#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/67/2226796.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_2226796
loop_
_publ_author_name
'Al-Tamimi, Abdul-Malek S.'
'Bari, Ahmed'
'Al-Omar, Mohamed A.'
'El-Emam, Ali A.'
'Ng, Seik Weng'
_publ_section_title
;
 N'-[(2-n-Butyl-4-chloro-1H-imidazol-5-yl)methylidene]adamantane-1-carbohydrazide
 sesquihydrate ethanol hemisolvate
;
_journal_coeditor_code           BT5304
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2131
_journal_paper_doi               10.1107/S1600536810029260
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H27 Cl N4 O, 0.5C2 H6 O, 1.5H2 O'
_chemical_formula_moiety         'C19 H27 Cl N4 O, 0.5C2 H6 O, 1.5H2 O'
_chemical_formula_sum            'C20 H33 Cl N4 O3'
_chemical_formula_weight         412.95
_chemical_name_systematic
;
N'-[(2-n-Butyl-4-chloro-1H-imidazol-5-
yl)methylidene]adamantane-1-carbohydrazide sesquihydrate ethanol 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                97.3410(10)
_cell_angle_beta                 100.3760(10)
_cell_angle_gamma                97.5050(10)
_cell_formula_units_Z            4
_cell_length_a                   7.9867(6)
_cell_length_b                   16.8478(13)
_cell_length_c                   16.9656(13)
_cell_measurement_reflns_used    4692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.5
_cell_volume                     2199.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21291
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     552
_refine_ls_number_reflns         10050
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0427
_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)+(0.0579P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                7547
_reflns_number_total             10050
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5304.cif
_cod_data_source_block           I
_cod_database_code               2226796
_cod_database_fobs_code          2226796
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 0.76837(6) 1.16482(3) 0.27186(3) 0.02855(12) Uani d . 1 . .
Cl Cl2 0.96970(5) 0.80656(2) 0.35728(3) 0.02268(10) Uani d . 1 . .
O O1 0.75877(14) 1.40939(7) 0.65640(7) 0.0201(3) Uani d . 1 . .
O O2 0.73265(14) 1.07788(7) 0.06758(7) 0.0188(2) Uani d . 1 . .
O O3 0.78300(16) 0.63333(8) 0.50491(8) 0.0284(3) Uani d D 1 . .
O O1W 0.54116(15) 0.70102(7) 0.41892(7) 0.0196(3) Uani d D 1 . .
O O2W 0.46191(15) 0.95403(7) 0.08834(7) 0.0201(3) Uani d D 1 . .
O O3W 0.27823(15) 1.00424(7) 0.20395(7) 0.0216(3) Uani d D 1 . .
N N1 0.92004(18) 1.38006(8) 0.56315(8) 0.0180(3) Uani d D 1 . .
N N2 0.78186(17) 1.32710(8) 0.51751(8) 0.0178(3) Uani d . 1 . .
N N3 0.50609(18) 1.21097(8) 0.43693(8) 0.0173(3) Uani d D 1 . .
N N4 0.46659(18) 1.13115(8) 0.31913(8) 0.0204(3) Uani d . 1 . .
N N5 0.62851(18) 0.77835(8) 0.29533(8) 0.0195(3) Uani d . 1 . .
N N6 0.60000(18) 0.86304(8) 0.20631(8) 0.0176(3) Uani d D 1 . .
N N7 0.83450(17) 0.98033(8) 0.16998(8) 0.0158(3) Uani d . 1 . .
N N8 0.95038(17) 1.04002(8) 0.15190(8) 0.0151(3) Uani d D 1 . .
C C1 1.0617(2) 1.46542(9) 0.69156(9) 0.0157(3) Uani d . 1 . .
C C2 1.1519(2) 1.52998(9) 0.64919(10) 0.0182(3) Uani d . 1 . .
H H2A 1.1853 1.5032 0.6002 0.022 Uiso calc R 1 . .
H H2B 1.0716 1.5675 0.6321 0.022 Uiso calc R 1 . .
C C3 1.3131(2) 1.57772(10) 0.70820(10) 0.0214(4) Uani d . 1 . .
H H3A 1.3706 1.6198 0.6811 0.026 Uiso calc R 1 . .
C C4 1.4376(2) 1.51865(11) 0.73189(11) 0.0238(4) Uani d . 1 . .
H H4A 1.4708 1.4921 0.6828 0.029 Uiso calc R 1 . .
H H4B 1.5435 1.5487 0.7688 0.029 Uiso calc R 1 . .
C C5 1.3512(2) 1.45452(10) 0.77393(10) 0.0218(4) Uani d . 1 . .
