#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229489.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_2229489
loop_
_publ_author_name
'Anh, Le Tuan'
'Hieu, Truong Hong'
'Soldatenkov, Anatoly T.'
'Soldatova, Svetlana A.'
'Khrustalev, Victor N.'
_publ_section_title
;
 9-[(2-Hydroxybenzylidene)amino]-11-(2-hydroxyphenyl)-10,13-diphenyl-8-oxa-12-azoniatricyclo[7.3.1.0^2,7^]trideca-2(7),3,5-triene
 acetate ethanol disolvate
;
_journal_coeditor_code           RK2264
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o560
_journal_page_last               o561
_journal_paper_doi               10.1107/S160053681100376X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C36 H31 N2 O3 +, C2 H3 O2 -, 2C2 H6 O'
_chemical_formula_moiety         'C36 H31 N2 O3 +, C2 H3 O2 -, 2(C2 H6 O)'
_chemical_formula_sum            'C42 H46 N2 O7'
_chemical_formula_weight         690.81
_chemical_melting_point_gt       451
_chemical_melting_point_lt       453
_chemical_name_systematic
;
9-[(2-Hydroxybenzylidene)amino]-11-(2-hydroxyphenyl)-10,13-diphenyl-8-oxa-
12-azoniatricyclo[7.3.1.0^2,7^]trideca-2(7),3,5-triene acetate ethanol
disolvate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.118(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5464(10)
_cell_length_b                   20.1124(15)
_cell_length_c                   14.2535(11)
_cell_measurement_reflns_used    4349
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.71
_cell_measurement_theta_min      2.51
_cell_volume                     3749.0(5)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35569
_diffrn_reflns_theta_full        26.13
_diffrn_reflns_theta_max         26.13
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.044P)²+0.8P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                4951
_reflns_number_total             7399
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2264.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229489
_cod_database_fobs_code          2229489
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
C C1 0.31447(13) 0.45725(9) 0.26034(13) 0.0241(4) Uani d . 1 . .
H H1 0.3562 0.4309 0.3162 0.029 Uiso calc R 1 . .
C C2 0.27020(13) 0.41161(8) 0.17702(13) 0.0238(4) Uani d . 1 . .
C C3 0.31983(14) 0.35414(9) 0.15984(14) 0.0286(4) Uani d . 1 . .
H H3 0.3835 0.3423 0.2031 0.034 Uiso calc R 1 . .
C C4 0.27796(14) 0.31398(9) 0.08085(15) 0.0332(5) Uani d . 1 . .
H H4 0.3128 0.2749 0.0698 0.040 Uiso calc R 1 . .
C C5 0.18468(14) 0.33100(9) 0.01773(14) 0.0308(4) Uani d . 1 . .
H H5 0.1562 0.3036 -0.0370 0.037 Uiso calc R 1 . .
C C6 0.13298(13) 0.38735(8) 0.03375(13) 0.0253(4) Uani d . 1 . .
H H6 0.0687 0.3985 -0.0089 0.030 Uiso calc R 1 . .
C C7 0.17631(13) 0.42725(8) 0.11278(12) 0.0224(4) Uani d . 1 . .
O O8 0.11919(8) 0.48161(5) 0.12638(8) 0.0223(3) Uani d . 1 . .
C C9 0.16377(13) 0.52919(8) 0.20072(12) 0.0218(4) Uani d . 1 . .
C C10 0.22947(12) 0.58026(8) 0.16205(13) 0.0229(4) Uani d . 1 . .
H H10 0.2529 0.6143 0.2143 0.027 Uiso calc R 1 . .
C C11 0.32643(12) 0.54871(8) 0.14383(12) 0.0222(4) Uani d . 1 . .
H H11 0.3046 0.5182 0.0867 0.027 Uiso calc R 1 . .
N N12 0.38139(10) 0.50797(7) 0.22941(10) 0.0226(3) Uani d . 1 . .
H H12A 0.4342 0.4854 0.2119 0.027 Uiso d R 1 . .
H H12B 0.4088 0.5347 0.2840 0.027 Uiso d R 1 . .
C C13 0.23087(12) 0.49527(8) 0.29266(12) 0.0235(4) Uani d . 1 . .
