#------------------------------------------------------------------------------
#$Date: 2019-09-18 17:09:23 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218453 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/03/7200390.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_7200390
loop_
_publ_author_name
'Haynes, Delia A.'
'Weng, Ze F.'
'Jones, William'
'Motherwell, W. D. Samuel'
_publ_section_title
;
 The crystal structures of three novel lutidinium pamoate salts
;
_journal_coden_ASTM              CRECF4
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              254
_journal_page_last               260
_journal_paper_doi               10.1039/b814214a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C23 H14 O6, 2(C7 H10 N)'
_chemical_formula_sum            'C37 H34 N2 O6'
_chemical_formula_weight         602.66
_chemical_name_common            '3,4 lutidine pamoate'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.32(3)
_cell_angle_beta                 103.24(3)
_cell_angle_gamma                91.58(3)
_cell_formula_units_Z            4
_cell_length_a                   11.196(2)
_cell_length_b                   12.653(3)
_cell_length_c                   22.963(5)
_cell_measurement_reflns_used    80454
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.02
_cell_volume                     3055.9(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24766
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.001
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     835
_refine_ls_number_reflns         10539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0570
_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)+(0.0656P)²+0.8072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                7878
_reflns_number_total             10539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B814214a.txt
_cod_data_source_block           3_4
_cod_depositor_comments
;
 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_cell_volume        3056.0(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200390
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
N11 N 0.65653(19) 0.05853(17) 0.51108(9) 0.0410(5) Uani 1 1 d . . .
H11 H 0.659(3) 0.005(2) 0.4704(14) 0.067(9) Uiso 1 1 d . . .
C12 C 0.7386(2) 0.0612(2) 0.56432(11) 0.0426(6) Uani 1 1 d . . .
H12 H 0.8001 0.0110 0.5640 0.051 Uiso 1 1 calc R . .
C13 C 0.7364(2) 0.1346(2) 0.61938(10) 0.0387(5) Uani 1 1 d . . .
C14 C 0.6477(2) 0.2099(2) 0.61844(10) 0.0399(6) Uani 1 1 d . . .
C15 C 0.5641(2) 0.2049(2) 0.56286(11) 0.0441(6) Uani 1 1 d . . .
H15 H 0.5028 0.2553 0.5614 0.053 Uiso 1 1 calc R . .
C16 C 0.5693(2) 0.1281(2) 0.51008(11) 0.0425(6) Uani 1 1 d . . .
H16 H 0.5103 0.1243 0.4724 0.051 Uiso 1 1 calc R . .
C17 C 0.8253(3) 0.1307(2) 0.67857(12) 0.0551(7) Uani 1 1 d . . .
H17A H 0.8625 0.2048 0.7011 0.083 Uiso 1 1 calc R . .
H17B H 0.8901 0.0837 0.6690 0.083 Uiso 1 1 calc R . .
H17C H 0.7814 0.1011 0.7042 0.083 Uiso 1 1 calc R . .
C18 C 0.6405(3) 0.2935(2) 0.67650(12) 0.0570(7) Uani 1 1 d . . .
H18A H 0.6242 0.2561 0.7069 0.086 Uiso 1 1 calc R . .
H18B H 0.5738 0.3395 0.6667 0.086 Uiso 1 1 calc R . .
H18C H 0.7188 0.3392 0.6937 0.086 Uiso 1 1 calc R . .
N21 N 0.43949(19) 0.48543(17) 0.75425(9) 0.0410(5) Uani 1 1 d . . .
H21 H 0.385(3) 0.440(2) 0.7099(14) 0.076(9) Uiso 1 1 d . . .
C22 C 0.4279(2) 0.4621(2) 0.80638(11) 0.0415(6) Uani 1 1 d . . .
H22 H 0.3728 0.4016 0.8036 0.050 Uiso 1 1 calc R . .
C23 C 0.4932(2) 0.5229(2) 0.86428(10) 0.0382(5) Uani 1 1 d . . .
C24 C 0.5706(2) 0.6131(2) 0.86724(10) 0.0395(6) Uani 1 1 d . . .
C25 C 0.5808(2) 0.6352(2) 0.81226(11) 0.0460(6) Uani 1 1 d . . .
H25 H 0.6333 0.6962 0.8133 0.055 Uiso 1 1 calc R . .
