#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:13:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180382 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/51/7205147.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7205147
loop_
_publ_author_name
'Wu, De-Hong'
'Ge, Jia-Zhen'
'Cai, Hong-Lin'
'Zhang, Wen'
'Xiong, Ren-Gen'
_publ_section_title
;
 Organic salt of hydrogen l-tartaric acid: a novel
 wide-temperature-range ferroelectrics with a reversible phase
 transition
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              319
_journal_paper_doi               10.1039/c0ce00109k
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C8 H12 N, C4 H5 O6'
_chemical_formula_sum            'C12 H17 N O6'
_chemical_formula_weight         271.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           1
_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           SHELXL-97
_cell_angle_alpha                95.338(2)
_cell_angle_beta                 91.9500(10)
_cell_angle_gamma                107.9160(10)
_cell_formula_units_Z            4
_cell_length_a                   7.4606(12)
_cell_length_b                   11.9298(18)
_cell_length_c                   14.8726(9)
_cell_measurement_reflns_used    3664
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5087
_cell_measurement_theta_min      3.1892
_cell_volume                     1251.3(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13753
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         5681
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0386
_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)+(0.0508P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                4661
_reflns_number_total             5681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00109K.TXT
_cod_data_source_block           wudh_LTP(123K)
_cod_database_code               7205147
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6261(5) 0.2244(3) 0.2634(2) 0.0367(8) Uani 1 1 d . . .
H1A H 0.6826 0.1708 0.2881 0.055 Uiso 1 1 calc R . .
H1B H 0.6321 0.2179 0.1988 0.055 Uiso 1 1 calc R . .
H1C H 0.4965 0.2048 0.2781 0.055 Uiso 1 1 calc R . .
C2 C 0.7309(4) 0.3492(3) 0.3026(2) 0.0277(7) Uani 1 1 d . . .
H2A H 0.6671 0.4014 0.2797 0.033 Uiso 1 1 calc R . .
H2B H 0.8564 0.3709 0.2803 0.033 Uiso 1 1 calc R . .
C3 C 0.7510(4) 0.3724(3) 0.4057(2) 0.0211(6) Uani 1 1 d . . .
C4 C 0.6812(4) 0.2836(3) 0.4610(2) 0.0232(7) Uani 1 1 d . . .
H4 H 0.6197 0.2067 0.4348 0.028 Uiso 1 1 calc R . .
C5 C 0.7013(4) 0.3072(3) 0.5550(2) 0.0195(6) Uani 1 1 d . . .
H5 H 0.6557 0.2466 0.5913 0.023 Uiso 1 1 calc R . .
C6 C 0.7897(4) 0.4217(2) 0.59314(18) 0.0141(5) Uani 1 1 d . . .
C7 C 0.8642(4) 0.5125(3) 0.5402(2) 0.0213(6) Uani 1 1 d . . .
H7 H 0.9255 0.5892 0.5667 0.026 Uiso 1 1 calc R . .
C8 C 0.8451(4) 0.4862(3) 0.4466(2) 0.0223(6) Uani 1 1 d . . .
H8 H 0.8964 0.5462 0.4105 0.027 Uiso 1 1 calc R . .
C9 C 0.3420(4) 0.4726(3) 0.5094(2) 0.0272(7) Uani 1 1 d . . .
H9A H 0.4639 0.4949 0.4849 0.041 Uiso 1 1 calc R . .
H9B H 0.3571 0.4715 0.5736 0.041 Uiso 1 1 calc R . .
H9C H 0.2785 0.5288 0.4970 0.041 Uiso 1 1 calc R . .
C10 C 0.2258(4) 0.3499(3) 0.46607(19) 0.0224(7) Uani 1 1 d . . .
H10A H 0.2833 0.2928 0.4856 0.027 Uiso 1 1 calc R . .
H10B H 0.1006 0.3309 0.4886 0.027 Uiso 1 1 calc R . .
C11 C 0.2056(4) 0.3352(3) 0.36363(19) 0.0179(6) Uani 1 1 d . . .
C12 C 0.1207(4) 0.2230(3) 0.3180(2) 0.0202(6) Uani 1 1 d . . .
H12 H 0.0762 0.1590 0.3513 0.024 Uiso 1 1 calc R . .
C13 C 0.1004(4) 0.2037(2) 0.2244(2) 0.0190(6) Uani 1 1 d . . .
