#------------------------------------------------------------------------------
#$Date: 2023-12-07 13:48:14 +0200 (Thu, 07 Dec 2023) $
#$Revision: 288129 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/29/2022923.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_2022923
loop_
_publ_author_name
'Stapf, Manuel'
'Schmidt, Ute'
'Seichter, Wilhelm'
'Mazik, Monika'
_publ_section_title
;
 Synthesis and crystal structures of two solvates of
 1-{[2,6-bis-(hy-droxy-meth-yl)-4-methyl-phen-oxy]meth-yl}-3,5-bis-{[(4,6-di-methyl-pyridin-2-yl)amino]meth-yl}-2,4,6-tri-ethyl-benzene.
;
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1067
_journal_page_last               1071
_journal_paper_doi               10.1107/S2056989023009155
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C38 H50 N4 O3, 0.777C3 H8 O, 0.223H2 O1'
_chemical_formula_moiety         'C38 H50 N4 O3, 0.777(C3 H8 O), 0.223 O'
_chemical_formula_sum            'C40.33 H56.22 N4 O4'
_chemical_formula_weight         661.08
_chemical_name_systematic
'1-{[2,6-Bis(hydroxymethyl)-4-methylphenoxy]methyl}-3,5-bis{[(4,6-dimethylpyridin-2-yl)amino]methyl}-2,4,6-triethylbenzene--n-propanol--water (1/0.777/0.223)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                102.2675(12)
_cell_angle_beta                 98.8911(10)
_cell_angle_gamma                92.9034(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6241(2)
_cell_length_b                   11.1755(2)
_cell_length_c                   20.1270(4)
_cell_measurement_reflns_used    9616
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.34
_cell_volume                     1865.73(7)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32606
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.400
_diffrn_reflns_theta_min         2.483
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       rod
_exptl_crystal_F_000             716.4
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         8447
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0511P)²+0.8172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                6498
_reflns_number_total             8447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ex2075sup1.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 2022922--2022923.cif.'
_cod_database_code               2022923
_cod_database_fobs_code          2022923
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.09845(11) 0.21196(9) 0.25578(5) 0.0186(2) Uani d 1 A 4
O O2 0.73337(11) 0.35817(9) 0.35632(5) 0.0202(2) Uani d 1 A 4
H H2 0.698(2) 0.4167(15) 0.3391(10) 0.051(6) Uiso d 1 B 4
O O3 1.53531(11) 0.16740(10) 0.37193(6) 0.0228(2) Uani d 1 A 4
H H3 1.595(2) 0.2298(14) 0.3714(11) 0.055(7) Uiso d 1 C 4
N N1 0.56482(15) -0.11050(12) 0.33365(7) 0.0224(3) Uani d 1 A 4
H H1B 0.574(2) -0.0295(9) 0.3422(9) 0.029(5) Uiso d 1 D 4
N N2 0.45201(13) -0.28824(11) 0.35529(6) 0.0169(2) Uani d 1 A 4
C C1 0.89520(15) 0.03615(13) 0.20963(7) 0.0172(3) Uani d 1 A 4
C C2 0.84608(15) -0.04442(13) 0.24865(7) 0.0168(3) Uani d 1 A 4
