#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/07/2220727.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_2220727
loop_
_publ_author_name
'Lee, See Mun'
'Ali, Hapipah Mohd.'
'Lo, Kong Mun'
'Ng, Seik Weng'
_publ_section_title
;2-{1-[2-(Bis{2-[1-(5-chloro-2-hydroxyphenyl)ethylideneamino]ethyl}amino)ethyliminio]ethyl}-4-chlorophenolate
 toluene hemisolvate
;
_journal_coeditor_code           BT2855
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o409
_journal_paper_doi               10.1107/S1600536809002906
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C30 H33 Cl3 N4 O3, 0.5C7 H8'
_chemical_formula_moiety         'C30 H33 Cl3 N4 O3, 0.5(C7 H8)'
_chemical_formula_sum            'C33.5 H37 Cl3 N4 O3'
_chemical_formula_weight         650.02
_chemical_name_systematic
;2-{1-[2-(Bis{2-[1-(5-chloro-2-
hydroxyphenyl)ethylideneamino]ethyl}amino)ethyliminio]ethyl}-4-chlorophenolate
toluene
 hemisolvate
;
_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                100.618(2)
_cell_angle_beta                 97.765(2)
_cell_angle_gamma                98.560(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3651(2)
_cell_length_b                   11.1839(2)
_cell_length_c                   20.1594(5)
_cell_measurement_reflns_used    3243
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      2.3
_cell_volume                     1591.20(7)
_computing_cell_refinement       'APEX2 (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'pubCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14959
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             682
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.800
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         7269
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0807P)²+0.0533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                4901
_reflns_number_total             7269
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2855.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C33.50 H37 Cl3 N4 O3'
_cod_database_code               2220727
_cod_database_fobs_code          2220727
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 -0.23379(11) 0.63575(6) 0.19284(4) 0.03291(19) Uani d . 1 . .
Cl Cl2 0.23675(10) 0.10135(7) 0.68824(3) 0.03301(19) Uani d . 1 . .
Cl Cl3 0.21656(11) 0.59383(6) 0.09250(5) 0.0398(2) Uani d . 1 . .
O O1 0.0640(3) 0.21520(18) 0.27035(9) 0.0250(4) Uani d D 1 . .
O O2 0.1122(3) -0.23059(17) 0.41888(9) 0.0268(4) Uani d D 1 . .
O O3 0.4300(2) 0.11432(15) 0.00308(9) 0.0209(4) Uani d . 1 . .
N N1 0.0135(3) 0.11221(18) 0.14742(10) 0.0173(4) Uani d . 1 . .
N N2 0.2570(3) -0.05363(19) 0.37189(10) 0.0203(5) Uani d . 1 . .
N N3 0.5052(3) 0.0992(2) 0.12427(11) 0.0194(4) Uani d D 1 . .
N N4 0.2407(3) -0.07266(19) 0.18467(10) 0.0185(4) Uani d . 1 . .
C C1 0.0036(3) 0.3111(2) 0.25116(13) 0.0202(5) Uani d . 1 . .
C C2 -0.0030(4) 0.4161(3) 0.30111(13) 0.0263(6) Uani d . 1 . .
H H2 0.0400 0.4174 0.3479 0.032 Uiso calc R 1 . .
C C3 -0.0698(4) 0.5162(2) 0.28386(14) 0.0267(6) Uani d . 1 . .
H H3 -0.0713 0.5867 0.3182 0.032 Uiso calc R 1 . .
C C4 -0.1358(4) 0.5134(2) 0.21528(13) 0.0229(6) Uani d . 1 . .
C C5 -0.1268(3) 0.4145(2) 0.16472(13) 0.0196(5) Uani d . 1 . .
H H5 -0.1684 0.4160 0.1182 0.024 Uiso calc R 1 . .
C C6 -0.0570(3) 0.3114(2) 0.18097(12) 0.0172(5) Uani d . 1 . .
C C7 -0.0454(3) 0.2053(2) 0.12730(12) 0.0159(5) Uani d . 1 . .
