# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_p11136
#TrackingRef '19340_web_deposit_cif_file_0_ChrisFrampton_1365589603.phx-11-136.cif'
#==============================================================================
_iucr_refine_instructions_details
;
TITL p11136 in P2(1)2(1)2(1)
CELL 1.54178 10.0279 10.4702 13.2012 90.000 90.000 90.000
ZERR 4.00 0.0001 0.0001 0.0001 0.000 0.000 0.000
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 72 80 8
SHEL 5.00 0.80
SIZE 0.50 0.50 0.50
TEMP -173
L.S. 12
BOND $H
CONF
ACTA
EQIV$1 -1.00+X, 0.00+Y, 0.00+Z
HTAB O2 O1_$1
RTAB DIST C17 C18
WPDB -1
MPLA 5 O1 C10 C5 C4 C3 C2
MPLA 6 C5 C6 C7 C8 C9 C10 O1 C4
MPLA 6 C11 C12 C13 C14 C15 C16 C4 O2
FMAP 2
PLAN -9
WGHT 0.043000 0.280000
EXTI 0.006167
FVAR 0.99303
O1 3 0.886920 0.048045 0.847735 11.00000 0.01571 0.01658 =
0.01623 0.00278 -0.00146 -0.00380
O2 3 0.125939 0.131454 0.962516 11.00000 0.01538 0.02939 =
0.02868 -0.00165 0.00506 0.00127
H2A 2 0.052886 0.111558 0.923535 11.00000 0.04841
C2 1 0.843967 0.102599 0.750790 11.00000 0.01577 0.01627 =
0.01438 0.00333 0.00065 0.00043
C3 1 0.691913 0.113325 0.752350 11.00000 0.01575 0.01505 =
0.01607 0.00201 0.00161 0.00124
AFIX 23
H3A 2 0.662284 0.149582 0.686848 11.00000 -1.20000
H3B 2 0.666325 0.174538 0.806101 11.00000 -1.20000
AFIX 0
C4 1 0.615809 -0.013331 0.770511 11.00000 0.01428 0.01458 =
0.01457 -0.00010 -0.00056 0.00051
C5 1 0.697501 -0.098261 0.841232 11.00000 0.01464 0.01442 =
0.01444 -0.00077 0.00071 0.00141
C6 1 0.648123 -0.217074 0.871990 11.00000 0.01576 0.01603 =
0.02262 -0.00006 0.00118 -0.00069
AFIX 43
H6A 2 0.563181 -0.243840 0.848225 11.00000 -1.20000
AFIX 0
C7 1 0.718976 -0.296842 0.935884 11.00000 0.02059 0.01521 =
0.02313 0.00339 0.00459 0.00088
AFIX 43
H7A 2 0.683397 -0.377539 0.954643 11.00000 -1.20000
AFIX 0
C8 1 0.842562 -0.258203 0.972479 11.00000 0.02112 0.01914 =
0.01572 0.00210 0.00204 0.00660
AFIX 43
H8A 2 0.890923 -0.311392 1.017752 11.00000 -1.20000
AFIX 0
C9 1 0.894603 -0.141996 0.942606 11.00000 0.01484 0.02026 =
0.01422 -0.00190 -0.00012 0.00195
AFIX 43
H9A 2 0.978889 -0.115177 0.967646 11.00000 -1.20000
AFIX 0
C10 1 0.824215 -0.063922 0.875985 11.00000 0.01489 0.01399 =
0.01368 -0.00058 0.00319 0.00062
C11 1 0.481485 0.019374 0.821014 11.00000 0.01382 0.01232 =
0.01667 0.00341 -0.00084 0.00036
C12 1 0.479741 0.080367 0.915749 11.00000 0.01535 0.01853 =
0.01585 0.00223 -0.00241 -0.00160
AFIX 43
H12A 2 0.561830 0.097133 0.949120 11.00000 -1.20000
AFIX 0
C13 1 0.361881 0.116681 0.961781 11.00000 0.02087 0.02057 =
0.01595 0.00154 0.00101 -0.00013
AFIX 43
H13A 2 0.363796 0.157846 1.025895 11.00000 -1.20000
AFIX 0
C14 1 0.240542 0.093060 0.914406 11.00000 0.01557 0.01613 =
0.02337 0.00495 0.00341 0.00026
C15 1 0.239338 0.031671 0.821516 11.00000 0.01456 0.01809 =
0.02646 -0.00030 -0.00393 -0.00094
AFIX 43
H15A 2 0.156919 0.014158 0.788864 11.00000 -1.20000
AFIX 0
C16 1 0.358758 -0.004465 0.775842 11.00000 0.01766 0.01663 =
0.02046 -0.00104 -0.00289 -0.00033
AFIX 43
H16A 2 0.356256 -0.046532 0.712108 11.00000 -1.20000
AFIX 0
C17 1 0.592793 -0.084334 0.669855 11.00000 0.01873 0.02264 =
0.01674 -0.00315 -0.00140 -0.00027
AFIX 137
H17A 2 0.541187 -0.162195 0.682535 11.00000 -1.50000
H17B 2 0.678998 -0.107004 0.639861 11.00000 -1.50000
H17C 2 0.543546 -0.028988 0.623115 11.00000 -1.50000
AFIX 0
C18 1 0.900249 0.022754 0.663920 11.00000 0.01850 0.02035 =
0.01835 -0.00038 0.00328 0.00189
AFIX 137
H18A 2 0.878012 -0.067360 0.674754 11.00000 -1.50000
H18B 2 0.997369 0.032716 0.661514 11.00000 -1.50000
H18C 2 0.861480 0.051672 0.599752 11.00000 -1.50000
AFIX 0
C19 1 0.905683 0.234699 0.748604 11.00000 0.02055 0.01782 =
0.02197 0.00263 0.00403 -0.00197
AFIX 137
H19A 2 0.871941 0.284851 0.805804 11.00000 -1.50000
H19B 2 0.882129 0.277306 0.684973 11.00000 -1.50000
H19C 2 1.002885 0.227362 0.753621 11.00000 -1.50000
HKLF 4
REM p11136 in P2(1)2(1)2(1)
REM R1 = 0.0254 for 2820 Fo > 4sig(Fo) and 0.0255 for all 2825 data
REM 189 parameters refined using 0 restraints
END
WGHT 0.0350 0.2929
REM Highest difference peak 0.215, deepest hole -0.138, 1-sigma level 0.030
Q1 1 0.7693 0.1048 0.7458 11.00000 0.05 0.21
Q2 1 0.5488 0.0027 0.7969 11.00000 0.05 0.20
Q3 1 0.3018 0.1015 0.9410 11.00000 0.05 0.18
Q4 1 0.7659 -0.1025 0.8449 11.00000 0.05 0.17
Q5 1 0.6584 0.0487 0.7616 11.00000 0.05 0.17
Q6 1 0.7529 -0.0846 0.8627 11.00000 0.05 0.16
Q7 1 0.6552 -0.0553 0.8078 11.00000 0.05 0.16
Q8 1 0.2485 0.0873 0.8578 11.00000 0.05 0.16
Q9 1 0.6807 -0.1654 0.8438 11.00000 0.05 0.15
;
#==============================================================================
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
R-4-p-hydroxyphenyl-2,2,4-trimethylchroman
;
_chemical_name_common
;
R-Dianin's Compound
;
_chemical_melting_point ?
_chemical_compound_source ?
_chemical_absolute_configuration ad
_chemical_formula_iupac ?
_chemical_formula_moiety 'C18 H20 O2'
_chemical_formula_sum 'C18 H20 O2'
_chemical_formula_weight 268.34
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_space_group_id
1
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_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'
_cell_length_a 10.0279(1)
_cell_length_b 10.4702(1)
_cell_length_c 13.2012(1)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1386.05(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 19772
_cell_measurement_theta_min 3.3451
_cell_measurement_theta_max 75.4925
_exptl_crystal_description Block
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.50
_exptl_crystal_size_min 0.50
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.286
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 576
_exptl_absorpt_coefficient_mu 0.646
_exptl_absorpt_correction_T_min 0.64010
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(1)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5598
_diffrn_measurement_method '\w scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 24324
_diffrn_reflns_av_R_equivalents 0.0245
_diffrn_reflns_av_sigmaI/netI 0.0092
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 9.09
_diffrn_reflns_theta_max 74.47
_reflns_number_total 2825
_reflns_number_gt 2820
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution 'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.2800P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0062(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.03(15)
_refine_ls_number_reflns 2825
_refine_ls_number_parameters 189
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0255
_refine_ls_R_factor_gt 0.0254
_refine_ls_wR_factor_ref 0.0684
_refine_ls_wR_factor_gt 0.0684
_refine_ls_goodness_of_fit_ref 1.007
_refine_ls_restrained_S_all 1.007
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.88692(7) 0.04805(7) 0.84773(5) 0.01617(16) Uani 1 1 d . . .
O2 O 0.12594(8) 0.13145(8) 0.96252(6) 0.02448(18) Uani 1 1 d . . .
H2A H 0.0529(19) 0.1116(18) 0.9235(13) 0.048(5) Uiso 1 1 d . . .
C2 C 0.84397(10) 0.10260(9) 0.75079(7) 0.0155(2) Uani 1 1 d . . .
C3 C 0.69191(9) 0.11332(10) 0.75235(7) 0.0156(2) Uani 1 1 d . . .
H3A H 0.6623 0.1496 0.6868 0.019 Uiso 1 1 calc R . .
H3B H 0.6663 0.1745 0.8061 0.019 Uiso 1 1 calc R . .
C4 C 0.61581(10) -0.01333(9) 0.77051(7) 0.0145(2) Uani 1 1 d . . .
C5 C 0.69750(10) -0.09826(9) 0.84123(7) 0.0145(2) Uani 1 1 d . . .
C6 C 0.64812(11) -0.21707(9) 0.87199(8) 0.0181(2) Uani 1 1 d . . .
H6A H 0.5632 -0.2438 0.8482 0.022 Uiso 1 1 calc R . .
C7 C 0.71898(11) -0.29684(10) 0.93588(8) 0.0196(2) Uani 1 1 d . . .
H7A H 0.6834 -0.3775 0.9546 0.024 Uiso 1 1 calc R . .
C8 C 0.84256(11) -0.25820(10) 0.97248(8) 0.0187(2) Uani 1 1 d . . .
H8A H 0.8909 -0.3114 1.0178 0.022 Uiso 1 1 calc R . .
C9 C 0.89460(10) -0.14200(10) 0.94261(7) 0.0164(2) Uani 1 1 d . . .
H9A H 0.9789 -0.1152 0.9676 0.020 Uiso 1 1 calc R . .
C10 C 0.82422(10) -0.06392(9) 0.87598(7) 0.0142(2) Uani 1 1 d . . .
C11 C 0.48149(10) 0.01937(9) 0.82101(7) 0.0143(2) Uani 1 1 d . . .
C12 C 0.47974(10) 0.08037(10) 0.91575(7) 0.0166(2) Uani 1 1 d . . .
H12A H 0.5618 0.0971 0.9491 0.020 Uiso 1 1 calc R . .
C13 C 0.36188(11) 0.11668(10) 0.96178(7) 0.0191(2) Uani 1 1 d . . .
H13A H 0.3638 0.1578 1.0259 0.023 Uiso 1 1 calc R . .
C14 C 0.24054(10) 0.09306(10) 0.91441(8) 0.0184(2) Uani 1 1 d . . .
C15 C 0.23934(11) 0.03167(10) 0.82152(9) 0.0197(2) Uani 1 1 d . . .
H15A H 0.1569 0.0142 0.7889 0.024 Uiso 1 1 calc R . .
C16 C 0.35876(11) -0.00447(10) 0.77584(8) 0.0182(2) Uani 1 1 d . . .
H16A H 0.3563 -0.0465 0.7121 0.022 Uiso 1 1 calc R . .
C17 C 0.59279(10) -0.08433(10) 0.66986(8) 0.0194(2) Uani 1 1 d . . .
H17A H 0.5412 -0.1622 0.6825 0.029 Uiso 1 1 calc R . .
H17B H 0.6790 -0.1070 0.6399 0.029 Uiso 1 1 calc R . .
H17C H 0.5435 -0.0290 0.6231 0.029 Uiso 1 1 calc R . .
C18 C 0.90025(10) 0.02275(10) 0.66392(8) 0.0191(2) Uani 1 1 d . . .
H18A H 0.8780 -0.0674 0.6748 0.029 Uiso 1 1 calc R . .
H18B H 0.9974 0.0327 0.6615 0.029 Uiso 1 1 calc R . .
H18C H 0.8615 0.0517 0.5998 0.029 Uiso 1 1 calc R . .
C19 C 0.90568(11) 0.23470(10) 0.74860(8) 0.0201(2) Uani 1 1 d . . .
H19A H 0.8719 0.2849 0.8058 0.030 Uiso 1 1 calc R . .
H19B H 0.8821 0.2773 0.6850 0.030 Uiso 1 1 calc R . .
H19C H 1.0029 0.2274 0.7536 0.030 Uiso 1 1 calc R . .
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
O1 0.0157(3) 0.0166(3) 0.0162(3) 0.0028(3) -0.0015(3) -0.0038(3)
O2 0.0154(4) 0.0294(4) 0.0287(4) -0.0017(3) 0.0051(3) 0.0013(3)
C2 0.0158(4) 0.0163(5) 0.0144(4) 0.0033(4) 0.0006(4) 0.0004(4)
C3 0.0157(5) 0.0151(5) 0.0161(4) 0.0020(4) 0.0016(4) 0.0012(4)
C4 0.0143(5) 0.0146(4) 0.0146(4) -0.0001(4) -0.0006(4) 0.0005(4)
C5 0.0146(4) 0.0144(4) 0.0144(4) -0.0008(4) 0.0007(4) 0.0014(4)
C6 0.0158(5) 0.0160(5) 0.0226(5) -0.0001(4) 0.0012(4) -0.0007(4)
C7 0.0206(5) 0.0152(4) 0.0231(5) 0.0034(4) 0.0046(4) 0.0009(4)
C8 0.0211(5) 0.0191(5) 0.0157(5) 0.0021(4) 0.0020(4) 0.0066(4)
C9 0.0148(4) 0.0203(5) 0.0142(4) -0.0019(4) -0.0001(4) 0.0020(4)
C10 0.0149(5) 0.0140(4) 0.0137(4) -0.0006(3) 0.0032(4) 0.0006(4)
C11 0.0138(4) 0.0123(4) 0.0167(5) 0.0034(4) -0.0008(4) 0.0004(4)
C12 0.0154(5) 0.0185(5) 0.0159(4) 0.0022(4) -0.0024(4) -0.0016(4)
C13 0.0209(5) 0.0206(5) 0.0159(4) 0.0015(4) 0.0010(4) -0.0001(4)
C14 0.0156(5) 0.0161(5) 0.0234(5) 0.0050(4) 0.0034(4) 0.0003(4)
C15 0.0146(5) 0.0181(5) 0.0265(5) -0.0003(4) -0.0039(4) -0.0009(4)
C16 0.0177(5) 0.0166(5) 0.0205(5) -0.0010(4) -0.0029(4) -0.0003(4)
C17 0.0187(5) 0.0226(5) 0.0167(5) -0.0032(4) -0.0014(4) -0.0003(4)
C18 0.0185(5) 0.0203(5) 0.0184(5) -0.0004(4) 0.0033(4) 0.0019(4)
C19 0.0206(5) 0.0178(5) 0.0220(5) 0.0026(4) 0.0040(4) -0.0020(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C10 1.3816(12) . ?
O1 C2 1.4662(11) . ?
O2 C14 1.3732(13) . ?
O2 H2A 0.919(19) . ?
C2 C19 1.5155(14) . ?
C2 C18 1.5273(14) . ?
C2 C3 1.5290(13) . ?
C3 C4 1.5487(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5276(13) . ?
C4 C17 1.5400(13) . ?
C4 C11 1.5415(13) . ?
C5 C10 1.3980(14) . ?
C5 C6 1.3991(14) . ?
C6 C7 1.3834(15) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3903(15) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3814(15) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3928(14) . ?
C9 H9A 0.9500 . ?
C11 C16 1.3902(14) . ?
C11 C12 1.4043(14) . ?
C12 C13 1.3823(15) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3903(15) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3846(15) . ?
C15 C16 1.3931(15) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
C10 O1 C2 115.62(7) . . ?
C14 O2 H2A 110.0(11) . . ?
O1 C2 C19 104.61(8) . . ?
O1 C2 C18 109.49(8) . . ?
C19 C2 C18 109.53(8) . . ?
O1 C2 C3 108.05(8) . . ?
C19 C2 C3 109.90(8) . . ?
C18 C2 C3 114.76(8) . . ?
C2 C3 C4 115.51(8) . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C17 109.07(8) . . ?
C5 C4 C11 109.49(8) . . ?
C17 C4 C11 110.45(8) . . ?
C5 C4 C3 109.20(8) . . ?
C17 C4 C3 110.71(8) . . ?
C11 C4 C3 107.90(8) . . ?
C10 C5 C6 117.07(9) . . ?
C10 C5 C4 122.57(9) . . ?
C6 C5 C4 120.34(9) . . ?
C7 C6 C5 122.14(10) . . ?
C7 C6 H6A 118.9 . . ?
C5 C6 H6A 118.9 . . ?
C6 C7 C8 119.60(10) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C9 C8 C7 119.59(10) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.38(10) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
O1 C10 C9 115.96(9) . . ?
O1 C10 C5 122.91(9) . . ?
C9 C10 C5 121.12(9) . . ?
C16 C11 C12 116.91(9) . . ?
C16 C11 C4 123.24(9) . . ?
C12 C11 C4 119.81(9) . . ?
C13 C12 C11 121.82(9) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C12 C13 C14 120.11(9) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
O2 C14 C15 122.56(10) . . ?
O2 C14 C13 118.19(9) . . ?
C15 C14 C13 119.25(9) . . ?
C14 C15 C16 120.13(10) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C11 C16 C15 121.77(9) . . ?
C11 C16 H16A 119.1 . . ?
C15 C16 H16A 119.1 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
C10 O1 C2 C19 168.95(8) . . . . ?
C10 O1 C2 C18 -73.75(10) . . . . ?
C10 O1 C2 C3 51.88(10) . . . . ?
O1 C2 C3 C4 -57.80(11) . . . . ?
C19 C2 C3 C4 -171.38(8) . . . . ?
C18 C2 C3 C4 64.66(11) . . . . ?
C2 C3 C4 C5 33.49(11) . . . . ?
C2 C3 C4 C17 -86.61(10) . . . . ?
C2 C3 C4 C11 152.41(8) . . . . ?
C17 C4 C5 C10 117.49(10) . . . . ?
C11 C4 C5 C10 -121.54(10) . . . . ?
C3 C4 C5 C10 -3.61(12) . . . . ?
C17 C4 C5 C6 -60.88(12) . . . . ?
C11 C4 C5 C6 60.08(11) . . . . ?
C3 C4 C5 C6 178.01(8) . . . . ?
C10 C5 C6 C7 1.50(15) . . . . ?
C4 C5 C6 C7 179.96(9) . . . . ?
C5 C6 C7 C8 0.94(16) . . . . ?
C6 C7 C8 C9 -1.60(16) . . . . ?
C7 C8 C9 C10 -0.21(15) . . . . ?
C2 O1 C10 C9 155.79(8) . . . . ?
C2 O1 C10 C5 -24.60(12) . . . . ?
C8 C9 C10 O1 -177.63(8) . . . . ?
C8 C9 C10 C5 2.75(14) . . . . ?
C6 C5 C10 O1 177.09(9) . . . . ?
C4 C5 C10 O1 -1.34(14) . . . . ?
C6 C5 C10 C9 -3.32(13) . . . . ?
C4 C5 C10 C9 178.25(9) . . . . ?
C5 C4 C11 C16 -124.76(10) . . . . ?
C17 C4 C11 C16 -4.64(13) . . . . ?
C3 C4 C11 C16 116.50(10) . . . . ?
C5 C4 C11 C12 57.57(11) . . . . ?
C17 C4 C11 C12 177.69(9) . . . . ?
C3 C4 C11 C12 -61.17(11) . . . . ?
C16 C11 C12 C13 -0.78(15) . . . . ?
C4 C11 C12 C13 177.04(9) . . . . ?
C11 C12 C13 C14 0.04(15) . . . . ?
C12 C13 C14 O2 -179.59(10) . . . . ?
C12 C13 C14 C15 0.73(15) . . . . ?
