#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221277.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_2221277
loop_
_publ_author_name
'Zhang, Dehua'
'Zhang, Xiaoyan'
'Guo, Lijuan'
_publ_section_title
;(Z)-Ethyl
 3-[bis(4-chloro-3-ethyl-1-methyl-1H-pyrazol-5-ylcarbonyl)amino]-3-(4-chlorophenyl)-2-cyanopropanoate
;
_journal_coeditor_code           BQ2113
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o887
_journal_paper_doi               10.1107/S1600536809008988
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C26 H25 Cl3 N6 O4'
_chemical_formula_moiety         'C26 H25 Cl3 N6 O4'
_chemical_formula_sum            'C26 H25 Cl3 N6 O4'
_chemical_formula_weight         591.87
_chemical_name_systematic
;
(Z)-Ethyl 3-[bis(4-chloro-3-ethyl-1-methyl-1H-pyrazol-5-
ylcarbonyl)amino]-3-(4-chlorophenyl)-2-cyanopropanoate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.671(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7277(3)
_cell_length_b                   16.1476(5)
_cell_length_c                   17.3109(5)
_cell_measurement_reflns_used    2499
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.19
_cell_measurement_theta_min      2.36
_cell_volume                     2857.22(15)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18010
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5600
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0646
_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)+(0.0809P)²+0.6207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                3595
_reflns_number_total             5600
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2113.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2857.21(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221277
_cod_database_fobs_code          2221277
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C C1 0.5605(5) 1.1026(3) 0.0809(3) 0.1016(16) Uani d . 1 . .
H H1A 0.4925 1.0742 0.0957 0.152 Uiso calc R 1 . .
H H1B 0.5308 1.1155 0.0241 0.152 Uiso calc R 1 . .
H H1C 0.5823 1.1529 0.1116 0.152 Uiso calc R 1 . .
C C2 0.6797(4) 1.0481(3) 0.0986(2) 0.0819(12) Uani d . 1 . .
H H2A 0.6586 0.9991 0.0647 0.098 Uiso calc R 1 . .
H H2B 0.7485 1.0777 0.0846 0.098 Uiso calc R 1 . .
C C3 0.7296(4) 1.0218(2) 0.1857(2) 0.0600(9) Uani d . 1 . .
C C4 0.7612(3) 0.9620(2) 0.30584(19) 0.0464(8) Uani d . 1 . .
C C5 0.6770(3) 0.9653(2) 0.22757(19) 0.0493(8) Uani d . 1 . .
C C6 0.9700(4) 1.0424(3) 0.3756(3) 0.0843(13) Uani d . 1 . .
H H6A 0.9397 1.0573 0.4205 0.126 Uiso calc R 1 . .
H H6B 1.0117 1.0893 0.3598 0.126 Uiso calc R 1 . .
H H6C 1.0316 0.9977 0.3913 0.126 Uiso calc R 1 . .
C C7 0.7665(3) 0.91302(19) 0.37875(18) 0.0446(7) Uani d . 1 . .
C C8 0.5482(3) 0.96134(19) 0.37330(17) 0.0416(7) Uani d . 1 . .
C C9 0.6001(3) 1.0460(2) 0.39174(18) 0.0434(7) Uani d . 1 . .
C C10 0.6964(3) 1.0615(2) 0.46510(19) 0.0518(8) Uani d . 1 . .
H H10 0.7256 1.0188 0.5023 0.062 Uiso calc R 1 . .
C C11 0.7483(4) 1.1396(3) 0.4827(2) 0.0675(10) Uani d . 1 . .
H H11 0.8112 1.1505 0.5320 0.081 Uiso calc R 1 . .
C C12 0.7058(4) 1.2011(2) 0.4263(3) 0.0680(11) Uani d . 1 . .
C C13 0.6112(4) 1.1884(2) 0.3540(2) 0.0641(10) Uani d . 1 . .
H H13 0.5830 1.2315 0.3173 0.077 Uiso calc R 1 . .
C C14 0.5585(3) 1.1101(2) 0.3366(2) 0.0508(8) Uani d . 1 . .
