#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224975.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_2224975
loop_
_publ_author_name
'Akkurt, Mehmet'
'Nassozi, Mebble'
'Çapan, Gültaze'
'Kocabalkanlı, Ayşe'
'Çelik, Ísmail'
'Büyükgüngör, Orhan'
_publ_section_title
2-[2-(2,6-Dichloroanilino)phenyl]-N'-(4-propylcyclohexylidene)acetohydrazide
_journal_coeditor_code           HB5287
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o256
_journal_page_last               o257
_journal_paper_doi               10.1107/S1600536809054695
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H27 Cl2 N3 O'
_chemical_formula_moiety         'C23 H27 Cl2 N3 O'
_chemical_formula_sum            'C23 H27 Cl2 N3 O'
_chemical_formula_weight         432.38
_chemical_name_systematic
;
2-[2-(2,6-Dichloroanilino)phenyl]-N'-(4-
propylcyclohexylidene)acetohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 118.098(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0235(6)
_cell_length_b                   15.2618(5)
_cell_length_c                   26.6255(12)
_cell_measurement_reflns_used    39814
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      1.56
_cell_volume                     4668.4(4)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            69169
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED3; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.476
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         9577
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1556
_refine_ls_R_factor_gt           0.0812
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1324P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2052
_refine_ls_wR_factor_ref         0.2471
_reflns_number_gt                4744
_reflns_number_total             9577
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5287.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224975
_cod_database_fobs_code          2224975
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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 Cl3 0.55339(12) 0.47497(7) 0.21299(7) 0.0961(5) Uani . . 1.000
Cl Cl4 0.35062(13) 0.76589(7) 0.24245(6) 0.0961(5) Uani . . 1.000
O O2 0.2070(3) 0.61054(15) 0.27547(13) 0.0687(10) Uani . . 1.000
N N4 0.3728(3) 0.57460(19) 0.23307(14) 0.0629(11) Uani . . 1.000
N N5 0.1122(3) 0.50946(18) 0.29889(14) 0.0619(11) Uani . . 1.000
N N6 0.0476(3) 0.5731(2) 0.30818(16) 0.0723(13) Uani . . 1.000
C C24 0.4513(3) 0.6241(2) 0.22301(16) 0.0591(11) Uani . . 1.000
C C25 0.4538(4) 0.7154(2) 0.22791(19) 0.0714(16) Uani . . 1.000
C C26 0.5337(5) 0.7657(3) 0.2219(2) 0.097(2) Uani . . 1.000
C C27 0.6145(5) 0.7280(3) 0.2095(3) 0.100(2) Uani . . 1.000
C C28 0.6163(4) 0.6386(3) 0.2052(2) 0.0875(19) Uani . . 1.000
C C29 0.5386(4) 0.5878(3) 0.21322(19) 0.0714(14) Uani . . 1.000
C C30 0.2970(3) 0.5115(2) 0.19509(19) 0.0624(13) Uani . . 1.000
