#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:40:31 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270493 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158301.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_7158301
loop_
_publ_author_name
'Rithchumpon, Puracheth'
'Intakaew, Neeranuth'
'Khamto, Nopawit'
'Yimklan, Saranpong'
'Nimmanpipug, Piyarat'
'Thavornyutikarn, Praput'
'Meepowpan, Puttinan'
_publ_section_title
;
Synthesis and application of methyl itaconate-anthracene adducts in
configuration assignment of chiral secondary alcohols by 1H
NMR.
;
_journal_issue 41
_journal_name_full 'Organic & biomolecular chemistry'
_journal_page_first 8955
_journal_page_last 8967
_journal_paper_doi 10.1039/d1ob01387d
_journal_volume 19
_journal_year 2021
_chemical_absolute_configuration rm
_chemical_formula_moiety 'C24 H26 O4'
_chemical_formula_sum 'C24 H26 O4'
_chemical_formula_weight 378.45
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_Hall 'P 2ac 2ab'
_space_group_name_H-M_alt 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_date 2021-07-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-02 deposited with the CCDC. 2021-09-16 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 10.0685(3)
_cell_length_b 10.1743(3)
_cell_length_c 20.3368(6)
_cell_measurement_reflns_used 8934
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 25.9420
_cell_measurement_theta_min 2.2370
_cell_volume 2083.30(11)
_computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_type HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -72.00 3.00 0.50 8.00 -- -9.67 -42.00 -1.00 150
2 \w -44.00 36.00 0.50 8.00 -- 10.38 -79.00-156.00 160
3 \w -21.00 54.00 0.50 8.00 -- -9.67 37.00 -60.00 150
4 \w -56.00 -9.00 0.50 8.00 -- -9.67 125.00 30.00 94
5 \w -47.00 -19.00 0.50 8.00 -- -9.67 124.00-147.00 56
6 \w -51.00 -7.00 0.50 8.00 -- -9.67 -57.00 150.00 88
7 \w -52.00 22.00 0.50 8.00 -- 10.38 -42.00 -1.00 148
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0097203000
_diffrn_orient_matrix_UB_12 0.0054350000
_diffrn_orient_matrix_UB_13 -0.0344413000
_diffrn_orient_matrix_UB_21 -0.0354611000
_diffrn_orient_matrix_UB_22 0.0594954000
_diffrn_orient_matrix_UB_23 0.0047703000
_diffrn_orient_matrix_UB_31 0.0600820000
_diffrn_orient_matrix_UB_32 0.0359329000
_diffrn_orient_matrix_UB_33 -0.0027704000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0466
_diffrn_reflns_av_unetI/netI 0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_number 16394
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.426
_diffrn_reflns_theta_min 2.238
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu 0.081
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.31744
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour 'clear light colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.207
_exptl_crystal_description block
_exptl_crystal_F_000 808
_exptl_crystal_size_max 0.4
_exptl_crystal_size_mid 0.4
_exptl_crystal_size_min 0.3
_refine_diff_density_max 0.265
_refine_diff_density_min -0.176
_refine_diff_density_rms 0.047
_refine_ls_abs_structure_details
;
Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.3(6)
_refine_ls_extinction_coef 0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref 1.029
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 257
_refine_ls_number_reflns 4382
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.029
_refine_ls_R_factor_all 0.0760
_refine_ls_R_factor_gt 0.0523
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0812P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1299
_refine_ls_wR_factor_ref 0.1456
_reflns_Friedel_coverage 0.727
_reflns_Friedel_fraction_full 0.987
_reflns_Friedel_fraction_max 0.899
_reflns_number_gt 3034
_reflns_number_total 4382
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d1ob01387d2.cif
_cod_data_source_block pm02as230519
_cod_depositor_comments
'Adding full bibliography for 7158301--7158304.cif.'
