#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/89/2018924.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_2018924
loop_
_publ_author_name
'Sandhu, Bhupinder'
'Draguta, Sergiu'
'Kinnibrugh, Tiffany L.'
'Khrustalev, Victor N.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 Supramolecular synthesis based on piperidone derivatives and
 pharmaceutically acceptable co-formers
;
_journal_coeditor_code           QS3023
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              421
_journal_page_last               427
_journal_paper_doi               10.1107/S0108270113006185
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '2C27 H36 N3 O + , C4 H4 O4 2-'
_chemical_formula_moiety         '2(C27 H36 N3 O +), C4 H4 O4 2-'
_chemical_formula_sum            'C58 H76 N6 O6'
_chemical_formula_weight         953.27
_chemical_name_systematic
;
Bis{(E,E)-3,5-bis[4-(diethylamino)benzylidene]-4-oxopiperidinium}
butanedioate
;
_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           SHELXL97
_cell_angle_alpha                96.320(3)
_cell_angle_beta                 92.211(3)
_cell_angle_gamma                95.861(3)
_cell_formula_units_Z            2
_cell_length_a                   11.1075(15)
_cell_length_b                   12.9650(18)
_cell_length_c                   17.899(3)
_cell_measurement_reflns_used    4344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.21
_cell_volume                     2545.3(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (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 APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16330
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.515
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     647
_refine_ls_number_reflns         9952
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0666
_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)+(0.0897P)²+1.4P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1846
_reflns_number_gt                6795
_reflns_number_total             9952
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qs3023.cif
_cod_data_source_block           II
_cod_database_code               2018924
_cod_database_fobs_code          2018924
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 O1A 1.08996(17) 0.70377(16) 0.87565(11) 0.0340(5) Uani d . 1 1 . .
N N1A 0.8329(2) 0.65779(18) 0.70200(12) 0.0292(5) Uani d . 1 1 . .
H H1A 0.7842 0.6912 0.7335 0.035 Uiso d R 1 1 . .
H H1B 0.7948 0.6358 0.6549 0.035 Uiso d R 1 1 . .
N N2A 1.2124(4) 1.1885(2) 0.60754(14) 0.0719(12) Uani d D 1 1 . .
N N3A 0.60699(19) 0.18989(18) 0.94333(12) 0.0274(5) Uani d . 1 1 . .
C C2A 0.9450(2) 0.7225(2) 0.68893(14) 0.0283(6) Uani d . 1 1 . .
H H2A 0.9237 0.7859 0.6675 0.034 Uiso calc R 1 1 . .
H H2B 0.9912 0.6830 0.6514 0.034 Uiso calc R 1 1 . .
C C3A 1.0241(2) 0.7545(2) 0.75943(15) 0.0249(6) Uani d . 1 1 . .
C C4A 1.0192(2) 0.6846(2) 0.81997(15) 0.0256(6) Uani d . 1 1 . .
C C5A 0.9263(2) 0.5930(2) 0.81242(14) 0.0241(6) Uani d . 1 1 . .
C C6A 0.8555(3) 0.5653(2) 0.73858(15) 0.0302(6) Uani d . 1 1 . .
H H6A 0.9007 0.5194 0.7047 0.036 Uiso calc R 1 1 . .
H H6B 0.7770 0.5260 0.7471 0.036 Uiso calc R 1 1 . .
C C7A 1.0967(2) 0.8454(2) 0.77244(15) 0.0263(6) Uani d . 1 1 . .
H H7A 1.1371 0.8565 0.8209 0.032 Uiso calc R 1 1 . .
C C8A 1.1246(2) 0.9290(2) 0.72648(15) 0.0270(6) Uani d . 1 1 . .
C C9A 1.1204(3) 0.9191(2) 0.64753(17) 0.0392(7) Uani d . 1 1 A .
H H9A 1.0962 0.8526 0.6203 0.047 Uiso calc R 1 1 . .
C C10A 1.1502(4) 1.0027(3) 0.60840(18) 0.0497(9) Uani d . 1 1 . .
H H10A 1.1459 0.9926 0.5549 0.060 Uiso calc R 1 1 A .
C C11A 1.1873(3) 1.1039(2) 0.64603(17) 0.0428(8) Uani d . 1 1 A .
C C12A 1.1943(2) 1.1130(2) 0.72471(16) 0.0314(6) Uani d . 1 1 . .
H H12A 1.2197 1.1789 0.7524 0.038 Uiso calc R 1 1 A .
C C13A 1.1651(2) 1.0283(2) 0.76219(16) 0.0292(6) Uani d . 1 1 A .
H H13A 1.1727 1.0376 0.8156 0.035 Uiso calc R 1 1 . .