C C31 0.2774(4) 0.5052(3) 0.1398(2) 0.0832(17) Uani . . 1.000
C C32 0.1971(5) 0.4428(5) 0.1038(3) 0.123(3) Uani . . 1.000
C C33 0.1421(6) 0.3871(5) 0.1238(4) 0.141(4) Uani . . 1.000
C C34 0.1628(5) 0.3935(3) 0.1788(3) 0.103(3) Uani . . 1.000
C C35 0.2404(4) 0.4557(2) 0.2156(2) 0.0680(15) Uani . . 1.000
C C36 0.2595(4) 0.4600(2) 0.2751(2) 0.0689(15) Uani . . 1.000
C C37 0.1899(3) 0.5338(2) 0.28315(16) 0.0544(11) Uani . . 1.000
C C38 -0.0211(5) 0.5513(3) 0.3267(3) 0.091(2) Uani . . 1.000
C C39 -0.0417(7) 0.4612(4) 0.3418(4) 0.1403(18) Uani . . 1.000
C C40 -0.0837(7) 0.4531(4) 0.3797(4) 0.1403(18) Uani . . 1.000
C C41 -0.1573(8) 0.5226(4) 0.3871(4) 0.1403(18) Uani . . 1.000
C C42 -0.1138(7) 0.6138(4) 0.3802(4) 0.1403(18) Uani . . 1.000
C C43 -0.0909(7) 0.6232(4) 0.3349(4) 0.1403(18) Uani . . 1.000
C C44A -0.1851(13) 0.5169(6) 0.4331(7) 0.1405(3) Uani . . 0.666(6)
C C45A -0.2286(11) 0.4326(6) 0.4477(6) 0.1405(3) Uani . . 0.666(6)
C C46A -0.3406(11) 0.4181(7) 0.3950(6) 0.1405(3) Uani . . 0.666(6)
C C46B -0.337(2) 0.3799(11) 0.4379(11) 0.1405(3) Uani . . 0.334(6)
C C44B -0.276(2) 0.4895(11) 0.3812(13) 0.1405(3) Uani . . 0.334(6)
C C45B -0.274(3) 0.3976(12) 0.4063(13) 0.1405(3) Uani . . 0.334(6)
Cl Cl1 0.65421(16) 0.86931(15) 0.46429(9) 0.1470(9) Uani . . 1.000
Cl Cl2 0.69658(17) 0.55357(12) 0.56388(8) 0.1386(8) Uani . . 1.000
O O1 0.8618(2) 0.68597(16) 0.67741(11) 0.0660(9) Uani . . 1.000
N N1 0.7624(3) 0.7387(2) 0.55967(14) 0.0720(12) Uani . . 1.000
N N2 1.0330(3) 0.73731(17) 0.74608(13) 0.0600(10) Uani . . 1.000
N N3 1.0550(3) 0.65711(19) 0.77439(16) 0.0744(11) Uani . . 1.000
C C1 0.6732(4) 0.7070(4) 0.50919(19) 0.0790(18) Uani . . 1.000
C C2 0.6183(4) 0.7609(4) 0.4604(2) 0.098(2) Uani . . 1.000
C C3 0.5347(6) 0.7271(7) 0.4093(3) 0.132(4) Uani . . 1.000
C C4 0.4974(6) 0.6461(9) 0.4068(4) 0.152(4) Uani . . 1.000
C C5 0.5440(6) 0.5910(6) 0.4539(4) 0.143(3) Uani . . 1.000
C C6 0.6327(5) 0.6232(4) 0.5040(2) 0.102(2) Uani . . 1.000
C C7 0.8708(3) 0.7650(3) 0.56500(17) 0.0646(12) Uani . . 1.000
C C8 0.9009(4) 0.7488(3) 0.52235(19) 0.0817(19) Uani . . 1.000
C C9 1.0070(5) 0.7718(4) 0.5287(2) 0.0962(19) Uani . . 1.000
C C10 1.0875(5) 0.8114(4) 0.5773(3) 0.104(2) Uani . . 1.000
C C11 1.0586(4) 0.8288(3) 0.6199(2) 0.0831(17) Uani . . 1.000
C C12 0.9510(3) 0.8072(2) 0.61494(16) 0.0616(12) Uani . . 1.000
C C13 0.9229(4) 0.8264(2) 0.66274(17) 0.0633(11) Uani . . 1.000
C C14 0.9359(3) 0.7440(2) 0.69641(16) 0.0541(11) Uani . . 1.000
C C15 1.1410(4) 0.6509(3) 0.82318(19) 0.0729(16) Uani . . 1.000
C C16 1.1645(6) 0.5615(3) 0.8499(3) 0.129(3) Uani . . 1.000
C C17 1.1834(6) 0.5634(4) 0.9097(3) 0.136(3) Uani . . 1.000
C C18 1.2791(6) 0.6281(4) 0.9464(2) 0.105(3) Uani . . 1.000
C C19 1.2429(7) 0.7183(4) 0.9183(3) 0.136(3) Uani . . 1.000
C C20 1.2220(5) 0.7205(4) 0.8578(2) 0.117(2) Uani . . 1.000
C C21 1.3058(8) 0.6285(7) 1.0070(3) 0.161(4) Uani . . 1.000
C C22 1.4223(12) 0.6681(8) 1.0492(4) 0.211(6) Uani . . 1.000
