# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010

data_global
_journal_name_full               'New J.Chem.'

_journal_coden_Cambridge         0440

_publ_contact_author_name        'Merwe Albrecht'
_publ_contact_author_email       msuhm@gwdg.de

_publ_section_title              
;
Chirality influence on the aggregation of methyl mandelate
;
loop_
_publ_author_name
M.Albrecht
A.Borba
'K.Le Barbu-Debus'
B.Dittrich
R.Fausto
;
S.Grimme
;
A.Mahjoub
M.Nedia
U.Schmitt
L.Schrader
M.Suhm
;
A.Zehnacker-Rentien
;
J.Zischang

# Attachment 'rrrssssr.cif'

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 2010-01-06 at 20:19:33
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.2
# Request file : /Local/xdbig/lib/xd/xdcif.dat
# CIF files read : fft geo lsm

#CHECKCIF gave the following B-Alert
#PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
#Indeed the data completeness is not 100 % up to the Acta limit.
#Since the structure is triclinic it was not possible
#to achieve full completeness with Cu Kalpha radiation in the given orientation
#with our measurement strategy.

data_rrrssssr
_database_code_depnum_ccdc_archive 'CCDC 762619'
#TrackingRef 'rrrssssr.cif'

_audit_creation_date             2010-01-06T20:19:33-00:00
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_weight         166.17
_exptl_crystal_density_diffrn    1.3212
_chemical_absolute_configuration .
_exptl_crystal_F_000             704.0
_chemical_compound_source        ' Sigma Aldrich '

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0191 0.0091 'Invariom modelling (Acta Cryst. A61, 314--320)'
H H 0.0000 0.0000 'Invariom modelling (Acta Cryst. A61, 314--320)'
O O 0.0522 0.0322 'Invariom modelling (Acta Cryst. A61, 314--320)'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z

_cell_length_a                   7.8576(2)
_cell_length_b                   11.0894(4)
_cell_length_c                   20.0502(7)
_cell_angle_alpha                103.782(2)
_cell_angle_beta                 98.959(2)
_cell_angle_gamma                92.247(2)
_cell_volume                     1670.8(1)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.305
_cell_measurement_theta_max      72.65
_cell_measurement_temperature    100
_cell_formula_units_Z            8.0
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_cell_setting           triclinic

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_min  0.6436
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS, multi-scan. (G. M. Sheldrick, 2008)
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_device_type  'Bruker Apex 2 Diffractometer'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_number            26447
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.305
_diffrn_measured_fraction_theta_max 0.895
_diffrn_reflns_theta_full        72.5
_diffrn_measured_fraction_theta_full 0.95
_diffrn_reflns_theta_max         67.6
_diffrn_orient_matrix_UB_11      1.2873706e-01
_diffrn_orient_matrix_UB_12      1.5581626e-02
_diffrn_orient_matrix_UB_13      1.0290211e-02
_diffrn_orient_matrix_UB_21      -1.0435561e-02
_diffrn_orient_matrix_UB_22      8.0007508e-02
_diffrn_orient_matrix_UB_23      3.4329090e-02
_diffrn_orient_matrix_UB_31      4.7348784e-03
_diffrn_orient_matrix_UB_32      -4.5076210e-02
_diffrn_orient_matrix_UB_33      3.7833247e-02

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4717
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.046
_refine_ls_wR_factor_ref         0.0491
_refine_ls_goodness_of_fit_ref   3.5099
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.06
_reflns_threshold_expression     F>3(\s)F
_reflns_number_total             5946
_reflns_number_gt                4717
_refine_ls_hydrogen_treatment    constr

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
O(11) -0.2127(2) 0.08910(10) 0.35070(10) 0.028 1
O(12) -0.1806(2) 0.26990(10) 0.43200(10) 0.028 1
O(13) -0.1577(2) 0.20170(10) 0.25320(10) 0.03 1
O(21) -0.2115(2) 0.58850(10) 0.34070(10) 0.03 1
O(22) -0.1681(2) 0.76670(10) 0.42420(10) 0.029 1
O(23) -0.1360(2) 0.69960(10) 0.24560(10) 0.028 1
O(31) -0.1583(2) 0.21340(10) 0.11230(10) 0.034 1
O(32) -0.0986(2) 0.30600(10) 0.02990(10) 0.034 1
O(33) -0.1466(2) 0.42890(10) 0.20490(10) 0.028 1
O(41) 0.7677(2) 0.72000(10) 0.10890(10) 0.034 1
O(42) 0.6140(2) 0.80090(10) 0.02830(10) 0.033 1
O(43) 0.8151(2) 0.93530(10) 0.20310(10) 0.028 1
C(11) -0.2319(3) 0.2030(2) 0.48020(10) 0.035 1
C(12) -0.1767(2) 0.1997(2) 0.36820(10) 0.023 1
C(13) -0.1174(3) 0.2775(2) 0.32150(10) 0.024 1
C(14) 0.0759(3) 0.3144(2) 0.34460(10) 0.023 1
C(15) 0.1361(3) 0.4343(2) 0.38350(10) 0.032 1
C(16) 0.3132(3) 0.4662(2) 0.40340(10) 0.04 1
C(17) 0.4311(3) 0.3792(2) 0.38470(10) 0.037 1
C(18) 0.3704(3) 0.2592(2) 0.34630(10) 0.035 1
C(19) 0.1938(3) 0.2267(2) 0.32720(10) 0.029 1
C(21) -0.2268(3) 0.7003(2) 0.47130(10) 0.036 1
C(22) -0.1676(2) 0.6981(2) 0.35980(10) 0.023 1
C(23) -0.1027(3) 0.7758(2) 0.31390(10) 0.024 1
C(24) 0.0886(3) 0.8158(2) 0.33900(10) 0.022 1
C(25) 0.1430(3) 0.9325(2) 0.38370(10) 0.028 1
C(26) 0.3187(3) 0.9680(2) 0.40600(10) 0.032 1
C(27) 0.4420(3) 0.8876(2) 0.38430(10) 0.03 1
C(28) 0.3878(3) 0.7709(2) 0.34010(10) 0.031 1
C(29) 0.2125(3) 0.7351(2) 0.31760(10) 0.028 1
C(31) -0.1180(3) 0.1858(2) -0.01900(10) 0.035 1
C(32) -0.1208(3) 0.3058(2) 0.09430(10) 0.026 1
C(33) -0.0900(3) 0.4363(2) 0.14240(10) 0.026 1
C(34) 0.1001(3) 0.4791(2) 0.15190(10) 0.025 1
C(35) 0.1532(3) 0.5651(2) 0.11760(10) 0.03 1
C(36) 0.3254(3) 0.6041(2) 0.12560(10) 0.03 1
C(37) 0.4501(3) 0.5571(2) 0.16900(10) 0.033 1
C(38) 0.3977(3) 0.4689(2) 0.20270(10) 0.032 1
C(39) 0.2242(3) 0.4307(2) 0.19460(10) 0.028 1
C(41) 0.5961(3) 0.6803(2) -0.02000(10) 0.037 1
C(42) 0.7023(3) 0.8076(2) 0.09180(10) 0.027 1
C(43) 0.7106(3) 0.9386(2) 0.13910(10) 0.026 1
C(44) 0.5304(3) 0.9773(2) 0.14720(10) 0.025 1
C(45) 0.4377(3) 0.9288(2) 0.19040(10) 0.028 1
C(46) 0.2714(3) 0.9613(2) 0.19690(10) 0.032 1
C(47) 0.1975(3) 1.0468(2) 0.16160(10) 0.033 1
C(48) 0.2921(3) 1.0968(2) 0.12000(10) 0.03 1
C(49) 0.4562(3) 1.0614(2) 0.11170(10) 0.03 1
H(13) -0.16593 0.25222 0.22015 0.0441(6) 1
H(11A) -0.36637 0.16468 0.46255 0.0404(7) 1
H(11B) -0.21849 0.26566 0.53231 0.0404(7) 1
H(11C) -0.14885 0.12651 0.48233 0.0404(7) 1
H(13A) -0.18861 0.3615 0.32597 0.0275(6) 1
H(15) 0.04546 0.50259 0.39842 0.0363(6) 1
H(16) 0.35977 0.55931 0.43366 0.0454(7) 1
H(17) 0.56866 0.40435 0.39953 0.0407(7) 1
H(18) 0.46094 0.19075 0.33143 0.0387(7) 1
H(19) 0.14761 0.13271 0.29818 0.0337(6) 1
H(23) -0.15692 0.74944 0.21245 0.0414(5) 1
H(21A) -0.36365 0.66852 0.45357 0.0412(7) 1
H(21B) -0.20861 0.76113 0.52397 0.0412(7) 1
H(21C) -0.15195 0.61916 0.47169 0.0412(7) 1
H(23A) -0.17569 0.85874 0.31612 0.0277(6) 1
H(25) 0.04797 0.99555 0.40075 0.0314(6) 1
H(26) 0.35952 1.05836 0.44113 0.0363(6) 1
H(27) 0.57828 0.9161 0.40122 0.0340(6) 1
H(28) 0.48291 0.70762 0.32322 0.0356(6) 1
H(29) 0.17195 0.64436 0.2828 0.0329(6) 1
H(33) -0.15748 0.51098 0.23252 0.0398(5) 1
H(31A) -0.02731 0.12483 0.00068 0.0418(7) 1
H(31B) -0.09029 0.19579 -0.06938 0.0418(7) 1
H(31C) -0.25016 0.14426 -0.02574 0.0418(7) 1
H(33A) -0.16775 0.49984 0.11832 0.0289(6) 1
H(35) 0.05861 0.60222 0.08417 0.0348(6) 1
H(36) 0.36645 0.67102 0.09873 0.0351(6) 1
H(37) 0.58529 0.58868 0.1761 0.0397(6) 1
H(38) 0.49259 0.43096 0.23561 0.0377(6) 1
H(39) 0.18357 0.36274 0.22091 0.0322(6) 1
H(43) 0.82623 1.01622 0.2349 0.0408(5) 1
H(41A) 0.72438 0.65057 -0.02769 0.0437(7) 1
H(41B) 0.52164 0.68552 -0.07003 0.0437(7) 1
H(41C) 0.52901 0.61284 0.00079 0.0437(7) 1
H(43A) 0.77463 1.00386 0.11562 0.0286(6) 1
H(45) 0.49506 0.86427 0.21851 0.0327(6) 1
H(46) 0.19881 0.92153 0.22926 0.0371(6) 1
H(47) 0.06863 1.07395 0.16721 0.0386(6) 1
H(48) 0.23599 1.16393 0.09353 0.0340(6) 1
H(49) 0.52646 1.09929 0.07801 0.0343(6) 1
#DUM0 0 0 0 0 0
#DUM1 -0.33641 0.10308 0.33587 0 0
#DUM2 -0.21195 0.17885 0.42155 0 0
#DUM3 -0.33315 0.60769 0.32639 0 0
#DUM4 -0.20681 0.67658 0.4126 0 0
#DUM5 -0.03289 0.20141 0.12468 0 0
#DUM6 -0.12638 0.22503 0.04053 0 0
#DUM7 0.87697 0.7426 0.09334 0 0
#DUM8 0.66181 0.72436 0.03855 0 0
#DUM9 0.22006 0.37047 0.36977 0 0
#DUM10 0.26962 0.37943 0.37511 0 0
#DUM11 0.30287 0.35538 0.37052 0 0
#DUM12 0.28607 0.3229 0.36023 0 0
#DUM13 0.2361 0.31453 0.35393 0 0
#DUM14 0.23055 0.87332 0.36742 0 0
#DUM15 0.2803 0.88342 0.37376 0 0
#DUM16 0.31487 0.86147 0.36823 0 0
#DUM17 0.29959 0.82997 0.35581 0 0
#DUM18 0.24963 0.82012 0.34966 0 0
#DUM19 0.23989 0.5302 0.14875 0 0
#DUM20 0.29016 0.54153 0.15133 0 0
#DUM21 0.324 0.52721 0.16229 0 0
#DUM22 0.31037 0.50506 0.17257 0 0
#DUM23 0.26029 0.49375 0.16947 0 0
#DUM24 0.38524 0.98793 0.16355 0 0
#DUM25 0.33819 0.99947 0.16682 0 0
#DUM26 0.31788 1.02177 0.15696 0 0
#DUM27 0.34285 1.03416 0.14472 0 0
#DUM28 0.39135 1.02588 0.14345 0 0