_cod_database_code 7158301
_shelx_shelxl_version_number 2018/3
_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_max 0.976
_shelx_estimated_absorpt_t_min 0.968
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 26.32
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C9(H9), C10(H10), C1'(H1')
2.b Secondary CH2 refined with riding coordinates:
C13(H13A,H13B), C12(H12A,H12B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
C8(H8), C5(H5), C4(H4), C7(H7), C1(H1), C6(H6), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
C15(H15A,H15B,H15C), C2'(H2'A,H2'B,H2'C), C4'(H4'A,H4'B,H4'C)
;
_shelx_res_file
;
TITL pm02as230519_a.res in P2(1)2(1)2(1)
pm02as230519.res
created by SHELXL-2018/3 at 00:30:21 on 03-Jul-2021
REM Old TITL pm02as230519_a.res in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1): R1 0.183, Rweak 0.021, Alpha 0.001
REM 0.649 for 24 systematic absences, Orientation as input
REM Flack x = 0.292 ( 0.841 ) from 1074 Parsons' quotients
REM Formula found by SHELXT: C24 O4
CELL 0.71073 10.0685 10.1743 20.3368 90 90 90
ZERR 4 0.0003 0.0003 0.0006 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H O
UNIT 96 104 16
L.S. 10 0 0
PLAN 4
SIZE 0.3 0.4 0.4
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
OMIT 0 1 2
OMIT -1 -1 -1
OMIT 0 0 2
OMIT 1 0 2
OMIT 1 4 0
OMIT 3 0 1
OMIT 9 0 8
OMIT 0 6 4
OMIT 1 0 3
OMIT 3 0 5
OMIT 1 4 4
OMIT 0 8 2
REM
REM
REM
WGHT 0.081200
EXTI 0.009867
FVAR 0.40705
O4 3 0.069356 0.447403 0.457164 11.00000 0.03835 0.08629 =
0.06901 -0.00913 -0.01022 0.00048
O2 3 0.352589 0.510943 0.659828 11.00000 0.06723 0.06650 =
0.05109 -0.00391 0.00318 -0.00779
O1 3 0.334270 0.307095 0.620128 11.00000 0.08162 0.05900 =
0.07266 0.00484 0.00513 -0.01131
O3 3 0.107198 0.505835 0.560574 11.00000 0.04659 0.13160 =
0.07293 -0.02741 -0.00100 0.01560
C14 1 0.147057 0.465575 0.509422 11.00000 0.03746 0.05154 =
0.05999 -0.00222 -0.00033 -0.00123
C8A 1 0.566214 0.465066 0.458480 11.00000 0.02942 0.06001 =
0.05244 -0.00431 -0.00442 0.00732
C11 1 0.390447 0.476781 0.544363 11.00000 0.03148 0.04880 =
0.05018 -0.00448 -0.00042 -0.00022
C16 1 0.354585 0.422483 0.611643 11.00000 0.03611 0.05615 =
0.05625 -0.00073 -0.00408 -0.00313
C5A 1 0.577131 0.601263 0.455734 11.00000 0.03577 0.06347 =
0.04768 0.00348 -0.00200 0.00339
C13 1 0.287692 0.424907 0.495046 11.00000 0.03898 0.06072 =
0.05815 -0.00915 -0.00460 0.00478
AFIX 23
H13A 2 0.311376 0.455790 0.451471 11.00000 -1.20000
H13B 2 0.292090 0.329674 0.494522 11.00000 -1.20000
AFIX 0
C1A 1 0.629823 0.467730 0.573305 11.00000 0.03272 0.07698 =
0.04396 -0.00022 0.00472 0.00223
C9 1 0.549099 0.665484 0.520813 11.00000 0.04949 0.05006 =
0.05374 0.00043 0.00277 -0.00590