H13 H 0.0440 0.1277 0.1953 0.023 Uiso 1 1 calc R . .
C14 C 0.1653(4) 0.2989(2) 0.17460(19) 0.0158(6) Uani 1 1 d . . .
C15 C 0.2480(4) 0.4115(2) 0.21754(18) 0.0168(6) Uani 1 1 d . . .
H15 H 0.2892 0.4753 0.1838 0.020 Uiso 1 1 calc R . .
C16 C 0.2698(4) 0.4294(2) 0.31179(18) 0.0180(6) Uani 1 1 d . . .
H16 H 0.3281 0.5054 0.3405 0.022 Uiso 1 1 calc R . .
C17 C 0.7837(5) 0.9684(3) 0.5095(2) 0.0297(8) Uani 1 1 d . . .
H17A H 0.8889 1.0236 0.4855 0.044 Uiso 1 1 calc R . .
H17B H 0.8074 0.9707 0.5736 0.044 Uiso 1 1 calc R . .
H17C H 0.6715 0.9894 0.4978 0.044 Uiso 1 1 calc R . .
C18 C 0.7575(4) 0.8441(3) 0.4646(2) 0.0254(7) Uani 1 1 d . . .
H18A H 0.8673 0.8215 0.4815 0.031 Uiso 1 1 calc R . .
H18B H 0.6489 0.7898 0.4884 0.031 Uiso 1 1 calc R . .
C19 C 0.7295(4) 0.8287(3) 0.36210(19) 0.0189(6) Uani 1 1 d . . .
C20 C 0.7019(4) 0.7176(3) 0.3148(2) 0.0212(6) Uani 1 1 d . . .
H20 H 0.6984 0.6537 0.3468 0.025 Uiso 1 1 calc R . .
C21 C 0.6793(4) 0.7000(3) 0.2205(2) 0.0187(6) Uani 1 1 d . . .
H21 H 0.6615 0.6255 0.1897 0.022 Uiso 1 1 calc R . .
C22 C 0.6840(4) 0.7957(2) 0.17348(17) 0.0130(5) Uani 1 1 d . . .
C23 C 0.7102(4) 0.9066(2) 0.21828(18) 0.0171(6) Uani 1 1 d . . .
H23 H 0.7127 0.9702 0.1860 0.021 Uiso 1 1 calc R . .
C24 C 0.7327(4) 0.9223(3) 0.31242(19) 0.0196(6) Uani 1 1 d . . .
H24 H 0.7502 0.9970 0.3427 0.023 Uiso 1 1 calc R . .
C25 C 0.2025(5) 0.7311(3) 0.2598(2) 0.0339(8) Uani 1 1 d . . .
H25A H 0.3066 0.7084 0.2828 0.051 Uiso 1 1 calc R . .
H25B H 0.2035 0.7288 0.1952 0.051 Uiso 1 1 calc R . .
H25C H 0.0862 0.6772 0.2757 0.051 Uiso 1 1 calc R . .
C26 C 0.2203(4) 0.8551(3) 0.30040(19) 0.0271(7) Uani 1 1 d . . .
H26A H 0.3277 0.9097 0.2760 0.032 Uiso 1 1 calc R . .
H26B H 0.1086 0.8738 0.2806 0.032 Uiso 1 1 calc R . .
C27 C 0.2439(4) 0.8774(3) 0.40227(19) 0.0200(6) Uani 1 1 d . . .
C28 C 0.2404(4) 0.7877(3) 0.4566(2) 0.0200(6) Uani 1 1 d . . .
H28 H 0.2240 0.7115 0.4295 0.024 Uiso 1 1 calc R . .
C29 C 0.2610(4) 0.8097(2) 0.5506(2) 0.0180(6) Uani 1 1 d . . .
H29 H 0.2582 0.7488 0.5859 0.022 Uiso 1 1 calc R . .
C30 C 0.2856(4) 0.9230(3) 0.59057(19) 0.0172(6) Uani 1 1 d . . .
C31 C 0.2912(4) 1.0137(3) 0.5387(2) 0.0203(6) Uani 1 1 d . . .
H31 H 0.3079 1.0898 0.5661 0.024 Uiso 1 1 calc R . .
C32 C 0.2715(4) 0.9902(3) 0.4450(2) 0.0229(6) Uani 1 1 d . . .
H32 H 0.2770 1.0518 0.4101 0.028 Uiso 1 1 calc R . .
