#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229010.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_2229010
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Siddegowda, M. S.'
'Yathirajan, H. S.'
'Chidan Kumar, C. S.'
_publ_section_title
;
 Cinnarizinium dipicrate
;
_journal_coeditor_code           CV5030
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o500
_journal_page_last               o501
_journal_paper_doi               10.1107/S1600536811002674
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H30 N2 2+, 2C6 H2 N3 O7 -'
_chemical_formula_moiety         'C26 H30 N2 2+, 2(C6 H2 N3 O7 -)'
_chemical_formula_sum            'C38 H34 N8 O14'
_chemical_formula_weight         826.73
_chemical_name_common
;
Cinnarizinium dipicrate
;
_chemical_name_systematic
;
1-diphenylmethyl-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine-1,4-diium
bis(2,4,6-trinitrophenolate)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9170(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1987(2)
_cell_length_b                   10.09130(17)
_cell_length_c                   25.0724(3)
_cell_measurement_reflns_used    7661
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      73.2943
_cell_measurement_theta_min      4.8203
_cell_volume                     3824.98(9)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_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      295(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14786
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.45
_diffrn_reflns_theta_min         4.82
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.27
_refine_diff_density_max         1.238
_refine_diff_density_min         -0.483
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         7319
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0924
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1960P)²+2.2706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2707
_refine_ls_wR_factor_ref         0.2891
_reflns_number_gt                5784
_reflns_number_total             7319
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5030.cif
_cod_data_source_block           I
_cod_original_cell_volume        3824.98(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229010
_cod_database_fobs_code          2229010
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
N N1 0.75982(13) 0.8086(2) 0.55675(7) 0.0344(5) Uani d D 1 A .
H H1N 0.759(2) 0.816(3) 0.5925(3) 0.044(8) Uiso d D 1 . .
N N2 0.75781(15) 0.5191(2) 0.55806(8) 0.0413(5) Uani d D 1 . .
H H2N 0.766(3) 0.501(4) 0.5239(5) 0.062(10) Uiso d D 1 . .
C C1 0.84038(16) 0.7281(3) 0.54794(11) 0.0408(6) Uani d . 1 . .
H H1A 0.8932 0.7766 0.5613 0.049 Uiso calc R 1 A .
H H1B 0.8422 0.7134 0.5098 0.049 Uiso calc R 1 . .
C C2 0.83881(18) 0.5960(3) 0.57647(11) 0.0433(6) Uani d . 1 A .
H H2A 0.8907 0.5451 0.5697 0.052 Uiso calc R 1 . .
H H2B 0.8410 0.6109 0.6148 0.052 Uiso calc R 1 . .
C C3 0.67708(17) 0.5985(3) 0.56498(11) 0.0431(6) Uani d . 1 A .
H H3A 0.6732 0.6136 0.6029 0.052 Uiso calc R 1 . .
H H3B 0.6250 0.5492 0.5508 0.052 Uiso calc R 1 . .
C C4 0.67904(16) 0.7304(3) 0.53629(10) 0.0403(6) Uani d . 1 . .
H H4A 0.6792 0.7154 0.4981 0.048 Uiso calc R 1 A .
H H4B 0.6263 0.7806 0.5419 0.048 Uiso calc R 1 . .
C C5 0.76219(17) 0.9422(3) 0.52874(9) 0.0384(6) Uani d . 1 . .
H H5A 0.7662 0.9246 0.4906 0.046 Uiso calc R 1 A .
C C6 0.67862(17) 1.0214(3) 0.53265(10) 0.0394(6) Uani d . 1 A .
C C7 0.6353(2) 1.0759(3) 0.48662(12) 0.0526(7) Uani d . 1 . .
H H7A 0.6541 1.0553 0.4535 0.063 Uiso calc R 1 A .
C C8 0.5645(2) 1.1607(4) 0.48926(15) 0.0671(9) Uani d . 1 A .
H H8A 0.5364 1.1973 0.4580 0.080 Uiso calc R 1 . .
C C9 0.5356(2) 1.1908(4) 0.53768(15) 0.0618(9) Uani d . 1 . .
H H9A 0.4888 1.2494 0.5395 0.074 Uiso calc R 1 A .
C C10 0.5762(2) 1.1342(4) 0.58369(14) 0.0582(8) Uani d . 1 A .
H H10A 0.5551 1.1519 0.6165 0.070 Uiso calc R 1 . .
C C11 0.6478(2) 1.0515(3) 0.58150(11) 0.0497(7) Uani d . 1 . .
H H11A 0.6757 1.0154 0.6129 0.060 Uiso calc R 1 A .
C C12 0.84287(18) 1.0223(3) 0.54911(11) 0.0425(6) Uani d . 1 A .
C C13 0.8878(2) 1.0922(4) 0.51268(15) 0.0679(10) Uani d . 1 . .
H H13A 0.8719 1.0812 0.4761 0.081 Uiso calc R 1 A .
C C14 0.9559(3) 1.1782(5) 0.5300(2) 0.0871(14) Uani d . 1 A .
