#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/48/2224856.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_2224856
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Hakim Al-Arique, Q. N. M.'
'Yathirajan, H. S.'
'Narayana, B.'
_publ_section_title
;
 Imatinibium dipicrate
;
_journal_coeditor_code           BT5129
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o411
_journal_page_last               o412
_journal_paper_doi               10.1107/S1600536810000577
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C29 H33 N7 O 2+, 2C6 H2 N3 O7 -'
_chemical_formula_moiety         'C29 H33 N7 O 2+, 2(C6 H2 N3 O7 -)'
_chemical_formula_sum            'C41 H37 N13 O15'
_chemical_formula_weight         951.84
_chemical_name_common            'imatinibium dipicrate'
_chemical_name_systematic
;
1-Methyl-4-(4-{4-methyl-3-[4-(3-pyridyl)pyrimidin-2-
ylamino]anilinocarbonyl}benzyl)piperazine-1,4-diium dipicrate
;
_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                96.74(3)
_cell_angle_beta                 92.69(2)
_cell_angle_gamma                101.46(7)
_cell_formula_units_Z            2
_cell_length_a                   8.560000
_cell_length_b                   10.734000
_cell_length_c                   23.060000
_cell_measurement_reflns_used    9389
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      73.9674
_cell_measurement_theta_min      4.2265
_cell_volume                     2056.9(6)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics
;
SHELXTL (Version 6.10; Sheldrick, 2008) and Mercury
(Macrae et
al., 2006)
;
_computing_publication_material
;
SHELXTL (Version 6.10; Sheldrick, 2008), enCIFer
(Allen et al., 2004)
and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
;
_diffrn_measurement_method       'ω scans'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15890
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.12
_diffrn_reflns_theta_min         4.24
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  0.782
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         8082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0615P)²+3.3059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                6946
_reflns_number_total             8082
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5129.cif
_cod_data_source_block           I
_cod_database_code               2224856
_cod_database_fobs_code          2224856
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
O O1 0.3153(2) 0.58462(17) 0.49702(9) 0.0356(4) Uani d . 1 . .
N N1 0.4213(2) 0.4360(2) 0.19545(10) 0.0242(4) Uani d . 1 . .
H H1 0.465(4) 0.514(3) 0.2058(13) 0.028(8) Uiso d . 1 . .
N N2 0.2325(3) 0.4773(2) 0.09313(10) 0.0259(5) Uani d . 1 . .
H H2 0.182(4) 0.397(4) 0.0809(15) 0.044(9) Uiso d . 1 . .
C C1 0.4665(3) 0.4017(2) 0.13475(12) 0.0274(5) Uani d . 1 . .
H H1A 0.4187 0.3106 0.1211 0.033 Uiso calc R 1 . .
H H1B 0.5841 0.4127 0.1349 0.033 Uiso calc R 1 . .
C C2 0.4094(3) 0.4851(2) 0.09331(12) 0.0291(5) Uani d . 1 . .
H H2A 0.4655 0.5752 0.1049 0.035 Uiso calc R 1 . .
H H2B 0.4371 0.4581 0.0532 0.035 Uiso calc R 1 . .
C C3 0.1853(3) 0.5056(2) 0.15391(11) 0.0264(5) Uani d . 1 . .
H H3A 0.0675 0.4925 0.1534 0.032 Uiso calc R 1 . .
H H3B 0.2307 0.5965 0.1689 0.032 Uiso calc R 1 . .
C C4 0.2433(3) 0.4209(2) 0.19414(11) 0.0255(5) Uani d . 1 . .
H H4A 0.2118 0.4431 0.2342 0.031 Uiso calc R 1 . .
H H4B 0.1922 0.3303 0.1807 0.031 Uiso calc R 1 . .
C C5 0.1813(4) 0.5660(3) 0.05447(13) 0.0342(6) Uani d . 1 . .
H H5A 0.0661 0.5612 0.0558 0.051 Uiso calc R 1 . .
H H5B 0.2058 0.5413 0.0142 0.051 Uiso calc R 1 . .
H H5C 0.2386 0.6539 0.0680 0.051 Uiso calc R 1 . .
C C6 0.4812(3) 0.3553(2) 0.23719(12) 0.0294(6) Uani d . 1 . .
H H6A 0.4361 0.2637 0.2235 0.035 Uiso calc R 1 . .