C33 C 0.6590(3) 0.0750(2) -0.01222(18) 0.0145(5) Uani 1 1 d . . .
C34 C 0.4511(3) 0.0705(2) -0.02666(18) 0.0140(5) Uani 1 1 d . . .
H34 H 0.4215 0.0729 -0.0910 0.017 Uiso 1 1 calc R . .
C35 C 0.3210(3) -0.0429(2) 0.00407(18) 0.0148(5) Uani 1 1 d . . .
H35 H 0.3162 -0.1097 -0.0406 0.018 Uiso 1 1 calc R . .
C36 C 0.1229(4) -0.0356(2) 0.01292(19) 0.0151(5) Uani 1 1 d . . .
C37 C 1.1768(4) 0.5752(2) -0.01433(18) 0.0151(5) Uani 1 1 d . . .
C38 C 0.9693(3) 0.5728(2) -0.02726(17) 0.0129(5) Uani 1 1 d . . .
H38 H 0.9382 0.5761 -0.0913 0.016 Uiso 1 1 calc R . .
C39 C 0.8400(3) 0.4573(2) 0.00343(17) 0.0146(5) Uani 1 1 d . . .
H39 H 0.8378 0.3912 -0.0414 0.018 Uiso 1 1 calc R . .
C40 C 0.6392(3) 0.4614(2) 0.01135(18) 0.0130(5) Uani 1 1 d . . .
C41 C 0.3471(4) 0.2688(2) 0.74033(17) 0.0143(5) Uani 1 1 d . . .
C42 C 0.1331(3) 0.2395(2) 0.72236(18) 0.0138(5) Uani 1 1 d . . .
H42 H 0.0917 0.1828 0.6679 0.017 Uiso 1 1 calc R . .
C43 C 0.0297(3) 0.1841(2) 0.80288(17) 0.0125(5) Uani 1 1 d . . .
H43 H 0.0506 0.1075 0.8068 0.015 Uiso 1 1 calc R . .
C44 C -0.1814(3) 0.1611(2) 0.77902(17) 0.0129(5) Uani 1 1 d . . .
C45 C 0.8511(3) 0.7692(2) 0.74013(17) 0.0130(5) Uani 1 1 d . . .
C46 C 0.6377(3) 0.7387(2) 0.72176(17) 0.0128(5) Uani 1 1 d . . .
H46 H 0.5976 0.6820 0.6673 0.015 Uiso 1 1 calc R . .
C47 C 0.5327(3) 0.6827(2) 0.80221(17) 0.0140(5) Uani 1 1 d . . .
H47 H 0.5522 0.6057 0.8061 0.017 Uiso 1 1 calc R . .
C48 C 0.3233(3) 0.6619(2) 0.77772(17) 0.0120(5) Uani 1 1 d . . .
N1 N 0.8074(3) 0.4465(2) 0.69189(15) 0.0159(5) Uani 1 1 d . . .
H1D H 0.6953 0.4161 0.7139 0.024 Uiso 1 1 calc R . .
H1E H 0.8486 0.5245 0.7072 0.024 Uiso 1 1 calc R . .
H1F H 0.8891 0.4140 0.7146 0.024 Uiso 1 1 calc R . .
N2 N 0.1452(3) 0.2791(2) 0.07547(14) 0.0140(5) Uani 1 1 d . . .
H2C H 0.2295 0.2454 0.0555 0.021 Uiso 1 1 calc R . .
H2D H 0.1645 0.3482 0.0531 0.021 Uiso 1 1 calc R . .
H2E H 0.0294 0.2318 0.0577 0.021 Uiso 1 1 calc R . .
N3 N 0.6577(3) 0.7782(2) 0.07437(15) 0.0150(5) Uani 1 1 d . . .
H3A H 0.7433 0.7473 0.0519 0.023 Uiso 1 1 calc R . .
H3B H 0.6713 0.8476 0.0534 0.023 Uiso 1 1 calc R . .
H3C H 0.5424 0.7291 0.0577 0.023 Uiso 1 1 calc R . .
N4 N 0.3056(3) 0.94548(19) 0.68955(14) 0.0127(4) Uani 1 1 d . . .
H4A H 0.1945 0.9134 0.7120 0.019 Uiso 1 1 calc R . .
H4B H 0.3451 1.0233 0.7059 0.019 Uiso 1 1 calc R . .