H H5 1.4330 1.4164 0.7895 0.026 Uiso calc R 1 . .
C C6 1.3012(2) 1.49608(11) 0.85039(10) 0.0250(4) Uani d . 1 . .
H H6A 1.2465 1.4548 0.8783 0.030 Uiso calc R 1 . .
H H6B 1.4057 1.5264 0.8881 0.030 Uiso calc R 1 . .
C C7 1.1755(2) 1.55423(10) 0.82642(10) 0.0218(4) Uani d . 1 . .
H H7 1.1428 1.5813 0.8762 0.026 Uiso calc R 1 . .
C C8 1.2614(2) 1.61865(10) 0.78384(11) 0.0249(4) Uani d . 1 . .
H H8A 1.1803 1.6563 0.7684 0.030 Uiso calc R 1 . .
H H8B 1.3648 1.6504 0.8213 0.030 Uiso calc R 1 . .
C C9 1.1886(2) 1.40708(10) 0.71633(10) 0.0184(3) Uani d . 1 . .
H H9A 1.1329 1.3654 0.7435 0.022 Uiso calc R 1 . .
H H9B 1.2203 1.3793 0.6674 0.022 Uiso calc R 1 . .
C C10 1.0134(2) 1.50723(10) 0.76836(10) 0.0183(3) Uani d . 1 . .
H H10A 0.9319 1.5449 0.7534 0.022 Uiso calc R 1 . .
H H10B 0.9559 1.4661 0.7956 0.022 Uiso calc R 1 . .
C C11 0.8996(2) 1.41698(9) 0.63612(9) 0.0153(3) Uani d . 1 . .
C C12 0.8028(2) 1.28451(9) 0.45310(9) 0.0173(3) Uani d . 1 . .
H H12A 0.9093 1.2909 0.4354 0.021 Uiso calc R 1 . .
C C13 0.6573(2) 1.22641(9) 0.40851(10) 0.0165(3) Uani d . 1 . .
C C14 0.6272(2) 1.17570(10) 0.33610(10) 0.0185(3) Uani d . 1 . .
C C15 0.3969(2) 1.15408(10) 0.38198(10) 0.0198(4) Uani d . 1 . .
C C16 0.2199(2) 1.11990(11) 0.39062(11) 0.0251(4) Uani d . 1 . .
H H16A 0.1425 1.1094 0.3366 0.030 Uiso calc R 1 . .
H H16B 0.1759 1.1605 0.4256 0.030 Uiso calc R 1 . .
C C17 0.2146(2) 1.04091(11) 0.42715(12) 0.0308(4) Uani d . 1 . .
H H17A 0.0940 1.0127 0.4158 0.037 Uiso calc R 1 . .
H H17B 0.2833 1.0051 0.4003 0.037 Uiso calc R 1 . .
C C18 0.2832(3) 1.05454(13) 0.51753(13) 0.0377(5) Uani d . 1 . .
H H18A 0.2149 1.0907 0.5443 0.045 Uiso calc R 1 . .
H H18B 0.4039 1.0825 0.5287 0.045 Uiso calc R 1 . .
C C19 0.2776(3) 0.97727(16) 0.55442(17) 0.0588(8) Uani d . 1 . .
H H19A 0.3189 0.9906 0.6133 0.088 Uiso calc R 1 . .
H H19B 0.3515 0.9426 0.5311 0.088 Uiso calc R 1 . .
H H19C 0.1589 0.9486 0.5428 0.088 Uiso calc R 1 . .
C C20 1.0200(2) 1.15241(9) 0.07997(9) 0.0143(3) Uani d . 1 . .
C C21 1.1515(2) 1.19510(10) 0.15687(9) 0.0173(3) Uani d . 1 . .
H H21A 1.0903 1.2215 0.1962 0.021 Uiso calc R 1 . .
H H21B 1.2121 1.1546 0.1827 0.021 Uiso calc R 1 . .
C C22 1.2828(2) 1.25884(10) 0.13452(10) 0.0191(4) Uani d . 1 . .
H H22A 1.3672 1.2860 0.1846 0.023 Uiso calc R 1 . .
C C23 1.1891(2) 1.32202(10) 0.09564(11) 0.0239(4) Uani d . 1 . .
H H23A 1.1275 1.3491 0.1344 0.029 Uiso calc R 1 . .
H H23B 1.2736 1.3637 0.0818 0.029 Uiso calc R 1 . .
C C24 1.0604(2) 1.28048(10) 0.01893(11) 0.0233(4) Uani d . 1 . .
H H24 0.9992 1.3218 -0.0064 0.028 Uiso calc R 1 . .