H H14A 0.9843 1.2259 0.5051 0.105 Uiso calc R 1 . .
C C15 0.9817(2) 1.1931(5) 0.5837(2) 0.0811(13) Uani d . 1 . .
H H15A 1.0276 1.2504 0.5952 0.097 Uiso calc R 1 A .
C C16 0.9390(2) 1.1228(4) 0.62025(16) 0.0675(9) Uani d . 1 A .
H H16A 0.9571 1.1314 0.6567 0.081 Uiso calc R 1 . .
C C17 0.8696(2) 1.0395(3) 0.60355(12) 0.0524(7) Uani d . 1 . .
H H17A 0.8403 0.9944 0.6288 0.063 Uiso calc R 1 A .
C C18A 0.7558(2) 0.3854(3) 0.58610(13) 0.0561(8) Uani d P 0.586(4) A 1
H H18A 0.8131 0.3431 0.5858 0.067 Uiso calc PR 0.586(4) A 1
H H18B 0.7122 0.3292 0.5662 0.067 Uiso calc PR 0.586(4) A 1
C C19A 0.7334(4) 0.3969(6) 0.6447(3) 0.0529(11) Uani d P 0.586(4) A 1
H H19A 0.6748 0.4071 0.6515 0.063 Uiso calc PR 0.586(4) A 1
C C20A 0.7955(4) 0.3926(5) 0.6849(2) 0.0520(10) Uani d PD 0.586(4) A 1
H H20A 0.8529 0.3849 0.6755 0.062 Uiso calc PR 0.586(4) A 1
C C21A 0.7875(8) 0.3981(12) 0.7433(4) 0.053(3) Uani d PD 0.586(4) A 1
C C22A 0.8612(7) 0.3990(12) 0.7805(5) 0.058(2) Uani d P 0.586(4) A 1
H H22A 0.9177 0.4000 0.7693 0.070 Uiso calc PR 0.586(4) A 1
C C23A 0.8507(14) 0.398(2) 0.8307(10) 0.066(5) Uani d P 0.586(4) A 1
H H23A 0.9011 0.3996 0.8551 0.079 Uiso calc PR 0.586(4) A 1
C C24A 0.7726(14) 0.3958(14) 0.8500(8) 0.068(7) Uani d P 0.586(4) A 1
H H24A 0.7739 0.3856 0.8869 0.082 Uiso calc PR 0.586(4) A 1
C C25A 0.691(2) 0.406(3) 0.8224(14) 0.079(8) Uani d P 0.586(4) A 1
H H25A 0.6372 0.4152 0.8369 0.094 Uiso calc PR 0.586(4) A 1
C C26A 0.7035(14) 0.401(3) 0.7669(14) 0.072(5) Uani d P 0.586(4) A 1
H H26A 0.6525 0.3995 0.7430 0.086 Uiso calc PR 0.586(4) A 1
C C18B 0.7558(2) 0.3854(3) 0.58610(13) 0.0561(8) Uani d P 0.414(4) A 2
H H18C 0.6960 0.3507 0.5815 0.067 Uiso calc PR 0.414(4) A 2
H H18D 0.7936 0.3238 0.5693 0.067 Uiso calc PR 0.414(4) A 2
C C19B 0.7860(6) 0.3939(8) 0.6445(4) 0.0529(11) Uani d P 0.414(4) A 2
H H19B 0.8460 0.3997 0.6561 0.063 Uiso calc PR 0.414(4) A 2
C C20B 0.7274(6) 0.3932(8) 0.6793(3) 0.0520(10) Uani d PD 0.414(4) A 2
H H20B 0.6679 0.3888 0.6663 0.062 Uiso calc PR 0.414(4) A 2
C C21B 0.7502(10) 0.3992(16) 0.7386(4) 0.044(3) Uani d PD 0.414(4) A 2
C C22B 0.8333(9) 0.3969(16) 0.7670(6) 0.051(3) Uani d P 0.414(4) A 2
H H22B 0.8837 0.3942 0.7489 0.061 Uiso calc PR 0.414(4) A 2
C C23B 0.841(3) 0.399(3) 0.826(2) 0.104(14) Uani d P 0.414(4) A 2
H H23B 0.8975 0.3976 0.8442 0.125 Uiso calc PR 0.414(4) A 2
C C24B 0.771(2) 0.402(2) 0.8544(11) 0.071(10) Uani d P 0.414(4) A 2
H H24B 0.7724 0.4088 0.8915 0.085 Uiso calc PR 0.414(4) A 2
C C25B 0.694(3) 0.395(3) 0.8183(13) 0.050(5) Uani d P 0.414(4) A 2
H H25B 0.6429 0.3848 0.8351 0.060 Uiso calc PR 0.414(4) A 2
C C26B 0.6787(18) 0.400(3) 0.7629(13) 0.052(4) Uani d P 0.414(4) A 2
H H26B 0.6222 0.4029 0.7447 0.062 Uiso calc PR 0.414(4) A 2
O O1A 0.7492(2) 0.7961(3) 0.66177(8) 0.0704(7) Uani d . 1 B .