H4C H 0.3892 0.9134 0.7109 0.019 Uiso 1 1 calc R . .
O1 O 0.7033(3) -0.01076(17) -0.05230(14) 0.0211(5) Uani 1 1 d . . .
O2 O 0.7654(3) 0.16009(17) 0.03787(13) 0.0199(4) Uani 1 1 d . . .
O3 O 0.4258(2) 0.17135(15) 0.02456(13) 0.0183(4) Uani 1 1 d . . .
H3 H 0.5247 0.2093 0.0536 0.027 Uiso 1 1 calc R . .
O4 O 0.3920(3) -0.06247(18) 0.08891(13) 0.0217(4) Uani 1 1 d . . .
H4D H 0.3131 -0.0646 0.1263 0.033 Uiso 1 1 calc R . .
O5 O 0.0469(3) -0.04971(17) 0.08369(13) 0.0243(5) Uani 1 1 d . . .
O6 O 0.0477(2) -0.01338(18) -0.06121(12) 0.0211(4) Uani 1 1 d . . .
H6 H -0.0556 -0.0056 -0.0515 0.032 Uiso 1 1 calc R . .
O7 O 1.2210(3) 0.49098(17) -0.05576(14) 0.0234(5) Uani 1 1 d . . .
O8 O 1.2818(3) 0.65864(16) 0.03757(13) 0.0186(4) Uani 1 1 d . . .
O9 O 0.9442(2) 0.67194(16) 0.02531(13) 0.0179(4) Uani 1 1 d . . .
H9 H 1.0438 0.7101 0.0537 0.027 Uiso 1 1 calc R . .
O10 O 0.9134(3) 0.43882(17) 0.08738(13) 0.0207(4) Uani 1 1 d . . .
H10 H 0.8294 0.4246 0.1228 0.031 Uiso 1 1 calc R . .
O11 O 0.5671(2) 0.49049(18) -0.06079(12) 0.0212(4) Uani 1 1 d . . .
H11 H 0.4571 0.4869 -0.0536 0.032 Uiso 1 1 calc R . .
O12 O 0.5597(3) 0.43898(17) 0.08039(12) 0.0225(4) Uani 1 1 d . . .
O13 O 0.4081(2) 0.18406(16) 0.75576(13) 0.0187(4) Uani 1 1 d . . .
O14 O 0.4435(2) 0.37307(15) 0.73694(13) 0.0179(4) Uani 1 1 d . . .
O15 O 0.0882(2) 0.34318(16) 0.70845(13) 0.0177(4) Uani 1 1 d . . .
H15A H 0.1844 0.4004 0.7161 0.027 Uiso 1 1 calc R . .
O16 O 0.0976(2) 0.25485(15) 0.88515(11) 0.0162(4) Uani 1 1 d . . .
H16A H 0.1041 0.3236 0.8793 0.024 Uiso 1 1 calc R . .
O17 O -0.2687(3) 0.08168(17) 0.72272(13) 0.0198(4) Uani 1 1 d . . .
O18 O -0.2517(2) 0.23852(16) 0.82090(13) 0.0160(4) Uani 1 1 d . . .
H18 H -0.3644 0.2211 0.8057 0.024 Uiso 1 1 calc R . .
O19 O 0.9128(2) 0.68509(16) 0.75635(13) 0.0192(4) Uani 1 1 d . . .
O20 O 0.9471(2) 0.87324(16) 0.73548(13) 0.0183(4) Uani 1 1 d . . .
O21 O 0.5901(2) 0.84175(16) 0.70776(13) 0.0187(4) Uani 1 1 d . . .
H21A H 0.6865 0.8987 0.7112 0.028 Uiso 1 1 calc R . .
O22 O 0.6011(2) 0.75384(15) 0.88415(12) 0.0167(4) Uani 1 1 d . . .
H22 H 0.5979 0.8212 0.8796 0.025 Uiso 1 1 calc R . .
O23 O 0.2370(2) 0.58372(16) 0.71908(13) 0.0175(4) Uani 1 1 d . . .
O24 O 0.2513(3) 0.73689(16) 0.82086(13) 0.0176(4) Uani 1 1 d . . .
H24A H 0.1381 0.7184 0.8062 0.026 Uiso 1 1 calc R . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 116.3(3) . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
C3 C2 H2B 108.2 . . ?
H2A C2 H2B 107.4 . . ?
C4 C3 C8 118.1(3) . . ?