H H6B 0.5990 0.3686 0.2370 0.035 Uiso calc R 1 . .
C C7 0.4370(3) 0.3868(2) 0.29871(12) 0.0284(5) Uani d . 1 . .
C C8 0.5091(3) 0.5012(2) 0.33399(12) 0.0305(6) Uani d . 1 . .
H H8A 0.5904 0.5608 0.3193 0.037 Uiso calc R 1 . .
C C9 0.4627(3) 0.5279(2) 0.38995(12) 0.0304(6) Uani d . 1 . .
H H9A 0.5108 0.6066 0.4130 0.036 Uiso calc R 1 . .
C C10 0.3464(3) 0.4409(2) 0.41296(12) 0.0276(5) Uani d . 1 . .
C C11 0.2752(3) 0.3270(2) 0.37767(12) 0.0279(5) Uani d . 1 . .
H H11A 0.1957 0.2667 0.3927 0.033 Uiso calc R 1 . .
C C12 0.3182(3) 0.3006(2) 0.32147(12) 0.0289(6) Uani d . 1 . .
H H12A 0.2668 0.2233 0.2980 0.035 Uiso calc R 1 . .
C C13 0.2977(3) 0.4734(2) 0.47391(12) 0.0292(5) Uani d . 1 . .
N N14 0.2326(3) 0.3702(2) 0.49985(10) 0.0290(5) Uani d . 1 . .
H H14 0.250(4) 0.298(3) 0.4857(13) 0.030(8) Uiso d . 1 . .
C C15 0.1556(3) 0.3663(2) 0.55298(12) 0.0276(5) Uani d . 1 . .
C C16 0.0846(3) 0.4640(3) 0.57780(12) 0.0314(6) Uani d . 1 . .
H H16A 0.0945 0.5428 0.5620 0.038 Uiso calc R 1 . .
C C17 -0.0012(3) 0.4419(3) 0.62653(13) 0.0339(6) Uani d . 1 . .
H H17A -0.0498 0.5080 0.6438 0.041 Uiso calc R 1 . .
C C18 -0.0199(3) 0.3286(3) 0.65133(12) 0.0315(6) Uani d . 1 . .
C C19 -0.1298(4) 0.3073(3) 0.70004(14) 0.0437(7) Uani d . 1 . .
H H19A -0.0708 0.2871 0.7340 0.066 Uiso calc R 1 . .
H H19B -0.2194 0.2357 0.6867 0.066 Uiso calc R 1 . .
H H19C -0.1708 0.3851 0.7111 0.066 Uiso calc R 1 . .
C C20 0.0583(3) 0.2345(2) 0.62720(11) 0.0264(5) Uani d . 1 . .
C C21 0.1447(3) 0.2542(2) 0.57814(12) 0.0274(5) Uani d . 1 . .
H H21A 0.1971 0.1896 0.5617 0.033 Uiso calc R 1 . .
N N22 0.0369(3) 0.1166(2) 0.65091(10) 0.0295(5) Uani d . 1 . .
H H22 -0.053(4) 0.098(3) 0.6678(15) 0.040(9) Uiso d . 1 . .
C C23 0.1200(3) 0.0202(2) 0.64192(11) 0.0264(5) Uani d . 1 . .
N N24 0.0467(3) -0.0938(2) 0.65697(10) 0.0304(5) Uani d . 1 . .
C C25 0.1278(3) -0.1869(3) 0.64831(13) 0.0341(6) Uani d . 1 . .
H H25A 0.0816 -0.2684 0.6589 0.041 Uiso calc R 1 . .
C C26 0.2749(3) -0.1733(2) 0.62498(13) 0.0322(6) Uani d . 1 . .
H H26A 0.3286 -0.2426 0.6189 0.039 Uiso calc R 1 . .
C C27 0.3399(3) -0.0522(2) 0.61095(11) 0.0267(5) Uani d . 1 . .
N N28 0.2636(3) 0.0452(2) 0.62024(9) 0.0270(5) Uani d . 1 . .
C C29 0.4951(3) -0.0229(2) 0.58435(11) 0.0267(5) Uani d . 1 . .
C C30 0.5691(3) -0.1204(2) 0.56171(12) 0.0290(5) Uani d . 1 . .
H H30A 0.5167 -0.2065 0.5635 0.035 Uiso calc R 1 . .