C C25 0.9281(2) 1.21643(10) 0.04083(11) 0.0201(4) Uani d . 1 . .
H H25A 0.8645 1.2429 0.0790 0.024 Uiso calc R 1 . .
H H25B 0.8439 1.1900 -0.0088 0.024 Uiso calc R 1 . .
C C26 1.1560(2) 1.23945(11) -0.04119(11) 0.0259(4) Uani d . 1 . .
H H26A 1.0730 1.2130 -0.0911 0.031 Uiso calc R 1 . .
H H26B 1.2402 1.2805 -0.0562 0.031 Uiso calc R 1 . .
C C27 1.2497(2) 1.17624(10) -0.00257(10) 0.0206(4) Uani d . 1 . .
H H27 1.3125 1.1496 -0.0419 0.025 Uiso calc R 1 . .
C C28 1.3788(2) 1.21725(10) 0.07450(10) 0.0216(4) Uani d . 1 . .
H H28A 1.4657 1.2579 0.0607 0.026 Uiso calc R 1 . .
H H28B 1.4395 1.1763 0.0996 0.026 Uiso calc R 1 . .
C C29 1.1182(2) 1.11208(9) 0.01915(10) 0.0181(3) Uani d . 1 . .
H H29A 1.1784 1.0706 0.0435 0.022 Uiso calc R 1 . .
H H29B 1.0355 1.0849 -0.0306 0.022 Uiso calc R 1 . .
C C30 0.8874(2) 1.08749(9) 0.09866(9) 0.0147(3) Uani d . 1 . .
C C31 0.8957(2) 0.93466(9) 0.21920(9) 0.0170(3) Uani d . 1 . .
H H31A 1.0157 0.9405 0.2410 0.020 Uiso calc R 1 . .
C C32 0.7734(2) 0.87396(9) 0.23988(9) 0.0168(3) Uani d . 1 . .
C C33 0.7857(2) 0.82064(10) 0.29406(10) 0.0182(3) Uani d . 1 . .
C C34 0.5179(2) 0.80624(10) 0.24081(10) 0.0188(3) Uani d . 1 . .
C C35 0.3269(2) 0.77994(10) 0.21929(11) 0.0235(4) Uani d . 1 . .
H H35A 0.2761 0.8135 0.1804 0.028 Uiso calc R 1 . .
H H35B 0.2786 0.7898 0.2688 0.028 Uiso calc R 1 . .
C C36 0.2740(2) 0.69046(10) 0.18198(10) 0.0223(4) Uani d . 1 . .
H H36A 0.3137 0.6569 0.2233 0.027 Uiso calc R 1 . .
H H36B 0.1466 0.6782 0.1680 0.027 Uiso calc R 1 . .
C C37 0.3442(2) 0.66585(11) 0.10660(11) 0.0273(4) Uani d . 1 . .
H H37A 0.4717 0.6740 0.1209 0.033 Uiso calc R 1 . .
H H37B 0.3106 0.7011 0.0660 0.033 Uiso calc R 1 . .
C C38 0.2775(3) 0.57763(13) 0.06950(12) 0.0390(5) Uani d . 1 . .
H H38A 0.3292 0.5636 0.0224 0.058 Uiso calc R 1 . .
H H38B 0.1518 0.5700 0.0523 0.058 Uiso calc R 1 . .
H H38C 0.3085 0.5426 0.1099 0.058 Uiso calc R 1 . .
C C39 0.7041(2) 0.59637(11) 0.56315(11) 0.0292(4) Uani d . 1 . .
H H39A 0.7416 0.5431 0.5676 0.035 Uiso calc R 1 . .
H H39B 0.5773 0.5871 0.5446 0.035 Uiso calc R 1 . .
C C40 0.7512(3) 0.64869(12) 0.64503(11) 0.0317(4) Uani d . 1 . .
H H40A 0.7063 0.6193 0.6850 0.048 Uiso calc R 1 . .
H H40B 0.7011 0.6986 0.6423 0.048 Uiso calc R 1 . .
H H40C 0.8769 0.6623 0.6611 0.048 Uiso calc R 1 . .
H H3o 0.709(2) 0.6547(12) 0.4769(11) 0.040(6) Uiso d D 1 . .
H H11 0.4462(17) 0.6699(11) 0.4039(12) 0.039(6) Uiso d D 1 . .
H H12 0.561(3) 0.7241(15) 0.3798(11) 0.068(9) Uiso d D 1 . .
H H21 0.547(2) 0.9885(11) 0.0863(14) 0.047(7) Uiso d D 1 . .
H H22 0.402(2) 0.9418(11) 0.0416(7) 0.028(5) Uiso d D 1 . .