C4 C3 C2 122.5(3) . . ?
C8 C3 C2 119.4(3) . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 N1 118.8(2) . . ?
C7 C6 N1 119.8(2) . . ?
C6 C7 C8 118.4(3) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C7 C8 C3 121.7(3) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C9 115.4(3) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C16 117.6(3) . . ?
C12 C11 C10 119.3(3) . . ?
C16 C11 C10 123.0(2) . . ?
C13 C12 C11 122.0(3) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 N2 120.1(2) . . ?
C13 C14 N2 119.5(2) . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.9(3) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C17 115.4(3) . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C17 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C24 C19 C20 117.9(3) . . ?
C24 C19 C18 122.4(3) . . ?
C20 C19 C18 119.7(3) . . ?
C19 C20 C21 121.5(3) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 N3 119.5(2) . . ?
C21 C22 N3 119.4(2) . . ?
C22 C23 C24 119.2(3) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C19 C24 C23 121.4(3) . . ?
C19 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C25 116.2(3) . . ?
C27 C26 H26A 108.2 . . ?
C25 C26 H26A 108.2 . . ?
C27 C26 H26B 108.2 . . ?
C25 C26 H26B 108.2 . . ?
H26A C26 H26B 107.4 . . ?
C32 C27 C28 117.6(3) . . ?
C32 C27 C26 120.1(3) . . ?
C28 C27 C26 122.3(3) . . ?
C29 C28 C27 121.5(3) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C30 C29 C28 119.0(3) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C31 C30 C29 120.8(3) . . ?
C31 C30 N4 120.3(3) . . ?
C29 C30 N4 118.9(3) . . ?
C30 C31 C32 119.3(3) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 H31 120.4 . . ?
C27 C32 C31 121.7(3) . . ?
C27 C32 H32 119.2 . . ?
C31 C32 H32 119.2 . . ?
O2 C33 O1 126.5(2) . . ?
O2 C33 C34 117.3(2) . . ?
O1 C33 C34 116.2(2) . . ?
O3 C34 C35 109.9(2) . . ?
O3 C34 C33 108.6(2) . . ?
C35 C34 C33 110.2(2) . . ?
O3 C34 H34 109.4 . . ?
C35 C34 H34 109.4 . . ?
C33 C34 H34 109.4 . . ?
O4 C35 C36 109.1(2) . . ?
O4 C35 C34 109.8(2) . . ?
C36 C35 C34 111.0(2) . . ?
O4 C35 H35 109.0 . . ?
C36 C35 H35 109.0 . . ?
C34 C35 H35 109.0 . . ?
O5 C36 O6 125.3(2) . . ?
O5 C36 C35 121.1(2) . . ?
O6 C36 C35 113.7(2) . . ?
O8 C37 O7 126.8(2) . . ?
O8 C37 C38 116.1(2) . . ?
O7 C37 C38 117.0(2) . . ?
O9 C38 C39 109.8(2) . . ?
O9 C38 C37 109.4(2) . . ?
C39 C38 C37 109.1(2) . . ?
O9 C38 H38 109.5 . . ?
C39 C38 H38 109.5 . . ?
C37 C38 H38 109.5 . . ?
O10 C39 C40 110.1(2) . . ?
O10 C39 C38 109.2(2) . . ?
C40 C39 C38 111.3(2) . . ?
O10 C39 H39 108.7 . . ?
C40 C39 H39 108.7 . . ?
C38 C39 H39 108.7 . . ?
O12 C40 O11 125.5(2) . . ?
O12 C40 C39 120.4(2) . . ?
O11 C40 C39 114.1(2) . . ?
O14 C41 O13 126.4(2) . . ?
O14 C41 C42 116.5(2) . . ?
O13 C41 C42 117.1(2) . . ?
O15 C42 C41 110.0(2) . . ?
O15 C42 C43 109.5(2) . . ?
C41 C42 C43 110.2(2) . . ?
O15 C42 H42 109.0 . . ?
C41 C42 H42 109.0 . . ?
C43 C42 H42 109.0 . . ?
O16 C43 C44 114.1(2) . . ?
O16 C43 C42 112.1(2) . . ?
C44 C43 C42 106.0(2) . . ?
O16 C43 H43 108.1 . . ?
C44 C43 H43 108.1 . . ?
C42 C43 H43 108.1 . . ?
O17 C44 O18 124.4(2) . . ?