O O2AA 0.5803(8) 0.7737(14) 0.64870(13) 0.108(3) Uani d PD 0.68(2) B 1
O O3AA 0.5075(5) 0.803(2) 0.7157(4) 0.169(5) Uani d PD 0.68(2) B 1
O O2AB 0.5627(18) 0.742(3) 0.6507(4) 0.108(3) Uani d PD 0.32(2) B 2
O O3AB 0.5305(13) 0.863(2) 0.7152(11) 0.169(5) Uani d PD 0.32(2) B 2
O O4A 0.64470(17) 0.7000(3) 0.89225(10) 0.0867(9) Uani d D 1 . .
O O5A 0.78481(17) 0.7067(3) 0.90778(9) 0.0809(9) Uani d D 1 . .
O O6AA 0.9618(2) 0.7918(10) 0.76971(16) 0.134(3) Uani d PD 0.851(14) C 1
O O7AA 0.9173(3) 0.7450(11) 0.68875(15) 0.143(3) Uani d PD 0.851(14) C 1
O O6AB 0.9535(15) 0.851(2) 0.7519(13) 0.134(3) Uani d PD 0.149(14) C 2
O O7AB 0.924(2) 0.680(4) 0.7036(18) 0.143(3) Uani d PD 0.149(14) C 2
N N1A 0.57602(18) 0.7801(4) 0.69661(10) 0.0703(8) Uani d D 1 . .
N N2A 0.71761(14) 0.7114(3) 0.87725(8) 0.0593(7) Uani d D 1 . .
N N3A 0.90351(17) 0.7638(4) 0.73487(10) 0.0758(9) Uani d D 1 . .
C C1A 0.7410(2) 0.7722(3) 0.70954(10) 0.0431(6) Uani d . 1 . .
C C2A 0.6581(2) 0.7630(3) 0.73172(11) 0.0462(6) Uani d . 1 B .
C C3A 0.6493(2) 0.7436(3) 0.78570(12) 0.0493(7) Uani d . 1 . .
H H3AA 0.5936 0.7396 0.7979 0.059 Uiso calc R 1 B .
C C4A 0.7242(2) 0.7305(3) 0.82064(10) 0.0453(6) Uani d . 1 B .
C C5A 0.8072(2) 0.7370(3) 0.80328(11) 0.0478(7) Uani d . 1 . .
H H5AA 0.8574 0.7286 0.8276 0.057 Uiso calc R 1 B .
C C6A 0.8152(2) 0.7560(3) 0.74985(11) 0.0474(7) Uani d . 1 B .
O O1B 0.7062(2) 0.4822(4) 0.45690(11) 0.0924(10) Uani d . 1 D .
O O2BA 0.5305(6) 0.4599(7) 0.4261(2) 0.1086(19) Uani d PD 0.80(2) D 1
O O3BA 0.5020(6) 0.5403(14) 0.3479(3) 0.126(2) Uani d PD 0.80(2) D 1
O O2BB 0.5629(15) 0.483(4) 0.43148(19) 0.1086(19) Uani d PD 0.20(2) D 2
O O3BB 0.493(3) 0.556(6) 0.3597(9) 0.126(2) Uani d PD 0.20(2) D 2
O O4BA 0.6720(3) 0.4105(6) 0.21067(13) 0.149(3) Uani d PD 0.950(19) E 1
O O5BA 0.8123(3) 0.4153(7) 0.22437(14) 0.136(3) Uani d PD 0.950(19) E 1
O O4BB 0.6771(15) 0.376(6) 0.2114(4) 0.149(3) Uani d PD 0.050(19) E 2
O O5BB 0.803(2) 0.470(5) 0.2232(5) 0.136(3) Uani d PD 0.050(19) E 2
O O6BA 0.9445(3) 0.3776(7) 0.4123(2) 0.114(2) Uani d PD 0.756(8) F 1
O O7BA 0.8773(4) 0.4852(11) 0.4686(2) 0.120(2) Uani d PD 0.756(8) F 1
O O6BB 0.9310(8) 0.461(2) 0.3901(5) 0.114(2) Uani d PD 0.244(8) F 2
O O7BB 0.8972(14) 0.478(4) 0.4700(5) 0.120(2) Uani d PD 0.244(8) F 2
N N1B 0.5528(2) 0.4924(4) 0.38306(12) 0.0794(9) Uani d D 1 . .
N N2B 0.7398(3) 0.4172(3) 0.24045(11) 0.1022(17) Uani d D 1 . .
N N3B 0.8814(2) 0.4406(4) 0.42404(12) 0.0837(10) Uani d D 1 . .
C C1B 0.7204(3) 0.4642(3) 0.40885(12) 0.0632(9) Uani d . 1 . .
C C2B 0.6469(3) 0.4639(3) 0.36980(15) 0.0606(8) Uani d D 1 D .
C C3B 0.6514(3) 0.4471(3) 0.31648(14) 0.0619(9) Uani d . 1 . .
H H3BA 0.5999 0.4472 0.2930 0.074 Uiso calc R 1 D .