H H14 0.4946 1.1003 0.2875 0.061 Uiso calc R 1 . .
C C15 0.4182(3) 0.9445(2) 0.34745(18) 0.0452(7) Uani d . 1 . .
C C16 0.3269(3) 1.0107(2) 0.3428(2) 0.0504(8) Uani d . 1 . .
C C17 0.3619(3) 0.8606(3) 0.3228(2) 0.0543(9) Uani d . 1 A .
C C20 0.6330(3) 0.8337(2) 0.44703(19) 0.0479(8) Uani d . 1 . .
C C21 0.7060(3) 0.7572(2) 0.44792(19) 0.0491(8) Uani d . 1 B .
C C22 0.7445(4) 0.7138(2) 0.3903(2) 0.0604(9) Uani d . 1 B .
C C23 0.8073(5) 0.6430(3) 0.4273(3) 0.0923(14) Uani d D 1 . .
C C18 0.1713(16) 0.7798(7) 0.2921(11) 0.077(5) Uani d PD 0.51 A 1
H H18A 0.2076 0.7451 0.2585 0.093 Uiso calc PR 0.51 A 1
H H18B 0.1817 0.7522 0.3435 0.093 Uiso calc PR 0.51 A 1
C C19 0.0337(14) 0.7994(15) 0.2510(13) 0.159(9) Uani d PD 0.51 A 1
H H19A -0.0021 0.8289 0.2876 0.238 Uiso calc PR 0.51 A 1
H H19B -0.0145 0.7491 0.2343 0.238 Uiso calc PR 0.51 A 1
H H19C 0.0275 0.8332 0.2044 0.238 Uiso calc PR 0.51 A 1
C C24 0.8921(8) 0.5836(4) 0.3948(5) 0.089(2) Uani d PD 0.71 B 1
H H24A 0.8987 0.6030 0.3431 0.107 Uiso calc PR 0.71 B 1
H H24B 0.9794 0.5793 0.4327 0.107 Uiso calc PR 0.71 B 1
C C25 0.8247(9) 0.5025(4) 0.3851(6) 0.127(3) Uani d PD 0.71 B 1
H H25A 0.8184 0.4845 0.4366 0.191 Uiso calc PR 0.71 B 1
H H25B 0.8735 0.4626 0.3650 0.191 Uiso calc PR 0.71 B 1
H H25C 0.7385 0.5079 0.3474 0.191 Uiso calc PR 0.71 B 1
C C26 0.7327(5) 0.7275(3) 0.5962(2) 0.0921(14) Uani d . 1 B .
H H26A 0.6420 0.7356 0.5914 0.138 Uiso calc R 1 . .
H H26B 0.7811 0.7764 0.6186 0.138 Uiso calc R 1 . .
H H26C 0.7660 0.6812 0.6312 0.138 Uiso calc R 1 . .
Cl Cl1 0.53576(9) 0.91015(6) 0.18601(5) 0.0620(3) Uani d . 1 . .
Cl Cl2 0.77506(16) 1.29995(8) 0.44793(10) 0.1232(6) Uani d . 1 . .
Cl Cl3 0.71509(10) 0.73843(6) 0.29021(5) 0.0700(3) Uani d . 1 . .
N N1 0.8404(3) 1.0541(2) 0.23522(19) 0.0693(9) Uani d . 1 . .
N N2 0.8587(3) 1.01616(19) 0.30722(17) 0.0596(8) Uani d . 1 . .
N N3 0.6432(2) 0.89762(15) 0.39096(14) 0.0414(6) Uani d . 1 . .
N N4 0.2531(3) 1.0622(2) 0.3401(2) 0.0723(9) Uani d . 1 . .
N N5 0.8081(4) 0.6418(2) 0.5053(2) 0.0992(13) Uani d . 1 B .
N N6 0.7463(3) 0.71124(19) 0.51636(17) 0.0667(8) Uani d . 1 . .
O O1 0.8667(2) 0.88843(15) 0.42578(14) 0.0596(6) Uani d . 1 . .
O O2 0.4232(2) 0.79961(16) 0.31937(17) 0.0697(7) Uani d . 1 . .