O17 C44 C43 121.3(2) . . ?
O18 C44 C43 114.2(2) . . ?
O20 C45 O19 126.3(2) . . ?
O20 C45 C46 116.8(2) . . ?
O19 C45 C46 116.9(2) . . ?
O21 C46 C45 110.2(2) . . ?
O21 C46 C47 109.0(2) . . ?
C45 C46 C47 110.6(2) . . ?
O21 C46 H46 109.0 . . ?
C45 C46 H46 109.0 . . ?
C47 C46 H46 109.0 . . ?
O22 C47 C48 114.1(2) . . ?
O22 C47 C46 111.6(2) . . ?
C48 C47 C46 105.5(2) . . ?
O22 C47 H47 108.5 . . ?
C48 C47 H47 108.5 . . ?
C46 C47 H47 108.5 . . ?
O23 C48 O24 124.3(2) . . ?
O23 C48 C47 120.6(2) . . ?
O24 C48 C47 115.0(2) . . ?
C6 N1 H1D 109.5 . . ?
C6 N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C6 N1 H1F 109.5 . . ?
H1D N1 H1F 109.5 . . ?
H1E N1 H1F 109.5 . . ?
C14 N2 H2C 109.5 . . ?
C14 N2 H2D 109.5 . . ?
H2C N2 H2D 109.5 . . ?
C14 N2 H2E 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?
C22 N3 H3A 109.5 . . ?
C22 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C22 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C30 N4 H4A 109.5 . . ?
C30 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C30 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C34 O3 H3 109.5 . . ?
C35 O4 H4D 109.5 . . ?
C36 O6 H6 109.5 . . ?
C38 O9 H9 109.5 . . ?
C39 O10 H10 109.5 . . ?
C40 O11 H11 109.5 . . ?
C42 O15 H15A 109.5 . . ?
C43 O16 H16A 109.5 . . ?
C44 O18 H18 109.5 . . ?
C46 O21 H21A 109.5 . . ?
C47 O22 H22 109.5 . . ?
C48 O24 H24A 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.504(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.526(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.386(4) . ?
C3 C8 1.392(4) . ?
C4 C5 1.394(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 N1 1.464(3) . ?
C7 C8 1.391(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.522(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.514(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.390(4) . ?
C11 C16 1.394(4) . ?
C12 C13 1.386(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(4) . ?
C14 N2 1.466(3) . ?
C15 C16 1.395(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.521(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.517(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.390(4) . ?
C19 C20 1.394(4) . ?
C20 C21 1.396(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(3) . ?
C22 N3 1.467(3) . ?
C23 C24 1.393(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.510(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.508(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C32 1.386(4) . ?
C27 C28 1.394(4) . ?
C28 C29 1.392(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.380(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.378(4) . ?
C30 N4 1.466(3) . ?
C31 C32 1.388(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 O2 1.241(3) . ?
C33 O1 1.272(3) . ?
C33 C34 1.542(3) . ?
C34 O3 1.430(3) . ?
C34 C35 1.522(3) . ?
C34 H34 0.9800 . ?
C35 O4 1.419(3) . ?
C35 C36 1.517(3) . ?
C35 H35 0.9800 . ?
C36 O5 1.214(3) . ?
C36 O6 1.305(3) . ?
C37 O8 1.239(3) . ?
C37 O7 1.265(3) . ?
C37 C38 1.545(3) . ?
C38 O9 1.421(3) . ?
C38 C39 1.538(3) . ?
C38 H38 0.9800 . ?
C39 O10 1.410(3) . ?
C39 C40 1.522(3) . ?
C39 H39 0.9800 . ?
C40 O12 1.214(3) . ?
C40 O11 1.306(3) . ?
C41 O14 1.238(3) . ?
C41 O13 1.265(3) . ?
C41 C42 1.534(3) . ?
C42 O15 1.408(3) . ?
C42 C43 1.537(3) . ?
C42 H42 0.9800 . ?
C43 O16 1.403(3) . ?
C43 C44 1.536(3) . ?
C43 H43 0.9800 . ?
C44 O17 1.208(3) . ?
C44 O18 1.315(3) . ?
C45 O20 1.237(3) . ?
C45 O19 1.265(3) . ?
C45 C46 1.529(3) . ?
C46 O21 1.411(3) . ?
C46 C47 1.543(3) . ?
C46 H46 0.9800 . ?