AFIX 13
H9 2 0.560765 0.761002 0.518534 11.00000 -1.20000
AFIX 0
C4A 1 0.641806 0.604100 0.570678 11.00000 0.04105 0.07378 =
0.04647 -0.00349 0.00476 -0.00915
C8 1 0.611445 0.662233 0.397488 11.00000 0.05269 0.07781 =
0.05519 0.00772 -0.00271 0.00022
AFIX 43
H8 2 0.618801 0.753246 0.395324 11.00000 -1.20000
AFIX 0
C12 1 0.405676 0.628221 0.541133 11.00000 0.04290 0.04939 =
0.05836 -0.00139 0.00364 0.00292
AFIX 23
H12A 2 0.343262 0.663830 0.509466 11.00000 -1.20000
H12B 2 0.385650 0.665991 0.583790 11.00000 -1.20000
AFIX 0
C5 1 0.588146 0.388722 0.402372 11.00000 0.04760 0.07738 =
0.06015 -0.01445 -0.00515 0.01367
AFIX 43
H5 2 0.578980 0.297802 0.403647 11.00000 -1.20000
AFIX 0
C10 1 0.528996 0.414295 0.526099 11.00000 0.03582 0.04674 =
0.05678 -0.00212 0.00230 0.00551
AFIX 13
H10 2 0.525899 0.318048 0.527206 11.00000 -1.20000
AFIX 0
C4 1 0.709166 0.393938 0.615790 11.00000 0.04623 0.09995 =
0.05120 0.00879 0.00275 0.01167
AFIX 43
H4 2 0.699956 0.303155 0.618562 11.00000 -1.20000
AFIX 0
C7 1 0.634778 0.585584 0.342239 11.00000 0.07049 0.10569 =
0.04706 0.00705 0.00186 0.00539
AFIX 43
H7 2 0.658188 0.625845 0.302854 11.00000 -1.20000
AFIX 0
C15 1 -0.071560 0.474831 0.465712 11.00000 0.03588 0.08495 =
0.10118 -0.00503 -0.01594 0.00438
AFIX 137
H15A 2 -0.122263 0.420194 0.436540 11.00000 -1.50000
H15B 2 -0.088581 0.565571 0.455890 11.00000 -1.50000
H15C 2 -0.096721 0.456806 0.510342 11.00000 -1.50000
AFIX 0
C1 1 0.734025 0.667847 0.610230 11.00000 0.06315 0.10052 =
0.05728 -0.00719 0.00506 -0.03178
AFIX 43
H1 2 0.741160 0.758965 0.609397 11.00000 -1.20000
AFIX 0
C6 1 0.623900 0.452325 0.344853 11.00000 0.06147 0.11275 =
0.04973 -0.01701 0.00079 0.01482
AFIX 43
H6 2 0.640818 0.403041 0.307261 11.00000 -1.20000
AFIX 0
C3 1 0.802577 0.460279 0.653926 11.00000 0.04803 0.15444 =
0.05107 0.01999 -0.00850 -0.00429
AFIX 43
H3 2 0.857391 0.412635 0.681973 11.00000 -1.20000
AFIX 0
C1' 1 0.315121 0.465700 0.726234 11.00000 0.08023 0.09670 =
0.05015 0.00035 0.00308 -0.01148
AFIX 13
H1' 2 0.348591 0.376432 0.733518 11.00000 -1.20000
AFIX 0
C2 1 0.815340 0.593820 0.650986 11.00000 0.06362 0.15296 =
0.05270 0.00149 -0.01263 -0.03336
AFIX 43
H2 2 0.879221 0.635553 0.676580 11.00000 -1.20000
AFIX 0
C3' 1 0.380171 0.558264 0.772726 11.00000 0.15114 0.22729 =
0.06600 -0.02512 0.00561 -0.04569
AFIX 23
H3'A 2 0.348693 0.646270 0.763053 11.00000 -1.20000
H3'B 2 0.351001 0.536663 0.816881 11.00000 -1.20000
AFIX 0
C2' 1 0.166204 0.466822 0.731401 11.00000 0.09443 0.24237 =
0.10148 0.01456 0.03991 0.00566
AFIX 137
H2'A 2 0.135007 0.555983 0.731241 11.00000 -1.50000
H2'B 2 0.139704 0.424744 0.771563 11.00000 -1.50000
H2'C 2 0.128791 0.420456 0.694697 11.00000 -1.50000
