#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:13:32 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178462 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/83/4028352.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_4028352
loop_
_publ_author_name
'Thierry Brotin'
'Dominique Cavagnat'
'Erwann Jeanneau'
'Thierry Buffeteau'
_publ_section_title
;
 Synthesis of Highly Substituted Cryptophane Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6143
_journal_page_last               6153
_journal_paper_doi               10.1021/jo4007738
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C48 H56 O12'
_chemical_formula_sum            'C48 H56 O12'
_chemical_formula_weight         824.96
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                93.162(4)
_cell_angle_beta                 93.844(5)
_cell_angle_gamma                90.531(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7696(4)
_cell_length_b                   12.8766(7)
_cell_length_c                   21.5060(10)
_cell_measurement_reflns_used    11330
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.7984
_cell_measurement_theta_min      3.4350
_cell_volume                     2143.30(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_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    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) x-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31262
_diffrn_reflns_theta_full        66.844
_diffrn_reflns_theta_max         66.907
_diffrn_reflns_theta_min         3.438
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.733
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0325
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7573
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.0003527
_refine_ls_shift/su_mean         0.0000334
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 795. 0.120E+04 593. 137. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0799
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0799
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                6433
_reflns_number_total             7573
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.41
_oxford_diffrn_Wilson_scale      0.05
_oxford_refine_ls_r_factor_ref   0.0508
_oxford_refine_ls_scale          4.95(4)
_oxford_reflns_number_all        7573
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            jo4007738_si_001_1.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4028352
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (  10,X'S) H   ( 102,X'S) H   ( 101,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 203,X'S) H   ( 202,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) H   ( 293,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) H   ( 303,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) H   ( 313,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) 
RIDE C   (  40,X'S) H   ( 403,X'S) H   ( 402,X'S) H   ( 401,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) H   ( 432,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) H   ( 452,X'S) 
RIDE C   (  48,X'S) H   ( 483,X'S) H   ( 482,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 512,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) H   ( 562,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) H   ( 582,X'S) 
RIDE C   (  60,X'S) H   ( 603,X'S) H   ( 601,X'S) H   ( 602,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) H   ( 612,X'S) H   ( 613,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = C(29) TO C(30) 
DISTANCE 1.400000 , 0.010000 = O(28) TO C(30) 
END                                                                             
;
#END Tags that were not found in dictionaries
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67365(17) 0.67952(10) 0.33956(6) 0.0248 1.0000 Uani . . . .
C2 C 0.7718(2) 0.59796(14) 0.36055(8) 0.0221 1.0000 Uani . . . .
C3 C 0.9274(2) 0.57503(14) 0.33477(8) 0.0236 1.0000 Uani . . . .
O4 O 0.97803(17) 0.62983(10) 0.28552(6) 0.0274 1.0000 Uani . . . .
C5 C 1.1278(3) 0.69551(17) 0.30066(10) 0.0342 1.0000 Uani . . . .
C6 C 1.0971(3) 0.78117(17) 0.34701(11) 0.0397 1.0000 Uani . . . .
C7 C 1.2096(4) 0.80931(19) 0.39316(12) 0.0488 1.0000 Uani . . . .
H71 H 1.1812 0.8647 0.4221 0.0595 1.0000 Uiso R . . .
H72 H 1.3156 0.7730 0.3989 0.0604 1.0000 Uiso R . . .
H61 H 0.9926 0.8170 0.3413 0.0484 1.0000 Uiso R . . .
H52 H 1.2292 0.6526 0.3171 0.0408 1.0000 Uiso R . . .
H51 H 1.1556 0.7262 0.2610 0.0410 1.0000 Uiso R . . .
C8 C 1.0250(2) 0.49230(14) 0.35674(9) 0.0241 1.0000 Uani . . . .
O9 O 1.17181(17) 0.47063(10) 0.32678(6) 0.0297 1.0000 Uani . . . .