C C3 0.68766(16) -0.09218(13) 0.23522(7) 0.0177(3) Uani d 1 A 4
C C4 0.57876(16) -0.05761(14) 0.18474(7) 0.0194(3) Uani d 1 A 4
C C5 0.62879(16) 0.02517(14) 0.14751(7) 0.0194(3) Uani d 1 A 4
C C6 0.78643(16) 0.07368(13) 0.16017(7) 0.0181(3) Uani d 1 A 4
C C7 1.06643(15) 0.08464(13) 0.21945(7) 0.0188(3) Uani d 1 A 4
H H7A 1.1318 0.0338 0.2453 0.023 Uiso calc 1 A 4
H H7B 1.0984 0.0754 0.1736 0.023 Uiso calc 1 A 4
C C8 1.11557(15) 0.23328(12) 0.32727(7) 0.0150(3) Uani d 1 A 4
C C9 0.99458(15) 0.28480(13) 0.35935(7) 0.0170(3) Uani d 1 A 4
C C10 1.01731(15) 0.31362(13) 0.43082(7) 0.0181(3) Uani d 1 A 4
H H10 0.9363 0.3494 0.4534 0.022 Uiso calc 1 A 4
C C11 1.15576(16) 0.29156(13) 0.47053(7) 0.0189(3) Uani d 1 A 4
C C12 1.27600(15) 0.24325(13) 0.43672(7) 0.0183(3) Uani d 1 A 4
H H12 1.3717 0.2293 0.4632 0.022 Uiso calc 1 A 4
C C13 1.25877(15) 0.21523(12) 0.36541(7) 0.0164(3) Uani d 1 A 4
C C14 0.84727(17) 0.31143(16) 0.31560(8) 0.0272(3) Uani d 1 A 4
H H14A 0.8754 0.3721 0.2891 0.033 Uiso calc 1 A 4
H H14B 0.8009 0.2350 0.2822 0.033 Uiso calc 1 A 4
C C15 1.17600(18) 0.32174(16) 0.54809(8) 0.0273(3) Uani d 1 A 4
H H15A 1.1270 0.2537 0.5635 0.041 Uiso calc 1 A 4
H H15B 1.1256 0.3969 0.5637 0.041 Uiso calc 1 A 4
H H15C 1.2885 0.3342 0.5676 0.041 Uiso calc 1 A 4
C C16 1.39215(16) 0.17201(15) 0.32754(8) 0.0246(3) Uani d 1 A 4
H H16A 1.3594 0.0891 0.2980 0.029 Uiso calc 1 A 4
H H16B 1.4108 0.2280 0.2970 0.029 Uiso calc 1 A 4
C C17 0.96211(16) -0.08286(14) 0.30354(7) 0.0206(3) Uani d 1 A 4
H H17A 0.9064 -0.0985 0.3407 0.025 Uiso calc 1 A 4
H H17B 1.0451 -0.0149 0.3240 0.025 Uiso calc 1 A 4
C C18 1.03917(17) -0.19885(14) 0.27405(8) 0.0259(3) Uani d 1 A 4
H H18A 0.9576 -0.2670 0.2548 0.039 Uiso calc 1 A 4
H H18B 1.1133 -0.2203 0.3109 0.039 Uiso calc 1 A 4
H H18C 1.0958 -0.1834 0.2377 0.039 Uiso calc 1 A 4
C C19 0.63062(16) -0.17910(13) 0.27645(7) 0.0190(3) Uani d 1 A 4
H H19A 0.5494 -0.2412 0.2464 0.023 Uiso calc 1 A 4
H H19B 0.7196 -0.2226 0.2942 0.023 Uiso calc 1 A 4
C C20 0.46973(15) -0.16490(13) 0.36898(7) 0.0164(3) Uani d 1 A 4
C C21 0.35623(16) -0.34081(13) 0.39077(8) 0.0201(3) Uani d 1 A 4
C C22 0.27879(16) -0.27285(14) 0.43864(8) 0.0213(3) Uani d 1 A 4
H H22 0.2130 -0.3132 0.4623 0.026 Uiso calc 1 A 4
C C23 0.29668(15) -0.14425(13) 0.45257(7) 0.0182(3) Uani d 1 A 4
C C24 0.39397(16) -0.09037(13) 0.41748(7) 0.0179(3) Uani d 1 A 4
H H24 0.4101 -0.0034 0.4258 0.021 Uiso calc 1 A 4
C C25 0.3398(2) -0.47858(15) 0.37504(10) 0.0357(4) Uani d 1 A 4
H H25A 0.3121 -0.5103 0.3250 0.054 Uiso calc 1 A 4
H H25B 0.2569 -0.5070 0.3977 0.054 Uiso calc 1 A 4
H H25C 0.4398 -0.5086 0.3921 0.054 Uiso calc 1 A 4
C C26 0.20822(17) -0.06871(15) 0.50283(8) 0.0251(3) Uani d 1 A 4
H H26A 0.2463 0.0182 0.5111 0.038 Uiso calc 1 A 4
H H26B 0.2252 -0.0958 0.5464 0.038 Uiso calc 1 A 4
H H26C 0.0955 -0.0793 0.4837 0.038 Uiso calc 1 A 4
C C27 0.40803(16) -0.11206(16) 0.16904(8) 0.0275(3) Uani d 1 A 4
H H27A 0.3392 -0.0505 0.1548 0.033 Uiso calc 1 A 4
H H27B 0.3779 -0.1305 0.2115 0.033 Uiso calc 1 A 4