C26 C 0.5154(2) 0.5692(2) 0.75640(11) 0.0444(6) Uani 1 1 d . . .
H26 H 0.5246 0.5838 0.7190 0.053 Uiso 1 1 calc R . .
C27 C 0.4786(3) 0.4913(2) 0.92140(12) 0.0542(7) Uani 1 1 d . . .
H27A H 0.4170 0.4283 0.9095 0.081 Uiso 1 1 calc R . .
H27B H 0.4515 0.5531 0.9490 0.081 Uiso 1 1 calc R . .
H27C H 0.5577 0.4718 0.9429 0.081 Uiso 1 1 calc R . .
C28 C 0.6412(3) 0.6867(2) 0.92855(12) 0.0563(7) Uani 1 1 d . . .
H28A H 0.5839 0.7133 0.9542 0.084 Uiso 1 1 calc R . .
H28B H 0.6842 0.7490 0.9214 0.084 Uiso 1 1 calc R . .
H28C H 0.7015 0.6454 0.9498 0.084 Uiso 1 1 calc R . .
N31 N 0.05919(18) 0.12891(16) -0.00213(9) 0.0396(5) Uani 1 1 d . . .
H31 H 0.046(3) 0.180(3) 0.0409(16) 0.085(10) Uiso 1 1 d . . .
C32 C -0.0180(2) 0.1329(2) -0.05541(11) 0.0413(6) Uani 1 1 d . . .
H32 H -0.0842 0.1782 -0.0541 0.050 Uiso 1 1 calc R . .
C33 C -0.0042(2) 0.07345(19) -0.11209(10) 0.0375(5) Uani 1 1 d . . .
C34 C 0.0949(2) 0.00884(19) -0.11295(10) 0.0386(6) Uani 1 1 d . . .
C35 C 0.1724(2) 0.0061(2) -0.05699(11) 0.0437(6) Uani 1 1 d . . .
H35 H 0.2400 -0.0377 -0.0566 0.052 Uiso 1 1 calc R . .
C36 C 0.1524(2) 0.06626(19) -0.00222(10) 0.0407(6) Uani 1 1 d . . .
H36 H 0.2055 0.0631 0.0359 0.049 Uiso 1 1 calc R . .
C37 C -0.0922(2) 0.0816(2) -0.17092(11) 0.0523(7) Uani 1 1 d . . .
H37A H -0.0471 0.1121 -0.1958 0.078 Uiso 1 1 calc R . .
H37B H -0.1558 0.1295 -0.1606 0.078 Uiso 1 1 calc R . .
H37C H -0.1311 0.0086 -0.1946 0.078 Uiso 1 1 calc R . .
C38 C 0.1192(3) -0.0543(2) -0.17306(11) 0.0561(7) Uani 1 1 d . . .
H38A H 0.0487 -0.1076 -0.1961 0.084 Uiso 1 1 calc R . .
H38B H 0.1933 -0.0929 -0.1646 0.084 Uiso 1 1 calc R . .
H38C H 0.1314 -0.0037 -0.1977 0.084 Uiso 1 1 calc R . .
N41 N 0.2683(2) -0.28412(19) -0.24931(10) 0.0483(5) Uani 1 1 d . . .
H41 H 0.254(3) -0.298(3) -0.2065(16) 0.091(11) Uiso 1 1 d . . .
C42 C 0.1947(2) -0.3444(2) -0.30240(12) 0.0478(6) Uani 1 1 d . . .
H42 H 0.1288 -0.3915 -0.3007 0.057 Uiso 1 1 calc R . .
C43 C 0.2116(2) -0.3404(2) -0.35943(11) 0.0414(6) Uani 1 1 d . . .
C44 C 0.3120(2) -0.2728(2) -0.36045(11) 0.0433(6) Uani 1 1 d . . .
C45 C 0.3856(3) -0.2101(2) -0.30465(12) 0.0512(7) Uani 1 1 d . . .
H45 H 0.4530 -0.1627 -0.3046 0.061 Uiso 1 1 calc R . .
C46 C 0.3611(3) -0.2165(2) -0.24941(12) 0.0517(7) Uani 1 1 d . . .
H46 H 0.4107 -0.1724 -0.2113 0.062 Uiso 1 1 calc R . .
C47 C 0.3396(3) -0.2683(3) -0.42077(13) 0.0600(8) Uani 1 1 d . . .
