# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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# 
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_2012jms0015-2a-RS-2BrMA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '2-Bromomandelic Acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 Br O3'
_chemical_formula_sum            'C8 H7 Br O3'
_chemical_formula_weight         231.05

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.708(5)
_cell_length_b                   10.8436(10)
_cell_length_c                   14.131(14)
_cell_angle_alpha                96.952(19)
_cell_angle_beta                 93.91(2)
_cell_angle_gamma                90.07(2)
_cell_volume                     866.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1890
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      25.4

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    4.708
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_T_max  0.9544
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3059
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3059
_reflns_number_gt                2248
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0690P)²+0.0000P] where P=(Fo²+2Fc²)/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         3059
_refine_ls_number_parameters     295
_refine_ls_number_restraints     420
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1788
_refine_ls_wR_factor_gt          0.1576
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.139
_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
O13 O 0.9372(7) 0.8260(4) 0.0853(3) 0.0814(12) Uani 1 1 d U . .
H13 H 0.8440 0.7920 0.1157 0.122 Uiso 1 1 calc R A 1
C1 C 0.6982(10) 0.4548(5) 0.2251(3) 0.0617(13) Uani 1 1 d U . .
C2 C 0.7583(10) 0.4870(5) 0.3234(4) 0.0693(15) Uani 1 1 d U . .
C3 C 0.6443(14) 0.4350(6) 0.3907(4) 0.0888(18) Uani 1 1 d U . .
H4 H 0.6926 0.4551 0.4549 0.107 Uiso 1 1 calc R . .
C4 C 0.4636(14) 0.3554(6) 0.3663(5) 0.094(2) Uani 1 1 d U . .
H5 H 0.3875 0.3216 0.4134 0.113 Uiso 1 1 calc R . .
C5 C 0.3911(13) 0.3241(7) 0.2714(5) 0.095(2) Uani 1 1 d U . .
H6 H 0.2630 0.2711 0.2542 0.114 Uiso 1 1 calc R . .
C6 C 0.5107(11) 0.3723(6) 0.2018(4) 0.0779(17) Uani 1 1 d U . .
H7 H 0.4642 0.3487 0.1378 0.093 Uiso 1 1 calc R . .
C7 C 0.8212(10) 0.5073(5) 0.1486(4) 0.0650(14) Uani 1 1 d U . .
H2 H 0.9812 0.5306 0.1741 0.078 Uiso 1 1 calc R . .
C8 C 0.8381(10) 0.4120(5) 0.0611(4) 0.0651(14) Uani 1 1 d U . .
Br1 Br 0.99855(15) 0.60609(7) 0.36180(5) 0.1107(4) Uani 1 1 d U . .
O3 O 0.7072(8) 0.6164(3) 0.1220(3) 0.0756(11) Uani 1 1 d U . .
H3 H 0.5960 0.5964 0.0833 0.113 Uiso 1 1 calc R . .
O2 O 0.7343(7) 0.4185(4) -0.0147(3) 0.0776(12) Uani 1 1 d U . .
O1 O 0.9807(7) 0.3215(4) 0.0810(3) 0.0736(11) Uani 1 1 d U . .
H1 H 0.9862 0.2701 0.0336 0.110 Uiso 1 1 calc R . .
C11A C 1.098(2) 0.9431(10) 0.2346(6) 0.069(3) Uani 0.441(2) 1 d PGU B 1
C12A C 1.230(2) 0.9436(11) 0.3211(8) 0.072(3) Uani 0.441(2) 1 d PGU B 1
C13A C 1.178(2) 1.0275(11) 0.3992(6) 0.094(4) Uani 0.441(2) 1 d PGU B 1
H14A H 1.2665 1.0278 0.4571 0.112 Uiso 0.441(2) 1 calc PR B 1
C14A C 0.996(3) 1.1108(11) 0.3908(8) 0.121(6) Uani 0.441(2) 1 d PGU B 1
H15A H 0.9612 1.1669 0.4430 0.145 Uiso 0.441(2) 1 calc PR B 1
C15A C 0.864(2) 1.1103(12) 0.3043(10) 0.126(10) Uani 0.441(2) 1 d PGU B 1
H16A H 0.7415 1.1660 0.2986 0.151 Uiso 0.441(2) 1 calc PR B 1
C16A C 0.915(2) 1.0264(11) 0.2262(7) 0.097(4) Uani 0.441(2) 1 d PGU B 1
H17A H 0.8272 1.0261 0.1683 0.116 Uiso 0.441(2) 1 calc PR B 1
C17A C 1.148(2) 0.8574(13) 0.1443(9) 0.067(3) Uani 0.441(2) 1 d PU B 1
H12A H 1.2203 0.7811 0.1626 0.081 Uiso 0.441(2) 1 calc PR B 1
C18A C 1.311(4) 0.9175(18) 0.0776(18) 0.074(5) Uani 0.441(2) 1 d PU B 1
Br2A Br 1.4808(4) 0.8339(2) 0.33661(16) 0.1025(10) Uani 0.441(2) 1 d PU B 1
O11A O 1.451(2) 1.0060(13) 0.1233(9) 0.106(4) Uani 0.441(2) 1 d PU B 1
H11A H 1.5303 1.0352 0.0850 0.160 Uiso 0.441(2) 1 calc PR B 1
O12A O 1.339(5) 0.883(3) -0.0030(19) 0.126(10) Uani 0.441(2) 1 d PU B 1
C13B C 1.2384(17) 0.9508(8) 0.4028(4) 0.086(3) Uani 0.559(2) 1 d PGU B 2
H14B H 1.2093 0.9971 0.4605 0.103 Uiso 0.559(2) 1 calc PR B 2
C12B C 1.1209(15) 0.9777(7) 0.3184(6) 0.070(3) Uani 0.559(2) 1 d PGU B 2
C11B C 1.1644(15) 0.9084(8) 0.2321(4) 0.062(3) Uani 0.559(2) 1 d PGU B 2
C16B C 1.3255(15) 0.8122(7) 0.2303(5) 0.082(3) Uani 0.559(2) 1 d PGU B 2
H17B H 1.3546 0.7659 0.1725 0.099 Uiso 0.559(2) 1 calc PR B 2
C15B C 1.4430(15) 0.7853(7) 0.3146(7) 0.090(5) Uani 0.559(2) 1 d PGU B 2
H16B H 1.5507 0.7210 0.3134 0.108 Uiso 0.559(2) 1 calc PR B 2
C14B C 1.3995(17) 0.8546(9) 0.4009(5) 0.101(4) Uani 0.559(2) 1 d PGU B 2
H15B H 1.4781 0.8366 0.4573 0.121 Uiso 0.559(2) 1 calc PR B 2
C17B C 1.049(2) 0.9349(10) 0.1356(7) 0.069(2) Uani 0.559(2) 1 d PU B 2
H12B H 0.9350 1.0022 0.1448 0.083 Uiso 0.559(2) 1 calc PR B 2
C18B C 1.234(3) 0.9698(14) 0.0763(11) 0.075(4) Uani 0.559(2) 1 d PU B 2
Br2B Br 0.9032(4) 1.10742(18) 0.32603(15) 0.1062(8) Uani 0.559(2) 1 d PU B 2
O11B O 1.3381(19) 1.0743(8) 0.1030(7) 0.093(3) Uani 0.559(2) 1 d PU B 2
H11B H 1.4398 1.0850 0.0664 0.140 Uiso 0.559(2) 1 calc PR B 2
O12B O 1.267(3) 0.9075(15) 0.0020(10) 0.064(3) Uani 0.559(2) 1 d PU B 2