O O3 0.2329(2) 0.86236(17) 0.30416(18) 0.0849(9) Uani d D 1 . .
O O4 0.5658(2) 0.84529(16) 0.48997(14) 0.0683(7) Uani d . 1 . .
C C19' 0.0535(17) 0.7807(15) 0.2940(10) 0.123(8) Uani d PD 0.49 A 2
H H19D 0.0884 0.7667 0.3504 0.184 Uiso calc PR 0.49 A 2
H H19E -0.0025 0.7369 0.2658 0.184 Uiso calc PR 0.49 A 2
H H19F 0.0041 0.8311 0.2885 0.184 Uiso calc PR 0.49 A 2
C C18' 0.160(2) 0.7920(11) 0.2596(11) 0.099(7) Uani d PD 0.49 A 2
H H18C 0.1275 0.8040 0.2020 0.119 Uiso calc PR 0.49 A 2
H H18D 0.2153 0.7430 0.2675 0.119 Uiso calc PR 0.49 A 2
C C24' 0.8165(13) 0.5613(7) 0.3901(10) 0.064(4) Uani d PD 0.29 B 2
H H24C 0.7551 0.5582 0.3359 0.077 Uiso calc PR 0.29 B 2
H H24D 0.7973 0.5170 0.4226 0.077 Uiso calc PR 0.29 B 2
C C25' 0.9573(15) 0.5544(12) 0.3871(14) 0.114(8) Uani d PD 0.29 B 2
H H25D 0.9900 0.6086 0.3813 0.171 Uiso calc PR 0.29 B 2
H H25E 0.9590 0.5206 0.3418 0.171 Uiso calc PR 0.29 B 2
H H25F 1.0110 0.5296 0.4364 0.171 Uiso calc PR 0.29 B 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
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C1 . . 113.1(3) ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2B . . 109.0 ?
C1 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
N1 C3 C5 . . 110.1(3) ?
N1 C3 C2 . . 120.5(3) ?
C5 C3 C2 . . 129.4(4) ?
N2 C4 C5 . . 105.2(3) ?
N2 C4 C7 . . 120.0(3) ?
C5 C4 C7 . . 134.7(3) ?
C4 C5 C3 . . 106.8(3) ?
C4 C5 Cl1 . . 128.4(3) ?
C3 C5 Cl1 . . 124.7(3) ?
N2 C6 H6A . . 109.5 ?
N2 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
N2 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O1 C7 N3 . . 121.5(3) ?
O1 C7 C4 . . 123.4(3) ?
N3 C7 C4 . . 115.1(3) ?
C15 C8 N3 . . 121.8(3) ?
C15 C8 C9 . . 122.7(3) ?
N3 C8 C9 . . 115.3(2) ?
C14 C9 C10 . . 119.2(3) ?
C14 C9 C8 . . 121.5(3) ?
C10 C9 C8 . . 119.3(3) ?
C11 C10 C9 . . 120.3(3) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 118.8(3) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C13 C12 C11 . . 122.5(3) ?
C13 C12 Cl2 . . 118.8(3) ?
C11 C12 Cl2 . . 118.7(3) ?
C12 C13 C14 . . 118.6(4) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.6(3) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
C8 C15 C16 . . 119.0(3) ?
C8 C15 C17 . . 124.3(3) ?
C16 C15 C17 . . 116.7(3) ?
N4 C16 C15 . . 178.5(4) ?
O2 C17 O3 . . 123.8(3) ?
O2 C17 C15 . . 125.5(3) ?
O3 C17 C15 . . 110.7(3) ?
O4 C20 N3 . . 119.2(3) ?
O4 C20 C21 . . 123.3(3) ?
N3 C20 C21 . . 117.5(3) ?
N6 C21 C22 . . 105.6(3) ?
N6 C21 C20 . . 120.0(3) ?
C22 C21 C20 . . 134.3(3) ?
C21 C22 C23 . . 107.1(3) ?
C21 C22 Cl3 . . 127.6(3) ?
C10 C11 H11 . . 120.6 ?
C13 C12 C11 . . 122.5(3) ?
C13 C12 Cl2 . . 118.8(3) ?