H47A H 0.3523 -0.3419 -0.4435 0.090 Uiso 1 1 calc R . .
H47B H 0.4143 -0.2193 -0.4126 0.090 Uiso 1 1 calc R . .
H47C H 0.2703 -0.2407 -0.4456 0.090 Uiso 1 1 calc R . .
C48 C 0.1237(3) -0.4075(2) -0.41754(12) 0.0556(7) Uani 1 1 d . . .
H48A H 0.0770 -0.3586 -0.4395 0.083 Uiso 1 1 calc R . .
H48B H 0.0667 -0.4552 -0.4067 0.083 Uiso 1 1 calc R . .
H48C H 0.1701 -0.4523 -0.4443 0.083 Uiso 1 1 calc R . .
O111 O 0.40818(15) 0.42079(14) 0.49586(7) 0.0472(4) Uani 1 1 d . . .
H111 H 0.4363 0.4508 0.5338 0.071 Uiso 1 1 calc R . .
C111 C 0.3087(2) 0.35013(18) 0.48818(10) 0.0338(5) Uani 1 1 d . . .
C112 C 0.2697(2) 0.33629(18) 0.54066(10) 0.0332(5) Uani 1 1 d . . .
C113 C 0.1699(2) 0.26461(18) 0.53237(10) 0.0349(5) Uani 1 1 d . . .
H113 H 0.1447 0.2543 0.5675 0.042 Uiso 1 1 calc R . .
C114 C 0.1036(2) 0.20547(18) 0.47228(10) 0.0340(5) Uani 1 1 d . . .
C115 C -0.0013(2) 0.1332(2) 0.46379(11) 0.0429(6) Uani 1 1 d . . .
H115 H -0.0266 0.1231 0.4990 0.051 Uiso 1 1 calc R . .
C116 C -0.0667(2) 0.0776(2) 0.40582(12) 0.0478(6) Uani 1 1 d . . .
H116 H -0.1378 0.0302 0.4007 0.057 Uiso 1 1 calc R . .
C117 C -0.0284(2) 0.0908(2) 0.35396(11) 0.0451(6) Uani 1 1 d . . .
H117 H -0.0743 0.0522 0.3137 0.054 Uiso 1 1 calc R . .
C118 C 0.0739(2) 0.15816(19) 0.36021(10) 0.0376(5) Uani 1 1 d . . .
H118 H 0.0991 0.1640 0.3243 0.045 Uiso 1 1 calc R . .
C119 C 0.1437(2) 0.21993(17) 0.41979(10) 0.0319(5) Uani 1 1 d . . .
C120 C 0.2494(2) 0.29268(18) 0.42843(10) 0.0317(5) Uani 1 1 d . . .
C121 C 0.3036(2) 0.3053(2) 0.37509(10) 0.0362(5) Uani 1 1 d . . .
H12A H 0.3769 0.3590 0.3926 0.043 Uiso 1 1 calc R . .
H12B H 0.3329 0.2341 0.3573 0.043 Uiso 1 1 calc R . .
C122 C 0.2208(2) 0.34100(18) 0.32217(10) 0.0329(5) Uani 1 1 d . . .
O123 O 0.26513(16) 0.18341(13) 0.25367(7) 0.0458(4) Uani 1 1 d . . .
H123 H 0.2482 0.1510 0.2157 0.069 Uiso 1 1 calc R . .
C123 C 0.2051(2) 0.27530(18) 0.26239(10) 0.0346(5) Uani 1 1 d . . .
C124 C 0.1264(2) 0.30265(19) 0.21041(10) 0.0346(5) Uani 1 1 d . . .
C125 C 0.0649(2) 0.39436(19) 0.22041(10) 0.0375(5) Uani 1 1 d . . .
H125 H 0.0098 0.4108 0.1863 0.045 Uiso 1 1 calc R . .
C126 C 0.0811(2) 0.46536(19) 0.28003(10) 0.0365(5) Uani 1 1 d . . .
C127 C 0.0171(3) 0.5603(2) 0.29023(11) 0.0470(6) Uani 1 1 d . . .
H127 H -0.0388 0.5761 0.2562 0.056 Uiso 1 1 calc R . .
C128 C 0.0341(3) 0.6298(2) 0.34816(12) 0.0541(7) Uani 1 1 d . . .