H H31 0.348(2) 1.0401(11) 0.2379(11) 0.050(7) Uiso d D 1 . .
H H32 0.328(3) 0.9889(13) 0.1658(10) 0.047(7) Uiso d D 1 . .
H H1 1.0165(16) 1.3843(11) 0.5468(11) 0.022(5) Uiso d D 1 . .
H H3 0.491(2) 1.2324(11) 0.4835(7) 0.030(5) Uiso d D 1 . .
H H6 0.553(2) 0.8878(11) 0.1671(9) 0.032(6) Uiso d D 1 . .
H H8 1.0584(13) 1.0385(11) 0.1682(11) 0.029(5) 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
C39 O3 H3o . . 108.2(15) ?
H11 O1W H12 . . 108(2) ?
H21 O2W H22 . . 107(2) ?
H31 O3W H32 . . 109(2) ?
C11 N1 N2 . . 116.73(13) ?
C11 N1 H1 . . 124.0(13) ?
N2 N1 H1 . . 119.0(12) ?
C12 N2 N1 . . 118.29(14) ?
C15 N3 C13 . . 107.94(14) ?
C15 N3 H3 . . 127.7(13) ?
C13 N3 H3 . . 124.2(13) ?
C15 N4 C14 . . 104.80(13) ?
C34 N5 C33 . . 104.56(13) ?
C34 N6 C32 . . 108.41(14) ?
C34 N6 H6 . . 126.6(13) ?
C32 N6 H6 . . 125.0(13) ?
C31 N7 N8 . . 116.86(14) ?
C30 N8 N7 . . 117.28(13) ?
C30 N8 H8 . . 124.6(13) ?
N7 N8 H8 . . 117.2(13) ?
C11 C1 C10 . . 109.09(13) ?
C11 C1 C9 . . 109.09(12) ?
C10 C1 C9 . . 108.73(13) ?
C11 C1 C2 . . 111.73(13) ?
C10 C1 C2 . . 109.51(13) ?
C9 C1 C2 . . 108.64(13) ?
C3 C2 C1 . . 109.50(13) ?
C3 C2 H2A . . 109.8 ?
C1 C2 H2A . . 109.8 ?
C3 C2 H2B . . 109.8 ?
C1 C2 H2B . . 109.8 ?
H2A C2 H2B . . 108.2 ?
C8 C3 C4 . . 109.85(14) ?
C8 C3 C2 . . 109.70(14) ?
C4 C3 C2 . . 108.74(13) ?
C8 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
C5 C4 C3 . . 109.80(14) ?
C5 C4 H4A . . 109.7 ?
C3 C4 H4A . . 109.7 ?
C5 C4 H4B . . 109.7 ?
C3 C4 H4B . . 109.7 ?
H4A C4 H4B . . 108.2 ?
C4 C5 C9 . . 109.74(13) ?
C4 C5 C6 . . 109.39(14) ?
C9 C5 C6 . . 109.32(14) ?
C4 C5 H5 . . 109.5 ?
C9 C5 H5 . . 109.5 ?
C6 C5 H5 . . 109.5 ?
C7 C6 C5 . . 109.40(14) ?
C7 C6 H6A . . 109.8 ?
C5 C6 H6A . . 109.8 ?
C7 C6 H6B . . 109.8 ?
C5 C6 H6B . . 109.8 ?
H6A C6 H6B . . 108.2 ?
C6 C7 C10 . . 109.82(14) ?
C6 C7 C8 . . 109.62(14) ?
C10 C7 C8 . . 108.98(14) ?
C6 C7 H7 . . 109.5 ?
C10 C7 H7 . . 109.5 ?
C8 C7 H7 . . 109.5 ?
C3 C8 C7 . . 109.75(13) ?
C3 C8 H8A . . 109.7 ?
C7 C8 H8A . . 109.7 ?
C3 C8 H8B . . 109.7 ?
C7 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
C5 C9 C1 . . 109.88(13) ?
C5 C9 H9A . . 109.7 ?
C1 C9 H9A . . 109.7 ?
C5 C9 H9B . . 109.7 ?
C1 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
C7 C10 C1 . . 110.06(13) ?
C7 C10 H10A . . 109.6 ?
C1 C10 H10A . . 109.6 ?
C7 C10 H10B . . 109.6 ?
C1 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.2 ?
O1 C11 N1 . . 121.44(15) ?
O1 C11 C1 . . 122.50(14) ?
N1 C11 C1 . . 116.03(14) ?
N2 C12 C13 . . 116.98(15) ?
N2 C12 H12A . . 121.5 ?
