# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# 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_cm001-p21-n
#TrackingRef '19304_web_deposit_cif_file_0_Prof.ManatPohmakotr_1365515774.cm001.CIF'
_audit_update_record
;
2013-04-09 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H15 F3 O3'
_chemical_formula_sum 'C17 H15 F3 O3'
_chemical_formula_weight 324.29
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n '
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 5.8968(7)
_cell_length_b 21.674(2)
_cell_length_c 12.1696(13)
_cell_angle_alpha 90.00
_cell_angle_beta 103.342(2)
_cell_angle_gamma 90.00
_cell_volume 1513.4(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 740
_cell_measurement_theta_min 2.55
_cell_measurement_theta_max 25.57
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.302
_exptl_crystal_size_mid 0.089
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.423
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 672
_exptl_absorpt_coefficient_mu 0.121
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.087
_exptl_absorpt_correction_T_max 0.998
_exptl_absorpt_process_details 'SADABS (Bruker, 2003)'
_exptl_special_details ?
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX CCD area-detector'
_diffrn_measurement_method 'Frames, each covering 0.3 \% in \w'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_diffrn_reflns_number 14149
_diffrn_reflns_av_R_equivalents 0.0950
_diffrn_reflns_av_sigmaI/netI 0.0699
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -25
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 1.88
_diffrn_reflns_theta_max 25.00
_reflns_number_total 2662
_reflns_number_gt 1565
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART (Bruker, 1998)'
_computing_cell_refinement 'SAINT (Bruker, 2003)'
_computing_data_reduction 'SAINT (Bruker, 2003)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Mercury 3.0 (Macrae et al., 2008)'
_computing_publication_material
'SHEXTL(Sheldrick, 2008), Platon (Spek, 2009) and publCIF (Westrip, 2010)'
_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^)+(0.0618P)^2^+2.7805P] 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 constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2662
_refine_ls_number_parameters 209
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1709
_refine_ls_R_factor_gt 0.1027
_refine_ls_wR_factor_ref 0.2251
_refine_ls_wR_factor_gt 0.1932
_refine_ls_goodness_of_fit_ref 1.091
_refine_ls_restrained_S_all 1.090
_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
C1 C -0.2443(12) 0.2270(3) 0.6274(4) 0.0599(16) Uani 1 1 d . . .
O1 O -0.3541(12) 0.2708(2) 0.6424(4) 0.109(2) Uani 1 1 d . . .
C3 C -0.1553(8) 0.1235(2) 0.6334(4) 0.0442(13) Uani 1 1 d . . .
C3A C 0.0109(9) 0.1551(3) 0.5700(5) 0.071(2) Uani 1 1 d . . .
H3A H 0.1709 0.1425 0.6050 0.085 Uiso 1 1 calc R . .
C7A C -0.0164(11) 0.2227(3) 0.5944(5) 0.073(2) Uani 1 1 d . . .
H7A H 0.1119 0.2374 0.6550 0.088 Uiso 1 1 calc R . .
C4 C -0.0204(11) 0.1552(3) 0.4387(5) 0.077(2) Uani 1 1 d . . .
H4 H 0.0217 0.1168 0.4058 0.093 Uiso 1 1 calc R . .
C5 C -0.2512(10) 0.1829(3) 0.3807(4) 0.0609(15) Uani 1 1 d U . .
H5 H -0.3758 0.1617 0.3357 0.073 Uiso 1 1 calc R . .
C6 C -0.2467(10) 0.2415(3) 0.4044(4) 0.0566(15) Uani 1 1 d U . .
H6 H -0.3662 0.2697 0.3788 0.068 Uiso 1 1 calc R . .
C7 C -0.0155(12) 0.2551(3) 0.4797(5) 0.081(2) Uani 1 1 d . . .
H7 H 0.0336 0.2984 0.4842 0.097 Uiso 1 1 calc R . .
C8 C 0.1349(11) 0.2104(4) 0.4319(6) 0.116(3) Uani 1 1 d . . .