H128 H -0.0110 0.6924 0.3545 0.065 Uiso 1 1 calc R . .
C129 C 0.1196(3) 0.6074(2) 0.39830(11) 0.0510(7) Uani 1 1 d . . .
H129 H 0.1341 0.6572 0.4382 0.061 Uiso 1 1 calc R . .
C130 C 0.1813(2) 0.51617(19) 0.39058(10) 0.0397(6) Uani 1 1 d . . .
H130 H 0.2382 0.5032 0.4252 0.048 Uiso 1 1 calc R . .
O131 O 0.30104(16) 0.37878(14) 0.64999(7) 0.0479(4) Uani 1 1 d . . .
C131 C 0.1624(2) 0.43943(18) 0.33148(10) 0.0339(5) Uani 1 1 d . . .
O132 O 0.42610(16) 0.46714(14) 0.61154(7) 0.0465(4) Uani 1 1 d . . .
C132 C 0.3374(2) 0.39931(19) 0.60519(10) 0.0387(6) Uani 1 1 d . . .
O133 O 0.04347(16) 0.25889(15) 0.10161(7) 0.0511(5) Uani 1 1 d . . .
C133 C 0.1138(2) 0.2312(2) 0.14596(10) 0.0386(6) Uani 1 1 d . . .
O134 O 0.17606(17) 0.14985(14) 0.13910(7) 0.0461(4) Uani 1 1 d . . .
O211 O 0.41222(15) -0.03239(14) 0.25183(7) 0.0470(4) Uani 1 1 d . . .
H211 H 0.4134 -0.0143 0.2897 0.071 Uiso 1 1 calc R . .
C211 C 0.5156(2) -0.08174(18) 0.24379(10) 0.0351(5) Uani 1 1 d . . .
C212 C 0.6042(2) -0.09675(18) 0.29625(10) 0.0345(5) Uani 1 1 d . . .
C213 C 0.7053(2) -0.15005(18) 0.28724(10) 0.0358(5) Uani 1 1 d . . .
H213 H 0.7629 -0.1621 0.3219 0.043 Uiso 1 1 calc R . .
C214 C 0.7263(2) -0.18780(18) 0.22740(10) 0.0353(5) Uani 1 1 d . . .
C215 C 0.8308(2) -0.2428(2) 0.21804(11) 0.0427(6) Uani 1 1 d . . .
H215 H 0.8881 -0.2552 0.2527 0.051 Uiso 1 1 calc R . .
C216 C 0.8517(2) -0.2787(2) 0.16044(12) 0.0492(7) Uani 1 1 d . . .
H216 H 0.9217 -0.3171 0.1549 0.059 Uiso 1 1 calc R . .
C217 C 0.7680(2) -0.2581(2) 0.10917(12) 0.0467(6) Uani 1 1 d . . .
H217 H 0.7829 -0.2818 0.0691 0.056 Uiso 1 1 calc R . .
C218 C 0.6661(2) -0.2047(2) 0.11627(10) 0.0407(6) Uani 1 1 d . . .
H218 H 0.6120 -0.1907 0.0811 0.049 Uiso 1 1 calc R . .
C219 C 0.6391(2) -0.16953(18) 0.17532(10) 0.0344(5) Uani 1 1 d . . .
C220 C 0.5312(2) -0.11792(18) 0.18428(10) 0.0348(5) Uani 1 1 d . . .
C221 C 0.4372(2) -0.09377(19) 0.13079(10) 0.0397(6) Uani 1 1 d . . .
H22A H 0.3727 -0.0546 0.1482 0.048 Uiso 1 1 calc R . .
H22B H 0.4793 -0.0422 0.1142 0.048 Uiso 1 1 calc R . .
C222 C 0.3726(2) -0.18820(19) 0.07622(10) 0.0355(5) Uani 1 1 d . . .
O223 O 0.44817(16) -0.09945(14) 0.01126(7) 0.0482(4) Uani 1 1 d . . .
H223 H 0.4429 -0.1048 -0.0265 0.072 Uiso 1 1 calc R . .
C223 C 0.3768(2) -0.1825(2) 0.01706(10) 0.0378(5) Uani 1 1 d . . .
C224 C 0.3070(2) -0.2608(2) -0.03718(10) 0.0394(6) Uani 1 1 d . . .