N N31 0.7095(3) -0.1001(2) 0.53756(10) 0.0314(5) Uani d . 1 . .
C C32 0.7788(3) 0.0217(3) 0.53364(12) 0.0303(6) Uani d . 1 . .
H H32A 0.8790 0.0380 0.5169 0.036 Uiso calc R 1 . .
C C33 0.7121(3) 0.1247(3) 0.55272(12) 0.0308(6) Uani d . 1 . .
H H33A 0.7635 0.2094 0.5479 0.037 Uiso calc R 1 . .
C C34 0.5695(3) 0.1028(2) 0.57896(12) 0.0291(5) Uani d . 1 . .
H H34A 0.5225 0.1724 0.5932 0.035 Uiso calc R 1 . .
O O1A 0.1518(2) 0.22087(16) 0.07622(8) 0.0291(4) Uani d . 1 . .
O O21A 0.3381(2) 0.07732(17) 0.12752(9) 0.0346(4) Uani d . 1 . .
O O22A 0.3131(2) -0.0904(2) 0.06313(10) 0.0396(5) Uani d . 1 . .
O O41A -0.2360(2) -0.33957(17) 0.04481(10) 0.0395(5) Uani d . 1 . .
O O42A -0.4305(2) -0.2407(2) 0.03722(12) 0.0493(6) Uani d . 1 . .
O O61A -0.3332(3) 0.2150(2) 0.07480(12) 0.0520(6) Uani d . 1 . .
O O62A -0.1032(3) 0.32666(18) 0.06299(11) 0.0427(5) Uani d . 1 . .
N N2A 0.2595(3) -0.0043(2) 0.08996(10) 0.0287(5) Uani d . 1 . .
N N4A -0.2888(3) -0.2408(2) 0.04636(10) 0.0311(5) Uani d . 1 . .
N N6A -0.1906(3) 0.2244(2) 0.06879(10) 0.0301(5) Uani d . 1 . .
C C1A 0.0479(3) 0.1211(2) 0.07465(10) 0.0242(5) Uani d . 1 . .
C C2A 0.0909(3) -0.0022(2) 0.07761(11) 0.0253(5) Uani d . 1 . .
C C3A -0.0144(3) -0.1176(2) 0.06785(11) 0.0265(5) Uani d . 1 . .
H H3AA 0.0223 -0.1956 0.0674 0.032 Uiso calc R 1 . .
C C4A -0.1766(3) -0.1186(2) 0.05852(11) 0.0272(5) Uani d . 1 . .
C C5A -0.2330(3) -0.0062(2) 0.06039(11) 0.0261(5) Uani d . 1 . .
H H5AA -0.3445 -0.0084 0.0562 0.031 Uiso calc R 1 . .
C C6A -0.1240(3) 0.1095(2) 0.06843(11) 0.0259(5) Uani d . 1 . .
O O1B 0.4787(2) 0.68998(16) 0.21876(9) 0.0303(4) Uani d . 1 . .
O O21B 0.2684(2) 0.84672(18) 0.19341(9) 0.0348(4) Uani d . 1 . .
O O22B 0.3412(3) 0.9982(2) 0.26585(11) 0.0493(6) Uani d . 1 . .
O O41B 0.8703(3) 1.24447(18) 0.21586(10) 0.0441(5) Uani d . 1 . .
O O42B 1.0597(2) 1.13663(18) 0.20751(9) 0.0363(5) Uani d . 1 . .
O O61B 0.9270(2) 0.6835(2) 0.16693(9) 0.0392(5) Uani d . 1 . .
O O62B 0.7440(2) 0.58469(18) 0.21578(10) 0.0405(5) Uani d . 1 . .
N N2B 0.3710(3) 0.9196(2) 0.22702(11) 0.0316(5) Uani d . 1 . .
N N4B 0.9186(3) 1.1430(2) 0.21198(10) 0.0327(5) Uani d . 1 . .
N N6B 0.8091(3) 0.6809(2) 0.19535(10) 0.0285(5) Uani d . 1 . .
C C1B 0.5803(3) 0.7898(2) 0.21517(11) 0.0248(5) Uani d . 1 . .
C C2B 0.5386(3) 0.9143(2) 0.22026(11) 0.0267(5) Uani d . 1 . .
C C3B 0.6441(3) 1.0279(2) 0.22022(12) 0.0298(6) Uani d . 1 . .