O2 C14 C15 C16 179.59(9) . . . . ?
C13 C14 C15 C16 -0.74(15) . . . . ?
C12 C11 C16 C15 0.77(15) . . . . ?
C4 C11 C16 C15 -176.97(9) . . . . ?
C14 C15 C16 C11 -0.02(16) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O1 0.919(19) 2.05(2) 2.9671(11) 173.0(16) 1_455
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 74.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.215
_refine_diff_density_min -0.138
_refine_diff_density_rms 0.030
_database_code_depnum_ccdc_archive 'CCDC 933470'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_p11135a
#TrackingRef '19341_web_deposit_cif_file_1_ChrisFrampton_1365589603.phx-11-135.cif'
#==============================================================================
_iucr_refine_instructions_details
;
TITL p11135a in P2(1)2(1)2(1)
CELL 1.54178 10.5486 10.5395 13.1045 90.000 90.000 90.000
ZERR 4.00 0.0001 0.0001 0.0002 0.000 0.000 0.000
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 S
UNIT 72 80 4 4
SHEL 5.00 0.80
SIZE 0.50 0.50 0.50
TEMP -173
L.S. 12
BOND $H
CONF
ACTA
EQIV$1 -1.00+X, 0.00+Y, 0.00+Z
HTAB O1 S1_$1
RTAB DIST C17 C18
WPDB -1
MPLA 5 S1 C10 C5 C4 C3 C2
MPLA 6 C5 C6 C7 C8 C9 C10 S1 C4
MPLA 6 C11 C12 C13 C14 C15 C16 C4 O1
FMAP 2
PLAN -9
WGHT 0.041000 0.550000
EXTI 0.005643
FVAR 0.90358
S1 4 0.393893 0.427120 0.873704 11.00000 0.01710 0.01740 =
0.01976 -0.00353 -0.00443 0.00453
O1 3 -0.325911 0.359443 0.983325 11.00000 0.01458 0.02779 =
0.03552 0.00415 0.00467 -0.00195
H1A 2 -0.390463 0.378408 0.952381 11.00000 0.03763
C2 1 0.338273 0.383250 0.746387 11.00000 0.01533 0.01706 =
0.01611 -0.00232 0.00108 0.00094
C3 1 0.192724 0.386572 0.750809 11.00000 0.01480 0.01359 =
0.01591 -0.00242 -0.00003 -0.00018
AFIX 23
H3A 2 0.165436 0.324275 0.802909 11.00000 -1.20000
H3B 2 0.160595 0.356008 0.684219 11.00000 -1.20000
AFIX 0
C4 1 0.124889 0.514335 0.774697 11.00000 0.01314 0.01300 =
0.01502 0.00028 -0.00076 -0.00096
C5 1 0.199877 0.602860 0.846076 11.00000 0.01423 0.01357 =
0.01447 0.00115 0.00169 -0.00217
C6 1 0.148296 0.722158 0.868976 11.00000 0.01645 0.01529 =
0.02178 0.00136 -0.00082 0.00085
AFIX 43
H6A 2 0.068441 0.744239 0.840549 11.00000 -1.20000
AFIX 0
C7 1 0.208897 0.808859 0.931193 11.00000 0.02221 0.01533 =
0.02280 -0.00123 0.00333 -0.00001
AFIX 43
H7A 2 0.171016 0.888982 0.944348 11.00000 -1.20000
AFIX 0
C8 1 0.325715 0.778667 0.974666 11.00000 0.02034 0.01791 =
0.01702 -0.00215 0.00198 -0.00632
AFIX 43
H8A 2 0.367939 0.837331 1.017957 11.00000 -1.20000
AFIX 0
C9 1 0.378767 0.661959 0.953583 11.00000 0.01474 0.01935 =
0.01543 0.00087 0.00093 -0.00236
AFIX 43
H9A 2 0.458446 0.640505 0.982634 11.00000 -1.20000
AFIX 0
C10 1 0.317419 0.574686 0.890249 11.00000 0.01462 0.01411 =
0.01392 -0.00026 0.00150 -0.00155
C11 1 -0.000297 0.479366 0.827852 11.00000 0.01527 0.01103 =
0.01698 -0.00235 0.00035 0.00000
C12 1 0.005405 0.419753 0.923798 11.00000 0.01514 0.01459 =
0.01748 -0.00295 -0.00235 0.00014
AFIX 43
H12A 2 0.085708 0.405590 0.954577 11.00000 -1.20000
AFIX 0
C13 1 -0.103028 0.381262 0.974411 11.00000 0.01785 0.01510 =
0.01985 -0.00118 0.00101 0.00021
AFIX 43
H13A 2 -0.096897 0.342379 1.039626 11.00000 -1.20000
AFIX 0
C14 1 -0.221287 0.399700 0.929437 11.00000 0.01449 0.01417 =
0.02517 -0.00303 0.00345 -0.00188
C15 1 -0.229441 0.458119 0.835355 11.00000 0.01296 0.01870 =
0.02674 -0.00219 -0.00396 0.00149
AFIX 43
H15A 2 -0.309900 0.471052 0.804492 11.00000 -1.20000
AFIX 0
C16 1 -0.119476 0.498199 0.785553 11.00000 0.01671 0.01512 =
0.01899 -0.00101 -0.00346 0.00146
AFIX 43
H16A 2 -0.126379 0.539285 0.721268 11.00000 -1.20000
AFIX 0
C17 1 0.100122 0.585231 0.673469 11.00000 0.02022 0.01944 =
0.01694 0.00299 -0.00064 0.00134
AFIX 137
H17A 2 0.052008 0.662904 0.687256 11.00000 -1.50000
H17B 2 0.051432 0.530559 0.627392 11.00000 -1.50000
H17C 2 0.181212 0.607205 0.641540 11.00000 -1.50000
AFIX 0
C18 1 0.396784 0.468772 0.665082 11.00000 0.02161 0.02291 =
0.02164 0.00144 0.00652 -0.00043
AFIX 137
H18A 2 0.359118 0.449268 0.598545 11.00000 -1.50000
H18B 2 0.488473 0.454213 0.662229 11.00000 -1.50000
H18C 2 0.380338 0.557761 0.682258 11.00000 -1.50000
AFIX 0
C19 1 0.382340 0.247014 0.730371 11.00000 0.01989 0.01913 =
0.02145 -0.00374 0.00159 0.00132
AFIX 137
H19A 2 0.355452 0.217694 0.662783 11.00000 -1.50000
H19B 2 0.344928 0.192451 0.782907 11.00000 -1.50000
H19C 2 0.474980 0.243276 0.735122 11.00000 -1.50000
HKLF 4
REM p11135a in P2(1)2(1)2(1)
REM R1 = 0.0259 for 2936 Fo > 4sig(Fo) and 0.0269 for all 2957 data
REM 189 parameters refined using 0 restraints
END
WGHT 0.0327 0.5667
REM Highest difference peak 0.220, deepest hole -0.154, 1-sigma level 0.038
Q1 1 0.0634 0.5008 0.7974 11.00000 0.05 0.22
Q2 1 0.3865 0.4235 0.8018 11.00000 0.05 0.21
Q3 1 -0.1578 0.4098 0.9594 11.00000 0.05 0.19
Q4 1 -0.0018 0.4548 0.8744 11.00000 0.05 0.18
Q5 1 0.3615 0.3110 0.7418 11.00000 0.05 0.18
Q6 1 0.1662 0.4562 0.7610 11.00000 0.05 0.18
Q7 1 0.1044 0.5507 0.7338 11.00000 0.05 0.17
Q8 1 -0.1711 0.4424 0.8042 11.00000 0.05 0.17
;
#==============================================================================
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
S-4-p-hydroxyphenyl-2,2,4-trimethylthiachroman
;
_chemical_name_common
;
S-ThiaDianin's Compound
;
_chemical_melting_point ?
_chemical_compound_source ?
_chemical_absolute_configuration ad
_chemical_formula_iupac ?
_chemical_formula_moiety 'C18 H20 O S'
_chemical_formula_sum 'C18 H20 O S'
_chemical_formula_weight 284.40
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_space_group_id
1
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_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'
_cell_length_a 10.5486(1)
_cell_length_b 10.5395(1)
_cell_length_c 13.1045(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1456.92(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 5765
_cell_measurement_theta_min 3.3698
_cell_measurement_theta_max 75.3842
_exptl_crystal_description Block
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.50
_exptl_crystal_size_min 0.50
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.297
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 608
_exptl_absorpt_coefficient_mu 1.896
_exptl_absorpt_correction_T_min 0.69769
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(1)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5598
_diffrn_measurement_method '\w scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7286
_diffrn_reflns_av_R_equivalents 0.0171
_diffrn_reflns_av_sigmaI/netI 0.0184
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_theta_min 9.01
_diffrn_reflns_theta_max 74.47
_reflns_number_total 2957
_reflns_number_gt 2936
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution 'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.5500P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0056(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.015(13)
_refine_ls_number_reflns 2957
_refine_ls_number_parameters 189
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0269
_refine_ls_R_factor_gt 0.0259
_refine_ls_wR_factor_ref 0.0704
_refine_ls_wR_factor_gt 0.0700
_refine_ls_goodness_of_fit_ref 1.006
_refine_ls_restrained_S_all 1.006
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.39389(3) 0.42712(3) 0.87370(3) 0.01809(11) Uani 1 1 d . . .
O1 O -0.32591(11) 0.35944(11) 0.98332(9) 0.0260(3) Uani 1 1 d . . .
H1A H -0.390(2) 0.378(2) 0.9524(17) 0.038(6) Uiso 1 1 d . . .
C2 C 0.33827(13) 0.38325(13) 0.74639(11) 0.0162(3) Uani 1 1 d . . .
C3 C 0.19272(13) 0.38657(13) 0.75081(11) 0.0148(3) Uani 1 1 d . . .
H3A H 0.1654 0.3243 0.8029 0.018 Uiso 1 1 calc R . .
H3B H 0.1606 0.3560 0.6842 0.018 Uiso 1 1 calc R . .
C4 C 0.12489(13) 0.51434(13) 0.77470(10) 0.0137(3) Uani 1 1 d . . .
C5 C 0.19988(13) 0.60286(13) 0.84608(10) 0.0141(3) Uani 1 1 d . . .
C6 C 0.14830(13) 0.72216(14) 0.86898(11) 0.0178(3) Uani 1 1 d . . .
H6A H 0.0684 0.7442 0.8405 0.021 Uiso 1 1 calc R . .
C7 C 0.20890(14) 0.80886(15) 0.93119(12) 0.0201(3) Uani 1 1 d . . .
H7A H 0.1710 0.8890 0.9443 0.024 Uiso 1 1 calc R . .
C8 C 0.32572(14) 0.77867(14) 0.97467(11) 0.0184(3) Uani 1 1 d . . .
H8A H 0.3679 0.8373 1.0180 0.022 Uiso 1 1 calc R . .
C9 C 0.37877(14) 0.66196(13) 0.95358(10) 0.0165(3) Uani 1 1 d . . .
H9A H 0.4584 0.6405 0.9826 0.020 Uiso 1 1 calc R . .
C10 C 0.31742(13) 0.57469(14) 0.89025(10) 0.0142(3) Uani 1 1 d . . .
C11 C -0.00030(14) 0.47937(13) 0.82785(11) 0.0144(3) Uani 1 1 d . . .
C12 C 0.00541(13) 0.41975(14) 0.92380(10) 0.0157(3) Uani 1 1 d . . .
H12A H 0.0857 0.4056 0.9546 0.019 Uiso 1 1 calc R . .
C13 C -0.10303(14) 0.38126(13) 0.97441(11) 0.0176(3) Uani 1 1 d . . .
H13A H -0.0969 0.3424 1.0396 0.021 Uiso 1 1 calc R . .
C14 C -0.22129(14) 0.39970(14) 0.92944(12) 0.0179(3) Uani 1 1 d . . .
C15 C -0.22944(14) 0.45812(14) 0.83536(12) 0.0195(3) Uani 1 1 d . . .
H15A H -0.3099 0.4711 0.8045 0.023 Uiso 1 1 calc R . .
C16 C -0.11948(14) 0.49820(13) 0.78555(10) 0.0169(3) Uani 1 1 d . . .
H16A H -0.1264 0.5393 0.7213 0.020 Uiso 1 1 calc R . .
C17 C 0.10012(15) 0.58523(14) 0.67347(10) 0.0189(3) Uani 1 1 d . . .
H17A H 0.0520 0.6629 0.6873 0.028 Uiso 1 1 calc R . .
H17B H 0.0514 0.5306 0.6274 0.028 Uiso 1 1 calc R . .
H17C H 0.1812 0.6072 0.6415 0.028 Uiso 1 1 calc R . .
C18 C 0.39678(16) 0.46877(14) 0.66508(11) 0.0221(3) Uani 1 1 d . . .
H18A H 0.3591 0.4493 0.5985 0.033 Uiso 1 1 calc R . .
H18B H 0.4885 0.4542 0.6622 0.033 Uiso 1 1 calc R . .
H18C H 0.3803 0.5578 0.6823 0.033 Uiso 1 1 calc R . .
C19 C 0.38234(15) 0.24701(14) 0.73037(11) 0.0202(3) Uani 1 1 d . . .
H19A H 0.3555 0.2177 0.6628 0.030 Uiso 1 1 calc R . .
H19B H 0.3449 0.1925 0.7829 0.030 Uiso 1 1 calc R . .
H19C H 0.4750 0.2433 0.7351 0.030 Uiso 1 1 calc R . .
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
S1 0.01710(17) 0.01740(17) 0.01976(17) -0.00353(13) -0.00443(13) 0.00453(13)
O1 0.0146(5) 0.0278(6) 0.0355(6) 0.0042(5) 0.0047(5) -0.0019(4)
C2 0.0153(6) 0.0171(7) 0.0161(6) -0.0023(5) 0.0011(5) 0.0009(5)
C3 0.0148(6) 0.0136(6) 0.0159(6) -0.0024(5) 0.0000(5) -0.0002(5)
C4 0.0131(6) 0.0130(6) 0.0150(6) 0.0003(5) -0.0008(5) -0.0010(5)
C5 0.0142(6) 0.0136(6) 0.0145(6) 0.0012(5) 0.0017(5) -0.0022(5)
C6 0.0165(7) 0.0153(6) 0.0218(6) 0.0014(6) -0.0008(5) 0.0009(5)
C7 0.0222(7) 0.0153(7) 0.0228(7) -0.0012(6) 0.0033(6) 0.0000(6)
C8 0.0203(7) 0.0179(7) 0.0170(6) -0.0021(5) 0.0020(6) -0.0063(6)
C9 0.0147(6) 0.0193(7) 0.0154(6) 0.0009(5) 0.0009(5) -0.0024(6)
C10 0.0146(6) 0.0141(6) 0.0139(6) -0.0003(5) 0.0015(5) -0.0015(5)
C11 0.0153(7) 0.0110(6) 0.0170(6) -0.0023(5) 0.0003(5) 0.0000(5)
C12 0.0151(6) 0.0146(6) 0.0175(6) -0.0030(6) -0.0023(5) 0.0001(5)
C13 0.0179(6) 0.0151(6) 0.0199(6) -0.0012(5) 0.0010(6) 0.0002(6)
C14 0.0145(6) 0.0142(7) 0.0252(7) -0.0030(6) 0.0034(6) -0.0019(5)
C15 0.0130(6) 0.0187(7) 0.0267(8) -0.0022(6) -0.0040(5) 0.0015(5)
C16 0.0167(7) 0.0151(6) 0.0190(6) -0.0010(5) -0.0035(5) 0.0015(6)
C17 0.0202(7) 0.0194(7) 0.0169(6) 0.0030(5) -0.0006(5) 0.0013(6)
C18 0.0216(7) 0.0229(7) 0.0216(7) 0.0014(6) 0.0065(6) -0.0004(6)
C19 0.0199(7) 0.0191(7) 0.0215(7) -0.0037(5) 0.0016(6) 0.0013(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1 C10 1.7654(15) . ?
S1 C2 1.8280(14) . ?
O1 C14 1.3772(18) . ?
O1 H1A 0.82(2) . ?
C2 C19 1.524(2) . ?
C2 C18 1.5260(19) . ?
C2 C3 1.5368(19) . ?
C3 C4 1.5567(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.5378(19) . ?
C4 C5 1.5399(19) . ?
C4 C17 1.5448(18) . ?
C5 C10 1.4002(19) . ?
C5 C6 1.4025(19) . ?
C6 C7 1.381(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.394(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.379(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3977(19) . ?
C9 H9A 0.9500 . ?
C11 C16 1.388(2) . ?
C11 C12 1.407(2) . ?
C12 C13 1.383(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.393(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.381(2) . ?
C15 C16 1.396(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
C10 S1 C2 100.85(6) . . ?
C14 O1 H1A 109.7(16) . . ?
C19 C2 C18 109.70(12) . . ?
C19 C2 C3 109.36(12) . . ?
C18 C2 C3 114.64(12) . . ?
C19 C2 S1 105.44(10) . . ?
C18 C2 S1 110.98(10) . . ?
C3 C2 S1 106.29(9) . . ?
C2 C3 C4 119.11(11) . . ?
C2 C3 H3A 107.5 . . ?
C4 C3 H3A 107.5 . . ?
C2 C3 H3B 107.5 . . ?
C4 C3 H3B 107.5 . . ?
H3A C3 H3B 107.0 . . ?
C11 C4 C5 108.13(11) . . ?
C11 C4 C17 111.08(12) . . ?
C5 C4 C17 108.39(11) . . ?
C11 C4 C3 106.17(11) . . ?
C5 C4 C3 114.21(11) . . ?
C17 C4 C3 108.87(11) . . ?
C10 C5 C6 116.44(13) . . ?
C10 C5 C4 125.28(12) . . ?
C6 C5 C4 118.29(12) . . ?
C7 C6 C5 122.67(13) . . ?
C7 C6 H6A 118.7 . . ?
C5 C6 H6A 118.7 . . ?
C6 C7 C8 119.94(14) . . ?
C6 C7 H7A 120.0 . . ?
C8 C7 H7A 120.0 . . ?
C9 C8 C7 118.70(14) . . ?
C9 C8 H8A 120.6 . . ?
C7 C8 H8A 120.6 . . ?
C8 C9 C10 121.19(14) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C9 C10 C5 121.06(13) . . ?
C9 C10 S1 116.17(11) . . ?
C5 C10 S1 122.73(11) . . ?
C16 C11 C12 117.35(13) . . ?
C16 C11 C4 124.23(13) . . ?
C12 C11 C4 118.37(12) . . ?
C13 C12 C11 121.62(13) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C14 119.78(13) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
O1 C14 C15 123.05(13) . . ?
O1 C14 C13 117.23(14) . . ?
C15 C14 C13 119.71(13) . . ?
C14 C15 C16 120.03(13) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C11 C16 C15 121.49(13) . . ?
C11 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
C10 S1 C2 C19 -171.53(10) . . . . ?
C10 S1 C2 C18 69.76(11) . . . . ?
C10 S1 C2 C3 -55.50(10) . . . . ?
C19 C2 C3 C4 175.55(12) . . . . ?
C18 C2 C3 C4 -60.80(17) . . . . ?
S1 C2 C3 C4 62.19(14) . . . . ?
C2 C3 C4 C11 -151.01(12) . . . . ?
C2 C3 C4 C5 -31.96(17) . . . . ?
C2 C3 C4 C17 89.32(15) . . . . ?
C11 C4 C5 C10 116.21(14) . . . . ?
C17 C4 C5 C10 -123.29(14) . . . . ?
C3 C4 C5 C10 -1.74(19) . . . . ?
C11 C4 C5 C6 -64.32(15) . . . . ?
C17 C4 C5 C6 56.19(16) . . . . ?
C3 C4 C5 C6 177.74(12) . . . . ?
C10 C5 C6 C7 0.3(2) . . . . ?
C4 C5 C6 C7 -179.22(13) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C5 0.0(2) . . . . ?
C8 C9 C10 S1 -177.86(11) . . . . ?
C6 C5 C10 C9 -0.02(19) . . . . ?
C4 C5 C10 C9 179.46(12) . . . . ?
C6 C5 C10 S1 177.66(10) . . . . ?
C4 C5 C10 S1 -2.85(19) . . . . ?
C2 S1 C10 C9 -151.41(10) . . . . ?
C2 S1 C10 C5 30.80(12) . . . . ?
C5 C4 C11 C16 124.59(14) . . . . ?
