#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/06/1520623.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_1520623
loop_
_publ_author_name
'Engle, Keary M.'
'Pfeifer, Lukas'
'Pidgeon, George W.'
'Giuffredi, Guy T.'
'Thompson, Amber L.'
'Paton, Robert S.'
'Brown, John M.'
'Gouverneur, Véronique'
_publ_section_title
;
 Coordination diversity in hydrogen-bonded homoleptic fluoride--alcohol
 complexes modulates reactivity
;
_journal_issue                   9
_journal_name_full               'Chem. Sci.'
_journal_page_first              5293
_journal_paper_doi               10.1039/C5SC01812A
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C12 H22 O6, 0.5(C16 H36 N), 0.5(C4 H8 O3), 0.5(F)'
_chemical_formula_sum            'C22 H44 F0.5 N0.5 O7'
_chemical_formula_weight         437.09
_chemical_melting_point          362
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2014-12-19
_audit_creation_method           CRYSTALS_ver_14.43
_audit_update_record
;
2015-05-19 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2457(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.1923(1)
_cell_length_b                   9.6565(1)
_cell_length_c                   10.6715(1)
_cell_measurement_reflns_used    43761
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     2594.06(4)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49863
_diffrn_reflns_theta_full        76.028
_diffrn_reflns_theta_max         76.028
_diffrn_reflns_theta_min         3.511
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 2510 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5353
_refine_ls_number_restraints     623
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.0003897
_refine_ls_shift/su_mean         0.0000321
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.76P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0889
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0889
_reflns_limit_h_max              31
_reflns_limit_h_min              -31
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                5330
_reflns_number_total             5371
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.21
_oxford_diffrn_Wilson_scale      0.07
_oxford_refine_ls_r_factor_ref   0.0327
_oxford_refine_ls_scale          5.14(7)
_oxford_reflns_number_all        5353
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 003lp14
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S U'S 
CONT ENANTIO 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
REM EQUIV PART(-2002,OCC) PART(-2003,OCC) 
REM WEIGHT -1 PART(-2003,OCC) 
RIDE  C(25,U'S) C(125,U'S) 
RIDE  O(26,U'S) O(126,U'S) 
RIDE O   (   1,X'S) H   (  11,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 173,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE O   (   2,X'S) H   (  21,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 273,X'S) H   ( 272,X'S) 
RIDE C   (  28,X'S) H   (  22,X'S) H   ( 282,X'S) H   ( 283,X'S) 
RIDE C   ( 127,X'S) H   (1271,X'S) H   (1273,X'S) H   (1272,X'S) 
RIDE C   ( 128,X'S) H   (1281,X'S) H   (1282,X'S) H   (1283,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 342,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 352,X'S) H   ( 353,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 372,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 393,X'S) H   ( 392,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) H   ( 432,X'S) H   ( 433,X'S) 
RIDE C   (  45,X'S) H   ( 452,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 462,X'S) H   ( 461,X'S) H   ( 463,X'S) 
REM RIDE C   (  45,X'S) H   ( 453,X'S) H   ( 452,X'S) H   ( 451,X'S) 
REM RIDE C   ( 146,X'S) H   (1461,X'S) H   (1462,X'S) H   (1463,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
REM SAME  O(44)  C(45)  C(46)  C(146)  AND 
REM CONT  O(44)  C(45)  C(146)  C(46) 
REM SIMU  0.01   O(44)  C(45)  C(46)  C(146)  AND 
REM CONT  O(44)  C(45)  C(146)  C(46) 
REM DELU  0.01   O(44)  C(45)  C(46)  C(146)  AND 
REM CONT  O(44)  C(45)  C(146)  C(46) 
DIST  0,0.01 = MEAN 
CONT  C(42) TO  C(43)  C(45) TO  C(46) 
VIBR .0, 0.00200 = O(41) TO C(42) 
VIBR .0, 0.00200 = C(42) TO O(44) 
VIBR .0, 0.00200 = C(42) TO C(43) 
VIBR .0, 0.00500 = O(44) TO O(41) 
VIBR .0, 0.00500 = C(43) TO O(41) 
VIBR .0, 0.00500 = C(43) TO O(44) 
U(IJ) .0, 0.08000 = O(41) TO C(42) 
U(IJ) .0, 0.04000 = C(42) TO O(44) 
U(IJ) .0, 0.08000 = C(42) TO C(43) 
U(IJ) .0, 0.08000 = C(46) TO C(45) 
SAME  O(24)  C(25)  O(26)  C(27)  C(28)  AND 
CONT  O(26)  C(25)  O(24)  C(28)  C(27)  AND 
CONT  O(24)  C(125)  O(126)  C(127)  C(128)  AND 
CONT  O(126)  C(125)  O(24)  C(128)  C(127) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            c5sc01812a2.cif
_cod_data_source_block           2f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '362 K' was changed to '362' - the
value should be numeric and without a unit designator.