C C23 1.5268(10) 0.6037(11) 1.0633(4) 0.233(8) Uani . . 1.000
H H5A 0.10180 0.45490 0.30330 0.0740 Uiso calc R 1.000
H H28 0.67070 0.61230 0.19670 0.1050 Uiso calc R 1.000
H H26 0.53340 0.82620 0.22630 0.1170 Uiso calc R 1.000
H H27 0.66730 0.76250 0.20410 0.1190 Uiso calc R 1.000
H H4A 0.37050 0.58310 0.26450 0.0760 Uiso calc R 1.000
H H34 0.12460 0.35600 0.19200 0.1240 Uiso calc R 1.000
H H36A 0.34170 0.46900 0.30060 0.0830 Uiso calc R 1.000
H H36B 0.23700 0.40470 0.28500 0.0830 Uiso calc R 1.000
H H39A -0.09560 0.43200 0.30690 0.1690 Uiso calc R 1.000
H H31 0.31660 0.54160 0.12650 0.1000 Uiso calc R 1.000
H H32 0.18110 0.43920 0.06600 0.1470 Uiso calc R 1.000
H H33 0.09070 0.34490 0.09990 0.1690 Uiso calc R 1.000
H H41 -0.23290 0.51660 0.35300 0.1690 Uiso calc R 1.000
H H42A -0.17180 0.65690 0.37630 0.1690 Uiso calc R 1.000
H H42B -0.04330 0.62730 0.41490 0.1690 Uiso calc R 1.000
H H43A -0.04980 0.67800 0.33960 0.1690 Uiso calc R 1.000
H H43B -0.16470 0.62790 0.30040 0.1690 Uiso calc R 1.000
H H44A -0.24360 0.56130 0.42620 0.1690 Uiso calc . 0.666(6)
H H44B -0.11580 0.53440 0.46730 0.1690 Uiso calc . 0.666(6)
H H45A -0.17480 0.38450 0.45460 0.1690 Uiso calc . 0.666(6)
H H45B -0.24070 0.44020 0.48070 0.1690 Uiso calc . 0.666(6)
H H46A -0.37430 0.36360 0.39800 0.2110 Uiso calc . 0.666(6)
H H46B -0.32670 0.41600 0.36270 0.2110 Uiso calc . 0.666(6)
H H46C -0.39320 0.46520 0.39040 0.2110 Uiso calc . 0.666(6)
H H39B 0.03140 0.42940 0.35690 0.1690 Uiso calc R 1.000
H H40A -0.01700 0.44400 0.41680 0.1690 Uiso calc R 1.000
H H40B -0.12860 0.39930 0.37020 0.1690 Uiso calc R 1.000
H H44C -0.30320 0.53140 0.39980 0.1690 Uiso calc . 0.334(6)
H H44D -0.33270 0.48880 0.34110 0.1690 Uiso calc . 0.334(6)
H H45C -0.30180 0.35630 0.37490 0.1690 Uiso calc . 0.334(6)
H H45D -0.19290 0.38330 0.43120 0.1690 Uiso calc . 0.334(6)
H H46D -0.36230 0.31990 0.43240 0.2110 Uiso calc . 0.334(6)
H H46E -0.40380 0.41780 0.42450 0.2110 Uiso calc . 0.334(6)
H H46F -0.28720 0.39040 0.47770 0.2110 Uiso calc . 0.334(6)
H H1 0.75110 0.74250 0.58890 0.0870 Uiso calc R 1.000
H H2 1.08010 0.78080 0.76000 0.0720 Uiso calc R 1.000
H H3 0.50470 0.76150 0.37660 0.1590 Uiso calc R 1.000
H H4 0.43830 0.62520 0.37250 0.1820 Uiso calc R 1.000
H H5 0.51620 0.53430 0.45180 0.1720 Uiso calc R 1.000
H H8 0.84750 0.72170 0.48890 0.0980 Uiso calc R 1.000
H H9 1.02510 0.76040 0.49950 0.1150 Uiso calc R 1.000
H H10 1.16040 0.82640 0.58150 0.1240 Uiso calc R 1.000
H H11 1.11320 0.85590 0.65310 0.1000 Uiso calc R 1.000
H H13A 0.97520 0.87120 0.68750 0.0760 Uiso calc R 1.000
H H13B 0.84380 0.84820 0.64720 0.0760 Uiso calc R 1.000
H H16A 1.09920 0.52350 0.82740 0.1560 Uiso calc R 1.000
H H16B 1.23290 0.53710 0.84950 0.1560 Uiso calc R 1.000
H H17A 1.20460 0.50530 0.92600 0.1630 Uiso calc R 1.000
H H17B 1.11140 0.57990 0.90960 0.1630 Uiso calc R 1.000
H H18 1.35020 0.61090 0.94500 0.1260 Uiso calc R 1.000