C17 C4 C11 C16 5.78(19) . . . . ?
C3 C4 C11 C16 -112.43(15) . . . . ?
C5 C4 C11 C12 -58.08(15) . . . . ?
C17 C4 C11 C12 -176.90(12) . . . . ?
C3 C4 C11 C12 64.89(15) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C4 C11 C12 C13 -177.54(13) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 O1 179.97(13) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
O1 C14 C15 C16 179.09(14) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C12 C11 C16 C15 -0.9(2) . . . . ?
C4 C11 C16 C15 176.48(14) . . . . ?
C14 C15 C16 C11 0.8(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A S1 0.82(2) 2.55(3) 3.3628(12) 173(2) 1_455
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 74.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.220
_refine_diff_density_min -0.154
_refine_diff_density_rms 0.038
_database_code_depnum_ccdc_archive 'CCDC 933471'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_p12001_1n
#TrackingRef '19342_web_deposit_cif_file_2_ChrisFrampton_1365589603.phx-12-001.cif'
#==============================================================================
_iucr_refine_instructions_details
;
TITL p12001_1n in R3
CELL 1.54178 27.2258 27.2258 10.8365 90.000 90.000 120.000
ZERR 9.00 0.0004 0.0004 0.0002 0.000 0.000 0.000
LATT -3
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SFAC C H O S
UNIT 324 360 27 9
SIZE 0.25 0.07 0.05
SHEL 5.00 0.80
TEMP -183
L.S. 12
CONF
ACTA
EQIV$1 1.00-Y, 1.00+x-y, 0.00+Z
HTAB O2A O2B
HTAB O2B O2A_$1
RTAB DIST C17A C18A
RTAB DIST C17B C18B
MPLA 6 C5A C6A C7A C8A C9A C10A S1A C4A
MPLA 6 C11A C12A C13A C14A C15A C16A C4A O2A
MPLA 6 C5B C6B C7B C8B C9B C10B O1B C4B
MPLA 6 C11B C12B C13B C14B C15B C16B C4B O2B
WPDB -1
FMAP 2
PLAN -9
WGHT 0.070000 1.250000
FVAR 0.12888
S1A 4 0.067542 0.583457 -0.354239 11.00000 0.01724 0.01953 =
0.01686 0.00426 0.00110 0.00894
O2A 3 0.214230 0.607698 0.279851 11.00000 0.02312 0.02179 =
0.02044 -0.00463 -0.00700 0.01327
H2AA 2 0.233844 0.590257 0.291323 11.00000 0.04764
C2A 1 0.111011 0.555320 -0.292202 11.00000 0.01747 0.01726 =
0.01553 -0.00052 0.00040 0.00984
C3A 1 0.072356 0.502910 -0.216073 11.00000 0.01986 0.01525 =
0.01417 -0.00087 -0.00087 0.00869
AFIX 23
H3AA 2 0.094763 0.485019 -0.191053 11.00000 -1.20000
H3AB 2 0.041776 0.475765 -0.271137 11.00000 -1.20000
AFIX 0
C4A 1 0.043975 0.509827 -0.098497 11.00000 0.01584 0.01535 =
0.01286 0.00044 -0.00003 0.00733
C5A 1 0.015461 0.545261 -0.122241 11.00000 0.01431 0.01482 =
0.01714 -0.00327 -0.00416 0.00608
C6A 1 -0.022746 0.544402 -0.034734 11.00000 0.01827 0.02235 =
0.01652 -0.00115 -0.00211 0.00999
AFIX 43
H6AA 2 -0.030577 0.521299 0.036479 11.00000 -1.20000
AFIX 0
C7A 1 -0.049701 0.576043 -0.047926 11.00000 0.01717 0.02526 =
0.02189 -0.00575 -0.00403 0.01128
AFIX 43
H7AA 2 -0.075293 0.574580 0.013509 11.00000 -1.20000
AFIX 0
C8A 1 -0.038772 0.609967 -0.152343 11.00000 0.02106 0.02249 =
0.02777 -0.00666 -0.00772 0.01496
AFIX 43
H8AA 2 -0.056627 0.632062 -0.162417 11.00000 -1.20000
AFIX 0
C9A 1 -0.002019 0.611089 -0.240220 11.00000 0.02173 0.01508 =
0.02473 -0.00024 -0.00593 0.00923
AFIX 43
H9AA 2 0.005140 0.633920 -0.311659 11.00000 -1.20000
AFIX 0
C10A 1 0.025341 0.579130 -0.226858 11.00000 0.01300 0.01433 =
0.01814 -0.00363 -0.00270 0.00527
C11A 1 0.087636 0.535302 0.007394 11.00000 0.01598 0.01419 =
0.01331 0.00122 0.00190 0.00735
C12A 1 0.116008 0.507110 0.047992 11.00000 0.01999 0.01458 =
0.01660 -0.00048 0.00143 0.00899
AFIX 43
H12A 2 0.106546 0.471533 0.012555 11.00000 -1.20000
AFIX 0
C13A 1 0.157693 0.530039 0.138964 11.00000 0.02203 0.01973 =
0.01763 0.00193 0.00174 0.01371
AFIX 43
H13A 2 0.176431 0.510241 0.164527 11.00000 -1.20000
AFIX 0
C14A 1 0.171868 0.581974 0.192375 11.00000 0.01706 0.01916 =
0.01301 0.00005 -0.00043 0.00850
C15A 1 0.143381 0.609923 0.156347 11.00000 0.02166 0.01606 =
0.01633 -0.00110 0.00042 0.01102
AFIX 43
H15A 2 0.152036 0.644848 0.194044 11.00000 -1.20000
AFIX 0
C16A 1 0.102134 0.586706 0.064939 11.00000 0.01835 0.01688 =
0.01542 0.00121 0.00171 0.00992
AFIX 43
H16A 2 0.083164 0.606466 0.040790 11.00000 -1.20000
AFIX 0
C17A 1 -0.002203 0.448715 -0.062852 11.00000 0.01907 0.01521 =
0.02165 0.00196 0.00138 0.00633
AFIX 137
H17A 2 -0.018608 0.449367 0.017208 11.00000 -1.50000
H17B 2 0.014883 0.424515 -0.057472 11.00000 -1.50000
H17C 2 -0.032057 0.433657 -0.125773 11.00000 -1.50000
AFIX 0
C18A 1 0.131411 0.537495 -0.405714 11.00000 0.02762 0.02280 =
0.01888 0.00016 0.00484 0.01299
AFIX 137
H18A 2 0.158566 0.525736 -0.380505 11.00000 -1.50000
H18B 2 0.149838 0.569538 -0.462995 11.00000 -1.50000
H18C 2 0.098935 0.505758 -0.446571 11.00000 -1.50000
AFIX 0
C19A 1 0.161706 0.601958 -0.221724 11.00000 0.01585 0.01908 =
0.01997 0.00141 0.00111 0.00613
AFIX 137
H19A 2 0.183174 0.585929 -0.183314 11.00000 -1.50000
H19B 2 0.148060 0.617628 -0.157665 11.00000 -1.50000
H19C 2 0.186305 0.632145 -0.279119 11.00000 -1.50000
AFIX 0
O1B 3 0.158447 0.406665 0.932674 11.00000 0.01827 0.02227 =
0.01763 -0.00254 0.00220 0.00980
O2B 3 0.273348 0.549653 0.315063 11.00000 0.01802 0.02266 =
0.02069 0.00608 0.00371 0.00992
H2BA 2 0.303887 0.562152 0.302254 11.00000 0.04799
C2B 1 0.217636 0.443528 0.898991 11.00000 0.01639 0.01812 =
0.01633 0.00000 0.00042 0.00911
C3B 1 0.237650 0.410330 0.820196 11.00000 0.01511 0.01842 =
0.01543 0.00031 -0.00073 0.00919
AFIX 23
H3BA 2 0.236527 0.379643 0.871300 11.00000 -1.20000
H3BB 2 0.277672 0.436085 0.796631 11.00000 -1.20000
AFIX 0
C4B 1 0.202950 0.383802 0.701844 11.00000 0.01505 0.01635 =
0.01538 -0.00144 -0.00075 0.00891
C5B 1 0.140312 0.356963 0.734703 11.00000 0.01715 0.01597 =
0.01481 0.00171 -0.00006 0.00868
C6B 1 0.098324 0.316670 0.657048 11.00000 0.01994 0.01780 =
0.01837 0.00178 0.00065 0.00850
AFIX 43
H6BA 2 0.109449 0.306080 0.583206 11.00000 -1.20000
AFIX 0
C7B 1 0.040837 0.291681 0.684704 11.00000 0.01804 0.01764 =
0.02399 0.00295 -0.00429 0.00639
AFIX 43
H7BA 2 0.013154 0.264808 0.630064 11.00000 -1.20000
AFIX 0
C8B 1 0.024527 0.306640 0.793529 11.00000 0.01629 0.02005 =
0.02937 0.00815 0.00334 0.00914
AFIX 43
H8BA 2 -0.014596 0.290220 0.812946 11.00000 -1.20000
AFIX 0
C9B 1 0.064774 0.345132 0.873343 11.00000 0.01839 0.02060 =
0.02372 0.00437 0.00461 0.01165
AFIX 43
H9BA 2 0.053221 0.354462 0.948264 11.00000 -1.20000
AFIX 0
C10B 1 0.122788 0.370701 0.844774 11.00000 0.01714 0.01620 =
0.01720 0.00217 0.00181 0.00950
C11B 1 0.220247 0.427902 0.596940 11.00000 0.01745 0.01668 =
0.01281 -0.00303 -0.00083 0.00847
C12B 1 0.276944 0.457988 0.560196 11.00000 0.01534 0.02285 =
0.01815 0.00034 -0.00154 0.01152
AFIX 43
H12B 2 0.303611 0.450613 0.600347 11.00000 -1.20000
AFIX 0
C13B 1 0.295726 0.498417 0.466744 11.00000 0.01390 0.02070 =
0.01787 0.00023 0.00113 0.00730
AFIX 43
H13B 2 0.334633 0.518313 0.443991 11.00000 -1.20000
AFIX 0
C14B 1 0.257091 0.509469 0.406909 11.00000 0.01828 0.01519 =
0.01419 -0.00031 0.00094 0.00792
C15B 1 0.200331 0.479390 0.439834 11.00000 0.01752 0.02069 =
0.01507 -0.00176 -0.00184 0.01087
AFIX 43
H15B 2 0.173569 0.486049 0.397883 11.00000 -1.20000
AFIX 0
C16B 1 0.182420 0.439355 0.534450 11.00000 0.01281 0.01797 =
0.01762 -0.00282 -0.00046 0.00741
AFIX 43
H16B 2 0.143461 0.419423 0.556783 11.00000 -1.20000
AFIX 0
C17B 1 0.216439 0.337741 0.659531 11.00000 0.02296 0.02067 =
0.01724 -0.00077 0.00115 0.01239
AFIX 137
H17D 2 0.198267 0.322435 0.579713 11.00000 -1.50000
H17E 2 0.202044 0.307149 0.720709 11.00000 -1.50000
H17F 2 0.257579 0.354369 0.651283 11.00000 -1.50000
AFIX 0
C18B 1 0.249735 0.459779 1.021035 11.00000 0.02475 0.02585 =
0.01780 -0.00383 -0.00475 0.01466
AFIX 137
H18D 2 0.234309 0.477772 1.074708 11.00000 -1.50000
H18E 2 0.290004 0.486356 1.005559 11.00000 -1.50000
H18F 2 0.245536 0.425661 1.061329 11.00000 -1.50000
AFIX 0
C19B 1 0.222886 0.496061 0.836063 11.00000 0.02547 0.02189 =
0.01918 0.00004 -0.00015 0.01480
AFIX 137
H19D 2 0.195933 0.484461 0.767382 11.00000 -1.50000
H19E 2 0.261562 0.519535 0.804615 11.00000 -1.50000
H19F 2 0.214536 0.517939 0.895762 11.00000 -1.50000
HKLF 4
REM p12001_1n in R3
REM R1 = 0.0352 for 5973 Fo > 4sig(Fo) and 0.0374 for all 6250 data
REM 375 parameters refined using 1 restraints
END
WGHT 0.0598 1.2513
REM Highest difference peak 1.077, deepest hole -0.178, 1-sigma level 0.051
Q1 1 0.3333 0.6667 0.0904 10.33333 0.05 1.08
Q2 1 0.3333 0.6667 -0.4895 10.33333 0.05 1.03
Q3 1 0.3333 0.6667 -0.1389 10.33333 0.05 0.69
Q4 1 0.3333 0.6667 -0.2593 10.33333 0.05 0.66
Q5 1 0.3203 0.6765 -0.0167 11.00000 0.05 0.49
Q6 1 0.3373 0.6855 -0.3832 11.00000 0.05 0.44
Q7 1 0.0941 0.5301 -0.2484 11.00000 0.05 0.28
Q8 1 0.1368 0.5790 -0.2530 11.00000 0.05 0.25
Q9 1 0.2252 0.4725 0.8676 11.00000 0.05 0.24
;
#==============================================================================
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common
;
S-Thiadianin's, R-Dianin's empty Quasiracemate
;
_chemical_melting_point ?
_chemical_compound_source ?
_chemical_absolute_configuration ad
_chemical_formula_iupac ?
_chemical_formula_moiety 'C18 H20 O S, C18 H20 O2'
_chemical_formula_sum 'C36 H40 O3 S'
_chemical_formula_weight 552.74
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_space_group_id
1
_space_group_crystal_system Trigonal
_space_group_IT_number 146
_space_group_name_H-M_alt 'R 3'
_space_group_name_Hall 'R 3'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
_cell_length_a 27.2258(4)
_cell_length_b 27.2258(4)
_cell_length_c 10.8365(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 120.00
_cell_volume 6956.3(2)
_cell_formula_units_Z 9
_cell_measurement_temperature 90(1)
_cell_measurement_reflns_used 9674
_cell_measurement_theta_min 3.2438
_cell_measurement_theta_max 76.0779
_exptl_crystal_description Lath
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.187
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2664
_exptl_absorpt_coefficient_mu 1.183
_exptl_absorpt_correction_T_min 0.90365
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 90(1)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5598
_diffrn_measurement_method '\w scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17968
_diffrn_reflns_av_R_equivalents 0.0296
_diffrn_reflns_av_sigmaI/netI 0.0368
_diffrn_reflns_limit_h_min -34
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_k_min -30
_diffrn_reflns_limit_k_max 33
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 9.01
_diffrn_reflns_theta_max 74.31
_reflns_number_total 6250
_reflns_number_gt 5973
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution 'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+1.2500P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.002(12)
_refine_ls_number_reflns 6250
_refine_ls_number_parameters 375
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0374
_refine_ls_R_factor_gt 0.0352
_refine_ls_wR_factor_ref 0.0975
_refine_ls_wR_factor_gt 0.0952
_refine_ls_goodness_of_fit_ref 1.002
_refine_ls_restrained_S_all 1.002
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.067542(17) 0.583457(16) -0.35424(4) 0.01799(10) Uani 1 1 d . . .
O2A O 0.21423(6) 0.60770(6) 0.27985(11) 0.0209(3) Uani 1 1 d . . .
H2AA H 0.2338(15) 0.5903(15) 0.291(3) 0.048(9) Uiso 1 1 d . . .
C2A C 0.11101(7) 0.55532(7) -0.29220(14) 0.0162(3) Uani 1 1 d . . .
C3A C 0.07236(7) 0.50291(7) -0.21607(15) 0.0165(3) Uani 1 1 d . . .
H3AA H 0.0948 0.4850 -0.1911 0.020 Uiso 1 1 calc R . .
H3AB H 0.0418 0.4758 -0.2711 0.020 Uiso 1 1 calc R . .
C4A C 0.04398(7) 0.50983(7) -0.09850(14) 0.0149(3) Uani 1 1 d . . .
C5A C 0.01546(7) 0.54526(7) -0.12224(15) 0.0160(3) Uani 1 1 d . . .
C6A C -0.02275(7) 0.54440(8) -0.03473(16) 0.0191(3) Uani 1 1 d . . .
H6AA H -0.0306 0.5213 0.0365 0.023 Uiso 1 1 calc R . .
C7A C -0.04970(8) 0.57604(8) -0.04793(17) 0.0211(3) Uani 1 1 d . . .
H7AA H -0.0753 0.5746 0.0135 0.025 Uiso 1 1 calc R . .
C8A C -0.03877(8) 0.60997(8) -0.15234(17) 0.0220(4) Uani 1 1 d . . .
H8AA H -0.0566 0.6321 -0.1624 0.026 Uiso 1 1 calc R . .
C9A C -0.00202(8) 0.61109(7) -0.24022(17) 0.0205(3) Uani 1 1 d . . .
H9AA H 0.0051 0.6339 -0.3117 0.025 Uiso 1 1 calc R . .
C10A C 0.02534(7) 0.57913(7) -0.22686(15) 0.0159(3) Uani 1 1 d . . .
C11A C 0.08764(7) 0.53530(7) 0.00739(14) 0.0146(3) Uani 1 1 d . . .
C12A C 0.11601(7) 0.50711(7) 0.04799(15) 0.0169(3) Uani 1 1 d . . .
H12A H 0.1065 0.4715 0.0126 0.020 Uiso 1 1 calc R . .
C13A C 0.15769(8) 0.53004(8) 0.13896(16) 0.0183(3) Uani 1 1 d . . .
H13A H 0.1764 0.5102 0.1645 0.022 Uiso 1 1 calc R . .
C14A C 0.17187(7) 0.58197(7) 0.19238(14) 0.0167(3) Uani 1 1 d . . .
C15A C 0.14338(8) 0.60992(7) 0.15635(15) 0.0173(3) Uani 1 1 d . . .
H15A H 0.1520 0.6448 0.1940 0.021 Uiso 1 1 calc R . .
C16A C 0.10213(7) 0.58671(7) 0.06494(15) 0.0164(3) Uani 1 1 d . . .
H16A H 0.0832 0.6065 0.0408 0.020 Uiso 1 1 calc R . .
C17A C -0.00220(8) 0.44872(7) -0.06285(16) 0.0196(3) Uani 1 1 d . . .
H17A H -0.0186 0.4494 0.0172 0.029 Uiso 1 1 calc R . .
H17B H 0.0149 0.4245 -0.0575 0.029 Uiso 1 1 calc R . .
H17C H -0.0321 0.4337 -0.1258 0.029 Uiso 1 1 calc R . .
C18A C 0.13141(8) 0.53749(8) -0.40571(17) 0.0229(4) Uani 1 1 d . . .
H18A H 0.1586 0.5257 -0.3805 0.034 Uiso 1 1 calc R . .
H18B H 0.1498 0.5695 -0.4630 0.034 Uiso 1 1 calc R . .
H18C H 0.0989 0.5058 -0.4466 0.034 Uiso 1 1 calc R . .
C19A C 0.16171(7) 0.60196(8) -0.22172(16) 0.0195(3) Uani 1 1 d . . .
H19A H 0.1832 0.5859 -0.1833 0.029 Uiso 1 1 calc R . .
H19B H 0.1481 0.6176 -0.1577 0.029 Uiso 1 1 calc R . .
H19C H 0.1863 0.6321 -0.2791 0.029 Uiso 1 1 calc R . .
O1B O 0.15845(5) 0.40666(6) 0.93267(11) 0.0195(3) Uani 1 1 d . . .
O2B O 0.27335(6) 0.54965(6) 0.31506(11) 0.0206(3) Uani 1 1 d . . .
H2BA H 0.3039(17) 0.5622(16) 0.302(3) 0.048(9) Uiso 1 1 d . . .
C2B C 0.21764(7) 0.44353(7) 0.89899(15) 0.0167(3) Uani 1 1 d . . .
C3B C 0.23765(7) 0.41033(7) 0.82020(15) 0.0160(3) Uani 1 1 d . . .
H3BA H 0.2365 0.3796 0.8713 0.019 Uiso 1 1 calc R . .
H3BB H 0.2777 0.4361 0.7966 0.019 Uiso 1 1 calc R . .
C4B C 0.20295(7) 0.38380(7) 0.70184(15) 0.0151(3) Uani 1 1 d . . .
C5B C 0.14031(7) 0.35696(7) 0.73470(15) 0.0158(3) Uani 1 1 d . . .
C6B C 0.09832(8) 0.31667(7) 0.65705(16) 0.0191(3) Uani 1 1 d . . .