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520618--1520631.cif.
;
_cod_original_sg_symbol_H-M      'C 2 '
_cod_original_formula_sum        'C22 H44 F0.50 N0.50 O7'
_cod_database_code               1520623
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
-x,y,-z
-x+1/2,y+1/2,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5000 0.29093(14) 0.0000 0.0461 1.0000 Uani S T . . .
O1 O 0.39970(3) 0.36457(9) -0.02106(7) 0.0289 1.0000 Uani . . . . .
C11 C 0.37073(4) 0.24111(11) -0.04825(9) 0.0238 1.0000 Uani . . . . .
C12 C 0.36889(4) 0.15315(12) 0.07075(10) 0.0265 1.0000 Uani . . . . .
C13 C 0.33440(5) 0.21737(14) 0.16840(11) 0.0338 1.0000 Uani . . . . .
O14 O 0.28256(3) 0.17026(12) 0.12972(9) 0.0407 1.0000 Uani . . . . .
C15 C 0.28884(5) 0.03256(15) 0.08343(13) 0.0395 1.0000 Uani . . . . .
O16 O 0.34320(3) 0.02270(10) 0.04716(8) 0.0329 1.0000 Uani . . . . .
C17 C 0.25181(6) 0.0139(2) -0.03001(16) 0.0547 1.0000 Uani . . . . .
C18 C 0.27987(7) -0.07335(18) 0.18547(17) 0.0561 1.0000 Uani . . . . .
O2 O 0.44479(3) 0.10867(10) -0.13326(8) 0.0318 1.0000 Uani . . . . .
C21 C 0.39232(4) 0.15886(12) -0.15711(10) 0.0248 1.0000 Uani . . . . .
C22 C 0.39079(4) 0.23933(12) -0.27945(10) 0.0271 1.0000 Uani . . . . .
C23 C 0.40659(5) 0.15158(14) -0.39095(11) 0.0341 1.0000 Uani . . . . .
O24 O 0.37229(4) 0.19721(14) -0.49126(8) 0.0528 1.0000 Uani D . . . .
C25 C 0.33256(11) 0.2785(3) -0.44719(18) 0.0307 0.4360(19) Uani D . P 1 1
O26 O 0.33829(17) 0.2781(4) -0.3145(5) 0.0400 0.4360(19) Uani D . P 1 1
C27 C 0.27893(15) 0.2152(5) -0.4848(4) 0.0846 0.4360(19) Uani D . P 1 1
C28 C 0.33989(19) 0.4187(4) -0.4930(3) 0.0696 0.4360(19) Uani D . P 1 1
C125 C 0.32378(8) 0.2419(2) -0.43703(14) 0.0307 0.5640(19) Uani D . P 1 2
O126 O 0.33653(13) 0.2787(4) -0.3103(4) 0.0400 0.5640(19) Uani D . P 1 2
C127 C 0.28570(12) 0.1246(4) -0.4376(3) 0.0712 0.5640(19) Uani D . P 1 2
C128 C 0.30319(12) 0.3697(3) -0.5081(2) 0.0625 0.5640(19) Uani D . P 1 2
N31 N 0.5000 -0.24066(14) 0.0000 0.0253 1.0000 Uani S T . . .