H8A H 0.2905 0.2060 0.4795 0.139 Uiso 1 1 calc R . .
H8B H 0.1427 0.2203 0.3552 0.139 Uiso 1 1 calc R . .
O2 O -0.3323(5) 0.16916(14) 0.6338(2) 0.0411(8) Uani 1 1 d . . .
O3 O 0.2929(11) 0.0595(3) 1.0837(5) 0.144(3) Uani 1 1 d . . .
C9 C -0.2865(12) 0.0678(3) 0.5754(5) 0.0634(17) Uani 1 1 d . . .
F1 F -0.4274(7) 0.04338(14) 0.6344(3) 0.0800(11) Uani 1 1 d . . .
F2 F -0.1442(9) 0.02422(19) 0.5608(4) 0.1306(19) Uani 1 1 d . . .
F3 F -0.4234(8) 0.08011(16) 0.4737(3) 0.1013(14) Uani 1 1 d . . .
C1' C -0.0388(9) 0.1065(3) 0.7540(5) 0.0545(15) Uani 1 1 d . . .
C2' C -0.1427(11) 0.1183(2) 0.8406(4) 0.0569(15) Uani 1 1 d . . .
H2' H -0.2883 0.1372 0.8254 0.068 Uiso 1 1 calc R . .
C3' C -0.0366(15) 0.1029(3) 0.9512(5) 0.081(2) Uani 1 1 d . . .
H3' H -0.1098 0.1121 1.0093 0.097 Uiso 1 1 calc R . .
C4' C 0.1763(16) 0.0743(4) 0.9748(7) 0.102(3) Uani 1 1 d . . .
C5' C 0.2781(13) 0.0612(5) 0.8900(8) 0.140(4) Uani 1 1 d . . .
H5' H 0.4223 0.0417 0.9053 0.168 Uiso 1 1 calc R . .
C6' C 0.1722(11) 0.0765(4) 0.7806(6) 0.121(4) Uani 1 1 d . . .
H6' H 0.2452 0.0662 0.7230 0.146 Uiso 1 1 calc R . .
C10 C 0.191(3) 0.0703(4) 1.1750(7) 0.203(7) Uani 1 1 d . . .
H10A H 0.1637 0.1137 1.1808 0.305 Uiso 1 1 calc R . .
H10C H 0.2938 0.0561 1.2433 0.305 Uiso 1 1 calc R . .
H10B H 0.0457 0.0485 1.1634 0.305 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
C1 0.097(5) 0.052(4) 0.028(3) 0.001(3) 0.009(3) -0.020(4)
O1 0.219(6) 0.045(2) 0.080(3) 0.000(2) 0.071(4) 0.010(3)
C3 0.026(3) 0.064(3) 0.045(3) 0.014(3) 0.014(2) 0.013(3)
C3A 0.029(3) 0.128(6) 0.058(4) 0.047(4) 0.016(3) 0.014(3)
C7A 0.062(4) 0.107(5) 0.039(3) 0.024(3) -0.012(3) -0.045(4)
C4 0.072(4) 0.114(5) 0.060(4) 0.030(4) 0.042(3) 0.038(4)
C5 0.064(4) 0.088(4) 0.029(3) 0.006(3) 0.007(3) 0.007(4)
C6 0.054(4) 0.072(4) 0.042(3) 0.022(3) 0.009(3) 0.010(3)
C7 0.076(5) 0.108(5) 0.052(4) 0.032(4) 0.001(4) -0.039(4)
C8 0.044(4) 0.215(10) 0.095(5) 0.088(6) 0.031(4) 0.017(5)
O2 0.0343(18) 0.044(2) 0.0460(19) 0.0059(16) 0.0112(15) 0.0033(16)
O3 0.163(6) 0.130(5) 0.099(4) 0.078(4) -0.055(4) -0.042(4)
C9 0.087(5) 0.057(4) 0.055(4) 0.004(3) 0.033(4) 0.017(3)
F1 0.102(3) 0.060(2) 0.086(2) -0.0060(18) 0.037(2) -0.021(2)
F2 0.193(5) 0.088(3) 0.139(4) 0.000(3) 0.096(4) 0.065(3)
F3 0.157(4) 0.072(2) 0.062(2) -0.0053(19) -0.001(2) -0.027(3)
C1' 0.033(3) 0.076(4) 0.056(3) 0.030(3) 0.014(3) -0.001(3)
C2' 0.074(4) 0.049(3) 0.045(3) 0.007(3) 0.009(3) -0.008(3)
C3' 0.141(7) 0.056(4) 0.042(4) 0.007(3) 0.010(4) -0.015(4)
C4' 0.100(6) 0.091(5) 0.086(6) 0.057(5) -0.036(5) -0.042(5)
C5' 0.049(4) 0.230(11) 0.135(8) 0.130(8) 0.008(5) 0.014(5)
C6' 0.045(4) 0.219(9) 0.108(6) 0.111(6) 0.033(4) 0.051(5)
C10 0.42(2) 0.087(6) 0.052(5) 0.033(5) -0.045(8) -0.029(9)
_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
C1 O1 1.187(7) . ?
