#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229989.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_2229989
loop_
_publ_author_name
'Harrad, Mohamed Anoir'
'Boualy, Brahim'
'Ali, Mustapha Ait'
'Firdoussi, Larbi El'
'Rizzoli, Corrado'
_publ_section_title
;
 rac-Ethyl
 (2Z)-3-{2-[(Z)-4-ethoxy-4-oxobut-2-en-2-ylamino]cyclohexylamino}but-2-enoate
;
_journal_coeditor_code           GK2371
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1269
_journal_page_last               o1270
_journal_paper_doi               10.1107/S1600536811015248
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H30 N2 O4'
_chemical_formula_moiety         'C18 H30 N2 O4'
_chemical_formula_sum            'C18 H30 N2 O4'
_chemical_formula_weight         338.44
_chemical_name_systematic
;
rac-Ethyl (2Z)-3-{2-[(Z)-4-ethoxy-
4-oxobut-2-en-2-ylamino]cyclohexylamino}but-2-enoate
;
_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
_cell_angle_alpha                90.904(6)
_cell_angle_beta                 109.222(6)
_cell_angle_gamma                114.048(5)
_cell_formula_units_Z            4
_cell_length_a                   11.1424(9)
_cell_length_b                   12.7445(6)
_cell_length_c                   16.3298(11)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      18.40
_cell_volume                     1969.1(3)
_computing_cell_refinement       'AED (Belletti et al., 1993)'
_computing_data_collection       'AED (Belletti et al., 1993)'
_computing_data_reduction        'AED (Belletti et al., 1993)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97
(Keller, 1997)
;
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Siemens AED'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0055
_diffrn_reflns_av_sigmaI/netI    0.0083
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7461
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0.02
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.135
_refine_ls_extinction_coef       0.0100(5)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         7189
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0341
_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)+(0.0604P)²+0.0296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                5826
_reflns_number_total             7189
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2371.cif
_cod_data_source_block           I
_cod_database_code               2229989
_cod_database_fobs_code          2229989
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.65218(9) 0.84797(6) 0.08853(5) 0.0814(2) Uani d . 1 1 . .
O O2 0.58185(10) 0.74147(7) -0.04449(5) 0.0864(2) Uani d . 1 1 . .
O O3 0.11165(8) 0.64888(7) 0.18740(5) 0.0774(2) Uani d . 1 1 . .
O O4 -0.03250(9) 0.73472(8) 0.13437(6) 0.0912(3) Uani d . 1 1 . .
O O5 -0.19007(10) 0.18776(8) 0.38766(5) 0.0895(3) Uani d . 1 1 A .
O O6A -0.1211(2) 0.10330(16) 0.50344(14) 0.0829(5) Uani d PD 0.704(2) 1 A 1
O O6B -0.0647(6) 0.1425(4) 0.5121(4) 0.0829(5) Uani d PD 0.296(2) 1 A 2
O O7 0.34330(8) 0.27768(7) 0.26921(6) 0.0846(2) Uani d . 1 1 . .
O O8 0.52581(9) 0.38869(8) 0.39309(7) 0.0963(3) Uani d D 1 1 . .
N N1 0.55037(10) 0.72198(8) 0.20595(6) 0.0684(2) Uani d . 1 1 . .
H H1N 0.5994(13) 0.7854(12) 0.1927(8) 0.082(4) Uiso d . 1 1 . .
N N2 0.38841(10) 0.79819(8) 0.27442(7) 0.0727(2) Uani d . 1 1 . .
H H2N 0.3211(14) 0.7281(12) 0.2553(8) 0.084(4) Uiso d . 1 1 . .
N N3 -0.13927(10) 0.13606(8) 0.24363(6) 0.0687(2) Uani d . 1 1 . .
H H3N -0.1697(13) 0.1707(11) 0.2705(8) 0.080(4) Uiso d . 1 1 . .
N N4 0.11045(10) 0.32223(9) 0.23049(6) 0.0719(2) Uani d . 1 1 . .
H H4N 0.1472(13) 0.2852(11) 0.2165(8) 0.082(4) Uiso d . 1 1 . .