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
O(11) 0.0372(9) 0.0233(8) 0.0239(7) 0.0094(6) 0.0101(6) -0.0001(6)
O(12) 0.0287(8) 0.0310(8) 0.0215(7) 0.0072(6) 0.0079(6) 0.0011(6)
O(13) 0.0388(9) 0.0306(8) 0.0182(7) 0.0098(6) 0.0014(6) -0.0026(7)
O(21) 0.0381(9) 0.0237(8) 0.0262(8) 0.0094(7) 0.0103(7) 0.0002(7)
O(22) 0.0286(8) 0.0324(8) 0.0232(7) 0.0077(6) 0.0079(6) 0.0003(7)
O(23) 0.0340(9) 0.0294(8) 0.0189(7) 0.0098(6) -0.0003(6) -0.0010(7)
O(31) 0.0540(10) 0.0230(10) 0.0230(10) 0.0090(10) 0.0120(10) -0.0060(10)
O(32) 0.0470(10) 0.0290(10) 0.0230(10) 0.0090(10) 0.0070(10) -0.0050(10)
O(33) 0.0316(9) 0.0269(7) 0.0238(7) 0.0086(6) 0.0125(6) 0.0005(6)
O(41) 0.0530(10) 0.0240(10) 0.0230(10) 0.0100(10) 0.0080(10) 0.0110(10)
O(42) 0.0440(10) 0.0310(10) 0.0230(10) 0.0090(10) 0.0090(10) 0.0080(10)
O(43) 0.0306(9) 0.0270(7) 0.0237(7) 0.0078(6) 0.0030(6) 0.0018(6)
C(11) 0.0350(10) 0.0460(10) 0.0230(10) 0.0130(10) 0.0110(10) 0.0000(10)
C(12) 0.0230(10) 0.0250(10) 0.0210(10) 0.0090(10) 0.0060(10) 0.0010(10)
C(13) 0.0260(10) 0.0230(10) 0.0220(10) 0.0110(10) 0.0070(10) 0.0020(10)
C(14) 0.0250(10) 0.0230(10) 0.0200(10) 0.0090(10) 0.0070(10) 0.0030(10)
C(15) 0.0250(10) 0.0240(10) 0.0440(10) 0.0070(10) 0.0080(10) 0.0030(10)
C(16) 0.0270(10) 0.0260(10) 0.061(2) 0.0090(10) 0.0060(10) 0.0010(10)
C(17) 0.0230(10) 0.0370(10) 0.0490(10) 0.0170(10) 0.0090(10) 0.0040(10)
C(18) 0.0290(10) 0.0380(10) 0.0350(10) 0.0110(10) 0.0120(10) 0.0110(10)
C(19) 0.0300(10) 0.0290(10) 0.0260(10) 0.0060(10) 0.0090(10) 0.0060(10)
C(21) 0.0350(10) 0.0460(10) 0.0270(10) 0.0120(10) 0.0130(10) 0.0010(10)
C(22) 0.0220(10) 0.0250(10) 0.0220(10) 0.0080(10) 0.0050(10) 0.0010(10)
C(23) 0.0250(10) 0.0230(10) 0.0230(10) 0.0100(10) 0.0040(10) 0.0020(10)
C(24) 0.0220(10) 0.0230(10) 0.0190(10) 0.0080(10) 0.0050(10) 0.0030(10)
C(25) 0.0260(10) 0.0240(10) 0.0310(10) 0.0050(10) 0.0070(10) 0.0040(10)
C(26) 0.0260(10) 0.0240(10) 0.0410(10) 0.0060(10) 0.0050(10) 0.0000(10)
C(27) 0.0240(10) 0.0340(10) 0.0320(10) 0.0110(10) 0.0070(10) 0.0010(10)
C(28) 0.0260(10) 0.0380(10) 0.0270(10) 0.0040(10) 0.0080(10) 0.0080(10)
C(29) 0.0270(10) 0.0290(10) 0.0250(10) 0.0020(10) 0.0050(10) 0.0060(10)
C(31) 0.0450(10) 0.0320(10) 0.0240(10) 0.0070(10) 0.0050(10) -0.0020(10)
C(32) 0.0280(10) 0.0240(10) 0.0230(10) 0.0100(10) 0.0050(10) -0.0030(10)
C(33) 0.0270(10) 0.0240(10) 0.0250(10) 0.0100(10) 0.0080(10) 0.0020(10)
C(34) 0.0280(10) 0.0240(10) 0.0230(10) 0.0080(10) 0.0090(10) 0.0010(10)
C(35) 0.0320(10) 0.0250(10) 0.0330(10) 0.0120(10) 0.0110(10) 0.0010(10)
C(36) 0.0310(10) 0.0260(10) 0.0330(10) 0.0120(10) 0.0120(10) 0.0000(10)
C(37) 0.0280(10) 0.0330(10) 0.0350(10) 0.0050(10) 0.0090(10) -0.0040(10)
C(38) 0.0280(10) 0.0390(10) 0.0270(10) 0.0120(10) 0.0050(10) 0.0010(10)
C(39) 0.0300(10) 0.0310(10) 0.0210(10) 0.0110(10) 0.0080(10) 0.0070(10)
C(41) 0.051(2) 0.0350(10) 0.0230(10) 0.0070(10) 0.0140(10) 0.0050(10)
C(42) 0.0320(10) 0.0260(10) 0.0250(10) 0.0110(10) 0.0120(10) 0.0040(10)
C(43) 0.0260(10) 0.0240(10) 0.0270(10) 0.0100(10) 0.0090(10) 0.0030(10)
C(44) 0.0260(10) 0.0250(10) 0.0240(10) 0.0100(10) 0.0080(10) 0.0020(10)
C(45) 0.0310(10) 0.0320(10) 0.0220(10) 0.0140(10) 0.0080(10) 0.0010(10)
C(46) 0.0380(10) 0.0340(10) 0.0240(10) 0.0100(10) 0.0160(10) 0.0060(10)
C(47) 0.0290(10) 0.0360(10) 0.0320(10) 0.0060(10) 0.0120(10) 0.0060(10)
C(48) 0.0300(10) 0.0270(10) 0.0310(10) 0.0120(10) 0.0090(10) 0.0070(10)
C(49) 0.0310(10) 0.0270(10) 0.0300(10) 0.0140(10) 0.0090(10) 0.0020(10)