H H3BA 0.6099 1.1072 0.2255 0.036 Uiso calc R 1 . .
C C4B 0.8035(3) 1.0239(2) 0.21222(11) 0.0281(5) Uani d . 1 . .
C C5B 0.8561(3) 0.9107(2) 0.20437(11) 0.0263(5) Uani d . 1 . .
H H5BA 0.9650 0.9103 0.1982 0.032 Uiso calc R 1 . .
C C6B 0.7471(3) 0.7972(2) 0.20563(11) 0.0257(5) Uani 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 0.0181 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
C1 N1 C4 . . 108.6(2) ?
C1 N1 C6 . . 111.1(2) ?
C4 N1 C6 . . 111.62(19) ?
C1 N1 H1 . . 107(2) ?
C4 N1 H1 . . 109(2) ?
C6 N1 H1 . . 109(2) ?
C3 N2 C5 . . 110.9(2) ?
C3 N2 C2 . . 110.4(2) ?
C5 N2 C2 . . 110.8(2) ?
C3 N2 H2 . . 105(2) ?
C5 N2 H2 . . 110(2) ?
C2 N2 H2 . . 109(2) ?
N1 C1 C2 . . 110.9(2) ?
N1 C1 H1A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.0 ?
N2 C2 C1 . . 112.1(2) ?
N2 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
N2 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
N2 C3 C4 . . 111.5(2) ?
N2 C3 H3A . . 109.3 ?
C4 C3 H3A . . 109.3 ?
N2 C3 H3B . . 109.3 ?
C4 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
N1 C4 C3 . . 111.2(2) ?
N1 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
N1 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
N2 C5 H5A . . 109.5 ?
N2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 C6 N1 . . 112.6(2) ?
C7 C6 H6A . . 109.1 ?
N1 C6 H6A . . 109.1 ?
C7 C6 H6B . . 109.1 ?
N1 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.8 ?
C12 C7 C8 . . 118.6(3) ?
C12 C7 C6 . . 119.2(2) ?
C8 C7 C6 . . 122.2(2) ?
C9 C8 C7 . . 120.4(2) ?
C9 C8 H8A . . 119.8 ?
C7 C8 H8A . . 119.8 ?
C8 C9 C10 . . 120.9(2) ?
C8 C9 H9A . . 119.5 ?
C10 C9 H9A . . 119.5 ?
C9 C10 C11 . . 118.4(3) ?
C9 C10 C13 . . 119.6(2) ?
C11 C10 C13 . . 122.1(2) ?
C12 C11 C10 . . 121.2(2) ?
C12 C11 H11A . . 119.4 ?
C10 C11 H11A . . 119.4 ?
C11 C12 C7 . . 120.4(2) ?
C11 C12 H12A . . 119.8 ?
C7 C12 H12A . . 119.8 ?
O1 C13 N14 . . 123.9(3) ?
O1 C13 C10 . . 121.8(2) ?
N14 C13 C10 . . 114.3(2) ?
C13 N14 C15 . . 129.0(2) ?
C13 N14 H14 . . 117(2) ?
C15 N14 H14 . . 113(2) ?
C21 C15 C16 . . 120.2(2) ?
C21 C15 N14 . . 116.1(2) ?
C16 C15 N14 . . 123.6(2) ?
C17 C16 C15 . . 117.5(2) ?
C17 C16 H16A . . 121.2 ?
C15 C16 H16A . . 121.2 ?
C18 C17 C16 . . 123.6(2) ?
C18 C17 H17A . . 118.2 ?
C16 C17 H17A . . 118.2 ?
C17 C18 C20 . . 117.6(3) ?
C17 C18 C19 . . 120.0(3) ?
C20 C18 C19 . . 122.2(3) ?
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 ?
C21 C20 C18 . . 119.8(2) ?
C21 C20 N22 . . 121.6(2) ?
C18 C20 N22 . . 118.4(2) ?
C15 C21 C20 . . 121.1(2) ?
C15 C21 H21A . . 119.5 ?
C20 C21 H21A . . 119.5 ?
C23 N22 C20 . . 129.0(2) ?
C23 N22 H22 . . 116(2) ?
C20 N22 H22 . . 113(2) ?
N28 C23 N24 . . 125.8(2) ?
N28 C23 N22 . . 119.1(2) ?