C C28 0.3810(2) -0.22925(19) 0.11221(10) 0.0407(4) Uani d 1 A 4
H H28A 0.4138 -0.2121 0.0704 0.061 Uiso calc 1 A 4
H H28B 0.2689 -0.2583 0.1023 0.061 Uiso calc 1 A 4
H H28C 0.4430 -0.2926 0.1274 0.061 Uiso calc 1 A 4
C C29 0.50860(18) 0.06695(16) 0.09561(8) 0.0248(3) Uani d 0.7770(18) A 1
H H29A 0.557(3) 0.092(2) 0.0586(10) 0.012(6) Uiso d 0.7770(18) A 1
H H29B 0.435(6) -0.003(4) 0.067(3) 0.07(2) Uiso d 0.7770(18) A 1
N N3 0.4192(2) 0.15643(19) 0.13029(10) 0.0251(4) Uani d 0.7770(18) A 1
H H3A 0.436(2) 0.1759(19) 0.1758(5) 0.020(5) Uiso d 0.7770(18) A 1
N N4 0.2978(4) 0.2039(3) 0.02829(14) 0.0257(6) Uani d 0.7770(18) A 1
C C30 0.3194(2) 0.2263(2) 0.09810(11) 0.0180(4) Uani d 0.7770(18) A 1
C C31 0.2037(3) 0.2785(3) -0.00194(12) 0.0248(5) Uani d 0.7770(18) A 1
C C32 0.1361(3) 0.3734(3) 0.03600(12) 0.0298(6) Uani d 0.7770(18) A 1
H H32 0.0745 0.4257 0.0133 0.036 Uiso calc 0.7770(18) A 1
C C33 0.1582(2) 0.3925(2) 0.10761(13) 0.0252(5) Uani d 0.7770(18) A 1
C C34 0.2507(2) 0.31710(17) 0.13893(10) 0.0189(4) Uani d 0.7770(18) A 1
H H34 0.2672 0.3270 0.1876 0.023 Uiso calc 0.7770(18) A 1
C C35 0.1725(4) 0.2488(3) -0.07895(13) 0.0414(6) Uani d 0.7770(18) A 1
H H35A 0.2727 0.2440 -0.0962 0.062 Uiso calc 0.7770(18) A 1
H H35B 0.1148 0.3132 -0.0953 0.062 Uiso calc 0.7770(18) A 1
H H35C 0.1094 0.1696 -0.0959 0.062 Uiso calc 0.7770(18) A 1
C C36 0.0891(3) 0.4958(2) 0.15129(15) 0.0446(6) Uani d 0.7770(18) A 1
H H36A 0.0779 0.4752 0.1954 0.067 Uiso calc 0.7770(18) A 1
H H36B -0.0146 0.5081 0.1272 0.067 Uiso calc 0.7770(18) A 1
H H36C 0.1588 0.5714 0.1598 0.067 Uiso calc 0.7770(18) A 1
C C29B 0.50860(18) 0.06695(16) 0.09561(8) 0.0248(3) Uani d 0.2230(18) A 2
H H29C 0.579(9) 0.122(7) 0.079(5) 0.02(3) Uiso d 0.2230(18) A 2
H H29D 0.430(10) -0.003(7) 0.072(6) 0.00(3) Uiso d 0.2230(18) A 2
N N3B 0.4781(9) 0.2014(7) 0.1409(4) 0.0251(4) Uani d 0.2230(18) A 2
H H3B 0.5311 0.2308 0.1828 0.030 Uiso calc 0.2230(18) A 2
C C30B 0.3666(9) 0.2663(7) 0.1110(4) 0.0180(4) Uani d 0.2230(18) A 2
N N4B 0.3042(18) 0.2338(12) 0.0422(5) 0.0257(6) Uani d 0.2230(18) A 2
C C31B 0.1883(14) 0.3023(12) 0.0176(4) 0.0248(5) Uani d 0.2230(18) A 2
C C32B 0.1411(13) 0.3978(10) 0.0642(5) 0.0298(6) Uani d 0.2230(18) A 2
H H32B 0.0576 0.4426 0.0484 0.036 Uiso calc 0.2230(18) A 2
C C33B 0.2104(9) 0.4298(7) 0.1321(4) 0.0252(5) Uani d 0.2230(18) A 2
C C34B 0.3272(8) 0.3642(6) 0.1572(3) 0.0189(4) Uani d 0.2230(18) A 2
H H34B 0.3780 0.3855 0.2040 0.023 Uiso calc 0.2230(18) A 2
C C35B 0.1166(13) 0.2733(10) -0.0584(4) 0.0414(6) Uani d 0.2230(18) A 2
H H35D 0.1545 0.3374 -0.0800 0.062 Uiso calc 0.2230(18) A 2
H H35E 0.0016 0.2701 -0.0633 0.062 Uiso calc 0.2230(18) A 2
H H35F 0.1476 0.1936 -0.0810 0.062 Uiso calc 0.2230(18) A 2
C C36B 0.1663(12) 0.5312(9) 0.1880(5) 0.0446(6) Uani d 0.2230(18) A 2
H H36D 0.0909 0.5805 0.1668 0.067 Uiso calc 0.2230(18) A 2
H H36E 0.2612 0.5839 0.2123 0.067 Uiso calc 0.2230(18) A 2
H H36F 0.1185 0.4942 0.2209 0.067 Uiso calc 0.2230(18) A 2
C C37 0.83976(17) 0.16528(14) 0.12075(7) 0.0229(3) Uani d 1 . .