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(11) DUM1 Z O(11) C(12) Y
O(12) DUM2 Z O(12) C(11) Y
O(13) C(13) X O(13) H(13) Y
O(21) DUM3 Z O(21) C(22) Y
O(22) DUM4 Z O(22) C(21) Y
O(23) C(23) X O(23) H(23) Y
O(31) DUM5 Z O(31) C(32) Y
O(32) DUM6 Z O(32) C(31) Y
O(33) C(33) X O(33) H(33) Y
O(41) DUM7 Z O(41) C(42) Y
O(42) DUM8 Z O(42) C(41) Y
O(43) C(43) X O(43) H(43) Y
C(11) O(12) Z C(11) H(11A) Y
C(12) O(11) X C(12) O(12) Y
C(13) O(13) X C(13) C(12) Y
C(14) C(13) Z C(14) C(15) Y
C(15) DUM9 Z C(15) C(14) Y
C(16) DUM10 Z C(16) C(15) Y
C(17) DUM11 Z C(17) C(16) Y
C(18) DUM12 Z C(18) C(17) Y
C(19) DUM13 Z C(19) C(14) Y
C(21) O(22) Z C(21) H(21A) Y
C(22) O(21) X C(22) O(22) Y
C(23) O(23) X C(23) C(22) Y
C(24) C(23) Z C(24) C(25) Y
C(25) DUM14 Z C(25) C(24) Y
C(26) DUM15 Z C(26) C(25) Y
C(27) DUM16 Z C(27) C(26) Y
C(28) DUM17 Z C(28) C(27) Y
C(29) DUM18 Z C(29) C(24) Y
C(31) O(32) Z C(31) H(31A) Y
C(32) O(31) X C(32) O(32) Y
C(33) O(33) X C(33) C(32) Y
C(34) C(33) Z C(34) C(35) Y
C(35) DUM19 Z C(35) C(34) Y
C(36) DUM20 Z C(36) C(35) Y
C(37) DUM21 Z C(37) C(36) Y
C(38) DUM22 Z C(38) C(37) Y
C(39) DUM23 Z C(39) C(34) Y
C(41) O(42) Z C(41) H(41A) Y
C(42) O(41) X C(42) O(42) Y
C(43) O(43) X C(43) C(42) Y
C(44) C(43) Z C(44) C(45) Y
C(45) DUM24 Z C(45) C(44) Y
C(46) DUM25 Z C(46) C(45) Y
C(47) DUM26 Z C(47) C(46) Y
C(48) DUM27 Z C(48) C(47) Y
C(49) DUM28 Z C(49) C(44) Y
H(13) O(13) Z H(13) C(13) Y
H(11A) C(11) Z H(11A) O(12) Y
H(11B) C(11) Z H(11B) O(12) Y
H(11C) C(11) Z H(11C) O(12) Y
H(13A) C(13) Z H(13A) O(13) Y
H(15) C(15) Z H(15) C(14) Y
H(16) C(16) Z H(16) C(15) Y
H(17) C(17) Z H(17) C(16) Y
H(18) C(18) Z H(18) C(17) Y
H(19) C(19) Z H(19) C(14) Y
H(23) O(23) Z H(23) C(23) Y
H(21A) C(21) Z H(21A) O(22) Y
H(21B) C(21) Z H(21B) O(22) Y
H(21C) C(21) Z H(21C) O(22) Y
H(23A) C(23) Z H(23A) O(23) Y
H(25) C(25) Z H(25) C(24) Y
H(26) C(26) Z H(26) C(25) Y
H(27) C(27) Z H(27) C(26) Y
H(28) C(28) Z H(28) C(27) Y
H(29) C(29) Z H(29) C(24) Y
H(33) O(33) Z H(33) C(33) Y
H(31A) C(31) Z H(31A) O(32) Y
H(31B) C(31) Z H(31B) O(32) Y
H(31C) C(31) Z H(31C) O(32) Y
H(33A) C(33) Z H(33A) O(33) Y
H(35) C(35) Z H(35) C(34) Y
H(36) C(36) Z H(36) C(35) Y
H(37) C(37) Z H(37) C(36) Y
H(38) C(38) Z H(38) C(37) Y
H(39) C(39) Z H(39) C(34) Y
H(43) O(43) Z H(43) C(43) Y
H(41A) C(41) Z H(41A) O(42) Y
H(41B) C(41) Z H(41B) O(42) Y
H(41C) C(41) Z H(41C) O(42) Y
H(43A) C(43) Z H(43A) O(43) Y
H(45) C(45) Z H(45) C(44) Y
H(46) C(46) Z H(46) C(45) Y
H(47) C(47) Z H(47) C(46) Y
H(48) C(48) Z H(48) C(47) Y
H(49) C(49) Z H(49) C(44) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(11) C(12) 1.202(2) 1_555 1_555 yes
O(12) C(12) 1.336(2) 1_555 1_555 yes
O(13) C(13) 1.407(2) 1_555 1_555 yes
O(13) H(13) 0.9607 1_555 1_555 yes
O(21) C(22) 1.203(2) 1_555 1_555 yes
O(22) C(22) 1.334(2) 1_555 1_555 yes
O(23) C(23) 1.406(2) 1_555 1_555 yes
O(23) H(23) 0.9607 1_555 1_555 yes
O(31) C(32) 1.206(2) 1_555 1_555 yes
O(32) C(32) 1.329(2) 1_555 1_555 yes
O(33) C(33) 1.414(2) 1_555 1_555 yes
O(33) H(33) 0.9607 1_555 1_555 yes
O(41) C(42) 1.212(3) 1_555 1_555 yes
O(42) C(42) 1.335(3) 1_555 1_555 yes
O(43) C(43) 1.420(3) 1_555 1_555 yes
O(43) H(43) 0.9607 1_555 1_555 yes
C(11) H(11A) 1.095 1_555 1_555 yes
C(11) H(11B) 1.095 1_555 1_555 yes
C(11) H(11C) 1.095 1_555 1_555 yes
C(12) C(13) 1.526(2) 1_555 1_555 yes
C(13) C(14) 1.527(3) 1_555 1_555 yes
C(13) H(13A) 1.098 1_555 1_555 yes
C(14) C(15) 1.392(3) 1_555 1_555 yes
C(14) C(19) 1.392(3) 1_555 1_555 yes
C(15) C(16) 1.394(3) 1_555 1_555 yes
C(15) H(15) 1.082 1_555 1_555 yes
C(16) C(17) 1.391(3) 1_555 1_555 yes
C(16) H(16) 1.082 1_555 1_555 yes
C(17) C(18) 1.393(3) 1_555 1_555 yes
C(17) H(17) 1.082 1_555 1_555 yes
C(18) C(19) 1.390(3) 1_555 1_555 yes
C(18) H(18) 1.082 1_555 1_555 yes
C(19) H(19) 1.082 1_555 1_555 yes
C(21) H(21A) 1.095 1_555 1_555 yes
C(21) H(21B) 1.095 1_555 1_555 yes
C(21) H(21C) 1.095 1_555 1_555 yes
C(22) C(23) 1.529(2) 1_555 1_555 yes
C(23) C(24) 1.522(3) 1_555 1_555 yes
C(23) H(23A) 1.098 1_555 1_555 yes
C(24) C(25) 1.395(3) 1_555 1_555 yes
C(24) C(29) 1.396(3) 1_555 1_555 yes
C(25) C(26) 1.394(3) 1_555 1_555 yes
C(25) H(25) 1.082 1_555 1_555 yes
C(26) C(27) 1.391(3) 1_555 1_555 yes
C(26) H(26) 1.082 1_555 1_555 yes
C(27) C(28) 1.392(3) 1_555 1_555 yes
C(27) H(27) 1.082 1_555 1_555 yes
C(28) C(29) 1.391(3) 1_555 1_555 yes
C(28) H(28) 1.082 1_555 1_555 yes
C(29) H(29) 1.082 1_555 1_555 yes
C(31) H(31A) 1.095 1_555 1_555 yes
C(31) H(31B) 1.095 1_555 1_555 yes
C(31) H(31C) 1.095 1_555 1_555 yes
C(32) C(33) 1.523(3) 1_555 1_555 yes
C(33) C(34) 1.518(3) 1_555 1_555 yes
C(33) H(33A) 1.098 1_555 1_555 yes
C(34) C(35) 1.389(3) 1_555 1_555 yes
C(34) C(39) 1.404(3) 1_555 1_555 yes
C(35) C(36) 1.377(3) 1_555 1_555 yes
C(35) H(35) 1.082 1_555 1_555 yes
C(36) C(37) 1.407(3) 1_555 1_555 yes
C(36) H(36) 1.082 1_555 1_555 yes
C(37) C(38) 1.397(3) 1_555 1_555 yes
C(37) H(37) 1.082 1_555 1_555 yes
C(38) C(39) 1.385(3) 1_555 1_555 yes
C(38) H(38) 1.082 1_555 1_555 yes
C(39) H(39) 1.082 1_555 1_555 yes
C(41) H(41A) 1.095 1_555 1_555 yes
C(41) H(41B) 1.095 1_555 1_555 yes
C(41) H(41C) 1.095 1_555 1_555 yes
C(42) C(43) 1.526(3) 1_555 1_555 yes
C(43) C(44) 1.518(3) 1_555 1_555 yes
C(43) H(43A) 1.098 1_555 1_555 yes
C(44) C(45) 1.399(2) 1_555 1_555 yes
C(44) C(49) 1.394(3) 1_555 1_555 yes
C(45) C(46) 1.387(3) 1_555 1_555 yes
C(45) H(45) 1.082 1_555 1_555 yes
C(46) C(47) 1.405(3) 1_555 1_555 yes
C(46) H(46) 1.082 1_555 1_555 yes
C(47) C(48) 1.392(3) 1_555 1_555 yes
C(47) H(47) 1.082 1_555 1_555 yes
C(48) C(49) 1.386(3) 1_555 1_555 yes
C(48) H(48) 1.082 1_555 1_555 yes
C(49) H(49) 1.082 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(11) C(12) O(12) 123.88(16) 1_555 1_555 1_555 yes
O(11) C(12) C(13) 124.81(16) 1_555 1_555 1_555 yes
O(12) C(12) C(13) 111.29(16) 1_555 1_555 1_555 yes
O(13) C(13) C(12) 105.76(14) 1_555 1_555 1_555 yes
O(13) C(13) C(14) 112.81(14) 1_555 1_555 1_555 yes
C(12) C(13) C(14) 108.85(17) 1_555 1_555 1_555 yes
C(13) C(14) C(15) 121.04(19) 1_555 1_555 1_555 yes
C(13) C(14) C(19) 119.48(17) 1_555 1_555 1_555 yes
C(15) C(14) C(19) 119.48(19) 1_555 1_555 1_555 yes
C(14) C(15) C(16) 120.0(2) 1_555 1_555 1_555 yes
C(15) C(16) C(17) 120.5(2) 1_555 1_555 1_555 yes
C(16) C(17) C(18) 119.3(2) 1_555 1_555 1_555 yes
C(17) C(18) C(19) 120.2(2) 1_555 1_555 1_555 yes
C(14) C(19) C(18) 120.41(19) 1_555 1_555 1_555 yes
O(21) C(22) O(22) 123.82(16) 1_555 1_555 1_555 yes
O(21) C(22) C(23) 124.59(17) 1_555 1_555 1_555 yes
O(22) C(22) C(23) 111.58(16) 1_555 1_555 1_555 yes
O(23) C(23) C(22) 105.92(15) 1_555 1_555 1_555 yes
O(23) C(23) C(24) 112.37(14) 1_555 1_555 1_555 yes
C(22) C(23) C(24) 110.02(17) 1_555 1_555 1_555 yes
C(23) C(24) C(25) 120.88(18) 1_555 1_555 1_555 yes
C(23) C(24) C(29) 120.07(17) 1_555 1_555 1_555 yes
C(25) C(24) C(29) 119.04(18) 1_555 1_555 1_555 yes
C(24) C(25) C(26) 120.28(19) 1_555 1_555 1_555 yes
C(25) C(26) C(27) 120.57(19) 1_555 1_555 1_555 yes
C(26) C(27) C(28) 119.20(19) 1_555 1_555 1_555 yes
C(27) C(28) C(29) 120.4(2) 1_555 1_555 1_555 yes
C(24) C(29) C(28) 120.50(19) 1_555 1_555 1_555 yes
O(31) C(32) O(32) 124.04(18) 1_555 1_555 1_555 yes
O(31) C(32) C(33) 124.44(16) 1_555 1_555 1_555 yes
O(32) C(32) C(33) 111.51(15) 1_555 1_555 1_555 yes
O(33) C(33) C(32) 106.58(14) 1_555 1_555 1_555 yes
O(33) C(33) C(34) 113.82(17) 1_555 1_555 1_555 yes
C(32) C(33) C(34) 108.61(16) 1_555 1_555 1_555 yes
C(33) C(34) C(35) 120.3(2) 1_555 1_555 1_555 yes
C(33) C(34) C(39) 120.43(16) 1_555 1_555 1_555 yes
C(35) C(34) C(39) 119.31(19) 1_555 1_555 1_555 yes
C(34) C(35) C(36) 120.8(2) 1_555 1_555 1_555 yes
C(35) C(36) C(37) 120.16(17) 1_555 1_555 1_555 yes
C(36) C(37) C(38) 119.33(19) 1_555 1_555 1_555 yes
C(37) C(38) C(39) 120.1(2) 1_555 1_555 1_555 yes
C(34) C(39) C(38) 120.35(17) 1_555 1_555 1_555 yes
O(41) C(42) O(42) 123.60(19) 1_555 1_555 1_555 yes
O(41) C(42) C(43) 124.9(2) 1_555 1_555 1_555 yes
O(42) C(42) C(43) 111.53(18) 1_555 1_555 1_555 yes
O(43) C(43) C(42) 106.08(17) 1_555 1_555 1_555 yes
O(43) C(43) C(44) 113.38(15) 1_555 1_555 1_555 yes
C(42) C(43) C(44) 110.69(16) 1_555 1_555 1_555 yes
C(43) C(44) C(45) 120.06(19) 1_555 1_555 1_555 yes
C(43) C(44) C(49) 120.28(15) 1_555 1_555 1_555 yes
C(45) C(44) C(49) 119.66(19) 1_555 1_555 1_555 yes
C(44) C(45) C(46) 120.6(2) 1_555 1_555 1_555 yes
C(45) C(46) C(47) 119.64(16) 1_555 1_555 1_555 yes
C(46) C(47) C(48) 119.4(2) 1_555 1_555 1_555 yes
C(47) C(48) C(49) 121.0(2) 1_555 1_555 1_555 yes
C(44) C(49) C(48) 119.70(16) 1_555 1_555 1_555 yes

# Attachment 's.cif'

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 2010-01-07 at 19:05:52
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.2
# Request file : /Local/xdbig/lib/xd/xdcif.dat
# CIF files read : fft geo lsm

#
#CHECKCIF gave the following B-alerts:
#PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
#Indeed the data completeness is not 100 % up to the Acta limit.
#Since the structure is monoclinic it was not possible
#to achieve full completeness with Cu Kalpha radiation in the given orientation
#with our measurement strategy.
#PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 -- C4 .. 7.57 su
#PLAT230_ALERT_2_B Hirshfeld Test Diff for C21 -- C26 .. 11.78 su
#The Hirshfeld test is not fulfilled for two bonds. The ADPs were
#freely refined without restraints, which are not implemented in the
#program XDLSM.

data_s_mm
_database_code_depnum_ccdc_archive 'CCDC 762620'
#TrackingRef 's.cif'

_audit_creation_date             2010-01-07T19:05:52-00:00
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_weight         166.17
_exptl_crystal_density_diffrn    1.2957
_chemical_absolute_configuration ad
_exptl_crystal_F_000             704.0
_chemical_compound_source        ' Sigma Aldrich '

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0191 0.0091 'Invariom modelling (Acta Cryst. A61, 314--320)'
H H 0.0000 0.0000 'Invariom modelling (Acta Cryst. A61, 314--320)'
O O 0.0522 0.0322 'Invariom modelling (Acta Cryst. A61, 314--320)'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,1/2+Y,-Z

_cell_length_a                   7.8825(4)
_cell_length_b                   20.1054(11)
_cell_length_c                   10.7516(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.033(3)
_cell_angle_gamma                90
_cell_volume                     1703.65(15)

_cell_measurement_reflns_used    7463
_cell_measurement_theta_min      4.1125
_cell_measurement_theta_max      70.95
_cell_measurement_temperature    100
_cell_formula_units_Z            8.0
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_cell_setting           monoclinic

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_min  0.5496
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS, multi-scan. (G. M. Sheldrick, 2008)
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_device_type  'Bruker SMART 6000 Diffractometer'
_diffrn_radiation_wavelength     1.54188
_diffrn_reflns_number            22455
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.1
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.95
_diffrn_reflns_theta_max         71.05
_diffrn_reflns_theta_full        67.7
_diffrn_orient_matrix_UB_11      -7.8924395e-02
_diffrn_orient_matrix_UB_12      3.8608845e-02
_diffrn_orient_matrix_UB_13      -1.0588609e-02
_diffrn_orient_matrix_UB_21      -9.7008310e-02
_diffrn_orient_matrix_UB_22      -3.1355303e-02
_diffrn_orient_matrix_UB_23      -1.3779531e-02
_diffrn_orient_matrix_UB_31      -2.1443270e-02
_diffrn_orient_matrix_UB_32      -2.5438517e-04
_diffrn_orient_matrix_UB_33      9.1386758e-02

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5259
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0488
_refine_ls_goodness_of_fit_ref   2.2645
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.061
_reflns_threshold_expression     F>3(\s)F
_reflns_number_total             5847
_reflns_number_gt                5259
_refine_ls_hydrogen_treatment    constr
_refine_ls_abs_structure_Flack   0.10(16)
_refine_ls_abs_structure_details 
;
An invariom refinement was performed (Dittrich, Acta Cryst. A62, 217)
to improve the standard uncertainty of the Flack parameter
(Flack, Acta Cryst, A39, 876) compared to an independent-atom refinement.
The standard uncertainty of the Flack parameter is too high for a
reliable assignment (Flack, J. Appl. Cryst. (2000). 33, 1143), but
since nuclei heavier than oxygen were not part of the structure, it was
decided to report the value nevertheless, since it can be at least
considered indicative.
;

