#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/97/7209721.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_7209721
loop_
_publ_author_name
'Wahl, Helene'
'Haynes, Delia A.'
'Roex, Tanya le'
_publ_section_title
;
 Hydrate formation in pyridinium pamoate salts
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              2450
_journal_paper_doi               10.1039/c3ce27027k
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety
'C6 H8 N 1+ , C23 H15 O6 1- , 1/2(H2 O), C4 H8 O'
_chemical_formula_sum            'C33 H32 N O7.5'
_chemical_formula_weight         562.60
_chemical_name_common            '3-picolinium pamoate hydrate THF solvate'
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.221(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.064(3)
_cell_length_b                   19.904(2)
_cell_length_c                   14.5130(17)
_cell_measurement_reflns_used    3061
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.42
_cell_volume                     5766.0(12)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17239
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         6302
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0551
_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)+(0.0627P)²+4.8782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1509
_reflns_number_gt                4292
_reflns_number_total             6302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce27027k.txt
_cod_data_source_block           3
_cod_original_cell_volume        5765.9(12)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C33 H32 N O7.50'
_cod_database_code               7209721
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O4 O 0.0000 0.15902(10) 0.2500 0.0244(4) Uani 1 2 d SD . .
H11 H 0.5772(13) 0.4897(12) 0.1256(19) 0.040(7) Uiso 1 1 d . . .
H224 H 0.1220(14) 0.2699(14) 0.062(2) 0.050(8) Uiso 1 1 d . . .
H234 H 0.0698(16) 0.2008(15) 0.268(2) 0.065(9) Uiso 1 1 d . . .
H211 H 0.4563(16) 0.3923(15) 0.125(2) 0.060(9) Uiso 1 1 d . . .
N11 N 0.61751(9) 0.50683(9) 0.12900(13) 0.0255(4) Uani 1 1 d . . .
C12 C 0.66858(11) 0.46543(11) 0.14425(16) 0.0299(5) Uani 1 1 d . . .
H12 H 0.6632 0.4185 0.1505 0.036 Uiso 1 1 calc R . .
C13 C 0.72975(11) 0.48991(11) 0.15122(16) 0.0297(5) Uani 1 1 d . . .
C14 C 0.73396(11) 0.55909(12) 0.14148(16) 0.0314(5) Uani 1 1 d . . .
H14 H 0.7748 0.5783 0.1471 0.038 Uiso 1 1 calc R . .
C15 C 0.67992(11) 0.60025(11) 0.12384(16) 0.0317(5) Uani 1 1 d . . .
H15 H 0.6833 0.6473 0.1158 0.038 Uiso 1 1 calc R . .
C16 C 0.62130(11) 0.57312(11) 0.11798(16) 0.0294(5) Uani 1 1 d . . .
H16 H 0.5838 0.6011 0.1062 0.035 Uiso 1 1 calc R . .
C17 C 0.78693(12) 0.44381(13) 0.1674(2) 0.0411(6) Uani 1 1 d . . .
H17A H 0.7897 0.4366 0.1025 0.062 Uiso 1 1 calc R . .
H17B H 0.7798 0.4007 0.1938 0.062 Uiso 1 1 calc R . .
H17C H 0.8288 0.4640 0.2165 0.062 Uiso 1 1 calc R . .
C20 C 0.12295(10) 0.23772(10) 0.21175(15) 0.0244(4) Uani 1 1 d . . .
C28 C 0.46503(10) 0.50527(11) 0.12099(15) 0.0255(4) Uani 1 1 d . . .
O211 O 0.41961(8) 0.36930(7) 0.11993(11) 0.0273(3) Uani 1 1 d . . .
C211 C 0.37706(10) 0.41968(10) 0.11629(14) 0.0225(4) Uani 1 1 d . . .
C212 C 0.39800(10) 0.48795(10) 0.11886(15) 0.0233(4) Uani 1 1 d . . .
C213 C 0.35505(11) 0.53866(11) 0.11542(15) 0.0260(4) Uani 1 1 d . . .
H213 H 0.3695 0.5840 0.1197 0.031 Uiso 1 1 calc R . .
C214 C 0.28996(10) 0.52508(10) 0.10571(15) 0.0257(4) Uani 1 1 d . . .
C215 C 0.24532(11) 0.57813(11) 0.09989(16) 0.0305(5) Uani 1 1 d . . .
H215 H 0.2607 0.6233 0.1077 0.037 Uiso 1 1 calc R . .