C C1 0.55684(11) 0.71559(9) 0.29601(6) 0.0635(2) Uani d . 1 1 . .
H H1 0.4829 0.6400 0.2960 0.076 Uiso calc R 1 1 . .
C C2 0.69934(12) 0.72291(10) 0.35581(8) 0.0756(3) Uani d . 1 1 . .
H H2A 0.7131 0.6592 0.3338 0.091 Uiso calc R 1 1 . .
H H2B 0.7744 0.7955 0.3542 0.091 Uiso calc R 1 1 . .
C C3 0.70863(14) 0.71697(11) 0.45078(8) 0.0846(3) Uani d . 1 1 . .
H H3A 0.6395 0.6415 0.4536 0.102 Uiso calc R 1 1 . .
H H3B 0.8018 0.7256 0.4871 0.102 Uiso calc R 1 1 . .
C C4 0.68137(14) 0.81250(11) 0.48572(8) 0.0863(3) Uani d . 1 1 . .
H H4A 0.7565 0.8879 0.4890 0.104 Uiso calc R 1 1 . .
H H4B 0.6816 0.8045 0.5447 0.104 Uiso calc R 1 1 . .
C C5 0.53939(13) 0.80654(11) 0.42641(8) 0.0819(3) Uani d . 1 1 . .
H H5A 0.4639 0.7346 0.4285 0.098 Uiso calc R 1 1 . .
H H5B 0.5272 0.8710 0.4487 0.098 Uiso calc R 1 1 . .
C C6 0.52777(11) 0.81168(9) 0.33084(7) 0.0664(2) Uani d . 1 1 . .
H H6 0.5987 0.8876 0.3285 0.080 Uiso calc R 1 1 . .
C C7 0.48965(10) 0.63196(8) 0.13905(6) 0.0608(2) Uani d . 1 1 . .
C C8 0.40309(15) 0.51312(10) 0.15353(9) 0.0937(4) Uani d . 1 1 . .
H H8A 0.4628 0.4896 0.1987 0.141 Uiso calc R 1 1 . .
H H8B 0.3609 0.4582 0.0998 0.141 Uiso calc R 1 1 . .
H H8C 0.3302 0.5155 0.1714 0.141 Uiso calc R 1 1 . .
C C9 0.50447(10) 0.64528(9) 0.05978(7) 0.0648(2) Uani d . 1 1 . .
H H9 0.4586 0.5793 0.0162 0.078 Uiso calc R 1 1 . .
C C10 0.58526(11) 0.75309(9) 0.03918(7) 0.0655(2) Uani d . 1 1 . .
C C11 0.65923(17) 0.84598(13) -0.07360(9) 0.0971(4) Uani d . 1 1 . .
H H11A 0.6510 0.9113 -0.0488 0.117 Uiso calc R 1 1 . .
H H11B 0.6176 0.8358 -0.1372 0.117 Uiso calc R 1 1 . .
C C12 0.80899(19) 0.87259(17) -0.04739(13) 0.1255(6) Uani d . 1 1 . .
H H12A 0.8566 0.9426 -0.0674 0.188 Uiso calc R 1 1 . .
H H12B 0.8177 0.8091 -0.0732 0.188 Uiso calc R 1 1 . .
H H12C 0.8508 0.8836 0.0156 0.188 Uiso calc R 1 1 . .
C C13 0.34359(13) 0.88097(10) 0.25392(8) 0.0779(3) Uani d . 1 1 . .
C C14 0.45322(18) 1.00673(12) 0.28361(13) 0.1315(7) Uani d . 1 1 . .
H H14A 0.4072 1.0572 0.2707 0.197 Uiso calc R 1 1 . .
H H14B 0.5175 1.0224 0.2531 0.197 Uiso calc R 1 1 . .
H H14C 0.5046 1.0204 0.3459 0.197 Uiso calc R 1 1 . .
C C15 0.20513(13) 0.85458(10) 0.20757(7) 0.0795(3) Uani d . 1 1 . .
H H15 0.1805 0.9157 0.1951 0.095 Uiso calc R 1 1 . .