C C4B 0.7305(3) 0.4302(3) 0.29740(11) 0.0612(9) Uani d D 1 D .
C C5B 0.8079(3) 0.4290(3) 0.33118(17) 0.0669(10) Uani d . 1 . .
H H5BA 0.8623 0.4172 0.3179 0.080 Uiso calc R 1 D .
C C6B 0.8022(3) 0.4458(3) 0.38576(16) 0.0669(10) Uani d . 1 D .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C4 N1 C1 . . 108.3(2) ?
C4 N1 C5 . . 111.38(19) ?
C1 N1 C5 . . 110.63(19) ?
C4 N1 H1N . . 107(2) ?
C1 N1 H1N . . 107(2) ?
C5 N1 H1N . . 113(2) ?
C2 N2 C3 . . 110.4(2) ?
C2 N2 C18A . . 112.0(2) ?
C3 N2 C18A . . 111.5(2) ?
C2 N2 H2N . . 103(3) ?
C3 N2 H2N . . 114(3) ?
C18A N2 H2N . . 106(3) ?
N1 C1 C2 . . 110.7(2) ?
N1 C1 H1A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.1 ?
N2 C2 C1 . . 111.4(2) ?
N2 C2 H2A . . 109.3 ?
C1 C2 H2A . . 109.3 ?
N2 C2 H2B . . 109.3 ?
C1 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108.0 ?
N2 C3 C4 . . 111.1(2) ?
N2 C3 H3A . . 109.4 ?
C4 C3 H3A . . 109.4 ?
N2 C3 H3B . . 109.4 ?
C4 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
N1 C4 C3 . . 110.8(2) ?
N1 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
C6 C5 C12 . . 110.6(2) ?
C6 C5 N1 . . 112.2(2) ?
C12 C5 N1 . . 112.0(2) ?
C6 C5 H5A . . 107.2 ?
C12 C5 H5A . . 107.2 ?
N1 C5 H5A . . 107.2 ?
C7 C6 C11 . . 118.3(3) ?
C7 C6 C5 . . 119.1(2) ?
C11 C6 C5 . . 122.3(2) ?
C8 C7 C6 . . 120.8(3) ?
C8 C7 H7A . . 119.6 ?
C6 C7 H7A . . 119.6 ?
C9 C8 C7 . . 120.2(3) ?
C9 C8 H8A . . 119.9 ?
C7 C8 H8A . . 119.9 ?
C8 C9 C10 . . 119.7(3) ?
C8 C9 H9A . . 120.1 ?
C10 C9 H9A . . 120.1 ?
C9 C10 C11 . . 120.4(3) ?
C9 C10 H10A . . 119.8 ?
C11 C10 H10A . . 119.8 ?
C10 C11 C6 . . 120.5(3) ?
C10 C11 H11A . . 119.8 ?
C6 C11 H11A . . 119.8 ?
C13 C12 C17 . . 117.9(3) ?
C13 C12 C5 . . 119.1(3) ?
C17 C12 C5 . . 122.8(2) ?
C14 C13 C12 . . 120.9(4) ?
C14 C13 H13A . . 119.5 ?
C12 C13 H13A . . 119.5 ?
C15 C14 C13 . . 120.3(3) ?
C15 C14 H14A . . 119.8 ?
C13 C14 H14A . . 119.8 ?
C14 C15 C16 . . 119.5(4) ?
C14 C15 H15A . . 120.2 ?
C16 C15 H15A . . 120.2 ?
C15 C16 C17 . . 120.7(4) ?
C15 C16 H16A . . 119.6 ?
C17 C16 H16A . . 119.6 ?
C16 C17 C12 . . 120.6(3) ?
C16 C17 H17A . . 119.7 ?
C12 C17 H17A . . 119.7 ?
N2 C18A C19A . . 112.8(3) ?
N2 C18A H18A . . 109.0 ?
C19A C18A H18A . . 109.0 ?
N2 C18A H18B . . 109.0 ?
C19A C18A H18B . . 109.0 ?
H18A C18A H18B . . 107.8 ?
C20A C19A C18A . . 121.1(5) ?
C20A C19A H19A . . 119.4 ?
C18A C19A H19A . . 119.4 ?
C19A C20A C21A . . 129.3(7) ?
C19A C20A H20A . . 115.4 ?
C21A C20A H20A . . 115.4 ?
C22A C21A C26A . . 114.1(13) ?
C22A C21A C20A . . 121.5(10) ?
C26A C21A C20A . . 124.4(14) ?
C23A C22A C21A . . 119.1(14) ?
C23A C22A H22A . . 120.4 ?
C21A C22A H22A . . 120.4 ?
C22A C23A C24A . . 124(2) ?
C22A C23A H23A . . 117.9 ?
C24A C23A H23A . . 117.9 ?
C23A C24A C25A . . 128(2) ?
C23A C24A H24A . . 115.9 ?
C25A C24A H24A . . 115.9 ?
C24A C25A C26A . . 106(2) ?