C216 C 0.18074(12) 0.56541(12) 0.08333(18) 0.0351(5) Uani 1 1 d . . .
H216 H 0.1516 0.6013 0.0803 0.042 Uiso 1 1 calc R . .
C217 C 0.15764(11) 0.49870(12) 0.07073(17) 0.0329(5) Uani 1 1 d . . .
H217 H 0.1123 0.4899 0.0570 0.040 Uiso 1 1 calc R . .
C218 C 0.19963(10) 0.44599(11) 0.07799(16) 0.0273(5) Uani 1 1 d . . .
H218 H 0.1828 0.4014 0.0697 0.033 Uiso 1 1 calc R . .
C219 C 0.26792(10) 0.45682(10) 0.09776(14) 0.0229(4) Uani 1 1 d . . .
C220 C 0.31316(10) 0.40343(10) 0.10570(14) 0.0224(4) Uani 1 1 d . . .
O221 O 0.50392(7) 0.45645(7) 0.12586(11) 0.0294(3) Uani 1 1 d . . .
O222 O 0.47978(8) 0.56549(7) 0.11559(12) 0.0317(4) Uani 1 1 d . . .
C222 C 0.29128(10) 0.33022(10) 0.09482(15) 0.0238(4) Uani 1 1 d . . .
H22A H 0.3274 0.3024 0.0914 0.029 Uiso 1 1 calc R . .
H22B H 0.2513 0.3250 0.0292 0.029 Uiso 1 1 calc R . .
C223 C 0.27466(10) 0.30263(10) 0.17958(15) 0.0227(4) Uani 1 1 d . . .
O224 O 0.16249(7) 0.28485(7) 0.05966(10) 0.0272(3) Uani 1 1 d . . .
C224 C 0.20990(10) 0.28289(10) 0.15817(15) 0.0223(4) Uani 1 1 d . . .
C225 C 0.19216(9) 0.26066(10) 0.23713(15) 0.0222(4) Uani 1 1 d . . .
C226 C 0.24022(10) 0.25749(10) 0.33541(15) 0.0229(4) Uani 1 1 d . . .
H226 H 0.2278 0.2444 0.3880 0.027 Uiso 1 1 calc R . .
C227 C 0.30748(10) 0.27325(10) 0.36024(15) 0.0228(4) Uani 1 1 d . . .
C228 C 0.35733(10) 0.26706(11) 0.46203(16) 0.0289(5) Uani 1 1 d . . .
H228 H 0.3449 0.2533 0.5143 0.035 Uiso 1 1 calc R . .
C229 C 0.42276(10) 0.28068(11) 0.48524(17) 0.0314(5) Uani 1 1 d . . .
H229 H 0.4558 0.2767 0.5534 0.038 Uiso 1 1 calc R . .
C230 C 0.44099(10) 0.30068(11) 0.40766(17) 0.0310(5) Uani 1 1 d . . .
H230 H 0.4868 0.3095 0.4241 0.037 Uiso 1 1 calc R . .
C231 C 0.39439(10) 0.30773(10) 0.30883(16) 0.0262(5) Uani 1 1 d . . .
H231 H 0.4083 0.3211 0.2580 0.031 Uiso 1 1 calc R . .
C232 C 0.32525(10) 0.29518(10) 0.28143(15) 0.0220(4) Uani 1 1 d . . .
O233 O 0.07920(7) 0.23464(8) 0.12398(11) 0.0304(4) Uani 1 1 d . . .
O234 O 0.11287(7) 0.21879(8) 0.29138(11) 0.0300(4) Uani 1 1 d . . .
O1 O 0.9191(3) 0.5944(3) 0.2578(6) 0.116(2) Uani 0.50 1 d PDU . .
C2 C 0.9104(5) 0.6430(5) 0.1873(7) 0.105(3) Uani 0.50 1 d PU . .
H2A H 0.8874 0.6821 0.2002 0.126 Uiso 0.50 1 calc PR . .
H2B H 0.8818 0.6255 0.1184 0.126 Uiso 0.50 1 calc PR . .
C4 C 0.9752(5) 0.6232(6) 0.3385(7) 0.167(5) Uani 0.50 1 d PDU . .
H4A H 1.0018 0.5866 0.3838 0.200 Uiso 0.50 1 calc PR . .
H4B H 0.9589 0.6521 0.3787 0.200 Uiso 0.50 1 calc PR . .