C C16 0.09706(12) 0.73879(10) 0.17749(7) 0.0699(3) Uani d . 1 1 . .
C C17 -0.15032(13) 0.61954(12) 0.10095(8) 0.0878(4) Uani d . 1 1 . .
H H17A -0.1213 0.5689 0.0757 0.105 Uiso calc R 1 1 . .
H H17B -0.2272 0.6252 0.0544 0.105 Uiso calc R 1 1 . .
C C18 -0.20206(15) 0.56635(16) 0.17051(10) 0.1087(5) Uani d . 1 1 . .
H H18A -0.2798 0.4907 0.1452 0.163 Uiso calc R 1 1 . .
H H18B -0.2327 0.6153 0.1950 0.163 Uiso calc R 1 1 . .
H H18C -0.1270 0.5587 0.2161 0.163 Uiso calc R 1 1 . .
C C19 -0.13341(11) 0.16744(9) 0.15936(7) 0.0646(2) Uani d . 1 1 . .
H H19 -0.0979 0.1202 0.1354 0.077 Uiso calc R 1 1 . .
C C20 -0.28197(12) 0.14077(10) 0.09474(7) 0.0760(3) Uani d . 1 1 . .
H H20A -0.3426 0.0579 0.0856 0.091 Uiso calc R 1 1 . .
H H20B -0.3214 0.1824 0.1197 0.091 Uiso calc R 1 1 . .
C C21 -0.27846(14) 0.17667(11) 0.00643(8) 0.0837(3) Uani d . 1 1 . .
H H21A -0.2467 0.1302 -0.0209 0.100 Uiso calc R 1 1 . .
H H21B -0.3730 0.1616 -0.0324 0.100 Uiso calc R 1 1 . .
C C22 -0.18062(14) 0.30461(12) 0.01838(8) 0.0833(3) Uani d . 1 1 . .
H H22A -0.2169 0.3513 0.0410 0.100 Uiso calc R 1 1 . .
H H22B -0.1776 0.3245 -0.0382 0.100 Uiso calc R 1 1 . .
C C23 -0.03151(13) 0.33309(12) 0.08190(8) 0.0817(3) Uani d . 1 1 . .
H H23A 0.0276 0.4162 0.0908 0.098 Uiso calc R 1 1 . .
H H23B 0.0085 0.2926 0.0565 0.098 Uiso calc R 1 1 . .
C C24 -0.03252(11) 0.29689(9) 0.17064(7) 0.0652(2) Uani d . 1 1 . .
H H24 -0.0665 0.3432 0.1971 0.078 Uiso calc R 1 1 . .
C C25 -0.07559(10) 0.07824(8) 0.29520(7) 0.0607(2) Uani d . 1 1 . .
C C26 -0.00907(14) 0.01806(11) 0.25829(8) 0.0788(3) Uani d . 1 1 . .
H H26A 0.0647 0.0746 0.2427 0.118 Uiso calc R 1 1 . .
H H26B -0.0793 -0.0381 0.2069 0.118 Uiso calc R 1 1 . .
H H26C 0.0300 -0.0209 0.3017 0.118 Uiso calc R 1 1 . .
C C27 -0.07262(11) 0.07126(9) 0.37959(7) 0.0654(2) Uani d . 1 1 A .
H H27 -0.0317 0.0267 0.4114 0.078 Uiso calc R 1 1 . .
C C28 -0.12888(13) 0.12870(9) 0.42072(7) 0.0725(3) Uani d . 1 1 . .