H H37A 0.9310 0.2190 0.1496 0.028 Uiso calc 1 A 4
H H37B 0.7535 0.2178 0.1116 0.028 Uiso calc 1 A 4
C C38 0.88619(19) 0.10262(17) 0.05233(8) 0.0303(4) Uani d 1 . .
H H38A 0.9800 0.0588 0.0614 0.045 Uiso calc 1 . .
H H38B 0.9091 0.1648 0.0266 0.045 Uiso calc 1 . .
H H38C 0.7992 0.0442 0.0251 0.045 Uiso calc 1 . .
O O1A 0.64599(19) 0.54143(15) 0.29387(8) 0.0208(3) Uani d 0.7770(18) A 1
H H1A 0.585(3) 0.5911(19) 0.3115(12) 0.040(7) Uiso d 0.7770(18) A 1
C C1A 0.5739(2) 0.49317(18) 0.22359(11) 0.0214(4) Uani d 0.7770(18) A 1
H H1A1 0.4747 0.5319 0.2138 0.026 Uiso calc 0.7770(18) A 1
H H1A2 0.5475 0.4036 0.2163 0.026 Uiso calc 0.7770(18) A 1
C C2A 0.6820(2) 0.5168(2) 0.17434(10) 0.0276(5) Uani d 0.7770(18) A 1
H H2A1 0.7823 0.4801 0.1853 0.033 Uiso calc 0.7770(18) A 1
H H2A2 0.7063 0.6065 0.1812 0.033 Uiso calc 0.7770(18) A 1
C C3A 0.6105(3) 0.4638(2) 0.09917(10) 0.0294(5) Uani d 0.7770(18) A 1
H H3A1 0.5876 0.3748 0.0919 0.044 Uiso calc 0.7770(18) A 1
H H3A2 0.6852 0.4810 0.0696 0.044 Uiso calc 0.7770(18) A 1
H H3A3 0.5128 0.5016 0.0876 0.044 Uiso calc 0.7770(18) A 1
O O1W 0.5762(7) 0.4957(6) 0.2720(3) 0.0296(13) Uani d 0.2230(18) A 2
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
C8 O1 C7 . . 115.57(10) ?
C14 O2 H2 . . 104.6(15) ?
C16 O3 H3 . . 106.9(15) ?
C20 N1 C19 . . 122.83(12) ?
C20 N1 H1B . . 117.4(12) ?
C19 N1 H1B . . 119.1(12) ?
C20 N2 C21 . . 117.16(12) ?
C2 C1 C6 . . 120.70(12) ?
C2 C1 C7 . . 121.07(12) ?
C6 C1 C7 . . 118.23(12) ?
C1 C2 C3 . . 119.07(12) ?
C1 C2 C17 . . 121.05(12) ?
C3 C2 C17 . . 119.86(12) ?
C4 C3 C2 . . 120.64(12) ?
C4 C3 C19 . . 118.89(12) ?
C2 C3 C19 . . 120.45(12) ?
C5 C4 C3 . . 119.56(13) ?
C5 C4 C27 . . 119.92(12) ?
C3 C4 C27 . . 120.50(13) ?
C4 C5 C6 . . 120.59(12) ?
C5 C6 C1 . . 119.36(13) ?
C5 C6 C37 . . 120.51(12) ?
C1 C6 C37 . . 120.13(12) ?
O1 C7 C1 . . 113.97(11) ?
O1 C7 H7A . . 108.8 ?
C1 C7 H7A . . 108.8 ?
O1 C7 H7B . . 108.8 ?
C1 C7 H7B . . 108.8 ?
H7A C7 H7B . . 107.7 ?
O1 C8 C9 . . 118.59(11) ?
O1 C8 C13 . . 119.47(11) ?
C9 C8 C13 . . 121.57(12) ?
C10 C9 C8 . . 118.17(12) ?
C10 C9 C14 . . 122.45(12) ?
C8 C9 C14 . . 119.34(12) ?
C9 C10 C11 . . 121.80(13) ?
C9 C10 H10 . . 119.1 ?
C11 C10 H10 . . 119.1 ?
C10 C11 C12 . . 118.43(13) ?
C10 C11 C15 . . 120.63(13) ?
C12 C11 C15 . . 120.93(12) ?
C13 C12 C11 . . 121.44(12) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C12 C13 C8 . . 118.48(12) ?