H H13 0.2660 0.5317 0.3365 0.028 Uiso calc R 1 . .
N N1 0.08334(10) 0.56563(7) 0.22658(10) 0.0232(3) Uani d . 1 . .
C C14 -0.00930(13) 0.54651(9) 0.20077(13) 0.0256(4) Uani d . 1 . .
H H14 -0.0258 0.5075 0.1623 0.031 Uiso calc R 1 . .
C C15 -0.09103(13) 0.58249(9) 0.22817(13) 0.0260(4) Uani d . 1 . .
C C16 -0.07164(14) 0.64102(10) 0.28307(14) 0.0335(5) Uani d . 1 . .
O O1 0.02500(10) 0.66495(7) 0.31689(12) 0.0508(4) Uani d . 1 . .
H H1O 0.0648 0.6343 0.2931 0.076 Uiso d R 1 . .
C C17 -0.15130(15) 0.67540(10) 0.30517(16) 0.0420(5) Uani d . 1 . .
H H17 -0.1381 0.7155 0.3416 0.050 Uiso calc R 1 . .
C C18 -0.24953(15) 0.65141(11) 0.27434(15) 0.0411(5) Uani d . 1 . .
H H18 -0.3037 0.6752 0.2899 0.049 Uiso calc R 1 . .
C C19 -0.27084(15) 0.59328(10) 0.22123(15) 0.0392(5) Uani d . 1 . .
H H19 -0.3388 0.5768 0.2012 0.047 Uiso calc R 1 . .
C C20 -0.19200(14) 0.55965(10) 0.19783(14) 0.0333(5) Uani d . 1 . .
H H20 -0.2064 0.5201 0.1603 0.040 Uiso calc R 1 . .
C C21 0.16999(12) 0.61709(8) 0.07242(13) 0.0239(4) Uani d . 1 . .
C C22 0.15273(13) 0.58968(9) -0.01999(13) 0.0264(4) Uani d . 1 . .
H H22 0.1762 0.5460 -0.0273 0.032 Uiso calc R 1 . .
C C23 0.10186(13) 0.62515(9) -0.10155(14) 0.0301(4) Uani d . 1 . .
H H23 0.0917 0.6059 -0.1642 0.036 Uiso calc R 1 . .
C C24 0.06575(14) 0.68840(10) -0.09224(15) 0.0347(5) Uani d . 1 . .
H H24 0.0309 0.7127 -0.1482 0.042 Uiso calc R 1 . .
C C25 0.08082(14) 0.71584(9) -0.00093(16) 0.0366(5) Uani d . 1 . .
H H25 0.0554 0.7591 0.0060 0.044 Uiso calc R 1 . .
C C26 0.13278(13) 0.68080(9) 0.08103(15) 0.0298(4) Uani d . 1 . .
H H26 0.1431 0.7004 0.1435 0.036 Uiso calc R 1 . .
C C27 0.39849(12) 0.59989(9) 0.12015(13) 0.0241(4) Uani d . 1 . .
C C28 0.43138(13) 0.59222(9) 0.03550(13) 0.0257(4) Uani d . 1 . .
O O2 0.39434(9) 0.54015(6) -0.02342(9) 0.0311(3) Uani d . 1 . .
H H2O 0.4183 0.5416 -0.0816 0.047 Uiso d R 1 . .
C C29 0.49980(14) 0.63804(10) 0.01430(14) 0.0340(5) Uani d . 1 . .
H H29 0.5235 0.6326 -0.0423 0.041 Uiso calc R 1 . .
C C30 0.53299(15) 0.69114(10) 0.07520(16) 0.0394(5) Uani d . 1 . .
H H30 0.5798 0.7220 0.0603 0.047 Uiso calc R 1 . .
C C31 0.49895(15) 0.70016(10) 0.15790(15) 0.0361(5) Uani d . 1 . .
H H31 0.5206 0.7376 0.1988 0.043 Uiso calc R 1 . .
C C32 0.43302(13) 0.65386(9) 0.18001(14) 0.0293(4) Uani d . 1 . .
H H32 0.4109 0.6592 0.2376 0.035 Uiso calc R 1 . .