C47 O22 1.401(3) . ?
C47 C48 1.530(3) . ?
C47 H47 0.9800 . ?
C48 O23 1.219(3) . ?
C48 O24 1.309(3) . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
N1 H1F 0.8900 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
O3 H3 0.8200 . ?
O4 H4D 0.8200 . ?
O6 H6 0.8200 . ?
O9 H9 0.8200 . ?
O10 H10 0.8200 . ?
O11 H11 0.8200 . ?
O15 H15A 0.8200 . ?
O16 H16A 0.8200 . ?
O18 H18 0.8200 . ?
O21 H21A 0.8200 . ?
O22 H22 0.8200 . ?
O24 H24A 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1D O14 0.89 1.84 2.712(3) 165.3 .
N1 H1E O19 0.89 1.89 2.775(3) 170.7 .
N1 H1F O15 0.89 1.92 2.753(3) 154.6 1_655
N2 H2C O3 0.89 1.98 2.862(3) 174.0 .
N2 H2D O7 0.89 2.41 3.260(3) 159.5 1_455
N2 H2D O10 0.89 2.48 2.939(3) 112.6 1_455
N2 H2E O2 0.89 1.89 2.762(3) 165.7 1_455
N3 H3A O9 0.89 2.00 2.883(3) 169.2 .
N3 H3B O1 0.89 2.38 3.225(3) 159.3 1_565
N3 H3C O8 0.89 1.87 2.736(3) 165.0 1_455
N4 H4A O20 0.89 1.81 2.679(3) 163.6 1_455
N4 H4B O13 0.89 1.90 2.783(3) 171.6 1_565
N4 H4C O21 0.89 1.94 2.784(3) 157.6 .
O3 H3 O2 0.82 2.07 2.580(3) 120.3 .
O4 H4D O5 0.82 2.13 2.625(3) 118.9 .
O6 H6 O1 0.82 1.78 2.587(3) 167.5 1_455
O9 H9 O8 0.82 2.06 2.573(3) 120.0 .
O10 H10 O12 0.82 2.15 2.638(3) 118.1 .
O11 H11 O7 0.82 1.78 2.588(3) 170.0 1_455
O15 H15A O14 0.82 2.08 2.578(2) 119.3 .
O15 H15A O23 0.82 2.10 2.727(3) 133.7 .
O16 H16A O7 0.82 2.05 2.728(3) 140.2 1_456
O18 H18 O13 0.82 1.74 2.551(2) 170.8 1_455
O21 H21A O20 0.82 2.08 2.586(2) 119.3 .
O21 H21A O17 0.82 2.09 2.713(3) 132.3 1_665
O22 H22 O1 0.82 2.06 2.739(3) 139.2 1_566
O24 H24A O19 0.82 1.73 2.538(3) 169.8 1_455
O16 H16A O15 0.82 2.58 2.927(2) 107.4 .
O22 H22 O21 0.82 2.59 2.922(3) 105.8 .
C13 H13 O5 0.93 2.57 3.420(3) 151.9 .
C21 H21 O12 0.93 2.52 3.434(3) 165.7 .
C25 H25B O8 0.96 2.56 3.455(4) 154.9 1_455
C35 H35 O24 0.98 2.55 3.511(3) 166.0 1_544
C39 H39 O18 0.98 2.53 3.480(3) 162.0 1_654
C43 H43 O6 0.98 2.54 3.274(3) 131.7 1_556
C47 H47 O11 0.98 2.53 3.267(3) 131.8 1_556
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C8 -179.4(3) . . . . ?
C8 C3 C4 C5 1.0(4) . . . . ?
C2 C3 C4 C5 -179.9(2) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C7 -2.2(4) . . . . ?
C4 C5 C6 N1 178.9(2) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
N1 C6 C7 C8 -180.0(2) . . . . ?
C6 C7 C8 C3 1.1(4) . . . . ?
C4 C3 C8 C7 -2.1(4) . . . . ?
C2 C3 C8 C7 178.8(2) . . . . ?
C9 C10 C11 C12 172.6(3) . . . . ?
C9 C10 C11 C16 -6.9(4) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C10 C11 C12 C13 -179.1(3) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C12 C13 C14 N2 179.7(2) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
N2 C14 C15 C16 -178.8(2) . . . . ?
C12 C11 C16 C15 0.5(4) . . . . ?
C10 C11 C16 C15 180.0(3) . . . . ?