C C14A 1.1806(3) 1.1851(4) 0.52497(19) 0.0368(11) Uani d PD 0.631(6) 1 A 1
H H14A 1.1583 1.2539 0.5137 0.044 Uiso calc PR 0.631(6) 1 A 1
H H14B 1.1103 1.1324 0.5104 0.044 Uiso calc PR 0.631(6) 1 A 1
C C15A 1.2895(4) 1.1568(4) 0.4801(2) 0.0472(13) Uani d PD 0.631(6) 1 A 1
H H15A 1.2669 1.1492 0.4262 0.071 Uiso calc PR 0.631(6) 1 A 1
H H15B 1.3148 1.0909 0.4940 0.071 Uiso calc PR 0.631(6) 1 A 1
H H15C 1.3566 1.2122 0.4915 0.071 Uiso calc PR 0.631(6) 1 A 1
C C14C 1.2712(5) 1.1664(6) 0.5353(2) 0.0368(11) Uani d PD 0.37 1 A 2
H H14E 1.3034 1.0977 0.5332 0.044 Uiso calc PR 0.369(6) 1 A 2
H H14F 1.3398 1.2204 0.5315 0.044 Uiso calc PR 0.369(6) 1 A 2
C C15C 1.1780(7) 1.1659(8) 0.4696(2) 0.0472(13) Uani d PD 0.37 1 A 2
H H15G 1.2152 1.1468 0.4220 0.071 Uiso calc PR 0.369(6) 1 A 2
H H15H 1.1510 1.2355 0.4696 0.071 Uiso calc PR 0.369(6) 1 A 2
H H15I 1.1083 1.1151 0.4752 0.071 Uiso calc PR 0.369(6) 1 A 2
C C16A 1.2574(3) 1.2909(2) 0.64667(18) 0.0423(8) Uani d . 1 1 A .
H H16A 1.2104 1.3038 0.6920 0.051 Uiso calc R 1 1 . .
H H16B 1.2418 1.3447 0.6134 0.051 Uiso calc R 1 1 . .
C C17A 1.3906(3) 1.3044(3) 0.6704(2) 0.0558(10) Uani d . 1 1 . .
H H17A 1.4121 1.3743 0.6974 0.084 Uiso calc R 1 1 A .
H H17B 1.4386 1.2961 0.6258 0.084 Uiso calc R 1 1 . .
H H17C 1.4075 1.2517 0.7036 0.084 Uiso calc R 1 1 . .
C C18A 0.9078(2) 0.5437(2) 0.87439(15) 0.0273(6) Uani d . 1 1 . .
H H18A 0.9572 0.5737 0.9174 0.033 Uiso calc R 1 1 . .
C C19A 0.8261(2) 0.4532(2) 0.88704(14) 0.0261(6) Uani d . 1 1 . .
C C20A 0.7762(2) 0.3734(2) 0.83172(15) 0.0294(6) Uani d . 1 1 . .
H H20A 0.7931 0.3785 0.7805 0.035 Uiso calc R 1 1 . .
C C21A 0.7038(2) 0.2881(2) 0.84951(15) 0.0292(6) Uani d . 1 1 . .
H H21A 0.6724 0.2356 0.8104 0.035 Uiso calc R 1 1 . .
C C22A 0.6751(2) 0.2763(2) 0.92421(15) 0.0247(6) Uani d . 1 1 . .
C C23A 0.7251(2) 0.3564(2) 0.98010(15) 0.0249(6) Uani d . 1 1 . .
H H23A 0.7077 0.3521 1.0313 0.030 Uiso calc R 1 1 . .
C C24A 0.7982(2) 0.4401(2) 0.96141(14) 0.0245(6) Uani d . 1 1 . .
H H24A 0.8317 0.4916 1.0006 0.029 Uiso calc R 1 1 . .
C C25A 0.5669(2) 0.1008(2) 0.88766(16) 0.0305(6) Uani d . 1 1 . .
H H25A 0.5560 0.0370 0.9135 0.037 Uiso calc R 1 1 . .
H H25B 0.6310 0.0916 0.8513 0.037 Uiso calc R 1 1 . .
C C26A 0.4494(3) 0.1125(3) 0.84498(17) 0.0391(7) Uani d . 1 1 . .
H H26A 0.4250 0.0490 0.8106 0.059 Uiso calc R 1 1 . .
H H26B 0.4613 0.1723 0.8160 0.059 Uiso calc R 1 1 . .
H H26C 0.3861 0.1238 0.8807 0.059 Uiso calc R 1 1 . .
C C27A 0.5607(2) 0.1861(2) 1.01812(15) 0.0269(6) Uani d . 1 1 . .
H H27A 0.4814 0.1430 1.0137 0.032 Uiso calc R 1 1 . .
H H27B 0.5472 0.2576 1.0392 0.032 Uiso calc R 1 1 . .
C C28A 0.6443(2) 0.1420(2) 1.07231(16) 0.0308(6) Uani d . 1 1 . .
H H28A 0.6063 0.1388 1.1206 0.046 Uiso calc R 1 1 . .
H H28B 0.7212 0.1870 1.0799 0.046 Uiso calc R 1 1 . .
H H28C 0.6595 0.0717 1.0515 0.046 Uiso calc R 1 1 . .
O O2A 0.74229(17) 0.58814(18) 0.57166(11) 0.0394(5) Uani d . 1 1 . .
O O3A 0.57358(18) 0.5652(2) 0.63151(11) 0.0486(6) Uani d . 1 1 . .
C C29A 0.6289(2) 0.5587(2) 0.57354(14) 0.0268(6) Uani d . 1 1 . .
C C30A 0.5680(2) 0.5105(2) 0.49952(15) 0.0305(6) Uani d . 1 1 . .
H H30A 0.6015 0.4438 0.4845 0.037 Uiso calc R 1 1 . .
H H30B 0.5882 0.5575 0.4608 0.037 Uiso calc R 1 1 . .
O O1B 0.36751(17) 0.34005(17) 0.15765(12) 0.0404(5) Uani d . 1 1 . .