AFIX 0
C4' 1 0.520463 0.560305 0.772292 11.00000 0.11786 0.33536 =
0.10849 -0.05058 -0.00865 -0.07167
AFIX 137
H4'A 2 0.551165 0.599081 0.732031 11.00000 -1.50000
H4'B 2 0.553602 0.472090 0.775670 11.00000 -1.50000
H4'C 2 0.551956 0.611130 0.808880 11.00000 -1.50000
AFIX 0
HKLF 4
REM pm02as230519_a.res in P2(1)2(1)2(1)
REM wR2 = 0.1456, GooF = S = 1.029, Restrained GooF = 1.029 for all data
REM R1 = 0.0523 for 3034 Fo > 4sig(Fo) and 0.0760 for all 4382 data
REM 257 parameters refined using 0 restraints
END
WGHT 0.0812 0.0000
REM Highest difference peak 0.265, deepest hole -0.176, 1-sigma level 0.047
Q1 1 0.4541 0.4650 0.7656 11.00000 0.05 0.27
Q2 1 -0.0768 0.5604 0.5111 11.00000 0.05 0.19
Q3 1 -0.2065 0.4578 0.3785 11.00000 0.05 0.17
Q4 1 0.2342 0.5933 0.7620 11.00000 0.05 0.16
;
_shelx_res_checksum 40971
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.688
_oxdiff_exptl_absorpt_empirical_full_min 0.468
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.06936(19) 0.4474(2) 0.45716(11) 0.0646(6) Uani 1 1 d . . . . .
O2 O 0.3526(2) 0.51094(19) 0.65983(10) 0.0616(6) Uani 1 1 d . . . . .
O1 O 0.3343(2) 0.3071(2) 0.62013(11) 0.0711(7) Uani 1 1 d . . . . .
O3 O 0.1072(2) 0.5058(3) 0.56057(12) 0.0837(8) Uani 1 1 d . . . . .
C14 C 0.1471(3) 0.4656(3) 0.50942(15) 0.0497(7) Uani 1 1 d . . . . .
C8A C 0.5662(2) 0.4651(3) 0.45848(14) 0.0473(7) Uani 1 1 d . . . . .
C11 C 0.3904(2) 0.4768(3) 0.54436(13) 0.0435(6) Uani 1 1 d . . . . .
C16 C 0.3546(3) 0.4225(3) 0.61164(14) 0.0495(7) Uani 1 1 d . . . . .
C5A C 0.5771(3) 0.6013(3) 0.45573(14) 0.0490(7) Uani 1 1 d . . . . .
C13 C 0.2877(3) 0.4249(3) 0.49505(14) 0.0526(8) Uani 1 1 d . . . . .
H13A H 0.311376 0.455790 0.451471 0.063 Uiso 1 1 calc R U . . .
H13B H 0.292090 0.329674 0.494522 0.063 Uiso 1 1 calc R U . . .
C1A C 0.6298(3) 0.4677(3) 0.57330(13) 0.0512(7) Uani 1 1 d . . . . .
C9 C 0.5491(3) 0.6655(3) 0.52081(15) 0.0511(8) Uani 1 1 d . . . . .
H9 H 0.560765 0.761002 0.518534 0.061 Uiso 1 1 calc R U . . .
C4A C 0.6418(3) 0.6041(3) 0.57068(14) 0.0538(8) Uani 1 1 d . . . . .
C8 C 0.6114(3) 0.6622(4) 0.39749(15) 0.0619(9) Uani 1 1 d . . . . .
H8 H 0.618801 0.753246 0.395324 0.074 Uiso 1 1 calc R U . . .
C12 C 0.4057(3) 0.6282(3) 0.54113(15) 0.0502(7) Uani 1 1 d . . . . .
H12A H 0.343262 0.663830 0.509466 0.060 Uiso 1 1 calc R U . . .
H12B H 0.385650 0.665991 0.583790 0.060 Uiso 1 1 calc R U . . .
C5 C 0.5881(3) 0.3887(4) 0.40237(16) 0.0617(9) Uani 1 1 d . . . . .
H5 H 0.578980 0.297802 0.403647 0.074 Uiso 1 1 calc R U . . .
C10 C 0.5290(3) 0.4143(3) 0.52610(14) 0.0464(7) Uani 1 1 d . . . . .
H10 H 0.525899 0.318048 0.527206 0.056 Uiso 1 1 calc R U . . .