C C8 -0.1005(3) 0.2054(2) 0.05297(12) 0.0199(5) Uani d . 1 . .
H H8A 0.0064 0.1964 0.0295 0.030 Uiso calc R 1 . .
H H8B -0.1410 0.2834 0.0483 0.030 Uiso calc R 1 . .
H H8C -0.2028 0.1363 0.0325 0.030 Uiso calc R 1 . .
C C9 0.0297(3) 0.0003(2) 0.09993(13) 0.0185(5) Uani d . 1 . .
H H9A 0.1345 0.0184 0.0752 0.022 Uiso calc R 1 . .
H H9B -0.0860 -0.0278 0.0658 0.022 Uiso calc R 1 . .
C C10 0.0625(3) -0.1009(2) 0.13845(13) 0.0190(5) Uani d . 1 . .
H H10A -0.0391 -0.1145 0.1652 0.023 Uiso calc R 1 . .
H H10B 0.0573 -0.1787 0.1050 0.023 Uiso calc R 1 . .
C C11 0.1462(3) -0.1520(2) 0.47997(13) 0.0210(5) Uani d . 1 . .
C C12 0.0918(4) -0.1964(3) 0.53595(13) 0.0247(6) Uani d . 1 . .
H H12 0.0335 -0.2803 0.5298 0.030 Uiso calc R 1 . .
C C13 0.1212(4) -0.1205(3) 0.60011(13) 0.0260(6) Uani d . 1 . .
H H13 0.0837 -0.1516 0.6379 0.031 Uiso calc R 1 . .
C C14 0.2062(3) 0.0015(3) 0.60846(13) 0.0238(6) Uani d . 1 . .
C C15 0.2619(3) 0.0482(2) 0.55447(13) 0.0215(5) Uani d . 1 . .
H H15 0.3199 0.1323 0.5617 0.026 Uiso calc R 1 . .
C C16 0.2337(3) -0.0273(2) 0.48890(12) 0.0188(5) Uani d . 1 . .
C C17 0.2881(3) 0.0227(2) 0.43020(12) 0.0193(5) Uani d . 1 . .
C C18 0.3728(4) 0.1565(2) 0.43895(14) 0.0266(6) Uani d . 1 . .
H H18A 0.3127 0.1905 0.4020 0.040 Uiso calc R 1 . .
H H18B 0.5064 0.1639 0.4374 0.040 Uiso calc R 1 . .
H H18C 0.3546 0.2025 0.4832 0.040 Uiso calc R 1 . .
C C19 0.2943(4) -0.0111(2) 0.30971(12) 0.0241(6) Uani d . 1 . .
H H19A 0.4289 0.0214 0.3141 0.029 Uiso calc R 1 . .
H H19B 0.2253 0.0566 0.3034 0.029 Uiso calc R 1 . .
C C20 0.2347(4) -0.1166(3) 0.24873(13) 0.0256(6) Uani d . 1 . .
H H20A 0.3182 -0.1778 0.2515 0.031 Uiso calc R 1 . .
H H20B 0.1065 -0.1581 0.2491 0.031 Uiso calc R 1 . .
C C21 0.3929(3) 0.2251(2) 0.02511(13) 0.0191(5) Uani d . 1 . .
C C22 0.3371(3) 0.2955(2) -0.02214(14) 0.0221(5) Uani d . 1 . .
H H22 0.3345 0.2646 -0.0695 0.027 Uiso calc R 1 . .
C C23 0.2860(4) 0.4080(2) -0.00169(15) 0.0258(6) Uani d . 1 . .
H H23 0.2471 0.4539 -0.0346 0.031 Uiso calc R 1 . .
C C24 0.2918(4) 0.4542(2) 0.06778(15) 0.0251(6) Uani d . 1 . .
C C25 0.3537(3) 0.3918(2) 0.11611(14) 0.0238(6) Uani d . 1 . .
H H25 0.3616 0.4269 0.1633 0.029 Uiso calc R 1 . .
C C26 0.4060(3) 0.2759(2) 0.09650(13) 0.0190(5) Uani d . 1 . .