C32 C 0.45881(4) -0.33339(12) -0.06582(11) 0.0298 1.0000 Uani . . . . .
C33 C 0.41641(5) -0.25689(14) -0.14325(13) 0.0385 1.0000 Uani . . . . .
C34 C 0.37746(7) -0.35030(18) -0.20783(19) 0.0627 1.0000 Uani . . . . .
C35 C 0.33450(6) -0.27510(19) -0.28299(15) 0.0511 1.0000 Uani . . . . .
C36 C 0.47339(4) -0.14636(12) 0.09303(10) 0.0273 1.0000 Uani . . . . .
C37 C 0.44524(6) -0.21991(15) 0.19664(13) 0.0454 1.0000 Uani . . . . .
C38 C 0.42908(7) -0.11923(17) 0.29698(13) 0.0495 1.0000 Uani . . . . .
C39 C 0.40155(11) -0.1875(2) 0.40373(18) 0.0793 1.0000 Uani . . . . .
O41 O 0.48812(13) 0.5447(3) 0.6335(3) 0.0769 0.5000 Uani . U . 2 -1
C42 C 0.50881(14) 0.4374(4) 0.6097(3) 0.0393 0.5000 Uani D U . 2 -1
C43 C 0.5414(3) 0.3449(10) 0.6957(8) 0.0484 0.5000 Uani D U . 2 -1
O44 O 0.5000 0.37571(16) 0.5000 0.0453 1.0000 Uani S TU . 2 -1
C45 C 0.4683(2) 0.4515(5) 0.4082(4) 0.0547 0.5000 Uani D U . 2 -1
C46 C 0.4565(4) 0.3685(10) 0.2943(9) 0.0559 0.5000 Uani D U . 2 -1
H11 H 0.4299 0.3441 -0.0092 0.0439 1.0000 Uiso R . . . .
H21 H 0.4631 0.1662 -0.0954 0.0469 1.0000 Uiso R . . . .
H111 H 0.3349 0.2669 -0.0714 0.0268 1.0000 Uiso R . . . .
H121 H 0.4052 0.1366 0.1048 0.0310 1.0000 Uiso R . . . .
H132 H 0.3446 0.1849 0.2519 0.0385 1.0000 Uiso R . . . .
H131 H 0.3355 0.3200 0.1669 0.0384 1.0000 Uiso R . . . .
H171 H 0.2559 -0.0795 -0.0655 0.0820 1.0000 Uiso R . . . .
H173 H 0.2614 0.0790 -0.0950 0.0800 1.0000 Uiso R . . . .
H172 H 0.2154 0.0306 -0.0068 0.0805 1.0000 Uiso R . . . .
H181 H 0.2911 -0.1616 0.1550 0.0820 1.0000 Uiso R . . . .
H182 H 0.3002 -0.0482 0.2599 0.0834 1.0000 Uiso R . . . .
H183 H 0.2433 -0.0740 0.2037 0.0824 1.0000 Uiso R . . . .
H211 H 0.3702 0.0745 -0.1676 0.0300 1.0000 Uiso R . . . .
H231 H 0.4427 0.1702 -0.4122 0.0425 1.0000 Uiso R . . . .
H232 H 0.4004 0.0509 -0.3703 0.0416 1.0000 Uiso R . . . .
H271 H 0.2512 0.2663 -0.4467 0.1256 0.4360(19) Uiso R . P 1 1
H273 H 0.2735 0.2157 -0.5743 0.1257 0.4360(19) Uiso R . P 1 1
H272 H 0.2781 0.1217 -0.4543 0.1262 0.4360(19) Uiso R . P 1 1
H22 H 0.3137 0.4816 -0.4625 0.1059 0.4360(19) Uiso R . P 1 1
H282 H 0.3740 0.4538 -0.4643 0.1062 0.4360(19) Uiso R . P 1 1
H283 H 0.3378 0.4189 -0.5840 0.1050 0.4360(19) Uiso R . P 1 1
H1271 H 0.2536 0.1525 -0.3970 0.1039 0.5640(19) Uiso R . P 1 2
H1273 H 0.2772 0.1010 -0.5250 0.1051 0.5640(19) Uiso R . P 1 2
H1272 H 0.3024 0.0453 -0.3955 0.1039 0.5640(19) Uiso R . P 1 2
H1281 H 0.2733 0.4106 -0.4678 0.0918 0.5640(19) Uiso R . P 1 2
H1282 H 0.3338 0.4316 -0.5098 0.0939 0.5640(19) Uiso R . P 1 2
H1283 H 0.2937 0.3473 -0.5943 0.0924 0.5640(19) Uiso R . P 1 2
H221 H 0.4132 0.3226 -0.2704 0.0315 1.0000 Uiso R . . . .