C1 O2 1.366(6) . ?
C1 C7A 1.491(9) . ?
C3 O2 1.438(5) . ?
C3 C1' 1.516(7) . ?
C3 C9 1.517(8) . ?
C3 C3A 1.541(7) . ?
C3A C7A 1.512(9) . ?
C3A C4 1.566(8) . ?
C3A H3A 0.9800 . ?
C7A C7 1.565(7) . ?
C7A H7A 0.9800 . ?
C4 C5 1.506(8) . ?
C4 C8 1.521(10) . ?
C4 H4 0.9800 . ?
C5 C6 1.302(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.517(10) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O3 C4' 1.383(8) . ?
O3 C10 1.399(13) . ?
C9 F2 1.303(6) . ?
C9 F1 1.328(6) . ?
C9 F3 1.339(7) . ?
C1' C2' 1.360(7) . ?
C1' C6' 1.375(8) . ?
C2' C3' 1.388(8) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.371(11) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.338(12) . ?
C5' C6' 1.374(10) . ?
C5' H5' 0.9300 . ?
C6' H6' 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10C 0.9600 . ?
C10 H10B 0.9600 . ?
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
O1 C1 O2 119.8(6) . . ?
O1 C1 C7A 130.4(6) . . ?
O2 C1 C7A 109.6(5) . . ?
O2 C3 C1' 109.4(4) . . ?
O2 C3 C9 104.9(4) . . ?
C1' C3 C9 109.0(4) . . ?
O2 C3 C3A 104.0(4) . . ?
C1' C3 C3A 113.2(4) . . ?
C9 C3 C3A 115.8(5) . . ?
C7A C3A C3 102.9(5) . . ?
C7A C3A C4 101.9(5) . . ?
C3 C3A C4 125.0(5) . . ?
C7A C3A H3A 108.6 . . ?
C3 C3A H3A 108.6 . . ?
C4 C3A H3A 108.6 . . ?
C1 C7A C3A 104.9(5) . . ?
C1 C7A C7 113.7(5) . . ?
C3A C7A C7 103.7(5) . . ?
C1 C7A H7A 111.4 . . ?
C3A C7A H7A 111.4 . . ?
C7 C7A H7A 111.4 . . ?
C5 C4 C8 98.7(5) . . ?
C5 C4 C3A 111.0(4) . . ?
C8 C4 C3A 97.2(6) . . ?
C5 C4 H4 115.7 . . ?
C8 C4 H4 115.7 . . ?
C3A C4 H4 115.7 . . ?
C6 C5 C4 108.4(6) . . ?
C6 C5 H5 125.8 . . ?
C4 C5 H5 125.8 . . ?
C5 C6 C7 107.4(6) . . ?
C5 C6 H6 126.3 . . ?
C7 C6 H6 126.3 . . ?