C C29A -0.1870(3) 0.14951(19) 0.54811(14) 0.0902(5) Uani d PD 0.704(2) 1 A 1
H H29A -0.2160 0.0993 0.5888 0.108 Uiso calc PR 0.704(2) 1 A 1
H H29B -0.2707 0.1505 0.5052 0.108 Uiso calc PR 0.704(2) 1 A 1
C C30A -0.0877(3) 0.2695(2) 0.59710(16) 0.1157(7) Uani d PD 0.704(2) 1 A 1
H H30A -0.1333 0.2985 0.6259 0.174 Uiso calc PR 0.704(2) 1 A 1
H H30B -0.0598 0.3194 0.5568 0.174 Uiso calc PR 0.704(2) 1 A 1
H H30C -0.0056 0.2683 0.6403 0.174 Uiso calc PR 0.704(2) 1 A 1
C C29B -0.0883(6) 0.2124(5) 0.5686(3) 0.0902(5) Uani d PD 0.296(2) 1 A 2
H H29C -0.0699 0.2880 0.5509 0.108 Uiso calc PR 0.296(2) 1 A 2
H H29D -0.0242 0.2246 0.6288 0.108 Uiso calc PR 0.296(2) 1 A 2
C C30B -0.2357(7) 0.1538(6) 0.5640(4) 0.1157(7) Uani d PD 0.296(2) 1 A 2
H H30D -0.2509 0.2013 0.6020 0.174 Uiso calc PR 0.296(2) 1 A 2
H H30E -0.2532 0.0796 0.5824 0.174 Uiso calc PR 0.296(2) 1 A 2
H H30F -0.2988 0.1424 0.5045 0.174 Uiso calc PR 0.296(2) 1 A 2
C C31 0.18551(11) 0.39366(9) 0.30854(7) 0.0653(2) Uani d . 1 1 B .
C C32 0.11850(15) 0.45730(13) 0.34209(8) 0.0911(4) Uani d . 1 1 . .
H H32A 0.0876 0.5000 0.2987 0.137 Uiso calc R 1 1 . .
H H32B 0.1863 0.5105 0.3955 0.137 Uiso calc R 1 1 . .
H H32C 0.0389 0.4020 0.3535 0.137 Uiso calc R 1 1 . .
C C33 0.32099(11) 0.41186(9) 0.35799(7) 0.0692(3) Uani d . 1 1 . .
H H33 0.3689 0.4659 0.4101 0.083 Uiso calc R 1 1 B .
C C34 0.39224(11) 0.35293(9) 0.33421(8) 0.0701(3) Uani d . 1 1 B .
C C35A 0.6064(10) 0.3370(8) 0.3684(8) 0.1107(14) Uani d PD 0.505(3) 1 B 1
H H35A 0.5625 0.3052 0.3059 0.133 Uiso calc PR 0.505(3) 1 B 1
H H35B 0.6079 0.2739 0.4005 0.133 Uiso calc PR 0.505(3) 1 B 1
C C36A 0.7530(4) 0.4278(3) 0.3891(3) 0.1138(9) Uani d PD 0.505(3) 1 B 1
H H36A 0.8069 0.3938 0.3736 0.171 Uiso calc PR 0.505(3) 1 B 1
H H36B 0.7958 0.4591 0.4509 0.171 Uiso calc PR 0.505(3) 1 B 1
H H36C 0.7510 0.4891 0.3561 0.171 Uiso calc PR 0.505(3) 1 B 1
C C35B 0.6115(10) 0.3321(9) 0.3864(8) 0.1107(14) Uani d PD 0.495(3) 1 B 2
H H35C 0.5535 0.2491 0.3655 0.133 Uiso calc PR 0.495(3) 1 B 2
H H35D 0.6832 0.3434 0.4435 0.133 Uiso calc PR 0.495(3) 1 B 2
C C36B 0.6779(4) 0.3848(3) 0.3239(3) 0.1138(9) Uani d PD 0.495(3) 1 B 2
H H36D 0.7310 0.3454 0.3148 0.171 Uiso calc PR 0.495(3) 1 B 2
H H36E 0.7401 0.4658 0.3472 0.171 Uiso calc PR 0.495(3) 1 B 2
H H36F 0.6062 0.3777 0.2688 0.171 Uiso calc PR 0.495(3) 1 B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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 0.0181 0.0091 '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
C10 O2 C11 . . 117.28(10) ?
C16 O4 C17 . . 116.58(9) ?
C28 O6A C29A . . 117.05(18) ?
C28 O6B C29B . . 119.8(5) ?
C34 O8 C35B . . 121.2(5) ?
C34 O8 C35A . . 114.2(5) ?
C7 N1 C1 . . 126.83(9) ?
C7 N1 H1N . . 111.8(8) ?