H321 H 0.4783 -0.3951 -0.1167 0.0365 1.0000 Uiso R . . . .
H322 H 0.4445 -0.3873 0.0011 0.0353 1.0000 Uiso R . . . .
H332 H 0.4345 -0.2104 -0.2090 0.0517 1.0000 Uiso R . . . .
H331 H 0.3978 -0.1909 -0.0913 0.0516 1.0000 Uiso R . . . .
H342 H 0.3977 -0.4146 -0.2612 0.0798 1.0000 Uiso R . . . .
H341 H 0.3630 -0.4168 -0.1504 0.0789 1.0000 Uiso R . . . .
H352 H 0.3086 -0.3364 -0.3214 0.0776 1.0000 Uiso R . . . .
H353 H 0.3508 -0.2311 -0.3503 0.0774 1.0000 Uiso R . . . .
H351 H 0.3157 -0.2083 -0.2342 0.0796 1.0000 Uiso R . . . .
H362 H 0.5004 -0.0857 0.1267 0.0320 1.0000 Uiso R . . . .
H361 H 0.4481 -0.0915 0.0458 0.0324 1.0000 Uiso R . . . .
H372 H 0.4688 -0.2892 0.2354 0.0546 1.0000 Uiso R . . . .
H371 H 0.4136 -0.2706 0.1620 0.0583 1.0000 Uiso R . . . .
H381 H 0.4664 -0.0885 0.3497 0.0558 1.0000 Uiso R . . . .
H382 H 0.4076 -0.0418 0.2605 0.0607 1.0000 Uiso R . . . .
H391 H 0.3854 -0.1159 0.4615 0.1198 1.0000 Uiso R . . . .
H393 H 0.4272 -0.2498 0.4531 0.1194 1.0000 Uiso R . . . .
H392 H 0.3706 -0.2501 0.3669 0.1192 1.0000 Uiso R . . . .
H431 H 0.5696 0.3017 0.6544 0.0718 0.5000 Uiso R . . 2 -1
H432 H 0.5569 0.3987 0.7659 0.0713 0.5000 Uiso R . . 2 -1
H433 H 0.5188 0.2731 0.7257 0.0725 0.5000 Uiso R . . 2 -1
H452 H 0.4844 0.5394 0.3908 0.0651 0.5000 Uiso R . . 2 -1
H451 H 0.4353 0.4759 0.4478 0.0667 0.5000 Uiso R . . 2 -1
H462 H 0.4279 0.4131 0.2460 0.0822 0.5000 Uiso R . . 2 -1
H461 H 0.4878 0.3666 0.2455 0.0830 0.5000 Uiso R . . 2 -1
H463 H 0.4469 0.2754 0.3193 0.0824 0.5000 Uiso R . . 2 -1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 . O1 H11 . 107.8 no
O1 . C11 C12 . 109.16(8) yes
O1 . C11 C21 . 113.37(8) yes
C12 . C11 C21 . 111.49(8) yes
O1 . C11 H111 . 107.8 no
C12 . C11 H111 . 107.4 no
C21 . C11 H111 . 107.4 no
C11 . C12 C13 . 112.36(9) yes
C11 . C12 O16 . 111.73(8) yes
C13 . C12 O16 . 102.32(8) yes
C11 . C12 H121 . 109.8 no
C13 . C12 H121 . 111.3 no
O16 . C12 H121 . 109.2 no
C12 . C13 O14 . 102.31(9) yes
C12 . C13 H132 . 111.2 no
O14 . C13 H132 . 111.7 no
C12 . C13 H131 . 112.4 no
O14 . C13 H131 . 109.9 no
H132 . C13 H131 . 109.3 no
C13 . O14 C15 . 106.48(9) yes
O14 . C15 O16 . 105.88(9) yes
O14 . C15 C17 . 108.33(12) yes
O16 . C15 C17 . 109.92(11) yes
O14 . C15 C18 . 110.94(12) yes
O16 . C15 C18 . 108.55(12) yes
C17 . C15 C18 . 112.98(13) yes