C10 C 1.2549(3) 0.37441(16) 0.33918(10) 0.0324 1.0000 Uani . . . .
H102 H 1.3465 0.3665 0.3104 0.0486 1.0000 Uiso R . . .
H101 H 1.3049 0.3749 0.3830 0.0481 1.0000 Uiso R . . .
H103 H 1.1723 0.3163 0.3310 0.0483 1.0000 Uiso R . . .
C11 C 0.9702(2) 0.43905(14) 0.40624(9) 0.0241 1.0000 Uani . . . .
C12 C 0.8153(2) 0.46372(14) 0.43294(8) 0.0225 1.0000 Uani . . . .
C13 C 0.7123(2) 0.54279(14) 0.40908(8) 0.0217 1.0000 Uani . . . .
C14 C 0.5378(2) 0.56861(14) 0.43280(8) 0.0222 1.0000 Uani . . . .
C15 C 0.5335(2) 0.65616(14) 0.48347(8) 0.0216 1.0000 Uani . . . .
C16 C 0.3919(2) 0.66669(14) 0.52048(8) 0.0219 1.0000 Uani . . . .
C17 C 0.2341(2) 0.59516(14) 0.51138(8) 0.0226 1.0000 Uani . . . .
H171 H 0.1356 0.6361 0.4988 0.0272 1.0000 Uiso R . . .
H172 H 0.2502 0.5428 0.4775 0.0260 1.0000 Uiso R . . .
C18 C 0.3921(2) 0.75039(14) 0.56458(8) 0.0233 1.0000 Uani . . . .
O19 O 0.25078(17) 0.76494(10) 0.59974(6) 0.0262 1.0000 Uani . . . .
C20 C 0.2840(3) 0.74288(16) 0.66428(9) 0.0316 1.0000 Uani . . . .
H201 H 0.1796 0.7542 0.6857 0.0462 1.0000 Uiso R . . .
H203 H 0.3773 0.7873 0.6842 0.0464 1.0000 Uiso R . . .
H202 H 0.3173 0.6700 0.6681 0.0460 1.0000 Uiso R . . .
C21 C 0.5259(3) 0.82348(14) 0.57161(8) 0.0239 1.0000 Uani . . . .
O22 O 0.52230(18) 0.90401(10) 0.61658(6) 0.0281 1.0000 Uani . . . .
C23 C 0.4399(3) 0.99492(15) 0.59443(10) 0.0333 1.0000 Uani . . . .
C24 C 0.4095(3) 1.06821(17) 0.64852(11) 0.0387 1.0000 Uani . . . .
C25 C 0.4385(3) 1.04823(19) 0.70728(11) 0.0452 1.0000 Uani . . . .
H251 H 0.4166 1.0996 0.7394 0.0541 1.0000 Uiso R . . .
H252 H 0.4814 0.9829 0.7200 0.0541 1.0000 Uiso R . . .
H241 H 0.3634 1.1337 0.6382 0.0459 1.0000 Uiso R . . .
H232 H 0.5146 1.0284 0.5666 0.0396 1.0000 Uiso R . . .
H231 H 0.3308 0.9752 0.5696 0.0402 1.0000 Uiso R . . .
C26 C 0.6651(3) 0.81258(14) 0.53438(9) 0.0253 1.0000 Uani . . . .
C27 C 0.6687(2) 0.72847(14) 0.49100(9) 0.0239 1.0000 Uani . . . .
H271 H 0.7625 0.7201 0.4653 0.0283 1.0000 Uiso R . . .
O28 O 0.78999(18) 0.88870(11) 0.54295(7) 0.0327 1.0000 Uani D . . .