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
O(1) 0.2599(2) 0.4309(2) 0.0349(2) 0.034 1
O(2) 0.1999(2) 0.33220(10) 0.19020(10) 0.033 1
O(3) 0.2385(3) 0.25690(10) 0.0394(2) 0.039 1
O(11) 0.2269(3) 0.42070(10) 0.5352(2) 0.044 1
O(12) 0.1485(3) 0.33740(10) 0.7124(2) 0.038 1
O(13) 0.2269(3) 0.24870(10) 0.6021(2) 0.043 1
O(21) 0.7755(2) -0.03640(10) 0.70550(10) 0.035 1
O(22) 0.7063(2) 0.06600(10) 0.55600(10) 0.038 1
O(23) 0.7428(3) 0.13730(10) 0.7142(2) 0.041 1
O(31) 0.7246(3) -0.01710(10) 0.2335(2) 0.043 1
O(32) 0.6710(2) 0.06160(10) 0.04290(10) 0.037 1
O(33) 0.7291(3) 0.15250(10) 0.1539(2) 0.039 1
C(1) 0.5030(3) 0.36230(10) -0.0151(2) 0.026 1
C(2) 0.6068(4) 0.3797(2) 0.0862(2) 0.035 1
C(3) 0.7810(4) 0.3788(2) 0.0764(2) 0.038 1
C(4) 0.8555(4) 0.3604(2) -0.0361(3) 0.045 1
C(5) 0.7520(4) 0.3424(2) -0.1365(2) 0.04 1
C(6) 0.5762(3) 0.3431(2) -0.1259(2) 0.035 1
C(7) 0.3114(3) 0.36780(10) -0.0067(2) 0.028 1
C(8) 0.2449(3) 0.31800(10) 0.0859(2) 0.027 1
C(11) 0.4571(3) 0.34400(10) 0.4851(2) 0.032 1
C(12) 0.5788(4) 0.3832(2) 0.5448(2) 0.042 1
C(13) 0.7486(4) 0.3754(2) 0.5195(3) 0.055 1
C(14) 0.7998(4) 0.3279(2) 0.4329(3) 0.057 1
C(15) 0.6781(4) 0.2880(2) 0.3746(2) 0.052 1
C(16) 0.5075(4) 0.2958(2) 0.4006(2) 0.04 1
C(17) 0.2687(4) 0.35440(10) 0.5086(2) 0.032 1
C(18) 0.2081(3) 0.3135(2) 0.6196(2) 0.031 1
C(21) 1.0141(3) 0.03380(10) 0.7670(2) 0.029 1
C(22) 1.0843(3) 0.0546(2) 0.8806(2) 0.032 1
C(23) 1.2570(4) 0.0584(2) 0.8988(2) 0.038 1
C(24) 1.3643(4) 0.0422(2) 0.8007(2) 0.039 1
C(25) 1.2953(4) 0.0213(2) 0.6869(2) 0.039 1
C(26) 1.1212(3) 0.0175(2) 0.6703(2) 0.031 1
C(27) 0.8232(3) 0.02640(10) 0.7520(2) 0.027 1
C(28) 0.7516(3) 0.0777(2) 0.6607(2) 0.032 1
C(31) 0.9656(3) 0.0561(2) 0.2765(2) 0.031 1
C(32) 1.0794(4) 0.0146(2) 0.2169(3) 0.044 1
C(33) 1.2519(4) 0.0196(2) 0.2419(3) 0.054 1
C(34) 1.3126(4) 0.0666(2) 0.3268(3) 0.058 1
C(35) 1.1992(4) 0.1087(2) 0.3858(3) 0.051 1
C(36) 1.0271(4) 0.1036(2) 0.3605(2) 0.039 1
C(37) 0.7761(3) 0.04870(10) 0.2534(2) 0.031 1
C(38) 0.7193(3) 0.0877(2) 0.1381(2) 0.029 1
C(40) 0.6817(4) 0.1924(2) 0.0467(3) 0.046 1
C(10) 0.1732(5) 0.2066(2) 0.1208(3) 0.05 1
C(20) 0.1750(5) 0.2069(2) 0.7044(3) 0.052 1
C(30) 0.6708(5) 0.1889(2) 0.6372(3) 0.057 1
H(1) 0.32433 0.46458 -0.00644 0.0513(6) 1
H(2) 0.55037 0.39306 0.17379 0.0423(8) 1
H(3) 0.86275 0.39242 0.15425 0.0458(8) 1
H(4) 0.99203 0.36033 -0.04485 0.0540(10) 1
H(5) 0.80775 0.32667 -0.22293 0.0478(8) 1
H(6) 0.49832 0.32841 -0.20515 0.0416(7) 1
H(7) 0.25355 0.35734 -0.0983 0.0335(7) 1
H(11) 0.22835 0.44666 0.46018 0.0660(8) 1
H(12) 0.54072 0.41992 0.61239 0.0508(9) 1
H(13) 0.84498 0.40533 0.56565 0.0660(10) 1
H(14) 0.93215 0.32197 0.41032 0.0690(10) 1
H(15) 0.71683 0.25085 0.30795 0.0620(10) 1
H(16) 0.41447 0.26388 0.35541 0.0475(8) 1
H(17) 0.19617 0.33844 0.42574 0.0388(7) 1
H(22) 1.00124 0.06749 0.95589 0.0380(7) 1
H(23) 1.31049 0.07362 0.98772 0.0459(8) 1
H(24) 1.5005 0.04454 0.81484 0.0471(8) 1
H(25) 1.37923 0.00783 0.61252 0.0468(8) 1
H(26) 1.07166 0.00158 0.58055 0.0375(7) 1
H(27) 0.76461 0.03334 0.84305 0.0320(6) 1
H(31) 0.7472 -0.04654 0.30218 0.0649(8) 1
H(32) 1.03292 -0.02212 0.15108 0.0523(9) 1
H(33) 1.33921 -0.01325 0.19532 0.0650(10) 1
H(34) 1.44798 0.06974 0.34449 0.0700(10) 1
H(35) 1.24698 0.14383 0.45422 0.0610(10) 1
H(36) 0.93864 0.13649 0.40567 0.0473(8) 1
H(37) 0.71035 0.06832 0.33478 0.0370(7) 1
H(40A) 0.7616 0.17902 -0.0316 0.0550(10) 1
H(40B) 0.69829 0.24526 0.06843 0.0550(10) 1
H(40C) 0.54904 0.18265 0.02091 0.0550(10) 1
H(10A) 0.26247 0.19889 0.19866 0.0598(9) 1
H(10B) 0.16199 0.15966 0.06971 0.0598(9) 1
H(10C) 0.04863 0.22114 0.15516 0.0598(9) 1
H(20A) 0.24706 0.21986 0.78899 0.0620(10) 1
H(20B) 0.19827 0.15443 0.68358 0.0620(10) 1
H(20C) 0.03976 0.21367 0.72191 0.0620(10) 1
H(30A) 0.75129 0.19574 0.55628 0.0680(10) 1
H(30B) 0.66423 0.2356 0.68919 0.0680(10) 1
H(30C) 0.54416 0.17416 0.60416 0.0680(10) 1
H(21) 0.77777 -0.07191 0.76537 0.0518(7) 1
#DUM0 0 0 0 0 0
#DUM1 0.31706 0.32326 0.22355 0 0
#DUM2 0.1991 0.26343 0.12572 0 0
#DUM3 0.26416 0.33923 0.7513 0 0
#DUM4 0.1796 0.26376 0.6827 0 0
#DUM5 0.82311 0.07597 0.52638 0 0
#DUM6 0.70131 0.13155 0.6268 0 0
#DUM7 0.79073 0.06046 0.01259 0 0
#DUM8 0.69063 0.1353 0.07117 0 0
#DUM9 0.65827 0.3661 0.00452 0 0
#DUM10 0.70763 0.36564 0.00214 0 0
#DUM11 0.7279 0.36 -0.02884 0 0
#DUM12 0.70003 0.35573 -0.05672 0 0
#DUM13 0.65035 0.35586 -0.05348 0 0
#DUM14 0.61378 0.34835 0.48221 0 0
#DUM15 0.66167 0.34623 0.47468 0 0
#DUM16 0.67647 0.3326 0.45198 0 0
#DUM17 0.64211 0.32209 0.43528 0 0
#DUM18 0.59375 0.3246 0.4423 0 0
#DUM19 1.15862 0.04171 0.81107 0 0
#DUM20 1.2085 0.0434 0.81649 0 0
#DUM21 1.23736 0.03857 0.78976 0 0
#DUM22 1.2184 0.03313 0.75801 0 0
#DUM23 1.16732 0.03146 0.75255 0 0
#DUM24 1.12158 0.04782 0.27829 0 0
#DUM25 1.16918 0.04937 0.28479 0 0
#DUM26 1.1862 0.06251 0.30917 0 0
#DUM27 1.15664 0.07433 0.32449 0 0
#DUM28 1.10822 0.07172 0.31844 0 0

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
O(1) 0.0410(10) 0.0320(10) 0.0290(10) 0.0010(10) 0.0030(10) 0.0050(10)
O(2) 0.0430(10) 0.0360(10) 0.0210(10) 0.0000(10) 0.0030(10) -0.0020(10)
O(3) 0.0480(10) 0.0360(10) 0.0330(10) -0.0040(10) 0.0030(10) -0.0030(10)
O(11) 0.068(2) 0.0370(10) 0.0270(10) 0.0050(10) 0.0060(10) 0.0110(10)
O(12) 0.0550(10) 0.0380(10) 0.0220(10) -0.0030(10) 0.0050(10) 0.0010(10)
O(13) 0.0570(10) 0.0380(10) 0.0330(10) 0.0000(10) 0.0120(10) -0.0020(10)
O(21) 0.0440(10) 0.0370(10) 0.0220(10) 0.0010(10) -0.0040(10) -0.0070(10)
O(22) 0.0490(10) 0.0440(10) 0.0210(10) 0.0020(10) -0.0060(10) 0.0030(10)
O(23) 0.0470(10) 0.0420(10) 0.0330(10) -0.0020(10) -0.0040(10) 0.0050(10)
O(31) 0.0540(10) 0.0410(10) 0.0340(10) 0.0080(10) -0.0090(10) -0.0120(10)
O(32) 0.0540(10) 0.0350(10) 0.0200(10) -0.0040(10) -0.0070(10) 0.0030(10)
O(33) 0.0530(10) 0.0340(10) 0.0300(10) -0.0020(10) -0.0090(10) 0.0020(10)
C(1) 0.0280(10) 0.0340(10) 0.0170(10) 0.0010(10) 0.0030(10) 0.0010(10)
C(2) 0.038(2) 0.0350(10) 0.0320(10) -0.0020(10) -0.0110(10) -0.0050(10)
C(3) 0.038(2) 0.045(2) 0.0310(10) 0.0040(10) -0.0060(10) -0.0060(10)
C(4) 0.035(2) 0.053(2) 0.048(2) 0.0150(10) -0.0090(10) -0.0040(10)
C(5) 0.030(2) 0.062(2) 0.0270(10) 0.0050(10) 0.0070(10) 0.0020(10)
C(6) 0.033(2) 0.047(2) 0.0240(10) 0.0000(10) 0.0000(10) 0.0050(10)
C(7) 0.0320(10) 0.0360(10) 0.0160(10) -0.0010(10) 0.0010(10) -0.0010(10)
C(8) 0.0290(10) 0.0370(10) 0.0160(10) -0.0020(10) 0.0030(10) 0.0030(10)
C(11) 0.039(2) 0.0360(10) 0.0210(10) 0.0040(10) -0.0040(10) -0.0030(10)
C(12) 0.048(2) 0.045(2) 0.0340(10) 0.0060(10) -0.0090(10) -0.0120(10)
C(13) 0.048(2) 0.068(2) 0.048(2) 0.019(2) -0.012(2) -0.020(2)
C(14) 0.032(2) 0.102(3) 0.038(2) 0.025(2) 0.0030(10) -0.001(2)
C(15) 0.046(2) 0.082(2) 0.027(2) 0.0050(10) 0.0000(10) 0.016(2)
C(16) 0.043(2) 0.050(2) 0.0250(10) -0.0020(10) -0.0060(10) 0.0050(10)
C(17) 0.042(2) 0.036(2) 0.0180(10) 0.0020(10) -0.0030(10) 0.0010(10)
C(18) 0.038(2) 0.0330(10) 0.0230(10) -0.0020(10) -0.0050(10) 0.0020(10)
C(21) 0.0310(10) 0.0320(10) 0.0240(10) 0.0020(10) -0.0030(10) -0.0010(10)
C(22) 0.0310(10) 0.0450(10) 0.0190(10) -0.0040(10) 0.0020(10) 0.0000(10)
C(23) 0.033(2) 0.055(2) 0.0270(10) -0.0050(10) -0.0030(10) -0.0020(10)
C(24) 0.029(2) 0.053(2) 0.035(2) 0.0030(10) -0.0010(10) 0.0000(10)
C(25) 0.035(2) 0.050(2) 0.0320(10) 0.0010(10) 0.0020(10) 0.0020(10)
C(26) 0.037(2) 0.0440(10) 0.0120(10) -0.0020(10) 0.0110(10) 0.0040(10)
C(27) 0.0280(10) 0.0380(10) 0.0140(10) 0.0010(10) 0.0050(10) 0.0000(10)
C(28) 0.0350(10) 0.038(2) 0.0220(10) 0.0000(10) -0.0020(10) -0.0010(10)
C(31) 0.038(2) 0.0360(10) 0.0210(10) 0.0040(10) 0.0000(10) -0.0010(10)
C(32) 0.050(2) 0.041(2) 0.040(2) 0.0020(10) 0.0030(10) 0.0110(10)
C(33) 0.045(2) 0.067(2) 0.051(2) 0.021(2) 0.019(2) 0.021(2)
C(34) 0.037(2) 0.088(3) 0.049(2) 0.029(2) -0.007(2) -0.003(2)
C(35) 0.040(2) 0.082(2) 0.029(2) 0.0090(10) -0.0040(10) -0.015(2)
C(36) 0.039(2) 0.052(2) 0.0260(10) -0.0010(10) -0.0030(10) -0.0100(10)
C(37) 0.038(2) 0.0360(10) 0.0190(10) 0.0020(10) -0.0010(10) -0.0010(10)
C(38) 0.0320(10) 0.0340(10) 0.0220(10) 0.0010(10) -0.0010(10) 0.0010(10)
C(40) 0.063(2) 0.036(2) 0.038(2) 0.0030(10) -0.0110(10) 0.0080(10)
C(10) 0.060(2) 0.040(2) 0.050(2) -0.0020(10) 0.014(2) -0.0080(10)
C(20) 0.072(2) 0.037(2) 0.047(2) 0.0050(10) 0.014(2) -0.008(2)
C(30) 0.073(3) 0.041(2) 0.056(2) 0.0020(10) -0.013(2) 0.015(2)