H6BA H 0.1094 0.3061 0.5832 0.023 Uiso 1 1 calc R . .
C7B C 0.04084(8) 0.29168(8) 0.68470(17) 0.0210(3) Uani 1 1 d . . .
H7BA H 0.0132 0.2648 0.6301 0.025 Uiso 1 1 calc R . .
C8B C 0.02453(7) 0.30664(8) 0.79353(17) 0.0219(3) Uani 1 1 d . . .
H8BA H -0.0146 0.2902 0.8129 0.026 Uiso 1 1 calc R . .
C9B C 0.06477(7) 0.34513(7) 0.87334(17) 0.0201(3) Uani 1 1 d . . .
H9BA H 0.0532 0.3545 0.9483 0.024 Uiso 1 1 calc R . .
C10B C 0.12279(7) 0.37070(7) 0.84477(15) 0.0163(3) Uani 1 1 d . . .
C11B C 0.22025(7) 0.42790(7) 0.59694(15) 0.0157(3) Uani 1 1 d . . .
C12B C 0.27694(7) 0.45799(8) 0.56020(15) 0.0179(3) Uani 1 1 d . . .
H12B H 0.3036 0.4506 0.6003 0.021 Uiso 1 1 calc R . .
C13B C 0.29573(7) 0.49842(8) 0.46674(15) 0.0181(3) Uani 1 1 d . . .
H13B H 0.3346 0.5183 0.4440 0.022 Uiso 1 1 calc R . .
C14B C 0.25709(7) 0.50947(7) 0.40691(15) 0.0161(3) Uani 1 1 d . . .
C15B C 0.20033(7) 0.47939(7) 0.43983(15) 0.0172(3) Uani 1 1 d . . .
H15B H 0.1736 0.4860 0.3979 0.021 Uiso 1 1 calc R . .
C16B C 0.18242(7) 0.43936(7) 0.53445(15) 0.0163(3) Uani 1 1 d . . .
H16B H 0.1435 0.4194 0.5568 0.020 Uiso 1 1 calc R . .
C17B C 0.21644(8) 0.33774(8) 0.65953(16) 0.0196(3) Uani 1 1 d . . .
H17D H 0.1983 0.3224 0.5797 0.029 Uiso 1 1 calc R . .
H17E H 0.2020 0.3071 0.7207 0.029 Uiso 1 1 calc R . .
H17F H 0.2576 0.3544 0.6513 0.029 Uiso 1 1 calc R . .
C18B C 0.24974(8) 0.45978(8) 1.02104(16) 0.0219(3) Uani 1 1 d . . .
H18D H 0.2343 0.4778 1.0747 0.033 Uiso 1 1 calc R . .
H18E H 0.2900 0.4864 1.0056 0.033 Uiso 1 1 calc R . .
H18F H 0.2455 0.4257 1.0613 0.033 Uiso 1 1 calc R . .
C19B C 0.22289(8) 0.49606(8) 0.83606(16) 0.0209(4) Uani 1 1 d . . .
H19D H 0.1959 0.4845 0.7674 0.031 Uiso 1 1 calc R . .
H19E H 0.2616 0.5195 0.8046 0.031 Uiso 1 1 calc R . .
H19F H 0.2145 0.5179 0.8958 0.031 Uiso 1 1 calc R . .
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
S1A 0.01724(19) 0.0195(2) 0.01686(18) 0.00426(14) 0.00110(14) 0.00894(17)
O2A 0.0231(6) 0.0218(6) 0.0204(6) -0.0046(5) -0.0070(5) 0.0133(5)
C2A 0.0175(8) 0.0173(8) 0.0155(7) -0.0005(6) 0.0004(6) 0.0098(7)
C3A 0.0199(8) 0.0153(8) 0.0142(7) -0.0009(6) -0.0009(6) 0.0087(7)
C4A 0.0158(7) 0.0153(7) 0.0129(7) 0.0004(6) 0.0000(6) 0.0073(6)
C5A 0.0143(7) 0.0148(7) 0.0171(7) -0.0033(6) -0.0042(6) 0.0061(6)
C6A 0.0183(8) 0.0224(8) 0.0165(7) -0.0012(6) -0.0021(6) 0.0100(7)
C7A 0.0172(8) 0.0253(9) 0.0219(8) -0.0057(7) -0.0040(6) 0.0113(7)
C8A 0.0211(8) 0.0225(8) 0.0278(9) -0.0067(7) -0.0077(7) 0.0150(7)
C9A 0.0217(8) 0.0151(8) 0.0247(8) -0.0002(6) -0.0059(7) 0.0092(7)
C10A 0.0130(7) 0.0143(7) 0.0181(7) -0.0036(6) -0.0027(5) 0.0053(6)
C11A 0.0160(8) 0.0142(7) 0.0133(7) 0.0012(6) 0.0019(6) 0.0074(6)
C12A 0.0200(8) 0.0146(7) 0.0166(7) -0.0005(6) 0.0014(6) 0.0090(6)
C13A 0.0220(8) 0.0197(8) 0.0176(8) 0.0019(6) 0.0017(6) 0.0137(7)
C14A 0.0171(8) 0.0192(8) 0.0130(7) 0.0001(6) -0.0004(6) 0.0085(7)
C15A 0.0217(8) 0.0161(8) 0.0163(7) -0.0011(6) 0.0004(6) 0.0110(7)
C16A 0.0183(8) 0.0169(8) 0.0154(7) 0.0012(6) 0.0017(6) 0.0099(6)
C17A 0.0191(8) 0.0152(8) 0.0217(8) 0.0020(6) 0.0014(6) 0.0063(7)
C18A 0.0276(9) 0.0228(8) 0.0189(8) 0.0002(6) 0.0048(7) 0.0130(7)
C19A 0.0159(8) 0.0191(8) 0.0200(8) 0.0014(6) 0.0011(6) 0.0061(7)
O1B 0.0183(6) 0.0223(6) 0.0176(6) -0.0025(4) 0.0022(4) 0.0098(5)
O2B 0.0180(6) 0.0227(7) 0.0207(6) 0.0061(5) 0.0037(5) 0.0099(5)
C2B 0.0164(8) 0.0181(8) 0.0163(7) 0.0000(6) 0.0004(6) 0.0091(7)
C3B 0.0151(7) 0.0184(8) 0.0154(7) 0.0003(6) -0.0007(6) 0.0092(7)
C4B 0.0150(8) 0.0164(7) 0.0154(7) -0.0014(6) -0.0007(6) 0.0089(6)
C5B 0.0171(8) 0.0160(7) 0.0148(7) 0.0017(6) -0.0001(6) 0.0087(6)
C6B 0.0199(8) 0.0178(8) 0.0184(8) 0.0018(6) 0.0006(6) 0.0085(7)
C7B 0.0180(8) 0.0176(8) 0.0240(8) 0.0029(6) -0.0043(6) 0.0064(7)
C8B 0.0163(8) 0.0201(8) 0.0294(9) 0.0081(7) 0.0033(7) 0.0091(7)
C9B 0.0184(8) 0.0206(8) 0.0237(8) 0.0044(6) 0.0046(6) 0.0116(7)
C10B 0.0171(8) 0.0162(7) 0.0172(7) 0.0022(6) 0.0018(6) 0.0095(6)
C11B 0.0175(8) 0.0167(8) 0.0128(7) -0.0030(6) -0.0008(6) 0.0085(7)
C12B 0.0153(8) 0.0228(8) 0.0181(8) 0.0003(6) -0.0015(6) 0.0115(7)
C13B 0.0139(7) 0.0207(8) 0.0179(8) 0.0002(6) 0.0011(6) 0.0073(6)
C14B 0.0183(8) 0.0152(7) 0.0142(7) -0.0003(6) 0.0009(6) 0.0079(6)
C15B 0.0175(8) 0.0207(8) 0.0151(7) -0.0018(6) -0.0018(6) 0.0109(7)
C16B 0.0128(7) 0.0180(8) 0.0176(7) -0.0028(6) -0.0005(6) 0.0074(6)
C17B 0.0230(8) 0.0207(8) 0.0172(8) -0.0008(6) 0.0011(6) 0.0124(7)
C18B 0.0247(9) 0.0258(9) 0.0178(8) -0.0038(7) -0.0048(7) 0.0147(7)
C19B 0.0255(9) 0.0219(8) 0.0192(8) 0.0000(6) -0.0002(6) 0.0148(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1A C10A 1.7618(17) . ?
S1A C2A 1.8292(17) . ?
O2A C14A 1.383(2) . ?
C2A C3A 1.524(2) . ?
C2A C18A 1.525(2) . ?
C2A C19A 1.532(2) . ?
C3A C4A 1.550(2) . ?
C4A C5A 1.532(2) . ?
C4A C11A 1.545(2) . ?
C4A C17A 1.551(2) . ?
C5A C10A 1.400(2) . ?
C5A C6A 1.399(2) . ?
C6A C7A 1.390(3) . ?
C7A C8A 1.395(3) . ?
C8A C9A 1.371(3) . ?
C9A C10A 1.408(2) . ?
C11A C16A 1.397(2) . ?
C11A C12A 1.404(2) . ?
C12A C13A 1.393(2) . ?
C13A C14A 1.392(2) . ?
C14A C15A 1.387(2) . ?
C15A C16A 1.390(2) . ?
O1B C10B 1.363(2) . ?
O1B C2B 1.456(2) . ?
O2B C14B 1.378(2) . ?
C2B C18B 1.524(2) . ?
C2B C19B 1.525(2) . ?
C2B C3B 1.528(2) . ?
C3B C4B 1.542(2) . ?
C4B C5B 1.524(2) . ?
C4B C17B 1.542(2) . ?
C4B C11B 1.546(2) . ?
C5B C10B 1.403(2) . ?
C5B C6B 1.402(2) . ?
C6B C7B 1.392(3) . ?
C7B C8B 1.391(3) . ?
C8B C9B 1.378(3) . ?
C9B C10B 1.406(2) . ?
C11B C16B 1.392(2) . ?
C11B C12B 1.396(2) . ?
C12B C13B 1.391(2) . ?
C13B C14B 1.391(2) . ?
C14B C15B 1.386(2) . ?
C15B C16B 1.395(2) . ?
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
C10A S1A C2A 102.76(8) . . ?
C3A C2A C18A 109.24(14) . . ?
C3A C2A C19A 114.85(14) . . ?
C18A C2A C19A 110.19(14) . . ?
C3A C2A S1A 107.61(12) . . ?
C18A C2A S1A 104.57(11) . . ?
C19A C2A S1A 109.84(12) . . ?
C2A C3A C4A 118.96(14) . . ?
C5A C4A C11A 111.12(13) . . ?
C5A C4A C3A 112.26(13) . . ?
C11A C4A C3A 110.29(13) . . ?
C5A C4A C17A 108.84(13) . . ?
C11A C4A C17A 109.00(13) . . ?
C3A C4A C17A 105.09(13) . . ?
C10A C5A C6A 117.15(15) . . ?
C10A C5A C4A 124.03(15) . . ?
C6A C5A C4A 118.82(15) . . ?
C7A C6A C5A 122.57(16) . . ?
C6A C7A C8A 119.31(17) . . ?
C9A C8A C7A 119.33(16) . . ?
C8A C9A C10A 121.39(17) . . ?
C5A C10A C9A 120.25(16) . . ?
C5A C10A S1A 125.64(13) . . ?
C9A C10A S1A 114.02(13) . . ?
C16A C11A C12A 116.79(15) . . ?
C16A C11A C4A 123.37(15) . . ?
C12A C11A C4A 119.83(14) . . ?
C13A C12A C11A 121.61(16) . . ?
C14A C13A C12A 119.96(16) . . ?
O2A C14A C15A 117.96(15) . . ?
O2A C14A C13A 122.48(15) . . ?
C15A C14A C13A 119.55(16) . . ?
C14A C15A C16A 119.83(16) . . ?
C15A C16A C11A 122.22(16) . . ?
C10B O1B C2B 117.73(12) . . ?
O1B C2B C18B 105.01(14) . . ?
O1B C2B C19B 108.12(14) . . ?
C18B C2B C19B 110.15(14) . . ?
O1B C2B C3B 109.36(13) . . ?
C18B C2B C3B 109.53(14) . . ?
C19B C2B C3B 114.26(14) . . ?
C2B C3B C4B 115.19(14) . . ?
C5B C4B C3B 107.87(13) . . ?
C5B C4B C17B 110.12(13) . . ?
C3B C4B C17B 106.80(13) . . ?
C5B C4B C11B 112.18(13) . . ?
C3B C4B C11B 111.75(13) . . ?
C17B C4B C11B 108.00(13) . . ?
C10B C5B C6B 117.78(15) . . ?
C10B C5B C4B 121.26(15) . . ?
C6B C5B C4B 120.95(14) . . ?
C7B C6B C5B 122.08(16) . . ?
C8B C7B C6B 119.01(17) . . ?
C9B C8B C7B 120.40(16) . . ?
C8B C9B C10B 120.52(17) . . ?
O1B C10B C5B 124.79(15) . . ?
O1B C10B C9B 114.98(15) . . ?
C5B C10B C9B 120.19(16) . . ?
C16B C11B C12B 117.05(16) . . ?
C16B C11B C4B 124.02(15) . . ?
C12B C11B C4B 118.92(15) . . ?
C13B C12B C11B 122.22(15) . . ?
C12B C13B C14B 119.47(16) . . ?
O2B C14B C15B 118.40(16) . . ?
O2B C14B C13B 122.08(16) . . ?
C15B C14B C13B 119.52(16) . . ?
C14B C15B C16B 120.13(16) . . ?
C11B C16B C15B 121.60(15) . . ?
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
C10A S1A C2A C3A 43.39(12) . . . . ?
C10A S1A C2A C18A 159.48(12) . . . . ?
C10A S1A C2A C19A -82.30(12) . . . . ?
C18A C2A C3A C4A -177.29(14) . . . . ?
C19A C2A C3A C4A 58.3(2) . . . . ?
S1A C2A C3A C4A -64.31(16) . . . . ?
C2A C3A C4A C5A 48.8(2) . . . . ?
C2A C3A C4A C11A -75.73(18) . . . . ?
C2A C3A C4A C17A 166.93(14) . . . . ?
C11A C4A C5A C10A 109.09(17) . . . . ?
C3A C4A C5A C10A -15.0(2) . . . . ?
C17A C4A C5A C10A -130.86(16) . . . . ?
C11A C4A C5A C6A -70.64(19) . . . . ?
C3A C4A C5A C6A 165.32(15) . . . . ?
C17A C4A C5A C6A 49.41(19) . . . . ?
C10A C5A C6A C7A -0.9(2) . . . . ?
C4A C5A C6A C7A 178.83(16) . . . . ?
C5A C6A C7A C8A 0.3(3) . . . . ?
C6A C7A C8A C9A 0.5(3) . . . . ?
C7A C8A C9A C10A -0.6(3) . . . . ?
C6A C5A C10A C9A 0.8(2) . . . . ?
C4A C5A C10A C9A -178.92(15) . . . . ?
C6A C5A C10A S1A -175.38(13) . . . . ?
C4A C5A C10A S1A 4.9(2) . . . . ?
C8A C9A C10A C5A -0.1(2) . . . . ?
C8A C9A C10A S1A 176.52(14) . . . . ?
C2A S1A C10A C5A -18.73(16) . . . . ?
C2A S1A C10A C9A 164.88(12) . . . . ?
C5A C4A C11A C16A -5.3(2) . . . . ?
C3A C4A C11A C16A 119.84(17) . . . . ?
C17A C4A C11A C16A -125.26(17) . . . . ?
C5A C4A C11A C12A 176.36(14) . . . . ?
C3A C4A C11A C12A -58.49(19) . . . . ?
C17A C4A C11A C12A 56.40(19) . . . . ?
C16A C11A C12A C13A -1.7(2) . . . . ?
C4A C11A C12A C13A 176.77(15) . . . . ?
C11A C12A C13A C14A 0.4(3) . . . . ?
C12A C13A C14A O2A -177.68(16) . . . . ?
C12A C13A C14A C15A 1.4(3) . . . . ?
O2A C14A C15A C16A 177.32(15) . . . . ?
C13A C14A C15A C16A -1.8(3) . . . . ?
C14A C15A C16A C11A 0.4(3) . . . . ?
C12A C11A C16A C15A 1.3(2) . . . . ?
C4A C11A C16A C15A -177.11(15) . . . . ?
C10B O1B C2B C18B -158.17(14) . . . . ?
C10B O1B C2B C19B 84.24(17) . . . . ?
C10B O1B C2B C3B -40.72(19) . . . . ?
O1B C2B C3B C4B 57.14(18) . . . . ?
C18B C2B C3B C4B 171.71(14) . . . . ?
C19B C2B C3B C4B -64.18(19) . . . . ?
C2B C3B C4B C5B -43.76(18) . . . . ?
C2B C3B C4B C17B -162.10(14) . . . . ?
C2B C3B C4B C11B 80.00(18) . . . . ?
C3B C4B C5B C10B 16.3(2) . . . . ?
C17B C4B C5B C10B 132.48(16) . . . . ?
C11B C4B C5B C10B -107.22(17) . . . . ?
C3B C4B C5B C6B -162.23(15) . . . . ?
C17B C4B C5B C6B -46.0(2) . . . . ?
C11B C4B C5B C6B 74.28(19) . . . . ?
C10B C5B C6B C7B 1.7(2) . . . . ?
C4B C5B C6B C7B -179.77(16) . . . . ?
C5B C6B C7B C8B -0.8(3) . . . . ?
C6B C7B C8B C9B -0.8(3) . . . . ?
C7B C8B C9B C10B 1.3(3) . . . . ?
C2B O1B C10B C5B 15.2(2) . . . . ?
C2B O1B C10B C9B -167.20(15) . . . . ?
C6B C5B C10B O1B 176.37(16) . . . . ?
C4B C5B C10B O1B -2.2(2) . . . . ?
C6B C5B C10B C9B -1.1(2) . . . . ?
C4B C5B C10B C9B -179.64(15) . . . . ?
C8B C9B C10B O1B -178.08(15) . . . . ?
C8B C9B C10B C5B -0.4(3) . . . . ?
C5B C4B C11B C16B -3.7(2) . . . . ?
C3B C4B C11B C16B -124.97(17) . . . . ?
C17B C4B C11B C16B 117.86(18) . . . . ?
C5B C4B C11B C12B 177.21(15) . . . . ?
C3B C4B C11B C12B 55.9(2) . . . . ?
C17B C4B C11B C12B -61.27(19) . . . . ?
C16B C11B C12B C13B 1.0(2) . . . . ?
C4B C11B C12B C13B -179.84(15) . . . . ?
C11B C12B C13B C14B -0.2(3) . . . . ?
C12B C13B C14B O2B 178.95(15) . . . . ?
C12B C13B C14B C15B -1.1(3) . . . . ?
O2B C14B C15B C16B -178.42(14) . . . . ?
C13B C14B C15B C16B 1.6(2) . . . . ?
C12B C11B C16B C15B -0.4(2) . . . . ?
C4B C11B C16B C15B -179.57(15) . . . . ?
C14B C15B C16B C11B -0.8(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2A H2AA O2B 0.88(4) 1.91(4) 2.789(2) 178(3) .