N N1B 0.63635(19) 0.35149(17) 0.31356(11) 0.0240(5) Uani d . 1 1 . .
H H1C 0.5822 0.3891 0.3372 0.029 Uiso d R 1 1 . .
H H1D 0.7004 0.3539 0.3494 0.029 Uiso d R 1 1 . .
N N2B 0.2396(2) -0.16004(19) 0.40590(14) 0.0355(6) Uani d . 1 1 . .
N N3B 0.90546(19) 0.76950(18) 0.02450(13) 0.0298(5) Uani d . 1 1 . .
C C2B 0.5783(2) 0.2450(2) 0.29200(15) 0.0268(6) Uani d . 1 1 . .
H H2C 0.5531 0.2140 0.3378 0.032 Uiso calc R 1 1 . .
H H2D 0.6378 0.2020 0.2677 0.032 Uiso calc R 1 1 . .
C C3B 0.4693(2) 0.2427(2) 0.23874(14) 0.0238(6) Uani d . 1 1 . .
C C4B 0.4620(2) 0.3319(2) 0.19360(15) 0.0266(6) Uani d . 1 1 . .
C C5B 0.5710(2) 0.4086(2) 0.19306(14) 0.0233(5) Uani d . 1 1 . .
C C6B 0.6763(2) 0.4015(2) 0.24740(14) 0.0245(6) Uani d . 1 1 . .
H H6C 0.7363 0.3607 0.2215 0.029 Uiso calc R 1 1 . .
H H6D 0.7164 0.4725 0.2641 0.029 Uiso calc R 1 1 . .
C C7B 0.3743(2) 0.1687(2) 0.23265(14) 0.0230(5) Uani d . 1 1 . .
H H7B 0.3138 0.1771 0.1954 0.028 Uiso calc R 1 1 . .
C C8B 0.3476(2) 0.0785(2) 0.27265(14) 0.0245(6) Uani d . 1 1 . .
C C9B 0.4326(2) 0.0286(2) 0.31196(15) 0.0269(6) Uani d . 1 1 . .
H H9B 0.5165 0.0509 0.3100 0.032 Uiso calc R 1 1 . .
C C10B 0.3976(2) -0.0510(2) 0.35273(16) 0.0291(6) Uani d . 1 1 . .
H H10B 0.4580 -0.0839 0.3773 0.035 Uiso calc R 1 1 . .
C C11B 0.2739(2) -0.0864(2) 0.35979(15) 0.0291(6) Uani d . 1 1 . .
C C12B 0.1891(2) -0.0404(2) 0.31694(15) 0.0300(6) Uani d . 1 1 . .
H H12B 0.1053 -0.0640 0.3173 0.036 Uiso calc R 1 1 . .
C C13B 0.2259(2) 0.0378(2) 0.27498(15) 0.0262(6) Uani d . 1 1 . .
H H13B 0.1664 0.0659 0.2460 0.031 Uiso calc R 1 1 . .
C C14B 0.3279(3) -0.2195(3) 0.43982(19) 0.0419(8) Uani d . 1 1 . .
H H14C 0.3933 -0.2303 0.4046 0.050 Uiso calc R 1 1 . .
H H14D 0.2877 -0.2889 0.4476 0.050 Uiso calc R 1 1 . .
C C15B 0.3832(3) -0.1653(3) 0.51439(19) 0.0540(10) Uani d . 1 1 . .
H H15D 0.4439 -0.2067 0.5338 0.081 Uiso calc R 1 1 . .
H H15E 0.3195 -0.1582 0.5505 0.081 Uiso calc R 1 1 . .
H H15F 0.4219 -0.0960 0.5072 0.081 Uiso calc R 1 1 . .
C C16B 0.1130(3) -0.1993(2) 0.41177(16) 0.0341(7) Uani d . 1 1 . .
H H16C 0.0623 -0.1409 0.4101 0.041 Uiso calc R 1 1 . .
H H16D 0.1031 -0.2267 0.4609 0.041 Uiso calc R 1 1 . .
C C17B 0.0692(3) -0.2850(3) 0.34902(18) 0.0462(8) Uani d . 1 1 . .
H H17D -0.0125 -0.3151 0.3587 0.069 Uiso calc R 1 1 . .
H H17E 0.1244 -0.3395 0.3470 0.069 Uiso calc R 1 1 . .
H H17F 0.0675 -0.2556 0.3009 0.069 Uiso calc R 1 1 . .
C C18B 0.5682(2) 0.4784(2) 0.14258(14) 0.0241(6) Uani d . 1 1 . .
H H18B 0.4918 0.4757 0.1162 0.029 Uiso calc R 1 1 . .
C C19B 0.6584(2) 0.5569(2) 0.12043(14) 0.0232(5) Uani d . 1 1 . .
C C20B 0.7802(2) 0.5779(2) 0.14715(14) 0.0242(6) Uani d . 1 1 . .
H H20B 0.8086 0.5409 0.1861 0.029 Uiso calc R 1 1 . .
C C21B 0.8595(2) 0.6505(2) 0.11854(14) 0.0246(6) Uani d . 1 1 . .
H H21B 0.9400 0.6647 0.1399 0.029 Uiso calc R 1 1 . .
C C22B 0.8243(2) 0.7046(2) 0.05833(15) 0.0257(6) Uani d . 1 1 . .