C6 C7 C8 99.9(6) . . ?
C6 C7 C7A 105.7(5) . . ?
C8 C7 C7A 100.2(6) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 H7 116.2 . . ?
C7A C7 H7 116.2 . . ?
C7 C8 C4 94.0(5) . . ?
C7 C8 H8A 112.9 . . ?
C4 C8 H8A 112.9 . . ?
C7 C8 H8B 112.9 . . ?
C4 C8 H8B 112.9 . . ?
H8A C8 H8B 110.3 . . ?
C1 O2 C3 110.2(4) . . ?
C4' O3 C10 120.8(9) . . ?
F2 C9 F1 106.7(5) . . ?
F2 C9 F3 106.8(5) . . ?
F1 C9 F3 105.1(5) . . ?
F2 C9 C3 111.4(6) . . ?
F1 C9 C3 112.4(4) . . ?
F3 C9 C3 113.9(5) . . ?
C2' C1' C6' 116.9(5) . . ?
C2' C1' C3 121.3(5) . . ?
C6' C1' C3 121.8(5) . . ?
C1' C2' C3' 121.6(6) . . ?
C1' C2' H2' 119.2 . . ?
C3' C2' H2' 119.2 . . ?
C4' C3' C2' 119.8(7) . . ?
C4' C3' H3' 120.1 . . ?
C2' C3' H3' 120.1 . . ?
C5' C4' C3' 119.1(6) . . ?
C5' C4' O3 118.5(9) . . ?
C3' C4' O3 122.3(9) . . ?
C4' C5' C6' 120.8(8) . . ?
C4' C5' H5' 119.6 . . ?
C6' C5' H5' 119.6 . . ?
C5' C6' C1' 121.7(7) . . ?
C5' C6' H6' 119.2 . . ?
C1' C6' H6' 119.2 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10C C10 H10B 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
O2 C3 C3A C7A 28.4(5) . . . . ?
C1' C3 C3A C7A -90.2(5) . . . . ?
C9 C3 C3A C7A 142.9(5) . . . . ?
O2 C3 C3A C4 -86.3(7) . . . . ?
C1' C3 C3A C4 155.1(5) . . . . ?
C9 C3 C3A C4 28.2(8) . . . . ?
O1 C1 C7A C3A -170.8(6) . . . . ?
O2 C1 C7A C3A 5.6(5) . . . . ?
O1 C1 C7A C7 -58.2(9) . . . . ?
O2 C1 C7A C7 118.2(6) . . . . ?
C3 C3A C7A C1 -20.7(5) . . . . ?
C4 C3A C7A C1 109.8(5) . . . . ?
C3 C3A C7A C7 -140.2(4) . . . . ?
C4 C3A C7A C7 -9.7(6) . . . . ?
C7A C3A C4 C5 -57.2(7) . . . . ?
C3 C3A C4 C5 58.0(8) . . . . ?
C7A C3A C4 C8 45.0(6) . . . . ?
C3 C3A C4 C8 160.2(6) . . . . ?
C8 C4 C5 C6 -33.1(6) . . . . ?
C3A C4 C5 C6 68.2(7) . . . . ?
C4 C5 C6 C7 -0.7(6) . . . . ?
C5 C6 C7 C8 34.4(6) . . . . ?
C5 C6 C7 C7A -69.2(7) . . . . ?
C1 C7A C7 C6 -39.0(8) . . . . ?
C3A C7A C7 C6 74.3(7) . . . . ?
C1 C7A C7 C8 -142.4(6) . . . . ?
C3A C7A C7 C8 -29.1(6) . . . . ?
C6 C7 C8 C4 -51.4(5) . . . . ?
C7A C7 C8 C4 56.6(5) . . . . ?
C5 C4 C8 C7 50.2(5) . . . . ?
C3A C4 C8 C7 -62.5(5) . . . . ?
O1 C1 O2 C3 -169.6(5) . . . . ?
C7A C1 O2 C3 13.6(5) . . . . ?