C C33 0.17145(13) 0.45525(9) 0.35001(13) 0.0268(4) Uani d . 1 . .
C C34 0.12157(14) 0.39565(10) 0.31830(14) 0.0332(5) Uani d . 1 . .
H H34 0.1256 0.3769 0.2582 0.040 Uiso calc R 1 . .
C C35 0.06608(16) 0.36341(11) 0.37368(15) 0.0427(5) Uani d . 1 . .
H H35 0.0325 0.3227 0.3513 0.051 Uiso calc R 1 . .
C C36 0.05916(17) 0.39003(12) 0.46139(16) 0.0477(6) Uani d . 1 . .
H H36 0.0200 0.3682 0.4987 0.057 Uiso calc R 1 . .
C C37 0.10967(17) 0.44863(11) 0.49416(16) 0.0464(6) Uani d . 1 . .
H H37 0.1066 0.4667 0.5549 0.056 Uiso calc R 1 . .
C C38 0.16484(15) 0.48112(10) 0.43867(14) 0.0357(5) Uani d . 1 . .
H H38 0.1986 0.5217 0.4615 0.043 Uiso calc R 1 . .
O O5 0.46371(10) 0.57558(7) 0.39577(9) 0.0374(3) Uani d . 1 . .
H H5O 0.4207 0.5946 0.4335 0.056 Uiso d R 1 . .
C C41 0.56962(14) 0.57329(10) 0.44520(15) 0.0351(5) Uani d . 1 . .
H H41A 0.6090 0.5584 0.3995 0.042 Uiso calc R 1 . .
H H41B 0.5804 0.5405 0.4987 0.042 Uiso calc R 1 . .
C C42 0.60860(16) 0.63970(10) 0.48591(17) 0.0454(6) Uani d . 1 . .
H H42A 0.6826 0.6371 0.5146 0.068 Uiso calc R 1 . .
H H42B 0.5747 0.6526 0.5360 0.068 Uiso calc R 1 . .
H H42C 0.5941 0.6729 0.4338 0.068 Uiso calc R 1 . .
O O6 0.66244(10) 0.37980(6) 0.50427(10) 0.0369(3) Uani d . 1 . .
H H6O 0.6265 0.3937 0.4387 0.055 Uiso d R 1 . .
C C43 0.70231(18) 0.31419(11) 0.50708(16) 0.0468(6) Uani d . 1 . .
H H43A 0.7738 0.3162 0.5021 0.056 Uiso calc R 1 . .
H H43B 0.6617 0.2886 0.4508 0.056 Uiso calc R 1 . .
C C44 0.69941(17) 0.27955(11) 0.59883(16) 0.0474(6) Uani d . 1 . .
H H44A 0.7292 0.2351 0.5997 0.071 Uiso calc R 1 . .
H H44B 0.6284 0.2757 0.6024 0.071 Uiso calc R 1 . .
H H44C 0.7388 0.3051 0.6546 0.071 Uiso calc R 1 . .
C C39 0.59166(14) 0.42003(10) 0.25775(14) 0.0321(4) Uani d . 1 . .
C C40 0.69533(16) 0.39181(13) 0.25958(17) 0.0524(6) Uani d . 1 . .
H H40A 0.7006 0.3464 0.2854 0.079 Uiso calc R 1 . .
H H40B 0.7487 0.4195 0.3010 0.079 Uiso calc R 1 . .
H H40C 0.7040 0.3911 0.1934 0.079 Uiso calc R 1 . .
O O3 0.54470(9) 0.45292(6) 0.18438(9) 0.0316(3) Uani d . 1 . .
O O4 0.55567(10) 0.41052(8) 0.32869(10) 0.0459(4) 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 0.0033 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
_geom_angle_publ_flag
C2 C1 N12 . . 109.30(14) ?
C2 C1 C13 . . 111.69(14) ?
N12 C1 C13 . . 107.37(13) ?
C2 C1 H1 . . 109.5 ?
N12 C1 H1 . . 109.5 ?
C13 C1 H1 . . 109.5 ?
C3 C2 C7 . . 118.13(16) ?
C3 C2 C1 . . 122.50(16) ?
C7 C2 C1 . . 119.36(15) ?