N24 C23 N22 . . 115.2(2) ?
C25 N24 C23 . . 115.0(2) ?
N24 C25 C26 . . 124.4(2) ?
N24 C25 H25A . . 117.8 ?
C26 C25 H25A . . 117.8 ?
C25 C26 C27 . . 116.1(2) ?
C25 C26 H26A . . 121.9 ?
C27 C26 H26A . . 121.9 ?
N28 C27 C26 . . 121.4(2) ?
N28 C27 C29 . . 116.0(2) ?
C26 C27 C29 . . 122.6(2) ?
C23 N28 C27 . . 117.3(2) ?
C30 C29 C34 . . 117.4(2) ?
C30 C29 C27 . . 121.1(2) ?
C34 C29 C27 . . 121.5(2) ?
N31 C30 C29 . . 123.9(2) ?
N31 C30 H30A . . 118.0 ?
C29 C30 H30A . . 118.0 ?
C30 N31 C32 . . 117.1(2) ?
N31 C32 C33 . . 123.3(3) ?
N31 C32 H32A . . 118.4 ?
C33 C32 H32A . . 118.4 ?
C34 C33 C32 . . 119.0(2) ?
C34 C33 H33A . . 120.5 ?
C32 C33 H33A . . 120.5 ?
C33 C34 C29 . . 119.2(2) ?
C33 C34 H34A . . 120.4 ?
C29 C34 H34A . . 120.4 ?
O21A N2A O22A . . 123.7(2) ?
O21A N2A C2A . . 118.4(2) ?
O22A N2A C2A . . 117.9(2) ?
O42A N4A O41A . . 123.1(2) ?
O42A N4A C4A . . 118.6(2) ?
O41A N4A C4A . . 118.2(2) ?
O61A N6A O62A . . 122.0(2) ?
O61A N6A C6A . . 118.4(2) ?
O62A N6A C6A . . 119.6(2) ?
O1A C1A C2A . . 121.3(2) ?
O1A C1A C6A . . 126.9(2) ?
C2A C1A C6A . . 111.7(2) ?
C3A C2A C1A . . 124.6(2) ?
C3A C2A N2A . . 117.3(2) ?
C1A C2A N2A . . 118.0(2) ?
C2A C3A C4A . . 118.7(2) ?
C2A C3A H3AA . . 120.6 ?
C4A C3A H3AA . . 120.6 ?
C5A C4A C3A . . 121.5(2) ?
C5A C4A N4A . . 119.4(2) ?
C3A C4A N4A . . 119.1(2) ?
C4A C5A C6A . . 118.8(2) ?
C4A C5A H5AA . . 120.6 ?
C6A C5A H5AA . . 120.6 ?
C5A C6A C1A . . 124.0(2) ?
C5A C6A N6A . . 116.2(2) ?
C1A C6A N6A . . 119.7(2) ?
O21B N2B O22B . . 123.7(2) ?
O21B N2B C2B . . 118.5(2) ?
O22B N2B C2B . . 117.8(2) ?
O42B N4B O41B . . 123.7(2) ?
O42B N4B C4B . . 117.7(2) ?
O41B N4B C4B . . 118.7(2) ?
O61B N6B O62B . . 122.5(2) ?
O61B N6B C6B . . 118.1(2) ?
O62B N6B C6B . . 119.4(2) ?
O1B C1B C6B . . 126.3(2) ?
O1B C1B C2B . . 121.7(2) ?
C6B C1B C2B . . 112.0(2) ?
C3B C2B C1B . . 125.1(2) ?
C3B C2B N2B . . 117.4(2) ?
C1B C2B N2B . . 117.6(2) ?
C2B C3B C4B . . 117.9(2) ?
C2B C3B H3BA . . 121.1 ?
C4B C3B H3BA . . 121.1 ?
C5B C4B C3B . . 122.3(2) ?
C5B C4B N4B . . 118.5(2) ?
C3B C4B N4B . . 119.3(2) ?
C4B C5B C6B . . 118.6(2) ?
C4B C5B H5BA . . 120.7 ?
C6B C5B H5BA . . 120.7 ?
C5B C6B C1B . . 124.1(2) ?
C5B C6B N6B . . 115.8(2) ?
C1B C6B N6B . . 120.1(2) ?
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 C13 . 1.226(3) ?