O2B H2BA O2A 0.74(4) 2.10(4) 2.831(2) 173(4) 2_665
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 74.31
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 1.077
_refine_diff_density_min -0.178
_refine_diff_density_rms 0.051
_database_code_depnum_ccdc_archive 'CCDC 933472'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_p11140
#==============================================================================
_iucr_refine_instructions_details
;
TITL p11140 in R3
CELL 1.54178 27.3283 27.3283 10.8327 90.000 90.000 120.000
ZERR 3.00 0.0004 0.0004 0.0003 0.000 0.000 0.000
LATT -3
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SFAC C H O S CL
UNIT 327 363 28.50 9 12
SIZE 0.25 0.20 0.15
SHEL 5.00 0.80
TEMP -173
L.S. 12
EADP CL2 CL3
DFIX 1.75 C1 CL1 C1 CL2 C2 CL3 C2 CL4
CONF
ACTA
EQIV$1 1.00-Y, 1.00+x-y, 0.00+Z
HTAB O2A O2B
HTAB O2B O2A_$1
RTAB DIST C17A C18A
RTAB DIST C17B C18B
MPLA 6 C5A C6A C7A C8A C9A C10A S1A C4A
MPLA 6 C11A C12A C13A C14A C15A C16A C4A O2A
MPLA 6 C5B C6B C7B C8B C9B C10B O1B C4B
MPLA 6 C11B C12B C13B C14B C15B C16B C4B O2B
WPDB -1
FMAP 2
TWIN
PLAN -9
WGHT 0.095000
BASF 0.03208
FVAR 0.07351
S1A 4 0.066609 0.583985 -0.354009 11.00000 0.01494 0.01812 =
0.01572 0.00467 0.00148 0.00818
O2A 3 0.211059 0.605235 0.283186 11.00000 0.02297 0.01980 =
0.01978 -0.00396 -0.00688 0.01279
H2AA 2 0.229440 0.588547 0.290052 11.00000 0.03343
C2A 1 0.108976 0.554488 -0.294808 11.00000 0.01556 0.01501 =
0.01481 0.00032 0.00167 0.00834
C3A 1 0.070261 0.502353 -0.217505 11.00000 0.01730 0.01219 =
0.01466 -0.00061 0.00045 0.00670
AFIX 23
H3AA 2 0.092289 0.484076 -0.193509 11.00000 -1.20000
H3AB 2 0.039280 0.475509 -0.271821 11.00000 -1.20000
AFIX 0
C4A 1 0.043059 0.509790 -0.098949 11.00000 0.01445 0.01360 =
0.01408 -0.00052 0.00085 0.00700
C5A 1 0.014924 0.545631 -0.122216 11.00000 0.01391 0.01432 =
0.01675 -0.00269 -0.00299 0.00613
C6A 1 -0.023062 0.544709 -0.034004 11.00000 0.01586 0.01970 =
0.01700 -0.00067 -0.00104 0.01029
AFIX 43
H6AA 2 -0.030898 0.521568 0.037031 11.00000 -1.20000
AFIX 0
C7A 1 -0.049746 0.576574 -0.046882 11.00000 0.01606 0.02540 =
0.02122 -0.00756 -0.00298 0.01258
AFIX 43
H7AA 2 -0.074945 0.575377 0.015025 11.00000 -1.20000
AFIX 0
C8A 1 -0.039172 0.610065 -0.150953 11.00000 0.01907 0.02112 =
0.02589 -0.00584 -0.00648 0.01425
AFIX 43
H8AA 2 -0.057187 0.631872 -0.160877 11.00000 -1.20000
AFIX 0
C9A 1 -0.002454 0.611475 -0.239594 11.00000 0.01889 0.01492 =
0.02191 -0.00025 -0.00396 0.00891
AFIX 43
H9AA 2 0.004629 0.634292 -0.310916 11.00000 -1.20000
AFIX 0
C10A 1 0.024777 0.579626 -0.226215 11.00000 0.01221 0.01342 =
0.01911 -0.00222 -0.00059 0.00455
C11A 1 0.086696 0.535214 0.006895 11.00000 0.01657 0.01461 =
0.01098 0.00062 0.00103 0.00835
C12A 1 0.114456 0.506643 0.048051 11.00000 0.01719 0.01399 =
0.01616 0.00036 0.00154 0.00851
AFIX 43
H12A 2 0.105075 0.471367 0.011756 11.00000 -1.20000
AFIX 0
C13A 1 0.155093 0.528444 0.140001 11.00000 0.01878 0.01921 =
0.01721 0.00229 0.00089 0.01199
AFIX 43
H13A 2 0.173127 0.508179 0.166102 11.00000 -1.20000
AFIX 0
C14A 1 0.169538 0.580494 0.194444 11.00000 0.01553 0.01873 =
0.01283 -0.00045 -0.00010 0.00834
C15A 1 0.142071 0.608933 0.157061 11.00000 0.01848 0.01351 =
0.01606 -0.00114 0.00070 0.00868
AFIX 43
H15A 2 0.150953 0.643824 0.194655 11.00000 -1.20000
AFIX 0
C16A 1 0.101418 0.586400 0.064345 11.00000 0.01639 0.01542 =
0.01444 0.00083 0.00079 0.00944
AFIX 43
H16A 2 0.083113 0.606564 0.039417 11.00000 -1.20000
AFIX 0
C17A 1 -0.003180 0.449137 -0.062912 11.00000 0.01577 0.01566 =
0.01886 0.00289 0.00082 0.00572
AFIX 137
H17A 2 -0.018618 0.449869 0.018279 11.00000 -1.50000
H17B 2 0.013349 0.424546 -0.059746 11.00000 -1.50000
H17C 2 -0.033508 0.434645 -0.124484 11.00000 -1.50000
AFIX 0
C18A 1 0.127933 0.535782 -0.409947 11.00000 0.02307 0.02313 =
0.01784 -0.00015 0.00492 0.01207
AFIX 137
H18A 2 0.154115 0.522791 -0.385803 11.00000 -1.50000
H18B 2 0.146928 0.567713 -0.467034 11.00000 -1.50000
H18C 2 0.094873 0.504882 -0.450606 11.00000 -1.50000
AFIX 0
C19A 1 0.160592 0.600156 -0.226022 11.00000 0.01453 0.01661 =
0.01883 0.00044 0.00110 0.00596
AFIX 137
H19A 2 0.182052 0.583584 -0.190784 11.00000 -1.50000
H19B 2 0.148141 0.615760 -0.159603 11.00000 -1.50000
H19C 2 0.184635 0.630369 -0.283631 11.00000 -1.50000
AFIX 0
O1B 3 0.157762 0.406187 0.932583 11.00000 0.01562 0.01902 =
0.01661 -0.00361 0.00168 0.00702
O2B 3 0.273089 0.548947 0.314024 11.00000 0.01757 0.02434 =
0.02072 0.00793 0.00408 0.01116
H2BA 2 0.307518 0.561871 0.300722 11.00000 0.03911
C2B 1 0.216840 0.442968 0.899933 11.00000 0.01532 0.01501 =
0.01495 -0.00096 -0.00063 0.00790
C3B 1 0.236975 0.410282 0.820596 11.00000 0.01383 0.01524 =
0.01402 0.00024 -0.00086 0.00814
AFIX 23
H3BA 2 0.235928 0.379610 0.871213 11.00000 -1.20000
H3BB 2 0.276836 0.436097 0.797190 11.00000 -1.20000
AFIX 0
C4B 1 0.202378 0.384094 0.701792 11.00000 0.01492 0.01336 =
0.01241 -0.00202 -0.00215 0.00750
C5B 1 0.140047 0.357311 0.734123 11.00000 0.01472 0.01152 =
0.01421 0.00193 0.00018 0.00677
C6B 1 0.098371 0.317368 0.655862 11.00000 0.01782 0.01700 =
0.01731 0.00270 0.00126 0.00880
AFIX 43
H6BA 2 0.109560 0.307049 0.581825 11.00000 -1.20000
AFIX 0
C7B 1 0.041118 0.292384 0.683351 11.00000 0.01531 0.01664 =
0.02110 0.00170 -0.00426 0.00450
AFIX 43
H7BA 2 0.013680 0.265632 0.628430 11.00000 -1.20000
AFIX 0
C8B 1 0.024496 0.306909 0.791682 11.00000 0.01355 0.01934 =
0.02706 0.00760 0.00304 0.00769
AFIX 43
H8BA 2 -0.014530 0.290556 0.810592 11.00000 -1.20000
AFIX 0
C9B 1 0.064608 0.345133 0.872172 11.00000 0.01586 0.01671 =
0.02134 0.00242 0.00187 0.00856
AFIX 43
H9BA 2 0.053105 0.354265 0.947334 11.00000 -1.20000
AFIX 0
C10B 1 0.122038 0.370425 0.843492 11.00000 0.01733 0.01247 =
0.01690 0.00203 -0.00035 0.00848
C11B 1 0.219785 0.427843 0.597608 11.00000 0.01573 0.01290 =
0.01251 -0.00204 -0.00028 0.00719
C12B 1 0.276507 0.457842 0.560593 11.00000 0.01332 0.01954 =
0.01569 -0.00007 -0.00114 0.00914
AFIX 43
H12B 2 0.303102 0.450646 0.601116 11.00000 -1.20000
AFIX 0
C13B 1 0.295148 0.497820 0.466433 11.00000 0.01308 0.02113 =
0.01803 0.00056 0.00101 0.00756
AFIX 43
H13B 2 0.333867 0.517434 0.443309 11.00000 -1.20000
AFIX 0
C14B 1 0.256787 0.508835 0.406554 11.00000 0.01678 0.01644 =
0.01373 0.00094 0.00057 0.00873
C15B 1 0.200197 0.479454 0.439274 11.00000 0.01523 0.01779 =
0.01506 -0.00170 -0.00212 0.00918
AFIX 43
H15B 2 0.173736 0.486458 0.397529 11.00000 -1.20000
AFIX 0
C16B 1 0.182253 0.439400 0.534175 11.00000 0.01132 0.01574 =
0.01664 -0.00349 -0.00102 0.00601
AFIX 43
H16B 2 0.143387 0.419495 0.556058 11.00000 -1.20000
AFIX 0
C17B 1 0.216062 0.338176 0.659903 11.00000 0.02150 0.01848 =
0.01708 -0.00105 0.00063 0.01294
AFIX 137
H17D 2 0.197991 0.322764 0.580111 11.00000 -1.50000
H17E 2 0.201806 0.307796 0.721330 11.00000 -1.50000
H17F 2 0.257063 0.354859 0.651712 11.00000 -1.50000
AFIX 0
C18B 1 0.248124 0.458037 1.022533 11.00000 0.02148 0.01971 =
0.01744 -0.00385 -0.00385 0.01003
AFIX 137
H18D 2 0.232895 0.476046 1.076372 11.00000 -1.50000
H18E 2 0.288419 0.484163 1.008159 11.00000 -1.50000
H18F 2 0.243221 0.423613 1.062081 11.00000 -1.50000
AFIX 0
C19B 1 0.222226 0.495719 0.838219 11.00000 0.02563 0.01792 =
0.01776 -0.00086 -0.00244 0.01344
AFIX 137
H19D 2 0.196412 0.484570 0.767622 11.00000 -1.50000
H19E 2 0.261145 0.519860 0.809677 11.00000 -1.50000
H19F 2 0.212575 0.516560 0.897776 11.00000 -1.50000
AFIX 0
PART 1
C1 1 0.333333 0.666667 -0.051027 10.23333 0.02232 0.02232 =
0.02497 0.00000 0.00000 0.01116
CL1 5 0.266025 0.649729 0.000053 10.70000 0.01449 0.03417 =
0.03828 0.00573 0.00453 0.01277
CL2 5 0.333333 0.666667 -0.216171 10.23333 0.04421 0.04421 =
0.01915 0.00000 0.00000 0.02211
PART 2
C2 1 0.333333 0.666667 -0.347402 10.10000 0.01901 0.01901 =
0.09083 0.00000 0.00000 0.00951
CL3 5 0.333333 0.666667 -0.183061 10.10000 0.04421 0.04421 =
0.01915 0.00000 0.00000 0.02211
CL4 5 0.400205 0.682925 -0.385200 10.30000 0.01377 0.04347 =
0.08089 0.01297 0.00473 0.01533
PART 0
O1 3 0.333333 0.666667 0.182555 10.08333 0.01677 0.01677 =
0.01306 0.00000 0.00000 0.00839
O2 3 0.333333 0.666667 -0.575839 10.08333 0.02116 0.02116 =
0.01478 0.00000 0.00000 0.01058
HKLF 4
REM p11140 in R3
REM R1 = 0.0323 for 5976 Fo > 4sig(Fo) and 0.0332 for all 6061 data
REM 410 parameters refined using 5 restraints
END
WGHT 0.0637 4.4276
REM Highest difference peak 0.523, deepest hole -0.721, 1-sigma level 0.050
Q1 1 0.2804 0.6782 0.0228 11.00000 0.05 0.52
Q2 1 0.3542 0.6221 -0.0611 11.00000 0.05 0.47
Q3 1 0.2692 0.6115 -0.4193 11.00000 0.05 0.44
Q4 1 0.3333 0.6667 0.0314 10.33333 0.05 0.38
Q5 1 0.3333 0.6667 -0.4293 10.33333 0.05 0.38
Q6 1 0.3181 0.7120 -0.3257 11.00000 0.05 0.31
Q7 1 0.0901 0.5263 -0.2512 11.00000 0.05 0.27
Q8 1 0.1365 0.5836 -0.2624 11.00000 0.05 0.26
Q9 1 0.2755 0.5025 0.4408 11.00000 0.05 0.25
;
#==============================================================================
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common
;
S-Thiadianin's, R-Dianin's CCl4,H2O Quasiracemate
;
_chemical_melting_point ?
_chemical_compound_source ?
_chemical_absolute_configuration ad
_chemical_formula_iupac ?
_chemical_formula_moiety
'3(C18 H20 O S),3(C18 H20 O2), (C Cl4), 0.5(H2 O)'
_chemical_formula_sum 'C109 H121 Cl4 O9.50 S3'
_chemical_formula_weight 1821.04
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_space_group_id
1
_space_group_crystal_system Trigonal
_space_group_IT_number 146
_space_group_name_H-M_alt 'R 3'
_space_group_name_Hall 'R 3'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
_cell_length_a 27.3283(4)
_cell_length_b 27.3283(4)
_cell_length_c 10.8327(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 120.00
_cell_volume 7006.4(2)
_cell_formula_units_Z 3
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 9616
_cell_measurement_theta_min 3.2315
_cell_measurement_theta_max 75.8600
_exptl_crystal_description Block
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.15
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.295
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2901
_exptl_absorpt_coefficient_mu 2.254
_exptl_absorpt_correction_T_min 0.72531
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(1)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5598
_diffrn_measurement_method '\w scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13784
_diffrn_reflns_av_R_equivalents 0.0201
_diffrn_reflns_av_sigmaI/netI 0.0220
_diffrn_reflns_limit_h_min -26
_diffrn_reflns_limit_h_max 31
_diffrn_reflns_limit_k_min -34
_diffrn_reflns_limit_k_max 34
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 9.01
_diffrn_reflns_theta_max 74.39
_reflns_number_total 6061
_reflns_number_gt 5976
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution 'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.032(9)
_refine_ls_number_reflns 6061
_refine_ls_number_parameters 410
_refine_ls_number_restraints 5
_refine_ls_R_factor_all 0.0332
_refine_ls_R_factor_gt 0.0323
_refine_ls_wR_factor_ref 0.1037
_refine_ls_wR_factor_gt 0.0980
_refine_ls_goodness_of_fit_ref 1.001
_refine_ls_restrained_S_all 1.002
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.066609(15) 0.583985(15) -0.35401(4) 0.01630(11) Uani 1 1 d . . .
O2A O 0.21106(6) 0.60524(5) 0.28319(11) 0.0199(3) Uani 1 1 d . . .
H2AA H 0.2294(13) 0.5885(12) 0.290(3) 0.033(7) Uiso 1 1 d . . .
C2A C 0.10898(7) 0.55449(7) -0.29481(14) 0.0148(3) Uani 1 1 d . . .
C3A C 0.07026(7) 0.50235(7) -0.21750(14) 0.0150(3) Uani 1 1 d . . .
H3AA H 0.0923 0.4841 -0.1935 0.018 Uiso 1 1 calc R . .
H3AB H 0.0393 0.4755 -0.2718 0.018 Uiso 1 1 calc R . .
C4A C 0.04306(7) 0.50979(7) -0.09895(14) 0.0141(3) Uani 1 1 d . . .
C5A C 0.01492(7) 0.54563(7) -0.12222(15) 0.0154(3) Uani 1 1 d . . .
C6A C -0.02306(7) 0.54471(7) -0.03400(15) 0.0169(3) Uani 1 1 d . . .
H6AA H -0.0309 0.5216 0.0370 0.020 Uiso 1 1 calc R . .
C7A C -0.04975(7) 0.57657(8) -0.04688(16) 0.0199(3) Uani 1 1 d . . .
H7AA H -0.0749 0.5754 0.0150 0.024 Uiso 1 1 calc R . .
C8A C -0.03917(7) 0.61006(7) -0.15095(17) 0.0202(3) Uani 1 1 d . . .
H8AA H -0.0572 0.6319 -0.1609 0.024 Uiso 1 1 calc R . .
C9A C -0.00245(7) 0.61148(7) -0.23959(16) 0.0184(3) Uani 1 1 d . . .
H9AA H 0.0046 0.6343 -0.3109 0.022 Uiso 1 1 calc R . .
C10A C 0.02478(7) 0.57963(7) -0.22622(15) 0.0157(3) Uani 1 1 d . . .
C11A C 0.08670(7) 0.53521(7) 0.00690(14) 0.0138(3) Uani 1 1 d . . .
C12A C 0.11446(7) 0.50664(7) 0.04805(15) 0.0155(3) Uani 1 1 d . . .
H12A H 0.1051 0.4714 0.0118 0.019 Uiso 1 1 calc R . .
C13A C 0.15509(7) 0.52844(7) 0.14000(15) 0.0173(3) Uani 1 1 d . . .
H13A H 0.1731 0.5082 0.1661 0.021 Uiso 1 1 calc R . .
C14A C 0.16954(7) 0.58049(7) 0.19444(14) 0.0158(3) Uani 1 1 d . . .
C15A C 0.14207(7) 0.60893(7) 0.15706(15) 0.0157(3) Uani 1 1 d . . .
H15A H 0.1510 0.6438 0.1947 0.019 Uiso 1 1 calc R . .
C16A C 0.10142(7) 0.58640(7) 0.06435(15) 0.0148(3) Uani 1 1 d . . .
H16A H 0.0831 0.6066 0.0394 0.018 Uiso 1 1 calc R . .
C17A C -0.00318(7) 0.44914(7) -0.06291(15) 0.0177(3) Uani 1 1 d . . .
H17A H -0.0186 0.4499 0.0183 0.027 Uiso 1 1 calc R . .
H17B H 0.0133 0.4245 -0.0597 0.027 Uiso 1 1 calc R . .
H17C H -0.0335 0.4346 -0.1245 0.027 Uiso 1 1 calc R . .
C18A C 0.12793(8) 0.53578(8) -0.40995(16) 0.0211(3) Uani 1 1 d . . .
H18A H 0.1541 0.5228 -0.3858 0.032 Uiso 1 1 calc R . .
H18B H 0.1469 0.5677 -0.4670 0.032 Uiso 1 1 calc R . .
H18C H 0.0949 0.5049 -0.4506 0.032 Uiso 1 1 calc R . .
C19A C 0.16059(7) 0.60016(7) -0.22602(15) 0.0175(3) Uani 1 1 d . . .
H19A H 0.1821 0.5836 -0.1908 0.026 Uiso 1 1 calc R . .
H19B H 0.1481 0.6158 -0.1596 0.026 Uiso 1 1 calc R . .
H19C H 0.1846 0.6304 -0.2836 0.026 Uiso 1 1 calc R . .
O1B O 0.15776(5) 0.40619(5) 0.93258(11) 0.0178(2) Uani 1 1 d . . .
O2B O 0.27309(6) 0.54895(5) 0.31402(11) 0.0206(3) Uani 1 1 d . . .
H2BA H 0.3075(15) 0.5619(14) 0.301(3) 0.039(7) Uiso 1 1 d . . .
C2B C 0.21684(7) 0.44297(7) 0.89993(15) 0.0150(3) Uani 1 1 d . . .
C3B C 0.23698(7) 0.41028(7) 0.82060(14) 0.0140(3) Uani 1 1 d . . .
H3BA H 0.2359 0.3796 0.8712 0.017 Uiso 1 1 calc R . .
H3BB H 0.2768 0.4361 0.7972 0.017 Uiso 1 1 calc R . .
C4B C 0.20238(7) 0.38409(6) 0.70179(14) 0.0134(3) Uani 1 1 d . . .
C5B C 0.14005(7) 0.35731(7) 0.73412(14) 0.0134(3) Uani 1 1 d . . .
C6B C 0.09837(7) 0.31737(7) 0.65586(15) 0.0173(3) Uani 1 1 d . . .
H6BA H 0.1096 0.3070 0.5818 0.021 Uiso 1 1 calc R . .
C7B C 0.04112(7) 0.29238(7) 0.68335(17) 0.0192(3) Uani 1 1 d . . .
H7BA H 0.0137 0.2656 0.6284 0.023 Uiso 1 1 calc R . .
C8B C 0.02450(7) 0.30691(7) 0.79168(17) 0.0202(3) Uani 1 1 d . . .
H8BA H -0.0145 0.2906 0.8106 0.024 Uiso 1 1 calc R . .