H H19A 1.17240 0.73640 0.91910 0.1630 Uiso calc R 1.000
H H19B 1.30340 0.76030 0.94040 0.1630 Uiso calc R 1.000
H H20A 1.19010 0.77710 0.84130 0.1400 Uiso calc R 1.000
H H20B 1.29550 0.71330 0.85740 0.1400 Uiso calc R 1.000
H H21A 1.30320 0.56860 1.01840 0.1930 Uiso calc R 1.000
H H21B 1.24450 0.66050 1.01000 0.1930 Uiso calc R 1.000
H H22A 1.42000 0.68270 1.08410 0.2540 Uiso calc R 1.000
H H22B 1.43490 0.72190 1.03350 0.2540 Uiso calc R 1.000
H H23A 1.54970 0.57660 1.09960 0.3460 Uiso calc R 1.000
H H23B 1.59130 0.63580 1.06450 0.3460 Uiso calc R 1.000
H H23C 1.50300 0.55940 1.03440 0.3460 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
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 -3 -18 0.0421
-1 0 2 0.0690
29 4 19 0.1647
15 29 29 0.2760
4 -9 -2 0.3050
-4 -18 -1 0.2953
-2 3 24 0.1010
-4 -6 21 0.2520
-3 0 4 0.0820
-3 11 26 0.2117
-9 21 1 0.2970
4 1 -30 0.1177
8 9 -18 0.3132
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
C24 N4 C30 . . . 124.2(3) no
N6 N5 C37 . . . 118.8(3) no
N5 N6 C38 . . . 119.5(4) no
C24 N4 H4A . . . 118.00 no
C30 N4 H4A . . . 118.00 no
C37 N5 H5A . . . 121.00 no
N6 N5 H5A . . . 121.00 no
C1 N1 C7 . . . 122.7(4) no
N3 N2 C14 . . . 117.4(3) no
N2 N3 C15 . . . 118.8(4) no
C7 N1 H1 . . . 119.00 no
C1 N1 H1 . . . 119.00 no
N3 N2 H2 . . . 121.00 no
C14 N2 H2 . . . 121.00 no
N4 C24 C25 . . . 120.6(4) no
N4 C24 C29 . . . 123.8(3) no
C25 C24 C29 . . . 115.3(4) no
Cl4 C25 C26 . . . 119.2(3) no
C24 C25 C26 . . . 122.4(5) no
Cl4 C25 C24 . . . 118.3(4) no
C25 C26 C27 . . . 120.5(4) no
C26 C27 C28 . . . 118.9(6) no
C27 C28 C29 . . . 120.5(5) no
Cl3 C29 C28 . . . 118.1(4) no
C24 C29 C28 . . . 122.1(4) no
Cl3 C29 C24 . . . 119.8(4) no
N4 C30 C35 . . . 117.2(4) no
N4 C30 C31 . . . 122.1(4) no
C31 C30 C35 . . . 120.7(4) no
C30 C31 C32 . . . 118.8(5) no
C31 C32 C33 . . . 120.8(7) no
C32 C33 C34 . . . 119.9(7) no
C33 C34 C35 . . . 121.0(6) no
C30 C35 C36 . . . 122.5(4) no
C30 C35 C34 . . . 118.8(5) no
C34 C35 C36 . . . 118.7(5) no
C35 C36 C37 . . . 111.8(3) no
O2 C37 N5 . . . 123.3(4) no
N5 C37 C36 . . . 115.7(3) no
O2 C37 C36 . . . 121.0(4) no
N6 C38 C39 . . . 127.1(6) no
N6 C38 C43 . . . 117.1(5) no
C39 C38 C43 . . . 115.8(7) no
C38 C39 C40 . . . 118.0(6) no
C39 C40 C41 . . . 122.5(7) no
C42 C41 C44A . . . 114.2(7) no
C42 C41 C44B . . . 132.8(10) no
C40 C41 C42 . . . 109.1(8) no
C40 C41 C44A . . . 120.1(8) no
C40 C41 C44B . . . 114.9(9) no
C41 C42 C43 . . . 116.1(7) no
C38 C43 C42 . . . 116.4(6) no
C41 C44A C45A . . . 122.8(10) no
C41 C44B C45B . . . 116(2) no
C44A C45A C46A . . . 101.6(11) no
C44B C45B C46B . . . 121(2) no
C25 C26 H26 . . . 120.00 no
C27 C26 H26 . . . 120.00 no
C28 C27 H27 . . . 121.00 no
C26 C27 H27 . . . 121.00 no
C29 C28 H28 . . . 120.00 no
C27 C28 H28 . . . 120.00 no
C32 C31 H31 . . . 121.00 no
C30 C31 H31 . . . 121.00 no
C31 C32 H32 . . . 120.00 no
C33 C32 H32 . . . 120.00 no