C4 C 0.7092(3) 0.3939(4) 0.61579(15) 0.0658(9) Uani 1 1 d . . . . .
H4 H 0.699956 0.303155 0.618562 0.079 Uiso 1 1 calc R U . . .
C7 C 0.6348(4) 0.5856(4) 0.34224(17) 0.0744(10) Uani 1 1 d . . . . .
H7 H 0.658188 0.625845 0.302854 0.089 Uiso 1 1 calc R U . . .
C15 C -0.0716(3) 0.4748(4) 0.4657(2) 0.0740(10) Uani 1 1 d . . . . .
H15A H -0.122263 0.420194 0.436540 0.111 Uiso 1 1 calc R U . . .
H15B H -0.088581 0.565571 0.455890 0.111 Uiso 1 1 calc R U . . .
H15C H -0.096721 0.456806 0.510342 0.111 Uiso 1 1 calc R U . . .
C1 C 0.7340(4) 0.6678(4) 0.61023(16) 0.0736(11) Uani 1 1 d . . . . .
H1 H 0.741160 0.758965 0.609397 0.088 Uiso 1 1 calc R U . . .
C6 C 0.6239(3) 0.4523(4) 0.34485(17) 0.0747(10) Uani 1 1 d . . . . .
H6 H 0.640818 0.403041 0.307261 0.090 Uiso 1 1 calc R U . . .
C3 C 0.8026(4) 0.4603(5) 0.65393(17) 0.0845(12) Uani 1 1 d . . . . .
H3 H 0.857391 0.412635 0.681973 0.101 Uiso 1 1 calc R U . . .
C1' C 0.3151(4) 0.4657(4) 0.72623(16) 0.0757(10) Uani 1 1 d . . . . .
H1' H 0.348591 0.376432 0.733518 0.091 Uiso 1 1 calc R U . . .
C2 C 0.8153(4) 0.5938(5) 0.65099(18) 0.0898(13) Uani 1 1 d . . . . .
H2 H 0.879221 0.635553 0.676580 0.108 Uiso 1 1 calc R U . . .
C3' C 0.3802(7) 0.5583(8) 0.7727(2) 0.148(2) Uani 1 1 d . . . . .
H3'A H 0.348693 0.646270 0.763053 0.178 Uiso 1 1 calc R U . . .
H3'B H 0.351001 0.536663 0.816881 0.178 Uiso 1 1 calc R U . . .
C2' C 0.1662(5) 0.4668(7) 0.7314(3) 0.146(2) Uani 1 1 d . . . . .
H2'A H 0.135007 0.555983 0.731241 0.219 Uiso 1 1 calc R U . . .
H2'B H 0.139704 0.424744 0.771563 0.219 Uiso 1 1 calc R U . . .
H2'C H 0.128791 0.420456 0.694697 0.219 Uiso 1 1 calc R U . . .
C4' C 0.5205(7) 0.5603(9) 0.7723(3) 0.187(3) Uani 1 1 d . . . . .
H4'A H 0.551165 0.599081 0.732031 0.281 Uiso 1 1 calc R U . . .
H4'B H 0.553602 0.472090 0.775670 0.281 Uiso 1 1 calc R U . . .