C13 C12 H12A . . 121.5 ?
C14 C13 N3 . . 103.96(14) ?
C14 C13 C12 . . 133.60(15) ?
N3 C13 C12 . . 122.43(14) ?
N4 C14 C13 . . 111.82(14) ?
N4 C14 Cl1 . . 121.52(12) ?
C13 C14 Cl1 . . 126.65(13) ?
N4 C15 N3 . . 111.47(14) ?
N4 C15 C16 . . 123.95(15) ?
N3 C15 C16 . . 124.58(15) ?
C15 C16 C17 . . 113.03(15) ?
C15 C16 H16A . . 109.0 ?
C17 C16 H16A . . 109.0 ?
C15 C16 H16B . . 109.0 ?
C17 C16 H16B . . 109.0 ?
H16A C16 H16B . . 107.8 ?
C18 C17 C16 . . 113.12(16) ?
C18 C17 H17A . . 109.0 ?
C16 C17 H17A . . 109.0 ?
C18 C17 H17B . . 109.0 ?
C16 C17 H17B . . 109.0 ?
H17A C17 H17B . . 107.8 ?
C17 C18 C19 . . 113.7(2) ?
C17 C18 H18A . . 108.8 ?
C19 C18 H18A . . 108.8 ?
C17 C18 H18B . . 108.8 ?
C19 C18 H18B . . 108.8 ?
H18A C18 H18B . . 107.7 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C30 C20 C25 . . 109.75(13) ?
C30 C20 C21 . . 112.26(12) ?
C25 C20 C21 . . 108.69(13) ?
C30 C20 C29 . . 108.65(12) ?
C25 C20 C29 . . 108.58(13) ?
C21 C20 C29 . . 108.83(13) ?
C22 C21 C20 . . 110.09(13) ?
C22 C21 H21A . . 109.6 ?
C20 C21 H21A . . 109.6 ?
C22 C21 H21B . . 109.6 ?
C20 C21 H21B . . 109.6 ?
H21A C21 H21B . . 108.2 ?
C23 C22 C28 . . 109.68(14) ?
C23 C22 C21 . . 109.51(14) ?
C28 C22 C21 . . 109.28(13) ?
C23 C22 H22A . . 109.5 ?
C28 C22 H22A . . 109.5 ?
C21 C22 H22A . . 109.5 ?
C24 C23 C22 . . 109.42(13) ?
C24 C23 H23A . . 109.8 ?
C22 C23 H23A . . 109.8 ?
C24 C23 H23B . . 109.8 ?
C22 C23 H23B . . 109.8 ?
H23A C23 H23B . . 108.2 ?
C23 C24 C26 . . 109.71(14) ?
C23 C24 C25 . . 109.66(14) ?
C26 C24 C25 . . 109.38(14) ?
C23 C24 H24 . . 109.4 ?
C26 C24 H24 . . 109.4 ?
C25 C24 H24 . . 109.4 ?
C20 C25 C24 . . 110.06(13) ?
C20 C25 H25A . . 109.6 ?
C24 C25 H25A . . 109.6 ?
C20 C25 H25B . . 109.6 ?
C24 C25 H25B . . 109.6 ?
H25A C25 H25B . . 108.2 ?
C27 C26 C24 . . 109.48(14) ?
C27 C26 H26A . . 109.8 ?
C24 C26 H26A . . 109.8 ?
C27 C26 H26B . . 109.8 ?
C24 C26 H26B . . 109.8 ?
H26A C26 H26B . . 108.2 ?
C26 C27 C28 . . 109.75(14) ?
C26 C27 C29 . . 109.49(14) ?
C28 C27 C29 . . 109.40(13) ?
C26 C27 H27 . . 109.4 ?
C28 C27 H27 . . 109.4 ?
C29 C27 H27 . . 109.4 ?
C27 C28 C22 . . 109.47(13) ?
C27 C28 H28A . . 109.8 ?
C22 C28 H28A . . 109.8 ?
C27 C28 H28B . . 109.8 ?
C22 C28 H28B . . 109.8 ?
H28A C28 H28B . . 108.2 ?
C27 C29 C20 . . 109.95(12) ?
C27 C29 H29A . . 109.7 ?
C20 C29 H29A . . 109.7 ?
C27 C29 H29B . . 109.7 ?
C20 C29 H29B . . 109.7 ?
H29A C29 H29B . . 108.2 ?
O2 C30 N8 . . 121.49(14) ?
O2 C30 C20 . . 122.90(14) ?
N8 C30 C20 . . 115.61(13) ?
N7 C31 C32 . . 116.67(15) ?
N7 C31 H31A . . 121.7 ?