C29 C 0.9427(3) 0.8707(2) 0.51145(13) 0.0354 0.8484 Uani . U 1 1
C30 C 0.9588(12) 0.8650(12) 0.5605(7) 0.0402 0.1516 Uani D U 1 2
H291 H 1.0228 0.9278 0.5245 0.0522 0.8484 Uiso R . 1 1
H292 H 0.9975 0.8046 0.5220 0.0523 0.8484 Uiso R . 1 1
H301 H 0.9997 0.8108 0.5327 0.0599 0.1516 Uiso R . 1 2
H302 H 1.0305 0.9260 0.5596 0.0599 0.1516 Uiso R . 1 2
H303 H 0.9632 0.8415 0.6022 0.0599 0.1516 Uiso R . 1 2
H293 H 0.9166 0.8709 0.4656 0.0521 0.8484 Uiso R . 1 1
H141 H 0.4912 0.5044 0.4487 0.0264 1.0000 Uiso R . . .
H142 H 0.4596 0.5881 0.3970 0.0263 1.0000 Uiso R . . .
H111 H 1.0366 0.3841 0.4220 0.0280 1.0000 Uiso R . . .
C31 C 0.5890(3) 0.65817(16) 0.27866(9) 0.0304 1.0000 Uani . . . .
H311 H 0.5170 0.7188 0.2683 0.0447 1.0000 Uiso R . . .
H312 H 0.5167 0.5953 0.2787 0.0456 1.0000 Uiso R . . .
H313 H 0.6736 0.6474 0.2472 0.0458 1.0000 Uiso R . . .
O32 O -0.24771(18) 0.34728(10) 0.15295(6) 0.0285 1.0000 Uani . . . .
C33 C -0.1020(3) 0.33263(14) 0.11990(9) 0.0258 1.0000 Uani . . . .
C34 C -0.1027(3) 0.36984(14) 0.05999(9) 0.0238 1.0000 Uani . . . .
C35 C 0.0410(3) 0.34767(14) 0.02509(9) 0.0243 1.0000 Uani . . . .
C36 C 0.0430(2) 0.38058(15) -0.04175(8) 0.0243 1.0000 Uani . . . .
C37 C 0.2170(2) 0.38394(15) -0.06918(8) 0.0239 1.0000 Uani . . . .
C38 C 0.2815(3) 0.29338(15) -0.09797(9) 0.0264 1.0000 Uani . . . .
O39 O 0.18621(19) 0.20247(10) -0.09713(7) 0.0336 1.0000 Uani . . . .
C40 C 0.1136(3) 0.1649(2) -0.15688(12) 0.0534 1.0000 Uani . . . .
H403 H 0.0358 0.1065 -0.1526 0.0790 1.0000 Uiso R . . .
H402 H 0.2012 0.1453 -0.1862 0.0802 1.0000 Uiso R . . .
H401 H 0.0408 0.2201 -0.1745 0.0792 1.0000 Uiso R . . .
C41 C 0.4389(3) 0.29234(15) -0.12518(9) 0.0265 1.0000 Uani . . . .
O42 O 0.49222(19) 0.20190(11) -0.15533(6) 0.0323 1.0000 Uani . . . .
C43 C 0.6432(3) 0.15419(18) -0.12702(11) 0.0433 1.0000 Uani . . . .
C44 C 0.6227(4) 0.12142(19) -0.06306(13) 0.0507 1.0000 Uani . . . .
C45 C 0.7453(4) 0.1271(2) -0.01720(14) 0.0615 1.0000 Uani . . . .
H451 H 0.8586 0.1597 -0.0227 0.0753 1.0000 Uiso R . . .
H452 H 0.7411 0.0949 0.0271 0.0735 1.0000 Uiso R . . .
H441 H 0.5074 0.0953 -0.0558 0.0608 1.0000 Uiso R . . .
H431 H 0.7454 0.2021 -0.1272 0.0522 1.0000 Uiso R . . .
H432 H 0.6606 0.0878 -0.1538 0.0516 1.0000 Uiso R . . .
C46 C 0.5323(3) 0.38527(15) -0.12589(8) 0.0254 1.0000 Uani . . . .
O47 O 0.68093(18) 0.37953(11) -0.15697(6) 0.0296 1.0000 Uani . . . .