C32 C33 H33 . . . 120.00 no
C34 C33 H33 . . . 120.00 no
C35 C34 H34 . . . 120.00 no
C33 C34 H34 . . . 120.00 no
C35 C36 H36B . . . 109.00 no
C35 C36 H36A . . . 109.00 no
H36A C36 H36B . . . 108.00 no
C37 C36 H36B . . . 109.00 no
C37 C36 H36A . . . 109.00 no
C40 C39 H39A . . . 108.00 no
H39A C39 H39B . . . 107.00 no
C38 C39 H39B . . . 108.00 no
C40 C39 H39B . . . 108.00 no
C38 C39 H39A . . . 108.00 no
C39 C40 H40A . . . 107.00 no
C39 C40 H40B . . . 107.00 no
H40A C40 H40B . . . 107.00 no
C41 C40 H40B . . . 107.00 no
C41 C40 H40A . . . 107.00 no
C44A C41 H41 . . . 104.00 no
C44B C41 H41 . . . 50.00 no
C42 C41 H41 . . . 104.00 no
C40 C41 H41 . . . 104.00 no
C43 C42 H42B . . . 108.00 no
C41 C42 H42A . . . 108.00 no
C41 C42 H42B . . . 108.00 no
H42A C42 H42B . . . 107.00 no
C43 C42 H42A . . . 108.00 no
C38 C43 H43B . . . 108.00 no
C38 C43 H43A . . . 108.00 no
C42 C43 H43A . . . 108.00 no
C42 C43 H43B . . . 108.00 no
H43A C43 H43B . . . 107.00 no
C45A C44A H44B . . . 107.00 no
H44A C44A H44B . . . 107.00 no
C41 C44A H44B . . . 107.00 no
C45A C44A H44A . . . 107.00 no
C41 C44A H44A . . . 107.00 no
C45B C44B H41 . . . 132.00 no
H41 C44B H44C . . . 119.00 no
C41 C44B H44D . . . 109.00 no
C45B C44B H44D . . . 108.00 no
H44C C44B H44D . . . 107.00 no
C41 C44B H44C . . . 108.00 no
H41 C44B H44D . . . 70.00 no
C45B C44B H44C . . . 108.00 no
H45A C45A H45B . . . 109.00 no
C46A C45A H45A . . . 111.00 no
C46A C45A H45B . . . 111.00 no
C44A C45A H45B . . . 112.00 no
C44A C45A H45A . . . 111.00 no
C44B C45B H45C . . . 107.00 no
C44B C45B H45D . . . 107.00 no
C46B C45B H45C . . . 107.00 no
C46B C45B H45D . . . 107.00 no
H45C C45B H45D . . . 107.00 no
C45A C46A H46A . . . 109.00 no
H46A C46A H46B . . . 109.00 no
H46B C46A H46C . . . 110.00 no
C45A C46A H46C . . . 109.00 no
H46A C46A H46C . . . 109.00 no
C45A C46A H46B . . . 110.00 no
C45B C46B H46D . . . 110.00 no
H46E C46B H46F . . . 109.00 no
C45B C46B H46E . . . 109.00 no
C45B C46B H46F . . . 110.00 no
H46D C46B H46E . . . 109.00 no
H46D C46B H46F . . . 109.00 no
N1 C1 C2 . . . 121.2(5) no
N1 C1 C6 . . . 122.2(4) no
C2 C1 C6 . . . 116.6(5) no
Cl1 C2 C3 . . . 119.2(5) no
C1 C2 C3 . . . 120.7(6) no
Cl1 C2 C1 . . . 120.1(4) no
C2 C3 C4 . . . 120.1(8) no
C3 C4 C5 . . . 121.9(9) no
C4 C5 C6 . . . 117.9(8) no
Cl2 C6 C5 . . . 118.9(6) no
C1 C6 C5 . . . 122.6(6) no
Cl2 C6 C1 . . . 118.5(4) no
N1 C7 C12 . . . 119.3(4) no
C8 C7 C12 . . . 119.1(4) no
N1 C7 C8 . . . 121.5(4) no
C7 C8 C9 . . . 121.1(4) no
C8 C9 C10 . . . 121.0(6) no
C9 C10 C11 . . . 118.7(6) no
C10 C11 C12 . . . 122.2(5) no
C7 C12 C13 . . . 121.4(4) no
C11 C12 C13 . . . 120.7(4) no
C7 C12 C11 . . . 117.9(4) no
C12 C13 C14 . . . 109.6(3) no
N2 C14 C13 . . . 116.2(3) no
O1 C14 N2 . . . 123.1(3) no
O1 C14 C13 . . . 120.7(4) no
N3 C15 C20 . . . 128.2(4) no
C16 C15 C20 . . . 115.6(5) no
N3 C15 C16 . . . 116.2(5) no
C15 C16 C17 . . . 112.5(5) no
C16 C17 C18 . . . 111.7(6) no