C C27 0.4692(3) 0.2072(2) 0.14771(13) 0.0203(5) Uani d . 1 . .
C C28 0.4898(4) 0.2621(3) 0.22289(13) 0.0263(6) Uani d . 1 . .
H H28A 0.5594 0.2133 0.2493 0.040 Uiso calc R 1 . .
H H28B 0.3662 0.2612 0.2359 0.040 Uiso calc R 1 . .
H H28C 0.5572 0.3474 0.2324 0.040 Uiso calc R 1 . .
C C29 0.5577(3) 0.0091(2) 0.16366(14) 0.0249(6) Uani d . 1 . .
H H29A 0.5869 0.0481 0.2130 0.030 Uiso calc R 1 . .
H H29B 0.6703 -0.0197 0.1498 0.030 Uiso calc R 1 . .
C C30 0.3992(3) -0.1001(2) 0.15147(13) 0.0197(5) Uani d . 1 . .
H H30A 0.3555 -0.1282 0.1016 0.024 Uiso calc R 1 . .
H H30B 0.4468 -0.1689 0.1685 0.024 Uiso calc R 1 . .
C C31 0.4925(19) 0.5285(12) 0.4490(5) 0.083(3) Uani d PGDU 0.50 A -1
C C32 0.3426(19) 0.5415(12) 0.4832(5) 0.059(3) Uani d PGDU 0.50 A -1
H H32 0.2419 0.5754 0.4641 0.071 Uiso calc PR 0.50 A -1
C C33 0.340(2) 0.5050(13) 0.5454(5) 0.089(3) Uani d PGU 0.50 A -1
H H33 0.2376 0.5139 0.5688 0.107 Uiso calc PR 0.50 A -1
C C34 0.487(2) 0.4554(12) 0.5734(5) 0.083(3) Uani d PG 0.50 A -1
H H34 0.4856 0.4305 0.6159 0.100 Uiso calc PR 0.50 A -1
C C35 0.637(2) 0.4424(12) 0.5392(5) 0.059(3) Uani d PG 0.50 A -1
H H35 0.7379 0.4085 0.5584 0.071 Uiso calc PR 0.50 A -1
C C36 0.6399(19) 0.4789(12) 0.4770(5) 0.089(3) Uani d PGD 0.50 A -1
H H36 0.7423 0.4700 0.4537 0.107 Uiso calc PR 0.50 A -1
C C37 0.5056(18) 0.5705(11) 0.3829(5) 0.123(5) Uani d PDU 0.50 A -1
H H37A 0.4289 0.6342 0.3792 0.185 Uiso calc PR 0.50 A -1
H H37B 0.4608 0.5000 0.3444 0.185 Uiso calc PR 0.50 A -1
H H37C 0.6355 0.6046 0.3820 0.185 Uiso calc PR 0.50 A -1
H H1O 0.055(7) 0.163(4) 0.2335(15) 0.109(19) Uiso d D 1 . .
H H2O 0.150(5) -0.183(3) 0.3934(17) 0.070(13) Uiso d D 1 . .
H H3N 0.484(7) 0.086(5) 0.0787(6) 0.106(17) Uiso d D 1 . .
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
C1 O1 H1O . . 105(3) ?
C11 O2 H2O . . 101(3) ?
C7 N1 C9 . . 122.8(2) ?
C17 N2 C19 . . 120.7(2) ?
C27 N3 C29 . . 127.2(2) ?
C27 N3 H3N . . 108(3) ?
C29 N3 H3N . . 124(3) ?
C10 N4 C30 . . 114.31(19) ?
C10 N4 C20 . . 114.1(2) ?
C30 N4 C20 . . 114.0(2) ?
O1 C1 C2 . . 119.6(2) ?
O1 C1 C6 . . 121.8(2) ?
C2 C1 C6 . . 118.6(2) ?
C3 C2 C1 . . 121.7(2) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C2 C3 C4 . . 119.1(2) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 121.1(2) ?
C5 C4 Cl1 . . 119.0(2) ?
C3 C4 Cl1 . . 119.8(2) ?