H4'C H 0.551956 0.611130 0.808880 0.281 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0383(11) 0.0863(16) 0.0690(14) -0.0091(12) -0.0102(10) 0.0005(11)
O2 0.0672(14) 0.0665(13) 0.0511(12) -0.0039(11) 0.0032(11) -0.0078(11)
O1 0.0816(17) 0.0590(14) 0.0727(15) 0.0048(11) 0.0051(13) -0.0113(13)
O3 0.0466(12) 0.132(2) 0.0729(16) -0.0274(15) -0.0010(11) 0.0156(14)
C14 0.0375(14) 0.0515(16) 0.0600(18) -0.0022(15) -0.0003(14) -0.0012(14)
C8A 0.0294(13) 0.0600(18) 0.0524(17) -0.0043(15) -0.0044(11) 0.0073(14)
C11 0.0315(13) 0.0488(15) 0.0502(16) -0.0045(14) -0.0004(11) -0.0002(12)
C16 0.0361(14) 0.0561(18) 0.0562(18) -0.0007(15) -0.0041(13) -0.0031(14)
C5A 0.0358(14) 0.0635(19) 0.0477(17) 0.0035(15) -0.0020(12) 0.0034(14)
C13 0.0390(14) 0.0607(19) 0.0582(18) -0.0091(14) -0.0046(13) 0.0048(14)
C1A 0.0327(13) 0.077(2) 0.0440(15) -0.0002(16) 0.0047(12) 0.0022(15)
C9 0.0495(17) 0.0501(17) 0.0537(18) 0.0004(14) 0.0028(14) -0.0059(14)
C4A 0.0410(16) 0.074(2) 0.0465(17) -0.0035(15) 0.0048(13) -0.0092(16)
C8 0.0527(19) 0.078(2) 0.055(2) 0.0077(17) -0.0027(15) 0.0002(17)
C12 0.0429(16) 0.0494(16) 0.0584(18) -0.0014(14) 0.0036(13) 0.0029(13)
C5 0.0476(17) 0.077(2) 0.060(2) -0.0145(18) -0.0051(15) 0.0137(16)
C10 0.0358(14) 0.0467(15) 0.0568(18) -0.0021(13) 0.0023(13) 0.0055(12)
C4 0.0462(17) 0.100(3) 0.0512(18) 0.0088(18) 0.0027(15) 0.0117(18)
C7 0.070(2) 0.106(3) 0.0471(19) 0.007(2) 0.0019(17) 0.005(2)
C15 0.0359(15) 0.085(2) 0.101(3) -0.005(2) -0.0159(16) 0.0044(17)
C1 0.063(2) 0.101(3) 0.057(2) -0.0072(19) 0.0051(18) -0.032(2)
C6 0.061(2) 0.113(3) 0.050(2) -0.017(2) 0.0008(16) 0.015(2)
C3 0.0480(19) 0.154(4) 0.051(2) 0.020(3) -0.0085(16) -0.004(3)
C1' 0.080(2) 0.097(3) 0.0501(18) 0.0003(19) 0.0031(17) -0.011(2)
C2 0.064(2) 0.153(4) 0.053(2) 0.001(3) -0.0126(19) -0.033(3)
C3' 0.151(6) 0.227(6) 0.066(3) -0.025(4) 0.006(3) -0.046(5)
C2' 0.094(4) 0.242(7) 0.101(3) 0.015(4) 0.040(3) 0.006(4)
C4' 0.118(5) 0.335(11) 0.108(4) -0.051(6) -0.009(4) -0.072(7)
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'
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
C14 O4 C15 116.8(3) . . ?
C16 O2 C1' 117.8(3) . . ?
O4 C14 C13 111.1(3) . . ?
O3 C14 O4 123.2(3) . . ?
O3 C14 C13 125.7(3) . . ?
C5A C8A C5 120.5(3) . . ?
C5A C8A C10 113.3(2) . . ?
C5 C8A C10 126.2(3) . . ?
C16 C11 C13 107.7(2) . . ?
C16 C11 C12 115.0(2) . . ?
C16 C11 C10 106.0(2) . . ?
C13 C11 C12 112.4(2) . . ?
C13 C11 C10 107.7(2) . . ?
C12 C11 C10 107.7(2) . . ?
O2 C16 C11 114.9(2) . . ?
O1 C16 O2 123.5(3) . . ?
O1 C16 C11 121.6(3) . . ?
C8A C5A C9 112.5(2) . . ?
C8 C5A C8A 120.1(3) . . ?
C8 C5A C9 127.4(3) . . ?
C14 C13 C11 114.4(2) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C11 C13 H13A 108.7 . . ?
C11 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C4A C1A C10 113.3(3) . . ?
C4A C1A C4 120.6(3) . . ?
C4 C1A C10 126.1(3) . . ?
C5A C9 H9 111.5 . . ?
C5A C9 C4A 107.2(2) . . ?
C5A C9 C12 107.7(2) . . ?