C4 C3 C2 . . 120.99(18) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 119.63(17) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C6 C5 C4 . . 120.63(18) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C7 . . 118.99(17) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
O8 C7 C6 . . 116.05(15) ?
O8 C7 C2 . . 122.28(15) ?
C6 C7 C2 . . 121.61(16) ?
C7 O8 C9 . . 119.13(13) ?
O8 C9 N1 . . 109.09(13) ?
O8 C9 C13 . . 111.85(13) ?
N1 C9 C13 . . 108.96(13) ?
O8 C9 C10 . . 110.38(13) ?
N1 C9 C10 . . 107.26(13) ?
C13 C9 C10 . . 109.18(13) ?
C21 C10 C11 . . 110.40(14) ?
C21 C10 C9 . . 113.29(14) ?
C11 C10 C9 . . 112.37(14) ?
C21 C10 H10 . . 106.8 ?
C11 C10 H10 . . 106.8 ?
C9 C10 H10 . . 106.8 ?
N12 C11 C27 . . 109.93(13) ?
N12 C11 C10 . . 110.66(13) ?
C27 C11 C10 . . 112.63(14) ?
N12 C11 H11 . . 107.8 ?
C27 C11 H11 . . 107.8 ?
C10 C11 H11 . . 107.8 ?
C11 N12 C1 . . 113.59(13) ?
C11 N12 H12A . . 107.5 ?
C1 N12 H12A . . 108.1 ?
C11 N12 H12B . . 111.5 ?
C1 N12 H12B . . 106.5 ?
H12A N12 H12B . . 109.5 ?
C33 C13 C1 . . 115.72(14) ?
C33 C13 C9 . . 114.42(14) ?
C1 C13 C9 . . 106.41(13) ?
C33 C13 H13 . . 106.6 ?
C1 C13 H13 . . 106.6 ?
C9 C13 H13 . . 106.6 ?
C14 N1 C9 . . 121.86(15) ?
N1 C14 C15 . . 122.22(16) ?
N1 C14 H14 . . 118.9 ?
C15 C14 H14 . . 118.9 ?
C16 C15 C20 . . 118.30(17) ?
C16 C15 C14 . . 121.47(16) ?
C20 C15 C14 . . 120.21(16) ?
O1 C16 C17 . . 118.54(17) ?
O1 C16 C15 . . 121.25(16) ?
C17 C16 C15 . . 120.21(18) ?
C16 O1 H1O . . 103.3 ?
C18 C17 C16 . . 119.89(19) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C19 . . 121.22(18) ?
C17 C18 H18 . . 119.4 ?
C19 C18 H18 . . 119.4 ?
C20 C19 C18 . . 118.95(18) ?
C20 C19 H19 . . 120.5 ?
C18 C19 H19 . . 120.5 ?
C19 C20 C15 . . 121.41(18) ?
C19 C20 H20 . . 119.3 ?
C15 C20 H20 . . 119.3 ?
C22 C21 C26 . . 118.20(17) ?
C22 C21 C10 . . 121.76(15) ?
C26 C21 C10 . . 120.03(16) ?
C23 C22 C21 . . 121.00(17) ?
C23 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
C24 C23 C22 . . 120.32(19) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C25 C24 C23 . . 119.36(18) ?
C25 C24 H24 . . 120.3 ?
C23 C24 H24 . . 120.3 ?
C24 C25 C26 . . 120.58(18) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C25 C26 C21 . . 120.53(18) ?
C25 C26 H26 . . 119.7 ?
C21 C26 H26 . . 119.7 ?
C32 C27 C28 . . 119.04(16) ?
C32 C27 C11 . . 121.92(16) ?
C28 C27 C11 . . 119.03(15) ?
O2 C28 C29 . . 122.43(16) ?
O2 C28 C27 . . 118.04(15) ?
C29 C28 C27 . . 119.53(17) ?
C28 O2 H2O . . 110.8 ?
C30 C29 C28 . . 120.17(18) ?
C30 C29 H29 . . 119.9 ?
C28 C29 H29 . . 119.9 ?
C29 C30 C31 . . 120.79(18) ?
C29 C30 H30 . . 119.6 ?