C48 C 0.7631(3) 0.47633(16) -0.16811(10) 0.0319 1.0000 Uani . . . .
H483 H 0.8590 0.4603 -0.1937 0.0470 1.0000 Uiso R . . .
H482 H 0.8078 0.5128 -0.1292 0.0462 1.0000 Uiso R . . .
H481 H 0.6820 0.5221 -0.1903 0.0471 1.0000 Uiso R . . .
C49 C 0.4719(3) 0.47510(15) -0.09665(8) 0.0251 1.0000 Uani . . . .
C50 C 0.3161(2) 0.47543(15) -0.06772(8) 0.0238 1.0000 Uani . . . .
C51 C 0.2620(2) 0.57568(14) -0.03352(8) 0.0245 1.0000 Uani . . . .
H511 H 0.3590 0.6248 -0.0330 0.0287 1.0000 Uiso R . . .
H512 H 0.2465 0.5606 0.0102 0.0285 1.0000 Uiso R . . .
H491 H 0.5363 0.5372 -0.0962 0.0290 1.0000 Uiso R . . .
H362 H -0.0085 0.4501 -0.0449 0.0283 1.0000 Uiso R . . .
H361 H -0.0323 0.3334 -0.0679 0.0282 1.0000 Uiso R . . .
C52 C 0.1795(3) 0.29262(15) 0.05082(9) 0.0274 1.0000 Uani . . . .
C53 C 0.1780(3) 0.25681(15) 0.11035(9) 0.0288 1.0000 Uani . . . .
C54 C 0.0338(3) 0.27618(15) 0.14496(9) 0.0283 1.0000 Uani . . . .
O55 O 0.0298(2) 0.24148(11) 0.20437(6) 0.0339 1.0000 Uani . . . .
C56 C 0.0073(3) 0.13055(16) 0.20679(10) 0.0403 1.0000 Uani . . . .
C57 C 0.1144(3) 0.09580(18) 0.26146(13) 0.0478 1.0000 Uani . . . .
C58 C 0.0538(4) 0.0470(2) 0.30684(13) 0.0618 1.0000 Uani . . . .
H581 H 0.1322 0.0286 0.3416 0.0744 1.0000 Uiso R . . .
H582 H -0.0696 0.0275 0.3042 0.0737 1.0000 Uiso R . . .
H571 H 0.2356 0.1133 0.2620 0.0577 1.0000 Uiso R . . .
H561 H -0.1158 0.1148 0.2104 0.0469 1.0000 Uiso R . . .
H562 H 0.0433 0.0950 0.1684 0.0473 1.0000 Uiso R . . .
O59 O 0.3067(2) 0.20161(12) 0.13920(7) 0.0380 1.0000 Uani . . . .
C60 C 0.4476(3) 0.17098(18) 0.10342(11) 0.0405 1.0000 Uani . . . .
H603 H 0.5244 0.1279 0.1303 0.0609 1.0000 Uiso R . . .
H601 H 0.5120 0.2328 0.0913 0.0600 1.0000 Uiso R . . .
H602 H 0.4030 0.1292 0.0648 0.0602 1.0000 Uiso R . . .
H521 H 0.2755 0.2786 0.0266 0.0320 1.0000 Uiso R . . .
C61 C -0.2201(3) 0.41924(16) 0.20643(9) 0.0326 1.0000 Uani . . . .
H611 H -0.3264 0.4221 0.2272 0.0478 1.0000 Uiso R . . .
H612 H -0.1241 0.3957 0.2348 0.0479 1.0000 Uiso R . . .
H613 H -0.1922 0.4883 0.1926 0.0483 1.0000 Uiso R . . .