C11 C12 Cl2 . . 118.7(3) ?
C12 C13 C14 . . 118.6(4) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.6(3) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
C8 C15 C16 . . 119.0(3) ?
C8 C15 C17 . . 124.3(3) ?
C16 C15 C17 . . 116.7(3) ?
N4 C16 C15 . . 178.5(4) ?
O2 C17 O3 . . 123.8(3) ?
O2 C17 C15 . . 125.5(3) ?
O3 C17 C15 . . 110.7(3) ?
O4 C20 N3 . . 119.2(3) ?
O4 C20 C21 . . 123.3(3) ?
N3 C20 C21 . . 117.5(3) ?
N6 C21 C22 . . 105.6(3) ?
N6 C21 C20 . . 120.0(3) ?
C22 C21 C20 . . 134.3(3) ?
C21 C22 C23 . . 107.1(3) ?
C21 C22 Cl3 . . 127.6(3) ?
C22 C21 C20 . . 134.3(3) ?
C21 C22 C23 . . 107.1(3) ?
C21 C22 Cl3 . . 127.6(3) ?
C23 C22 Cl3 . . 125.2(3) ?
N5 C23 C22 . . 109.3(3) ?
N5 C23 C24' . . 116.2(8) ?
C22 C23 C24' . . 128.4(8) ?
N5 C23 C24 . . 122.2(5) ?
C22 C23 C24 . . 127.2(5) ?
C19 C18 O3 . . 102.4(8) ?
C19 C18 H18A . . 111.3 ?
O3 C18 H18A . . 111.3 ?
C19 C18 H18B . . 111.3 ?
O3 C18 H18B . . 111.3 ?
H18A C18 H18B . . 109.2 ?
C25 C24 C23 . . 105.6(6) ?
C25 C24 H24A . . 110.6 ?
C23 C24 H24A . . 110.6 ?
C25 C24 H24B . . 110.6 ?
C23 C24 H24B . . 110.6 ?
H24A C24 H24B . . 108.7 ?
N6 C26 H26A . . 109.5 ?
N6 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
N6 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C3 N1 N2 . . 105.4(3) ?
N1 N2 C4 . . 112.4(3) ?
N1 N2 C6 . . 118.0(3) ?
C4 N2 C6 . . 129.4(3) ?
C8 N3 C7 . . 118.8(2) ?
C8 N3 C20 . . 117.9(2) ?
C7 N3 C20 . . 119.2(2) ?
N6 N5 C23 . . 106.1(3) ?
N5 N6 C21 . . 111.9(3) ?
N5 N6 C26 . . 118.7(3) ?
C21 N6 C26 . . 129.4(3) ?
C17 O3 C18' . . 117.5(10) ?
C17 O3 C18 . . 114.0(8) ?
C18' C19' H19D . . 109.5 ?
C18' C19' H19E . . 109.5 ?
H19D C19' H19E . . 109.5 ?
C18' C19' H19F . . 109.5 ?
H19D C19' H19F . . 109.5 ?
H19E C19' H19F . . 109.5 ?
C19' C18' O3 . . 103.9(9) ?
C19' C18' H18C . . 111.0 ?
O3 C18' H18C . . 111.0 ?
C19' C18' H18D . . 111.0 ?
O3 C18' H18D . . 111.0 ?
H18C C18' H18D . . 109.0 ?
C23 C24' C25' . . 106.0(8) ?
C23 C24' H24C . . 110.5 ?
C25' C24' H24C . . 110.5 ?
C23 C24' H24D . . 110.5 ?
C25' C24' H24D . . 110.5 ?
H24C C24' H24D . . 108.7 ?
C24' C25' H25D . . 109.5 ?
C24' C25' H25E . . 109.5 ?
H25D C25' H25E . . 109.5 ?
C24' C25' H25F . . 109.5 ?
H25D C25' H25F . . 109.5 ?
H25E C25' H25F . . 109.5 ?
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
C1 C2 . 1.505(6) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.499(5) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N1 . 1.343(5) ?
C3 C5 . 1.387(5) ?
C4 N2 . 1.358(4) ?