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O13 C17B 1.428(10) . ?
O13 C17A 1.432(14) . ?
O13 H13 0.8200 . ?
C1 C6 1.391(8) . ?
C1 C2 1.410(7) . ?
C1 C7 1.495(7) . ?
C2 C3 1.363(8) . ?
C2 Br1 1.889(6) . ?
C3 C4 1.343(9) . ?
C3 H4 0.9300 . ?
C4 C5 1.378(9) . ?
C4 H5 0.9300 . ?
C5 C6 1.386(8) . ?
C5 H6 0.9300 . ?
C6 H7 0.9300 . ?
C7 O3 1.429(6) . ?
C7 C8 1.521(7) . ?
C7 H2 0.9800 . ?
C8 O2 1.198(6) . ?
C8 O1 1.319(7) . ?
O3 H3 0.8200 . ?
O1 H1 0.8200 . ?
C11A C12A 1.3900 . ?
C11A C16A 1.3900 . ?
C11A C17A 1.528(15) . ?
C12A C13A 1.3900 . ?
C12A Br2A 1.882(9) . ?
C13A C14A 1.3900 . ?
C13A H14A 0.9300 . ?
C14A C15A 1.3900 . ?
C14A H15A 0.9300 . ?
C15A C16A 1.3900 . ?
C15A H16A 0.9300 . ?
C16A H17A 0.9300 . ?
C17A C18A 1.56(3) . ?
C17A H12A 0.9800 . ?
C18A O12A 1.18(3) . ?
C18A O11A 1.32(2) . ?
O11A H11A 0.8200 . ?
C13B C12B 1.3900 . ?
C13B C14B 1.3900 . ?
C13B H14B 0.9300 . ?
C12B C11B 1.3900 . ?
C12B Br2B 1.877(6) . ?
C11B C16B 1.3900 . ?
C11B C17B 1.534(12) . ?
C16B C15B 1.3900 . ?
C16B H17B 0.9300 . ?
C15B C14B 1.3900 . ?
C15B H16B 0.9300 . ?
C14B H15B 0.9300 . ?
C17B C18B 1.47(2) . ?
C17B H12B 0.9800 . ?
C18B O12B 1.20(2) . ?
C18B O11B 1.281(17) . ?
O11B H11B 0.8200 . ?