C3 C 1.0219(3) 0.6651(4) 0.3079(5) 0.172(3) Uani 1 1 d DU . .
C8 C 1.0131(5) 0.6134(5) 0.6271(10) 0.116(3) Uani 0.50 1 d PU . .
O2 O 1.0084(5) 0.5488(5) 0.5951(10) 0.094(4) Uani 0.25 1 d P A 1
C6 C 1.0000 0.5579(10) 0.7500 0.153(9) Uani 0.50 2 d SP . 1
C9 C 0.9559(17) 0.6217(15) 0.681(2) 0.100(8) Uani 0.25 1 d PU . 2
C5 C 1.0025(10) 0.5147(11) 0.6747(17) 0.116(7) Uani 0.25 1 d P A 1
O3 O 1.0670(7) 0.6174(8) 0.7182(12) 0.133(5) Uani 0.25 1 d PU . 2
C7 C 1.0043(10) 0.6279(11) 0.7127(13) 0.179(7) Uani 0.50 1 d P . .
C10 C 1.059(2) 0.602(3) 0.823(4) 0.146(13) Uani 0.25 1 d PU . 2
H4 H 0.0113(14) 0.1281(11) 0.3059(8) 0.065(9) Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 N11 C16 122.52(19) . .
C12 N11 H11 120.0(15) . .
C16 N11 H11 117.5(15) . .
N11 C12 C13 121.2(2) . .
N11 C12 H12 119.4 . .
C13 C12 H12 119.4 . .
C14 C13 C12 116.2(2) . .
C14 C13 C17 122.3(2) . .
C12 C13 C17 121.4(2) . .
C15 C14 C13 121.2(2) . .
C15 C14 H14 119.4 . .
C13 C14 H14 119.4 . .
C16 C15 C14 119.8(2) . .
C16 C15 H15 120.1 . .
C14 C15 H15 120.1 . .
N11 C16 C15 119.2(2) . .
N11 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C13 C17 H17A 109.5 . .
C13 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C13 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O233 C20 O234 122.80(18) . .
O233 C20 C225 122.96(18) . .
O234 C20 C225 114.21(17) . .
O222 C28 O221 122.99(19) . .
O222 C28 C212 119.78(18) . .
O221 C28 C212 117.21(18) . .
C211 O211 H211 102.1(19) . .
O211 C211 C220 118.94(18) . .
O211 C211 C212 119.32(17) . .
C220 C211 C212 121.68(18) . .
C213 C212 C211 119.20(18) . .
C213 C212 C28 119.33(18) . .
C211 C212 C28 121.43(18) . .
C212 C213 C214 121.47(19) . .
C212 C213 H213 119.3 . .
C214 C213 H213 119.3 . .
C213 C214 C215 120.97(19) . .
C213 C214 C219 119.17(18) . .
C215 C214 C219 119.82(19) . .
C216 C215 C214 121.2(2) . .
C216 C215 H215 119.4 . .
C214 C215 H215 119.4 . .
C215 C216 C217 119.5(2) . .
C215 C216 H216 120.3 . .
C217 C216 H216 120.3 . .
C218 C217 C216 121.1(2) . .
C218 C217 H217 119.5 . .
C216 C217 H217 119.5 . .
C217 C218 C219 121.4(2) . .
C217 C218 H218 119.3 . .
C219 C218 H218 119.3 . .
C218 C219 C220 123.11(18) . .
C218 C219 C214 116.98(18) . .
C220 C219 C214 119.86(18) . .
C211 C220 C219 118.48(18) . .
C211 C220 C222 119.76(17) . .
C219 C220 C222 121.59(17) . .
C220 C222 C223 115.79(16) . .
C220 C222 H22A 108.3 . .
C223 C222 H22A 108.3 . .
C220 C222 H22B 108.3 . .
C223 C222 H22B 108.3 . .
H22A C222 H22B 107.4 . .
C224 C223 C232 118.62(18) . .
C224 C223 C222 120.04(18) . .
C232 C223 C222 121.33(17) . .
C224 O224 H224 105.6(16) . .
O224 C224 C223 118.94(18) . .
O224 C224 C225 119.92(17) . .
C223 C224 C225 121.14(18) . .
C226 C225 C224 119.62(18) . .
C226 C225 C20 120.22(18) . .
C224 C225 C20 120.07(17) . .
C225 C226 C227 121.43(18) . .
C225 C226 H226 119.3 . .