N1 C1 . 1.494(3) ?
N1 C4 . 1.498(3) ?
N1 C6 . 1.505(3) ?
N1 H1 . 0.85(3) ?
N2 C3 . 1.490(3) ?
N2 C5 . 1.491(3) ?
N2 C2 . 1.500(3) ?
N2 H2 . 0.89(4) ?
C1 C2 . 1.511(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.506(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C7 . 1.503(4) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C12 . 1.399(4) ?
C7 C8 . 1.403(4) ?
C8 C9 . 1.383(4) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.393(4) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.397(3) ?
C10 C13 . 1.506(4) ?
C11 C12 . 1.377(4) ?
C11 H11A . 0.9500 ?
C12 H12A . 0.9500 ?
C13 N14 . 1.356(3) ?
N14 C15 . 1.419(3) ?
N14 H14 . 0.85(3) ?
C15 C21 . 1.385(4) ?
C15 C16 . 1.394(4) ?
C16 C17 . 1.389(4) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.388(4) ?
C17 H17A . 0.9500 ?
C18 C20 . 1.396(4) ?
C18 C19 . 1.508(4) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 C21 . 1.394(4) ?
C20 N22 . 1.419(3) ?
C21 H21A . 0.9500 ?
N22 C23 . 1.369(3) ?
N22 H22 . 0.87(4) ?
C23 N28 . 1.339(3) ?
C23 N24 . 1.352(3) ?
N24 C25 . 1.328(4) ?
C25 C26 . 1.380(4) ?
C25 H25A . 0.9500 ?
C26 C27 . 1.390(4) ?
C26 H26A . 0.9500 ?
C27 N28 . 1.341(3) ?
C27 C29 . 1.482(4) ?
C29 C30 . 1.391(4) ?
C29 C34 . 1.395(4) ?
C30 N31 . 1.338(4) ?
C30 H30A . 0.9500 ?
N31 C32 . 1.340(4) ?
C32 C33 . 1.379(4) ?
C32 H32A . 0.9500 ?
C33 C34 . 1.378(4) ?
C33 H33A . 0.9500 ?
C34 H34A . 0.9500 ?
O1A C1A . 1.245(3) ?
O21A N2A . 1.226(3) ?
O22A N2A . 1.228(3) ?
O41A N4A . 1.231(3) ?
O42A N4A . 1.221(3) ?
O61A N6A . 1.221(3) ?
O62A N6A . 1.225(3) ?
N2A C2A . 1.463(3) ?
N4A C4A . 1.452(3) ?
N6A C6A . 1.457(3) ?
C1A C2A . 1.451(3) ?
C1A C6A . 1.451(4) ?
C2A C3A . 1.367(3) ?
C3A C4A . 1.393(4) ?
C3A H3AA . 0.9500 ?
C4A C5A . 1.382(4) ?
C5A C6A . 1.384(3) ?
C5A H5AA . 0.9500 ?
O1B C1B . 1.252(3) ?
O21B N2B . 1.227(3) ?
O22B N2B . 1.228(3) ?
O41B N4B . 1.235(3) ?
O42B N4B . 1.232(3) ?
O61B N6B . 1.226(3) ?
O62B N6B . 1.229(3) ?
N2B C2B . 1.462(3) ?
N4B C4B . 1.451(3) ?
N6B C6B . 1.450(3) ?
C1B C6B . 1.443(4) ?
C1B C2B . 1.443(3) ?
C2B C3B . 1.366(4) ?
C3B C4B . 1.394(4) ?
C3B H3BA . 0.9500 ?
C4B C5B . 1.373(4) ?
C5B C6B . 1.384(3) ?
C5B H5BA . 0.9500 ?
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 H1 O1B . 0.85(3) 1.85(3) 2.658(3) 157(3)
N1 H1 O62B . 0.85(3) 2.35(3) 2.890(3) 122(2)
N2 H2 O1A . 0.89(4) 1.85(4) 2.678(3) 154(3)
N2 H2 O62A . 0.89(4) 2.41(4) 3.009(3) 125(3)
N14 H14 N31 2_656 0.85(3) 2.23(3) 3.069(3) 171(3)
C5 H5B O41A 2 0.98 2.48 3.258(4) 135.7
C4 H4B O42B 1_445 0.99 2.33 3.199(3) 146.2
C3 H3A O61B 1_455 0.99 2.57 3.199(3) 121.3
C3 H3B O1B . 0.99 2.34 3.072(3) 129.8
C12 H12A O42B 1_445 0.95 2.63 3.423(3) 141.6
C19 H19A O61B 2_666 0.98 2.50 3.435(4) 159.4
C19 H19A N6B 2_666 0.98 2.65 3.541(4) 151.7
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C2 . . . . 58.2(2) ?