C24A C25A H25A . . 126.8 ?
C26A C25A H25A . . 126.8 ?
C25A C26A C21A . . 127.5(18) ?
C25A C26A H26A . . 116.3 ?
C21A C26A H26A . . 116.3 ?
C20B C19B H19B . . 120.2 ?
C19B C20B C21B . . 124.0(9) ?
C19B C20B H20B . . 118.0 ?
C21B C20B H20B . . 118.0 ?
C26B C21B C22B . . 121.5(13) ?
C26B C21B C20B . . 110.3(13) ?
C22B C21B C20B . . 128.1(12) ?
C21B C22B C23B . . 120(2) ?
C21B C22B H22B . . 120.2 ?
C23B C22B H22B . . 120.3 ?
C24B C23B C22B . . 123(4) ?
C24B C23B H23B . . 118.5 ?
C22B C23B H23B . . 118.5 ?
C23B C24B C25B . . 108(3) ?
C23B C24B H24B . . 126.1 ?
C25B C24B H24B . . 126.1 ?
C26B C25B C24B . . 134(3) ?
C26B C25B H25B . . 113.1 ?
C24B C25B H25B . . 113.1 ?
C21B C26B C25B . . 114(2) ?
C21B C26B H26B . . 123.1 ?
C25B C26B H26B . . 123.1 ?
O2AB N1A O3AB . . 122.6(2) ?
O2AA N1A O3AB . . 120.6(19) ?
O2AB N1A O3AA . . 111.7(16) ?
O2AA N1A O3AA . . 122.6(2) ?
O2AB N1A C2A . . 125.8(12) ?
O2AA N1A C2A . . 117.5(5) ?
O3AB N1A C2A . . 109.6(10) ?
O3AA N1A C2A . . 119.9(5) ?
O4A N2A O5A . . 122.6(2) ?
O4A N2A C4A . . 118.4(2) ?
O5A N2A C4A . . 119.0(2) ?
O7AA N3A O6AB . . 106.6(14) ?
O7AB N3A O6AB . . 122.6(2) ?
O7AA N3A O6AA . . 122.6(2) ?
O7AB N3A O6AA . . 114(2) ?
O7AA N3A C6A . . 120.1(3) ?
O7AB N3A C6A . . 116.2(13) ?
O6AB N3A C6A . . 121.2(13) ?
O6AA N3A C6A . . 117.4(3) ?
O1A C1A C2A . . 124.6(3) ?
O1A C1A C6A . . 123.3(3) ?
C2A C1A C6A . . 112.1(2) ?
C3A C2A C1A . . 124.4(3) ?
C3A C2A N1A . . 116.3(3) ?
C1A C2A N1A . . 119.3(2) ?
C4A C3A C2A . . 118.7(3) ?
C4A C3A H3AA . . 120.7 ?
C2A C3A H3AA . . 120.7 ?
C3A C4A C5A . . 121.4(2) ?
C3A C4A N2A . . 120.2(3) ?
C5A C4A N2A . . 118.4(3) ?
C6A C5A C4A . . 119.4(3) ?
C6A C5A H5AA . . 120.3 ?
C4A C5A H5AA . . 120.3 ?
C5A C6A N3A . . 116.3(3) ?
C5A C6A C1A . . 124.0(3) ?
N3A C6A C1A . . 119.7(2) ?
O2BA N1B O3BA . . 122.8(2) ?
O2BA N1B O3BB . . 108.0(17) ?
O3BA N1B O2BB . . 140.1(12) ?
O3BB N1B O2BB . . 122.6(2) ?
O2BA N1B C2B . . 119.9(4) ?
O3BA N1B C2B . . 117.2(5) ?
O3BB N1B C2B . . 131.8(18) ?
O2BB N1B C2B . . 100.3(10) ?
O4BA N2B O5BB . . 117.3(15) ?
O4BB N2B O5BB . . 122.6(2) ?
O4BA N2B O5BA . . 122.6(2) ?
O4BB N2B O5BA . . 118.7(11) ?
O4BA N2B C4B . . 116.6(3) ?
O4BB N2B C4B . . 118.0(3) ?
O5BB N2B C4B . . 118.0(3) ?
O5BA N2B C4B . . 120.7(3) ?
O6BB N3B O7BB . . 122.6(3) ?
O6BB N3B O7BA . . 132.8(12) ?
O7BB N3B O6BA . . 107.9(17) ?
O7BA N3B O6BA . . 122.4(2) ?
O6BB N3B C6B . . 93.6(8) ?
O7BB N3B C6B . . 133.1(15) ?
O7BA N3B C6B . . 118.4(3) ?
O6BA N3B C6B . . 118.6(3) ?
O1B C1B C2B . . 117.7(4) ?
O1B C1B C6B . . 130.2(4) ?
C2B C1B C6B . . 112.1(3) ?
C3B C2B C1B . . 124.7(4) ?
C3B C2B N1B . . 112.4(3) ?
C1B C2B N1B . . 122.8(3) ?
C4B C3B C2B . . 120.1(3) ?
C4B C3B H3BA . . 119.9 ?