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
C17B O13 C17A 42.1(6) . . ?
C17B O13 H13 114.7 . . ?
C17A O13 H13 109.5 . . ?
C6 C1 C2 116.1(5) . . ?
C6 C1 C7 120.7(5) . . ?
C2 C1 C7 123.2(5) . . ?
C3 C2 C1 121.2(6) . . ?
C3 C2 Br1 119.8(5) . . ?
C1 C2 Br1 119.0(5) . . ?
C4 C3 C2 121.4(6) . . ?
C4 C3 H4 119.3 . . ?
C2 C3 H4 119.3 . . ?
C3 C4 C5 119.9(7) . . ?
C3 C4 H5 120.0 . . ?
C5 C4 H5 120.0 . . ?
C6 C5 C4 119.4(7) . . ?
C6 C5 H6 120.3 . . ?
C4 C5 H6 120.3 . . ?
C5 C6 C1 121.8(6) . . ?
C5 C6 H7 119.1 . . ?
C1 C6 H7 119.1 . . ?
O3 C7 C1 111.2(5) . . ?
O3 C7 C8 110.0(4) . . ?
C1 C7 C8 111.4(4) . . ?
O3 C7 H2 108.0 . . ?
C1 C7 H2 108.0 . . ?
C8 C7 H2 108.0 . . ?
O2 C8 O1 125.3(5) . . ?
O2 C8 C7 124.3(6) . . ?
O1 C8 C7 110.5(5) . . ?
C7 O3 H3 109.5 . . ?
C8 O1 H1 109.5 . . ?
C12A C11A C16A 120.0 . . ?
C12A C11A C17A 123.5(9) . . ?
C16A C11A C17A 116.5(9) . . ?
C11A C12A C13A 120.0 . . ?
C11A C12A Br2A 121.9(6) . . ?
C13A C12A Br2A 118.1(6) . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A H14A 120.0 . . ?
C14A C13A H14A 120.0 . . ?
C13A C14A C15A 120.0 . . ?
C13A C14A H15A 120.0 . . ?
C15A C14A H15A 120.0 . . ?
C14A C15A C16A 120.0 . . ?
C14A C15A H16A 120.0 . . ?
C16A C15A H16A 120.0 . . ?
C15A C16A C11A 120.0 . . ?
C15A C16A H17A 120.0 . . ?
C11A C16A H17A 120.0 . . ?
O13 C17A C18A 104.3(12) . . ?
O13 C17A C11A 111.5(11) . . ?
C18A C17A C11A 113.6(13) . . ?
O13 C17A H12A 109.1 . . ?
C18A C17A H12A 109.1 . . ?
C11A C17A H12A 109.1 . . ?
O12A C18A O11A 119(2) . . ?
O12A C18A C17A 127(2) . . ?
O11A C18A C17A 113.5(18) . . ?
C18A O11A H11A 109.5 . . ?
C12B C13B C14B 120.0 . . ?
C12B C13B H14B 120.0 . . ?
C14B C13B H14B 120.0 . . ?
C11B C12B C13B 120.0 . . ?
C11B C12B Br2B 122.1(5) . . ?
C13B C12B Br2B 117.9(5) . . ?
C12B C11B C16B 120.0 . . ?
C12B C11B C17B 123.3(7) . . ?
C16B C11B C17B 116.7(7) . . ?
C11B C16B C15B 120.0 . . ?
C11B C16B H17B 120.0 . . ?
C15B C16B H17B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H16B 120.0 . . ?
C14B C15B H16B 120.0 . . ?
C15B C14B C13B 120.0 . . ?
C15B C14B H15B 120.0 . . ?
C13B C14B H15B 120.0 . . ?
O13 C17B C18B 106.5(9) . . ?
O13 C17B C11B 111.1(8) . . ?
C18B C17B C11B 108.2(10) . . ?
O13 C17B H12B 110.3 . . ?
C18B C17B H12B 110.3 . . ?
C11B C17B H12B 110.3 . . ?
O12B C18B O11B 123.0(17) . . ?
O12B C18B C17B 120.1(15) . . ?
O11B C18B C17B 116.5(13) . . ?
C18B O11B H11B 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
C6 C1 C2 C3 2.9(8) . . . . ?
C7 C1 C2 C3 -178.8(6) . . . . ?
C6 C1 C2 Br1 -176.3(4) . . . . ?
C7 C1 C2 Br1 2.1(7) . . . . ?
C1 C2 C3 C4 -3.0(10) . . . . ?
Br1 C2 C3 C4 176.1(5) . . . . ?
C2 C3 C4 C5 0.5(11) . . . . ?
C3 C4 C5 C6 2.0(11) . . . . ?
C4 C5 C6 C1 -2.1(11) . . . . ?
C2 C1 C6 C5 -0.3(9) . . . . ?
C7 C1 C6 C5 -178.8(6) . . . . ?
C6 C1 C7 O3 86.6(6) . . . . ?
C2 C1 C7 O3 -91.7(6) . . . . ?
C6 C1 C7 C8 -36.6(8) . . . . ?
C2 C1 C7 C8 145.1(5) . . . . ?
O3 C7 C8 O2 -12.4(8) . . . . ?
C1 C7 C8 O2 111.5(6) . . . . ?
O3 C7 C8 O1 168.1(5) . . . . ?
C1 C7 C8 O1 -68.0(6) . . . . ?
C16A C11A C12A C13A 0.0 . . . . ?
C17A C11A C12A C13A 177.7(13) . . . . ?
C16A C11A C12A Br2A -179.5(10) . . . . ?
C17A C11A C12A Br2A -1.8(11) . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
Br2A C12A C13A C14A 179.5(10) . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C13A C14A C15A C16A 0.0 . . . . ?
C14A C15A C16A C11A 0.0 . . . . ?
C12A C11A C16A C15A 0.0 . . . . ?
C17A C11A C16A C15A -177.9(12) . . . . ?
C17B O13 C17A C18A -75.8(13) . . . . ?
C17B O13 C17A C11A 47.2(10) . . . . ?
C12A C11A C17A O13 149.2(9) . . . . ?
C16A C11A C17A O13 -33.0(14) . . . . ?
C12A C11A C17A C18A -93.2(14) . . . . ?
C16A C11A C17A C18A 84.6(14) . . . . ?
O13 C17A C18A O12A -42(3) . . . . ?
C11A C17A C18A O12A -164(2) . . . . ?
O13 C17A C18A O11A 147.1(14) . . . . ?
C11A C17A C18A O11A 25(2) . . . . ?
C14B C13B C12B C11B 0.0 . . . . ?
C14B C13B C12B Br2B 179.3(7) . . . . ?
C13B C12B C11B C16B 0.0 . . . . ?
Br2B C12B C11B C16B -179.3(8) . . . . ?
C13B C12B C11B C17B -177.8(10) . . . . ?
Br2B C12B C11B C17B 2.9(8) . . . . ?
C12B C11B C16B C15B 0.0 . . . . ?
C17B C11B C16B C15B 178.0(9) . . . . ?
C11B C16B C15B C14B 0.0 . . . . ?
C16B C15B C14B C13B 0.0 . . . . ?
C12B C13B C14B C15B 0.0 . . . . ?
C17A O13 C17B C18B 78.7(13) . . . . ?
C17A O13 C17B C11B -38.9(10) . . . . ?
C12B C11B C17B O13 -126.6(7) . . . . ?
C16B C11B C17B O13 55.5(10) . . . . ?
C12B C11B C17B C18B 116.8(9) . . . . ?
C16B C11B C17B C18B -61.1(11) . . . . ?
O13 C17B C18B O12B -1.2(19) . . . . ?
C11B C17B C18B O12B 118.3(15) . . . . ?
O13 C17B C18B O11B 171.8(11) . . . . ?
C11B C17B C18B O11B -68.7(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 1007650'
#######################################################################
#
#                 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_2012gjt0004a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 F O3'
_chemical_formula_sum            'C8 H7 F O3'
_chemical_formula_weight         170.14

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1888(12)
_cell_length_b                   10.1998(14)
_cell_length_c                   9.2654(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.709(7)
_cell_angle_gamma                90.00
_cell_volume                     773.02(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7074
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9899
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b5 (Rigaku, 2012)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'