C9B C 0.06461(7) 0.34513(7) 0.87217(16) 0.0178(3) Uani 1 1 d . . .
H9BA H 0.0531 0.3543 0.9473 0.021 Uiso 1 1 calc R . .
C10B C 0.12204(7) 0.37042(7) 0.84349(15) 0.0151(3) Uani 1 1 d . . .
C11B C 0.21979(7) 0.42784(6) 0.59761(14) 0.0137(3) Uani 1 1 d . . .
C12B C 0.27651(7) 0.45784(7) 0.56059(15) 0.0158(3) Uani 1 1 d . . .
H12B H 0.3031 0.4506 0.6011 0.019 Uiso 1 1 calc R . .
C13B C 0.29515(7) 0.49782(7) 0.46643(15) 0.0179(3) Uani 1 1 d . . .
H13B H 0.3339 0.5174 0.4433 0.021 Uiso 1 1 calc R . .
C14B C 0.25679(7) 0.50884(7) 0.40655(14) 0.0155(3) Uani 1 1 d . . .
C15B C 0.20020(7) 0.47945(7) 0.43927(14) 0.0156(3) Uani 1 1 d . . .
H15B H 0.1737 0.4865 0.3975 0.019 Uiso 1 1 calc R . .
C16B C 0.18225(6) 0.43940(7) 0.53418(15) 0.0149(3) Uani 1 1 d . . .
H16B H 0.1434 0.4195 0.5561 0.018 Uiso 1 1 calc R . .
C17B C 0.21606(7) 0.33818(7) 0.65990(15) 0.0177(3) Uani 1 1 d . . .
H17D H 0.1980 0.3228 0.5801 0.027 Uiso 1 1 calc R . .
H17E H 0.2018 0.3078 0.7213 0.027 Uiso 1 1 calc R . .
H17F H 0.2571 0.3549 0.6517 0.027 Uiso 1 1 calc R . .
C18B C 0.24812(8) 0.45804(7) 1.02253(16) 0.0197(3) Uani 1 1 d . . .
H18D H 0.2329 0.4760 1.0764 0.029 Uiso 1 1 calc R . .
H18E H 0.2884 0.4842 1.0082 0.029 Uiso 1 1 calc R . .
H18F H 0.2432 0.4236 1.0621 0.029 Uiso 1 1 calc R . .
C19B C 0.22223(8) 0.49572(7) 0.83822(15) 0.0193(3) Uani 1 1 d . . .
H19D H 0.1964 0.4846 0.7676 0.029 Uiso 1 1 calc R . .
H19E H 0.2611 0.5199 0.8097 0.029 Uiso 1 1 calc R . .
H19F H 0.2126 0.5166 0.8978 0.029 Uiso 1 1 calc R . .
C1 C 0.3333 0.6667 -0.0510(4) 0.0232(8) Uani 0.70 3 d SPD . 1
Cl1 Cl 0.26602(3) 0.64973(3) 0.00005(7) 0.02871(15) Uani 0.70 1 d PD A 1
Cl2 Cl 0.3333 0.6667 -0.21617(12) 0.0359(4) Uani 0.70 3 d SPD B 1
C2 C 0.3333 0.6667 -0.3474(13) 0.043(4) Uani 0.30 3 d SPD . 2
Cl3 Cl 0.3333 0.6667 -0.1831(5) 0.0359(4) Uani 0.30 3 d SPD C 2
Cl4 Cl 0.40020(7) 0.68292(9) -0.3852(2) 0.0456(5) Uani 0.30 1 d PD D 2
O1 O 0.3333 0.6667 0.1826(7) 0.0155(14) Uani 0.25 3 d SP . .
O2 O 0.3333 0.6667 -0.5758(7) 0.0190(16) Uani 0.25 3 d SP . .
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
S1A 0.01494(18) 0.01812(19) 0.01572(18) 0.00467(13) 0.00148(13) 0.00818(15)
O2A 0.0230(6) 0.0198(6) 0.0198(6) -0.0040(5) -0.0069(5) 0.0128(5)
C2A 0.0156(7) 0.0150(7) 0.0148(7) 0.0003(6) 0.0017(6) 0.0083(6)
C3A 0.0173(7) 0.0122(7) 0.0147(7) -0.0006(5) 0.0005(6) 0.0067(6)
C4A 0.0145(7) 0.0136(7) 0.0141(7) -0.0005(5) 0.0009(6) 0.0070(6)
C5A 0.0139(7) 0.0143(7) 0.0168(7) -0.0027(6) -0.0030(6) 0.0061(6)
C6A 0.0159(7) 0.0197(7) 0.0170(7) -0.0007(6) -0.0010(6) 0.0103(6)
C7A 0.0161(7) 0.0254(8) 0.0212(8) -0.0076(7) -0.0030(6) 0.0126(7)
C8A 0.0191(8) 0.0211(8) 0.0259(8) -0.0058(6) -0.0065(6) 0.0142(7)
C9A 0.0189(8) 0.0149(7) 0.0219(8) -0.0002(6) -0.0040(6) 0.0089(6)
C10A 0.0122(7) 0.0134(7) 0.0191(8) -0.0022(6) -0.0006(5) 0.0045(6)
C11A 0.0166(7) 0.0146(7) 0.0110(7) 0.0006(5) 0.0010(6) 0.0083(6)
C12A 0.0172(7) 0.0140(7) 0.0162(7) 0.0004(6) 0.0015(6) 0.0085(6)
C13A 0.0188(7) 0.0192(8) 0.0172(7) 0.0023(6) 0.0009(6) 0.0120(6)
C14A 0.0155(7) 0.0187(7) 0.0128(7) -0.0005(6) -0.0001(6) 0.0083(6)
C15A 0.0185(7) 0.0135(7) 0.0161(7) -0.0011(5) 0.0007(6) 0.0087(6)
C16A 0.0164(7) 0.0154(7) 0.0144(7) 0.0008(6) 0.0008(5) 0.0094(6)
C17A 0.0158(7) 0.0157(7) 0.0189(8) 0.0029(6) 0.0008(6) 0.0057(6)
C18A 0.0231(8) 0.0231(8) 0.0178(7) -0.0002(6) 0.0049(6) 0.0121(7)
C19A 0.0145(7) 0.0166(7) 0.0188(7) 0.0004(6) 0.0011(6) 0.0060(6)
O1B 0.0156(6) 0.0190(6) 0.0166(6) -0.0036(4) 0.0017(4) 0.0070(5)
O2B 0.0176(6) 0.0243(6) 0.0207(6) 0.0079(5) 0.0041(4) 0.0112(5)
C2B 0.0153(7) 0.0150(7) 0.0150(7) -0.0010(6) -0.0006(6) 0.0079(6)
C3B 0.0138(7) 0.0152(7) 0.0140(7) 0.0002(5) -0.0009(6) 0.0081(6)
C4B 0.0149(7) 0.0134(7) 0.0124(7) -0.0020(5) -0.0022(5) 0.0075(6)
C5B 0.0147(7) 0.0115(7) 0.0142(7) 0.0019(5) 0.0002(6) 0.0068(6)
C6B 0.0178(8) 0.0170(7) 0.0173(7) 0.0027(6) 0.0013(6) 0.0088(6)
C7B 0.0153(7) 0.0166(7) 0.0211(8) 0.0017(6) -0.0043(6) 0.0045(6)
C8B 0.0135(7) 0.0193(8) 0.0271(9) 0.0076(7) 0.0030(6) 0.0077(6)
C9B 0.0159(7) 0.0167(8) 0.0213(7) 0.0024(6) 0.0019(6) 0.0086(6)
C10B 0.0173(7) 0.0125(7) 0.0169(7) 0.0020(5) -0.0003(6) 0.0085(6)
C11B 0.0157(8) 0.0129(7) 0.0125(7) -0.0020(5) -0.0003(5) 0.0072(6)
C12B 0.0133(7) 0.0195(7) 0.0157(7) -0.0001(6) -0.0011(6) 0.0091(6)
C13B 0.0131(7) 0.0211(8) 0.0180(7) 0.0006(6) 0.0010(6) 0.0076(6)
C14B 0.0168(7) 0.0164(7) 0.0137(7) 0.0009(6) 0.0006(6) 0.0087(6)
C15B 0.0152(7) 0.0178(7) 0.0151(7) -0.0017(6) -0.0021(5) 0.0092(6)
C16B 0.0113(7) 0.0157(7) 0.0166(7) -0.0035(6) -0.0010(5) 0.0060(6)
C17B 0.0215(8) 0.0185(7) 0.0171(7) -0.0011(6) 0.0006(6) 0.0129(6)
C18B 0.0215(8) 0.0197(8) 0.0174(8) -0.0038(6) -0.0039(6) 0.0100(6)
C19B 0.0256(8) 0.0179(8) 0.0178(7) -0.0009(6) -0.0024(6) 0.0134(7)
C1 0.0223(13) 0.0223(13) 0.025(2) 0.000 0.000 0.0112(6)
Cl1 0.0145(3) 0.0342(3) 0.0383(3) 0.0057(3) 0.0045(2) 0.0128(2)
Cl2 0.0442(3) 0.0442(3) 0.0192(11) 0.000 0.000 0.02211(15)
C2 0.019(3) 0.019(3) 0.091(11) 0.000 0.000 0.0095(17)
Cl3 0.0442(3) 0.0442(3) 0.0192(11) 0.000 0.000 0.02211(15)
Cl4 0.0138(7) 0.0435(10) 0.0809(15) 0.0130(9) 0.0047(7) 0.0153(7)
O1 0.017(2) 0.017(2) 0.013(3) 0.000 0.000 0.0084(11)
O2 0.021(2) 0.021(2) 0.015(4) 0.000 0.000 0.0106(12)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1A C10A 1.7611(17) . ?
S1A C2A 1.8262(17) . ?
O2A C14A 1.379(2) . ?
C2A C19A 1.530(2) . ?
C2A C3A 1.531(2) . ?
C2A C18A 1.533(2) . ?
C3A C4A 1.547(2) . ?
C4A C5A 1.539(2) . ?
C4A C11A 1.546(2) . ?
C4A C17A 1.550(2) . ?
C5A C10A 1.398(2) . ?
C5A C6A 1.402(2) . ?
C6A C7A 1.394(2) . ?
C7A C8A 1.388(3) . ?
C8A C9A 1.375(3) . ?
C9A C10A 1.407(2) . ?
C11A C16A 1.394(2) . ?
C11A C12A 1.406(2) . ?
C12A C13A 1.385(2) . ?
C13A C14A 1.402(2) . ?
C14A C15A 1.384(2) . ?
C15A C16A 1.392(2) . ?
O1B C10B 1.373(2) . ?
O1B C2B 1.456(2) . ?
O2B C14B 1.3844(19) . ?
C2B C18B 1.521(2) . ?
C2B C3B 1.527(2) . ?
C2B C19B 1.528(2) . ?
C3B C4B 1.545(2) . ?
C4B C5B 1.521(2) . ?
C4B C11B 1.536(2) . ?
C4B C17B 1.546(2) . ?
C5B C10B 1.397(2) . ?
C5B C6B 1.402(2) . ?
C6B C7B 1.391(2) . ?
C7B C8B 1.386(3) . ?
C8B C9B 1.381(3) . ?
C9B C10B 1.397(2) . ?
C11B C16B 1.396(2) . ?
C11B C12B 1.402(2) . ?
C12B C13B 1.392(2) . ?
C13B C14B 1.388(2) . ?
C14B C15B 1.386(2) . ?
C15B C16B 1.400(2) . ?
C1 Cl1 1.7471(16) . ?
C1 Cl1 1.7471(16) 3_565 ?
C1 Cl1 1.7472(16) 2_665 ?
C1 Cl2 1.789(5) . ?
C2 Cl4 1.701(4) 2_665 ?
C2 Cl4 1.701(4) 3_565 ?
C2 Cl4 1.701(4) . ?
C2 Cl3 1.780(14) . ?
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
C10A S1A C2A 103.15(7) . . ?
C19A C2A C3A 114.77(13) . . ?
C19A C2A C18A 109.92(13) . . ?
C3A C2A C18A 109.04(13) . . ?
C19A C2A S1A 109.89(11) . . ?
C3A C2A S1A 107.89(11) . . ?
C18A C2A S1A 104.83(11) . . ?
C2A C3A C4A 119.06(13) . . ?
C5A C4A C11A 110.74(13) . . ?
C5A C4A C3A 111.93(13) . . ?
C11A C4A C3A 111.18(12) . . ?
C5A C4A C17A 108.81(12) . . ?
C11A C4A C17A 109.09(12) . . ?
C3A C4A C17A 104.89(12) . . ?
C10A C5A C6A 117.13(15) . . ?
C10A C5A C4A 124.30(14) . . ?
C6A C5A C4A 118.57(14) . . ?
C7A C6A C5A 122.30(16) . . ?
C8A C7A C6A 119.43(16) . . ?
C9A C8A C7A 119.59(15) . . ?
C8A C9A C10A 120.98(16) . . ?
C5A C10A C9A 120.55(15) . . ?
C5A C10A S1A 125.54(12) . . ?
C9A C10A S1A 113.79(13) . . ?
C16A C11A C12A 116.78(15) . . ?
C16A C11A C4A 123.56(14) . . ?
C12A C11A C4A 119.65(14) . . ?
C13A C12A C11A 121.90(15) . . ?
C12A C13A C14A 119.83(15) . . ?
O2A C14A C15A 118.23(15) . . ?
O2A C14A C13A 122.41(15) . . ?
C15A C14A C13A 119.35(15) . . ?
C14A C15A C16A 119.98(15) . . ?
C15A C16A C11A 122.15(15) . . ?
C10B O1B C2B 117.97(13) . . ?
O1B C2B C18B 104.72(13) . . ?
O1B C2B C3B 109.42(12) . . ?
C18B C2B C3B 109.38(13) . . ?
O1B C2B C19B 107.95(13) . . ?
C18B C2B C19B 110.53(13) . . ?
C3B C2B C19B 114.38(14) . . ?
C2B C3B C4B 115.08(12) . . ?
C5B C4B C11B 112.34(12) . . ?
C5B C4B C3B 108.05(12) . . ?
C11B C4B C3B 111.83(12) . . ?
C5B C4B C17B 110.14(12) . . ?
C11B C4B C17B 108.04(12) . . ?
C3B C4B C17B 106.27(12) . . ?
C10B C5B C6B 117.36(14) . . ?
C10B C5B C4B 121.70(14) . . ?
C6B C5B C4B 120.93(14) . . ?
C7B C6B C5B 121.97(15) . . ?
C8B C7B C6B 119.34(16) . . ?
C9B C8B C7B 120.08(15) . . ?
C8B C9B C10B 120.27(16) . . ?
O1B C10B C5B 124.23(14) . . ?
O1B C10B C9B 114.76(15) . . ?
C5B C10B C9B 120.96(15) . . ?
C16B C11B C12B 116.73(14) . . ?
C16B C11B C4B 124.13(14) . . ?
C12B C11B C4B 119.13(14) . . ?
C13B C12B C11B 122.17(15) . . ?
C14B C13B C12B 119.55(15) . . ?
O2B C14B C15B 117.91(14) . . ?
O2B C14B C13B 122.09(15) . . ?
C15B C14B C13B 120.00(15) . . ?
C14B C15B C16B 119.61(15) . . ?
C11B C16B C15B 121.93(14) . . ?
Cl1 C1 Cl1 110.46(14) . 3_565 ?
Cl1 C1 Cl1 110.46(14) . 2_665 ?
Cl1 C1 Cl1 110.46(14) 3_565 2_665 ?
Cl1 C1 Cl2 108.46(14) . . ?
Cl1 C1 Cl2 108.46(14) 3_565 . ?
Cl1 C1 Cl2 108.46(14) 2_665 . ?
Cl4 C2 Cl4 114.4(4) 2_665 3_565 ?
Cl4 C2 Cl4 114.4(4) 2_665 . ?
Cl4 C2 Cl4 114.4(4) 3_565 . ?
Cl4 C2 Cl3 103.9(5) 2_665 . ?
Cl4 C2 Cl3 103.9(5) 3_565 . ?
Cl4 C2 Cl3 103.9(5) . . ?
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
C10A S1A C2A C19A -83.57(12) . . . . ?
C10A S1A C2A C3A 42.24(12) . . . . ?
C10A S1A C2A C18A 158.35(11) . . . . ?
C19A C2A C3A C4A 59.13(19) . . . . ?
C18A C2A C3A C4A -177.08(14) . . . . ?
S1A C2A C3A C4A -63.74(16) . . . . ?
C2A C3A C4A C5A 49.12(18) . . . . ?
C2A C3A C4A C11A -75.30(17) . . . . ?
C2A C3A C4A C17A 166.94(14) . . . . ?
C11A C4A C5A C10A 108.91(17) . . . . ?
C3A C4A C5A C10A -15.8(2) . . . . ?
C17A C4A C5A C10A -131.20(16) . . . . ?
C11A C4A C5A C6A -70.89(18) . . . . ?
C3A C4A C5A C6A 164.44(14) . . . . ?
C17A C4A C5A C6A 48.99(18) . . . . ?
C10A C5A C6A C7A -0.8(2) . . . . ?
C4A C5A C6A C7A 178.99(15) . . . . ?
C5A C6A C7A C8A 0.7(3) . . . . ?
C6A C7A C8A C9A -0.2(3) . . . . ?
C7A C8A C9A C10A -0.2(3) . . . . ?
C6A C5A C10A C9A 0.4(2) . . . . ?
C4A C5A C10A C9A -179.44(15) . . . . ?
C6A C5A C10A S1A -175.34(12) . . . . ?
C4A C5A C10A S1A 4.9(2) . . . . ?
C8A C9A C10A C5A 0.2(2) . . . . ?
C8A C9A C10A S1A 176.34(13) . . . . ?
C2A S1A C10A C5A -17.78(16) . . . . ?
C2A S1A C10A C9A 166.26(12) . . . . ?
C5A C4A C11A C16A -5.3(2) . . . . ?
C3A C4A C11A C16A 119.79(16) . . . . ?
C17A C4A C11A C16A -125.02(16) . . . . ?
C5A C4A C11A C12A 175.84(14) . . . . ?
C3A C4A C11A C12A -59.07(18) . . . . ?
C17A C4A C11A C12A 56.12(18) . . . . ?
C16A C11A C12A C13A -0.9(2) . . . . ?
C4A C11A C12A C13A 178.05(14) . . . . ?
C11A C12A C13A C14A -0.1(2) . . . . ?
C12A C13A C14A O2A -177.63(15) . . . . ?
C12A C13A C14A C15A 1.3(2) . . . . ?
O2A C14A C15A C16A 177.55(14) . . . . ?
C13A C14A C15A C16A -1.4(2) . . . . ?
C14A C15A C16A C11A 0.4(2) . . . . ?
C12A C11A C16A C15A 0.8(2) . . . . ?
C4A C11A C16A C15A -178.13(14) . . . . ?
C10B O1B C2B C18B -157.79(13) . . . . ?
C10B O1B C2B C3B -40.64(18) . . . . ?
C10B O1B C2B C19B 84.42(16) . . . . ?
O1B C2B C3B C4B 56.69(17) . . . . ?
C18B C2B C3B C4B 170.87(13) . . . . ?
C19B C2B C3B C4B -64.55(18) . . . . ?
C2B C3B C4B C5B -43.56(17) . . . . ?
C2B C3B C4B C11B 80.59(16) . . . . ?
C2B C3B C4B C17B -161.74(13) . . . . ?
C11B C4B C5B C10B -107.41(16) . . . . ?
C3B C4B C5B C10B 16.43(19) . . . . ?
C17B C4B C5B C10B 132.12(15) . . . . ?
C11B C4B C5B C6B 73.99(18) . . . . ?
C3B C4B C5B C6B -162.17(14) . . . . ?
C17B C4B C5B C6B -46.49(19) . . . . ?
C10B C5B C6B C7B 1.5(2) . . . . ?
C4B C5B C6B C7B -179.88(14) . . . . ?
C5B C6B C7B C8B -0.5(2) . . . . ?
C6B C7B C8B C9B -1.1(3) . . . . ?
C7B C8B C9B C10B 1.6(3) . . . . ?
C2B O1B C10B C5B 15.3(2) . . . . ?
C2B O1B C10B C9B -167.41(14) . . . . ?
C6B C5B C10B O1B 176.18(15) . . . . ?
C4B C5B C10B O1B -2.5(2) . . . . ?