C C23B 0.7015(2) 0.6851(2) 0.03169(16) 0.0273(6) Uani d . 1 1 . .
H H23B 0.6731 0.7211 -0.0078 0.033 Uiso calc R 1 1 . .
C C24B 0.6229(2) 0.6140(2) 0.06267(15) 0.0260(6) Uani d . 1 1 . .
H H24B 0.5408 0.6032 0.0440 0.031 Uiso calc R 1 1 . .
C C25B 1.0324(2) 0.7902(2) 0.05277(16) 0.0289(6) Uani d . 1 1 . .
H H25C 1.0822 0.8134 0.0118 0.035 Uiso calc R 1 1 . .
H H25D 1.0603 0.7241 0.0661 0.035 Uiso calc R 1 1 . .
C C26B 1.0547(3) 0.8715(2) 0.12062(17) 0.0361(7) Uani d . 1 1 . .
H H26D 1.1415 0.8824 0.1349 0.054 Uiso calc R 1 1 . .
H H26E 1.0098 0.8475 0.1626 0.054 Uiso calc R 1 1 . .
H H26F 1.0271 0.9373 0.1082 0.054 Uiso calc R 1 1 . .
C C27B 0.8677(2) 0.8222(2) -0.03969(16) 0.0308(6) Uani d . 1 1 . .
H H27C 0.8102 0.7733 -0.0735 0.037 Uiso calc R 1 1 . .
H H27D 0.9395 0.8411 -0.0684 0.037 Uiso calc R 1 1 . .
C C28B 0.8084(3) 0.9193(2) -0.01591(19) 0.0406(8) Uani d . 1 1 . .
H H28D 0.7796 0.9486 -0.0607 0.061 Uiso calc R 1 1 . .
H H28E 0.8673 0.9708 0.0136 0.061 Uiso calc R 1 1 . .
H H28F 0.7396 0.9017 0.0148 0.061 Uiso calc R 1 1 . .
O O2B 0.80151(16) 0.35015(15) 0.41720(10) 0.0305(4) Uani d . 1 1 . .
O O3B 0.87862(18) 0.49971(16) 0.38002(11) 0.0380(5) Uani d . 1 1 . .
C C29B 0.8752(2) 0.4360(2) 0.42502(14) 0.0241(6) Uani d . 1 1 . .
C C30B 0.9598(2) 0.4489(2) 0.49504(15) 0.0254(6) Uani d . 1 1 . .
H H30C 0.9107 0.4443 0.5398 0.030 Uiso calc R 1 1 . .
H H30D 1.0112 0.3908 0.4921 0.030 Uiso calc R 1 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'
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
C6A N1A C2A . . 112.8(2)
C6A N1A H1A . . 103.7
C2A N1A H1A . . 113.2
C6A N1A H1B . . 108.5
C2A N1A H1B . . 106.5
H1A N1A H1B . . 112.2
C11A N2A C16A . . 121.4(3)
C11A N2A C14C . . 115.0(4)
C16A N2A C14C . . 112.1(4)
C11A N2A C14A . . 122.1(3)
C16A N2A C14A . . 116.0(3)
C22A N3A C27A . . 121.8(2)
C22A N3A C25A . . 121.6(2)
C27A N3A C25A . . 116.3(2)
N1A C2A C3A . . 112.9(2)
N1A C2A H2A . . 109.0
C3A C2A H2A . . 109.0
N1A C2A H2B . . 109.0
C3A C2A H2B . . 109.0
H2A C2A H2B . . 107.8
C7A C3A C4A . . 117.6(2)
C7A C3A C2A . . 123.8(2)
C4A C3A C2A . . 118.6(2)
O1A C4A C5A . . 121.1(2)
O1A C4A C3A . . 120.3(2)
C5A C4A C3A . . 118.6(2)
C18A C5A C4A . . 116.9(2)
C18A C5A C6A . . 124.9(2)
C4A C5A C6A . . 118.1(2)
N1A C6A C5A . . 112.3(2)
N1A C6A H6A . . 109.1
C5A C6A H6A . . 109.1
N1A C6A H6B . . 109.1
C5A C6A H6B . . 109.1
H6A C6A H6B . . 107.9
C3A C7A C8A . . 132.1(3)
C3A C7A H7A . . 113.9
C8A C7A H7A . . 113.9
C13A C8A C9A . . 115.5(3)
C13A C8A C7A . . 118.6(2)
C9A C8A C7A . . 125.9(3)
C10A C9A C8A . . 121.9(3)
C10A C9A H9A . . 119.0
C8A C9A H9A . . 119.0
C9A C10A C11A . . 121.5(3)
C9A C10A H10A . . 119.2
C11A C10A H10A . . 119.2
N2A C11A C12A . . 121.6(3)
N2A C11A C10A . . 121.9(3)
C12A C11A C10A . . 116.4(3)
C13A C12A C11A . . 120.8(3)
C13A C12A H12A . . 119.6
C11A C12A H12A . . 119.6
C12A C13A C8A . . 123.8(3)
C12A C13A H13A . . 118.1
C8A C13A H13A . . 118.1
N2A C14A C15A . . 109.4(2)
N2A C14A H14A . . 109.8
C15A C14A H14A . . 109.8
N2A C14A H14B . . 109.8
C15A C14A H14B . . 109.8
H14A C14A H14B . . 108.2
N2A C14C C15C . . 109.4(3)