C1' C3 O2 C1 94.6(4) . . . . ?
C9 C3 O2 C1 -148.7(4) . . . . ?
C3A C3 O2 C1 -26.7(5) . . . . ?
O2 C3 C9 F2 174.7(4) . . . . ?
C1' C3 C9 F2 -68.2(6) . . . . ?
C3A C3 C9 F2 60.8(6) . . . . ?
O2 C3 C9 F1 -65.5(5) . . . . ?
C1' C3 C9 F1 51.5(6) . . . . ?
C3A C3 C9 F1 -179.5(4) . . . . ?
O2 C3 C9 F3 53.9(6) . . . . ?
C1' C3 C9 F3 170.9(5) . . . . ?
C3A C3 C9 F3 -60.1(6) . . . . ?
O2 C3 C1' C2' 19.2(7) . . . . ?
C9 C3 C1' C2' -94.9(6) . . . . ?
C3A C3 C1' C2' 134.7(5) . . . . ?
O2 C3 C1' C6' -163.1(6) . . . . ?
C9 C3 C1' C6' 82.7(7) . . . . ?
C3A C3 C1' C6' -47.6(8) . . . . ?
C6' C1' C2' C3' 2.4(9) . . . . ?
C3 C1' C2' C3' -179.8(5) . . . . ?
C1' C2' C3' C4' -1.0(9) . . . . ?
C2' C3' C4' C5' -0.3(11) . . . . ?
C2' C3' C4' O3 178.2(6) . . . . ?
C10 O3 C4' C5' -178.0(8) . . . . ?
C10 O3 C4' C3' 3.5(11) . . . . ?
C3' C4' C5' C6' 0.2(14) . . . . ?
O3 C4' C5' C6' -178.3(8) . . . . ?
C4' C5' C6' C1' 1.2(15) . . . . ?
C2' C1' C6' C5' -2.5(12) . . . . ?
C3 C1' C6' C5' 179.7(7) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.234
_refine_diff_density_min -0.306
_refine_diff_density_rms 0.050
_database_code_depnum_ccdc_archive 'CCDC 933154'
#######################################################################
#
# 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_cm002-rt-c2-c
#TrackingRef 'web_deposit_cif_file_2_Prof.ManatPohmakotr_1365515774.cm002.cif'
_audit_update_record
;
2013-04-09 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C10 H8 F3 O3, H'
_chemical_formula_sum 'C10 H9 F3 O3'
_chemical_formula_weight 234.17
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 17.239(11)
_cell_length_b 12.975(8)
_cell_length_c 12.221(7)
_cell_angle_alpha 90.00
_cell_angle_beta 134.379(10)
_cell_angle_gamma 90.00
_cell_volume 1954(2)
_cell_formula_units_Z 8
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 998
_cell_measurement_theta_min 2.28
_cell_measurement_theta_max 21.56
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.163
_exptl_crystal_size_mid 0.136
_exptl_crystal_size_min 0.072
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.592
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 960
_exptl_absorpt_coefficient_mu 0.153
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.975
_exptl_absorpt_correction_T_max 0.985
_exptl_absorpt_process_details 'SADABS (Bruker, 2003)'
_exptl_special_details ?
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX CCD area-detector'
_diffrn_measurement_method 'Frames, each covering 0.3 \% in \w'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_diffrn_reflns_number 7440
_diffrn_reflns_av_R_equivalents 0.7145
_diffrn_reflns_av_sigmaI/netI 0.6044
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.29
_diffrn_reflns_theta_max 27.88
_reflns_number_total 2304
_reflns_number_gt 833
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART (Bruker, 1998)'
_computing_cell_refinement 'SAINT (Bruker, 2003)'
_computing_data_reduction 'SAINT (Bruker, 2003)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Mercury 3.0 (Macrae et al., 2008)'
_computing_publication_material
'SHEXTL(Sheldrick, 2008), Platon (Spek, 2009) and publCIF (Westrip, 2010)'
_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^)+(0.1103P)^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_number_reflns 2304
_refine_ls_number_parameters 148
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1909
_refine_ls_R_factor_gt 0.1265
_refine_ls_wR_factor_ref 0.2964
_refine_ls_wR_factor_gt 0.2795
_refine_ls_goodness_of_fit_ref 0.960
_refine_ls_restrained_S_all 0.960
_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
C1 C 0.6938(3) 0.7398(5) 0.7204(5) 0.0237(12) Uani 1 1 d . . .