_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9704
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.45
_reflns_number_total             1752
_reflns_number_gt                1268
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b5 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b5 (Rigaku, 2012)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0916P)²+0.4411P] where P=(Fo²+2Fc²)/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         1752
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1743
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
F1 F 0.3374(2) 0.96674(18) 0.09770(17) 0.0466(5) Uani 1 1 d . . .
O2 O 0.0711(2) 0.89246(16) 0.37748(17) 0.0287(4) Uani 1 1 d . . .
H2 H 0.0328 0.8164 0.3681 0.043 Uiso 1 1 calc R . .
O3 O 0.0708(2) 1.16460(15) 0.13413(17) 0.0263(4) Uani 1 1 d . . .
H3A H 0.0631 1.1110 0.0653 0.039 Uiso 1 1 calc R . .
O1 O -0.0247(2) 0.91361(16) 0.14893(17) 0.0322(5) Uani 1 1 d . . .
C1 C 0.2973(3) 1.0993(2) 0.2982(2) 0.0235(5) Uani 1 1 d . . .
C7 C 0.1149(3) 1.0964(2) 0.2646(2) 0.0217(5) Uani 1 1 d . . .
H7 H 0.0612 1.1423 0.3452 0.026 Uiso 1 1 calc R . .
C8 C 0.0463(3) 0.9572(2) 0.2558(2) 0.0233(5) Uani 1 1 d . . .
C2 C 0.4040(3) 1.0336(2) 0.2118(3) 0.0282(5) Uani 1 1 d . . .
C6 C 0.3660(3) 1.1687(2) 0.4155(3) 0.0300(6) Uani 1 1 d . . .
H6 H 0.2969 1.2152 0.4772 0.036 Uiso 1 1 calc R . .
C5 C 0.5338(3) 1.1708(3) 0.4435(3) 0.0346(6) Uani 1 1 d . . .
H5 H 0.5789 1.2185 0.5239 0.042 Uiso 1 1 calc R . .
C3 C 0.5707(3) 1.0337(3) 0.2360(3) 0.0372(6) Uani 1 1 d . . .
H3 H 0.6396 0.9874 0.1739 0.045 Uiso 1 1 calc R . .
C4 C 0.6356(3) 1.1034(3) 0.3543(3) 0.0382(6) Uani 1 1 d . . .
H4 H 0.7505 1.1049 0.3740 0.046 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
F1 C2 1.351(3) . ?
O2 C8 1.315(3) . ?
O2 H2 0.8400 . ?
O3 C7 1.426(3) . ?
O3 H3A 0.8400 . ?
O1 C8 1.209(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.511(3) . ?
C7 C8 1.527(3) . ?
C7 H7 1.0000 . ?
C2 C3 1.373(4) . ?
C6 C5 1.387(4) . ?
C6 H6 0.9500 . ?
C5 C4 1.384(4) . ?
C5 H5 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?

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
C8 O2 H2 109.5 . . ?
C7 O3 H3A 109.5 . . ?
C2 C1 C6 117.0(2) . . ?
C2 C1 C7 121.0(2) . . ?
C6 C1 C7 122.0(2) . . ?
O3 C7 C1 111.92(18) . . ?
O3 C7 C8 109.27(17) . . ?
C1 C7 C8 112.74(18) . . ?
O3 C7 H7 107.6 . . ?
C1 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
O1 C8 O2 124.5(2) . . ?
O1 C8 C7 123.2(2) . . ?
O2 C8 C7 112.30(18) . . ?
F1 C2 C3 119.3(2) . . ?
F1 C2 C1 117.0(2) . . ?
C3 C2 C1 123.7(2) . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C2 C3 C4 118.0(2) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?

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
C2 C1 C7 O3 -67.4(3) . . . . ?
C6 C1 C7 O3 111.8(2) . . . . ?
C2 C1 C7 C8 56.2(3) . . . . ?
C6 C1 C7 C8 -124.5(2) . . . . ?
O3 C7 C8 O1 4.2(3) . . . . ?
C1 C7 C8 O1 -120.9(2) . . . . ?
O3 C7 C8 O2 -174.73(18) . . . . ?
C1 C7 C8 O2 60.1(2) . . . . ?
C6 C1 C2 F1 -179.8(2) . . . . ?
C7 C1 C2 F1 -0.5(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C7 C1 C2 C3 179.4(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C7 C1 C6 C5 -179.5(2) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
F1 C2 C3 C4 180.0(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.84 1.76 2.598(2) 171.3 2_545
O3 H3A O1 0.84 2.01 2.750(2) 146.5 3_575