C4 C5 . 1.383(4) ?
C4 C7 . 1.476(4) ?
C5 Cl1 . 1.716(3) ?
C6 N2 . 1.465(5) ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 O1 . 1.202(3) ?
C7 N3 . 1.423(4) ?
C8 C15 . 1.356(4) ?
C8 N3 . 1.415(4) ?
C8 C9 . 1.475(4) ?
C9 C14 . 1.387(4) ?
C9 C10 . 1.395(4) ?
C10 C11 . 1.376(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.370(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.367(5) ?
C12 Cl2 . 1.752(4) ?
C13 C14 . 1.379(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.436(5) ?
C15 C17 . 1.491(5) ?
C16 N4 . 1.139(4) ?
C17 O2 . 1.196(4) ?
C17 O3 . 1.323(4) ?
C20 O4 . 1.197(4) ?
C20 N3 . 1.444(4) ?
C20 C21 . 1.460(5) ?
C21 N6 . 1.353(4) ?
C21 C22 . 1.381(5) ?
C22 C23 . 1.382(6) ?
C22 Cl3 . 1.710(4) ?
C23 N5 . 1.348(5) ?
C23 C24' . 1.484(9) ?
C23 C24 . 1.542(7) ?
C18 C19 . 1.465(10) ?
C18 O3 . 1.475(8) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C24 C25 . 1.481(7) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
C26 N6 . 1.457(5) ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
N1 N2 . 1.349(4) ?
N5 N6 . 1.345(4) ?
O3 C18' . 1.458(9) ?
C19' C18' . 1.456(10) ?
C19' H19D . 0.9600 ?
C19' H19E . 0.9600 ?
C19' H19F . 0.9600 ?
C18' H18C . 0.9700 ?
C18' H18D . 0.9700 ?
C24' C25' . 1.531(10) ?
C24' H24C . 0.9700 ?
C24' H24D . 0.9700 ?
C25' H25D . 0.9600 ?
C25' H25E . 0.9600 ?
C25' H25F . 0.9600 ?
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
C13 H13 O2 2_655 0.93 2.59 3.420(5) 148.7
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
C1 C2 C3 N1 . . . . -107.3(5) ?
C1 C2 C3 C5 . . . . 72.6(6) ?
N2 C4 C5 C3 . . . . 0.2(4) ?
C7 C4 C5 C3 . . . . -176.8(3) ?
N2 C4 C5 Cl1 . . . . 178.8(2) ?
C7 C4 C5 Cl1 . . . . 1.8(6) ?
N1 C3 C5 C4 . . . . -1.2(4) ?
C2 C3 C5 C4 . . . . 178.9(4) ?
N1 C3 C5 Cl1 . . . . -179.8(3) ?
C2 C3 C5 Cl1 . . . . 0.2(6) ?
N2 C4 C7 O1 . . . . -33.8(5) ?
C5 C4 C7 O1 . . . . 142.9(4) ?
N2 C4 C7 N3 . . . . 145.1(3) ?
C5 C4 C7 N3 . . . . -38.2(5) ?
C15 C8 C9 C14 . . . . -51.9(4) ?
N3 C8 C9 C14 . . . . 133.3(3) ?
C15 C8 C9 C10 . . . . 130.3(3) ?
N3 C8 C9 C10 . . . . -44.5(4) ?
C14 C9 C10 C11 . . . . 0.7(5) ?
C8 C9 C10 C11 . . . . 178.5(3) ?
C9 C10 C11 C12 . . . . -1.4(5) ?
C10 C11 C12 C13 . . . . 1.7(6) ?
C10 C11 C12 Cl2 . . . . -178.5(3) ?
C11 C12 C13 C14 . . . . -1.3(6) ?
Cl2 C12 C13 C14 . . . . 178.9(3) ?
C12 C13 C14 C9 . . . . 0.5(5) ?
C10 C9 C14 C13 . . . . -0.2(5) ?
C8 C9 C14 C13 . . . . -178.0(3) ?
N3 C8 C15 C16 . . . . 170.3(3) ?
C9 C8 C15 C16 . . . . -4.3(4) ?