N2A C14C H14E . . 109.8
C15C C14C H14E . . 109.8
N2A C14C H14F . . 109.8
C15C C14C H14F . . 109.8
H14E C14C H14F . . 108.2
C14C C15C H15G . . 109.5
C14C C15C H15H . . 109.5
H15G C15C H15H . . 109.5
C14C C15C H15I . . 109.5
H15G C15C H15I . . 109.5
H15H C15C H15I . . 109.5
N2A C16A C17A . . 115.1(3)
N2A C16A H16A . . 108.5
C17A C16A H16A . . 108.5
N2A C16A H16B . . 108.5
C17A C16A H16B . . 108.5
H16A C16A H16B . . 107.5
C16A C17A H17A . . 109.5
C16A C17A H17B . . 109.5
H17A C17A H17B . . 109.5
C16A C17A H17C . . 109.5
H17A C17A H17C . . 109.5
H17B C17A H17C . . 109.5
C5A C18A C19A . . 131.6(3)
C5A C18A H18A . . 114.2
C19A C18A H18A . . 114.2
C24A C19A C20A . . 116.0(2)
C24A C19A C18A . . 118.0(2)
C20A C19A C18A . . 126.0(2)
C21A C20A C19A . . 121.9(3)
C21A C20A H20A . . 119.1
C19A C20A H20A . . 119.1
C20A C21A C22A . . 121.7(2)
C20A C21A H21A . . 119.2
C22A C21A H21A . . 119.2
N3A C22A C21A . . 122.5(2)
N3A C22A C23A . . 120.8(2)
C21A C22A C23A . . 116.6(2)
C24A C23A C22A . . 120.8(2)
C24A C23A H23A . . 119.6
C22A C23A H23A . . 119.6
C23A C24A C19A . . 123.0(2)
C23A C24A H24A . . 118.5
C19A C24A H24A . . 118.5
N3A C25A C26A . . 113.3(2)
N3A C25A H25A . . 108.9
C26A C25A H25A . . 108.9
N3A C25A H25B . . 108.9
C26A C25A H25B . . 108.9
H25A C25A H25B . . 107.7
C25A C26A H26A . . 109.5
C25A C26A H26B . . 109.5
H26A C26A H26B . . 109.5
C25A C26A H26C . . 109.5
H26A C26A H26C . . 109.5
H26B C26A H26C . . 109.5
N3A C27A C28A . . 113.7(2)
N3A C27A H27A . . 108.8
C28A C27A H27A . . 108.8
N3A C27A H27B . . 108.8
C28A C27A H27B . . 108.8
H27A C27A H27B . . 107.7
C27A C28A H28A . . 109.5
C27A C28A H28B . . 109.5
H28A C28A H28B . . 109.5
C27A C28A H28C . . 109.5
H28A C28A H28C . . 109.5
H28B C28A H28C . . 109.5
O3A C29A O2A . . 123.1(2)
O3A C29A C30A . . 121.6(2)
O2A C29A C30A . . 115.3(2)
C29A C30A C30A . 2_666 114.4(3)
C29A C30A H30A . . 108.7
C30A C30A H30A 2_666 . 108.7
C29A C30A H30B . . 108.7
C30A C30A H30B 2_666 . 108.7
H30A C30A H30B . . 107.6
C2B N1B C6B . . 111.6(2)
C2B N1B H1C . . 108.3
C6B N1B H1C . . 109.1
C2B N1B H1D . . 112.4
C6B N1B H1D . . 110.9
H1C N1B H1D . . 104.2
C11B N2B C16B . . 122.0(2)
C11B N2B C14B . . 121.4(2)
C16B N2B C14B . . 115.3(2)
C22B N3B C25B . . 120.8(2)
C22B N3B C27B . . 121.3(2)
C25B N3B C27B . . 117.9(2)
N1B C2B C3B . . 112.0(2)
N1B C2B H2C . . 109.2
C3B C2B H2C . . 109.2
N1B C2B H2D . . 109.2
C3B C2B H2D . . 109.2
H2C C2B H2D . . 107.9
C7B C3B C4B . . 117.5(2)
C7B C3B C2B . . 124.4(2)
C4B C3B C2B . . 118.0(2)
O1B C4B C5B . . 121.8(2)
O1B C4B C3B . . 119.7(2)
C5B C4B C3B . . 118.4(2)
C18B C5B C4B . . 116.8(2)
C18B C5B C6B . . 125.1(2)
C4B C5B C6B . . 118.1(2)
N1B C6B C5B . . 111.4(2)
N1B C6B H6C . . 109.4
C5B C6B H6C . . 109.4
N1B C6B H6D . . 109.4
C5B C6B H6D . . 109.4
H6C C6B H6D . . 108.0
C3B C7B C8B . . 131.5(2)
C3B C7B H7B . . 114.2
C8B C7B H7B . . 114.2
C13B C8B C9B . . 116.0(2)
C13B C8B C7B . . 118.0(2)
C9B C8B C7B . . 126.0(2)
C10B C9B C8B . . 121.6(2)
C10B C9B H9B . . 119.2
C8B C9B H9B . . 119.2
C9B C10B C11B . . 122.2(3)
C9B C10B H10B . . 118.9
C11B C10B H10B . . 118.9