C15 . O16 C12 . 108.78(9) yes
C15 . C17 H171 . 110.3 no
C15 . C17 H173 . 109.4 no
H171 . C17 H173 . 106.6 no
C15 . C17 H172 . 109.6 no
H171 . C17 H172 . 111.2 no
H173 . C17 H172 . 109.7 no
C15 . C18 H181 . 107.5 no
C15 . C18 H182 . 109.5 no
H181 . C18 H182 . 110.5 no
C15 . C18 H183 . 108.9 no
H181 . C18 H183 . 111.4 no
H182 . C18 H183 . 108.9 no
C21 . O2 H21 . 111.1 no
C11 . C21 O2 . 113.46(8) yes
C11 . C21 C22 . 112.99(8) yes
O2 . C21 C22 . 108.69(8) yes
C11 . C21 H211 . 107.4 no
O2 . C21 H211 . 104.8 no
C22 . C21 H211 . 109.2 no
C21 . C22 C23 . 112.80(9) yes
C21 . C22 O26 . 110.8(2) yes
C23 . C22 O26 . 102.2(2) yes
C21 . C22 H221 . 109.7 no
C23 . C22 H221 . 111.3 no
O26 . C22 H221 . 109.7 no
C21 . C22 C23 . 112.80(9) yes
C21 . C22 O126 . 108.82(16) yes
C23 . C22 O126 . 104.01(18) yes
C21 . C22 H221 . 109.7 no
C23 . C22 H221 . 111.3 no
O126 . C22 H221 . 109.9 no
C22 . C23 O24 . 104.23(9) yes
C22 . C23 H231 . 111.0 no
O24 . C23 H231 . 108.5 no
C22 . C23 H232 . 108.4 no
O24 . C23 H232 . 111.6 no
H231 . C23 H232 . 112.8 no
C23 . O24 C25 . 110.52(10) yes
C23 . O24 C125 . 106.95(9) yes
O24 . C25 O26 . 107.10(6) yes
O24 . C25 C27 . 109.40(6) yes
O26 . C25 C27 . 108.47(6) yes
O24 . C25 C28 . 108.29(6) yes
O26 . C25 C28 . 109.24(6) yes
C27 . C25 C28 . 114.12(6) yes
C25 . O26 C22 . 108.9(2) yes
C25 . C27 H271 . 109.6 no
C25 . C27 H273 . 110.5 no
H271 . C27 H273 . 110.0 no
C25 . C27 H272 . 108.6 no
H271 . C27 H272 . 108.3 no
H273 . C27 H272 . 109.7 no
C25 . C28 H22 . 112.0 no
C25 . C28 H282 . 110.2 no
H22 . C28 H282 . 106.6 no
C25 . C28 H283 . 109.6 no
H22 . C28 H283 . 109.1 no
H282 . C28 H283 . 109.3 no
O24 . C125 O126 . 107.07(6) yes
O24 . C125 C127 . 109.19(6) yes
O126 . C125 C127 . 108.46(6) yes
O24 . C125 C128 . 108.63(6) yes
O126 . C125 C128 . 109.21(6) yes
C127 . C125 C128 . 114.06(6) yes
C22 . O126 C125 . 109.09(19) yes
C125 . C127 H1271 . 109.6 no
C125 . C127 H1273 . 107.4 no
H1271 . C127 H1273 . 109.7 no
C125 . C127 H1272 . 109.3 no
H1271 . C127 H1272 . 111.5 no
H1273 . C127 H1272 . 109.3 no
C125 . C128 H1281 . 111.4 no
C125 . C128 H1282 . 104.5 no
H1281 . C128 H1282 . 112.8 no
C125 . C128 H1283 . 111.0 no
H1281 . C128 H1283 . 110.3 no
H1282 . C128 H1283 . 106.6 no
C36 3_655 N31 C32 3_655 110.09(6) yes
C36 3_655 N31 C32 . 111.15(6) yes