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'
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
C2 . O1 C31 . 113.46(14) yes
O1 . C2 C3 . 120.06(16) yes
O1 . C2 C13 . 117.96(16) yes
C3 . C2 C13 . 121.95(17) yes
C2 . C3 O4 . 119.70(17) yes
C2 . C3 C8 . 119.18(17) yes
O4 . C3 C8 . 121.00(16) yes
C3 . O4 C5 . 114.00(15) yes
O4 . C5 C6 . 112.99(17) yes
O4 . C5 H52 . 110.4 no
C6 . C5 H52 . 109.0 no
O4 . C5 H51 . 106.1 no
C6 . C5 H51 . 108.4 no
H52 . C5 H51 . 109.9 no
C5 . C6 C7 . 122.8(2) yes
C5 . C6 H61 . 116.6 no
C7 . C6 H61 . 120.5 no
C6 . C7 H71 . 118.8 no
C6 . C7 H72 . 120.5 no
H71 . C7 H72 . 120.6 no
C3 . C8 O9 . 115.88(16) yes
C3 . C8 C11 . 119.39(17) yes
O9 . C8 C11 . 124.73(17) yes
C8 . O9 C10 . 117.04(15) yes
O9 . C10 H102 . 106.7 no
O9 . C10 H101 . 111.2 no
H102 . C10 H101 . 109.9 no
O9 . C10 H103 . 110.0 no
H102 . C10 H103 . 109.1 no
H101 . C10 H103 . 109.9 no
C8 . C11 C12 . 121.21(18) yes
C8 . C11 H111 . 120.0 no
C12 . C11 H111 . 118.8 no
C17 2_666 C12 C11 . 118.51(16) yes
C17 2_666 C12 C13 . 121.72(16) yes
C11 . C12 C13 . 119.75(17) yes
C12 . C13 C2 . 118.39(17) yes
C12 . C13 C14 . 122.52(16) yes
C2 . C13 C14 . 119.08(16) yes
C13 . C14 C15 . 116.71(16) yes
C13 . C14 H141 . 107.2 no
C15 . C14 H141 . 108.9 no
C13 . C14 H142 . 108.5 no
C15 . C14 H142 . 107.4 no
H141 . C14 H142 . 107.8 no
C14 . C15 C16 . 120.67(17) yes
C14 . C15 C27 . 119.23(16) yes
C16 . C15 C27 . 120.04(17) yes
C15 . C16 C17 . 122.67(16) yes
C15 . C16 C18 . 118.20(17) yes
C17 . C16 C18 . 119.00(16) yes
C16 . C17 C12 2_666 117.50(16) yes
C16 . C17 H171 . 108.5 no
C12 2_666 C17 H171 . 106.8 no
C16 . C17 H172 . 109.6 no
C12 2_666 C17 H172 . 106.6 no
H171 . C17 H172 . 107.4 no
C16 . C18 O19 . 119.27(17) yes
C16 . C18 C21 . 121.85(17) yes
O19 . C18 C21 . 118.76(16) yes
C18 . O19 C20 . 113.59(15) yes
O19 . C20 H201 . 108.8 no
O19 . C20 H203 . 111.1 no
H201 . C20 H203 . 109.8 no
O19 . C20 H202 . 110.7 no
H201 . C20 H202 . 108.2 no
H203 . C20 H202 . 108.2 no
C18 . C21 O22 . 119.92(17) yes
C18 . C21 C26 . 119.42(17) yes
O22 . C21 C26 . 120.63(17) yes
C21 . O22 C23 . 113.39(15) yes
O22 . C23 C24 . 109.25(18) yes
O22 . C23 H232 . 109.2 no
C24 . C23 H232 . 109.3 no
O22 . C23 H231 . 110.0 no
C24 . C23 H231 . 111.9 no
H232 . C23 H231 . 107.1 no
C23 . C24 C25 . 125.2(2) yes
