 Cl20 . . 109.4(4) ?
Cl22 C200 Cl20 . . 111.8(4) ?
Cl21 C200 H200 . . 107.8 ?
Cl22 C200 H200 . . 107.8 ?
Cl20 C200 H200 . . 107.8 ?
Cl24 C201 Cl25 . . 109.4(5) ?
Cl24 C201 Cl23 . . 111.8(6) ?
Cl25 C201 Cl23 . . 109.6(6) ?
Cl24 C201 H201 . . 108.6 ?
Cl25 C201 H201 . . 108.6 ?
Cl23 C201 H201 . . 108.6 ?
Cl30 C300 Cl32 . . 111.5(5) ?
Cl30 C300 Cl31 . . 110.9(6) ?
Cl32 C300 Cl31 . . 110.4(5) ?
Cl30 C300 H300 . . 108.0 ?
Cl32 C300 H300 . . 108.0 ?
Cl31 C300 H300 . . 108.0 ?
Cl33 C301 Cl35 . . 112.2(6) ?
Cl33 C301 Cl34 . . 110.1(7) ?
Cl35 C301 Cl34 . . 109.8(6) ?
Cl33 C301 H301 . . 108.2 ?
Cl35 C301 H301 . . 108.2 ?
Cl34 C301 H301 . . 108.2 ?
Cl42 C400 Cl41 . . 116.4(5) ?
Cl42 C400 Cl40 . . 112.7(5) ?
Cl41 C400 Cl40 . . 113.6(5) ?
Cl42 C400 H400 . . 104.1 ?
Cl41 C400 H400 . . 104.1 ?
Cl40 C400 H400 . . 104.1 ?
Cl43 C401 Cl45 . . 113.6(11) ?
Cl43 C401 Cl44 . . 103.4(9) ?
Cl45 C401 Cl44 . . 114.7(11) ?
Cl43 C401 H401 . . 108.3 ?
Cl45 C401 H401 . . 108.3 ?
Cl44 C401 H401 . . 108.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C16 . 1.738(3) ?
Cl2 C14 . 1.740(3) ?
Cl3 C31 . 1.742(3) ?
Cl4 C33 . 1.745(3) ?
O1 C11 . 1.215(4) ?
O2 C28 . 1.231(3) ?
N1 C11 . 1.364(4) ?
N1 C2 . 1.417(4) ?
N1 H1A . 0.8600 ?
N2 C11 . 1.372(4) ?
N2 C12 . 1.417(4) ?
N2 H2A . 0.8600 ?
N3 C28 . 1.354(3) ?
N3 C19 . 1.422(4) ?
N3 H3A . 0.8600 ?
N4 C28 . 1.366(4) ?
N4 C29 . 1.409(4) ?
N4 H4A . 0.8600 ?
C1 C2 . 1.386(4) ?
C1 C10 . 1.432(4) ?
C1 C18 . 1.496(4) ?
C2 C3 . 1.413(4) ?
C3 C4 . 1.368(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.406(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.422(4) ?
C5 C10 . 1.425(4) ?
C6 C7 . 1.350(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.411(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.355(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.420(4) ?
C9 H9 . 0.9300 ?
C12 C17 . 1.380(4) ?
C12 C13 . 1.395(4) ?
C13 C14 . 1.375(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.392(4) ?
C15 C16 . 1.391(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.376(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.385(3) ?
C18 C27 . 1.435(4) ?
C19 C20 . 1.407(4) ?
C20 C21 . 1.358(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.409(4) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.423(4) ?
C22 C27 . 1.426(4) ?
C23 C24 . 1.347(4) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.400(5) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.363(4) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.418(4) ?
C26 H26 . 0.9300 ?
C29 C30 . 1.386(4) ?
C29 C34 . 1.408(4) ?
C30 C31 . 1.382(4) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.383(4) ?
C32 C33 . 1.382(5) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.366(4) ?
C34 H34 . 0.9300 ?
Cl5 C48 . 1.737(4) ?
Cl6 C50 . 1.730(4) ?
Cl7 C65 . 1.738(4) ?
Cl8 C67 . 1.744(3) ?
O3 C45 . 1.236(3) ?
O4 C62 . 1.229(3) ?
N5 C45 . 1.362(3) ?
N5 C36 . 1.431(4) ?
N5 H5A . 0.8600 ?
N6 C45 . 1.369(4) ?
N6 C46 . 1.408(4) ?
N6 H6A . 0.8600 ?
N7 C62 . 1.359(4) ?
N7 C53 . 1.411(3) ?
N7 H7A . 0.8600 ?
N8 C62 . 1.358(3) ?
N8 C63 . 1.427(4) ?
N8 H8A . 0.8600 ?
C35 C36 . 1.369(3) ?
C35 C44 . 1.438(4) ?
C35 C52 . 1.505(4) ?