C225 C 0.2363(2) -0.3443(2) -0.03058(11) 0.0416(6) Uani 1 1 d . . .
H225 H 0.1883 -0.3953 -0.0666 0.050 Uiso 1 1 calc R . .
C226 C 0.2322(2) -0.3573(2) 0.02842(11) 0.0389(6) Uani 1 1 d . . .
C227 C 0.1617(2) -0.4461(2) 0.03490(12) 0.0471(6) Uani 1 1 d . . .
H227 H 0.1162 -0.4983 -0.0013 0.057 Uiso 1 1 calc R . .
C228 C 0.1571(2) -0.4592(2) 0.09153(12) 0.0510(7) Uani 1 1 d . . .
H228 H 0.1095 -0.5198 0.0949 0.061 Uiso 1 1 calc R . .
C229 C 0.2247(2) -0.3806(2) 0.14531(12) 0.0478(6) Uani 1 1 d . . .
H229 H 0.2219 -0.3887 0.1850 0.057 Uiso 1 1 calc R . .
C230 C 0.2935(2) -0.2937(2) 0.14093(11) 0.0422(6) Uani 1 1 d . . .
H230 H 0.3374 -0.2422 0.1778 0.051 Uiso 1 1 calc R . .
O231 O 0.67043(15) -0.06468(14) 0.40544(7) 0.0454(4) Uani 1 1 d . . .
C231 C 0.3016(2) -0.2778(2) 0.08250(10) 0.0368(5) Uani 1 1 d . . .
O232 O 0.49614(16) 0.00284(15) 0.36735(7) 0.0471(4) Uani 1 1 d . . .
C232 C 0.5880(2) -0.0499(2) 0.36082(10) 0.0391(6) Uani 1 1 d . . .
O233 O 0.24433(17) -0.32058(16) -0.14690(8) 0.0546(5) Uani 1 1 d . . .
C233 C 0.3118(2) -0.2507(2) -0.10075(11) 0.0441(6) Uani 1 1 d . . .
O234 O 0.38136(17) -0.17500(16) -0.10493(8) 0.0516(5) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
_geom_angle_publ_flag
C16 N11 C12 120.4(2) . . ?
C16 N11 H11 117.9(16) . . ?
C12 N11 H11 121.8(16) . . ?
N11 C12 C13 122.1(2) . . ?
N11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C14 118.0(2) . . ?
C12 C13 C17 120.4(2) . . ?
C14 C13 C17 121.6(2) . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 C18 120.3(2) . . ?
C13 C14 C18 121.1(2) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N11 C16 C15 120.5(2) . . ?
N11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
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 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 N21 C22 120.4(2) . . ?
C26 N21 H21 117.9(17) . . ?
C22 N21 H21 121.6(17) . . ?
N21 C22 C23 122.3(2) . . ?
N21 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
C22 C23 C24 117.8(2) . . ?
C22 C23 C27 120.0(2) . . ?
C24 C23 C27 122.2(2) . . ?
C25 C24 C23 118.5(2) . . ?
C25 C24 C28 120.2(2) . . ?
C23 C24 C28 121.3(2) . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
N21 C26 C25 120.6(2) . . ?
N21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C36 N31 C32 120.7(2) . . ?
C36 N31 H31 120.7(17) . . ?
C32 N31 H31 118.5(17) . . ?
N31 C32 C33 122.0(2) . . ?
N31 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C32 C33 C34 118.0(2) . . ?
C32 C33 C37 120.2(2) . . ?
C34 C33 C37 121.8(2) . . ?
C35 C34 C33 118.5(2) . . ?
C35 C34 C38 120.4(2) . . ?
C33 C34 C38 121.0(2) . . ?
C36 C35 C34 120.4(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
N31 C36 C35 120.4(2) . . ?
N31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C33 C37 H37A 109.5 . . ?
C33 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C33 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C46 N41 C42 121.0(2) . . ?
C46 N41 H41 121.5(18) . . ?
C42 N41 H41 117.3(18) . . ?
N41 C42 C43 122.1(3) . . ?
N41 C42 H42 118.9 . . ?
C43 C42 H42 118.9 . . ?
C42 C43 C44 117.7(2) . . ?
C42 C43 C48 119.7(2) . . ?
C44 C43 C48 122.6(2) . . ?