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(7) X O(1) H(1) Y
O(2) DUM1 Z O(2) C(8) Y
O(3) DUM2 Z O(3) C(8) Y
O(11) C(17) X O(11) H(11) Y
O(12) DUM3 Z O(12) C(18) Y
O(13) DUM4 Z O(13) C(18) Y
O(21) C(27) X O(21) H(21) Y
O(22) DUM5 Z O(22) C(28) Y
O(23) DUM6 Z O(23) C(28) Y
O(31) C(37) X O(31) H(31) Y
O(32) DUM7 Z O(32) C(38) Y
O(33) DUM8 Z O(33) C(38) Y
C(1) C(2) Z C(1) C(6) Y
C(2) DUM9 Z C(2) C(1) Y
C(3) DUM10 Z C(3) C(2) Y
C(4) DUM11 Z C(4) C(3) Y
C(5) DUM12 Z C(5) C(4) Y
C(6) DUM13 Z C(6) C(1) Y
C(7) O(1) X C(7) C(1) Y
C(8) O(2) X C(8) O(3) Y
C(11) C(12) Z C(11) C(16) Y
C(12) DUM14 Z C(12) C(11) Y
C(13) DUM15 Z C(13) C(12) Y
C(14) DUM16 Z C(14) C(13) Y
C(15) DUM17 Z C(15) C(14) Y
C(16) DUM18 Z C(16) C(11) Y
C(17) O(11) X C(17) C(11) Y
C(18) O(12) X C(18) O(13) Y
C(21) C(22) Z C(21) C(26) Y
C(22) DUM19 Z C(22) C(21) Y
C(23) DUM20 Z C(23) C(22) Y
C(24) DUM21 Z C(24) C(23) Y
C(25) DUM22 Z C(25) C(24) Y
C(26) DUM23 Z C(26) C(21) Y
C(27) O(21) X C(27) C(21) Y
C(28) O(22) X C(28) O(23) Y
C(31) C(32) Z C(31) C(36) Y
C(32) DUM24 Z C(32) C(31) Y
C(33) DUM25 Z C(33) C(32) Y
C(34) DUM26 Z C(34) C(33) Y
C(35) DUM27 Z C(35) C(34) Y
C(36) DUM28 Z C(36) C(31) Y
C(37) O(31) X C(37) C(31) Y
C(38) O(32) X C(38) O(33) Y
C(40) O(33) Z C(40) H(40A) Y
C(10) O(3) Z C(10) H(10A) Y
C(20) O(13) Z C(20) H(20A) Y
C(30) O(23) Z C(30) H(30A) Y
H(1) O(1) Z H(1) C(7) Y
H(2) C(2) Z H(2) C(1) Y
H(3) C(3) Z H(3) C(2) Y
H(4) C(4) Z H(4) C(3) Y
H(5) C(5) Z H(5) C(4) Y
H(6) C(6) Z H(6) C(1) Y
H(7) C(7) Z H(7) O(1) Y
H(11) O(11) Z H(11) C(17) Y
H(12) C(12) Z H(12) C(11) Y
H(13) C(13) Z H(13) C(12) Y
H(14) C(14) Z H(14) C(13) Y
H(15) C(15) Z H(15) C(14) Y
H(16) C(16) Z H(16) C(11) Y
H(17) C(17) Z H(17) O(11) Y
H(22) C(22) Z H(22) C(21) Y
H(23) C(23) Z H(23) C(22) Y
H(24) C(24) Z H(24) C(23) Y
H(25) C(25) Z H(25) C(24) Y
H(26) C(26) Z H(26) C(21) Y
H(27) C(27) Z H(27) O(21) Y
H(31) O(31) Z H(31) C(37) Y
H(32) C(32) Z H(32) C(31) Y
H(33) C(33) Z H(33) C(32) Y
H(34) C(34) Z H(34) C(33) Y
H(35) C(35) Z H(35) C(34) Y
H(36) C(36) Z H(36) C(31) Y
H(37) C(37) Z H(37) O(31) Y
H(40A) C(40) Z H(40A) O(33) Y
H(40B) C(40) Z H(40B) O(33) Y
H(40C) C(40) Z H(40C) O(33) Y
H(10A) C(10) Z H(10A) O(3) Y
H(10B) C(10) Z H(10B) O(3) Y
H(10C) C(10) Z H(10C) O(3) Y
H(20A) C(20) Z H(20A) O(13) Y
H(20B) C(20) Z H(20B) O(13) Y
H(20C) C(20) Z H(20C) O(13) Y
H(30A) C(30) Z H(30A) O(23) Y
H(30B) C(30) Z H(30B) O(23) Y
H(30C) C(30) Z H(30C) O(23) Y
H(21) O(21) Z H(21) C(27) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(7) 1.407(3) 1_555 1_555 yes
O(1) H(1) 0.9607 1_555 1_555 yes
O(2) C(8) 1.216(3) 1_555 1_555 yes
O(3) C(8) 1.325(3) 1_555 1_555 yes
O(11) C(17) 1.405(3) 1_555 1_555 yes
O(11) H(11) 0.961 1_555 1_555 yes
O(12) C(18) 1.210(3) 1_555 1_555 yes
O(13) C(18) 1.325(3) 1_555 1_555 yes
O(21) C(27) 1.408(3) 1_555 1_555 yes
O(21) H(21) 0.9607 1_555 1_555 yes
O(22) C(28) 1.197(3) 1_555 1_555 yes
O(23) C(28) 1.333(3) 1_555 1_555 yes
O(31) C(37) 1.399(3) 1_555 1_555 yes
O(31) H(31) 0.961 1_555 1_555 yes
O(32) C(38) 1.206(3) 1_555 1_555 yes
O(33) C(38) 1.317(3) 1_555 1_555 yes
C(1) C(2) 1.396(3) 1_555 1_555 yes
C(1) C(6) 1.387(4) 1_555 1_555 yes
C(1) C(7) 1.519(4) 1_555 1_555 yes
C(2) C(3) 1.379(4) 1_555 1_555 yes
C(2) H(2) 1.082 1_555 1_555 yes
C(3) C(4) 1.404(5) 1_555 1_555 yes
C(3) H(3) 1.082 1_555 1_555 yes
C(4) C(5) 1.389(3) 1_555 1_555 yes
C(4) H(4) 1.082 1_555 1_555 yes
C(5) C(6) 1.393(4) 1_555 1_555 yes
C(5) H(5) 1.082 1_555 1_555 yes
C(6) H(6) 1.082 1_555 1_555 yes
C(7) C(8) 1.513(3) 1_555 1_555 yes
C(7) H(7) 1.0982 1_555 1_555 yes
C(11) C(12) 1.389(3) 1_555 1_555 yes
C(11) C(16) 1.392(4) 1_555 1_555 yes
C(11) C(17) 1.525(4) 1_555 1_555 yes
C(12) C(13) 1.380(5) 1_555 1_555 yes
C(12) H(12) 1.082 1_555 1_555 yes
C(13) C(14) 1.398(5) 1_555 1_555 yes
C(13) H(13) 1.082 1_555 1_555 yes
C(14) C(15) 1.392(5) 1_555 1_555 yes
C(14) H(14) 1.082 1_555 1_555 yes
C(15) C(16) 1.387(4) 1_555 1_555 yes
C(15) H(15) 1.082 1_555 1_555 yes
C(16) H(16) 1.082 1_555 1_555 yes
C(17) C(18) 1.532(4) 1_555 1_555 yes
C(17) H(17) 1.098 1_555 1_555 yes
C(21) C(22) 1.396(3) 1_555 1_555 yes
C(21) C(26) 1.390(4) 1_555 1_555 yes
C(21) C(27) 1.518(3) 1_555 1_555 yes
C(22) C(23) 1.373(4) 1_555 1_555 yes
C(22) H(22) 1.082 1_555 1_555 yes
C(23) C(24) 1.402(4) 1_555 1_555 yes
C(23) H(23) 1.082 1_555 1_555 yes
C(24) C(25) 1.395(3) 1_555 1_555 yes
C(24) H(24) 1.082 1_555 1_555 yes
C(25) C(26) 1.383(4) 1_555 1_555 yes
C(25) H(25) 1.082 1_555 1_555 yes
C(26) H(26) 1.082 1_555 1_555 yes
C(27) C(28) 1.525(3) 1_555 1_555 yes
C(27) H(27) 1.098 1_555 1_555 yes
C(31) C(32) 1.389(4) 1_555 1_555 yes
C(31) C(36) 1.396(3) 1_555 1_555 yes
C(31) C(37) 1.517(4) 1_555 1_555 yes
C(32) C(33) 1.385(4) 1_555 1_555 yes
C(32) H(32) 1.082 1_555 1_555 yes
C(33) C(34) 1.393(5) 1_555 1_555 yes
C(33) H(33) 1.082 1_555 1_555 yes
C(34) C(35) 1.393(5) 1_555 1_555 yes
C(34) H(34) 1.082 1_555 1_555 yes
C(35) C(36) 1.382(4) 1_555 1_555 yes
C(35) H(35) 1.082 1_555 1_555 yes
C(36) H(36) 1.082 1_555 1_555 yes
C(37) C(38) 1.526(3) 1_555 1_555 yes
C(37) H(37) 1.098 1_555 1_555 yes
C(40) H(40A) 1.095 1_555 1_555 yes
C(40) H(40B) 1.095 1_555 1_555 yes
C(40) H(40C) 1.095 1_555 1_555 yes
C(10) H(10A) 1.095 1_555 1_555 yes
C(10) H(10B) 1.095 1_555 1_555 yes
C(10) H(10C) 1.095 1_555 1_555 yes
C(20) H(20A) 1.095 1_555 1_555 yes
C(20) H(20B) 1.095 1_555 1_555 yes
C(20) H(20C) 1.095 1_555 1_555 yes
C(30) H(30A) 1.095 1_555 1_555 yes
C(30) H(30B) 1.095 1_555 1_555 yes
C(30) H(30C) 1.095 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(2) C(1) C(6) 119.6(2) 1_555 1_555 1_555 yes
C(2) C(1) C(7) 120.3(2) 1_555 1_555 1_555 yes
C(6) C(1) C(7) 120.08(18) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 120.5(3) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 120.1(2) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.3(3) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 120.3(3) 1_555 1_555 1_555 yes
C(1) C(6) C(5) 120.2(2) 1_555 1_555 1_555 yes
O(1) C(7) C(1) 112.22(19) 1_555 1_555 1_555 yes
O(1) C(7) C(8) 106.4(2) 1_555 1_555 1_555 yes
C(1) C(7) C(8) 110.32(18) 1_555 1_555 1_555 yes
O(2) C(8) O(3) 123.8(2) 1_555 1_555 1_555 yes
O(2) C(8) C(7) 124.1(2) 1_555 1_555 1_555 yes
O(3) C(8) C(7) 112.1(2) 1_555 1_555 1_555 yes
C(12) C(11) C(16) 119.6(3) 1_555 1_555 1_555 yes
C(12) C(11) C(17) 120.8(3) 1_555 1_555 1_555 yes
C(16) C(11) C(17) 119.6(2) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 120.6(3) 1_555 1_555 1_555 yes
C(12) C(13) C(14) 120.1(3) 1_555 1_555 1_555 yes
C(13) C(14) C(15) 119.3(3) 1_555 1_555 1_555 yes
C(14) C(15) C(16) 120.5(3) 1_555 1_555 1_555 yes
C(11) C(16) C(15) 120.0(2) 1_555 1_555 1_555 yes
O(11) C(17) C(11) 113.4(2) 1_555 1_555 1_555 yes
O(11) C(17) C(18) 105.9(2) 1_555 1_555 1_555 yes
C(11) C(17) C(18) 111.98(18) 1_555 1_555 1_555 yes
O(12) C(18) O(13) 123.6(3) 1_555 1_555 1_555 yes
O(12) C(18) C(17) 124.0(2) 1_555 1_555 1_555 yes
O(13) C(18) C(17) 112.4(2) 1_555 1_555 1_555 yes
C(22) C(21) C(26) 119.3(2) 1_555 1_555 1_555 yes
C(22) C(21) C(27) 119.9(2) 1_555 1_555 1_555 yes
C(26) C(21) C(27) 120.77(19) 1_555 1_555 1_555 yes
C(21) C(22) C(23) 121.2(3) 1_555 1_555 1_555 yes
C(22) C(23) C(24) 119.3(2) 1_555 1_555 1_555 yes
C(23) C(24) C(25) 119.9(3) 1_555 1_555 1_555 yes
C(24) C(25) C(26) 120.1(3) 1_555 1_555 1_555 yes
C(21) C(26) C(25) 120.3(2) 1_555 1_555 1_555 yes
O(21) C(27) C(21) 112.5(2) 1_555 1_555 1_555 yes
O(21) C(27) C(28) 106.50(16) 1_555 1_555 1_555 yes
C(21) C(27) C(28) 110.9(2) 1_555 1_555 1_555 yes
O(22) C(28) O(23) 124.4(2) 1_555 1_555 1_555 yes
O(22) C(28) C(27) 125.0(2) 1_555 1_555 1_555 yes
O(23) C(28) C(27) 110.55(19) 1_555 1_555 1_555 yes
C(32) C(31) C(36) 119.3(3) 1_555 1_555 1_555 yes
C(32) C(31) C(37) 120.6(2) 1_555 1_555 1_555 yes
C(36) C(31) C(37) 120.1(3) 1_555 1_555 1_555 yes
C(31) C(32) C(33) 120.5(3) 1_555 1_555 1_555 yes
C(32) C(33) C(34) 120.0(3) 1_555 1_555 1_555 yes
C(33) C(34) C(35) 119.7(3) 1_555 1_555 1_555 yes
C(34) C(35) C(36) 120.0(3) 1_555 1_555 1_555 yes
C(31) C(36) C(35) 120.4(3) 1_555 1_555 1_555 yes
O(31) C(37) C(31) 113.5(2) 1_555 1_555 1_555 yes
O(31) C(37) C(38) 106.32(17) 1_555 1_555 1_555 yes
C(31) C(37) C(38) 110.9(2) 1_555 1_555 1_555 yes
O(32) C(38) O(33) 123.8(2) 1_555 1_555 1_555 yes
O(32) C(38) C(37) 123.3(2) 1_555 1_555 1_555 yes
O(33) C(38) C(37) 112.81(19) 1_555 1_555 1_555 yes