O2 O 0.8044(2) 0.7471(3) 0.8278(3) 0.0242(9) Uani 1 1 d . . .
C3 C 0.8522(3) 0.6453(4) 0.8552(4) 0.0202(11) Uani 1 1 d . . .
C3A C 0.7589(4) 0.5683(5) 0.7726(5) 0.0259(11) Uani 1 1 d . . .
H4A H 0.7588 0.5208 0.7102 0.031 Uiso 1 1 calc R . .
C4 C 0.7492(5) 0.5078(5) 0.8733(6) 0.0328(12) Uani 1 1 d . . .
H5 H 0.7977 0.4484 0.9293 0.039 Uiso 1 1 calc R . .
C5 C 0.7479(5) 0.5812(5) 0.9642(6) 0.0377(15) Uani 1 1 d . . .
H6 H 0.8029 0.5902 1.0697 0.045 Uiso 1 1 calc R . .
C6 C 0.6547(5) 0.6323(6) 0.8693(7) 0.0416(16) Uani 1 1 d . . .
H7 H 0.6326 0.6824 0.8971 0.050 Uiso 1 1 calc R . .
C7 C 0.5909(5) 0.5955(6) 0.7093(7) 0.0402(16) Uani 1 1 d . . .
H8 H 0.5126 0.6091 0.6326 0.048 Uiso 1 1 calc R . .
C7A C 0.6568(4) 0.6347(5) 0.6716(5) 0.0251(12) Uani 1 1 d . . .
H7A H 0.6153 0.6257 0.5630 0.030 Uiso 1 1 calc R . .
C8 C 0.6262(5) 0.4827(6) 0.7448(8) 0.0467(17) Uani 1 1 d . . .
H8A H 0.6068 0.4466 0.6590 0.056 Uiso 1 1 calc R . .
H8B H 0.5997 0.4453 0.7821 0.056 Uiso 1 1 calc R . .
O1 O 0.6440(3) 0.8198(4) 0.6860(4) 0.0434(12) Uani 1 1 d . . .
O3 O 0.9324(2) 0.6283(4) 1.0084(3) 0.0359(12) Uani 1 1 d . . .
H3 H 1.009(5) 0.689(5) 1.042(7) 0.043 Uiso 1 1 d . . .
C9 C 0.8956(4) 0.6527(5) 0.7824(6) 0.0298(13) Uani 1 1 d . . .
F1 F 0.9421(4) 0.5671(3) 0.7980(5) 0.0596(13) Uani 1 1 d . . .
F2 F 0.9690(3) 0.7271(3) 0.8444(4) 0.0478(11) Uani 1 1 d . . .
F3 F 0.8159(3) 0.6724(4) 0.6321(3) 0.0546(13) Uani 1 1 d . . .