C23 . C24 H241 . 115.4 no
C25 . C24 H241 . 119.4 no
C24 . C25 H251 . 120.2 no
C24 . C25 H252 . 122.4 no
H251 . C25 H252 . 117.3 no
C21 . C26 C27 . 119.51(18) yes
C21 . C26 O28 . 116.13(17) yes
C27 . C26 O28 . 124.35(17) yes
C15 . C27 C26 . 120.95(17) yes
C15 . C27 H271 . 118.6 no
C26 . C27 H271 . 120.5 no
C26 . O28 C29 . 116.20(16) yes
C26 . O28 C30 . 121.1(7) yes
O28 . C29 H291 . 107.1 no
O28 . C29 H292 . 112.3 no
H291 . C29 H292 . 108.7 no
O28 . C29 H293 . 110.1 no
H291 . C29 H293 . 108.9 no
H292 . C29 H293 . 109.6 no
O28 . C30 H301 . 110.3 no
O28 . C30 H302 . 109.6 no
H301 . C30 H302 . 109.7 no
O28 . C30 H303 . 108.4 no
H301 . C30 H303 . 109.3 no
H302 . C30 H303 . 109.4 no
O1 . C31 H311 . 108.1 no
O1 . C31 H312 . 109.7 no
H311 . C31 H312 . 110.2 no
O1 . C31 H313 . 110.8 no
H311 . C31 H313 . 109.2 no
H312 . C31 H313 . 108.7 no
C33 . O32 C61 . 113.26(15) yes
O32 . C33 C34 . 118.25(18) yes
O32 . C33 C54 . 119.53(17) yes
C34 . C33 C54 . 122.07(18) yes
C51 2_565 C34 C33 . 119.23(17) yes
C51 2_565 C34 C35 . 122.92(17) yes
C33 . C34 C35 . 117.66(18) yes
C34 . C35 C36 . 120.08(18) yes
C34 . C35 C52 . 120.29(17) yes
C36 . C35 C52 . 119.60(17) yes
C35 . C36 C37 . 116.62(17) yes
C35 . C36 H362 . 109.6 no
C37 . C36 H362 . 107.7 no
C35 . C36 H361 . 107.8 no
C37 . C36 H361 . 108.7 no
H362 . C36 H361 . 105.9 no
C36 . C37 C38 . 119.57(17) yes
C36 . C37 C50 . 122.09(17) yes
C38 . C37 C50 . 118.34(17) yes
C37 . C38 O39 . 118.02(17) yes
C37 . C38 C41 . 122.11(17) yes
O39 . C38 C41 . 119.84(17) yes
C38 . O39 C40 . 114.15(17) yes
O39 . C40 H403 . 110.2 no
O39 . C40 H402 . 113.1 no
H403 . C40 H402 . 110.3 no
O39 . C40 H401 . 108.3 no
H403 . C40 H401 . 105.6 no
H402 . C40 H401 . 109.0 no
C38 . C41 O42 . 119.51(17) yes
C38 . C41 C46 . 118.83(17) yes
O42 . C41 C46 . 121.44(17) yes
C41 . O42 C43 . 115.97(16) yes
O42 . C43 C44 . 114.1(2) yes
O42 . C43 H431 . 110.0 no
C44 . C43 H431 . 110.1 no
O42 . C43 H432 . 105.5 no
C44 . C43 H432 . 106.2 no
H431 . C43 H432 . 110.8 no
C43 . C44 C45 . 124.8(3) yes
C43 . C44 H441 . 114.8 no
C45 . C44 H441 . 120.3 no
C44 . C45 H451 . 121.1 no
C44 . C45 H452 . 126.8 no
H451 . C45 H452 . 112.0 no
C41 . C46 O47 . 115.52(17) yes
C41 . C46 C49 . 119.73(17) yes
O47 . C46 C49 . 124.74(17) yes
C46 . O47 C48 . 116.69(15) yes
O47 . C48 H483 . 107.2 no