C4 C5 C6 . . 120.8(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 118.5(2) ?
C5 C6 C7 . . 121.4(2) ?
C1 C6 C7 . . 120.1(2) ?
N1 C7 C6 . . 116.9(2) ?
N1 C7 C8 . . 121.8(2) ?
C6 C7 C8 . . 121.3(2) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 110.2(2) ?
N1 C9 H9A . . 109.6 ?
C10 C9 H9A . . 109.6 ?
N1 C9 H9B . . 109.6 ?
C10 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
N4 C10 C9 . . 113.3(2) ?
N4 C10 H10A . . 108.9 ?
C9 C10 H10A . . 108.9 ?
N4 C10 H10B . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
O2 C11 C12 . . 118.0(2) ?
O2 C11 C16 . . 122.3(2) ?
C12 C11 C16 . . 119.7(2) ?
C13 C12 C11 . . 121.1(3) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C12 C13 C14 . . 118.9(2) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C15 C14 C13 . . 121.5(2) ?
C15 C14 Cl2 . . 118.5(2) ?
C13 C14 Cl2 . . 119.9(2) ?
C14 C15 C16 . . 120.6(2) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C11 . . 118.2(2) ?
C15 C16 C17 . . 121.0(2) ?
C11 C16 C17 . . 120.7(2) ?
N2 C17 C16 . . 116.6(2) ?
N2 C17 C18 . . 122.5(2) ?
C16 C17 C18 . . 120.8(2) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N2 C19 C20 . . 109.7(2) ?
N2 C19 H19A . . 109.7 ?
C20 C19 H19A . . 109.7 ?
N2 C19 H19B . . 109.7 ?
C20 C19 H19B . . 109.7 ?
H19A C19 H19B . . 108.2 ?
N4 C20 C19 . . 110.9(2) ?
N4 C20 H20A . . 109.4 ?
C19 C20 H20A . . 109.4 ?
N4 C20 H20B . . 109.4 ?
C19 C20 H20B . . 109.4 ?
H20A C20 H20B . . 108.0 ?
O3 C21 C22 . . 119.7(2) ?
O3 C21 C26 . . 121.8(2) ?
C22 C21 C26 . . 118.5(2) ?
C23 C22 C21 . . 121.6(2) ?
C23 C22 H22 . . 119.2 ?
C21 C22 H22 . . 119.2 ?
C22 C23 C24 . . 119.3(3) ?
C22 C23 H23 . . 120.4 ?
C24 C23 H23 . . 120.4 ?
C25 C24 C23 . . 121.3(2) ?
C25 C24 Cl3 . . 120.1(2) ?
C23 C24 Cl3 . . 118.6(2) ?
C24 C25 C26 . . 120.5(2) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C25 C26 C21 . . 118.7(2) ?
C25 C26 C27 . . 121.0(2) ?
C21 C26 C27 . . 120.3(2) ?
N3 C27 C26 . . 116.1(2) ?
N3 C27 C28 . . 123.3(2) ?
C26 C27 C28 . . 120.6(2) ?
C27 C28 H28A . . 109.5 ?
C27 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C27 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
N3 C29 C30 . . 109.8(2) ?
N3 C29 H29A . . 109.7 ?
C30 C29 H29A . . 109.7 ?
N3 C29 H29B . . 109.7 ?
C30 C29 H29B . . 109.7 ?
H29A C29 H29B . . 108.2 ?
N4 C30 C29 . . 113.8(2) ?
N4 C30 H30A . . 108.8 ?
C29 C30 H30A . . 108.8 ?
N4 C30 H30B . . 108.8 ?
C29 C30 H30B . . 108.8 ?
H30A C30 H30B . . 107.7 ?
C32 C31 C36 . . 120.0 ?
C32 C31 C37 . . 122.2(5) ?
C36 C31 C37 . . 117.8(5) ?
C33 C32 C31 . . 120.0 ?
C33 C32 H32 . . 120.0 ?
C31 C32 H32 . . 120.0 ?
C32 C33 C34 . . 120.0 ?
C32 C33 H33 . . 120.0 ?