# Attachment 'rrrs.cif'

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 2010-01-06 at 18:45:29
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.2
# Request file : /Local/xdbig/lib/xd/xdcif.dat
# CIF files read : fft geo lsm

#
#CHECKCIF gave the following B-alerts:
#Deviating Methyl C19 H-C-H Bond Angle ...... 96.00 Deg.
#PLAT413_ALERT_2_B Short Inter XH3 .. XHn H13 .. H29C .. 2.06 Ang.
# A hydrogen atom H-X-H angles deviates from ideal values.
# Positional parameters of hydrogen atoms were elongated to
# be close to values from neutron diffraction, but not H-X-H angles.
# Such a feature is not implemented in the program XDLSM.
# Elongation also probably causes the short interatomic H-H distance.

data_rrrs
_database_code_depnum_ccdc_archive 'CCDC 762621'
#TrackingRef 'rrrs.cif'

_audit_creation_date             2010-01-06T18:45:29-00:00
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_weight         166.17
_exptl_crystal_density_diffrn    1.3309
_chemical_absolute_configuration ad
_exptl_crystal_F_000             704.0
_chemical_compound_source        ' Sigma Aldrich '

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0191 0.0091 'Invariom modelling (Acta Cryst. A61, 314--320)'
H H 0.0000 0.0000 'Invariom modelling (Acta Cryst. A61, 314--320)'
O O 0.0522 0.0322 'Invariom modelling (Acta Cryst. A61, 314--320)'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,1/2+Y,-Z

_cell_length_a                   11.0955(9)
_cell_length_b                   7.8081(5)
_cell_length_c                   19.7538(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.259(5)
_cell_angle_gamma                90
_cell_volume                     1658.6(2)

_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      2.308
_cell_measurement_theta_max      72.25
_cell_measurement_temperature    100
_cell_formula_units_Z            8.0
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_cell_setting           monoclinic

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS, multi-scan. (G. M. Sheldrick, 2008)
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_device_type  'Bruker SMART 6000 Diffractometer'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_number            27403
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         73.96
_diffrn_reflns_theta_full        72.97
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.957
_diffrn_orient_matrix_UB_11      -7.2907223e-03
_diffrn_orient_matrix_UB_12      1.7419652e-03
_diffrn_orient_matrix_UB_13      4.9453922e-02
_diffrn_orient_matrix_UB_21      9.0015739e-02
_diffrn_orient_matrix_UB_22      3.0755922e-02
_diffrn_orient_matrix_UB_23      1.6141847e-02
_diffrn_orient_matrix_UB_31      -2.2168536e-02
_diffrn_orient_matrix_UB_32      1.2431208e-01
_diffrn_orient_matrix_UB_33      -4.6866275e-03

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4538
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0264
_refine_ls_goodness_of_fit_ref   1.9895
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_reflns_threshold_expression     F>3(\s)F
_reflns_number_total             5618
_reflns_number_gt                4538
_refine_ls_hydrogen_treatment    constr
_refine_ls_abs_structure_Flack   0.10(15)
_refine_ls_abs_structure_details 
;
An invariom refinement was performed (Dittrich, Acta Cryst. A62, 217)
to improve the standard uncertainty of the Flack parameter
(Flack, Acta Cryst, A39, 876) compared to an independent-atom refinement.
The standard uncertainty of the Flack parameter is too high for a
reliable assignment (Flack, J. Appl. Cryst. (2000). 33, 1143), but
since nuclei heavier than oxygen were not part of the structure, it was
decided to report the value nevertheless, since it can be at leas
considered indicative.
;

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
O(1) 0.8125(2) 0.3211(3) 0.29190(10) 0.026 1
O(2) 1.02660(10) 0.3244(3) 0.38600(10) 0.03 1
O(3) 0.94180(10) 0.4336(3) 0.46810(10) 0.03 1
O(11) 1.0510(2) 0.2934(2) 0.25040(10) 0.028 1
O(12) 1.15520(10) 0.4085(2) 0.15370(10) 0.033 1
O(13) 0.97610(10) 0.3998(2) 0.07180(10) 0.038 1
O(21) 0.5422(2) 0.3224(2) 0.24530(10) 0.031 1
O(22) 0.65830(10) 0.4074(2) 0.14980(10) 0.028 1
O(23) 0.48140(10) 0.4131(2) 0.06600(10) 0.032 1
O(31) 0.31760(10) 0.2779(2) 0.29540(10) 0.025 1
O(32) 0.53420(10) 0.2572(3) 0.38720(10) 0.029 1
O(33) 0.44780(10) 0.1560(2) 0.47020(10) 0.029 1
C(1) 0.7702(2) 0.5830(3) 0.34980(10) 0.02 1
C(2) 0.8228(2) 0.6933(3) 0.30990(10) 0.024 1
C(3) 0.7912(2) 0.8659(3) 0.30540(10) 0.026 1
C(4) 0.7050(2) 0.9281(3) 0.34010(10) 0.026 1
C(5) 0.6522(2) 0.8171(3) 0.37950(10) 0.027 1
C(6) 0.6850(2) 0.6443(3) 0.38520(10) 0.026 1
C(7) 0.8075(2) 0.3949(3) 0.35600(10) 0.021 1
C(8) 0.9371(2) 0.3785(3) 0.40360(10) 0.022 1
C(9) 1.0625(2) 0.4300(4) 0.51630(10) 0.032 1
C(11) 0.9349(2) 0.1057(3) 0.15870(10) 0.021 1
C(12) 0.8213(2) 0.0750(3) 0.11290(10) 0.032 1
C(13) 0.7839(2) -0.0919(3) 0.09350(10) 0.04 1
C(14) 0.8606(2) -0.2290(3) 0.12050(10) 0.033 1
C(15) 0.9749(3) -0.1978(3) 0.1650(2) 0.031 1
C(16) 1.0123(2) -0.0307(3) 0.18450(10) 0.027 1
C(17) 0.9741(2) 0.2879(3) 0.18270(10) 0.023 1
C(18) 1.0473(2) 0.3711(3) 0.13550(10) 0.025 1
C(19) 1.0360(3) 0.4860(4) 0.02520(10) 0.056 1
C(21) 0.4369(2) 0.1191(3) 0.15640(10) 0.023 1
C(22) 0.3173(2) 0.0728(3) 0.12270(10) 0.037 1
C(23) 0.2868(2) -0.0983(3) 0.10970(10) 0.046 1
C(24) 0.3768(3) -0.2244(3) 0.1295(2) 0.041 1
C(25) 0.4977(3) -0.1781(3) 0.1628(2) 0.036 1
C(26) 0.5271(2) -0.0059(3) 0.17560(10) 0.028 1
C(27) 0.4700(2) 0.3049(3) 0.17620(10) 0.022 1
C(28) 0.5487(2) 0.3800(3) 0.13030(10) 0.022 1
C(29) 0.5492(2) 0.4929(3) 0.02080(10) 0.044 1
C(31) 0.2728(2) 0.0120(3) 0.35000(10) 0.019 1
C(32) 0.1866(2) -0.0495(3) 0.38410(10) 0.024 1
C(33) 0.1487(2) -0.2198(3) 0.37580(10) 0.027 1
C(34) 0.1961(2) -0.3282(3) 0.33320(10) 0.027 1
C(35) 0.2834(2) -0.2664(3) 0.29930(10) 0.027 1
C(36) 0.3217(2) -0.0964(3) 0.30760(10) 0.023 1
C(37) 0.3140(2) 0.1982(3) 0.35860(10) 0.021 1
C(38) 0.4446(2) 0.2087(3) 0.40590(10) 0.022 1
C(39) 0.5678(2) 0.1579(3) 0.51840(10) 0.032 1
H(1) 0.72987 0.32929 0.26228 0.0379(6) 1
H(2) 0.88958 0.63567 0.28509 0.0273(6) 1
H(3) 0.83585 0.95133 0.27601 0.0303(6) 1
H(4) 0.68293 1.0632 0.33491 0.0313(6) 1
H(5) 0.58103 0.85988 0.40448 0.0314(7) 1
H(6) 0.64167 0.56422 0.41716 0.0296(6) 1
H(7) 0.74588 0.32304 0.38151 0.0239(5) 1
H(9A) 1.13178 0.50366 0.49757 0.0379(6) 1
H(9B) 1.08905 0.29524 0.52507 0.0379(6) 1
H(9C) 1.04718 0.49745 0.56202 0.0379(6) 1
H(11) 0.99964 0.28771 0.28306 0.0408(7) 1
H(12) 0.76088 0.18171 0.09268 0.0387(6) 1
H(13) 0.69625 -0.11614 0.05631 0.0481(7) 1
H(14) 0.83657 -0.3572 0.10096 0.0382(7) 1
H(15) 1.02623 -0.31041 0.18755 0.0370(8) 1
H(16) 1.10099 -0.01778 0.22219 0.0325(6) 1
H(17) 0.88993 0.36595 0.17739 0.0263(7) 1
H(19A) 1.11093 0.41252 0.01182 0.0654(9) 1
H(19B) 1.07597 0.60958 0.04535 0.0654(9) 1
H(19C) 0.97427 0.48398 -0.02737 0.0654(9) 1
H(21) 0.49026 0.30575 0.27713 0.0445(6) 1
H(22) 0.25004 0.17545 0.10926 0.0430(7) 1
H(23) 0.19392 -0.13709 0.08235 0.0533(7) 1
H(24) 0.35492 -0.35828 0.11865 0.0468(8) 1
H(25) 0.56795 -0.27565 0.17969 0.0424(8) 1
H(26) 0.62152 0.02835 0.20199 0.0330(6) 1
H(27) 0.38191 0.37579 0.16634 0.0257(7) 1
H(29A) 0.62824 0.41386 0.0161 0.0519(7) 1
H(29B) 0.58821 0.6192 0.03751 0.0519(7) 1
H(29C) 0.47707 0.49563 -0.02831 0.0519(7) 1
H(32) 0.151 0.03593 0.41779 0.0282(6) 1
H(33) 0.07989 -0.26681 0.40172 0.0314(7) 1
H(34) 0.16538 -0.45965 0.32406 0.0316(6) 1
H(35) 0.31806 -0.36082 0.26865 0.0320(6) 1
H(36) 0.38736 -0.05036 0.27936 0.0263(6) 1
H(37) 0.25388 0.26433 0.38681 0.0248(6) 1
H(39A) 0.6073 0.28704 0.52238 0.0383(7) 1
H(39B) 0.63135 0.07399 0.49938 0.0383(7) 1
H(39C) 0.56013 0.11529 0.57001 0.0383(7) 1
H(31) 0.23605 0.28913 0.26481 0.0366(6) 1
#DUM0 0 0 0 0 0
#DUM1 1.00811 0.20591 0.39988 0 0
#DUM2 1.01979 0.39397 0.45728 0 0
#DUM3 1.13282 0.52396 0.16879 0 0
#DUM4 1.06443 0.43758 0.08335 0 0
#DUM5 0.64085 0.52556 0.16453 0 0
#DUM6 0.57142 0.44344 0.07881 0 0
#DUM7 0.54998 0.13739 0.37379 0 0
#DUM8 0.52673 0.19261 0.45961 0 0
#DUM9 0.76265 0.7373 0.33568 0 0
#DUM10 0.75169 0.78551 0.33362 0 0
#DUM11 0.7287 0.80349 0.34382 0 0
#DUM12 0.71433 0.77261 0.35496 0 0
#DUM13 0.72269 0.72339 0.35599 0 0
#DUM14 0.87758 -0.02433 0.13241 0 0
#DUM15 0.86701 -0.07034 0.12746 0 0
#DUM16 0.88746 -0.10769 0.13325 0 0
#DUM17 0.9187 -0.09781 0.14671 0 0
#DUM18 0.92854 -0.0528 0.1517 0 0
#DUM19 0.38275 -0.018 0.13812 0 0
#DUM20 0.37518 -0.0647 0.13373 0 0
#DUM21 0.39899 -0.09965 0.13933 0 0
#DUM22 0.43194 -0.08631 0.14812 0 0
#DUM23 0.43937 -0.03993 0.15229 0 0
#DUM24 0.22129 -0.12752 0.35342 0 0
#DUM25 0.21051 -0.17452 0.35104 0 0
#DUM26 0.22467 -0.20496 0.33939 0 0
#DUM27 0.24821 -0.18822 0.3298 0 0
#DUM28 0.25853 -0.14027 0.33208 0 0