C31 C30 H30 . . 119.6 ?
C32 C31 C30 . . 118.95(18) ?
C32 C31 H31 . . 120.5 ?
C30 C31 H31 . . 120.5 ?
C31 C32 C27 . . 121.48(18) ?
C31 C32 H32 . . 119.3 ?
C27 C32 H32 . . 119.3 ?
C38 C33 C34 . . 118.44(17) ?
C38 C33 C13 . . 117.35(16) ?
C34 C33 C13 . . 124.20(16) ?
C35 C34 C33 . . 120.51(18) ?
C35 C34 H34 . . 119.7 ?
C33 C34 H34 . . 119.7 ?
C34 C35 C36 . . 120.53(19) ?
C34 C35 H35 . . 119.7 ?
C36 C35 H35 . . 119.7 ?
C37 C36 C35 . . 119.38(19) ?
C37 C36 H36 . . 120.3 ?
C35 C36 H36 . . 120.3 ?
C36 C37 C38 . . 120.18(19) ?
C36 C37 H37 . . 119.9 ?
C38 C37 H37 . . 119.9 ?
C37 C38 C33 . . 120.95(19) ?
C37 C38 H38 . . 119.5 ?
C33 C38 H38 . . 119.5 ?
C41 O5 H5O . . 114.3 ?
O5 C41 C42 . . 111.77(16) ?
O5 C41 H41A . . 109.3 ?
C42 C41 H41A . . 109.3 ?
O5 C41 H41B . . 109.3 ?
C42 C41 H41B . . 109.3 ?
H41A C41 H41B . . 107.9 ?
C41 C42 H42A . . 109.5 ?
C41 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C41 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C43 O6 H6O . . 112.5 ?
O6 C43 C44 . . 111.19(17) ?
O6 C43 H43A . . 109.4 ?
C44 C43 H43A . . 109.4 ?
O6 C43 H43B . . 109.4 ?
C44 C43 H43B . . 109.4 ?
H43A C43 H43B . . 108.0 ?
C43 C44 H44A . . 109.5 ?
C43 C44 H44B . . 109.5 ?
H44A C44 H44B . . 109.5 ?
C43 C44 H44C . . 109.5 ?
H44A C44 H44C . . 109.5 ?
H44B C44 H44C . . 109.5 ?
O4 C39 O3 . . 122.28(17) ?
O4 C39 C40 . . 119.18(18) ?
O3 C39 C40 . . 118.54(17) ?
C39 C40 H40A . . 109.5 ?
C39 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
C39 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.497(2) ?
C1 N12 . 1.505(2) ?
C1 C13 . 1.533(2) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.391(2) ?
C2 C7 . 1.396(2) ?
C3 C4 . 1.382(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.389(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.382(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.383(2) ?
C6 H6 . 0.9500 ?
C7 O8 . 1.3820(19) ?
O8 C9 . 1.438(2) ?
C9 N1 . 1.439(2) ?
C9 C13 . 1.545(2) ?
C9 C10 . 1.551(2) ?
C10 C21 . 1.514(2) ?
C10 C11 . 1.541(2) ?
C10 H10 . 1.0000 ?
C11 N12 . 1.497(2) ?
C11 C27 . 1.516(2) ?
C11 H11 . 1.0000 ?
N12 H12A . 0.9347 ?
N12 H12B . 0.9381 ?
C13 C33 . 1.519(2) ?
C13 H13 . 1.0000 ?
N1 C14 . 1.272(2) ?
C14 C15 . 1.459(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.400(3) ?
C15 C20 . 1.400(3) ?
C16 O1 . 1.360(2) ?
C16 C17 . 1.385(3) ?
O1 H1O . 0.9389 ?
C17 C18 . 1.375(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.382(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.377(3) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
C21 C22 . 1.390(3) ?
C21 C26 . 1.394(2) ?
C22 C23 . 1.385(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.382(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.379(3) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.388(3) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 C32 . 1.384(2) ?
C27 C28 . 1.400(2) ?
C28 O2 . 1.354(2) ?
C28 C29 . 1.395(2) ?
O2 H2O . 0.9659 ?
C29 C30 . 1.376(3) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.385(3) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.382(3) ?