C1 N1 H1N . . 120.6(8) ?
C13 N2 C6 . . 128.79(10) ?
C13 N2 H2N . . 113.1(8) ?
C6 N2 H2N . . 117.7(8) ?
C25 N3 C19 . . 128.67(9) ?
C25 N3 H3N . . 112.5(8) ?
C19 N3 H3N . . 117.2(8) ?
C31 N4 C24 . . 128.22(9) ?
C31 N4 H4N . . 115.3(9) ?
C24 N4 H4N . . 116.3(9) ?
N1 C1 C2 . . 111.09(9) ?
N1 C1 C6 . . 110.54(8) ?
C2 C1 C6 . . 110.93(8) ?
N1 C1 H1 . . 108.0 ?
C2 C1 H1 . . 108.0 ?
C6 C1 H1 . . 108.0 ?
C3 C2 C1 . . 111.95(9) ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C4 C3 C2 . . 110.45(10) ?
C4 C3 H3A . . 109.6 ?
C2 C3 H3A . . 109.6 ?
C4 C3 H3B . . 109.6 ?
C2 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
C3 C4 C5 . . 111.02(10) ?
C3 C4 H4A . . 109.4 ?
C5 C4 H4A . . 109.4 ?
C3 C4 H4B . . 109.4 ?
C5 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C6 C5 C4 . . 112.53(10) ?
C6 C5 H5A . . 109.1 ?
C4 C5 H5A . . 109.1 ?
C6 C5 H5B . . 109.1 ?
C4 C5 H5B . . 109.1 ?
H5A C5 H5B . . 107.8 ?
N2 C6 C5 . . 111.60(9) ?
N2 C6 C1 . . 109.13(8) ?
C5 C6 C1 . . 110.09(9) ?
N2 C6 H6 . . 108.7 ?
C5 C6 H6 . . 108.7 ?
C1 C6 H6 . . 108.7 ?
N1 C7 C9 . . 122.42(9) ?
N1 C7 C8 . . 118.00(10) ?
C9 C7 C8 . . 119.59(9) ?
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 ?
C7 C9 C10 . . 124.40(9) ?
C7 C9 H9 . . 117.8 ?
C10 C9 H9 . . 117.8 ?
O1 C10 O2 . . 121.51(10) ?
O1 C10 C9 . . 126.35(10) ?
O2 C10 C9 . . 112.14(9) ?
O2 C11 C12 . . 112.02(12) ?
O2 C11 H11A . . 109.2 ?
C12 C11 H11A . . 109.2 ?
O2 C11 H11B . . 109.2 ?
C12 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N2 C13 C15 . . 122.28(11) ?
N2 C13 C14 . . 117.39(11) ?
C15 C13 C14 . . 120.33(11) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 C16 . . 123.31(10) ?
C13 C15 H15 . . 118.3 ?
C16 C15 H15 . . 118.3 ?
O3 C16 O4 . . 120.92(10) ?
O3 C16 C15 . . 126.59(10) ?
O4 C16 C15 . . 112.49(10) ?
O4 C17 C18 . . 112.64(11) ?
O4 C17 H17A . . 109.1 ?
C18 C17 H17A . . 109.1 ?
O4 C17 H17B . . 109.1 ?
C18 C17 H17B . . 109.1 ?
H17A C17 H17B . . 107.8 ?
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 ?
N3 C19 C20 . . 109.91(9) ?
N3 C19 C24 . . 110.78(8) ?
C20 C19 C24 . . 110.58(8) ?
N3 C19 H19 . . 108.5 ?
C20 C19 H19 . . 108.5 ?
C24 C19 H19 . . 108.5 ?
C21 C20 C19 . . 111.11(10) ?
C21 C20 H20A . . 109.4 ?
C19 C20 H20A . . 109.4 ?
C21 C20 H20B . . 109.4 ?
C19 C20 H20B . . 109.4 ?
H20A C20 H20B . . 108.0 ?
C22 C21 C20 . . 111.03(10) ?
C22 C21 H21A . . 109.4 ?
C20 C21 H21A . . 109.4 ?
C22 C21 H21B . . 109.4 ?