N2B C11B C12B . . 122.3(2)
N2B C11B C10B . . 121.6(3)
C12B C11B C10B . . 116.1(2)
C13B C12B C11B . . 120.8(2)
C13B C12B H12B . . 119.6
C11B C12B H12B . . 119.6
C12B C13B C8B . . 123.1(3)
C12B C13B H13B . . 118.5
C8B C13B H13B . . 118.5
N2B C14B C15B . . 112.6(3)
N2B C14B H14C . . 109.1
C15B C14B H14C . . 109.1
N2B C14B H14D . . 109.1
C15B C14B H14D . . 109.1
H14C C14B H14D . . 107.8
C14B C15B H15D . . 109.5
C14B C15B H15E . . 109.5
H15D C15B H15E . . 109.5
C14B C15B H15F . . 109.5
H15D C15B H15F . . 109.5
H15E C15B H15F . . 109.5
N2B C16B C17B . . 112.2(3)
N2B C16B H16C . . 109.2
C17B C16B H16C . . 109.2
N2B C16B H16D . . 109.2
C17B C16B H16D . . 109.2
H16C C16B H16D . . 107.9
C16B C17B H17D . . 109.5
C16B C17B H17E . . 109.5
H17D C17B H17E . . 109.5
C16B C17B H17F . . 109.5
H17D C17B H17F . . 109.5
H17E C17B H17F . . 109.5
C5B C18B C19B . . 132.9(2)
C5B C18B H18B . . 113.5
C19B C18B H18B . . 113.5
C24B C19B C20B . . 116.0(2)
C24B C19B C18B . . 116.7(2)
C20B C19B C18B . . 127.2(2)
C21B C20B C19B . . 122.0(2)
C21B C20B H20B . . 119.0
C19B C20B H20B . . 119.0
C20B C21B C22B . . 121.7(2)
C20B C21B H21B . . 119.2
C22B C21B H21B . . 119.2
N3B C22B C21B . . 122.2(2)
N3B C22B C23B . . 121.0(2)
C21B C22B C23B . . 116.7(2)
C24B C23B C22B . . 120.4(2)
C24B C23B H23B . . 119.8
C22B C23B H23B . . 119.8
C23B C24B C19B . . 123.1(2)
C23B C24B H24B . . 118.4
C19B C24B H24B . . 118.4
N3B C25B C26B . . 114.5(2)
N3B C25B H25C . . 108.6
C26B C25B H25C . . 108.6
N3B C25B H25D . . 108.6
C26B C25B H25D . . 108.6
H25C C25B H25D . . 107.6
C25B C26B H26D . . 109.5
C25B C26B H26E . . 109.5
H26D C26B H26E . . 109.5
C25B C26B H26F . . 109.5
H26D C26B H26F . . 109.5
H26E C26B H26F . . 109.5
N3B C27B C28B . . 112.6(2)
N3B C27B H27C . . 109.1
C28B C27B H27C . . 109.1
N3B C27B H27D . . 109.1
C28B C27B H27D . . 109.1
H27C C27B H27D . . 107.8
C27B C28B H28D . . 109.5
C27B C28B H28E . . 109.5
H28D C28B H28E . . 109.5
C27B C28B H28F . . 109.5
H28D C28B H28F . . 109.5
H28E C28B H28F . . 109.5
O3B C29B O2B . . 123.6(2)
O3B C29B C30B . . 122.3(2)
O2B C29B C30B . . 114.1(2)
C30B C30B C29B 2_766 . 113.2(3)
C30B C30B H30C 2_766 . 108.9
C29B C30B H30C . . 108.9
C30B C30B H30D 2_766 . 108.9
C29B C30B H30D . . 108.9
H30C C30B H30D . . 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1A C4A . 1.232(3)
N1A C6A . 1.466(4)
N1A C2A . 1.470(3)
N1A H1A . 0.9030
N1A H1B . 0.9300
N2A C11A . 1.369(4)
N2A C16A . 1.462(4)
N2A C14C . 1.485(3)
N2A C14A . 1.501(3)
N3A C22A . 1.370(3)
N3A C27A . 1.456(3)
N3A C25A . 1.461(3)
C2A C3A . 1.504(4)
C2A H2A . 0.9900
C2A H2B . 0.9900
C3A C7A . 1.351(4)
C3A C4A . 1.487(4)
C4A C5A . 1.482(4)
C5A C18A . 1.352(4)
C5A C6A . 1.501(4)
C6A H6A . 0.9900
C6A H6B . 0.9900
C7A C8A . 1.447(4)
C7A H7A . 0.9500
C8A C13A . 1.395(4)
C8A C9A . 1.403(4)
C9A C10A . 1.374(4)
C9A H9A . 0.9500
C10A C11A . 1.421(4)
C10A H10A . 0.9500
C11A C12A . 1.399(4)
C12A C13A . 1.367(4)
C12A H12A . 0.9500
C13A H13A . 0.9500
C14A C15A . 1.530(3)
C14A H14A . 0.9900
C14A H14B . 0.9900
C15A H15A . 0.9800
C15A H15B . 0.9800
C15A H15C . 0.9800
C14C C15C . 1.536(3)
C14C H14E . 0.9900