C14 C15 C16 C11 -1.3(4) . . . . ?
C17 C18 C19 C24 1.7(4) . . . . ?
C17 C18 C19 C20 -179.2(3) . . . . ?
C24 C19 C20 C21 0.5(4) . . . . ?
C18 C19 C20 C21 -178.7(2) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C20 C21 C22 N3 -179.1(2) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
N3 C22 C23 C24 179.2(2) . . . . ?
C20 C19 C24 C23 -0.4(4) . . . . ?
C18 C19 C24 C23 178.8(3) . . . . ?
C22 C23 C24 C19 0.1(4) . . . . ?
C25 C26 C27 C32 176.5(3) . . . . ?
C25 C26 C27 C28 -3.1(4) . . . . ?
C32 C27 C28 C29 0.9(4) . . . . ?
C26 C27 C28 C29 -179.5(3) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C28 C29 C30 C31 -0.4(4) . . . . ?
C28 C29 C30 N4 179.5(2) . . . . ?
C29 C30 C31 C32 0.1(4) . . . . ?
N4 C30 C31 C32 -179.9(2) . . . . ?
C28 C27 C32 C31 -1.3(4) . . . . ?
C26 C27 C32 C31 179.1(2) . . . . ?
C30 C31 C32 C27 0.9(4) . . . . ?
O2 C33 C34 O3 -0.4(3) . . . . ?
O1 C33 C34 O3 178.7(2) . . . . ?
O2 C33 C34 C35 -120.9(3) . . . . ?
O1 C33 C34 C35 58.2(3) . . . . ?
O3 C34 C35 O4 -74.7(2) . . . . ?
C33 C34 C35 O4 45.0(3) . . . . ?
O3 C34 C35 C36 46.0(3) . . . . ?
C33 C34 C35 C36 165.7(2) . . . . ?
O4 C35 C36 O5 -2.4(3) . . . . ?
C34 C35 C36 O5 -123.5(3) . . . . ?
O4 C35 C36 O6 177.7(2) . . . . ?
C34 C35 C36 O6 56.6(3) . . . . ?
O8 C37 C38 O9 0.4(3) . . . . ?
O7 C37 C38 O9 178.8(2) . . . . ?
O8 C37 C38 C39 -119.8(3) . . . . ?
O7 C37 C38 C39 58.6(3) . . . . ?
O9 C38 C39 O10 -73.8(2) . . . . ?
C37 C38 C39 O10 46.1(3) . . . . ?
O9 C38 C39 C40 47.9(3) . . . . ?
C37 C38 C39 C40 167.9(2) . . . . ?
O10 C39 C40 O12 -6.6(3) . . . . ?
C38 C39 C40 O12 -127.9(3) . . . . ?
O10 C39 C40 O11 173.3(2) . . . . ?
C38 C39 C40 O11 52.0(3) . . . . ?
O14 C41 C42 O15 -2.3(3) . . . . ?
O13 C41 C42 O15 178.7(2) . . . . ?
O14 C41 C42 C43 -123.2(2) . . . . ?
O13 C41 C42 C43 57.8(3) . . . . ?
O15 C42 C43 O16 -67.6(3) . . . . ?
C41 C42 C43 O16 53.6(3) . . . . ?
O15 C42 C43 C44 57.5(3) . . . . ?
C41 C42 C43 C44 178.7(2) . . . . ?
O16 C43 C44 O17 -162.8(2) . . . . ?
C42 C43 C44 O17 73.3(3) . . . . ?
O16 C43 C44 O18 20.9(3) . . . . ?
C42 C43 C44 O18 -103.0(3) . . . . ?
O20 C45 C46 O21 -3.6(3) . . . . ?
O19 C45 C46 O21 178.1(2) . . . . ?
O20 C45 C46 C47 -124.2(2) . . . . ?
O19 C45 C46 C47 57.5(3) . . . . ?
O21 C46 C47 O22 -68.4(2) . . . . ?
C45 C46 C47 O22 52.9(3) . . . . ?
O21 C46 C47 C48 56.1(3) . . . . ?
C45 C46 C47 C48 177.4(2) . . . . ?
O22 C47 C48 O23 -165.0(2) . . . . ?
C46 C47 C48 O23 72.2(3) . . . . ?
O22 C47 C48 O24 18.1(3) . . . . ?
C46 C47 C48 O24 -104.7(2) . . . . ?