O47 . C48 H482 . 111.7 no
H483 . C48 H482 . 108.8 no
O47 . C48 H481 . 110.8 no
H483 . C48 H481 . 109.5 no
H482 . C48 H481 . 108.7 no
C46 . C49 C50 . 121.35(18) yes
C46 . C49 H491 . 119.7 no
C50 . C49 H491 . 118.9 no
C37 . C50 C49 . 119.54(17) yes
C37 . C50 C51 . 121.90(17) yes
C49 . C50 C51 . 118.53(17) yes
C50 . C51 C34 2_565 117.76(16) yes
C50 . C51 H511 . 107.1 no
C34 2_565 C51 H511 . 107.3 no
C50 . C51 H512 . 108.1 no
C34 2_565 C51 H512 . 109.2 no
H511 . C51 H512 . 107.0 no
C35 . C52 C53 . 121.15(18) yes
C35 . C52 H521 . 119.0 no
C53 . C52 H521 . 119.8 no
C52 . C53 C54 . 119.07(19) yes
C52 . C53 O59 . 125.33(18) yes
C54 . C53 O59 . 115.59(17) yes
C53 . C54 C33 . 119.73(18) yes
C53 . C54 O55 . 120.03(19) yes
C33 . C54 O55 . 120.22(18) yes
C54 . O55 C56 . 114.56(15) yes
O55 . C56 C57 . 108.23(19) yes
O55 . C56 H561 . 108.9 no
C57 . C56 H561 . 111.3 no
O55 . C56 H562 . 110.3 no
C57 . C56 H562 . 109.9 no
H561 . C56 H562 . 108.3 no
C56 . C57 C58 . 124.2(3) yes
C56 . C57 H571 . 115.2 no
C58 . C57 H571 . 120.6 no
C57 . C58 H581 . 119.2 no
C57 . C58 H582 . 118.8 no
H581 . C58 H582 . 122.0 no
C53 . O59 C60 . 117.42(17) yes
O59 . C60 H603 . 106.9 no
O59 . C60 H601 . 110.7 no
H603 . C60 H601 . 109.9 no
O59 . C60 H602 . 109.5 no
H603 . C60 H602 . 110.4 no
H601 . C60 H602 . 109.3 no
O32 . C61 H611 . 107.2 no
O32 . C61 H612 . 110.4 no
H611 . C61 H612 . 110.8 no
O32 . C61 H613 . 109.5 no
H611 . C61 H613 . 109.6 no
H612 . C61 H613 . 109.4 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 C2 . 1.382(2) yes
O1 C31 . 1.437(2) yes
C2 C3 . 1.391(3) yes
C2 C13 . 1.396(3) yes
C3 O4 . 1.381(2) yes
C3 C8 . 1.398(3) yes
O4 C5 . 1.441(2) yes
C5 C6 . 1.477(3) yes
C5 H52 . 1.022 no
C5 H51 . 0.996 no
C6 C7 . 1.311(3) yes
C6 H61 . 0.942 no
C7 H71 . 0.957 no
C7 H72 . 0.955 no
C8 O9 . 1.371(2) yes
C8 C11 . 1.386(3) yes
O9 C10 . 1.432(2) yes
C10 H102 . 0.976 no
C10 H101 . 0.996 no
C10 H103 . 0.982 no
C11 C12 . 1.400(3) yes
C11 H111 . 0.945 no
C12 C17 2_666 1.521(2) yes
C12 C13 . 1.399(3) yes
C13 C14 . 1.514(2) yes
C14 C15 . 1.526(2) yes
C14 H141 . 0.987 no
C14 H142 . 0.993 no
C15 C16 . 1.404(3) yes
C15 C27 . 1.393(3) yes
C16 C17 . 1.522(3) yes
C16 C18 . 1.396(3) yes
C17 H171 . 0.965 no
C17 H172 . 0.980 no
C18 O19 . 1.383(2) yes
C18 C21 . 1.391(3) yes
O19 C20 . 1.439(2) yes