C6B C5B C10B C9B -0.9(2) . . . . ?
C4B C5B C10B C9B -179.56(15) . . . . ?
C8B C9B C10B O1B -177.95(14) . . . . ?
C8B C9B C10B C5B -0.6(2) . . . . ?
C5B C4B C11B C16B -3.7(2) . . . . ?
C3B C4B C11B C16B -125.44(16) . . . . ?
C17B C4B C11B C16B 117.95(17) . . . . ?
C5B C4B C11B C12B 177.54(14) . . . . ?
C3B C4B C11B C12B 55.83(18) . . . . ?
C17B C4B C11B C12B -60.77(17) . . . . ?
C16B C11B C12B C13B 0.8(2) . . . . ?
C4B C11B C12B C13B 179.62(14) . . . . ?
C11B C12B C13B C14B 0.1(3) . . . . ?
C12B C13B C14B O2B 178.65(15) . . . . ?
C12B C13B C14B C15B -1.0(2) . . . . ?
O2B C14B C15B C16B -178.67(14) . . . . ?
C13B C14B C15B C16B 1.0(2) . . . . ?
C12B C11B C16B C15B -0.8(2) . . . . ?
C4B C11B C16B C15B -179.57(14) . . . . ?
C14B C15B C16B C11B -0.1(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2A H2AA O2B 0.83(3) 1.99(3) 2.8212(19) 178(3) .
O2B H2BA O2A 0.84(3) 2.07(4) 2.9010(19) 170(3) 2_665
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 74.39
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.523
_refine_diff_density_min -0.721
_refine_diff_density_rms 0.050
_database_code_depnum_ccdc_archive 'CCDC 933473'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_p12001_test-sr
#==============================================================================
_iucr_refine_instructions_details
;
TITL p12001_1n in R3
CELL 1.54178 27.2258 27.2258 10.8365 90.000 90.000 120.000
ZERR 9.00 0.0004 0.0004 0.0002 0.000 0.000 0.000
LATT -3
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SFAC C H O S
UNIT 324 363 27 9
SIZE 0.25 0.07 0.05
SHEL 5.00 0.80
TEMP -183
L.S. 12
CONF
ACTA
EQIV$1 1.00-Y, 1.00+x-y, 0.00+Z
HTAB O2A O2B
HTAB O2B O2A_$1
RTAB DIST C17A C18A
RTAB DIST C17B C18B
MPLA 6 C5A C6A C7A C8A C9A C10A S1A C4A
MPLA 5 C4A C5A C10A S1A C3A C2A
MPLA 6 C11A C12A C13A C14A C15A C16A C4A O2A
MPLA 6 C5B C6B C7B C8B C9B C10B O1B C4B
MPLA 5 C4B C5B C10B O1B C3B C2B
MPLA 6 C11B C12B C13B C14B C15B C16B C4B O2B
WPDB -1
FMAP 2
PLAN -9
WGHT 0.050000 0.450000
FVAR 0.99923
S1A 4 0.067552 0.583464 -0.354215 11.00000 0.01718 0.01948 =
0.01682 0.00436 0.00118 0.00892
O2A 3 0.214187 0.607640 0.279856 11.00000 0.02287 0.02178 =
0.02020 -0.00429 -0.00657 0.01299
H2AA 2 0.233215 0.589638 0.291926 11.00000 0.04788
C2A 1 0.111005 0.555355 -0.292207 11.00000 0.01774 0.01718 =
0.01573 -0.00047 0.00053 0.00998
C3A 1 0.072273 0.502860 -0.216135 11.00000 0.01976 0.01456 =
0.01505 -0.00096 -0.00071 0.00862
AFIX 23
H3AA 2 0.094629 0.484890 -0.191287 11.00000 -1.20000
H3AB 2 0.041647 0.475783 -0.271201 11.00000 -1.20000
AFIX 0
C4A 1 0.044010 0.509807 -0.098480 11.00000 0.01564 0.01531 =
0.01309 0.00017 -0.00011 0.00730
C5A 1 0.015473 0.545281 -0.122318 11.00000 0.01442 0.01437 =
0.01748 -0.00328 -0.00421 0.00575
C6A 1 -0.022770 0.544345 -0.034724 11.00000 0.01778 0.02209 =
0.01699 -0.00112 -0.00200 0.00992
AFIX 43
H6AA 2 -0.030611 0.521226 0.036464 11.00000 -1.20000
AFIX 0
C7A 1 -0.049735 0.576023 -0.048045 11.00000 0.01759 0.02499 =
0.02192 -0.00603 -0.00383 0.01152
AFIX 43
H7AA 2 -0.075366 0.574548 0.013301 11.00000 -1.20000
AFIX 0
C8A 1 -0.038735 0.609961 -0.152408 11.00000 0.02062 0.02220 =
0.02814 -0.00660 -0.00768 0.01470
AFIX 43
H8AA 2 -0.056587 0.632060 -0.162449 11.00000 -1.20000
AFIX 0
C9A 1 -0.001961 0.611169 -0.240361 11.00000 0.02177 0.01501 =
0.02421 -0.00049 -0.00639 0.00921
AFIX 43
H9AA 2 0.005226 0.634029 -0.311760 11.00000 -1.20000
AFIX 0
C10A 1 0.025358 0.579159 -0.226845 11.00000 0.01268 0.01418 =
0.01860 -0.00363 -0.00270 0.00511
C11A 1 0.087610 0.535286 0.007438 11.00000 0.01607 0.01470 =
0.01371 0.00142 0.00226 0.00751
C12A 1 0.116001 0.507077 0.047982 11.00000 0.02012 0.01469 =
0.01622 -0.00003 0.00145 0.00921
AFIX 43
H12A 2 0.106549 0.471501 0.012558 11.00000 -1.20000
AFIX 0
C13A 1 0.157694 0.530064 0.138928 11.00000 0.02224 0.01959 =
0.01722 0.00195 0.00160 0.01370
AFIX 43
H13A 2 0.176446 0.510281 0.164497 11.00000 -1.20000
AFIX 0
C14A 1 0.171889 0.582009 0.192350 11.00000 0.01728 0.01932 =
0.01303 0.00013 -0.00054 0.00869
C15A 1 0.143321 0.609889 0.156343 11.00000 0.02104 0.01575 =
0.01599 -0.00100 0.00072 0.01042
AFIX 43
H15A 2 0.151892 0.644768 0.194153 11.00000 -1.20000
AFIX 0
C16A 1 0.102106 0.586682 0.064786 11.00000 0.01867 0.01734 =
0.01498 0.00115 0.00137 0.01031
AFIX 43
H16A 2 0.083188 0.606470 0.040466 11.00000 -1.20000
AFIX 0
C17A 1 -0.002151 0.448732 -0.062991 11.00000 0.01882 0.01513 =
0.02135 0.00202 0.00089 0.00613
AFIX 137
H17A 2 -0.018361 0.449310 0.017374 11.00000 -1.50000
H17B 2 0.014863 0.424451 -0.058303 11.00000 -1.50000
H17C 2 -0.032141 0.433819 -0.125606 11.00000 -1.50000
AFIX 0
C18A 1 0.131482 0.537580 -0.405738 11.00000 0.02797 0.02288 =
0.01883 0.00054 0.00480 0.01356
AFIX 137
H18A 2 0.158176 0.525254 -0.380346 11.00000 -1.50000
H18B 2 0.150462 0.569822 -0.462357 11.00000 -1.50000
H18C 2 0.098961 0.506249 -0.447425 11.00000 -1.50000
AFIX 0
C19A 1 0.161679 0.601971 -0.221894 11.00000 0.01613 0.01927 =
0.02023 0.00160 0.00127 0.00651
AFIX 137
H19A 2 0.183014 0.585897 -0.183037 11.00000 -1.50000
H19B 2 0.148069 0.617836 -0.158196 11.00000 -1.50000
H19C 2 0.186392 0.632019 -0.279439 11.00000 -1.50000
AFIX 0
O1B 3 0.158467 0.406662 0.932739 11.00000 0.01863 0.02221 =
0.01761 -0.00254 0.00196 0.00994
O2B 3 0.273345 0.549684 0.315155 11.00000 0.01778 0.02222 =
0.02083 0.00591 0.00365 0.00972
H2BA 2 0.303284 0.561679 0.302665 11.00000 0.03954
C2B 1 0.217645 0.443497 0.899068 11.00000 0.01647 0.01818 =
0.01599 -0.00025 -0.00013 0.00905
C3B 1 0.237643 0.410342 0.820284 11.00000 0.01499 0.01822 =
0.01552 0.00068 -0.00043 0.00877
AFIX 23
H3BA 2 0.236513 0.379640 0.871348 11.00000 -1.20000
H3BB 2 0.277667 0.436099 0.796741 11.00000 -1.20000
AFIX 0
C4B 1 0.202940 0.383836 0.701869 11.00000 0.01520 0.01662 =
0.01536 -0.00130 -0.00039 0.00925
C5B 1 0.140264 0.356906 0.734744 11.00000 0.01656 0.01555 =
0.01551 0.00162 -0.00042 0.00825
C6B 1 0.098349 0.316701 0.657001 11.00000 0.01998 0.01791 =
0.01826 0.00188 0.00066 0.00877
AFIX 43
H6BA 2 0.109487 0.306207 0.583045 11.00000 -1.20000
AFIX 0
C7B 1 0.040806 0.291616 0.684797 11.00000 0.01779 0.01735 =
0.02373 0.00294 -0.00422 0.00595
AFIX 43
H7BA 2 0.013126 0.264659 0.630279 11.00000 -1.20000
AFIX 0
C8B 1 0.024498 0.306626 0.793532 11.00000 0.01641 0.02043 =
0.02912 0.00792 0.00289 0.00935
AFIX 43
H8BA 2 -0.014621 0.290272 0.812914 11.00000 -1.20000
AFIX 0
C9B 1 0.064822 0.345129 0.873365 11.00000 0.01818 0.02037 =
0.02347 0.00423 0.00461 0.01133
AFIX 43
H9BA 2 0.053299 0.354440 0.948350 11.00000 -1.20000
AFIX 0
C10B 1 0.122792 0.370696 0.844734 11.00000 0.01702 0.01597 =
0.01764 0.00223 0.00183 0.00922
C11B 1 0.220239 0.427849 0.596869 11.00000 0.01747 0.01620 =
0.01279 -0.00297 -0.00072 0.00830
C12B 1 0.276917 0.458006 0.560207 11.00000 0.01529 0.02252 =
0.01800 0.00017 -0.00147 0.01139
AFIX 43
H12B 2 0.303584 0.450659 0.600447 11.00000 -1.20000
AFIX 0
C13B 1 0.295757 0.498424 0.466883 11.00000 0.01410 0.02037 =
0.01836 0.00013 0.00109 0.00729
AFIX 43
H13B 2 0.334682 0.518338 0.444268 11.00000 -1.20000
AFIX 0
C14B 1 0.257129 0.509466 0.406887 11.00000 0.01838 0.01525 =
0.01458 -0.00058 0.00093 0.00793
C15B 1 0.200322 0.479414 0.439807 11.00000 0.01730 0.02026 =
0.01475 -0.00145 -0.00168 0.01050
AFIX 43
H15B 2 0.173577 0.486103 0.397871 11.00000 -1.20000
AFIX 0
C16B 1 0.182409 0.439373 0.534428 11.00000 0.01250 0.01809 =
0.01767 -0.00294 -0.00049 0.00723
AFIX 43
H16B 2 0.143458 0.419479 0.556827 11.00000 -1.20000
AFIX 0
C17B 1 0.216455 0.337756 0.659514 11.00000 0.02282 0.02113 =
0.01696 -0.00067 0.00072 0.01259
AFIX 137
H17D 2 0.199101 0.323140 0.578705 11.00000 -1.50000
H17E 2 0.201208 0.306702 0.719620 11.00000 -1.50000
H17F 2 0.257639 0.354163 0.653322 11.00000 -1.50000
AFIX 0
C18B 1 0.249732 0.459770 1.020981 11.00000 0.02431 0.02562 =
0.01755 -0.00384 -0.00461 0.01444
AFIX 137
H18D 2 0.234444 0.477957 1.074464 11.00000 -1.50000
H18E 2 0.290032 0.486189 1.005431 11.00000 -1.50000
H18F 2 0.245376 0.425639 1.061526 11.00000 -1.50000
AFIX 0
C19B 1 0.222850 0.495997 0.836040 11.00000 0.02585 0.02176 =
0.01935 -0.00018 -0.00043 0.01482
AFIX 137
H19D 2 0.196223 0.484370 0.766728 11.00000 -1.50000
H19E 2 0.261648 0.519717 0.805474 11.00000 -1.50000
H19F 2 0.214023 0.517632 0.895426 11.00000 -1.50000
HKLF 4
REM p12001_1n in R3
REM R1 = 0.0298 for 5982 Fo > 4sig(Fo) and 0.0319 for all 6250 data
REM 375 parameters refined using 1 restraints
END
WGHT 0.0438 0.5055
REM Highest difference peak 0.244, deepest hole -0.152, 1-sigma level 0.038
Q1 1 0.0937 0.5295 -0.2511 11.00000 0.05 0.24
Q2 1 0.1357 0.5782 -0.2527 11.00000 0.05 0.22
Q3 1 0.2252 0.4725 0.8660 11.00000 0.05 0.20
Q4 1 0.1260 0.5522 -0.3497 11.00000 0.05 0.20
Q5 1 0.1321 0.3623 0.7771 11.00000 0.05 0.20
Q6 1 0.0257 0.5650 -0.1650 11.00000 0.05 0.19
Q7 1 0.1984 0.4252 0.5478 11.00000 0.05 0.19
Q8 1 0.2234 0.4250 0.8580 11.00000 0.05 0.19
Q9 1 0.2189 0.3947 0.7599 11.00000 0.05 0.18
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common
;
S-Thiadianin's, R-Dianin's empty Quasiracemate
;
_chemical_melting_point ?
_chemical_compound_source ?
_chemical_absolute_configuration ad
_chemical_formula_iupac ?
_chemical_formula_moiety 'C18 H20 O S, C18 H20 O2'
_chemical_formula_sum 'C36 H40 O3 S'
_chemical_formula_weight 552.74
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_space_group_id
1
_space_group_crystal_system Trigonal
_space_group_IT_number 146
_space_group_name_H-M_alt 'R 3'
_space_group_name_Hall 'R 3'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
_cell_length_a 27.2258(4)
_cell_length_b 27.2258(4)
_cell_length_c 10.8365(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 120.00
_cell_volume 6956.34(19)
_cell_formula_units_Z 9
_cell_measurement_temperature 90(1)
_cell_measurement_reflns_used 9674
_cell_measurement_theta_min 3.2438
_cell_measurement_theta_max 76.0779
_exptl_crystal_description Block
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.187
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2664
_exptl_absorpt_coefficient_mu 1.183
_exptl_absorpt_correction_T_min 0.90365
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 90(1)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5598
_diffrn_measurement_method '\w scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 6250
_diffrn_reflns_av_R_equivalents 0.0000
_diffrn_reflns_av_sigmaI/netI 0.0369
_diffrn_reflns_limit_h_min -33
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 34
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 9.01
_diffrn_reflns_theta_max 74.31
_reflns_number_total 6250
_reflns_number_gt 5982
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution 'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.4500P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.002(10)
_refine_ls_number_reflns 6250
_refine_ls_number_parameters 375
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0319
_refine_ls_R_factor_gt 0.0298
_refine_ls_wR_factor_ref 0.0777
_refine_ls_wR_factor_gt 0.0761
_refine_ls_goodness_of_fit_ref 1.006
_refine_ls_restrained_S_all 1.006
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.067552(14) 0.583464(14) -0.35421(3) 0.01794(8) Uani 1 1 d . . .
O2A O 0.21419(5) 0.60764(5) 0.27986(9) 0.0208(2) Uani 1 1 d . . .
H2AA H 0.2332(13) 0.5896(13) 0.292(2) 0.048(7) Uiso 1 1 d . . .
C2A C 0.11100(6) 0.55536(6) -0.29221(12) 0.0163(3) Uani 1 1 d . . .
C3A C 0.07227(6) 0.50286(6) -0.21613(12) 0.0164(3) Uani 1 1 d . . .
H3AA H 0.0946 0.4849 -0.1913 0.020 Uiso 1 1 calc R . .
H3AB H 0.0416 0.4758 -0.2712 0.020 Uiso 1 1 calc R . .
C4A C 0.04401(6) 0.50981(6) -0.09848(12) 0.0149(3) Uani 1 1 d . . .
C5A C 0.01547(6) 0.54528(6) -0.12232(13) 0.0161(3) Uani 1 1 d . . .
C6A C -0.02277(6) 0.54434(6) -0.03472(14) 0.0190(3) Uani 1 1 d . . .
H6AA H -0.0306 0.5212 0.0365 0.023 Uiso 1 1 calc R . .
C7A C -0.04973(6) 0.57602(7) -0.04804(14) 0.0211(3) Uani 1 1 d . . .
H7AA H -0.0754 0.5745 0.0133 0.025 Uiso 1 1 calc R . .
C8A C -0.03874(7) 0.60996(7) -0.15241(14) 0.0219(3) Uani 1 1 d . . .
H8AA H -0.0566 0.6321 -0.1624 0.026 Uiso 1 1 calc R . .
C9A C -0.00196(7) 0.61117(6) -0.24036(14) 0.0203(3) Uani 1 1 d . . .
H9AA H 0.0052 0.6340 -0.3118 0.024 Uiso 1 1 calc R . .
C10A C 0.02536(6) 0.57916(6) -0.22684(13) 0.0159(3) Uani 1 1 d . . .
C11A C 0.08761(6) 0.53529(6) 0.00744(12) 0.0149(3) Uani 1 1 d . . .
C12A C 0.11600(6) 0.50708(6) 0.04798(13) 0.0168(3) Uani 1 1 d . . .
H12A H 0.1065 0.4715 0.0126 0.020 Uiso 1 1 calc R . .
C13A C 0.15769(6) 0.53006(6) 0.13893(13) 0.0182(3) Uani 1 1 d . . .
H13A H 0.1764 0.5103 0.1645 0.022 Uiso 1 1 calc R . .
C14A C 0.17189(6) 0.58201(6) 0.19235(12) 0.0167(3) Uani 1 1 d . . .
C15A C 0.14332(6) 0.60989(6) 0.15634(13) 0.0171(3) Uani 1 1 d . . .
H15A H 0.1519 0.6448 0.1942 0.020 Uiso 1 1 calc R . .
C16A C 0.10211(6) 0.58668(6) 0.06479(12) 0.0164(3) Uani 1 1 d . . .
H16A H 0.0832 0.6065 0.0405 0.020 Uiso 1 1 calc R . .
C17A C -0.00215(6) 0.44873(6) -0.06299(14) 0.0195(3) Uani 1 1 d . . .
H17A H -0.0184 0.4493 0.0174 0.029 Uiso 1 1 calc R . .
H17B H 0.0149 0.4245 -0.0583 0.029 Uiso 1 1 calc R . .
H17C H -0.0321 0.4338 -0.1256 0.029 Uiso 1 1 calc R . .
C18A C 0.13148(7) 0.53758(7) -0.40574(14) 0.0228(3) Uani 1 1 d . . .
H18A H 0.1582 0.5253 -0.3803 0.034 Uiso 1 1 calc R . .
H18B H 0.1505 0.5698 -0.4624 0.034 Uiso 1 1 calc R . .
H18C H 0.0990 0.5062 -0.4474 0.034 Uiso 1 1 calc R . .
C19A C 0.16168(6) 0.60197(6) -0.22189(13) 0.0196(3) Uani 1 1 d . . .
H19A H 0.1830 0.5859 -0.1830 0.029 Uiso 1 1 calc R . .
H19B H 0.1481 0.6178 -0.1582 0.029 Uiso 1 1 calc R . .
H19C H 0.1864 0.6320 -0.2794 0.029 Uiso 1 1 calc R . .
O1B O 0.15847(5) 0.40666(5) 0.93274(9) 0.0196(2) Uani 1 1 d . . .
O2B O 0.27335(5) 0.54968(5) 0.31515(10) 0.0204(2) Uani 1 1 d . . .
H2BA H 0.3033(14) 0.5617(12) 0.303(2) 0.040(7) Uiso 1 1 d . . .
C2B C 0.21764(6) 0.44350(6) 0.89907(13) 0.0167(3) Uani 1 1 d . . .