C17 C18 C19 . . . 107.3(5) no
C17 C18 C21 . . . 113.7(7) no
C19 C18 C21 . . . 112.9(6) no
C18 C19 C20 . . . 113.7(5) no
C15 C20 C19 . . . 111.7(5) no
C18 C21 C22 . . . 116.5(9) no
C21 C22 C23 . . . 112.1(10) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 119.00 no
C5 C4 H4 . . . 119.00 no
C4 C5 H5 . . . 121.00 no
C6 C5 H5 . . . 121.00 no
C7 C8 H8 . . . 119.00 no
C9 C8 H8 . . . 120.00 no
C8 C9 H9 . . . 119.00 no
C10 C9 H9 . . . 119.00 no
C9 C10 H10 . . . 121.00 no
C11 C10 H10 . . . 121.00 no
C10 C11 H11 . . . 119.00 no
C12 C11 H11 . . . 119.00 no
C12 C13 H13A . . . 110.00 no
C12 C13 H13B . . . 110.00 no
C14 C13 H13A . . . 110.00 no
C14 C13 H13B . . . 110.00 no
H13A C13 H13B . . . 108.00 no
C15 C16 H16A . . . 109.00 no
C15 C16 H16B . . . 109.00 no
C17 C16 H16A . . . 109.00 no
C17 C16 H16B . . . 109.00 no
H16A C16 H16B . . . 108.00 no
C16 C17 H17A . . . 109.00 no
C16 C17 H17B . . . 109.00 no
C18 C17 H17A . . . 109.00 no
C18 C17 H17B . . . 109.00 no
H17A C17 H17B . . . 108.00 no
C17 C18 H18 . . . 108.00 no
C19 C18 H18 . . . 108.00 no
C21 C18 H18 . . . 108.00 no
C18 C19 H19A . . . 109.00 no
C18 C19 H19B . . . 109.00 no
C20 C19 H19A . . . 109.00 no
C20 C19 H19B . . . 109.00 no
H19A C19 H19B . . . 108.00 no
C15 C20 H20A . . . 109.00 no
C15 C20 H20B . . . 109.00 no
C19 C20 H20A . . . 109.00 no
C19 C20 H20B . . . 109.00 no
H20A C20 H20B . . . 108.00 no
C18 C21 H21A . . . 108.00 no
C18 C21 H21B . . . 108.00 no
C22 C21 H21A . . . 108.00 no
C22 C21 H21B . . . 108.00 no
H21A C21 H21B . . . 107.00 no
C21 C22 H22A . . . 109.00 no
C21 C22 H22B . . . 109.00 no
C23 C22 H22A . . . 109.00 no
C23 C22 H22B . . . 109.00 no
H22A C22 H22B . . . 108.00 no
C22 C23 H23A . . . 109.00 no
C22 C23 H23B . . . 110.00 no
C22 C23 H23C . . . 109.00 no
H23A C23 H23B . . . 110.00 no
H23A C23 H23C . . . 109.00 no
H23B C23 H23C . . . 109.00 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
Cl3 C29 . . 1.733(5) no
Cl4 C25 . . 1.743(6) no
Cl1 C2 . . 1.709(6) no
Cl2 C6 . . 1.765(6) no
O2 C37 . . 1.227(4) no
O1 C14 . . 1.230(5) no
N4 C24 . . 1.395(6) no
N4 C30 . . 1.409(5) no
N5 N6 . . 1.381(5) no
N5 C37 . . 1.318(6) no
N6 C38 . . 1.253(8) no
N4 H4A . . 0.8600 no
N5 H5A . . 0.8600 no
N1 C1 . . 1.385(6) no
N1 C7 . . 1.409(6) no
N2 N3 . . 1.395(4) no
N2 C14 . . 1.335(5) no
N3 C15 . . 1.257(6) no
N1 H1 . . 0.8600 no
N2 H2 . . 0.8600 no
C24 C29 . . 1.395(7) no
C24 C25 . . 1.398(4) no
C25 C26 . . 1.362(8) no
C26 C27 . . 1.369(10) no
C27 C28 . . 1.370(7) no
C28 C29 . . 1.369(8) no
C30 C31 . . 1.374(7) no
C30 C35 . . 1.395(6) no
C31 C32 . . 1.405(9) no
C32 C33 . . 1.371(11) no
C33 C34 . . 1.362(12) no
C34 C35 . . 1.396(7) no
C35 C36 . . 1.485(7) no
C36 C37 . . 1.523(6) no
C38 C43 . . 1.505(10) no
C38 C39 . . 1.492(9) no
C39 C40 . . 1.361(14) no
C40 C41 . . 1.504(13) no
C41 C44B . . 1.56(3) no
C41 C42 . . 1.546(10) no
C41 C44A . . 1.43(2) no
C42 C43 . . 1.380(14) no
C44A C45A . . 1.528(17) no