C31 H31 . 0.9500 ?
C32 H32 . 0.9500 ?
C33 C38 . 1.391(3) ?
C33 C34 . 1.392(3) ?
C34 C35 . 1.385(3) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.385(3) ?
C35 H35 . 0.9500 ?
C36 C37 . 1.382(3) ?
C36 H36 . 0.9500 ?
C37 C38 . 1.386(3) ?
C37 H37 . 0.9500 ?
C38 H38 . 0.9500 ?
O5 C41 . 1.425(2) ?
O5 H5O . 0.9692 ?
C41 C42 . 1.497(3) ?
C41 H41A . 0.9900 ?
C41 H41B . 0.9900 ?
C42 H42A . 0.9800 ?
C42 H42B . 0.9800 ?
C42 H42C . 0.9800 ?
O6 C43 . 1.422(2) ?
O6 H6O . 0.9752 ?
C43 C44 . 1.491(3) ?
C43 H43A . 0.9900 ?
C43 H43B . 0.9900 ?
C44 H44A . 0.9800 ?
C44 H44B . 0.9800 ?
C44 H44C . 0.9800 ?
C39 O4 . 1.246(2) ?
C39 O3 . 1.261(2) ?
C39 C40 . 1.509(3) ?
C40 H40A . 0.9800 ?
C40 H40B . 0.9800 ?
C40 H40C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1O N1 . 0.94 1.73 2.608(2) 154 yes
O2 H2O O3 3_665 0.97 1.67 2.637(2) 177 yes
O5 H5O O6 3_666 0.97 1.69 2.651(2) 174 yes
O6 H6O O4 . 0.98 1.65 2.617(2) 173 yes
N12 H12A O3 . 0.93 1.77 2.697(2) 172 yes
N12 H12B O5 . 0.94 1.77 2.709(2) 173 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N12 C1 C2 C3 . . . . 88.45(19) ?
C13 C1 C2 C3 . . . . -152.89(16) ?
N12 C1 C2 C7 . . . . -90.60(18) ?
C13 C1 C2 C7 . . . . 28.1(2) ?
C7 C2 C3 C4 . . . . 0.7(3) ?
C1 C2 C3 C4 . . . . -178.39(16) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
C3 C4 C5 C6 . . . . -0.6(3) ?
C4 C5 C6 C7 . . . . 1.1(3) ?
C5 C6 C7 O8 . . . . -178.01(15) ?
C5 C6 C7 C2 . . . . -0.6(3) ?
C3 C2 C7 O8 . . . . 176.98(15) ?
C1 C2 C7 O8 . . . . -3.9(2) ?
C3 C2 C7 C6 . . . . -0.2(2) ?
C1 C2 C7 C6 . . . . 178.88(15) ?
C6 C7 O8 C9 . . . . -173.46(14) ?
C2 C7 O8 C9 . . . . 9.2(2) ?
C7 O8 C9 N1 . . . . -158.67(13) ?
C7 O8 C9 C13 . . . . -38.05(18) ?
C7 O8 C9 C10 . . . . 83.72(17) ?
O8 C9 C10 C21 . . . . 57.51(18) ?
N1 C9 C10 C21 . . . . -61.23(18) ?
C13 C9 C10 C21 . . . . -179.16(14) ?
O8 C9 C10 C11 . . . . -68.47(17) ?
N1 C9 C10 C11 . . . . 172.79(13) ?
C13 C9 C10 C11 . . . . 54.86(18) ?
C21 C10 C11 N12 . . . . -175.72(13) ?
C9 C10 C11 N12 . . . . -48.19(18) ?
C21 C10 C11 C27 . . . . 60.78(18) ?
C9 C10 C11 C27 . . . . -171.69(14) ?
C27 C11 N12 C1 . . . . 177.98(13) ?
C10 C11 N12 C1 . . . . 52.95(18) ?
C2 C1 N12 C11 . . . . 58.31(18) ?
C13 C1 N12 C11 . . . . -63.00(17) ?
C2 C1 C13 C33 . . . . 74.96(19) ?
N12 C1 C13 C33 . . . . -165.24(14) ?