C227 C226 H226 119.3 . .
C226 C227 C228 120.79(18) . .
C226 C227 C232 118.93(18) . .
C228 C227 C232 120.28(18) . .
C229 C228 C227 120.6(2) . .
C229 C228 H228 119.7 . .
C227 C228 H228 119.7 . .
C228 C229 C230 119.5(2) . .
C228 C229 H229 120.2 . .
C230 C229 H229 120.2 . .
C231 C230 C229 121.64(19) . .
C231 C230 H230 119.2 . .
C229 C230 H230 119.2 . .
C230 C231 C232 120.72(19) . .
C230 C231 H231 119.6 . .
C232 C231 H231 119.6 . .
C231 C232 C227 117.21(18) . .
C231 C232 C223 122.78(18) . .
C227 C232 C223 120.01(17) . .
C20 O234 H234 108.5(18) . .
C2 O1 C4 97.3(7) . .
O1 C2 C3 110.4(8) . 2_755
O1 C2 H2A 109.6 . .
C3 C2 H2A 109.6 2_755 .
O1 C2 H2B 109.6 . .
C3 C2 H2B 109.6 2_755 .
H2A C2 H2B 108.1 . .
O1 C4 C3 116.2(7) . .
O1 C4 H4A 108.2 . .
C3 C4 H4A 108.2 . .
O1 C4 H4B 108.2 . .
C3 C4 H4B 108.2 . .
H4A C4 H4B 107.4 . .
C4 C3 C2 126.5(9) . 2_755
C4 C3 C3 97.5(6) . 2_755
C2 C3 C3 101.2(8) 2_755 2_755
O3 C8 O2 107.3(12) . .
O3 C8 C7 60.4(12) . .
O2 C8 C7 119.4(14) . .
O3 C8 C9 93.2(14) . .
O2 C8 C9 106.1(13) . .
C7 C8 C9 33.4(10) . .
O3 C8 C10 99.0(17) . 2_756
O2 C8 C10 93.3(17) . 2_756
C7 C8 C10 42.4(15) . 2_756
C9 C8 C10 13(2) . 2_756
C8 O2 C5 101.4(15) . .
C5 C6 C5 104.8(19) . 2_756
C5 C6 C7 150.3(13) . 2_756
C5 C6 C7 104.8(10) 2_756 2_756
C5 C6 C7 104.8(10) . .
C5 C6 C7 150.3(13) 2_756 .
C7 C6 C7 45.8(14) 2_756 .
C10 C9 C7 134(10) 2_756 .
C10 C9 C7 107(10) 2_756 2_756
C7 C9 C7 55.4(19) . 2_756
C10 C9 O3 71(10) 2_756 2_756
C7 C9 O3 106(3) . 2_756
C7 C9 O3 50.2(16) 2_756 2_756
C10 C9 C8 115(10) 2_756 .
C7 C9 C8 51(3) . .
C7 C9 C8 105(2) 2_756 .
O3 C9 C8 153.3(16) 2_756 .
O2 C5 C6 113.2(14) . .
C8 O3 C7 60.4(10) . .
C8 O3 C10 120(2) . .
C7 O3 C10 64.8(15) . .
C8 O3 C9 112.0(15) . 2_756
C7 O3 C9 52.6(14) . 2_756
C10 O3 C9 17(2) . 2_756
C9 C7 C7 82(3) . 2_756
C9 C7 C10 15(4) . 2_756
C7 C7 C10 79(3) 2_756 2_756
C9 C7 O3 153(3) . .
C7 C7 O3 120(3) 2_756 .
C10 C7 O3 144(3) 2_756 .
C9 C7 C8 96(3) . .
C7 C7 C8 167.8(10) 2_756 .
C10 C7 C8 95(3) 2_756 .
O3 C7 C8 59.2(11) . .
C9 C7 C9 123.1(19) . 2_756
C7 C7 C9 43(2) 2_756 2_756
C10 C7 C9 116(3) 2_756 2_756
O3 C7 C9 77(3) . 2_756
C8 C7 C9 135(3) . 2_756
C9 C7 C6 80(2) . .
C7 C7 C6 67.1(7) 2_756 .
C10 C7 C6 65(3) 2_756 .
O3 C7 C6 93.1(15) . .
C8 C7 C6 100.7(15) . .
C9 C7 C6 68.6(15) 2_756 .
C9 C7 C10 129(4) . .
C7 C7 C10 56(2) 2_756 .