N3 C8 C15 C17 . . . . -9.9(5) ?
C9 C8 C15 C17 . . . . 175.6(3) ?
C8 C15 C17 O2 . . . . -3.5(5) ?
C16 C15 C17 O2 . . . . 176.4(3) ?
C8 C15 C17 O3 . . . . 177.0(3) ?
C16 C15 C17 O3 . . . . -3.1(4) ?
O4 C20 C21 N6 . . . . -27.8(5) ?
N3 C20 C21 N6 . . . . 152.4(3) ?
O4 C20 C21 C22 . . . . 149.1(4) ?
N3 C20 C21 C22 . . . . -30.7(5) ?
N6 C21 C22 C23 . . . . -0.2(4) ?
C20 C21 C22 C23 . . . . -177.4(4) ?
N6 C21 C22 Cl3 . . . . 176.9(3) ?
C20 C21 C22 Cl3 . . . . -0.3(6) ?
C21 C22 C23 N5 . . . . 0.1(6) ?
Cl3 C22 C23 N5 . . . . -177.1(3) ?
C21 C22 C23 C24' . . . . 151.0(8) ?
Cl3 C22 C23 C24' . . . . -26.2(10) ?
C21 C22 C23 C24 . . . . -166.6(5) ?
Cl3 C22 C23 C24 . . . . 16.2(8) ?
N5 C23 C24 C25 . . . . 76.6(8) ?
C22 C23 C24 C25 . . . . -118.3(7) ?
C24' C23 C24 C25 . . . . -12.9(14) ?
C5 C3 N1 N2 . . . . 1.6(4) ?
C2 C3 N1 N2 . . . . -178.4(3) ?
C3 N1 N2 C4 . . . . -1.6(4) ?
C3 N1 N2 C6 . . . . -176.7(3) ?
C5 C4 N2 N1 . . . . 0.8(4) ?
C7 C4 N2 N1 . . . . 178.4(3) ?
C5 C4 N2 C6 . . . . 175.3(4) ?
C7 C4 N2 C6 . . . . -7.1(5) ?
C15 C8 N3 C7 . . . . 149.4(3) ?
C9 C8 N3 C7 . . . . -35.7(4) ?
C15 C8 N3 C20 . . . . -53.3(4) ?
C9 C8 N3 C20 . . . . 121.6(3) ?
O1 C7 N3 C8 . . . . 140.0(3) ?
C4 C7 N3 C8 . . . . -38.9(4) ?
O1 C7 N3 C20 . . . . -17.0(4) ?
C4 C7 N3 C20 . . . . 164.1(3) ?
O4 C20 N3 C8 . . . . -16.6(4) ?
C21 C20 N3 C8 . . . . 163.2(3) ?
O4 C20 N3 C7 . . . . 140.6(3) ?
C21 C20 N3 C7 . . . . -39.6(4) ?
C22 C23 N5 N6 . . . . 0.0(6) ?
C24' C23 N5 N6 . . . . -154.8(7) ?
C24 C23 N5 N6 . . . . 167.5(5) ?
C23 N5 N6 C21 . . . . -0.2(5) ?
C23 N5 N6 C26 . . . . -179.5(4) ?
C22 C21 N6 N5 . . . . 0.2(4) ?
C20 C21 N6 N5 . . . . 178.0(3) ?
C22 C21 N6 C26 . . . . 179.5(4) ?
C20 C21 N6 C26 . . . . -2.8(6) ?
O2 C17 O3 C18' . . . . -14.9(10) ?
C15 C17 O3 C18' . . . . 164.7(9) ?
O2 C17 O3 C18 . . . . 9.9(9) ?
C15 C17 O3 C18 . . . . -170.5(8) ?
C19 C18 O3 C17 . . . . -164.7(12) ?
C19 C18 O3 C18' . . . . -60(4) ?
C17 O3 C18' C19' . . . . 142.5(12) ?
C18 O3 C18' C19' . . . . 56(4) ?
N5 C23 C24' C25' . . . . -103.8(14) ?
C22 C23 C24' C25' . . . . 107.0(14) ?
C24 C23 C24' C25' . . . . 5.7(12) ?