C14C H14F . 0.9900
C15C H15G . 0.9800
C15C H15H . 0.9800
C15C H15I . 0.9800
C16A C17A . 1.510(5)
C16A H16A . 0.9900
C16A H16B . 0.9900
C17A H17A . 0.9800
C17A H17B . 0.9800
C17A H17C . 0.9800
C18A C19A . 1.453(4)
C18A H18A . 0.9500
C19A C24A . 1.403(4)
C19A C20A . 1.405(4)
C20A C21A . 1.374(4)
C20A H20A . 0.9500
C21A C22A . 1.407(4)
C21A H21A . 0.9500
C22A C23A . 1.414(4)
C23A C24A . 1.367(4)
C23A H23A . 0.9500
C24A H24A . 0.9500
C25A C26A . 1.516(4)
C25A H25A . 0.9900
C25A H25B . 0.9900
C26A H26A . 0.9800
C26A H26B . 0.9800
C26A H26C . 0.9800
C27A C28A . 1.513(4)
C27A H27A . 0.9900
C27A H27B . 0.9900
C28A H28A . 0.9800
C28A H28B . 0.9800
C28A H28C . 0.9800
O2A C29A . 1.281(3)
O3A C29A . 1.226(3)
C29A C30A . 1.505(4)
C30A C30A 2_666 1.508(5)
C30A H30A . 0.9900
C30A H30B . 0.9900
O1B C4B . 1.230(3)
N1B C2B . 1.466(3)
N1B C6B . 1.473(3)
N1B H1C . 0.9010
N1B H1D . 0.9361
N2B C11B . 1.364(4)
N2B C16B . 1.457(4)
N2B C14B . 1.461(4)
N3B C22B . 1.373(3)
N3B C25B . 1.468(3)
N3B C27B . 1.469(3)
C2B C3B . 1.508(4)
C2B H2C . 0.9900
C2B H2D . 0.9900
C3B C7B . 1.344(4)
C3B C4B . 1.488(4)
C4B C5B . 1.487(3)
C5B C18B . 1.350(4)
C5B C6B . 1.509(3)
C6B H6C . 0.9900
C6B H6D . 0.9900
C7B C8B . 1.449(4)
C7B H7B . 0.9500
C8B C13B . 1.404(4)
C8B C9B . 1.407(4)
C9B C10B . 1.362(4)
C9B H9B . 0.9500
C10B C11B . 1.418(4)
C10B H10B . 0.9500
C11B C12B . 1.411(4)
C12B C13B . 1.365(4)
C12B H12B . 0.9500
C13B H13B . 0.9500
C14B C15B . 1.515(5)
C14B H14C . 0.9900
C14B H14D . 0.9900
C15B H15D . 0.9800
C15B H15E . 0.9800
C15B H15F . 0.9800
C16B C17B . 1.519(4)
C16B H16C . 0.9900
C16B H16D . 0.9900
C17B H17D . 0.9800
C17B H17E . 0.9800
C17B H17F . 0.9800
C18B C19B . 1.451(3)
C18B H18B . 0.9500
C19B C24B . 1.404(4)
C19B C20B . 1.407(3)
C20B C21B . 1.377(4)
C20B H20B . 0.9500
C21B C22B . 1.413(4)
C21B H21B . 0.9500
C22B C23B . 1.416(4)
C23B C24B . 1.380(4)
C23B H23B . 0.9500
C24B H24B . 0.9500
C25B C26B . 1.513(4)
C25B H25C . 0.9900
C25B H25D . 0.9900
C26B H26D . 0.9800
C26B H26E . 0.9800
C26B H26F . 0.9800
C27B C28B . 1.508(4)
C27B H27C . 0.9900
C27B H27D . 0.9900
C28B H28D . 0.9800
C28B H28E . 0.9800
C28B H28F . 0.9800
O2B C29B . 1.304(3)
O3B C29B . 1.214(3)
C29B C30B . 1.521(4)
C30B C30B 2_766 1.510(5)
C30B H30C . 0.9900
C30B H30D . 0.9900
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
N1A H1B O2A . 0.93 1.61 2.538(3) 173 yes
N1B H1C O3A 2_666 0.90 1.97 2.833(3) 161 yes
N1B H1D O2B . 0.94 1.63 2.561(3) 174 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_4
_geom_torsion
C6A N1A C2A C3A . -54.7(3)
N1A C2A C3A C7A . -148.4(3)
N1A C2A C3A C4A . 29.1(3)
C7A C3A C4A O1A . -8.5(4)
C2A C3A C4A O1A . 173.8(2)
C7A C3A C4A C5A . 170.4(2)
C2A C3A C4A C5A . -7.3(4)
O1A C4A C5A C18A . 12.0(4)
C3A C4A C5A C18A . -166.8(2)
O1A C4A C5A C6A . -171.2(3)
C3A C4A C5A C6A . 9.9(4)
C2A N1A C6A C5A . 57.4(3)
C18A C5A C6A N1A . 142.1(3)
C4A C5A C6A N1A . -34.3(3)
C4A C3A C7A C8A . 178.5(3)
C2A C3A C7A C8A . -3.9(5)
C3A C7A C8A C13A . 156.3(3)
C3A C7A C8A C9A . -27.0(5)
C13A C8A C9A C10A . -2.2(5)
C7A C8A C9A C10A . -179.0(3)
C8A C9A C10A C11A . 0.2(6)
C16A N2A C11A C12A . 5.1(6)