C2B C3B H3BA . . 119.9 ?
C3B C4B C5B . . 121.2(3) ?
C3B C4B N2B . . 122.6(4) ?
C5B C4B N2B . . 116.1(4) ?
C4B C5B C6B . . 118.0(3) ?
C4B C5B H5BA . . 121.0 ?
C6B C5B H5BA . . 121.0 ?
C5B C6B C1B . . 123.8(3) ?
C5B C6B N3B . . 120.8(4) ?
C1B C6B N3B . . 115.4(3) ?
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
N1 C4 . 1.505(3) ?
N1 C1 . 1.505(3) ?
N1 C5 . 1.522(3) ?
N1 H1N . 0.901(5) ?
N2 C2 . 1.488(4) ?
N2 C3 . 1.490(4) ?
N2 C18A . 1.524(4) ?
N2 H2N . 0.897(5) ?
C1 C2 . 1.514(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.515(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.513(4) ?
C5 C12 . 1.513(4) ?
C5 H5A . 0.9800 ?
C6 C7 . 1.382(4) ?
C6 C11 . 1.389(4) ?
C7 C8 . 1.381(5) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.367(6) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.375(5) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.378(4) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
C12 C13 . 1.388(4) ?
C12 C17 . 1.394(4) ?
C13 C14 . 1.386(6) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.371(7) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.374(6) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.380(5) ?
C16 H16A . 0.9300 ?
C17 H17A . 0.9300 ?
C18A C19A . 1.546(7) ?
C18A H18A . 0.9700 ?
C18A H18B . 0.9700 ?
C19A C20A . 1.310(9) ?
C19A H19A . 0.9300 ?
C20A C21A . 1.483(8) ?
C20A H20A . 0.9300 ?
C21A C22A . 1.382(12) ?
C21A C26A . 1.46(3) ?
C22A C23A . 1.29(3) ?
C22A H22A . 0.9300 ?
C23A C24A . 1.33(3) ?
C23A H23A . 0.9300 ?
C24A C25A . 1.36(5) ?
C24A H24A . 0.9300 ?
C25A C26A . 1.42(4) ?
C25A H25A . 0.9300 ?
C26A H26A . 0.9300 ?
C19B C20B . 1.309(12) ?
C19B H19B . 0.9300 ?
C20B C21B . 1.493(9) ?
C20B H20B . 0.9300 ?
C21B C26B . 1.30(4) ?
C21B C22B . 1.385(14) ?
C22B C23B . 1.47(5) ?
C22B H22B . 0.9300 ?
C23B C24B . 1.35(5) ?
C23B H23B . 0.9300 ?
C24B C25B . 1.40(6) ?
C24B H24B . 0.9300 ?
C25B C26B . 1.39(4) ?
C25B H25B . 0.9300 ?
C26B H26B . 0.9300 ?
O1A C1A . 1.241(3) ?
O2AA N1A . 1.2115(16) ?
O3AA N1A . 1.2120(17) ?
O2AB N1A . 1.2115(17) ?
O3AB N1A . 1.2118(17) ?
O4A N2A . 1.2118(16) ?
O5A N2A . 1.2125(16) ?
O6AA N3A . 1.2122(16) ?
O7AA N3A . 1.2115(16) ?
O6AB N3A . 1.2117(17) ?
O7AB N3A . 1.2117(17) ?
N1A C2A . 1.461(4) ?
N2A C4A . 1.446(3) ?
N3A C6A . 1.433(4) ?
C1A C2A . 1.432(4) ?
C1A C6A . 1.443(4) ?
C2A C3A . 1.388(4) ?
C3A C4A . 1.370(4) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.377(4) ?
C5A C6A . 1.371(4) ?
C5A H5AA . 0.9300 ?
O1B C1B . 1.259(4) ?
O2BA N1B . 1.2101(17) ?
O3BA N1B . 1.2111(17) ?
O2BB N1B . 1.2118(17) ?
O3BB N1B . 1.2116(17) ?
O4BA N2B . 1.2109(16) ?
O5BA N2B . 1.2120(16) ?
O4BB N2B . 1.2119(17) ?
O5BB N2B . 1.2119(17) ?
O6BA N3B . 1.2132(16) ?
O7BA N3B . 1.2120(16) ?
O6BB N3B . 1.2116(17) ?
O7BB N3B . 1.2117(17) ?
N1B C2B . 1.528(5) ?
N2B C4B . 1.455(4) ?
N3B C6B . 1.461(5) ?
C1B C2B . 1.407(6) ?
C1B C6B . 1.437(6) ?
C2B C3B . 1.356(5) ?
C3B C4B . 1.350(6) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.376(6) ?
C5B C6B . 1.390(6) ?
C5B H5BA . 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cg1 Cg3 3.844(7) . 1_555 ?
Cg1 Cg4 3.677(9) . 1_555 ?
Cg2 Cg3 3.825(5) . 1_555 ?
Cg2 Cg4 3.634(2) . 1_555 ?
Cg3 Cg4 3.729(7) . 1_565 ?