C45 C44 C43 118.9(2) . . ?
C45 C44 C47 120.5(3) . . ?
C43 C44 C47 120.6(2) . . ?
C46 C45 C44 120.1(3) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
N41 C46 C45 120.1(2) . . ?
N41 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C44 C47 H47A 109.5 . . ?
C44 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C44 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C43 C48 H48A 109.5 . . ?
C43 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C43 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C111 O111 H111 109.5 . . ?
O111 C111 C120 117.9(2) . . ?
O111 C111 C112 119.94(19) . . ?
C120 C111 C112 122.2(2) . . ?
C113 C112 C111 119.4(2) . . ?
C113 C112 C132 119.9(2) . . ?
C111 C112 C132 120.7(2) . . ?
C112 C113 C114 121.1(2) . . ?
C112 C113 H113 119.4 . . ?
C114 C113 H113 119.4 . . ?
C115 C114 C113 121.0(2) . . ?
C115 C114 C119 120.0(2) . . ?
C113 C114 C119 119.0(2) . . ?
C116 C115 C114 121.0(2) . . ?
C116 C115 H115 119.5 . . ?
C114 C115 H115 119.5 . . ?
C115 C116 C117 119.6(2) . . ?
C115 C116 H116 120.2 . . ?
C117 C116 H116 120.2 . . ?
C118 C117 C116 121.2(2) . . ?
C118 C117 H117 119.4 . . ?
C116 C117 H117 119.4 . . ?
C117 C118 C119 121.2(2) . . ?
C117 C118 H118 119.4 . . ?
C119 C118 H118 119.4 . . ?
C120 C119 C114 119.93(19) . . ?
C120 C119 C118 123.2(2) . . ?
C114 C119 C118 116.9(2) . . ?
C111 C120 C119 118.3(2) . . ?
C111 C120 C121 118.8(2) . . ?
C119 C120 C121 122.81(19) . . ?
C122 C121 C120 117.90(19) . . ?
C122 C121 H12A 107.8 . . ?
C120 C121 H12A 107.8 . . ?
C122 C121 H12B 107.8 . . ?
C120 C121 H12B 107.8 . . ?
H12A C121 H12B 107.2 . . ?
C123 C122 C131 119.1(2) . . ?
C123 C122 C121 118.2(2) . . ?
C131 C122 C121 122.69(19) . . ?
C123 O123 H123 109.5 . . ?
O123 C123 C122 118.7(2) . . ?
O123 C123 C124 120.06(19) . . ?
C122 C123 C124 121.3(2) . . ?
C125 C124 C123 119.1(2) . . ?
C125 C124 C133 121.0(2) . . ?
C123 C124 C133 120.0(2) . . ?
C124 C125 C126 121.6(2) . . ?
C124 C125 H125 119.2 . . ?
C126 C125 H125 119.2 . . ?
C125 C126 C127 121.4(2) . . ?
C125 C126 C131 119.1(2) . . ?
C127 C126 C131 119.4(2) . . ?
C128 C127 C126 121.3(2) . . ?
C128 C127 H127 119.4 . . ?
C126 C127 H127 119.4 . . ?
C127 C128 C129 119.2(2) . . ?
C127 C128 H128 120.4 . . ?
C129 C128 H128 120.4 . . ?
C130 C129 C128 121.2(2) . . ?
C130 C129 H129 119.4 . . ?
C128 C129 H129 119.4 . . ?
C129 C130 C131 121.2(2) . . ?
C129 C130 H130 119.4 . . ?
C131 C130 H130 119.4 . . ?
C122 C131 C130 122.9(2) . . ?
C122 C131 C126 119.68(19) . . ?
C130 C131 C126 117.5(2) . . ?
O132 C132 O131 124.1(2) . . ?
O132 C132 C112 118.7(2) . . ?
O131 C132 C112 117.2(2) . . ?
O134 C133 O133 124.0(2) . . ?
O134 C133 C124 118.4(2) . . ?
O133 C133 C124 117.6(2) . . ?
C211 O211 H211 109.5 . . ?
O211 C211 C220 118.5(2) . . ?
O211 C211 C212 119.8(2) . . ?
C220 C211 C212 121.7(2) . . ?
C213 C212 C211 119.2(2) . . ?
C213 C212 C232 120.6(2) . . ?