C20 C21 H21B . . 109.4 ?
H21A C21 H21B . . 108.0 ?
C21 C22 C23 . . 111.17(10) ?
C21 C22 H22A . . 109.4 ?
C23 C22 H22A . . 109.4 ?
C21 C22 H22B . . 109.4 ?
C23 C22 H22B . . 109.4 ?
H22A C22 H22B . . 108.0 ?
C22 C23 C24 . . 111.12(9) ?
C22 C23 H23A . . 109.4 ?
C24 C23 H23A . . 109.4 ?
C22 C23 H23B . . 109.4 ?
C24 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
N4 C24 C23 . . 110.76(9) ?
N4 C24 C19 . . 110.83(8) ?
C23 C24 C19 . . 111.46(9) ?
N4 C24 H24 . . 107.9 ?
C23 C24 H24 . . 107.9 ?
C19 C24 H24 . . 107.9 ?
N3 C25 C27 . . 121.75(9) ?
N3 C25 C26 . . 118.67(9) ?
C27 C25 C26 . . 119.57(9) ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C25 C27 C28 . . 123.28(9) ?
C25 C27 H27 . . 118.4 ?
C28 C27 H27 . . 118.4 ?
O5 C28 O6A . . 120.10(13) ?
O5 C28 O6B . . 121.0(2) ?
O5 C28 C27 . . 126.94(10) ?
O6A C28 C27 . . 112.70(12) ?
O6B C28 C27 . . 108.9(3) ?
O6A C29A C30A . . 110.8(2) ?
O6A C29A H29A . . 109.5 ?
C30A C29A H29A . . 109.5 ?
O6A C29A H29B . . 109.5 ?
C30A C29A H29B . . 109.5 ?
H29A C29A H29B . . 108.1 ?
C29A C30A H30A . . 109.5 ?
C29A C30A H30B . . 109.5 ?
H30A C30A H30B . . 109.5 ?
C29A C30A H30C . . 109.5 ?
H30A C30A H30C . . 109.5 ?
H30B C30A H30C . . 109.5 ?
O6B C29B C30B . . 109.9(5) ?
O6B C29B H29C . . 109.7 ?
C30B C29B H29C . . 109.7 ?
O6B C29B H29D . . 109.7 ?
C30B C29B H29D . . 109.7 ?
H29C C29B H29D . . 108.2 ?
C29B C30B H30D . . 109.5 ?
C29B C30B H30E . . 109.5 ?
H30D C30B H30E . . 109.5 ?
C29B C30B H30F . . 109.5 ?
H30D C30B H30F . . 109.5 ?
H30E C30B H30F . . 109.5 ?
N4 C31 C33 . . 122.59(10) ?
N4 C31 C32 . . 118.16(10) ?
C33 C31 C32 . . 119.25(10) ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C31 C33 C34 . . 123.87(10) ?
C31 C33 H33 . . 118.1 ?
C34 C33 H33 . . 118.1 ?
O7 C34 O8 . . 121.61(10) ?
O7 C34 C33 . . 126.26(10) ?
O8 C34 C33 . . 112.13(10) ?
O8 C35A C36A . . 109.2(6) ?
O8 C35A H35A . . 109.8 ?
C36A C35A H35A . . 109.8 ?
O8 C35A H35B . . 109.8 ?
C36A C35A H35B . . 109.8 ?
H35A C35A H35B . . 108.3 ?
C35A C36A H36A . . 109.5 ?
C35A C36A H36B . . 109.5 ?
H36A C36A H36B . . 109.5 ?
C35A C36A H36C . . 109.5 ?
H36A C36A H36C . . 109.5 ?
H36B C36A H36C . . 109.5 ?
O8 C35B C36B . . 107.3(7) ?
O8 C35B H35C . . 110.3 ?
C36B C35B H35C . . 110.3 ?
O8 C35B H35D . . 110.3 ?
C36B C35B H35D . . 110.3 ?
H35C C35B H35D . . 108.5 ?
C35B C36B H36D . . 109.5 ?
C35B C36B H36E . . 109.5 ?
H36D C36B H36E . . 109.5 ?