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 1007651'
#######################################################################
#
#                 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_2012jms0026-RS-2IMA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 I O3'
_chemical_formula_sum            'C8 H7 I O3'
_chemical_formula_weight         278.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.805(3)
_cell_length_b                   10.732(6)
_cell_length_c                   13.969(7)
_cell_angle_alpha                96.527(13)
_cell_angle_beta                 92.909(13)
_cell_angle_gamma                90.058(13)
_cell_volume                     863.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2020
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    3.671
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_T_max  0.9642
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10089
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3043
_reflns_number_gt                2305
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0214P)²+6.7385P] where P=(Fo²+2Fc²)/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         3043
_refine_ls_number_parameters     270
_refine_ls_number_restraints     414
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1741(14) -0.0468(7) 0.2208(6) 0.0326(17) Uani 1 1 d U . .
C2 C 0.2303(14) -0.0195(7) 0.3190(6) 0.0315(17) Uani 1 1 d U . .
C3 C 0.1110(15) -0.0711(7) 0.3876(6) 0.0351(18) Uani 1 1 d U . .
H3 H 0.1533 -0.0513 0.4542 0.042 Uiso 1 1 calc R . .
C4 C -0.0681(15) -0.1506(8) 0.3592(6) 0.0384(19) Uani 1 1 d U . .
H4 H -0.1476 -0.1892 0.4059 0.046 Uiso 1 1 calc R . .
C5 C -0.1348(16) -0.1755(8) 0.2629(6) 0.042(2) Uani 1 1 d U . .
H5 H -0.2650 -0.2277 0.2435 0.050 Uiso 1 1 calc R . .
C6 C -0.0125(14) -0.1248(7) 0.1950(6) 0.0336(18) Uani 1 1 d U . .
H6 H -0.0578 -0.1439 0.1286 0.040 Uiso 1 1 calc R . .
C7 C 0.3070(13) 0.0094(7) 0.1463(6) 0.0299(16) Uani 1 1 d U . .
H7 H 0.4647 0.0327 0.1750 0.036 Uiso 1 1 calc R . .
C8 C 0.3324(14) -0.0856(7) 0.0577(6) 0.0305(17) Uani 1 1 d U . .
I1 I 0.49127(11) 0.11210(5) 0.36890(5) 0.0476(2) Uani 1 1 d U . .
O1 O 0.4736(9) -0.1764(5) 0.0789(4) 0.0357(14) Uani 1 1 d U . .
H1 H 0.4857 -0.2285 0.0298 0.054 Uiso 1 1 calc R . .
O2 O 0.2364(9) -0.0804(5) -0.0206(4) 0.0343(13) Uani 1 1 d U . .
O3 O 0.1996(10) 0.1190(5) 0.1185(4) 0.0361(14) Uani 1 1 d U . .
H3A H 0.0701 0.1002 0.0910 0.054 Uiso 1 1 calc R . .
I2A I 0.3764(3) 0.62478(13) 0.33293(12) 0.0533(4) Uani 0.50 1 d PU A 2
C11A C 0.620(2) 0.4804(11) 0.3190(8) 0.035(4) Uani 0.50 1 d PGU A 2
C12A C 0.741(2) 0.4526(11) 0.4022(7) 0.039(3) Uani 0.50 1 d PGU A 2
H12A H 0.7131 0.4986 0.4626 0.047 Uiso 0.50 1 calc PR A 2
C13A C 0.904(2) 0.3575(12) 0.3969(8) 0.047(3) Uani 0.50 1 d PGU A 2
H13A H 0.9872 0.3386 0.4538 0.057 Uiso 0.50 1 calc PR A 2
C14A C 0.945(2) 0.2902(10) 0.3085(10) 0.054(4) Uani 0.50 1 d PGU A 2
H14A H 1.0567 0.2252 0.3049 0.065 Uiso 0.50 1 calc PR A 2
C15A C 0.824(2) 0.3180(11) 0.2254(8) 0.040(4) Uani 0.50 1 d PGU A 2
H15A H 0.8520 0.2720 0.1650 0.048 Uiso 0.50 1 calc PR A 2
C16A C 0.661(2) 0.4131(12) 0.2306(7) 0.035(3) Uani 0.50 1 d PGU A 2
C17A C 0.547(3) 0.4356(16) 0.1369(12) 0.035(3) Uani 0.50 1 d PU A 2
H17A H 0.4311 0.5039 0.1467 0.042 Uiso 0.50 1 calc PR A 2
O11A O 0.827(2) 0.5830(11) 0.1021(9) 0.046(2) Uani 0.50 1 d PU A 2
H11A H 0.9292 0.5975 0.0645 0.068 Uiso 0.50 1 calc PR A 2
C18A C 0.737(3) 0.4751(18) 0.0752(12) 0.032(4) Uani 0.50 1 d PU A 2
O12A O 0.790(14) 0.416(5) 0.002(4) 0.055(6) Uani 0.50 1 d PU A 2
I2B I 0.9813(2) 0.33786(12) 0.34632(10) 0.0372(3) Uani 0.50 1 d PU A -1
C11B C 0.7022(19) 0.4539(11) 0.3192(8) 0.034(4) Uani 0.50 1 d PGU A -1
C12B C 0.632(2) 0.5358(11) 0.3964(7) 0.039(3) Uani 0.50 1 d PGU A -1
H12B H 0.7138 0.5399 0.4573 0.047 Uiso 0.50 1 calc PR A -1
C13B C 0.441(2) 0.6117(11) 0.3845(8) 0.047(3) Uani 0.50 1 d PGU A -1
H13B H 0.3925 0.6676 0.4372 0.057 Uiso 0.50 1 calc PR A -1
C14B C 0.321(2) 0.6056(12) 0.2955(10) 0.054(4) Uani 0.50 1 d PGU A -1
H14B H 0.1901 0.6575 0.2873 0.065 Uiso 0.50 1 calc PR A -1
C15B C 0.391(2) 0.5238(12) 0.2183(8) 0.049(4) Uani 0.50 1 d PGU A -1
H15B H 0.3090 0.5196 0.1574 0.058 Uiso 0.50 1 calc PR A -1
C16B C 0.582(2) 0.4479(11) 0.2302(7) 0.024(3) Uani 0.50 1 d PGU A -1
C17B C 0.649(3) 0.3611(15) 0.1470(11) 0.028(3) Uani 0.50 1 d PU A -1
H17B H 0.7191 0.2846 0.1706 0.033 Uiso 0.50 1 calc PR A -1
C18B C 0.812(3) 0.4153(15) 0.0810(12) 0.025(3) Uani 0.50 1 d PU A -1
O11B O 0.944(2) 0.4989(11) 0.1249(9) 0.046(2) Uani 0.50 1 d PU A -1
H11B H 1.0304 0.5264 0.0856 0.068 Uiso 0.50 1 calc PR A -1
O12B O 0.801(14) 0.386(5) -0.005(4) 0.055(6) Uani 0.50 1 d PU A -1
O13 O 0.4406(10) 0.3243(5) 0.0843(4) 0.0390(14) Uani 1 1 d U . .
H13 H 0.3349 0.2989 0.1163 0.058 Uiso 1 1 calc R A 2


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.376(11) . ?
C1 C2 1.391(11) . ?
C1 C7 1.506(12) . ?
C2 C3 1.375(12) . ?
C2 I1 2.108(8) . ?
C3 C4 1.359(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(12) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O3 1.416(9) . ?
C7 C8 1.524(11) . ?
C7 H7 1.0000 . ?
C8 O2 1.209(9) . ?
C8 O1 1.324(9) . ?
O1 H1 0.8400 . ?
O3 H3A 0.8400 . ?
I2A C11A 2.097(8) . ?
C11A C12A 1.3900 . ?
C11A C16A 1.3900 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3900 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3900 . ?
C14A H14A 0.9500 . ?
C15A C16A 1.3900 . ?
C15A H15A 0.9500 . ?
C16A C17A 1.480(19) . ?
C17A O13 1.450(17) . ?
C17A C18A 1.52(2) . ?
C17A H17A 1.0000 . ?
O11A C18A 1.28(2) . ?
O11A H11A 0.8400 . ?
C18A O12A 1.20(4) . ?
I2B C11B 2.090(8) . ?
C11B C12B 1.3900 . ?
C11B C16B 1.3900 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3900 . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3900 . ?
C15B H15B 0.9500 . ?
C16B C17B 1.472(17) . ?
C17B O13 1.481(17) . ?
C17B C18B 1.51(2) . ?
C17B H17B 1.0000 . ?
C18B O12B 1.20(5) . ?
C18B O11B 1.26(2) . ?
O11B H11B 0.8400 . ?
O13 H13 0.8400 . ?