C44B C45B . . 1.55(3) no
C45A C46A . . 1.49(2) no
C45B C46B . . 1.45(5) no
C26 H26 . . 0.9300 no
C27 H27 . . 0.9300 no
C28 H28 . . 0.9300 no
C31 H31 . . 0.9300 no
C32 H32 . . 0.9300 no
C33 H33 . . 0.9300 no
C34 H34 . . 0.9300 no
C36 H36B . . 0.9700 no
C36 H36A . . 0.9700 no
C39 H39B . . 0.9700 no
C39 H39A . . 0.9700 no
C40 H40B . . 0.9700 no
C40 H40A . . 0.9700 no
C41 H41 . . 0.9800 no
C42 H42B . . 0.9700 no
C42 H42A . . 0.9700 no
C43 H43A . . 0.9700 no
C43 H43B . . 0.9700 no
C44A H44A . . 0.9700 no
C44A H44B . . 0.9700 no
C44B H44C . . 0.9700 no
C44B H44D . . 0.9700 no
C44B H41 . . 1.2000 no
C45A H45B . . 0.9700 no
C45A H45A . . 0.9700 no
C45B H45C . . 0.9700 no
C45B H45D . . 0.9700 no
C46A H46C . . 0.9600 no
C46A H46A . . 0.9600 no
C46A H46B . . 0.9600 no
C46B H46E . . 0.9600 no
C46B H46F . . 0.9600 no
C46B H46D . . 0.9600 no
C1 C2 . . 1.414(7) no
C1 C6 . . 1.365(9) no
C2 C3 . . 1.381(9) no
C3 C4 . . 1.318(17) no
C4 C5 . . 1.390(15) no
C5 C6 . . 1.380(11) no
C7 C12 . . 1.402(6) no
C7 C8 . . 1.387(7) no
C8 C9 . . 1.357(9) no
C9 C10 . . 1.364(9) no
C10 C11 . . 1.379(9) no
C11 C12 . . 1.384(7) no
C12 C13 . . 1.509(6) no
C13 C14 . . 1.507(5) no
C15 C20 . . 1.475(8) no
C15 C16 . . 1.502(7) no
C16 C17 . . 1.492(10) no
C17 C18 . . 1.528(10) no
C18 C21 . . 1.482(9) no
C18 C19 . . 1.531(9) no
C19 C20 . . 1.502(9) no
C21 C22 . . 1.524(16) no
C22 C23 . . 1.57(2) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C8 H8 . . 0.9300 no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C13 H13A . . 0.9700 no
C13 H13B . . 0.9700 no
C16 H16A . . 0.9700 no
C16 H16B . . 0.9700 no
C17 H17A . . 0.9700 no
C17 H17B . . 0.9700 no
C18 H18 . . 0.9800 no
C19 H19A . . 0.9700 no
C19 H19B . . 0.9700 no
C20 H20A . . 0.9700 no
C20 H20B . . 0.9700 no
C21 H21A . . 0.9700 no
C21 H21B . . 0.9700 no
C22 H22A . . 0.9700 no
C22 H22B . . 0.9700 no
C23 H23A . . 0.9600 no
C23 H23B . . 0.9600 no
C23 H23C . . 0.9600 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
N1 H1 O1 . 0.86 2.28 2.886(4) 128 yes
N2 H2 O2 4_665 0.86 2.24 3.077(5) 165 yes
N4 H4A O2 . 0.86 2.32 2.921(6) 127 yes
N5 H5A O1 3_666 0.86 2.21 3.034(4) 161 yes
C20 H20A O2 4_665 0.97 2.53 3.330(6) 139 yes
C36 H36B O1 3_666 0.97 2.41 3.307(5) 155 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
C24 N4 C30 C35 . . . . 167.8(4) no
C30 N4 C24 C25 . . . . 128.2(4) no
C30 N4 C24 C29 . . . . -58.4(6) no
C24 N4 C30 C31 . . . . -13.1(6) no
C37 N5 N6 C38 . . . . -175.4(5) no
N6 N5 C37 O2 . . . . -1.1(6) no
N6 N5 C37 C36 . . . . 178.6(4) no
N5 N6 C38 C43 . . . . -178.8(6) no
N5 N6 C38 C39 . . . . 1.3(10) no
C1 N1 C7 C8 . . . . -9.6(7) no
C7 N1 C1 C6 . . . . 115.8(6) no
C1 N1 C7 C12 . . . . 171.5(4) no
C7 N1 C1 C2 . . . . -65.1(7) no
N3 N2 C14 O1 . . . . 6.3(6) no
C14 N2 N3 C15 . . . . -174.7(5) no
N3 N2 C14 C13 . . . . -171.4(4) no
N2 N3 C15 C20 . . . . 3.9(8) no
N2 N3 C15 C16 . . . . -176.3(5) no
N4 C24 C25 Cl4 . . . . -4.0(5) no