C32 C31 H31A . . 121.7 ?
C33 C32 N6 . . 104.13(14) ?
C33 C32 C31 . . 133.72(16) ?
N6 C32 C31 . . 122.04(15) ?
C32 C33 N5 . . 111.78(15) ?
C32 C33 Cl2 . . 126.87(13) ?
N5 C33 Cl2 . . 121.32(12) ?
N5 C34 N6 . . 111.12(15) ?
N5 C34 C35 . . 126.11(15) ?
N6 C34 C35 . . 122.77(15) ?
C34 C35 C36 . . 113.43(14) ?
C34 C35 H35A . . 108.9 ?
C36 C35 H35A . . 108.9 ?
C34 C35 H35B . . 108.9 ?
C36 C35 H35B . . 108.9 ?
H35A C35 H35B . . 107.7 ?
C37 C36 C35 . . 114.70(14) ?
C37 C36 H36A . . 108.6 ?
C35 C36 H36A . . 108.6 ?
C37 C36 H36B . . 108.6 ?
C35 C36 H36B . . 108.6 ?
H36A C36 H36B . . 107.6 ?
C36 C37 C38 . . 111.99(16) ?
C36 C37 H37A . . 109.2 ?
C38 C37 H37A . . 109.2 ?
C36 C37 H37B . . 109.2 ?
C38 C37 H37B . . 109.2 ?
H37A C37 H37B . . 107.9 ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
O3 C39 C40 . . 111.29(15) ?
O3 C39 H39A . . 109.4 ?
C40 C39 H39A . . 109.4 ?
O3 C39 H39B . . 109.4 ?
C40 C39 H39B . . 109.4 ?
H39A C39 H39B . . 108.0 ?
C39 C40 H40A . . 109.5 ?
C39 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
C39 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 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
Cl1 C14 . 1.7142(17) ?
Cl2 C33 . 1.7186(17) ?
O1 C11 . 1.2300(19) ?
O2 C30 . 1.2344(19) ?
O3 C39 . 1.428(2) ?
O3 H3o . 0.840(10) ?
O1W H11 . 0.840(10) ?
O1W H12 . 0.840(10) ?
O2W H21 . 0.850(10) ?
O2W H22 . 0.840(10) ?
O3W H31 . 0.840(10) ?
O3W H32 . 0.850(10) ?
N1 C11 . 1.360(2) ?
N1 N2 . 1.3682(18) ?
N1 H1 . 0.860(10) ?
N2 C12 . 1.278(2) ?
N3 C15 . 1.345(2) ?
N3 C13 . 1.385(2) ?
N3 H3 . 0.860(10) ?
N4 C15 . 1.327(2) ?
N4 C14 . 1.361(2) ?
N5 C34 . 1.335(2) ?
N5 C33 . 1.366(2) ?
N6 C34 . 1.344(2) ?
N6 C32 . 1.378(2) ?
N6 H6 . 0.880(10) ?
N7 C31 . 1.282(2) ?
N7 N8 . 1.3784(18) ?
N8 C30 . 1.354(2) ?
N8 H8 . 0.860(10) ?
C1 C11 . 1.522(2) ?
C1 C10 . 1.536(2) ?
C1 C9 . 1.544(2) ?
C1 C2 . 1.549(2) ?
C2 C3 . 1.538(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C8 . 1.527(2) ?
C3 C4 . 1.536(2) ?
C3 H3A . 1.0000 ?
C4 C5 . 1.527(2) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C9 . 1.534(2) ?
C5 C6 . 1.536(2) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.531(2) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C10 . 1.532(2) ?
C7 C8 . 1.535(2) ?
C7 H7 . 1.0000 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C12 C13 . 1.441(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.367(2) ?
C15 C16 . 1.494(2) ?
C16 C17 . 1.537(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.510(3) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 C19 . 1.514(3) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 C30 . 1.525(2) ?
C20 C25 . 1.535(2) ?
C20 C21 . 1.547(2) ?
C20 C29 . 1.547(2) ?
C21 C22 . 1.533(2) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 C23 . 1.529(2) ?
C22 C28 . 1.535(2) ?
C22 H22A . 1.0000 ?
C23 C24 . 1.529(2) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C26 . 1.529(3) ?
C24 C25 . 1.538(2) ?
C24 H24 . 1.0000 ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 C27 . 1.527(2) ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
C27 C28 . 1.532(2) ?
C27 C29 . 1.533(2) ?
C27 H27 . 1.0000 ?
C28 H28A . 0.9900 ?
C28 H28B . 0.9900 ?
C29 H29A . 0.9900 ?
C29 H29B . 0.9900 ?