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
C6 C1 C2 117.0(8) . . ?
C6 C1 C7 121.5(7) . . ?
C2 C1 C7 121.6(7) . . ?
C3 C2 C1 122.0(8) . . ?
C3 C2 I1 117.1(6) . . ?
C1 C2 I1 120.8(6) . . ?
C4 C3 C2 119.3(8) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.2(9) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.8(9) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 121.6(8) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O3 C7 C1 111.5(7) . . ?
O3 C7 C8 109.7(6) . . ?
C1 C7 C8 110.6(6) . . ?
O3 C7 H7 108.3 . . ?
C1 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
O2 C8 O1 124.4(8) . . ?
O2 C8 C7 125.4(7) . . ?
O1 C8 C7 110.2(7) . . ?
C8 O1 H1 109.5 . . ?
C7 O3 H3A 109.5 . . ?
C12A C11A C16A 120.0 . . ?
C12A C11A I2A 117.7(6) . . ?
C16A C11A I2A 122.3(6) . . ?
C13A C12A C11A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C14A C13A C12A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C15A C14A C13A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C14A C15A C16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A C11A 120.0 . . ?
C15A C16A C17A 114.8(10) . . ?
C11A C16A C17A 125.1(10) . . ?
O13 C17A C16A 113.5(13) . . ?
O13 C17A C18A 106.3(12) . . ?
C16A C17A C18A 106.4(14) . . ?
O13 C17A H17A 110.1 . . ?
C16A C17A H17A 110.1 . . ?
C18A C17A H17A 110.1 . . ?
C18A O11A H11A 109.5 . . ?
O12A C18A O11A 121(3) . . ?
O12A C18A C17A 124(3) . . ?
O11A C18A C17A 115.5(15) . . ?
C12B C11B C16B 120.0 . . ?
C12B C11B I2B 117.0(6) . . ?
C16B C11B I2B 122.9(6) . . ?
C11B C12B C13B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C14B C13B C12B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C14B C15B 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C15B C16B C11B 120.0 . . ?
C15B C16B C17B 118.2(9) . . ?
C11B C16B C17B 121.8(9) . . ?
C16B C17B O13 109.2(11) . . ?
C16B C17B C18B 115.3(13) . . ?
O13 C17B C18B 104.5(12) . . ?
C16B C17B H17B 109.2 . . ?
O13 C17B H17B 109.2 . . ?
C18B C17B H17B 109.2 . . ?
O12B C18B O11B 125(3) . . ?
O12B C18B C17B 122(3) . . ?
O11B C18B C17B 112.8(14) . . ?
C18B O11B H11B 109.5 . . ?
C17A O13 C17B 40.3(8) . . ?
C17A O13 H13 109.5 . . ?
C17B O13 H13 111.2 . . ?