C10 C7 C10 118(4) 2_756 .
O3 C7 C10 66(2) . .
C8 C7 C10 120(2) . .
C9 C7 C10 17(3) 2_756 .
C6 C7 C10 59(2) . .
C9 C10 C7 31(7) 2_756 2_756
C9 C10 C7 56(8) 2_756 .
C7 C10 C7 45.1(17) 2_756 .
C9 C10 O3 92(10) 2_756 .
C7 C10 O3 94(3) 2_756 .
C7 C10 O3 49.4(16) . .
C9 C10 C8 52(10) 2_756 2_756
C7 C10 C8 42.5(15) 2_756 2_756
C7 C10 C8 87.1(18) . 2_756
O3 C10 C8 136(2) . 2_756
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 H4 0.963(15) .
N11 C12 1.336(3) .
N11 C16 1.336(3) .
N11 H11 0.93(3) .
C12 C13 1.398(3) .
C12 H12 0.9500 .
C13 C14 1.391(3) .
C13 C17 1.495(3) .
C14 C15 1.378(3) .
C14 H14 0.9500 .
C15 C16 1.370(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C20 O233 1.229(2) .
C20 O234 1.321(2) .
C20 C225 1.482(3) .
C28 O222 1.253(2) .
C28 O221 1.278(3) .
C28 C212 1.506(3) .
O211 C211 1.359(2) .
O211 H211 0.91(3) .
C211 C220 1.390(3) .
C211 C212 1.431(3) .
C212 C213 1.371(3) .
C213 C214 1.408(3) .
C213 H213 0.9500 .
C214 C215 1.422(3) .
C214 C219 1.431(3) .
C215 C216 1.364(3) .
C215 H215 0.9500 .
C216 C217 1.406(3) .
C216 H216 0.9500 .
C217 C218 1.374(3) .
C217 H217 0.9500 .
C218 C219 1.425(3) .
C218 H218 0.9500 .
C219 C220 1.429(3) .
C220 C222 1.522(3) .
C222 C223 1.527(3) .
C222 H22A 0.9900 .
C222 H22B 0.9900 .
C223 C224 1.384(3) .
C223 C232 1.431(3) .
O224 C224 1.366(2) .
O224 H224 0.95(3) .
C224 C225 1.430(3) .
C225 C226 1.369(3) .
C226 C227 1.405(3) .
C226 H226 0.9500 .
C227 C228 1.422(3) .
C227 C232 1.426(3) .
C228 C229 1.362(3) .
C228 H228 0.9500 .
C229 C230 1.405(3) .
C229 H229 0.9500 .
C230 C231 1.370(3) .
C230 H230 0.9500 .
C231 C232 1.425(3) .
C231 H231 0.9500 .
O234 H234 0.93(3) .
O1 C2 1.361(10) .
O1 C4 1.414(5) .
C2 C3 1.532(11) 2_755
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C4 C3 1.529(5) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C3 C2 1.532(11) 2_755
C3 C3 1.542(13) 2_755
C8 O3 1.351(17) .
C8 O2 1.357(13) .
C8 C7 1.368(16) .
C8 C9 1.76(5) .
C8 C10 2.02(5) 2_756
O2 C5 1.39(2) .
C6 C5 1.41(3) .
C6 C5 1.41(3) 2_756
C6 C7 1.51(2) 2_756
C6 C7 1.51(2) .
C9 C10 0.50(6) 2_756
C9 C7 0.97(3) .
C9 C7 1.41(3) 2_756
C9 O3 1.74(5) 2_756
O3 C7 1.37(2) .
O3 C10 1.64(5) .
O3 C9 1.74(5) 2_756
C7 C7 1.18(3) 2_756
C7 C10 1.37(4) 2_756
C7 C9 1.41(3) 2_756
C7 C10 1.63(5) .
C10 C9 0.50(6) 2_756
C10 C7 1.37(4) 2_756
C10 C8 2.02(5) 2_756
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
N11 H11 O221 0.93(3) 1.75(3) 2.682(2) 177(2) .
O224 H224 O233 0.95(3) 1.71(3) 2.590(2) 152(2) .
O234 H234 O4 0.93(3) 1.67(3) 2.5890(17) 167(3) .
O211 H211 O221 0.91(3) 1.65(3) 2.518(2) 159(3) .
O4 H4 O222 0.963(15) 1.643(17) 2.594(2) 169(2) 4_545
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_4
C16 N11 C12 C13 1.1(3) . .