C4A C9 H9 111.5 . . ?
C4A C9 C12 107.2(2) . . ?
C12 C9 H9 111.5 . . ?
C1A C4A C9 112.5(3) . . ?
C1 C4A C1A 120.0(3) . . ?
C1 C4A C9 127.4(3) . . ?
C5A C8 H8 120.5 . . ?
C5A C8 C7 119.0(3) . . ?
C7 C8 H8 120.5 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C9 C12 C11 110.3(2) . . ?
C9 C12 H12A 109.6 . . ?
C9 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C8A C5 H5 120.9 . . ?
C6 C5 C8A 118.1(3) . . ?
C6 C5 H5 120.9 . . ?
C8A C10 C11 107.1(2) . . ?
C8A C10 H10 111.7 . . ?
C11 C10 H10 111.7 . . ?
C1A C10 C8A 106.9(2) . . ?
C1A C10 C11 107.6(2) . . ?
C1A C10 H10 111.7 . . ?
C1A C4 H4 121.0 . . ?
C3 C4 C1A 118.1(4) . . ?
C3 C4 H4 121.0 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4A C1 H1 120.4 . . ?
C2 C1 C4A 119.1(4) . . ?
C2 C1 H1 120.4 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.4 . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
O2 C1' H1' 109.8 . . ?
O2 C1' C3' 105.8(3) . . ?
O2 C1' C2' 108.5(3) . . ?
C3' C1' H1' 109.8 . . ?
C3' C1' C2' 113.0(4) . . ?
C2' C1' H1' 109.8 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C1' C3' H3'A 108.2 . . ?
C1' C3' H3'B 108.2 . . ?
H3'A C3' H3'B 107.3 . . ?
C4' C3' C1' 116.5(6) . . ?
C4' C3' H3'A 108.2 . . ?
C4' C3' H3'B 108.2 . . ?
C1' C2' H2'A 109.5 . . ?
C1' C2' H2'B 109.5 . . ?
C1' C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C3' C4' H4'A 109.5 . . ?
C3' C4' H4'B 109.5 . . ?
C3' C4' H4'C 109.5 . . ?
H4'A C4' H4'B 109.5 . . ?
H4'A C4' H4'C 109.5 . . ?
H4'B C4' H4'C 109.5 . . ?
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
O4 C14 1.333(3) . ?
O4 C15 1.456(4) . ?
O2 C16 1.331(3) . ?
O2 C1' 1.476(4) . ?
O1 C16 1.204(3) . ?
O3 C14 1.188(3) . ?
C14 C13 1.504(4) . ?
C8A C5A 1.391(4) . ?
C8A C5 1.398(4) . ?
C8A C10 1.516(4) . ?
C11 C16 1.519(4) . ?
C11 C13 1.535(4) . ?
C11 C12 1.550(4) . ?
C11 C10 1.577(4) . ?
C5A C9 1.503(4) . ?
C5A C8 1.381(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C1A C4A 1.394(4) . ?
C1A C10 1.499(4) . ?
C1A C4 1.396(4) . ?
C9 H9 0.9800 . ?
C9 C4A 1.513(4) . ?
C9 C12 1.549(4) . ?
C4A C1 1.389(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.388(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.384(5) . ?
C10 H10 0.9800 . ?
C4 H4 0.9300 . ?
C4 C3 1.393(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.361(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.387(5) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.366(6) . ?
C1' H1' 0.9800 . ?
C1' C3' 1.487(7) . ?
C1' C2' 1.503(6) . ?
C2 H2 0.9300 . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3' C4' 1.413(9) . ?
C2' H2'A 0.9600 . ?
C2' H2'B 0.9600 . ?
C2' H2'C 0.9600 . ?
C4' H4'A 0.9600 . ?
C4' H4'B 0.9600 . ?
C4' H4'C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C14 C13 C11 163.9(2) . . . . ?
O2 C1' C3' C4' -63.3(8) . . . . ?
O3 C14 C13 C11 -17.9(5) . . . . ?
C8A C5A C9 C4A 55.3(3) . . . . ?