C3B C 0.23764(6) 0.41034(6) 0.82028(13) 0.0160(3) Uani 1 1 d . . .
H3BA H 0.2365 0.3796 0.8713 0.019 Uiso 1 1 calc R . .
H3BB H 0.2777 0.4361 0.7967 0.019 Uiso 1 1 calc R . .
C4B C 0.20294(6) 0.38384(6) 0.70187(13) 0.0152(3) Uani 1 1 d . . .
C5B C 0.14026(6) 0.35691(6) 0.73474(12) 0.0158(3) Uani 1 1 d . . .
C6B C 0.09835(6) 0.31670(6) 0.65700(13) 0.0190(3) Uani 1 1 d . . .
H6BA H 0.1095 0.3062 0.5830 0.023 Uiso 1 1 calc R . .
C7B C 0.04081(7) 0.29162(6) 0.68480(14) 0.0209(3) Uani 1 1 d . . .
H7BA H 0.0131 0.2647 0.6303 0.025 Uiso 1 1 calc R . .
C8B C 0.02450(6) 0.30663(7) 0.79353(15) 0.0219(3) Uani 1 1 d . . .
H8BA H -0.0146 0.2903 0.8129 0.026 Uiso 1 1 calc R . .
C9B C 0.06482(6) 0.34513(6) 0.87337(14) 0.0199(3) Uani 1 1 d . . .
H9BA H 0.0533 0.3544 0.9484 0.024 Uiso 1 1 calc R . .
C10B C 0.12279(6) 0.37070(6) 0.84473(13) 0.0164(3) Uani 1 1 d . . .
C11B C 0.22024(6) 0.42785(6) 0.59687(12) 0.0155(3) Uani 1 1 d . . .
C12B C 0.27692(6) 0.45801(6) 0.56021(13) 0.0177(3) Uani 1 1 d . . .
H12B H 0.3036 0.4507 0.6004 0.021 Uiso 1 1 calc R . .
C13B C 0.29576(6) 0.49842(6) 0.46688(13) 0.0182(3) Uani 1 1 d . . .
H13B H 0.3347 0.5183 0.4443 0.022 Uiso 1 1 calc R . .
C14B C 0.25713(6) 0.50947(6) 0.40689(12) 0.0163(3) Uani 1 1 d . . .
C15B C 0.20032(6) 0.47941(6) 0.43981(12) 0.0169(3) Uani 1 1 d . . .
H15B H 0.1736 0.4861 0.3979 0.020 Uiso 1 1 calc R . .
C16B C 0.18241(6) 0.43937(6) 0.53443(13) 0.0163(3) Uani 1 1 d . . .
H16B H 0.1435 0.4195 0.5568 0.020 Uiso 1 1 calc R . .
C17B C 0.21646(7) 0.33776(7) 0.65951(13) 0.0196(3) Uani 1 1 d . . .
H17D H 0.1991 0.3231 0.5787 0.029 Uiso 1 1 calc R . .
H17E H 0.2012 0.3067 0.7196 0.029 Uiso 1 1 calc R . .
H17F H 0.2576 0.3542 0.6533 0.029 Uiso 1 1 calc R . .
C18B C 0.24973(7) 0.45977(7) 1.02098(14) 0.0216(3) Uani 1 1 d . . .
H18D H 0.2344 0.4780 1.0745 0.032 Uiso 1 1 calc R . .
H18E H 0.2900 0.4862 1.0054 0.032 Uiso 1 1 calc R . .
H18F H 0.2454 0.4256 1.0615 0.032 Uiso 1 1 calc R . .
C19B C 0.22285(7) 0.49600(7) 0.83604(14) 0.0210(3) Uani 1 1 d . . .
H19D H 0.1962 0.4844 0.7667 0.032 Uiso 1 1 calc R . .
H19E H 0.2616 0.5197 0.8055 0.032 Uiso 1 1 calc R . .
H19F H 0.2140 0.5176 0.8954 0.032 Uiso 1 1 calc R . .
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
S1A 0.01718(16) 0.01948(17) 0.01682(15) 0.00436(12) 0.00118(12) 0.00892(14)
O2A 0.0229(5) 0.0218(5) 0.0202(5) -0.0043(4) -0.0066(4) 0.0130(5)
C2A 0.0177(7) 0.0172(7) 0.0157(6) -0.0005(5) 0.0005(5) 0.0100(6)
C3A 0.0198(7) 0.0146(6) 0.0151(6) -0.0010(5) -0.0007(5) 0.0086(6)
C4A 0.0156(6) 0.0153(6) 0.0131(6) 0.0002(5) -0.0001(5) 0.0073(5)
C5A 0.0144(6) 0.0144(6) 0.0175(6) -0.0033(5) -0.0042(5) 0.0058(5)
C6A 0.0178(7) 0.0221(7) 0.0170(6) -0.0011(5) -0.0020(5) 0.0099(6)
C7A 0.0176(7) 0.0250(7) 0.0219(7) -0.0060(6) -0.0038(5) 0.0115(6)
C8A 0.0206(7) 0.0222(7) 0.0281(8) -0.0066(6) -0.0077(6) 0.0147(6)
C9A 0.0218(7) 0.0150(6) 0.0242(7) -0.0005(5) -0.0064(6) 0.0092(6)
C10A 0.0127(6) 0.0142(6) 0.0186(6) -0.0036(5) -0.0027(5) 0.0051(5)
C11A 0.0161(6) 0.0147(6) 0.0137(6) 0.0014(5) 0.0023(5) 0.0075(5)
C12A 0.0201(7) 0.0147(6) 0.0162(6) 0.0000(5) 0.0015(5) 0.0092(5)
C13A 0.0222(7) 0.0196(7) 0.0172(6) 0.0020(5) 0.0016(5) 0.0137(6)
C14A 0.0173(7) 0.0193(7) 0.0130(6) 0.0001(5) -0.0005(5) 0.0087(6)
C15A 0.0210(7) 0.0157(6) 0.0160(6) -0.0010(5) 0.0007(5) 0.0104(6)
C16A 0.0187(7) 0.0173(7) 0.0150(6) 0.0012(5) 0.0014(5) 0.0103(5)
C17A 0.0188(7) 0.0151(7) 0.0214(7) 0.0020(5) 0.0009(5) 0.0061(6)
C18A 0.0280(8) 0.0229(7) 0.0188(6) 0.0005(5) 0.0048(6) 0.0136(6)
C19A 0.0161(7) 0.0193(7) 0.0202(6) 0.0016(5) 0.0013(5) 0.0065(6)
O1B 0.0186(5) 0.0222(5) 0.0176(5) -0.0025(4) 0.0020(4) 0.0099(4)
O2B 0.0178(6) 0.0222(6) 0.0208(5) 0.0059(4) 0.0036(4) 0.0097(5)
C2B 0.0165(7) 0.0182(7) 0.0160(6) -0.0003(5) -0.0001(5) 0.0090(6)
C3B 0.0150(6) 0.0182(6) 0.0155(6) 0.0007(5) -0.0004(5) 0.0088(6)
C4B 0.0152(6) 0.0166(6) 0.0154(6) -0.0013(5) -0.0004(5) 0.0092(5)
C5B 0.0166(7) 0.0155(6) 0.0155(6) 0.0016(5) -0.0004(5) 0.0083(5)
C6B 0.0200(7) 0.0179(7) 0.0183(6) 0.0019(5) 0.0007(5) 0.0088(6)
C7B 0.0178(7) 0.0173(7) 0.0237(7) 0.0029(5) -0.0042(5) 0.0059(6)
C8B 0.0164(7) 0.0204(7) 0.0291(8) 0.0079(6) 0.0029(6) 0.0094(6)
C9B 0.0182(7) 0.0204(7) 0.0235(7) 0.0042(5) 0.0046(5) 0.0113(6)
C10B 0.0170(7) 0.0160(6) 0.0176(6) 0.0022(5) 0.0018(5) 0.0092(5)
C11B 0.0175(7) 0.0162(6) 0.0128(6) -0.0030(5) -0.0007(5) 0.0083(6)
C12B 0.0153(7) 0.0225(7) 0.0180(6) 0.0002(5) -0.0015(5) 0.0114(6)
C13B 0.0141(6) 0.0204(7) 0.0184(7) 0.0001(5) 0.0011(5) 0.0073(5)
C14B 0.0184(7) 0.0153(6) 0.0146(6) -0.0006(5) 0.0009(5) 0.0079(5)
C15B 0.0173(7) 0.0203(7) 0.0147(6) -0.0015(5) -0.0017(5) 0.0105(6)
C16B 0.0125(6) 0.0181(6) 0.0177(6) -0.0029(5) -0.0005(5) 0.0072(5)
C17B 0.0228(7) 0.0211(7) 0.0170(6) -0.0007(5) 0.0007(5) 0.0126(6)
C18B 0.0243(7) 0.0256(7) 0.0176(6) -0.0038(5) -0.0046(5) 0.0144(6)
C19B 0.0259(8) 0.0218(7) 0.0193(7) -0.0002(5) -0.0004(5) 0.0148(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1A C10A 1.7618(15) . ?
S1A C2A 1.8282(15) . ?
O2A C14A 1.3816(18) . ?
C2A C3A 1.525(2) . ?
C2A C18A 1.5259(19) . ?
C2A C19A 1.531(2) . ?
C3A C4A 1.5489(18) . ?
C4A C5A 1.534(2) . ?
C4A C11A 1.5441(19) . ?
C4A C17A 1.550(2) . ?
C5A C10A 1.399(2) . ?
C5A C6A 1.400(2) . ?
C6A C7A 1.392(2) . ?
C7A C8A 1.395(2) . ?
C8A C9A 1.371(2) . ?
C9A C10A 1.408(2) . ?
C11A C16A 1.396(2) . ?
C11A C12A 1.405(2) . ?
C12A C13A 1.393(2) . ?
C13A C14A 1.392(2) . ?
C14A C15A 1.387(2) . ?
C15A C16A 1.391(2) . ?
O1B C10B 1.3640(18) . ?
O1B C2B 1.4557(18) . ?
O2B C14B 1.3779(18) . ?
C2B C18B 1.5224(19) . ?
C2B C19B 1.525(2) . ?
C2B C3B 1.527(2) . ?
C3B C4B 1.5422(19) . ?
C4B C5B 1.5249(19) . ?
C4B C17B 1.543(2) . ?
C4B C11B 1.5453(19) . ?
C5B C6B 1.400(2) . ?
C5B C10B 1.402(2) . ?
C6B C7B 1.393(2) . ?
C7B C8B 1.391(2) . ?
C8B C9B 1.379(2) . ?
C9B C10B 1.405(2) . ?
C11B C16B 1.393(2) . ?
C11B C12B 1.395(2) . ?
C12B C13B 1.390(2) . ?
C13B C14B 1.391(2) . ?
C14B C15B 1.387(2) . ?
C15B C16B 1.395(2) . ?
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
C10A S1A C2A 102.77(6) . . ?
C3A C2A C18A 109.24(12) . . ?
C3A C2A C19A 114.96(12) . . ?
C18A C2A C19A 110.09(12) . . ?
C3A C2A S1A 107.58(10) . . ?
C18A C2A S1A 104.59(10) . . ?
C19A C2A S1A 109.85(10) . . ?
C2A C3A C4A 118.90(12) . . ?
C5A C4A C11A 111.10(11) . . ?
C5A C4A C3A 112.16(11) . . ?
C11A C4A C3A 110.45(11) . . ?
C5A C4A C17A 108.84(11) . . ?
C11A C4A C17A 109.05(11) . . ?
C3A C4A C17A 105.01(11) . . ?
C10A C5A C6A 117.20(13) . . ?
C10A C5A C4A 124.07(13) . . ?
C6A C5A C4A 118.73(12) . . ?
C7A C6A C5A 122.44(14) . . ?
C6A C7A C8A 119.31(14) . . ?
C9A C8A C7A 119.47(13) . . ?
C8A C9A C10A 121.22(14) . . ?
C5A C10A C9A 120.34(13) . . ?
C5A C10A S1A 125.60(11) . . ?
C9A C10A S1A 113.95(11) . . ?
C16A C11A C12A 116.86(13) . . ?
C16A C11A C4A 123.36(13) . . ?
C12A C11A C4A 119.76(12) . . ?
C13A C12A C11A 121.54(13) . . ?
C14A C13A C12A 120.03(13) . . ?
O2A C14A C15A 118.07(13) . . ?
O2A C14A C13A 122.44(13) . . ?
C15A C14A C13A 119.48(13) . . ?
C14A C15A C16A 119.87(13) . . ?
C15A C16A C11A 122.19(13) . . ?
C10B O1B C2B 117.70(11) . . ?
O1B C2B C18B 105.03(11) . . ?
O1B C2B C19B 108.06(12) . . ?
C18B C2B C19B 110.18(12) . . ?
O1B C2B C3B 109.38(11) . . ?
C18B C2B C3B 109.56(12) . . ?
C19B C2B C3B 114.21(12) . . ?
C2B C3B C4B 115.20(12) . . ?
C5B C4B C3B 107.88(11) . . ?
C5B C4B C17B 110.06(12) . . ?
C3B C4B C17B 106.77(11) . . ?
C5B C4B C11B 112.26(11) . . ?
C3B C4B C11B 111.83(11) . . ?
C17B C4B C11B 107.90(11) . . ?
C6B C5B C10B 117.88(13) . . ?
C6B C5B C4B 120.93(12) . . ?
C10B C5B C4B 121.18(13) . . ?
C7B C6B C5B 122.02(14) . . ?
C8B C7B C6B 119.01(14) . . ?
C9B C8B C7B 120.34(14) . . ?
C8B C9B C10B 120.55(14) . . ?
O1B C10B C5B 124.84(13) . . ?
O1B C10B C9B 114.94(13) . . ?
C5B C10B C9B 120.17(14) . . ?
C16B C11B C12B 117.00(13) . . ?
C16B C11B C4B 124.01(13) . . ?
C12B C11B C4B 118.99(12) . . ?
C13B C12B C11B 122.33(13) . . ?
C12B C13B C14B 119.44(13) . . ?
O2B C14B C15B 118.30(13) . . ?
O2B C14B C13B 122.17(13) . . ?
C15B C14B C13B 119.53(13) . . ?
C14B C15B C16B 120.07(13) . . ?
C11B C16B C15B 121.61(13) . . ?
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
C10A S1A C2A C3A 43.47(11) . . . . ?
C10A S1A C2A C18A 159.55(10) . . . . ?
C10A S1A C2A C19A -82.33(10) . . . . ?
C18A C2A C3A C4A -177.47(12) . . . . ?
C19A C2A C3A C4A 58.21(17) . . . . ?
S1A C2A C3A C4A -64.48(14) . . . . ?
C2A C3A C4A C5A 48.93(17) . . . . ?
C2A C3A C4A C11A -75.59(15) . . . . ?
C2A C3A C4A C17A 166.98(12) . . . . ?
C11A C4A C5A C10A 109.08(14) . . . . ?
C3A C4A C5A C10A -15.08(19) . . . . ?
C17A C4A C5A C10A -130.83(13) . . . . ?
C11A C4A C5A C6A -70.65(16) . . . . ?
C3A C4A C5A C6A 165.19(12) . . . . ?
C17A C4A C5A C6A 49.43(16) . . . . ?
C10A C5A C6A C7A -0.9(2) . . . . ?
C4A C5A C6A C7A 178.84(13) . . . . ?
C5A C6A C7A C8A 0.2(2) . . . . ?
C6A C7A C8A C9A 0.5(2) . . . . ?
C7A C8A C9A C10A -0.6(2) . . . . ?
C6A C5A C10A C9A 0.84(19) . . . . ?
C4A C5A C10A C9A -178.90(13) . . . . ?
C6A C5A C10A S1A -175.32(11) . . . . ?
C4A C5A C10A S1A 4.9(2) . . . . ?
C8A C9A C10A C5A -0.1(2) . . . . ?
C8A C9A C10A S1A 176.46(12) . . . . ?
C2A S1A C10A C5A -18.78(13) . . . . ?
C2A S1A C10A C9A 164.85(10) . . . . ?
C5A C4A C11A C16A -5.39(19) . . . . ?
C3A C4A C11A C16A 119.73(14) . . . . ?
C17A C4A C11A C16A -125.35(14) . . . . ?
C5A C4A C11A C12A 176.42(12) . . . . ?
C3A C4A C11A C12A -58.46(16) . . . . ?
C17A C4A C11A C12A 56.46(16) . . . . ?
C16A C11A C12A C13A -1.6(2) . . . . ?
C4A C11A C12A C13A 176.70(13) . . . . ?
C11A C12A C13A C14A 0.3(2) . . . . ?
C12A C13A C14A O2A -177.78(13) . . . . ?
C12A C13A C14A C15A 1.5(2) . . . . ?
O2A C14A C15A C16A 177.31(13) . . . . ?
C13A C14A C15A C16A -2.0(2) . . . . ?
C14A C15A C16A C11A 0.7(2) . . . . ?
C12A C11A C16A C15A 1.1(2) . . . . ?
C4A C11A C16A C15A -177.14(13) . . . . ?
C10B O1B C2B C18B -158.22(12) . . . . ?
C10B O1B C2B C19B 84.18(14) . . . . ?
C10B O1B C2B C3B -40.70(16) . . . . ?
O1B C2B C3B C4B 57.14(15) . . . . ?
C18B C2B C3B C4B 171.77(12) . . . . ?
C19B C2B C3B C4B -64.10(16) . . . . ?
C2B C3B C4B C5B -43.83(16) . . . . ?
C2B C3B C4B C17B -162.10(12) . . . . ?
C2B C3B C4B C11B 80.09(15) . . . . ?
C3B C4B C5B C6B -162.29(13) . . . . ?
C17B C4B C5B C6B -46.14(17) . . . . ?
C11B C4B C5B C6B 74.05(16) . . . . ?
C3B C4B C5B C10B 16.42(18) . . . . ?
C17B C4B C5B C10B 132.56(13) . . . . ?
C11B C4B C5B C10B -107.25(14) . . . . ?
C10B C5B C6B C7B 1.5(2) . . . . ?
C4B C5B C6B C7B -179.80(13) . . . . ?
C5B C6B C7B C8B -0.5(2) . . . . ?
C6B C7B C8B C9B -1.0(2) . . . . ?
C7B C8B C9B C10B 1.5(2) . . . . ?
C2B O1B C10B C5B 15.27(19) . . . . ?
C2B O1B C10B C9B -167.27(12) . . . . ?
C6B C5B C10B O1B 176.40(13) . . . . ?
C4B C5B C10B O1B -2.3(2) . . . . ?
C6B C5B C10B C9B -0.9(2) . . . . ?
C4B C5B C10B C9B -179.68(13) . . . . ?
C8B C9B C10B O1B -178.09(13) . . . . ?
C8B C9B C10B C5B -0.5(2) . . . . ?
C5B C4B C11B C16B -3.43(19) . . . . ?
C3B C4B C11B C16B -124.86(14) . . . . ?
C17B C4B C11B C16B 118.01(15) . . . . ?
C5B C4B C11B C12B 177.15(12) . . . . ?
C3B C4B C11B C12B 55.72(17) . . . . ?
C17B C4B C11B C12B -61.41(16) . . . . ?
C16B C11B C12B C13B 0.8(2) . . . . ?
C4B C11B C12B C13B -179.73(13) . . . . ?
C11B C12B C13B C14B -0.2(2) . . . . ?
C12B C13B C14B O2B 178.88(13) . . . . ?
C12B C13B C14B C15B -0.9(2) . . . . ?
O2B C14B C15B C16B -178.34(12) . . . . ?
C13B C14B C15B C16B 1.5(2) . . . . ?
C12B C11B C16B C15B -0.3(2) . . . . ?
C4B C11B C16B C15B -179.69(12) . . . . ?
C14B C15B C16B C11B -0.9(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2A H2AA O2B 0.88(3) 1.90(3) 2.7878(18) 179(3) .
O2B H2BA O2A 0.72(3) 2.11(3) 2.8330(18) 172(3) 2_665
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 74.31
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.244
_refine_diff_density_min -0.152
_refine_diff_density_rms 0.038
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.108 225 7 ' '
2 0.333 0.667 0.850 219 7 ' '
3 0.667 0.333 0.516 220 7 ' '
_platon_squeeze_details
;
PLATON(V-280612)
PLATON Reference
Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
Spek, A.L. (2009). Acta Cryst. D65, 148-155.
;
_database_code_depnum_ccdc_archive 'CCDC 945012'