N11 C12 C13 C14 0.1(3) . .
N11 C12 C13 C17 -179.5(2) . .
C12 C13 C14 C15 -1.3(3) . .
C17 C13 C14 C15 178.2(2) . .
C13 C14 C15 C16 1.5(3) . .
C12 N11 C16 C15 -0.9(3) . .
C14 C15 C16 N11 -0.4(3) . .
O211 C211 C212 C213 -179.84(18) . .
C220 C211 C212 C213 3.0(3) . .
O211 C211 C212 C28 2.7(3) . .
C220 C211 C212 C28 -174.51(18) . .
O222 C28 C212 C213 -2.8(3) . .
O221 C28 C212 C213 178.89(18) . .
O222 C28 C212 C211 174.71(19) . .
O221 C28 C212 C211 -3.6(3) . .
C211 C212 C213 C214 -2.3(3) . .
C28 C212 C213 C214 175.23(18) . .
C212 C213 C214 C215 -178.56(19) . .
C212 C213 C214 C219 -0.9(3) . .
C213 C214 C215 C216 175.3(2) . .
C219 C214 C215 C216 -2.3(3) . .
C214 C215 C216 C217 -0.7(3) . .
C215 C216 C217 C218 2.1(3) . .
C216 C217 C218 C219 -0.5(3) . .
C217 C218 C219 C220 -179.89(19) . .
C217 C218 C219 C214 -2.4(3) . .
C213 C214 C219 C218 -173.97(18) . .
C215 C214 C219 C218 3.7(3) . .
C213 C214 C219 C220 3.6(3) . .
C215 C214 C219 C220 -178.71(18) . .
O211 C211 C220 C219 -177.48(17) . .
C212 C211 C220 C219 -0.3(3) . .
O211 C211 C220 C222 -2.1(3) . .
C212 C211 C220 C222 175.11(18) . .
C218 C219 C220 C211 174.46(18) . .
C214 C219 C220 C211 -3.0(3) . .
C218 C219 C220 C222 -0.9(3) . .
C214 C219 C220 C222 -178.32(17) . .
C211 C220 C222 C223 117.3(2) . .
C219 C220 C222 C223 -67.4(2) . .
C220 C222 C223 C224 115.0(2) . .
C220 C222 C223 C232 -66.4(2) . .
C232 C223 C224 O224 -174.87(17) . .
C222 C223 C224 O224 3.8(3) . .
C232 C223 C224 C225 5.1(3) . .
C222 C223 C224 C225 -176.25(18) . .
O224 C224 C225 C226 178.65(18) . .
C223 C224 C225 C226 -1.3(3) . .
O224 C224 C225 C20 1.9(3) . .
C223 C224 C225 C20 -178.05(18) . .
O233 C20 C225 C226 -174.3(2) . .
O234 C20 C225 C226 3.6(3) . .
O233 C20 C225 C224 2.4(3) . .
O234 C20 C225 C224 -179.69(18) . .
C224 C225 C226 C227 -2.4(3) . .
C20 C225 C226 C227 174.31(18) . .
C225 C226 C227 C228 -177.38(19) . .
C225 C226 C227 C232 2.2(3) . .
C226 C227 C228 C229 178.2(2) . .
C232 C227 C228 C229 -1.3(3) . .
C227 C228 C229 C230 -0.3(3) . .
C228 C229 C230 C231 0.8(3) . .
C229 C230 C231 C232 0.3(3) . .
C230 C231 C232 C227 -1.8(3) . .
C230 C231 C232 C223 179.2(2) . .
C226 C227 C232 C231 -177.22(18) . .
C228 C227 C232 C231 2.3(3) . .
C226 C227 C232 C223 1.7(3) . .
C228 C227 C232 C223 -178.72(19) . .
C224 C223 C232 C231 173.60(19) . .
C222 C223 C232 C231 -5.0(3) . .
C224 C223 C232 C227 -5.3(3) . .
C222 C223 C232 C227 176.08(18) . .
C4 O1 C2 C3 41.8(11) . 2_755
C2 O1 C4 C3 -30.7(12) . .
O1 C4 C3 C2 -102.2(11) . 2_755
O1 C4 C3 C3 7.8(11) . 2_755
O3 C8 O2 C5 58.6(16) . .
C7 C8 O2 C5 -6.6(18) . .
C9 C8 O2 C5 -40.1(15) . .