C34 C33 H33 . . 120.0 ?
C33 C34 C35 . . 120.0 ?
C33 C34 H34 . . 120.0 ?
C35 C34 H34 . . 120.0 ?
C36 C35 C34 . . 120.0 ?
C36 C35 H35 . . 120.0 ?
C34 C35 H35 . . 120.0 ?
C35 C36 C31 . . 120.0 ?
C35 C36 H36 . . 120.0 ?
C31 C36 H36 . . 120.0 ?
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 C4 . 1.742(3) ?
Cl2 C14 . 1.746(3) ?
Cl3 C24 . 1.744(3) ?
O1 C1 . 1.321(3) ?
O1 H1O . 0.846(10) ?
O2 C11 . 1.343(3) ?
O2 H2O . 0.846(10) ?
O3 C21 . 1.318(3) ?
N1 C7 . 1.296(3) ?
N1 C9 . 1.459(3) ?
N2 C17 . 1.289(3) ?
N2 C19 . 1.465(3) ?
N3 C27 . 1.293(3) ?
N3 C29 . 1.457(3) ?
N3 H3N . 0.892(10) ?
N4 C10 . 1.459(3) ?
N4 C30 . 1.465(3) ?
N4 C20 . 1.468(3) ?
C1 C2 . 1.411(4) ?
C1 C6 . 1.426(3) ?
C2 C3 . 1.371(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.395(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.375(3) ?
C5 C6 . 1.405(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.472(3) ?
C7 C8 . 1.499(3) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.516(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.397(4) ?
C11 C16 . 1.414(4) ?
C12 C13 . 1.380(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.375(4) ?
C15 C16 . 1.402(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.476(3) ?
C17 C18 . 1.502(4) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 C20 . 1.504(4) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 C22 . 1.401(4) ?
C21 C26 . 1.431(4) ?
C22 C23 . 1.374(4) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.393(4) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.367(4) ?
C25 C26 . 1.409(3) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.463(4) ?
C27 C28 . 1.505(4) ?
C28 H28A . 0.9800 ?
C28 H28B . 0.9800 ?
C28 H28C . 0.9800 ?
C29 C30 . 1.517(4) ?
C29 H29A . 0.9900 ?
C29 H29B . 0.9900 ?
C30 H30A . 0.9900 ?
C30 H30B . 0.9900 ?
C31 C32 . 1.3900 ?
C31 C36 . 1.3900 ?
C31 C37 . 1.503(6) ?
C32 C33 . 1.3900 ?
C32 H32 . 0.9500 ?
C33 C34 . 1.3900 ?
C33 H33 . 0.9500 ?
C34 C35 . 1.3900 ?
C34 H34 . 0.9500 ?
C35 C36 . 1.3900 ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
C37 H37A . 0.9800 ?
C37 H37B . 0.9800 ?
C37 H37C . 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_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1o N1 . 0.850(10) 1.69(2) 2.486(3) 155(5) yes
O2 H2o N2 . 0.850(10) 1.70(2) 2.507(3) 158(4) yes
N3 H3n O3 . 0.890(10) 1.62(2) 2.474(3) 158(5) 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
O1 C1 C2 C3 . . . . -178.0(2) ?
C6 C1 C2 C3 . . . . 1.6(4) ?
C1 C2 C3 C4 . . . . 1.0(4) ?
C2 C3 C4 C5 . . . . -3.0(4) ?
C2 C3 C4 Cl1 . . . . 176.2(2) ?
C3 C4 C5 C6 . . . . 2.3(4) ?
Cl1 C4 C5 C6 . . . . -176.95(19) ?
C4 C5 C6 C1 . . . . 0.4(4) ?
C4 C5 C6 C7 . . . . -179.5(2) ?
O1 C1 C6 C5 . . . . 177.3(2) ?
C2 C1 C6 C5 . . . . -2.2(3) ?
O1 C1 C6 C7 . . . . -2.8(4) ?
C2 C1 C6 C7 . . . . 177.7(2) ?
C9 N1 C7 C6 . . . . 179.1(2) ?