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
C1 0.009(2) 0.029(3) 0.0224(18) 0.000(2) 0.0071(17) 0.002(2)
O2 0.0129(16) 0.020(2) 0.0274(14) -0.0039(17) 0.0098(12) -0.0012(16)
C3 0.012(2) 0.029(3) 0.0162(17) 0.001(2) 0.0082(17) 0.007(2)
C3A 0.021(2) 0.030(3) 0.0285(19) -0.004(3) 0.0182(19) -0.003(3)
C4 0.038(3) 0.028(3) 0.039(2) -0.001(3) 0.029(2) -0.005(3)
C5 0.050(3) 0.039(4) 0.044(3) -0.016(3) 0.041(3) -0.024(3)
C6 0.051(4) 0.046(4) 0.061(3) -0.017(4) 0.052(3) -0.017(4)
C7 0.027(3) 0.039(4) 0.057(3) -0.024(3) 0.031(3) -0.011(3)
C7A 0.013(2) 0.026(3) 0.0260(18) -0.002(3) 0.0098(18) 0.007(2)
C8 0.047(4) 0.037(4) 0.068(4) -0.026(4) 0.044(3) -0.025(4)
O1 0.022(2) 0.040(3) 0.0446(19) 0.000(2) 0.0149(18) 0.013(2)
O3 0.0125(17) 0.063(3) 0.0221(14) 0.012(2) 0.0084(13) 0.001(2)
C9 0.029(3) 0.037(3) 0.033(2) 0.007(3) 0.025(2) 0.009(3)
F1 0.072(3) 0.051(3) 0.104(3) 0.024(3) 0.079(2) 0.033(2)
F2 0.0385(19) 0.057(3) 0.064(2) -0.004(2) 0.0412(17) -0.015(2)
F3 0.056(2) 0.088(3) 0.0297(13) 0.014(2) 0.0333(15) 0.004(2)
_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
C1 O1 1.219(7) . ?
C1 O2 1.366(5) . ?
C1 C7A 1.446(8) . ?
O2 C3 1.466(6) . ?
C3 O3 1.358(5) . ?
C3 C9 1.514(6) . ?
C3 C3A 1.527(8) . ?
C3A C7A 1.524(7) . ?
C3A C4 1.564(7) . ?
C3A H4A 0.9800 . ?
C4 C5 1.476(8) . ?
C4 C8 1.553(8) . ?
C4 H5 0.9800 . ?
C5 C6 1.326(9) . ?
C5 H6 0.9300 . ?
C6 C7 1.501(9) . ?
C6 H7 0.9300 . ?
C7 C8 1.527(10) . ?
C7 C7A 1.579(8) . ?
C7 H8 0.9800 . ?
C7A H7A 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O3 H3 1.34(7) . ?
C9 F1 1.305(8) . ?
C9 F2 1.329(7) . ?
C9 F3 1.340(6) . ?
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
O1 C1 O2 116.5(5) . . ?
O1 C1 C7A 131.2(4) . . ?
O2 C1 C7A 112.2(4) . . ?
C1 O2 C3 109.9(4) . . ?
O3 C3 O2 109.2(4) . . ?
O3 C3 C9 112.1(4) . . ?
O2 C3 C9 103.8(4) . . ?
O3 C3 C3A 113.0(4) . . ?
O2 C3 C3A 105.9(4) . . ?
C9 C3 C3A 112.2(4) . . ?
C7A C3A C3 104.6(5) . . ?
C7A C3A C4 102.9(4) . . ?
C3 C3A C4 116.8(4) . . ?
C7A C3A H4A 110.7 . . ?
C3 C3A H4A 110.7 . . ?
C4 C3A H4A 110.7 . . ?
C5 C4 C8 99.6(5) . . ?
C5 C4 C3A 109.5(5) . . ?
C8 C4 C3A 97.6(4) . . ?
C5 C4 H5 115.9 . . ?
C8 C4 H5 115.9 . . ?
C3A C4 H5 115.9 . . ?
C6 C5 C4 108.1(5) . . ?
C6 C5 H6 125.9 . . ?
C4 C5 H6 125.9 . . ?
C5 C6 C7 108.4(5) . . ?
C5 C6 H7 125.8 . . ?
C7 C6 H7 125.8 . . ?
C6 C7 C8 98.7(6) . . ?
C6 C7 C7A 104.8(4) . . ?
C8 C7 C7A 99.6(5) . . ?
C6 C7 H8 116.9 . . ?
C8 C7 H8 116.9 . . ?
C7A C7 H8 116.9 . . ?
C1 C7A C3A 105.8(4) . . ?
C1 C7A C7 112.6(5) . . ?
C3A C7A C7 103.9(5) . . ?