C31 C32 . 1.441(2) ?
C31 H31A . 0.9500 ?
C32 C33 . 1.365(2) ?
C34 C35 . 1.496(2) ?
C35 C36 . 1.531(2) ?
C35 H35A . 0.9900 ?
C35 H35B . 0.9900 ?
C36 C37 . 1.519(2) ?
C36 H36A . 0.9900 ?
C36 H36B . 0.9900 ?
C37 C38 . 1.524(3) ?
C37 H37A . 0.9900 ?
C37 H37B . 0.9900 ?
C38 H38A . 0.9800 ?
C38 H38B . 0.9800 ?
C38 H38C . 0.9800 ?
C39 C40 . 1.503(3) ?
C39 H39A . 0.9900 ?
C39 H39B . 0.9900 ?
C40 H40A . 0.9800 ?
C40 H40B . 0.9800 ?
C40 H40C . 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
N1 H1 O3 2_776 0.860(10) 2.000(10) 2.841(2) 166(2) yes
N3 H3 O1w 2_676 0.860(10) 1.950(10) 2.806(2) 170(2) yes
N6 H6 O2w . 0.880(10) 1.950(10) 2.829(2) 174(2) yes
N8 H8 O3w 1_655 0.860(10) 1.940(10) 2.778(2) 164(2) yes
O3 H3o O1w . 0.840(10) 1.840(10) 2.673(2) 177(2) yes
O1w H11 O1 2_676 0.840(10) 2.000(10) 2.821(2) 166(2) yes
O1w H12 N5 . 0.840(10) 1.910(10) 2.751(2) 175(3) yes
O2w H21 O2 . 0.850(10) 2.070(10) 2.905(2) 172(2) yes
O2w H22 O2 2_675 0.840(10) 1.930(10) 2.764(2) 176(2) yes
O3w H31 N4 . 0.840(10) 1.940(10) 2.773(2) 169(2) yes
O3w H32 O2w . 0.850(10) 1.920(10) 2.766(2) 174(2) 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
C11 N1 N2 C12 . . . . -172.14(15) ?
C31 N7 N8 C30 . . . . 178.67(14) ?
C11 C1 C2 C3 . . . . 179.27(13) ?
C10 C1 C2 C3 . . . . 58.29(17) ?
C9 C1 C2 C3 . . . . -60.33(16) ?
C1 C2 C3 C8 . . . . -59.13(17) ?
C1 C2 C3 C4 . . . . 61.03(17) ?
C8 C3 C4 C5 . . . . 59.27(17) ?
C2 C3 C4 C5 . . . . -60.79(17) ?
C3 C4 C5 C9 . . . . 60.18(17) ?
C3 C4 C5 C6 . . . . -59.74(17) ?
C4 C5 C6 C7 . . . . 60.22(18) ?
C9 C5 C6 C7 . . . . -59.97(18) ?
C5 C6 C7 C10 . . . . 59.72(18) ?
C5 C6 C7 C8 . . . . -59.99(18) ?
C4 C3 C8 C7 . . . . -58.87(18) ?
C2 C3 C8 C7 . . . . 60.61(18) ?
C6 C7 C8 C3 . . . . 59.44(17) ?
C10 C7 C8 C3 . . . . -60.78(17) ?
C4 C5 C9 C1 . . . . -59.58(17) ?
C6 C5 C9 C1 . . . . 60.39(17) ?
C11 C1 C9 C5 . . . . -178.64(13) ?
C10 C1 C9 C5 . . . . -59.78(17) ?
C2 C1 C9 C5 . . . . 59.34(16) ?
C6 C7 C10 C1 . . . . -59.86(18) ?
C8 C7 C10 C1 . . . . 60.24(17) ?
C11 C1 C10 C7 . . . . 178.20(13) ?
C9 C1 C10 C7 . . . . 59.33(17) ?
C2 C1 C10 C7 . . . . -59.24(17) ?
N2 N1 C11 O1 . . . . -7.1(2) ?
N2 N1 C11 C1 . . . . 170.95(13) ?
C10 C1 C11 O1 . . . . -5.6(2) ?
C9 C1 C11 O1 . . . . 113.00(17) ?
C2 C1 C11 O1 . . . . -126.86(16) ?
C10 C1 C11 N1 . . . . 176.36(14) ?
C9 C1 C11 N1 . . . . -65.00(17) ?
C2 C1 C11 N1 . . . . 55.14(18) ?
N1 N2 C12 C13 . . . . 176.98(14) ?
C15 N3 C13 C14 . . . . -0.20(18) ?
C15 N3 C13 C12 . . . . -179.78(15) ?