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 O1A . 0.901(5) 1.770(9) 2.658(3) 168(3)
N2 H2N O1B . 0.897(5) 1.83(3) 2.603(3) 143(4)
N2 H2N O7BA . 0.897(5) 2.30(3) 3.047(5) 140(3)
C3 H3A O2AA . 0.97 2.50 3.214(8) 130
C3 H3A O2AB . 0.97 2.52 3.242(17) 131
C2 H2B O7AA . 0.97 2.48 3.304(5) 142
C2 H2B O7AB . 0.97 2.54 3.42(4) 151
C11 H11A O4BA 4_576 0.93 2.57 3.244(4) 130
C17 H17A O1A . 0.93 2.62 3.473(4) 154
C17 H17A O5BB 4_576 0.93 2.52 3.267(8) 138
C18A H18A Cg6 1_565 0.97 2.88 3.742(5) 148
C18A H18B Cg5 1_565 0.97 2.83 3.762000 161
C18A H18C Cg5 1_565 0.97 3.00 3.762000 137
C18A H18D Cg6 1_565 0.97 2.84 3.742(5) 155
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
C4 N1 C1 C2 . . . . -58.5(3) ?
C5 N1 C1 C2 . . . . 179.1(2) ?
C3 N2 C2 C1 . . . . -55.7(3) ?
C18A N2 C2 C1 . . . . 179.5(2) ?
N1 C1 C2 N2 . . . . 58.0(3) ?
C2 N2 C3 C4 . . . . 55.7(3) ?
C18A N2 C3 C4 . . . . -179.2(2) ?
C1 N1 C4 C3 . . . . 58.8(3) ?
C5 N1 C4 C3 . . . . -179.36(19) ?
N2 C3 C4 N1 . . . . -58.3(3) ?
C4 N1 C5 C6 . . . . 54.6(3) ?
C1 N1 C5 C6 . . . . 175.1(2) ?
C4 N1 C5 C12 . . . . 179.7(2) ?
C1 N1 C5 C12 . . . . -59.8(3) ?
C12 C5 C6 C7 . . . . 104.0(3) ?
N1 C5 C6 C7 . . . . -130.2(3) ?
C12 C5 C6 C11 . . . . -70.3(3) ?
N1 C5 C6 C11 . . . . 55.6(3) ?
C11 C6 C7 C8 . . . . 1.6(5) ?
C5 C6 C7 C8 . . . . -172.9(3) ?
C6 C7 C8 C9 . . . . -0.7(6) ?
C7 C8 C9 C10 . . . . -1.4(6) ?
C8 C9 C10 C11 . . . . 2.6(6) ?
C9 C10 C11 C6 . . . . -1.6(5) ?
C7 C6 C11 C10 . . . . -0.4(5) ?
C5 C6 C11 C10 . . . . 173.9(3) ?
C6 C5 C12 C13 . . . . -95.4(3) ?
N1 C5 C12 C13 . . . . 138.6(3) ?
C6 C5 C12 C17 . . . . 78.4(3) ?
N1 C5 C12 C17 . . . . -47.6(3) ?
C17 C12 C13 C14 . . . . -1.2(5) ?
C5 C12 C13 C14 . . . . 172.9(4) ?
C12 C13 C14 C15 . . . . 1.7(7) ?
C13 C14 C15 C16 . . . . -0.4(7) ?
C14 C15 C16 C17 . . . . -1.3(7) ?
C15 C16 C17 C12 . . . . 1.7(6) ?
C13 C12 C17 C16 . . . . -0.5(5) ?
C5 C12 C17 C16 . . . . -174.3(3) ?
C2 N2 C18A C19A . . . . 74.9(4) ?
C3 N2 C18A C19A . . . . -49.4(4) ?
N2 C18A C19A C20A . . . . -100.0(5) ?
C18A C19A C20A C21A . . . . -178.2(7) ?
C19A C20A C21A C22A . . . . -176.6(8) ?
C19A C20A C21A C26A . . . . 4(2) ?
C26A C21A C22A C23A . . . . 2(2) ?
C20A C21A C22A C23A . . . . -177.1(14) ?
C21A C22A C23A C24A . . . . 1(3) ?
C22A C23A C24A C25A . . . . -7(3) ?
C23A C24A C25A C26A . . . . 8(3) ?
C24A C25A C26A C21A . . . . -5(4) ?
C22A C21A C26A C25A . . . . 1(3) ?
C20A C21A C26A C25A . . . . 180(2) ?
C19B C20B C21B C26B . . . . 178.7(18) ?
C19B C20B C21B C22B . . . . -5(2) ?
C26B C21B C22B C23B . . . . -2(3) ?
C20B C21B C22B C23B . . . . -178(2) ?
C21B C22B C23B C24B . . . . 0(4) ?
C22B C23B C24B C25B . . . . 4(4) ?
C23B C24B C25B C26B . . . . -8(5) ?
C22B C21B C26B C25B . . . . -1(4) ?
C20B C21B C26B C25B . . . . 175(2) ?