C12 C13 C16 . . 122.44(12) ?
C8 C13 C16 . . 119.01(12) ?
O2 C14 C9 . . 111.93(12) ?
O2 C14 H14A . . 109.2 ?
C9 C14 H14A . . 109.2 ?
O2 C14 H14B . . 109.2 ?
C9 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O3 C16 C13 . . 113.73(12) ?
O3 C16 H16A . . 108.8 ?
C13 C16 H16A . . 108.8 ?
O3 C16 H16B . . 108.8 ?
C13 C16 H16B . . 108.8 ?
H16A C16 H16B . . 107.7 ?
C2 C17 C18 . . 112.02(12) ?
C2 C17 H17A . . 109.2 ?
C18 C17 H17A . . 109.2 ?
C2 C17 H17B . . 109.2 ?
C18 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N1 C19 C3 . . 109.77(12) ?
N1 C19 H19A . . 109.7 ?
C3 C19 H19A . . 109.7 ?
N1 C19 H19B . . 109.7 ?
C3 C19 H19B . . 109.7 ?
H19A C19 H19B . . 108.2 ?
N2 C20 N1 . . 117.99(12) ?
N2 C20 C24 . . 122.90(12) ?
N1 C20 C24 . . 119.11(13) ?
N2 C21 C22 . . 122.59(13) ?
N2 C21 C25 . . 116.06(13) ?
C22 C21 C25 . . 121.34(13) ?
C21 C22 C23 . . 120.18(13) ?
C21 C22 H22 . . 119.9 ?
C23 C22 H22 . . 119.9 ?
C24 C23 C22 . . 117.67(13) ?
C24 C23 C26 . . 121.49(13) ?
C22 C23 C26 . . 120.81(13) ?
C23 C24 C20 . . 119.50(13) ?
C23 C24 H24 . . 120.3 ?
C20 C24 H24 . . 120.3 ?
C21 C25 H25A . . 109.5 ?
C21 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C21 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C23 C26 H26A . . 109.5 ?
C23 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C23 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C4 C27 C28 . . 112.48(13) ?
C4 C27 H27A . . 109.1 ?
C28 C27 H27A . . 109.1 ?
C4 C27 H27B . . 109.1 ?
C28 C27 H27B . . 109.1 ?
H27A C27 H27B . . 107.8 ?
C27 C28 H28A . . 109.5 ?
C27 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C27 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
N3 C29 H29A . . 114.9(14) ?
N3 C29 H29B . . 109(4) ?
H29A C29 H29B . . 99(4) ?
C30 N3 C29 . . 124.39(17) ?
C30 N3 H3A . . 116.1(14) ?
C29 N3 H3A . . 119.1(14) ?
C30 N4 C31 . . 116.3(2) ?
N4 C30 N3 . . 117.7(2) ?
N4 C30 C34 . . 124.2(2) ?
N3 C30 C34 . . 118.01(18) ?
N4 C31 C32 . . 122.3(2) ?
N4 C31 C35 . . 116.1(2) ?
C32 C31 C35 . . 121.5(2) ?
C31 C32 C33 . . 119.9(2) ?
C31 C32 H32 . . 120.0 ?
C33 C32 H32 . . 120.0 ?
C34 C33 C32 . . 118.57(19) ?
C34 C33 C36 . . 119.4(2) ?
C32 C33 C36 . . 122.0(2) ?
C33 C34 C30 . . 118.60(18) ?
C33 C34 H34 . . 120.7 ?
C30 C34 H34 . . 120.7 ?
C31 C35 H35A . . 109.5 ?
C31 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C31 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C33 C36 H36A . . 109.5 ?
C33 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C33 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
N3B C29B H29C . . 79(6) ?
N3B C29B H29D . . 128(7) ?
H29C C29B H29D . . 133(9) ?
C30B N3B C29B . . 117.4(6) ?
C30B N3B H3B . . 121.3 ?
C29B N3B H3B . . 121.3 ?
N4B C30B C34B . . 125.1(8) ?
N4B C30B N3B . . 122.1(8) ?
C34B C30B N3B . . 112.8(6) ?
C30B N4B C31B . . 117.6(9) ?
N4B C31B C32B . . 118.1(9) ?
N4B C31B C35B . . 120.5(8) ?
C32B C31B C35B . . 121.4(9) ?
C33B C32B C31B . . 122.3(9) ?
C33B C32B H32B . . 118.9 ?
C31B C32B H32B . . 118.9 ?
C32B C33B C34B . . 120.4(7) ?
C32B C33B C36B . . 126.8(8) ?
C34B C33B C36B . . 112.7(7) ?
C30B C34B C33B . . 116.4(6) ?