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
C6 C1 C2 C3 2.2(11) . . . . ?
C7 C1 C2 C3 -179.5(7) . . . . ?
C6 C1 C2 I1 -174.0(6) . . . . ?
C7 C1 C2 I1 4.2(10) . . . . ?
C1 C2 C3 C4 -0.4(12) . . . . ?
I1 C2 C3 C4 176.1(6) . . . . ?
C2 C3 C4 C5 -2.5(12) . . . . ?
C3 C4 C5 C6 3.3(13) . . . . ?
C4 C5 C6 C1 -1.3(13) . . . . ?
C2 C1 C6 C5 -1.4(12) . . . . ?
C7 C1 C6 C5 -179.6(7) . . . . ?
C6 C1 C7 O3 83.2(9) . . . . ?
C2 C1 C7 O3 -94.9(9) . . . . ?
C6 C1 C7 C8 -39.2(10) . . . . ?
C2 C1 C7 C8 142.7(7) . . . . ?
O3 C7 C8 O2 -13.8(11) . . . . ?
C1 C7 C8 O2 109.6(9) . . . . ?
O3 C7 C8 O1 167.0(6) . . . . ?
C1 C7 C8 O1 -69.6(8) . . . . ?
C16A C11A C12A C13A 0.0 . . . . ?
I2A C11A C12A C13A 179.8(10) . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C13A C14A C15A C16A 0.0 . . . . ?
C14A C15A C16A C11A 0.0 . . . . ?
C14A C15A C16A C17A 178.6(14) . . . . ?
C12A C11A C16A C15A 0.0 . . . . ?
I2A C11A C16A C15A -179.8(11) . . . . ?
C12A C11A C16A C17A -178.4(15) . . . . ?
I2A C11A C16A C17A 1.8(13) . . . . ?
C15A C16A C17A O13 54.9(16) . . . . ?
C11A C16A C17A O13 -126.6(11) . . . . ?
C15A C16A C17A C18A -61.7(15) . . . . ?
C11A C16A C17A C18A 116.8(13) . . . . ?
O13 C17A C18A O12A -5(6) . . . . ?
C16A C17A C18A O12A 116(5) . . . . ?
O13 C17A C18A O11A 169.2(14) . . . . ?
C16A C17A C18A O11A -69.5(19) . . . . ?
C16B C11B C12B C13B 0.0 . . . . ?
I2B C11B C12B C13B -177.2(10) . . . . ?
C11B C12B C13B C14B 0.0 . . . . ?
C12B C13B C14B C15B 0.0 . . . . ?
C13B C14B C15B C16B 0.0 . . . . ?
C14B C15B C16B C11B 0.0 . . . . ?
C14B C15B C16B C17B 179.1(13) . . . . ?
C12B C11B C16B C15B 0.0 . . . . ?
I2B C11B C16B C15B 177.0(10) . . . . ?
C12B C11B C16B C17B -179.1(14) . . . . ?
I2B C11B C16B C17B -2.1(13) . . . . ?
C15B C16B C17B O13 -29.1(15) . . . . ?
C11B C16B C17B O13 149.9(9) . . . . ?
C15B C16B C17B C18B 88.1(15) . . . . ?
C11B C16B C17B C18B -92.8(15) . . . . ?
C16B C17B C18B O12B -145(5) . . . . ?
O13 C17B C18B O12B -25(5) . . . . ?
C16B C17B C18B O11B 30(2) . . . . ?
O13 C17B C18B O11B 150.0(13) . . . . ?
C16A C17A O13 C17B -37.3(13) . . . . ?
C18A C17A O13 C17B 79.4(16) . . . . ?
C16B C17B O13 C17A 44.4(13) . . . . ?
C18B C17B O13 C17A -79.4(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.917
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.148
_database_code_depnum_ccdc_archive 'CCDC 1007652'
#######################################################################
#
#                 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_race2methylma-RS-2MeMA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 O6'
_chemical_formula_sum            'C18 H20 O6'
_chemical_formula_weight         332.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.833(5)
_cell_length_b                   9.263(5)
_cell_length_c                   10.750(5)
_cell_angle_alpha                73.230(5)
_cell_angle_beta                 81.067(5)
_cell_angle_gamma                77.849(5)
_cell_volume                     819.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9819
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            light_yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16751
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3744
_reflns_number_gt                2824
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0567P)²+0.1844P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3744
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O3 O 1.54756(15) 0.33106(13) 1.43727(11) 0.0342(3) Uani 1 1 d . . .
H2 H 1.5546 0.3641 1.5008 0.051 Uiso 1 1 calc R . .
O5 O 1.48538(12) 0.19447(12) 0.95724(10) 0.0264(3) Uani 1 1 d . . .
O6 O 1.29689(12) 0.05204(12) 1.02405(11) 0.0265(3) Uani 1 1 d . . .
H9 H 1.3728 -0.0206 1.0292 0.040 Uiso 1 1 calc R . .
O2 O 1.41897(13) 0.56876(12) 1.36165(10) 0.0272(3) Uani 1 1 d . . .
O4 O 1.27431(13) 0.45769(12) 0.92207(10) 0.0245(3) Uani 1 1 d . . .
H7 H 1.2983 0.4751 0.9883 0.037 Uiso 1 1 calc R . .
O1 O 1.38739(12) 0.51210(12) 1.13344(9) 0.0235(3) Uani 1 1 d . . .
H1 H 1.4472 0.5767 1.1127 0.035 Uiso 1 1 calc R . .
C12 C 0.91805(18) 0.23849(17) 0.77800(14) 0.0230(3) Uani 1 1 d . . .
H12 H 0.8244 0.1979 0.7958 0.028 Uiso 1 1 calc R . .
C7 C 1.33084(18) 0.27606(17) 1.27647(13) 0.0222(3) Uani 1 1 d . . .
C15 C 1.18999(18) 0.35647(18) 0.72295(14) 0.0250(4) Uani 1 1 d . . .
H15 H 1.2837 0.3970 0.7040 0.030 Uiso 1 1 calc R . .
C11 C 0.98897(17) 0.24930(16) 0.88183(14) 0.0201(3) Uani 1 1 d . . .
C9 C 1.46858(17) 0.43972(18) 1.35091(14) 0.0228(3) Uani 1 1 d . . .
C6 C 1.17238(18) 0.33879(18) 1.28072(14) 0.0238(3) Uani 1 1 d . . .
H6 H 1.1409 0.4469 1.2592 0.029 Uiso 1 1 calc R . .
C16 C 1.12689(17) 0.30946(16) 0.85247(13) 0.0199(3) Uani 1 1 d . . .
C17 C 1.21567(17) 0.31897(17) 0.95941(14) 0.0212(3) Uani 1 1 d . . .
H17 H 1.1445 0.3140 1.0419 0.025 Uiso 1 1 calc R . .
C14 C 1.11737(19) 0.34467(19) 0.62185(15) 0.0273(4) Uani 1 1 d . . .
H14 H 1.1610 0.3770 0.5340 0.033 Uiso 1 1 calc R . .
C13 C 0.98138(19) 0.28568(18) 0.64969(15) 0.0262(4) Uani 1 1 d . . .
H13 H 0.9310 0.2774 0.5808 0.031 Uiso 1 1 calc R . .
C2 C 1.3790(2) 0.11646(18) 1.31036(14) 0.0277(4) Uani 1 1 d . . .
C8 C 1.44621(18) 0.38630(17) 1.23458(14) 0.0228(3) Uani 1 1 d . . .
H8 H 1.5484 0.3330 1.2013 0.027 Uiso 1 1 calc R . .
C3 C 1.2630(2) 0.02571(19) 1.34600(15) 0.0332(4) Uani 1 1 d . . .
H3 H 1.2929 -0.0826 1.3696 0.040 Uiso 1 1 calc R . .
C10 C 0.91514(18) 0.19787(18) 1.02018(14) 0.0260(4) Uani 1 1 d . . .
H10A H 0.8132 0.1727 1.0188 0.039 Uiso 1 1 calc R . .
H10B H 0.9022 0.2804 1.0630 0.039 Uiso 1 1 calc R . .
H10C H 0.9822 0.1071 1.0684 0.039 Uiso 1 1 calc R . .
C5 C 1.0604(2) 0.24556(19) 1.31597(14) 0.0282(4) Uani 1 1 d . . .
H5 H 0.9530 0.2893 1.3181 0.034 Uiso 1 1 calc R . .
C4 C 1.1067(2) 0.0882(2) 1.34803(15) 0.0324(4) Uani 1 1 d . . .
H4 H 1.0309 0.0233 1.3714 0.039 Uiso 1 1 calc R . .
C1 C 1.5479(2) 0.0419(2) 1.30827(17) 0.0371(4) Uani 1 1 d . . .
H1A H 1.5560 -0.0694 1.3281 0.056 Uiso 1 1 calc R . .
H1B H 1.5963 0.0669 1.3738 0.056 Uiso 1 1 calc R . .
H1C H 1.6015 0.0798 1.2215 0.056 Uiso 1 1 calc R . .
C18 C 1.34755(18) 0.18266(17) 0.98053(13) 0.0210(3) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O3 C9 1.3145(19) . ?
O3 H2 0.8400 . ?
O5 C18 1.2258(19) . ?
O6 C18 1.3112(19) . ?
O6 H9 0.8400 . ?
O2 C9 1.2155(19) . ?
O4 C17 1.4137(19) . ?
O4 H7 0.8400 . ?
O1 C8 1.4139(18) . ?
O1 H1 0.8400 . ?
C12 C13 1.386(2) . ?
C12 C11 1.399(2) . ?
C12 H12 0.9500 . ?
C7 C6 1.397(2) . ?
C7 C2 1.404(2) . ?
C7 C8 1.521(2) . ?
C15 C14 1.385(2) . ?
C15 C16 1.397(2) . ?
C15 H15 0.9500 . ?
C11 C16 1.400(2) . ?
C11 C10 1.512(2) . ?
C9 C8 1.524(2) . ?
C6 C5 1.386(2) . ?
C6 H6 0.9500 . ?
C16 C17 1.520(2) . ?
C17 C18 1.517(2) . ?
C17 H17 1.0000 . ?
C14 C13 1.379(2) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?
C2 C3 1.399(2) . ?
C2 C1 1.506(3) . ?
C8 H8 1.0000 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5 C4 1.383(3) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O3 H2 109.5 . . ?
C18 O6 H9 109.5 . . ?
C17 O4 H7 109.5 . . ?
C8 O1 H1 109.5 . . ?
C13 C12 C11 121.47(14) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C6 C7 C2 120.14(14) . . ?
C6 C7 C8 117.66(14) . . ?
C2 C7 C8 122.20(15) . . ?
C14 C15 C16 120.72(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C12 C11 C16 117.92(13) . . ?
C12 C11 C10 119.73(13) . . ?
C16 C11 C10 122.35(13) . . ?
O2 C9 O3 124.16(14) . . ?
O2 C9 C8 123.39(13) . . ?
O3 C9 C8 112.44(13) . . ?
C5 C6 C7 120.94(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C15 C16 C11 120.22(13) . . ?
C15 C16 C17 118.22(13) . . ?
C11 C16 C17 121.51(12) . . ?
O4 C17 C18 110.67(12) . . ?
O4 C17 C16 110.11(11) . . ?
C18 C17 C16 107.65(12) . . ?
O4 C17 H17 109.5 . . ?
C18 C17 H17 109.5 . . ?
C16 C17 H17 109.5 . . ?
C13 C14 C15 119.52(14) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C13 C12 120.14(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C3 C2 C7 117.43(16) . . ?
C3 C2 C1 119.91(15) . . ?
C7 C2 C1 122.66(15) . . ?
O1 C8 C7 108.45(12) . . ?
O1 C8 C9 110.66(13) . . ?
C7 C8 C9 109.67(12) . . ?
O1 C8 H8 109.3 . . ?
C7 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C4 C3 C2 122.23(16) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C6 119.38(16) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C3 C4 C5 119.86(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O5 C18 O6 124.34(14) . . ?
O5 C18 C17 123.37(13) . . ?
O6 C18 C17 112.29(13) . . ?