C24B C25B C26B C21B . . . . 7(5) ?
O1A C1A C2A C3A . . . . -176.2(3) ?
C6A C1A C2A C3A . . . . 1.3(4) ?
O1A C1A C2A N1A . . . . 1.1(5) ?
C6A C1A C2A N1A . . . . 178.6(3) ?
O2AB N1A C2A C3A . . . . -146(2) ?
O2AA N1A C2A C3A . . . . -167.3(8) ?
O3AB N1A C2A C3A . . . . 50.1(18) ?
O3AA N1A C2A C3A . . . . 14.3(14) ?
O2AB N1A C2A C1A . . . . 37(2) ?
O2AA N1A C2A C1A . . . . 15.2(9) ?
O3AB N1A C2A C1A . . . . -127.4(18) ?
O3AA N1A C2A C1A . . . . -163.3(13) ?
C1A C2A C3A C4A . . . . -0.9(4) ?
N1A C2A C3A C4A . . . . -178.3(3) ?
C2A C3A C4A C5A . . . . 0.4(4) ?
C2A C3A C4A N2A . . . . 179.5(3) ?
O4A N2A C4A C3A . . . . 4.0(4) ?
O5A N2A C4A C3A . . . . -176.3(3) ?
O4A N2A C4A C5A . . . . -176.9(3) ?
O5A N2A C4A C5A . . . . 2.8(4) ?
C3A C4A C5A C6A . . . . -0.5(5) ?
N2A C4A C5A C6A . . . . -179.6(3) ?
C4A C5A C6A N3A . . . . 179.0(3) ?
C4A C5A C6A C1A . . . . 1.1(5) ?
O7AA N3A C6A C5A . . . . 160.3(7) ?
O7AB N3A C6A C5A . . . . 119(3) ?
O6AB N3A C6A C5A . . . . -62(2) ?
O6AA N3A C6A C5A . . . . -20.9(7) ?
O7AA N3A C6A C1A . . . . -21.7(8) ?
O7AB N3A C6A C1A . . . . -63(3) ?
O6AB N3A C6A C1A . . . . 116(2) ?
O6AA N3A C6A C1A . . . . 157.1(6) ?
O1A C1A C6A C5A . . . . 176.1(3) ?
C2A C1A C6A C5A . . . . -1.4(4) ?
O1A C1A C6A N3A . . . . -1.7(5) ?
C2A C1A C6A N3A . . . . -179.3(3) ?
O1B C1B C2B C3B . . . . 179.4(4) ?
C6B C1B C2B C3B . . . . 0.6(5) ?
O1B C1B C2B N1B . . . . 3.7(5) ?
C6B C1B C2B N1B . . . . -175.1(3) ?
O2BA N1B C2B C3B . . . . 151.3(6) ?
O3BA N1B C2B C3B . . . . -24.4(10) ?
O3BB N1B C2B C3B . . . . -37(4) ?
O2BB N1B C2B C3B . . . . 169.8(18) ?
O2BA N1B C2B C1B . . . . -32.6(7) ?
O3BA N1B C2B C1B . . . . 151.8(9) ?
O3BB N1B C2B C1B . . . . 139(4) ?
O2BB N1B C2B C1B . . . . -14.1(19) ?
C1B C2B C3B C4B . . . . -0.6(5) ?
N1B C2B C3B C4B . . . . 175.5(3) ?
C2B C3B C4B C5B . . . . 0.3(5) ?
C2B C3B C4B N2B . . . . -177.4(3) ?
O4BA N2B C4B C3B . . . . -6.4(6) ?
O4BB N2B C4B C3B . . . . -25(3) ?
O5BB N2B C4B C3B . . . . 142(3) ?
O5BA N2B C4B C3B . . . . 172.7(5) ?
O4BA N2B C4B C5B . . . . 175.9(4) ?
O4BB N2B C4B C5B . . . . 157(3) ?
O5BB N2B C4B C5B . . . . -36(3) ?
O5BA N2B C4B C5B . . . . -5.1(6) ?
C3B C4B C5B C6B . . . . -0.1(5) ?
N2B C4B C5B C6B . . . . 177.7(3) ?
C4B C5B C6B C1B . . . . 0.1(5) ?
C4B C5B C6B N3B . . . . 177.7(3) ?
O1B C1B C6B C5B . . . . -178.9(4) ?
C2B C1B C6B C5B . . . . -0.3(5) ?
O1B C1B C6B N3B . . . . 3.4(6) ?
C2B C1B C6B N3B . . . . -178.0(3) ?
O6BB N3B C6B C5B . . . . 19.3(11) ?
O7BB N3B C6B C5B . . . . 162(2) ?
O7BA N3B C6B C5B . . . . 163.2(7) ?
O6BA N3B C6B C5B . . . . -25.8(7) ?
O6BB N3B C6B C1B . . . . -162.9(11) ?
O7BB N3B C6B C1B . . . . -20(2) ?
O7BA N3B C6B C1B . . . . -19.0(9) ?
O6BA N3B C6B C1B . . . . 152.0(5) ?