C10 C8 O2 C5 -41.9(17) 2_756 .
O3 C8 C9 C10 -117(9) . 2_756
O2 C8 C9 C10 -8(10) . 2_756
C7 C8 C9 C10 -127(10) . 2_756
O3 C8 C9 C7 10(3) . .
O2 C8 C9 C7 119(3) . .
C10 C8 C9 C7 127(10) 2_756 .
O3 C8 C9 C7 0(2) . 2_756
O2 C8 C9 C7 109(2) . 2_756
C7 C8 C9 C7 -10.2(9) . 2_756
C10 C8 C9 C7 117(10) 2_756 2_756
O3 C8 C9 O3 -21(5) . 2_756
O2 C8 C9 O3 88(5) . 2_756
C7 C8 C9 O3 -31(3) . 2_756
C10 C8 C9 O3 96(11) 2_756 2_756
C8 O2 C5 C6 3.2(17) . .
C5 C6 C5 O2 -177(2) 2_756 .
C7 C6 C5 O2 7(3) 2_756 .
C7 C6 C5 O2 0.5(17) . .
O2 C8 O3 C7 -114.5(16) . .
C9 C8 O3 C7 -6.5(16) . .
C10 C8 O3 C7 -18(2) 2_756 .
O2 C8 O3 C10 -88(3) . .
C7 C8 O3 C10 27(3) . .
C9 C8 O3 C10 20(3) . .
C10 C8 O3 C10 8.5(15) 2_756 .
O2 C8 O3 C9 -104.1(16) . 2_756
C7 C8 O3 C9 10.4(17) . 2_756
C9 C8 O3 C9 3.9(11) . 2_756
C10 C8 O3 C9 -8(3) 2_756 2_756
C10 C9 C7 C7 -80(17) 2_756 2_756
O3 C9 C7 C7 -2.0(15) 2_756 2_756
C8 C9 C7 C7 -168.0(11) . 2_756
C7 C9 C7 C10 80(17) 2_756 2_756
O3 C9 C7 C10 78(17) 2_756 2_756
C8 C9 C7 C10 -88(17) . 2_756
C10 C9 C7 O3 65(21) 2_756 .
C7 C9 C7 O3 145(6) 2_756 .
O3 C9 C7 O3 143(6) 2_756 .
C8 C9 C7 O3 -23(6) . .
C10 C9 C7 C8 88(17) 2_756 .
C7 C9 C7 C8 168.0(11) 2_756 .
O3 C9 C7 C8 166.0(16) 2_756 .
C10 C9 C7 C9 -68(17) 2_756 2_756
C7 C9 C7 C9 12(4) 2_756 2_756
O3 C9 C7 C9 10(5) 2_756 2_756
C8 C9 C7 C9 -156(4) . 2_756
C10 C9 C7 C6 -12(16) 2_756 .
C7 C9 C7 C6 68.1(8) 2_756 .
O3 C9 C7 C6 66.1(18) 2_756 .
C8 C9 C7 C6 -99.9(16) . .
C10 C9 C7 C10 -48(19) 2_756 .
C7 C9 C7 C10 32(4) 2_756 .
O3 C9 C7 C10 30(4) 2_756 .
C8 C9 C7 C10 -136(4) . .
C8 O3 C7 C9 27(7) . .
C10 O3 C7 C9 -128(7) . .
C9 O3 C7 C9 -141(8) 2_756 .
C8 O3 C7 C7 165.9(12) . 2_756
C10 O3 C7 C7 11(2) . 2_756
C9 O3 C7 C7 -2.0(15) 2_756 2_756
C8 O3 C7 C10 50(5) . 2_756
C10 O3 C7 C10 -104(7) . 2_756
C9 O3 C7 C10 -117(5) 2_756 2_756
C10 O3 C7 C8 -155(3) . .
C9 O3 C7 C8 -167.8(19) 2_756 .
C8 O3 C7 C9 167.8(19) . 2_756
C10 O3 C7 C9 13(3) . 2_756
C8 O3 C7 C6 100.6(12) . .
C10 O3 C7 C6 -54(2) . .
C9 O3 C7 C6 -67.2(16) 2_756 .
C8 O3 C7 C10 155(3) . .
C9 O3 C7 C10 -13(3) 2_756 .
O3 C8 C7 C9 -168(3) . .
O2 C8 C7 C9 -74(3) . .
C10 C8 C7 C9 -15(4) 2_756 .