C36 C37 . 1.413(4) ?
C37 C38 . 1.359(4) ?
C37 H37 . 0.9300 ?
C38 C39 . 1.408(4) ?
C38 H38 . 0.9300 ?
C39 C44 . 1.425(4) ?
C39 C40 . 1.436(4) ?
C40 C41 . 1.357(4) ?
C40 H40 . 0.9300 ?
C41 C42 . 1.404(5) ?
C41 H41 . 0.9300 ?
C42 C43 . 1.363(5) ?
C42 H42 . 0.9300 ?
C43 C44 . 1.417(4) ?
C43 H43 . 0.9300 ?
C46 C51 . 1.377(4) ?
C46 C47 . 1.391(4) ?
C47 C48 . 1.384(5) ?
C47 H47 . 0.9300 ?
C48 C49 . 1.374(5) ?
C49 C50 . 1.384(5) ?
C49 H49 . 0.9300 ?
C50 C51 . 1.377(4) ?
C51 H51 . 0.9300 ?
C52 C53 . 1.390(4) ?
C52 C61 . 1.418(4) ?
C53 C54 . 1.420(4) ?
C54 C55 . 1.349(4) ?
C54 H54 . 0.9300 ?
C55 C56 . 1.420(4) ?
C55 H55 . 0.9300 ?
C56 C57 . 1.406(4) ?
C56 C61 . 1.422(4) ?
C57 C58 . 1.374(5) ?
C57 H57 . 0.9300 ?
C58 C59 . 1.396(5) ?
C58 H58 . 0.9300 ?
C59 C60 . 1.367(4) ?
C59 H59 . 0.9300 ?
C60 C61 . 1.429(4) ?
C60 H60 . 0.9300 ?
C63 C64 . 1.382(4) ?
C63 C68 . 1.400(4) ?
C64 C65 . 1.388(5) ?
C64 H64 . 0.9300 ?
C65 C66 . 1.368(5) ?
C66 C67 . 1.375(5) ?
C66 H66 . 0.9300 ?
C67 C68 . 1.396(4) ?
C68 H68 . 0.9300 ?
Cl10 C100 . 1.729(6) ?
Cl12 C100 . 1.693(6) ?
Cl11 C100 . 1.765(6) ?
C100 H100 . 0.9800 ?
Cl13 C101 . 1.614(9) ?
Cl14 C101 . 1.712(9) ?
Cl15 C101 . 1.759(8) ?
C101 H101 . 0.9800 ?
Cl20 C200 . 1.761(6) ?
Cl21 C200 . 1.745(8) ?
Cl22 C200 . 1.754(6) ?
C200 H200 . 0.9800 ?
Cl23 C201 . 1.755(10) ?
Cl25 C201 . 1.747(9) ?
Cl24 C201 . 1.741(11) ?
C201 H201 . 0.9800 ?
Cl30 C300 . 1.724(10) ?
Cl31 C300 . 1.742(10) ?
Cl32 C300 . 1.736(9) ?
C300 H300 . 0.9800 ?
Cl33 C301 . 1.724(11) ?
Cl35 C301 . 1.736(10) ?
Cl34 C301 . 1.743(11) ?
C301 H301 . 0.9800 ?
Cl40 C400 . 1.743(9) ?
Cl41 C400 . 1.691(8) ?
Cl42 C400 . 1.687(7) ?
C400 H400 . 0.9800 ?
Cl45 C401 . 1.763(16) ?
C401 Cl43 . 1.723(15) ?
C401 Cl44 . 1.780(15) ?
C401 H401 . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
N3 H3A O4 . . 1_565 0.86 2.16 2.897(3) 144 y
N4 H4A O4 . . 1_565 0.86 2.05 2.821(3) 149 y
N5 H5A O2 . . . 0.86 2.11 2.821(3) 139 y
N6 H6A O2 . . . 0.86 2.17 2.947(3) 150 y
N7 H7A O3 . . . 0.86 2.36 2.955(3) 126 y
N8 H8A O3 . . . 0.86 2.26 3.030(3) 149 y
C3 H3 O1 . . . 0.93 2.44 2.937(3) 113 no
C13 H13 O1 . . . 0.93 2.47 2.943(3) 112 no
C30 H30 O2 . . . 0.93 2.38 2.864(3) 113 no
C38 H38 O1 . . 1_655 0.93 2.41 3.304(4) 162 y
C47 H47 O3 . . . 0.93 2.50 2.911(4) 107 no
C54 H54 O4 . . . 0.93 2.32 2.893(3) 120 y
C200 H200 O1 . . 1_655 0.98 2.15 3.035(7) 149 y
C300 H300 O3 1_555 1_555 1_555 0.98 2.52 3.315(9) 138 y
N2 H2A Cg1 . . . 0.86 2.59 3.300(3) 141 y