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
O(1) 0.0246(9) 0.0212(8) 0.0298(11) -0.0061(6) 0.0066(8) 0.0016(6)
O(2) 0.0199(8) 0.0410(9) 0.0272(11) -0.0014(7) 0.0067(8) 0.0111(6)
O(3) 0.0252(7) 0.0365(9) 0.0257(10) 0.0022(7) 0.0069(7) 0.0057(7)
O(11) 0.0255(9) 0.0299(10) 0.0268(11) -0.0065(6) 0.0080(8) -0.0034(5)
O(12) 0.0248(7) 0.0330(8) 0.0415(10) 0.0047(6) 0.0136(7) 0.0009(6)
O(13) 0.0529(9) 0.0277(8) 0.0294(9) 0.0010(6) 0.0039(7) -0.0092(7)
O(21) 0.0340(10) 0.0330(10) 0.0240(10) -0.0050(10) 0.0110(10) -0.0070(10)
O(22) 0.0226(7) 0.0313(7) 0.0292(9) 0.0039(6) 0.0083(6) -0.0003(6)
O(23) 0.0384(8) 0.0286(8) 0.0263(9) 0.0030(6) 0.0011(7) -0.0079(6)
O(31) 0.0243(9) 0.0195(8) 0.0294(11) 0.0023(6) 0.0067(8) -0.0011(6)
O(32) 0.0198(8) 0.0374(8) 0.0292(11) 0.0015(7) 0.0105(7) -0.0071(7)
O(33) 0.0239(7) 0.0382(9) 0.0250(10) -0.0021(7) 0.0072(7) -0.0067(6)
C(1) 0.0190(10) 0.0130(10) 0.0280(10) -0.0010(10) 0.0070(10) 0.0020(10)
C(2) 0.0230(10) 0.0210(10) 0.0270(10) 0.0000(10) 0.0090(10) 0.0010(10)
C(3) 0.0270(10) 0.0200(10) 0.0280(10) 0.0050(10) 0.0070(10) 0.0000(10)
C(4) 0.0260(10) 0.0190(10) 0.0310(10) 0.0020(10) 0.0030(10) 0.0030(10)
C(5) 0.0240(10) 0.0210(10) 0.036(2) -0.0020(10) 0.0110(10) 0.0030(10)
C(6) 0.0220(10) 0.0200(10) 0.0350(10) -0.0020(10) 0.0130(10) 0.0010(10)
C(7) 0.0170(9) 0.0161(10) 0.0275(13) 0.0019(9) 0.0071(9) 0.0014(9)
C(8) 0.0200(10) 0.0220(10) 0.0230(10) 0.0030(10) 0.0080(10) 0.0060(10)
C(9) 0.0270(10) 0.0400(10) 0.0260(10) 0.0050(10) 0.0050(10) 0.0050(10)
C(11) 0.0196(9) 0.0167(10) 0.0267(12) -0.0038(8) 0.0067(8) -0.0001(7)
C(12) 0.0200(10) 0.0240(10) 0.049(2) -0.0090(10) 0.0010(10) 0.0030(10)
C(13) 0.0210(10) 0.0290(10) 0.066(2) -0.0150(10) 0.0020(10) -0.0010(10)
C(14) 0.0310(10) 0.0200(10) 0.047(2) -0.0050(10) 0.0150(10) -0.0040(10)
C(15) 0.0380(10) 0.0200(10) 0.032(2) 0.0000(10) 0.0040(10) 0.0040(10)
C(16) 0.0270(10) 0.0210(10) 0.0290(10) -0.0010(10) 0.0010(10) 0.0050(10)
C(17) 0.0220(10) 0.0180(10) 0.026(2) -0.0030(10) 0.0070(10) 0.0000(10)
C(18) 0.0300(10) 0.0180(10) 0.0280(10) -0.0030(10) 0.0090(10) 0.0010(10)
C(19) 0.096(2) 0.0380(10) 0.031(2) -0.0020(10) 0.0180(10) -0.0220(10)
C(21) 0.0224(9) 0.0153(10) 0.0309(12) -0.0003(7) 0.0101(9) -0.0010(7)
C(22) 0.0210(10) 0.0210(10) 0.064(2) -0.0090(10) 0.0090(10) 0.0010(10)
C(23) 0.0260(10) 0.0230(10) 0.086(2) -0.0160(10) 0.0180(10) -0.0060(10)
C(24) 0.045(2) 0.0160(10) 0.064(2) -0.0040(10) 0.0280(10) -0.0030(10)
C(25) 0.048(2) 0.0190(10) 0.040(2) 0.0020(10) 0.0130(10) 0.0090(10)
C(26) 0.0340(10) 0.0180(10) 0.0290(10) 0.0030(10) 0.0050(10) 0.0070(10)
C(27) 0.0220(10) 0.0170(10) 0.028(2) -0.0010(10) 0.0100(10) 0.0000(10)
C(28) 0.0220(10) 0.0190(10) 0.0240(10) -0.0010(10) 0.0060(10) -0.0010(10)
C(29) 0.058(2) 0.0420(10) 0.0270(10) 0.0050(10) 0.0050(10) -0.0190(10)
C(31) 0.0190(10) 0.0130(10) 0.0250(10) -0.0020(10) 0.0070(10) -0.0010(10)
C(32) 0.0210(10) 0.0170(10) 0.0340(10) -0.0020(10) 0.0100(10) 0.0000(10)
C(33) 0.0210(10) 0.0200(10) 0.039(2) 0.0030(10) 0.0100(10) -0.0030(10)
C(34) 0.0270(10) 0.0160(10) 0.036(2) 0.0000(10) 0.0060(10) -0.0020(10)
C(35) 0.0320(10) 0.0160(10) 0.0320(10) -0.0030(10) 0.0080(10) -0.0010(10)
C(36) 0.0250(10) 0.0180(10) 0.0240(10) -0.0030(10) 0.0080(10) 0.0010(10)
C(37) 0.0190(10) 0.0170(10) 0.0270(10) -0.0020(10) 0.0070(10) -0.0010(10)
C(38) 0.0200(10) 0.0180(10) 0.0280(10) -0.0030(10) 0.0100(10) -0.0020(10)
C(39) 0.0250(10) 0.0400(10) 0.027(2) -0.0060(10) 0.0000(10) -0.0030(10)