O3 C8 C7 C7 -91(14) . 2_756
O2 C8 C7 C7 3(14) . 2_756
C9 C8 C7 C7 77(13) . 2_756
C10 C8 C7 C7 62(13) 2_756 2_756
O3 C8 C7 C10 -153(3) . 2_756
O2 C8 C7 C10 -59(3) . 2_756
C9 C8 C7 C10 15(4) . 2_756
O2 C8 C7 O3 94.1(14) . .
C9 C8 C7 O3 168(3) . .
C10 C8 C7 O3 153(3) 2_756 .
O3 C8 C7 C9 -17(3) . 2_756
O2 C8 C7 C9 77(3) . 2_756
C9 C8 C7 C9 151(5) . 2_756
C10 C8 C7 C9 136(4) 2_756 2_756
O3 C8 C7 C6 -87.2(14) . .
O2 C8 C7 C6 6.9(18) . .
C9 C8 C7 C6 81(2) . .
C10 C8 C7 C6 66(3) 2_756 .
O3 C8 C7 C10 -27(3) . .
O2 C8 C7 C10 67(3) . .
C9 C8 C7 C10 141(4) . .
C10 C8 C7 C10 126(6) 2_756 .
C5 C6 C7 C9 90(3) . .
C5 C6 C7 C9 -94(4) 2_756 .
C7 C6 C7 C9 -85(3) 2_756 .
C5 C6 C7 C7 175.3(18) . 2_756
C5 C6 C7 C7 -9(4) 2_756 2_756
C5 C6 C7 C10 87(3) . 2_756
C5 C6 C7 C10 -98(3) 2_756 2_756
C7 C6 C7 C10 -89(3) 2_756 2_756
C5 C6 C7 O3 -63.2(14) . .
C5 C6 C7 O3 112(2) 2_756 .
C7 C6 C7 O3 122(2) 2_756 .
C5 C6 C7 C8 -4.0(15) . .
C5 C6 C7 C8 171.5(18) 2_756 .
C7 C6 C7 C8 -179(3) 2_756 .
C5 C6 C7 C9 -138(2) . 2_756
C5 C6 C7 C9 37(4) 2_756 2_756
C7 C6 C7 C9 47(2) 2_756 2_756
C5 C6 C7 C10 -122(2) . .
C5 C6 C7 C10 53(3) 2_756 .
C7 C6 C7 C10 62(2) 2_756 .
C9 C7 C10 C9 -77(10) . 2_756
C7 C7 C10 C9 -38(10) 2_756 2_756
C10 C7 C10 C9 -90(14) 2_756 2_756
O3 C7 C10 C9 130(12) . 2_756
C8 C7 C10 C9 155(10) . 2_756
C6 C7 C10 C9 -120(12) . 2_756
C9 C7 C10 C7 -39(5) . 2_756
C10 C7 C10 C7 -52(5) 2_756 2_756
O3 C7 C10 C7 168(3) . 2_756
C8 C7 C10 C7 -166.7(16) . 2_756
C9 C7 C10 C7 38(10) 2_756 2_756
C6 C7 C10 C7 -82(2) . 2_756
C9 C7 C10 O3 152(4) . .
C7 C7 C10 O3 -168(3) 2_756 .
C10 C7 C10 O3 140(3) 2_756 .
C8 C7 C10 O3 25(2) . .
C9 C7 C10 O3 -130(12) 2_756 .
C6 C7 C10 O3 109.8(19) . .
C9 C7 C10 C8 -32(4) . 2_756
C7 C7 C10 C8 7.4(10) 2_756 2_756
C10 C7 C10 C8 -45(5) 2_756 2_756
O3 C7 C10 C8 176(3) . 2_756
C8 C7 C10 C8 -159.3(16) . 2_756
C9 C7 C10 C8 45(10) 2_756 2_756
C6 C7 C10 C8 -74.7(19) . 2_756
C8 O3 C10 C9 -65(10) . 2_756
C7 O3 C10 C9 -39(8) . 2_756
C8 O3 C10 C7 -34(4) . 2_756
C7 O3 C10 C7 -8(2) . 2_756
C9 O3 C10 C7 31(6) 2_756 2_756
C8 O3 C10 C7 -26(3) . .
C9 O3 C10 C7 39(8) 2_756 .
C8 O3 C10 C8 -32(6) . 2_756
C7 O3 C10 C8 -7(4) . 2_756
C9 O3 C10 C8 33(5) 2_756 2_756