C6 N1 C1 C2 . . . . -178.6(2) ?
C3 N2 C2 C1 . . . . 53.6(3) ?
C5 N2 C2 C1 . . . . 176.8(2) ?
N1 C1 C2 N2 . . . . -56.6(3) ?
C5 N2 C3 C4 . . . . -177.2(2) ?
C2 N2 C3 C4 . . . . -54.0(3) ?
C1 N1 C4 C3 . . . . -59.2(3) ?
C6 N1 C4 C3 . . . . 177.9(2) ?
N2 C3 C4 N1 . . . . 58.1(3) ?
C1 N1 C6 C7 . . . . -179.7(2) ?
C4 N1 C6 C7 . . . . -58.3(3) ?
N1 C6 C7 C12 . . . . 107.2(3) ?
N1 C6 C7 C8 . . . . -71.7(3) ?
C12 C7 C8 C9 . . . . -0.3(4) ?
C6 C7 C8 C9 . . . . 178.6(2) ?
C7 C8 C9 C10 . . . . 1.5(4) ?
C8 C9 C10 C11 . . . . -1.3(4) ?
C8 C9 C10 C13 . . . . -179.5(2) ?
C9 C10 C11 C12 . . . . 0.0(4) ?
C13 C10 C11 C12 . . . . 178.1(2) ?
C10 C11 C12 C7 . . . . 1.2(4) ?
C8 C7 C12 C11 . . . . -1.0(4) ?
C6 C7 C12 C11 . . . . -180.0(2) ?
C9 C10 C13 O1 . . . . 23.7(4) ?
C11 C10 C13 O1 . . . . -154.5(3) ?
C9 C10 C13 N14 . . . . -156.9(2) ?
C11 C10 C13 N14 . . . . 25.0(4) ?
O1 C13 N14 C15 . . . . 8.6(4) ?
C10 C13 N14 C15 . . . . -170.8(2) ?
C13 N14 C15 C21 . . . . -160.7(3) ?
C13 N14 C15 C16 . . . . 23.3(4) ?
C21 C15 C16 C17 . . . . -2.5(4) ?
N14 C15 C16 C17 . . . . 173.3(3) ?
C15 C16 C17 C18 . . . . -0.2(4) ?
C16 C17 C18 C20 . . . . 2.9(4) ?
C16 C17 C18 C19 . . . . -173.3(3) ?
C17 C18 C20 C21 . . . . -3.0(4) ?
C19 C18 C20 C21 . . . . 173.1(3) ?
C17 C18 C20 N22 . . . . -178.2(2) ?
C19 C18 C20 N22 . . . . -2.1(4) ?
C16 C15 C21 C20 . . . . 2.4(4) ?
N14 C15 C21 C20 . . . . -173.7(2) ?
C18 C20 C21 C15 . . . . 0.4(4) ?
N22 C20 C21 C15 . . . . 175.5(2) ?
C21 C20 N22 C23 . . . . 17.2(4) ?
C18 C20 N22 C23 . . . . -167.7(3) ?
C20 N22 C23 N28 . . . . 18.2(4) ?
C20 N22 C23 N24 . . . . -162.5(2) ?
N28 C23 N24 C25 . . . . -0.6(4) ?
N22 C23 N24 C25 . . . . -179.8(2) ?
C23 N24 C25 C26 . . . . -1.0(4) ?
N24 C25 C26 C27 . . . . 1.0(4) ?
C25 C26 C27 N28 . . . . 0.6(4) ?
C25 C26 C27 C29 . . . . -178.6(2) ?
N24 C23 N28 C27 . . . . 2.1(4) ?
N22 C23 N28 C27 . . . . -178.7(2) ?
C26 C27 N28 C23 . . . . -2.0(4) ?
C29 C27 N28 C23 . . . . 177.2(2) ?
N28 C27 C29 C30 . . . . -166.7(2) ?
C26 C27 C29 C30 . . . . 12.6(4) ?