C211 C212 C232 120.1(2) . . ?
C212 C213 C214 121.4(2) . . ?
C212 C213 H213 119.3 . . ?
C214 C213 H213 119.3 . . ?
C215 C214 C213 121.5(2) . . ?
C215 C214 C219 119.5(2) . . ?
C213 C214 C219 119.0(2) . . ?
C216 C215 C214 121.6(2) . . ?
C216 C215 H215 119.2 . . ?
C214 C215 H215 119.2 . . ?
C215 C216 C217 119.2(2) . . ?
C215 C216 H216 120.4 . . ?
C217 C216 H216 120.4 . . ?
C218 C217 C216 121.1(2) . . ?
C218 C217 H217 119.5 . . ?
C216 C217 H217 119.5 . . ?
C217 C218 C219 121.3(2) . . ?
C217 C218 H218 119.4 . . ?
C219 C218 H218 119.4 . . ?
C220 C219 C218 123.0(2) . . ?
C220 C219 C214 119.6(2) . . ?
C218 C219 C214 117.3(2) . . ?
C211 C220 C219 119.0(2) . . ?
C211 C220 C221 119.1(2) . . ?
C219 C220 C221 121.8(2) . . ?
C222 C221 C220 119.25(19) . . ?
C222 C221 H22A 107.5 . . ?
C220 C221 H22A 107.5 . . ?
C222 C221 H22B 107.5 . . ?
C220 C221 H22B 107.5 . . ?
H22A C221 H22B 107.0 . . ?
C223 C222 C231 118.6(2) . . ?
C223 C222 C221 118.0(2) . . ?
C231 C222 C221 123.3(2) . . ?
C223 O223 H223 109.5 . . ?
O223 C223 C222 118.5(2) . . ?
O223 C223 C224 119.7(2) . . ?
C222 C223 C224 121.8(2) . . ?
C225 C224 C223 119.1(2) . . ?
C225 C224 C233 120.6(2) . . ?
C223 C224 C233 120.3(2) . . ?
C224 C225 C226 121.9(2) . . ?
C224 C225 H225 119.1 . . ?
C226 C225 H225 119.1 . . ?
C227 C226 C225 121.6(2) . . ?
C227 C226 C231 119.8(2) . . ?
C225 C226 C231 118.6(2) . . ?
C228 C227 C226 122.0(2) . . ?
C228 C227 H227 119.0 . . ?
C226 C227 H227 119.0 . . ?
C227 C228 C229 118.6(3) . . ?
C227 C228 H228 120.7 . . ?
C229 C228 H228 120.7 . . ?
C230 C229 C228 121.1(2) . . ?
C230 C229 H229 119.5 . . ?
C228 C229 H229 119.5 . . ?
C229 C230 C231 121.9(2) . . ?
C229 C230 H230 119.1 . . ?
C231 C230 H230 119.1 . . ?
C222 C231 C230 123.4(2) . . ?
C222 C231 C226 120.0(2) . . ?
C230 C231 C226 116.6(2) . . ?
O232 C232 O231 124.1(2) . . ?
O232 C232 C212 118.7(2) . . ?
O231 C232 C212 117.1(2) . . ?
O234 C233 O233 124.1(2) . . ?
O234 C233 C224 118.7(2) . . ?
O233 C233 C224 117.1(3) . . ?
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
N11 C16 1.333(3) . ?
N11 C12 1.343(3) . ?
N11 H11 1.02(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(3) . ?
C13 C17 1.502(3) . ?
C14 C15 1.385(3) . ?
C14 C18 1.503(3) . ?
C15 C16 1.367(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N21 C26 1.324(3) . ?
N21 C22 1.334(3) . ?
N21 H21 1.07(3) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(3) . ?
C23 C27 1.504(3) . ?
C24 C25 1.387(3) . ?
C24 C28 1.508(3) . ?
C25 C26 1.373(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N31 C36 1.327(3) . ?
N31 C32 1.340(3) . ?
N31 H31 1.08(3) . ?
C32 C33 1.378(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.397(3) . ?
C33 C37 1.507(3) . ?
C34 C35 1.385(3) . ?
C34 C38 1.502(3) . ?
C35 C36 1.370(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
N41 C46 1.329(4) . ?
N41 C42 1.339(3) . ?