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(7) X O(1) H(1) Y
O(2) DUM1 Z O(2) C(8) Y
O(3) DUM2 Z O(3) C(8) Y
O(11) C(17) X O(11) H(11) Y
O(12) DUM3 Z O(12) C(18) Y
O(13) DUM4 Z O(13) C(18) Y
O(21) C(27) X O(21) H(21) Y
O(22) DUM5 Z O(22) C(28) Y
O(23) DUM6 Z O(23) C(28) Y
O(31) C(37) X O(31) H(31) Y
O(32) DUM7 Z O(32) C(38) Y
O(33) DUM8 Z O(33) C(38) Y
C(1) C(2) Z C(1) C(6) Y
C(2) DUM9 Z C(2) C(1) Y
C(3) DUM10 Z C(3) C(2) Y
C(4) DUM11 Z C(4) C(3) Y
C(5) DUM12 Z C(5) C(4) Y
C(6) DUM13 Z C(6) C(1) Y
C(7) O(1) X C(7) C(1) Y
C(8) O(2) X C(8) O(3) Y
C(9) O(3) Z C(9) H(9A) Y
C(11) C(12) Z C(11) C(16) Y
C(12) DUM14 Z C(12) C(11) Y
C(13) DUM15 Z C(13) C(12) Y
C(14) DUM16 Z C(14) C(13) Y
C(15) DUM17 Z C(15) C(14) Y
C(16) DUM18 Z C(16) C(11) Y
C(17) O(11) X C(17) C(11) Y
C(18) O(12) X C(18) O(13) Y
C(19) O(13) Z C(19) H(19A) Y
C(21) C(22) Z C(21) C(26) Y
C(22) DUM19 Z C(22) C(21) Y
C(23) DUM20 Z C(23) C(22) Y
C(24) DUM21 Z C(24) C(23) Y
C(25) DUM22 Z C(25) C(24) Y
C(26) DUM23 Z C(26) C(21) Y
C(27) O(21) X C(27) C(21) Y
C(28) O(22) X C(28) O(23) Y
C(29) O(23) Z C(29) H(29A) Y
C(31) C(32) Z C(31) C(36) Y
C(32) DUM24 Z C(32) C(31) Y
C(33) DUM25 Z C(33) C(32) Y
C(34) DUM26 Z C(34) C(33) Y
C(35) DUM27 Z C(35) C(34) Y
C(36) DUM28 Z C(36) C(31) Y
C(37) O(31) X C(37) C(31) Y
C(38) O(32) X C(38) O(33) Y
C(39) O(33) Z C(39) H(39A) Y
H(1) O(1) Z H(1) C(7) Y
H(2) C(2) Z H(2) C(1) Y
H(3) C(3) Z H(3) C(2) Y
H(4) C(4) Z H(4) C(3) Y
H(5) C(5) Z H(5) C(4) Y
H(6) C(6) Z H(6) C(1) Y
H(7) C(7) Z H(7) O(1) Y
H(9A) C(9) Z H(9A) O(3) Y
H(9B) C(9) Z H(9B) O(3) Y
H(9C) C(9) Z H(9C) O(3) Y
H(11) O(11) Z H(11) C(17) Y
H(12) C(12) Z H(12) C(11) Y
H(13) C(13) Z H(13) C(12) Y
H(14) C(14) Z H(14) C(13) Y
H(15) C(15) Z H(15) C(14) Y
H(16) C(16) Z H(16) C(11) Y
H(17) C(17) Z H(17) O(11) Y
H(19A) C(19) Z H(19A) O(13) Y
H(19B) C(19) Z H(19B) O(13) Y
H(19C) C(19) Z H(19C) O(13) Y
H(21) O(21) Z H(21) C(27) Y
H(22) C(22) Z H(22) C(21) Y
H(23) C(23) Z H(23) C(22) Y
H(24) C(24) Z H(24) C(23) Y
H(25) C(25) Z H(25) C(24) Y
H(26) C(26) Z H(26) C(21) Y
H(27) C(27) Z H(27) O(21) Y
H(29A) C(29) Z H(29A) O(23) Y
H(29B) C(29) Z H(29B) O(23) Y
H(29C) C(29) Z H(29C) O(23) Y
H(32) C(32) Z H(32) C(31) Y
H(33) C(33) Z H(33) C(32) Y
H(34) C(34) Z H(34) C(33) Y
H(35) C(35) Z H(35) C(34) Y
H(36) C(36) Z H(36) C(31) Y
H(37) C(37) Z H(37) O(31) Y
H(39A) C(39) Z H(39A) O(33) Y
H(39B) C(39) Z H(39B) O(33) Y
H(39C) C(39) Z H(39C) O(33) Y
H(31) O(31) Z H(31) C(37) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(7) 1.404(3) 1_555 1_555 yes
O(1) H(1) 0.9607 1_555 1_555 yes
O(2) C(8) 1.206(2) 1_555 1_555 yes
O(3) C(8) 1.332(2) 1_555 1_555 yes
O(11) C(17) 1.399(3) 1_555 1_555 yes
O(11) H(11) 0.9607 1_555 1_555 yes
O(12) C(18) 1.198(2) 1_555 1_555 yes
O(13) C(18) 1.330(2) 1_555 1_555 yes
O(13) C(19) 1.429(3) 1_555 1_555 yes
O(21) C(27) 1.409(3) 1_555 1_555 yes
O(21) H(21) 0.9607 1_555 1_555 yes
O(22) C(28) 1.201(2) 1_555 1_555 yes
O(23) C(28) 1.330(2) 1_555 1_555 yes
O(31) C(37) 1.403(3) 1_555 1_555 yes
O(31) H(31) 0.9607 1_555 1_555 yes
O(32) C(38) 1.204(2) 1_555 1_555 yes
O(33) C(38) 1.327(3) 1_555 1_555 yes
C(1) C(2) 1.390(3) 1_555 1_555 yes
C(1) C(6) 1.391(3) 1_555 1_555 yes
C(1) C(7) 1.523(3) 1_555 1_555 yes
C(2) C(3) 1.389(4) 1_555 1_555 yes
C(2) H(2) 1.082 1_555 1_555 yes
C(3) C(4) 1.394(3) 1_555 1_555 yes
C(3) H(3) 1.082 1_555 1_555 yes
C(4) C(5) 1.387(3) 1_555 1_555 yes
C(4) H(4) 1.082 1_555 1_555 yes
C(5) C(6) 1.395(3) 1_555 1_555 yes
C(5) H(5) 1.082 1_555 1_555 yes
C(6) H(6) 1.082 1_555 1_555 yes
C(7) C(8) 1.517(3) 1_555 1_555 yes
C(7) H(7) 1.098 1_555 1_555 yes
C(9) H(9A) 1.095 1_555 1_555 yes
C(9) H(9B) 1.095 1_555 1_555 yes
C(9) H(9C) 1.095 1_555 1_555 yes
C(11) C(12) 1.379(3) 1_555 1_555 yes
C(11) C(16) 1.384(2) 1_555 1_555 yes
C(11) C(17) 1.528(2) 1_555 1_555 yes
C(12) C(13) 1.392(3) 1_555 1_555 yes
C(12) H(12) 1.082 1_555 1_555 yes
C(13) C(14) 1.390(3) 1_555 1_555 yes
C(13) H(13) 1.082 1_555 1_555 yes
C(14) C(15) 1.375(4) 1_555 1_555 yes
C(14) H(14) 1.082 1_555 1_555 yes
C(15) C(16) 1.395(3) 1_555 1_555 yes
C(15) H(15) 1.082 1_555 1_555 yes
C(16) H(16) 1.082 1_555 1_555 yes
C(17) C(18) 1.524(3) 1_555 1_555 yes
C(17) H(17) 1.098 1_555 1_555 yes
C(19) H(19A) 1.095 1_555 1_555 yes
C(19) H(19B) 1.095 1_555 1_555 yes
C(19) H(19C) 1.095 1_555 1_555 yes
C(21) C(22) 1.379(3) 1_555 1_555 yes
C(21) C(26) 1.382(2) 1_555 1_555 yes
C(21) C(27) 1.524(2) 1_555 1_555 yes
C(22) C(23) 1.387(3) 1_555 1_555 yes
C(22) H(22) 1.082 1_555 1_555 yes
C(23) C(24) 1.388(3) 1_555 1_555 yes
C(23) H(23) 1.082 1_555 1_555 yes
C(24) C(25) 1.389(4) 1_555 1_555 yes
C(24) H(24) 1.082 1_555 1_555 yes
C(25) C(26) 1.392(3) 1_555 1_555 yes
C(25) H(25) 1.082 1_555 1_555 yes
C(26) H(26) 1.082 1_555 1_555 yes
C(27) C(28) 1.522(3) 1_555 1_555 yes
C(27) H(27) 1.098 1_555 1_555 yes
C(29) H(29A) 1.095 1_555 1_555 yes
C(29) H(29B) 1.095 1_555 1_555 yes
C(29) H(29C) 1.095 1_555 1_555 yes
C(31) C(32) 1.385(3) 1_555 1_555 yes
C(31) C(36) 1.392(3) 1_555 1_555 yes
C(31) C(37) 1.521(3) 1_555 1_555 yes
C(32) C(33) 1.392(3) 1_555 1_555 yes
C(32) H(32) 1.082 1_555 1_555 yes
C(33) C(34) 1.387(3) 1_555 1_555 yes
C(33) H(33) 1.082 1_555 1_555 yes
C(34) C(35) 1.393(3) 1_555 1_555 yes
C(34) H(34) 1.082 1_555 1_555 yes
C(35) C(36) 1.391(3) 1_555 1_555 yes
C(35) H(35) 1.082 1_555 1_555 yes
C(36) H(36) 1.082 1_555 1_555 yes
C(37) C(38) 1.522(3) 1_555 1_555 yes
C(37) H(37) 1.098 1_555 1_555 yes
C(39) H(39A) 1.095 1_555 1_555 yes
C(39) H(39B) 1.095 1_555 1_555 yes
C(39) H(39C) 1.095 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(18) O(13) C(19) 115.26(17) 1_555 1_555 1_555 yes
C(2) C(1) C(6) 120.21(19) 1_555 1_555 1_555 yes
C(2) C(1) C(7) 120.01(18) 1_555 1_555 1_555 yes
C(6) C(1) C(7) 119.77(19) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 120.18(19) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 120.0(2) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.6(2) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 120.8(2) 1_555 1_555 1_555 yes
C(1) C(6) C(5) 119.3(2) 1_555 1_555 1_555 yes
O(1) C(7) C(1) 113.20(17) 1_555 1_555 1_555 yes
O(1) C(7) C(8) 106.43(16) 1_555 1_555 1_555 yes
C(1) C(7) C(8) 109.14(16) 1_555 1_555 1_555 yes
O(2) C(8) O(3) 123.16(19) 1_555 1_555 1_555 yes
O(2) C(8) C(7) 124.90(19) 1_555 1_555 1_555 yes
O(3) C(8) C(7) 111.94(17) 1_555 1_555 1_555 yes
C(12) C(11) C(16) 119.45(17) 1_555 1_555 1_555 yes
C(12) C(11) C(17) 120.64(17) 1_555 1_555 1_555 yes
C(16) C(11) C(17) 119.88(17) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 120.34(18) 1_555 1_555 1_555 yes
C(12) C(13) C(14) 120.23(19) 1_555 1_555 1_555 yes
C(13) C(14) C(15) 119.29(19) 1_555 1_555 1_555 yes
C(14) C(15) C(16) 120.5(2) 1_555 1_555 1_555 yes
C(11) C(16) C(15) 120.15(19) 1_555 1_555 1_555 yes
O(11) C(17) C(11) 112.67(16) 1_555 1_555 1_555 yes
O(11) C(17) C(18) 106.24(19) 1_555 1_555 1_555 yes
C(11) C(17) C(18) 111.17(19) 1_555 1_555 1_555 yes
O(12) C(18) O(13) 124.01(19) 1_555 1_555 1_555 yes
O(12) C(18) C(17) 124.4(2) 1_555 1_555 1_555 yes
O(13) C(18) C(17) 111.61(18) 1_555 1_555 1_555 yes
C(22) C(21) C(26) 119.59(17) 1_555 1_555 1_555 yes
C(22) C(21) C(27) 121.02(18) 1_555 1_555 1_555 yes
C(26) C(21) C(27) 119.32(18) 1_555 1_555 1_555 yes
C(21) C(22) C(23) 120.22(18) 1_555 1_555 1_555 yes
C(22) C(23) C(24) 120.4(2) 1_555 1_555 1_555 yes
C(23) C(24) C(25) 119.5(2) 1_555 1_555 1_555 yes
C(24) C(25) C(26) 119.6(2) 1_555 1_555 1_555 yes
C(21) C(26) C(25) 120.7(2) 1_555 1_555 1_555 yes
O(21) C(27) C(21) 112.62(17) 1_555 1_555 1_555 yes
O(21) C(27) C(28) 105.49(19) 1_555 1_555 1_555 yes
C(21) C(27) C(28) 110.56(19) 1_555 1_555 1_555 yes
O(22) C(28) O(23) 123.86(18) 1_555 1_555 1_555 yes
O(22) C(28) C(27) 124.16(19) 1_555 1_555 1_555 yes
O(23) C(28) C(27) 111.98(17) 1_555 1_555 1_555 yes
C(32) C(31) C(36) 120.04(19) 1_555 1_555 1_555 yes
C(32) C(31) C(37) 120.15(19) 1_555 1_555 1_555 yes
C(36) C(31) C(37) 119.81(18) 1_555 1_555 1_555 yes
C(31) C(32) C(33) 119.9(2) 1_555 1_555 1_555 yes
C(32) C(33) C(34) 120.4(2) 1_555 1_555 1_555 yes
C(33) C(34) C(35) 119.6(2) 1_555 1_555 1_555 yes
C(34) C(35) C(36) 120.1(2) 1_555 1_555 1_555 yes
C(31) C(36) C(35) 119.9(2) 1_555 1_555 1_555 yes
O(31) C(37) C(31) 113.52(17) 1_555 1_555 1_555 yes
O(31) C(37) C(38) 106.94(16) 1_555 1_555 1_555 yes
C(31) C(37) C(38) 109.52(16) 1_555 1_555 1_555 yes
O(32) C(38) O(33) 124.23(19) 1_555 1_555 1_555 yes
O(32) C(38) C(37) 124.14(19) 1_555 1_555 1_555 yes
O(33) C(38) C(37) 111.62(17) 1_555 1_555 1_555 yes