C32 3_655 N31 C32 . 107.89(11) yes
C36 3_655 N31 C36 . 106.50(11) yes
C32 3_655 N31 C36 . 111.15(6) yes
C32 . N31 C36 . 110.09(6) yes
N31 . C32 C33 . 114.70(9) yes
N31 . C32 H321 . 105.9 no
C33 . C32 H321 . 111.2 no
N31 . C32 H322 . 104.1 no
C33 . C32 H322 . 113.0 no
H321 . C32 H322 . 107.4 no
C32 . C33 C34 . 113.34(10) yes
C32 . C33 H332 . 106.4 no
C34 . C33 H332 . 105.5 no
C32 . C33 H331 . 110.6 no
C34 . C33 H331 . 109.7 no
H332 . C33 H331 . 111.1 no
C33 . C34 C35 . 113.73(13) yes
C33 . C34 H342 . 107.5 no
C35 . C34 H342 . 111.6 no
C33 . C34 H341 . 111.6 no
C35 . C34 H341 . 112.0 no
H342 . C34 H341 . 99.4 no
C34 . C35 H352 . 113.0 no
C34 . C35 H353 . 107.3 no
H352 . C35 H353 . 105.1 no
C34 . C35 H351 . 113.1 no
H352 . C35 H351 . 107.6 no
H353 . C35 H351 . 110.3 no
N31 . C36 C37 . 115.26(9) yes
N31 . C36 H362 . 106.7 no
C37 . C36 H362 . 111.0 no
N31 . C36 H361 . 106.8 no
C37 . C36 H361 . 108.9 no
H362 . C36 H361 . 107.9 no
C36 . C37 C38 . 111.23(11) yes
C36 . C37 H372 . 109.7 no
C38 . C37 H372 . 108.5 no
C36 . C37 H371 . 110.6 no
C38 . C37 H371 . 110.2 no
H372 . C37 H371 . 106.5 no
C37 . C38 C39 . 113.43(13) yes
C37 . C38 H381 . 106.4 no
C39 . C38 H381 . 98.0 no
C37 . C38 H382 . 111.3 no
C39 . C38 H382 . 111.4 no
H381 . C38 H382 . 115.6 no
C38 . C39 H391 . 111.4 no
C38 . C39 H393 . 110.4 no
H391 . C39 H393 . 110.3 no
C38 . C39 H392 . 109.0 no
H391 . C39 H392 . 107.9 no
H393 . C39 H392 . 107.5 no
O41 . C42 C43 . 128.3(5) yes
O41 . C42 O44 . 121.3(3) yes
C43 . C42 O44 . 110.0(5) yes
C42 . C43 H431 . 112.3 no
C42 . C43 H432 . 110.1 no
H431 . C43 H432 . 107.8 no
C42 . C43 H433 . 108.4 no
H431 . C43 H433 . 107.6 no
H432 . C43 H433 . 110.6 no
C42 . O44 C45 . 116.2(2) yes
O44 . C45 C46 . 111.9(5) yes
O44 . C45 H452 . 110.7 no
C46 . C45 H452 . 113.1 no
O44 . C45 H451 . 106.8 no
C46 . C45 H451 . 109.9 no
H452 . C45 H451 . 104.2 no
C45 . C46 H462 . 108.5 no
C45 . C46 H461 . 108.2 no
H462 . C46 H461 . 109.1 no
C45 . C46 H463 . 108.7 no
H462 . C46 H463 . 111.7 no
H461 . C46 H463 . 110.5 no
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 C11 . 1.4218(12) yes
O1 H11 . 0.791 no
C11 C12 . 1.5300(14) yes
C11 C21 . 1.5251(14) yes
C11 H111 . 0.959 no
C12 C13 . 1.5153(15) yes
C12 O16 . 1.4339(13) yes
C12 H121 . 0.984 no
C13 O14 . 1.4287(15) yes
C13 H132 . 0.970 no