C14C N2A C11A C12A . 145.5(4)
C14A N2A C11A C12A . -166.9(3)
C16A N2A C11A C10A . -176.3(4)
C14C N2A C11A C10A . -35.9(6)
C14A N2A C11A C10A . 11.7(6)
C9A C10A C11A N2A . -177.3(4)
C9A C10A C11A C12A . 1.4(5)
N2A C11A C12A C13A . 177.9(3)
C10A C11A C12A C13A . -0.8(5)
C11A C12A C13A C8A . -1.3(4)
C9A C8A C13A C12A . 2.8(4)
C7A C8A C13A C12A . 179.9(3)
C11A N2A C14A C15A . -93.6(5)
C16A N2A C14A C15A . 94.1(5)
C14C N2A C14A C15A . -0.7(5)
C11A N2A C14C C15C . 104.9(6)
C16A N2A C14C C15C . -111.1(6)
C14A N2A C14C C15C . -6.1(5)
C11A N2A C16A C17A . 78.5(4)
C14C N2A C16A C17A . -62.9(4)
C14A N2A C16A C17A . -109.1(4)
C4A C5A C18A C19A . -179.8(3)
C6A C5A C18A C19A . 3.7(5)
C5A C18A C19A C24A . -159.5(3)
C5A C18A C19A C20A . 24.1(5)
C24A C19A C20A C21A . 0.5(4)
C18A C19A C20A C21A . 177.0(3)
C19A C20A C21A C22A . 0.4(4)
C27A N3A C22A C21A . -169.4(2)
C25A N3A C22A C21A . 4.4(4)
C27A N3A C22A C23A . 13.7(4)
C25A N3A C22A C23A . -172.5(2)
C20A C21A C22A N3A . -177.4(3)
C20A C21A C22A C23A . -0.4(4)
N3A C22A C23A C24A . 176.6(2)
C21A C22A C23A C24A . -0.5(4)
C22A C23A C24A C19A . 1.4(4)
C20A C19A C24A C23A . -1.4(4)
C18A C19A C24A C23A . -178.2(2)
C22A N3A C25A C26A . -85.9(3)
C27A N3A C25A C26A . 88.3(3)
C22A N3A C27A C28A . -91.8(3)
C25A N3A C27A C28A . 94.0(3)
O3A C29A C30A C30A 2_666 10.3(5)
O2A C29A C30A C30A 2_666 -172.2(3)
C6B N1B C2B C3B . -59.1(3)
N1B C2B C3B C7B . -152.7(2)
N1B C2B C3B C4B . 22.9(3)
C7B C3B C4B O1B . 6.0(4)
C2B C3B C4B O1B . -169.9(3)
C7B C3B C4B C5B . -173.6(2)
C2B C3B C4B C5B . 10.5(4)
O1B C4B C5B C18B . -9.9(4)
C3B C4B C5B C18B . 169.7(2)
O1B C4B C5B C6B . 171.2(3)
C3B C4B C5B C6B . -9.2(4)
C2B N1B C6B C5B . 60.1(3)
C18B C5B C6B N1B . 156.1(3)
C4B C5B C6B N1B . -25.1(3)
C4B C3B C7B C8B . -173.8(3)
C2B C3B C7B C8B . 1.8(5)
C3B C7B C8B C13B . 156.7(3)
C3B C7B C8B C9B . -21.3(5)
C13B C8B C9B C10B . -3.2(4)
C7B C8B C9B C10B . 174.9(3)
C8B C9B C10B C11B . -1.8(4)
C16B N2B C11B C12B . 2.5(4)
C14B N2B C11B C12B . 169.5(3)
C16B N2B C11B C10B . -178.0(3)
C14B N2B C11B C10B . -11.1(4)
C9B C10B C11B N2B . -174.3(3)
C9B C10B C11B C12B . 5.2(4)
N2B C11B C12B C13B . 175.9(3)
C10B C11B C12B C13B . -3.6(4)
C11B C12B C13B C8B . -1.3(4)
C9B C8B C13B C12B . 4.7(4)
C7B C8B C13B C12B . -173.5(3)
C11B N2B C14B C15B . 88.1(3)
C16B N2B C14B C15B . -104.1(3)
C11B N2B C16B C17B . 82.7(4)
C14B N2B C16B C17B . -85.0(3)
C4B C5B C18B C19B . -173.2(3)
C6B C5B C18B C19B . 5.6(5)
C5B C18B C19B C24B . 177.8(3)
C5B C18B C19B C20B . 2.0(5)
C24B C19B C20B C21B . 0.3(4)
C18B C19B C20B C21B . 176.1(3)
C19B C20B C21B C22B . -2.9(4)
C25B N3B C22B C21B . -3.6(4)
C27B N3B C22B C21B . 177.9(3)
C25B N3B C22B C23B . 179.5(3)
C27B N3B C22B C23B . 0.9(4)
C20B C21B C22B N3B . -173.5(3)
C20B C21B C22B C23B . 3.6(4)
N3B C22B C23B C24B . 175.3(3)
C21B C22B C23B C24B . -1.8(4)
C22B C23B C24B C19B . -0.8(4)
C20B C19B C24B C23B . 1.5(4)
C18B C19B C24B C23B . -174.7(3)
C22B N3B C25B C26B . -80.6(3)
C27B N3B C25B C26B . 97.9(3)
C22B N3B C27B C28B . 81.2(3)
C25B N3B C27B C28B . -97.4(3)
O3B C29B C30B C30B 2_766 4.1(4)
O2B C29B C30B C30B 2_766 -177.3(3)