C30B C34B H34B . . 121.8 ?
C33B C34B H34B . . 121.8 ?
C31B C35B H35D . . 109.5 ?
C31B C35B H35E . . 109.5 ?
H35D C35B H35E . . 109.5 ?
C31B C35B H35F . . 109.5 ?
H35D C35B H35F . . 109.5 ?
H35E C35B H35F . . 109.5 ?
C33B C36B H36D . . 109.5 ?
C33B C36B H36E . . 109.5 ?
H36D C36B H36E . . 109.5 ?
C33B C36B H36F . . 109.5 ?
H36D C36B H36F . . 109.5 ?
H36E C36B H36F . . 109.5 ?
C6 C37 C38 . . 112.42(13) ?
C6 C37 H37A . . 109.1 ?
C38 C37 H37A . . 109.1 ?
C6 C37 H37B . . 109.1 ?
C38 C37 H37B . . 109.1 ?
H37A C37 H37B . . 107.9 ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C1A O1A H1A . . 106.5(18) ?
O1A C1A C2A . . 111.33(15) ?
O1A C1A H1A1 . . 109.4 ?
C2A C1A H1A1 . . 109.4 ?
O1A C1A H1A2 . . 109.4 ?
C2A C1A H1A2 . . 109.4 ?
H1A1 C1A H1A2 . . 108.0 ?
C1A C2A C3A . . 112.71(17) ?
C1A C2A H2A1 . . 109.0 ?
C3A C2A H2A1 . . 109.0 ?
C1A C2A H2A2 . . 109.0 ?
C3A C2A H2A2 . . 109.0 ?
H2A1 C2A H2A2 . . 107.8 ?
C2A C3A H3A1 . . 109.5 ?
C2A C3A H3A2 . . 109.5 ?
H3A1 C3A H3A2 . . 109.5 ?
C2A C3A H3A3 . . 109.5 ?
H3A1 C3A H3A3 . . 109.5 ?
H3A2 C3A H3A3 . . 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
O1 C8 . 1.3907(16) ?
O1 C7 . 1.4460(17) ?
O2 C14 . 1.4241(17) ?
O2 H2 . 0.850(9) ?
O3 C16 . 1.4179(17) ?
O3 H3 . 0.850(10) ?
N1 C20 . 1.3642(18) ?
N1 C19 . 1.4513(18) ?
N1 H1B . 0.881(9) ?
N2 C20 . 1.3429(18) ?
N2 C21 . 1.3599(18) ?
C1 C2 . 1.404(2) ?
C1 C6 . 1.4055(19) ?
C1 C7 . 1.5154(18) ?
C2 C3 . 1.4054(19) ?
C2 C17 . 1.5198(18) ?
C3 C4 . 1.4043(19) ?
C3 C19 . 1.5147(19) ?
C4 C5 . 1.399(2) ?
C4 C27 . 1.5237(19) ?
C5 C6 . 1.4024(19) ?
C5 C29B . 1.5184(19) ?
C5 C29 . 1.5184(19) ?
C6 C37 . 1.516(2) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.3958(18) ?
C8 C13 . 1.3975(18) ?
C9 C10 . 1.3860(19) ?
C9 C14 . 1.5105(19) ?
C10 C11 . 1.3942(19) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3959(19) ?
C11 C15 . 1.506(2) ?
C12 C13 . 1.385(2) ?
C12 H12 . 0.9500 ?
C13 C16 . 1.5194(19) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.535(2) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C24 . 1.4073(19) ?
C21 C22 . 1.375(2) ?
C21 C25 . 1.499(2) ?
C22 C23 . 1.400(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.370(2) ?
C23 C26 . 1.5030(19) ?
C24 H24 . 0.9500 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
C27 C28 . 1.526(3) ?
C27 H27A . 0.9900 ?
C27 H27B . 0.9900 ?
C28 H28A . 0.9800 ?
C28 H28B . 0.9800 ?
C28 H28C . 0.9800 ?
C29 N3 . 1.425(2) ?
C29 H29A . 0.988(9) ?
C29 H29B . 0.996(10) ?
N3 C30 . 1.372(3) ?
N3 H3A . 0.883(9) ?
N4 C30 . 1.355(3) ?
N4 C31 . 1.362(3) ?
C30 C34 . 1.383(3) ?
C31 C32 . 1.381(3) ?
C31 C35 . 1.493(3) ?
C32 C33 . 1.393(3) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.372(3) ?
C33 C36 . 1.504(3) ?
C34 H34 . 0.9500 ?
C35 H35A . 0.9800 ?
C35 H35B . 0.9800 ?
C35 H35C . 0.9800 ?
C36 H36A . 0.9800 ?