N28 C27 C29 C34 . . . . 10.8(4) ?
C26 C27 C29 C34 . . . . -170.0(3) ?
C34 C29 C30 N31 . . . . 3.0(4) ?
C27 C29 C30 N31 . . . . -179.5(2) ?
C29 C30 N31 C32 . . . . -2.2(4) ?
C30 N31 C32 C33 . . . . -0.4(4) ?
N31 C32 C33 C34 . . . . 2.2(4) ?
C32 C33 C34 C29 . . . . -1.4(4) ?
C30 C29 C34 C33 . . . . -1.0(4) ?
C27 C29 C34 C33 . . . . -178.6(2) ?
O1A C1A C2A C3A . . . . -170.2(2) ?
C6A C1A C2A C3A . . . . 8.4(4) ?
O1A C1A C2A N2A . . . . 7.6(4) ?
C6A C1A C2A N2A . . . . -173.8(2) ?
O21A N2A C2A C3A . . . . -140.1(2) ?
O22A N2A C2A C3A . . . . 37.9(3) ?
O21A N2A C2A C1A . . . . 41.9(3) ?
O22A N2A C2A C1A . . . . -140.1(2) ?
C1A C2A C3A C4A . . . . -4.9(4) ?
N2A C2A C3A C4A . . . . 177.2(2) ?
C2A C3A C4A C5A . . . . -1.6(4) ?
C2A C3A C4A N4A . . . . 178.2(2) ?
O42A N4A C4A C5A . . . . 1.1(4) ?
O41A N4A C4A C5A . . . . 179.9(2) ?
O42A N4A C4A C3A . . . . -178.7(3) ?
O41A N4A C4A C3A . . . . 0.1(4) ?
C3A C4A C5A C6A . . . . 3.7(4) ?
N4A C4A C5A C6A . . . . -176.1(2) ?
C4A C5A C6A C1A . . . . 0.5(4) ?
C4A C5A C6A N6A . . . . 178.8(2) ?
O1A C1A C6A C5A . . . . 172.4(2) ?
C2A C1A C6A C5A . . . . -6.1(3) ?
O1A C1A C6A N6A . . . . -5.8(4) ?
C2A C1A C6A N6A . . . . 175.8(2) ?
O61A N6A C6A C5A . . . . 15.5(4) ?
O62A N6A C6A C5A . . . . -164.3(2) ?
O61A N6A C6A C1A . . . . -166.2(3) ?
O62A N6A C6A C1A . . . . 14.0(4) ?
O1B C1B C2B C3B . . . . 176.0(3) ?
C6B C1B C2B C3B . . . . -4.2(4) ?
O1B C1B C2B N2B . . . . -2.9(4) ?
C6B C1B C2B N2B . . . . 176.9(2) ?
O21B N2B C2B C3B . . . . 132.4(3) ?
O22B N2B C2B C3B . . . . -46.8(4) ?
O21B N2B C2B C1B . . . . -48.7(3) ?
O22B N2B C2B C1B . . . . 132.2(3) ?
C1B C2B C3B C4B . . . . 2.8(4) ?
N2B C2B C3B C4B . . . . -178.3(2) ?
C2B C3B C4B C5B . . . . 0.2(4) ?
C2B C3B C4B N4B . . . . -180.0(2) ?
O42B N4B C4B C5B . . . . -3.4(4) ?
O41B N4B C4B C5B . . . . 176.1(2) ?
O42B N4B C4B C3B . . . . 176.7(2) ?
O41B N4B C4B C3B . . . . -3.7(4) ?
C3B C4B C5B C6B . . . . -1.3(4) ?
N4B C4B C5B C6B . . . . 178.9(2) ?
C4B C5B C6B C1B . . . . -0.5(4) ?
C4B C5B C6B N6B . . . . 178.3(2) ?
O1B C1B C6B C5B . . . . -177.2(3) ?
C2B C1B C6B C5B . . . . 3.0(4) ?
O1B C1B C6B N6B . . . . 4.1(4) ?
C2B C1B C6B N6B . . . . -175.7(2) ?
O61B N6B C6B C5B . . . . -25.5(3) ?
O62B N6B C6B C5B . . . . 153.6(2) ?
O61B N6B C6B C1B . . . . 153.3(2) ?
O62B N6B C6B C1B . . . . -27.6(4) ?