C8A C5A C9 C12 -59.7(3) . . . . ?
C8A C5A C8 C7 -0.1(5) . . . . ?
C8A C5 C6 C7 -1.4(5) . . . . ?
C16 O2 C1' C3' 153.8(4) . . . . ?
C16 O2 C1' C2' -84.8(5) . . . . ?
C16 C11 C13 C14 60.7(3) . . . . ?
C16 C11 C12 C9 118.4(3) . . . . ?
C16 C11 C10 C8A 179.0(2) . . . . ?
C16 C11 C10 C1A -66.4(3) . . . . ?
C5A C8A C5 C6 1.5(4) . . . . ?
C5A C8A C10 C11 60.0(3) . . . . ?
C5A C8A C10 C1A -55.0(3) . . . . ?
C5A C9 C4A C1A -55.8(3) . . . . ?
C5A C9 C4A C1 122.5(3) . . . . ?
C5A C9 C12 C11 57.4(3) . . . . ?
C5A C8 C7 C6 0.2(5) . . . . ?
C13 C11 C16 O2 -131.8(2) . . . . ?
C13 C11 C16 O1 50.6(4) . . . . ?
C13 C11 C12 C9 -117.9(3) . . . . ?
C13 C11 C10 C8A 64.0(3) . . . . ?
C13 C11 C10 C1A 178.6(3) . . . . ?
C1A C4A C1 C2 1.4(5) . . . . ?
C1A C4 C3 C2 1.1(5) . . . . ?
C9 C5A C8 C7 179.4(3) . . . . ?
C9 C4A C1 C2 -176.9(3) . . . . ?
C4A C1A C10 C8A 54.6(3) . . . . ?
C4A C1A C10 C11 -60.2(3) . . . . ?
C4A C1A C4 C3 -1.7(4) . . . . ?
C4A C9 C12 C11 -57.6(3) . . . . ?
C4A C1 C2 C3 -2.0(6) . . . . ?
C8 C5A C9 C4A -124.2(3) . . . . ?
C8 C5A C9 C12 120.8(3) . . . . ?
C8 C7 C6 C5 0.6(6) . . . . ?
C12 C11 C16 O2 -5.6(3) . . . . ?
C12 C11 C16 O1 176.8(3) . . . . ?
C12 C11 C13 C14 -67.0(3) . . . . ?
C12 C11 C10 C8A -57.4(3) . . . . ?
C12 C11 C10 C1A 57.2(3) . . . . ?
C12 C9 C4A C1A 59.5(3) . . . . ?
C12 C9 C4A C1 -122.1(3) . . . . ?
C5 C8A C5A C9 179.6(2) . . . . ?
C5 C8A C5A C8 -0.8(4) . . . . ?
C5 C8A C10 C11 -119.7(3) . . . . ?
C5 C8A C10 C1A 125.3(3) . . . . ?
C10 C8A C5A C9 -0.1(3) . . . . ?
C10 C8A C5A C8 179.5(2) . . . . ?
C10 C8A C5 C6 -178.8(3) . . . . ?
C10 C11 C16 O2 113.2(3) . . . . ?
C10 C11 C16 O1 -64.4(3) . . . . ?
C10 C11 C13 C14 174.6(3) . . . . ?
C10 C11 C12 C9 0.5(3) . . . . ?
C10 C1A C4A C9 0.3(3) . . . . ?
C10 C1A C4A C1 -178.2(3) . . . . ?
C10 C1A C4 C3 176.8(3) . . . . ?
C4 C1A C4A C9 179.0(2) . . . . ?
C4 C1A C4A C1 0.5(4) . . . . ?
C4 C1A C10 C8A -124.0(3) . . . . ?
C4 C1A C10 C11 121.2(3) . . . . ?
C4 C3 C2 C1 0.8(6) . . . . ?
C15 O4 C14 O3 -2.2(5) . . . . ?
C15 O4 C14 C13 176.1(3) . . . . ?
C1' O2 C16 O1 -4.0(4) . . . . ?
C1' O2 C16 C11 178.5(2) . . . . ?
C2' C1' C3' C4' 178.2(7) . . . . ?