C2 C1 C13 C9 . . . . -53.37(18) ?
N12 C1 C13 C9 . . . . 66.44(16) ?
O8 C9 C13 C33 . . . . -69.97(18) ?
N1 C9 C13 C33 . . . . 50.72(19) ?
C10 C9 C13 C33 . . . . 167.57(14) ?
O8 C9 C13 C1 . . . . 59.12(16) ?
N1 C9 C13 C1 . . . . 179.81(13) ?
C10 C9 C13 C1 . . . . -63.34(16) ?
O8 C9 N1 C14 . . . . 13.6(2) ?
C13 C9 N1 C14 . . . . -108.74(18) ?
C10 C9 N1 C14 . . . . 133.19(16) ?
C9 N1 C14 C15 . . . . 178.85(16) ?
N1 C14 C15 C16 . . . . 1.3(3) ?
N1 C14 C15 C20 . . . . 179.83(17) ?
C20 C15 C16 O1 . . . . 178.30(18) ?
C14 C15 C16 O1 . . . . -3.1(3) ?
C20 C15 C16 C17 . . . . -0.8(3) ?
C14 C15 C16 C17 . . . . 177.75(18) ?
O1 C16 C17 C18 . . . . -178.2(2) ?
C15 C16 C17 C18 . . . . 1.0(3) ?
C16 C17 C18 C19 . . . . -0.1(3) ?
C17 C18 C19 C20 . . . . -1.0(3) ?
C18 C19 C20 C15 . . . . 1.2(3) ?
C16 C15 C20 C19 . . . . -0.3(3) ?
C14 C15 C20 C19 . . . . -178.86(18) ?
C11 C10 C21 C22 . . . . 44.7(2) ?
C9 C10 C21 C22 . . . . -82.32(19) ?
C11 C10 C21 C26 . . . . -133.91(16) ?
C9 C10 C21 C26 . . . . 99.07(18) ?
C26 C21 C22 C23 . . . . 1.3(2) ?
C10 C21 C22 C23 . . . . -177.29(16) ?
C21 C22 C23 C24 . . . . -1.0(3) ?
C22 C23 C24 C25 . . . . 0.0(3) ?
C23 C24 C25 C26 . . . . 0.8(3) ?
C24 C25 C26 C21 . . . . -0.4(3) ?
C22 C21 C26 C25 . . . . -0.6(3) ?
C10 C21 C26 C25 . . . . 178.05(16) ?
N12 C11 C27 C32 . . . . -70.3(2) ?
C10 C11 C27 C32 . . . . 53.6(2) ?
N12 C11 C27 C28 . . . . 109.50(17) ?
C10 C11 C27 C28 . . . . -126.60(17) ?
C32 C27 C28 O2 . . . . -178.12(15) ?
C11 C27 C28 O2 . . . . 2.1(2) ?
C32 C27 C28 C29 . . . . 1.5(3) ?
C11 C27 C28 C29 . . . . -178.31(16) ?
O2 C28 C29 C30 . . . . 178.19(17) ?
C27 C28 C29 C30 . . . . -1.4(3) ?
C28 C29 C30 C31 . . . . -0.3(3) ?
C29 C30 C31 C32 . . . . 1.8(3) ?
C30 C31 C32 C27 . . . . -1.7(3) ?
C28 C27 C32 C31 . . . . 0.1(3) ?
C11 C27 C32 C31 . . . . 179.82(17) ?
C1 C13 C33 C38 . . . . 127.54(18) ?
C9 C13 C33 C38 . . . . -108.19(18) ?
C1 C13 C33 C34 . . . . -54.1(2) ?
C9 C13 C33 C34 . . . . 70.1(2) ?
C38 C33 C34 C35 . . . . 0.5(3) ?
C13 C33 C34 C35 . . . . -177.78(18) ?
C33 C34 C35 C36 . . . . 0.1(3) ?
C34 C35 C36 C37 . . . . -1.1(4) ?
C35 C36 C37 C38 . . . . 1.4(4) ?
C36 C37 C38 C33 . . . . -0.7(3) ?
C34 C33 C38 C37 . . . . -0.2(3) ?
C13 C33 C38 C37 . . . . 178.19(19) ?