C13 H131 . 0.991 no
O14 C15 . 1.4294(17) yes
C15 O16 . 1.4407(14) yes
C15 C17 . 1.510(2) yes
C15 C18 . 1.517(2) yes
C17 H171 . 0.986 no
C17 H173 . 0.974 no
C17 H172 . 0.973 no
C18 H181 . 0.959 no
C18 H182 . 0.959 no
C18 H183 . 0.950 no
O2 C21 . 1.4214(12) yes
O2 H21 . 0.818 no
C21 C22 . 1.5186(14) yes
C21 H211 . 0.991 no
C22 C23 . 1.5263(15) yes
C22 O26 . 1.411(5) yes
C22 H221 . 0.985 no
C22 C23 . 1.5263(15) yes
C22 O126 . 1.444(4) yes
C22 H221 . 0.985 no
C23 O24 . 1.4193(15) yes
C23 H231 . 0.962 no
C23 H232 . 1.010 no
O24 C25 . 1.370(3) yes
O24 C125 . 1.439(2) yes
C25 O26 . 1.417(5) yes
C25 C27 . 1.522(4) yes
C25 C28 . 1.454(4) yes
C27 H271 . 0.959 no
C27 H273 . 0.960 no
C27 H272 . 0.960 no
C28 H22 . 0.963 no
C28 H282 . 0.962 no
C28 H283 . 0.971 no
C125 O126 . 1.423(4) yes
C125 C127 . 1.484(3) yes
C125 C128 . 1.529(3) yes
C127 H1271 . 0.970 no
C127 H1273 . 0.976 no
C127 H1272 . 0.975 no
C128 H1281 . 0.967 no
C128 H1282 . 0.977 no
C128 H1283 . 0.966 no
N31 C36 3_655 1.5219(12) yes
N31 C32 3_655 1.5213(12) yes
N31 C32 . 1.5213(12) yes
N31 C36 . 1.5219(12) yes
C32 C33 . 1.5167(16) yes
C32 H321 . 0.955 no
C32 H322 . 0.965 no
C33 C34 . 1.4827(18) yes
C33 H332 . 0.962 no
C33 H331 . 0.977 no
C34 C35 . 1.508(2) yes
C34 H342 . 0.997 no
C34 H341 . 0.969 no
C35 H352 . 0.960 no
C35 H353 . 0.941 no
C35 H351 . 0.964 no
C36 C37 . 1.5138(15) yes
C36 H362 . 0.957 no
C36 H361 . 0.956 no
C37 C38 . 1.5138(19) yes
C37 H372 . 0.976 no
C37 H371 . 0.994 no
C38 C39 . 1.509(2) yes
C38 H381 . 1.117 no
C38 H382 . 0.994 no
C39 H391 . 1.022 no
C39 H393 . 1.015 no
C39 H392 . 1.050 no
O41 C42 . 1.192(5) yes
C42 C43 . 1.502(6) yes
C42 O44 . 1.325(4) yes
C43 H431 . 0.947 no
C43 H432 . 0.980 no
C43 H433 . 0.960 no
O44 C45 . 1.440(4) yes
C45 C46 . 1.477(7) yes
C45 H452 . 0.962 no
C45 H451 . 0.976 no
C46 H462 . 0.969 no
C46 H461 . 0.962 no
C46 H463 . 0.971 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C36 . H362 O2 3_655 156.39 0.957 2.330 3.229(4) yes
C37 . H372 O41 3_646 166.84 0.976 2.364 3.321(4) yes
C43 . H431 O24 3_655 163.99 0.947 2.528 3.449(4) yes
C46 3_656 H431 O24 3_655 164.5 1.085 2.528 3.585(4) yes
O41 3_656 H452 C45 . 122.0 0.750 0.962 1.501(4) yes
C45 . H451 C28 1_556 151.12 0.976 2.568 3.455(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045670