C36 H36B . 0.9800 ?
C36 H36C . 0.9800 ?
C29B N3B . 1.640(8) ?
C29B H29C . 0.991(10) ?
C29B H29D . 0.994(11) ?
N3B C30B . 1.375(11) ?
N3B H3B . 0.8800 ?
C30B N4B . 1.370(9) ?
C30B C34B . 1.371(7) ?
N4B C31B . 1.384(9) ?
C31B C32B . 1.385(8) ?
C31B C35B . 1.518(8) ?
C32B C33B . 1.368(8) ?
C32B H32B . 0.9500 ?
C33B C34B . 1.371(7) ?
C33B C36B . 1.527(8) ?
C34B H34B . 0.9500 ?
C35B H35D . 0.9800 ?
C35B H35E . 0.9800 ?
C35B H35F . 0.9800 ?
C36B H36D . 0.9800 ?
C36B H36E . 0.9800 ?
C36B H36F . 0.9800 ?
C37 C38 . 1.528(2) ?
C37 H37A . 0.9900 ?
C37 H37B . 0.9900 ?
C38 H38A . 0.9800 ?
C38 H38B . 0.9800 ?
C38 H38C . 0.9800 ?
O1A C1A . 1.431(2) ?
O1A H1A . 0.845(10) ?
C1A C2A . 1.514(3) ?
C1A H1A1 . 0.9900 ?
C1A H1A2 . 0.9900 ?
C2A C3A . 1.521(3) ?
C2A H2A1 . 0.9900 ?
C2A H2A2 . 0.9900 ?
C3A H3A1 . 0.9800 ?
C3A H3A2 . 0.9800 ?
C3A H3A3 . 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
N1 H1B O3 1_455 0.881(9) 2.211(12) 3.0704(18) 164.8(16)
O2 H2 O1A . 0.850(9) 1.857(18) 2.702(2) 171.2(18)
O2 H2 O1W . 0.850(9) 1.967(19) 2.773(6) 157.5(18)
O3 H3 O2 1_655 0.850(10) 1.923(17) 2.7646(15) 171(2)
O1A H1A N2 1_565 0.845(10) 1.97(2) 2.813(2) 177.2(19)
C10 H10 O2 . 0.95 2.44 2.7925(17) 102.0
C12 H12 O3 . 0.95 2.49 2.8362(17) 101.4
C24 H24 O3 1_455 0.95 2.65 3.4259(19) 139.3
C27 H27A N3 . 0.99 2.55 3.257(3) 128.4
C34B H34B O1W . 0.95 2.16 2.969(9) 142.5
C37 H37A O1 . 0.99 2.41 3.1687(17) 133.4
C14 H14B <i>Cg</i>1 . 0.99 2.88 3.8427(18) 165.9
C25 H25B <i>Cg</i>2 1_445 0.98 2.72 3.4520(18) 131.8
C18 H18B <i>Cg</i>3 1_655 0.98 2.69 3.6317(16) 161.2
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
C6 C1 C2 C3 . . . . 3.2(2) ?
C7 C1 C2 C3 . . . . -176.64(12) ?
C6 C1 C2 C17 . . . . -178.39(13) ?
C7 C1 C2 C17 . . . . 1.8(2) ?
C1 C2 C3 C4 . . . . -1.6(2) ?
C17 C2 C3 C4 . . . . 179.94(13) ?
C1 C2 C3 C19 . . . . -179.86(12) ?
C17 C2 C3 C19 . . . . 1.7(2) ?
C2 C3 C4 C5 . . . . 0.0(2) ?
C19 C3 C4 C5 . . . . 178.30(13) ?
C2 C3 C4 C27 . . . . 178.44(13) ?
C19 C3 C4 C27 . . . . -3.3(2) ?
C3 C4 C5 C6 . . . . 0.0(2) ?
C27 C4 C5 C6 . . . . -178.39(13) ?
C4 C5 C6 C1 . . . . 1.5(2) ?
C4 C5 C6 C37 . . . . -178.81(13) ?
C2 C1 C6 C5 . . . . -3.1(2) ?
C7 C1 C6 C5 . . . . 176.69(13) ?
C2 C1 C6 C37 . . . . 177.18(13) ?
C7 C1 C6 C37 . . . . -3.00(19) ?
C8 O1 C7 C1 . . . . 81.11(14) ?
C2 C1 C7 O1 . . . . -106.00(15) ?
C6 C1 C7 O1 . . . . 74.17(16) ?
C7 O1 C8 C9 . . . . -106.69(14) ?
C7 O1 C8 C13 . . . . 80.09(15) ?
O1 C8 C9 C10 . . . . -175.59(12) ?