C35B C36B H36F . . 109.5 ?
H36D C36B H36F . . 109.5 ?
H36E C36B H36F . . 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
O1 C10 . 1.2273(12) ?
O2 C10 . 1.3584(13) ?
O2 C11 . 1.4482(15) ?
O3 C16 . 1.2272(13) ?
O4 C16 . 1.3605(13) ?
O4 C17 . 1.4520(16) ?
O5 C28 . 1.2294(13) ?
O6A C28 . 1.377(2) ?
O6A C29A . 1.453(3) ?
O6B C28 . 1.398(6) ?
O6B C29B . 1.429(6) ?
O7 C34 . 1.2264(14) ?
O8 C34 . 1.3558(13) ?
O8 C35B . 1.439(7) ?
O8 C35A . 1.455(7) ?
N1 C7 . 1.3448(13) ?
N1 C1 . 1.4538(13) ?
N1 H1N . 0.850(13) ?
N2 C13 . 1.3435(14) ?
N2 C6 . 1.4577(13) ?
N2 H2N . 0.865(13) ?
N3 C25 . 1.3446(13) ?
N3 C19 . 1.4537(13) ?
N3 H3N . 0.847(13) ?
N4 C31 . 1.3392(14) ?
N4 C24 . 1.4639(13) ?
N4 H4N . 0.811(13) ?
C1 C2 . 1.5293(14) ?
C1 C6 . 1.5332(15) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.5251(16) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.5145(18) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.5288(18) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.5277(15) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6 . 0.9800 ?
C7 C9 . 1.3626(14) ?
C7 C8 . 1.5003(15) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.4202(14) ?
C9 H9 . 0.9300 ?
C11 C12 . 1.465(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C15 . 1.3662(17) ?
C13 C14 . 1.5119(18) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C16 . 1.4172(16) ?
C15 H15 . 0.9300 ?
C17 C18 . 1.490(2) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 C20 . 1.5327(14) ?
C19 C24 . 1.5368(15) ?
C19 H19 . 0.9800 ?
C20 C21 . 1.5277(16) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 C22 . 1.5121(19) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 C23 . 1.5264(17) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 C24 . 1.5298(14) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 H24 . 0.9800 ?
C25 C27 . 1.3727(14) ?
C25 C26 . 1.4979(14) ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
C27 C28 . 1.4197(15) ?
C27 H27 . 0.9300 ?
C29A C30A . 1.484(3) ?
C29A H29A . 0.9700 ?
C29A H29B . 0.9700 ?
C30A H30A . 0.9600 ?
C30A H30B . 0.9600 ?
C30A H30C . 0.9600 ?
C29B C30B . 1.475(7) ?
C29B H29C . 0.9700 ?
C29B H29D . 0.9700 ?
C30B H30D . 0.9600 ?
C30B H30E . 0.9600 ?
C30B H30F . 0.9600 ?
C31 C33 . 1.3751(15) ?
C31 C32 . 1.5048(15) ?
C32 H32A . 0.9600 ?
C32 H32B . 0.9600 ?
C32 H32C . 0.9600 ?
C33 C34 . 1.4231(15) ?
C33 H33 . 0.9300 ?
C35A C36A . 1.485(9) ?
C35A H35A . 0.9700 ?
C35A H35B . 0.9700 ?
C36A H36A . 0.9600 ?
C36A H36B . 0.9600 ?
C36A H36C . 0.9600 ?
C35B C36B . 1.468(9) ?
C35B H35C . 0.9700 ?
C35B H35D . 0.9700 ?
C36B H36D . 0.9600 ?
C36B H36E . 0.9600 ?
C36B H36F . 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
N1 H1N O1 . 0.850(13) 2.048(14) 2.754(2) 140.1(12)
N2 H2N O3 . 0.865(12) 2.009(12) 2.720(2) 138.7(13)
N3 H3N O5 . 0.846(17) 2.018(15) 2.724(2) 140.3(12)
N4 H4N O7 . 0.811(17) 2.112(15) 2.754(2) 136.1(14)
C4 H4A O6A 1_665 0.97 2.48 3.400(3) 158