N41 H41 1.09(4) . ?
C42 C43 1.378(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.401(4) . ?
C43 C48 1.504(4) . ?
C44 C45 1.389(4) . ?
C44 C47 1.501(4) . ?
C45 C46 1.378(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
O111 C111 1.360(3) . ?
O111 H111 0.8400 . ?
C111 C120 1.384(3) . ?
C111 C112 1.419(3) . ?
C112 C113 1.366(3) . ?
C112 C132 1.508(3) . ?
C113 C114 1.416(3) . ?
C113 H113 0.9500 . ?
C114 C115 1.415(3) . ?
C114 C119 1.428(3) . ?
C115 C116 1.366(3) . ?
C115 H115 0.9500 . ?
C116 C117 1.399(4) . ?
C116 H116 0.9500 . ?
C117 C118 1.368(3) . ?
C117 H117 0.9500 . ?
C118 C119 1.428(3) . ?
C118 H118 0.9500 . ?
C119 C120 1.425(3) . ?
C120 C121 1.525(3) . ?
C121 C122 1.523(3) . ?
C121 H12A 0.9900 . ?
C121 H12B 0.9900 . ?
C122 C123 1.387(3) . ?
C122 C131 1.415(3) . ?
O123 C123 1.354(3) . ?
O123 H123 0.8400 . ?
C123 C124 1.435(3) . ?
C124 C125 1.363(3) . ?
C124 C133 1.505(3) . ?
C125 C126 1.408(3) . ?
C125 H125 0.9500 . ?
C126 C127 1.413(3) . ?
C126 C131 1.431(3) . ?
C127 C128 1.370(4) . ?
C127 H127 0.9500 . ?
C128 C129 1.412(4) . ?
C128 H128 0.9500 . ?
C129 C130 1.357(4) . ?
C129 H129 0.9500 . ?
C130 C131 1.426(3) . ?
C130 H130 0.9500 . ?
O131 C132 1.269(3) . ?
O132 C132 1.252(3) . ?
O133 C133 1.267(3) . ?
C133 O134 1.257(3) . ?
O211 C211 1.358(3) . ?
O211 H211 0.8400 . ?
C211 C220 1.382(3) . ?
C211 C212 1.431(3) . ?
C212 C213 1.364(3) . ?
C212 C232 1.509(3) . ?
C213 C214 1.415(3) . ?
C213 H213 0.9500 . ?
C214 C215 1.410(3) . ?
C214 C219 1.432(3) . ?
C215 C216 1.364(4) . ?
C215 H215 0.9500 . ?
C216 C217 1.412(4) . ?
C216 H216 0.9500 . ?
C217 C218 1.363(3) . ?
C217 H217 0.9500 . ?
C218 C219 1.423(3) . ?
C218 H218 0.9500 . ?
C219 C220 1.422(3) . ?
C220 C221 1.523(3) . ?
C221 C222 1.522(3) . ?
C221 H22A 0.9900 . ?
C221 H22B 0.9900 . ?
C222 C223 1.390(3) . ?
C222 C231 1.422(3) . ?
O223 C223 1.354(3) . ?
O223 H223 0.8400 . ?
C223 C224 1.430(3) . ?
C224 C225 1.362(4) . ?
C224 C233 1.509(3) . ?
C225 C226 1.415(3) . ?
C225 H225 0.9500 . ?
C226 C227 1.413(4) . ?
C226 C231 1.433(3) . ?
C227 C228 1.363(4) . ?
C227 H227 0.9500 . ?
C228 C229 1.418(4) . ?
C228 H228 0.9500 . ?
C229 C230 1.363(4) . ?
C229 H229 0.9500 . ?
C230 C231 1.427(3) . ?
C230 H230 0.9500 . ?
O231 C232 1.268(3) . ?
O232 C232 1.259(3) . ?
O233 C233 1.268(3) . ?
C233 O234 1.254(3) . ?
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 O231 1.02(3) 1.57(3) 2.580(3) 173(3) .
N21 H21 O131 1.07(3) 1.49(3) 2.558(3) 176(3) .
N31 H31 O133 1.08(3) 1.51(3) 2.585(3) 173(3) .
N41 H41 O233 1.09(4) 1.49(4) 2.576(3) 176(3) .
O111 H111 O111 0.84 2.66 2.773(3) 88.9 2_666