C25 C24 C29 C28 . . . . -4.2(6) no
N4 C24 C29 Cl3 . . . . 0.2(6) no
N4 C24 C25 C26 . . . . 175.9(4) no
C29 C24 C25 Cl4 . . . . -178.0(3) no
C25 C24 C29 Cl3 . . . . 174.0(3) no
C29 C24 C25 C26 . . . . 1.9(6) no
N4 C24 C29 C28 . . . . -178.0(4) no
C24 C25 C26 C27 . . . . 1.3(8) no
Cl4 C25 C26 C27 . . . . -178.9(5) no
C25 C26 C27 C28 . . . . -2.3(9) no
C26 C27 C28 C29 . . . . -0.1(9) no
C27 C28 C29 C24 . . . . 3.4(8) no
C27 C28 C29 Cl3 . . . . -174.8(5) no
N4 C30 C31 C32 . . . . -177.6(5) no
C31 C30 C35 C36 . . . . 179.7(4) no
C35 C30 C31 C32 . . . . 1.5(7) no
N4 C30 C35 C34 . . . . 178.7(4) no
N4 C30 C35 C36 . . . . -1.2(6) no
C31 C30 C35 C34 . . . . -0.4(7) no
C30 C31 C32 C33 . . . . -2.2(10) no
C31 C32 C33 C34 . . . . 1.8(12) no
C32 C33 C34 C35 . . . . -0.6(11) no
C33 C34 C35 C36 . . . . 179.8(6) no
C33 C34 C35 C30 . . . . -0.1(9) no
C30 C35 C36 C37 . . . . 80.0(6) no
C34 C35 C36 C37 . . . . -100.0(5) no
C35 C36 C37 O2 . . . . -61.9(5) no
C35 C36 C37 N5 . . . . 118.4(4) no
C39 C38 C43 C42 . . . . 34.4(11) no
N6 C38 C43 C42 . . . . -145.6(8) no
N6 C38 C39 C40 . . . . 156.0(8) no
C43 C38 C39 C40 . . . . -23.9(12) no
C38 C39 C40 C41 . . . . 27.6(14) no
C39 C40 C41 C42 . . . . -36.2(12) no
C39 C40 C41 C44A . . . . -170.9(11) no
C44A C41 C42 C43 . . . . -177.3(11) no
C40 C41 C42 C43 . . . . 45.1(11) no
C42 C41 C44A C45A . . . . -179.5(12) no
C40 C41 C44A C45A . . . . -47(2) no
C41 C42 C43 C38 . . . . -46.4(12) no
C41 C44A C45A C46A . . . . -62.9(18) no
C2 C1 C6 Cl2 . . . . -179.1(5) no
N1 C1 C6 Cl2 . . . . 0.1(8) no
N1 C1 C6 C5 . . . . -179.9(7) no
N1 C1 C2 Cl1 . . . . -4.7(8) no
N1 C1 C2 C3 . . . . 175.8(6) no
C6 C1 C2 Cl1 . . . . 174.5(5) no
C6 C1 C2 C3 . . . . -5.0(9) no
C2 C1 C6 C5 . . . . 0.9(10) no
C1 C2 C3 C4 . . . . 6.3(12) no
Cl1 C2 C3 C4 . . . . -173.2(7) no
C2 C3 C4 C5 . . . . -3.3(14) no
C3 C4 C5 C6 . . . . -0.8(14) no
C4 C5 C6 C1 . . . . 2.0(12) no
C4 C5 C6 Cl2 . . . . -178.1(7) no
C8 C7 C12 C11 . . . . -1.7(6) no
C8 C7 C12 C13 . . . . -179.9(4) no
C12 C7 C8 C9 . . . . 1.1(7) no
N1 C7 C12 C11 . . . . 177.3(4) no
N1 C7 C8 C9 . . . . -177.8(5) no
N1 C7 C12 C13 . . . . -1.0(6) no
C7 C8 C9 C10 . . . . 0.2(8) no
C8 C9 C10 C11 . . . . -0.8(9) no
C9 C10 C11 C12 . . . . 0.2(8) no
C10 C11 C12 C7 . . . . 1.1(7) no
C10 C11 C12 C13 . . . . 179.3(4) no
C11 C12 C13 C14 . . . . -100.4(4) no
C7 C12 C13 C14 . . . . 77.9(5) no
C12 C13 C14 O1 . . . . -75.5(5) no
C12 C13 C14 N2 . . . . 102.3(4) no
N3 C15 C16 C17 . . . . -131.7(6) no
C20 C15 C16 C17 . . . . 48.2(9) no
N3 C15 C20 C19 . . . . 133.7(6) no
C16 C15 C20 C19 . . . . -46.1(8) no
C15 C16 C17 C18 . . . . -54.2(9) no
C16 C17 C18 C19 . . . . 57.9(8) no
C16 C17 C18 C21 . . . . -176.6(7) no
C17 C18 C19 C20 . . . . -57.3(9) no
C21 C18 C19 C20 . . . . 176.7(7) no
C17 C18 C21 C22 . . . . 161.5(8) no
C19 C18 C21 C22 . . . . -76.0(11) no
C18 C19 C20 C15 . . . . 51.8(9) no
C18 C21 C22 C23 . . . . -77.6(11) no