C1 C7A H7A 111.4 . . ?
C3A C7A H7A 111.4 . . ?
C7 C7A H7A 111.4 . . ?
C7 C8 C4 94.4(5) . . ?
C7 C8 H8A 112.8 . . ?
C4 C8 H8A 112.8 . . ?
C7 C8 H8B 112.8 . . ?
C4 C8 H8B 112.8 . . ?
H8A C8 H8B 110.3 . . ?
C3 O3 H3 99(3) . . ?
F1 C9 F2 107.0(4) . . ?
F1 C9 F3 107.4(5) . . ?
F2 C9 F3 107.3(5) . . ?
F1 C9 C3 111.5(5) . . ?
F2 C9 C3 112.1(5) . . ?
F3 C9 C3 111.3(4) . . ?
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
O1 C1 O2 C3 -179.3(4) . . . . ?
C7A C1 O2 C3 3.0(6) . . . . ?
C1 O2 C3 O3 -131.8(4) . . . . ?
C1 O2 C3 C9 108.5(4) . . . . ?
C1 O2 C3 C3A -9.8(5) . . . . ?
O3 C3 C3A C7A 131.9(4) . . . . ?
O2 C3 C3A C7A 12.4(4) . . . . ?
C9 C3 C3A C7A -100.2(5) . . . . ?
O3 C3 C3A C4 18.9(7) . . . . ?
O2 C3 C3A C4 -100.6(5) . . . . ?
C9 C3 C3A C4 146.9(5) . . . . ?
C7A C3A C4 C5 -60.9(5) . . . . ?
C3 C3A C4 C5 53.0(6) . . . . ?
C7A C3A C4 C8 42.1(5) . . . . ?
C3 C3A C4 C8 156.0(5) . . . . ?
C8 C4 C5 C6 -32.0(6) . . . . ?
C3A C4 C5 C6 69.6(6) . . . . ?
C4 C5 C6 C7 -1.2(7) . . . . ?
C5 C6 C7 C8 34.5(6) . . . . ?
C5 C6 C7 C7A -68.0(7) . . . . ?
O1 C1 C7A C3A -172.1(5) . . . . ?
O2 C1 C7A C3A 5.2(6) . . . . ?
O1 C1 C7A C7 -59.2(7) . . . . ?
O2 C1 C7A C7 118.1(5) . . . . ?
C3 C3A C7A C1 -10.7(5) . . . . ?
C4 C3A C7A C1 111.8(5) . . . . ?
C3 C3A C7A C7 -129.5(4) . . . . ?
C4 C3A C7A C7 -7.0(5) . . . . ?
C6 C7 C7A C1 -43.7(7) . . . . ?
C8 C7 C7A C1 -145.4(5) . . . . ?
C6 C7 C7A C3A 70.3(6) . . . . ?
C8 C7 C7A C3A -31.4(5) . . . . ?
C6 C7 C8 C4 -50.0(5) . . . . ?
C7A C7 C8 C4 56.8(5) . . . . ?
C5 C4 C8 C7 50.1(5) . . . . ?
C3A C4 C8 C7 -61.2(5) . . . . ?
O3 C3 C9 F1 61.9(7) . . . . ?
O2 C3 C9 F1 179.6(4) . . . . ?
C3A C3 C9 F1 -66.5(6) . . . . ?
O3 C3 C9 F2 -58.0(7) . . . . ?
O2 C3 C9 F2 59.7(5) . . . . ?
C3A C3 C9 F2 173.6(4) . . . . ?
O3 C3 C9 F3 -178.3(5) . . . . ?
O2 C3 C9 F3 -60.6(6) . . . . ?
C3A C3 C9 F3 53.3(7) . . . . ?
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
O3 H3 O1 1.34(7) 1.67(6) 2.721(5) 129(5) 8_566
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full 27.88
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max 0.638
_refine_diff_density_min -0.629
_refine_diff_density_rms 0.154
_database_code_depnum_ccdc_archive 'CCDC 933155'