C9 N1 C7 C8 . . . . -0.5(3) ?
C5 C6 C7 N1 . . . . -177.2(2) ?
C1 C6 C7 N1 . . . . 2.9(3) ?
C5 C6 C7 C8 . . . . 2.5(3) ?
C1 C6 C7 C8 . . . . -177.4(2) ?
C7 N1 C9 C10 . . . . -168.1(2) ?
C30 N4 C10 C9 . . . . -82.6(2) ?
C20 N4 C10 C9 . . . . 143.6(2) ?
N1 C9 C10 N4 . . . . -65.6(3) ?
O2 C11 C12 C13 . . . . -179.5(2) ?
C16 C11 C12 C13 . . . . 0.2(4) ?
C11 C12 C13 C14 . . . . 0.0(4) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
C12 C13 C14 Cl2 . . . . 177.42(19) ?
C13 C14 C15 C16 . . . . 0.0(4) ?
Cl2 C14 C15 C16 . . . . -177.57(18) ?
C14 C15 C16 C11 . . . . 0.2(3) ?
C14 C15 C16 C17 . . . . 178.3(2) ?
O2 C11 C16 C15 . . . . 179.4(2) ?
C12 C11 C16 C15 . . . . -0.4(3) ?
O2 C11 C16 C17 . . . . 1.4(4) ?
C12 C11 C16 C17 . . . . -178.4(2) ?
C19 N2 C17 C16 . . . . 175.8(2) ?
C19 N2 C17 C18 . . . . -3.4(4) ?
C15 C16 C17 N2 . . . . 179.9(2) ?
C11 C16 C17 N2 . . . . -2.1(3) ?
C15 C16 C17 C18 . . . . -0.9(3) ?
C11 C16 C17 C18 . . . . 177.1(2) ?
C17 N2 C19 C20 . . . . -176.4(2) ?
C10 N4 C20 C19 . . . . -121.4(2) ?
C30 N4 C20 C19 . . . . 104.7(2) ?
N2 C19 C20 N4 . . . . 170.4(2) ?
O3 C21 C22 C23 . . . . 175.9(2) ?
C26 C21 C22 C23 . . . . -3.4(4) ?
C21 C22 C23 C24 . . . . 0.8(4) ?
C22 C23 C24 C25 . . . . 2.4(4) ?
C22 C23 C24 Cl3 . . . . -177.2(2) ?
C23 C24 C25 C26 . . . . -2.8(4) ?
Cl3 C24 C25 C26 . . . . 176.78(19) ?
C24 C25 C26 C21 . . . . 0.0(4) ?
C24 C25 C26 C27 . . . . -178.9(2) ?
O3 C21 C26 C25 . . . . -176.3(2) ?
C22 C21 C26 C25 . . . . 3.0(3) ?
O3 C21 C26 C27 . . . . 2.6(3) ?
C22 C21 C26 C27 . . . . -178.1(2) ?
C29 N3 C27 C26 . . . . -175.5(2) ?
C29 N3 C27 C28 . . . . 4.6(4) ?
C25 C26 C27 N3 . . . . 176.8(2) ?
C21 C26 C27 N3 . . . . -2.2(3) ?
C25 C26 C27 C28 . . . . -3.3(3) ?
C21 C26 C27 C28 . . . . 177.8(2) ?
C27 N3 C29 C30 . . . . 109.5(3) ?
C10 N4 C30 C29 . . . . 125.5(2) ?
C20 N4 C30 C29 . . . . -100.7(2) ?
N3 C29 C30 N4 . . . . -72.8(3) ?
C36 C31 C32 C33 . . . . 0.0 ?
C37 C31 C32 C33 . . . . -177.9(9) ?
C31 C32 C33 C34 . . . . 0.0 ?
C32 C33 C34 C35 . . . . 0.0 ?
C33 C34 C35 C36 . . . . 0.0 ?
C34 C35 C36 C31 . . . . 0.0 ?
C32 C31 C36 C35 . . . . 0.0 ?
C37 C31 C36 C35 . . . . 177.9(8) ?