N2 C12 C13 C14 . . . . 174.59(17) ?
N2 C12 C13 N3 . . . . -6.0(2) ?
C15 N4 C14 C13 . . . . -0.44(19) ?
C15 N4 C14 Cl1 . . . . 178.68(12) ?
N3 C13 C14 N4 . . . . 0.40(18) ?
C12 C13 C14 N4 . . . . 179.91(17) ?
N3 C13 C14 Cl1 . . . . -178.66(12) ?
C12 C13 C14 Cl1 . . . . 0.8(3) ?
C14 N4 C15 N3 . . . . 0.30(19) ?
C14 N4 C15 C16 . . . . -178.97(16) ?
C13 N3 C15 N4 . . . . -0.06(19) ?
C13 N3 C15 C16 . . . . 179.20(15) ?
N4 C15 C16 C17 . . . . 84.5(2) ?
N3 C15 C16 C17 . . . . -94.6(2) ?
C15 C16 C17 C18 . . . . 76.1(2) ?
C16 C17 C18 C19 . . . . 179.65(17) ?
C30 C20 C21 C22 . . . . 179.26(13) ?
C25 C20 C21 C22 . . . . -59.15(17) ?
C29 C20 C21 C22 . . . . 58.94(17) ?
C20 C21 C22 C23 . . . . 60.07(17) ?
C20 C21 C22 C28 . . . . -60.09(17) ?
C28 C22 C23 C24 . . . . 59.73(17) ?
C21 C22 C23 C24 . . . . -60.19(17) ?
C22 C23 C24 C26 . . . . -60.06(17) ?
C22 C23 C24 C25 . . . . 60.10(18) ?
C30 C20 C25 C24 . . . . -177.94(13) ?
C21 C20 C25 C24 . . . . 58.94(17) ?
C29 C20 C25 C24 . . . . -59.30(17) ?
C23 C24 C25 C20 . . . . -60.05(18) ?
C26 C24 C25 C20 . . . . 60.30(18) ?
C23 C24 C26 C27 . . . . 60.04(17) ?
C25 C24 C26 C27 . . . . -60.28(18) ?
C24 C26 C27 C28 . . . . -59.71(17) ?
C24 C26 C27 C29 . . . . 60.39(17) ?
C26 C27 C28 C22 . . . . 59.40(17) ?
C29 C27 C28 C22 . . . . -60.76(17) ?
C23 C22 C28 C27 . . . . -59.40(17) ?
C21 C22 C28 C27 . . . . 60.66(17) ?
C26 C27 C29 C20 . . . . -60.15(17) ?
C28 C27 C29 C20 . . . . 60.16(17) ?
C30 C20 C29 C27 . . . . 178.60(13) ?
C25 C20 C29 C27 . . . . 59.28(17) ?
C21 C20 C29 C27 . . . . -58.88(17) ?
N7 N8 C30 O2 . . . . 0.1(2) ?
N7 N8 C30 C20 . . . . -179.67(12) ?
C25 C20 C30 O2 . . . . 17.2(2) ?
C21 C20 C30 O2 . . . . 138.20(15) ?
C29 C20 C30 O2 . . . . -101.38(17) ?
C25 C20 C30 N8 . . . . -163.04(13) ?
C21 C20 C30 N8 . . . . -42.05(18) ?
C29 C20 C30 N8 . . . . 78.37(16) ?
N8 N7 C31 C32 . . . . 178.15(13) ?
C34 N6 C32 C33 . . . . 0.49(17) ?
C34 N6 C32 C31 . . . . -176.12(14) ?
N7 C31 C32 C33 . . . . -173.00(17) ?
N7 C31 C32 N6 . . . . 2.4(2) ?
N6 C32 C33 N5 . . . . -0.36(18) ?
C31 C32 C33 N5 . . . . 175.66(16) ?
N6 C32 C33 Cl2 . . . . -178.57(12) ?
C31 C32 C33 Cl2 . . . . -2.6(3) ?
C34 N5 C33 C32 . . . . 0.08(18) ?
C34 N5 C33 Cl2 . . . . 178.41(12) ?
C33 N5 C34 N6 . . . . 0.24(17) ?
C33 N5 C34 C35 . . . . -179.45(15) ?
C32 N6 C34 N5 . . . . -0.47(18) ?
C32 N6 C34 C35 . . . . 179.23(15) ?
N5 C34 C35 C36 . . . . -63.0(2) ?
N6 C34 C35 C36 . . . . 117.35(17) ?
C34 C35 C36 C37 . . . . -56.7(2) ?
C35 C36 C37 C38 . . . . -176.31(15) ?