C13 C8 C9 C10 . . . . -2.5(2) ?
O1 C8 C9 C14 . . . . 2.16(19) ?
C13 C8 C9 C14 . . . . 175.23(13) ?
C8 C9 C10 C11 . . . . -0.5(2) ?
C14 C9 C10 C11 . . . . -178.21(14) ?
C9 C10 C11 C12 . . . . 2.4(2) ?
C9 C10 C11 C15 . . . . -178.90(14) ?
C10 C11 C12 C13 . . . . -1.2(2) ?
C15 C11 C12 C13 . . . . -179.96(13) ?
C11 C12 C13 C8 . . . . -1.7(2) ?
C11 C12 C13 C16 . . . . 175.12(13) ?
O1 C8 C13 C12 . . . . 176.62(12) ?
C9 C8 C13 C12 . . . . 3.6(2) ?
O1 C8 C13 C16 . . . . -0.29(19) ?
C9 C8 C13 C16 . . . . -173.30(13) ?
C10 C9 C14 O2 . . . . -5.2(2) ?
C8 C9 C14 O2 . . . . 177.20(13) ?
C12 C13 C16 O3 . . . . -2.0(2) ?
C8 C13 C16 O3 . . . . 174.78(12) ?
C1 C2 C17 C18 . . . . -89.61(16) ?
C3 C2 C17 C18 . . . . 88.81(16) ?
C20 N1 C19 C3 . . . . 163.00(12) ?
C4 C3 C19 N1 . . . . -83.54(16) ?
C2 C3 C19 N1 . . . . 94.74(15) ?
C21 N2 C20 N1 . . . . -179.71(12) ?
C21 N2 C20 C24 . . . . -0.16(19) ?
C19 N1 C20 N2 . . . . 8.0(2) ?
C19 N1 C20 C24 . . . . -171.53(13) ?
C20 N2 C21 C22 . . . . 0.3(2) ?
C20 N2 C21 C25 . . . . -179.39(13) ?
N2 C21 C22 C23 . . . . 0.0(2) ?
C25 C21 C22 C23 . . . . 179.73(14) ?
C21 C22 C23 C24 . . . . -0.5(2) ?
C21 C22 C23 C26 . . . . 177.74(13) ?
C22 C23 C24 C20 . . . . 0.69(19) ?
C26 C23 C24 C20 . . . . -177.58(13) ?
N2 C20 C24 C23 . . . . -0.4(2) ?
N1 C20 C24 C23 . . . . 179.19(12) ?
C5 C4 C27 C28 . . . . 88.08(17) ?
C3 C4 C27 C28 . . . . -90.33(17) ?
C31 N4 C30 N3 . . . . -177.1(3) ?
C31 N4 C30 C34 . . . . 1.1(5) ?
C29 N3 C30 N4 . . . . 3.9(3) ?
C29 N3 C30 C34 . . . . -174.49(19) ?
C30 N4 C31 C32 . . . . 1.3(5) ?
C30 N4 C31 C35 . . . . -176.5(3) ?
N4 C31 C32 C33 . . . . -2.6(5) ?
C35 C31 C32 C33 . . . . 175.1(3) ?
C31 C32 C33 C34 . . . . 1.5(4) ?
C31 C32 C33 C36 . . . . 179.0(3) ?
C32 C33 C34 C30 . . . . 0.7(3) ?
C36 C33 C34 C30 . . . . -176.9(2) ?
N4 C30 C34 C33 . . . . -2.1(4) ?
N3 C30 C34 C33 . . . . 176.15(19) ?
C29B N3B C30B N4B . . . . -12.4(13) ?
C29B N3B C30B C34B . . . . 167.6(6) ?
C34B C30B N4B C31B . . . . -2(2) ?
N3B C30B N4B C31B . . . . 177.6(11) ?
C30B N4B C31B C32B . . . . -1(2) ?
C30B N4B C31B C35B . . . . 178.6(12) ?
N4B C31B C32B C33B . . . . 3(2) ?
C35B C31B C32B C33B . . . . -176.2(11) ?
C31B C32B C33B C34B . . . . -2.4(17) ?
C31B C32B C33B C36B . . . . -178.8(12) ?
N4B C30B C34B C33B . . . . 3.4(14) ?
N3B C30B C34B C33B . . . . -176.6(7) ?
C32B C33B C34B C30B . . . . -0.9(12) ?
C36B C33B C34B C30B . . . . 175.9(7) ?
C5 C6 C37 C38 . . . . -86.85(16) ?
C1 C6 C37 C38 . . . . 92.84(16) ?
O1A C1A C2A C3A . . . . 178.58(17) ?