C20 H201 . 0.967 no
C20 H203 . 0.980 no
C20 H202 . 0.982 no
C21 O22 . 1.380(2) yes
C21 C26 . 1.392(3) yes
O22 C23 . 1.429(2) yes
C23 C24 . 1.490(3) yes
C23 H232 . 0.974 no
C23 H231 . 0.994 no
C24 C25 . 1.309(3) yes
C24 H241 . 0.951 no
C25 H251 . 0.954 no
C25 H252 . 0.955 no
C26 C27 . 1.392(3) yes
C26 O28 . 1.369(2) yes
C27 H271 . 0.947 no
O28 C29 . 1.420(3) yes
O28 C30 . 1.382(8) yes
C29 H291 . 0.977 no
C29 H292 . 0.985 no
C29 H293 . 0.993 no
C30 H301 . 0.964 no
C30 H302 . 0.961 no
C30 H303 . 0.960 no
C31 H311 . 0.991 no
C31 H312 . 0.981 no
C31 H313 . 0.979 no
O32 C33 . 1.385(2) yes
O32 C61 . 1.440(2) yes
C33 C34 . 1.399(3) yes
C33 C54 . 1.383(3) yes
C34 C51 2_565 1.521(3) yes
C34 C35 . 1.409(3) yes
C35 C36 . 1.522(2) yes
C35 C52 . 1.395(3) yes
C36 C37 . 1.512(3) yes
C36 H362 . 0.987 no
C36 H361 . 0.969 no
C37 C38 . 1.403(3) yes
C37 C50 . 1.399(3) yes
C38 O39 . 1.381(2) yes
C38 C41 . 1.390(3) yes
O39 C40 . 1.426(3) yes
C40 H403 . 0.973 no
C40 H402 . 0.984 no
C40 H401 . 0.989 no
C41 O42 . 1.382(2) yes
C41 C46 . 1.395(3) yes
O42 C43 . 1.443(3) yes
C43 C44 . 1.479(3) yes
C43 H431 . 1.001 no
C43 H432 . 1.019 no
C44 C45 . 1.323(4) yes
C44 H441 . 0.979 no
C45 H451 . 0.989 no
C45 H452 . 1.062 no
C46 O47 . 1.373(2) yes
C46 C49 . 1.387(3) yes
O47 C48 . 1.434(2) yes
C48 H483 . 0.972 no
C48 H482 . 0.978 no
C48 H481 . 0.986 no
C49 C50 . 1.397(3) yes
C49 H491 . 0.939 no
C50 C51 . 1.527(2) yes
C51 H511 . 0.979 no
C51 H512 . 0.985 no
C52 C53 . 1.385(3) yes
C52 H521 . 0.952 no
C53 C54 . 1.403(3) yes
C53 O59 . 1.367(3) yes
C54 O55 . 1.379(2) yes
O55 C56 . 1.442(2) yes
C56 C57 . 1.486(3) yes
C56 H561 . 0.985 no
C56 H562 . 0.980 no
C57 C58 . 1.301(4) yes
C57 H571 . 0.965 no
C58 H581 . 0.973 no
C58 H582 . 0.986 no
O59 C60 . 1.426(3) yes
C60 H603 . 0.996 no
C60 H601 . 0.992 no
C60 H602 . 1.004 no
C61 H611 . 0.965 no
C61 H612 . 0.992 no
C61 H613 . 0.980 no
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C25 H251 O42 1_566 153.02(7) 0.954 2.586 3.463(3) yes
C24 H241 O1 2_676 151.56(7) 0.951 2.450 3.317(3) yes
C29 H292 O19 1_655 131.47(6) 0.985 2.569 3.305(3) yes
C29 H301 O19 1_655 143.0(11) 1.008 2.444 3.305(3) yes
C30 H303 C58 2_666 124.1(4) 0.960 2.375 3.020(3) yes
C14 H141 C16 2_666 136.44(6) 0.987 2.497 3.283(3) yes
C36 H362 C34 2_565 135.59(6) 0.987 2.512 3.291(3) yes