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 H2 O2 0.84 1.82 2.6631(18) 176.9 2_868
O6 H9 O5 0.84 1.80 2.6381(18) 171.4 2_857
O4 H7 O1 0.84 1.99 2.8271(18) 171.6 .
O1 H1 O5 0.84 2.21 3.003(2) 157.2 2_867
O1 H1 O4 0.84 2.40 3.011(2) 130.4 2_867

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 1007653'
#######################################################################
#
#                 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_2011jms0002m-RS-3BrMA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 Br O3'
_chemical_formula_sum            'C8 H7 Br O3'
_chemical_formula_weight         231.05

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8529(7)
_cell_length_b                   8.9210(6)
_cell_length_c                   10.7745(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.568(6)
_cell_angle_gamma                90.00
_cell_volume                     850.89(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4043
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    4.792
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7619
_exptl_absorpt_correction_T_max  0.8696
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Left): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4482
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1949
_reflns_number_gt                1770
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0259P)²+0.7296P] where P=(Fo²+2Fc²)/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         1949
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.69869(2) 0.18029(2) 0.01064(2) 0.03108(10) Uani 1 1 d . . .
O1 O 0.09270(16) 0.38377(16) 0.11545(12) 0.0200(3) Uani 1 1 d . . .
H1 H 0.0749 0.3695 0.1910 0.030 Uiso 1 1 calc R . .
O3 O 0.08602(17) 0.13754(16) -0.14547(12) 0.0211(3) Uani 1 1 d . . .
H3 H 0.0420 0.0777 -0.0977 0.032 Uiso 1 1 calc R . .
O2 O 0.04929(16) 0.13651(16) 0.10096(13) 0.0189(3) Uani 1 1 d . . .
C3 C 0.5388(2) 0.2889(2) -0.06631(19) 0.0200(4) Uani 1 1 d . . .
C1 C 0.2741(2) 0.3247(2) -0.10232(17) 0.0159(4) Uani 1 1 d . . .
C8 C 0.0810(2) 0.2558(2) 0.05489(17) 0.0153(4) Uani 1 1 d . . .
C7 C 0.1124(2) 0.2755(2) -0.08264(17) 0.0160(4) Uani 1 1 d . . .
H2 H 0.0427 0.3535 -0.1173 0.019 Uiso 1 1 calc R . .
C5 C 0.4558(3) 0.4882(3) -0.1962(2) 0.0273(5) Uani 1 1 d . . .
H6 H 0.4775 0.5717 -0.2477 0.033 Uiso 1 1 calc R . .
C2 C 0.3915(2) 0.2447(2) -0.04549(18) 0.0182(4) Uani 1 1 d . . .
H4 H 0.3705 0.1614 0.0065 0.022 Uiso 1 1 calc R . .
C6 C 0.3064(2) 0.4466(2) -0.17702(18) 0.0218(4) Uani 1 1 d . . .
H7 H 0.2266 0.5017 -0.2151 0.026 Uiso 1 1 calc R . .
C4 C 0.5730(2) 0.4094(2) -0.14094(19) 0.0245(4) Uani 1 1 d . . .
H5 H 0.6750 0.4377 -0.1542 0.029 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Br1 C3 1.899(2) . ?
O1 C8 1.318(2) . ?
O1 H1 0.8400 . ?
O3 C7 1.422(2) . ?
O3 H3 0.8400 . ?
O2 C8 1.209(2) . ?
C3 C4 1.378(3) . ?
C3 C2 1.382(3) . ?
C1 C6 1.385(3) . ?
C1 C2 1.397(3) . ?
C1 C7 1.515(3) . ?
C8 C7 1.520(2) . ?
C7 H2 1.0000 . ?
C5 C4 1.384(3) . ?
C5 C6 1.391(3) . ?
C5 H6 0.9500 . ?
C2 H4 0.9500 . ?
C6 H7 0.9500 . ?
C4 H5 0.9500 . ?

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
C8 O1 H1 109.5 . . ?
C7 O3 H3 109.5 . . ?
C4 C3 C2 122.02(19) . . ?
C4 C3 Br1 119.04(16) . . ?
C2 C3 Br1 118.94(16) . . ?
C6 C1 C2 119.96(18) . . ?
C6 C1 C7 120.63(18) . . ?
C2 C1 C7 119.41(16) . . ?
O2 C8 O1 125.22(17) . . ?
O2 C8 C7 123.16(17) . . ?
O1 C8 C7 111.62(16) . . ?
O3 C7 C1 109.56(15) . . ?
O3 C7 C8 109.48(15) . . ?
C1 C7 C8 110.60(15) . . ?
O3 C7 H2 109.1 . . ?
C1 C7 H2 109.1 . . ?
C8 C7 H2 109.1 . . ?
C4 C5 C6 120.73(19) . . ?
C4 C5 H6 119.6 . . ?
C6 C5 H6 119.6 . . ?
C3 C2 C1 118.82(18) . . ?
C3 C2 H4 120.6 . . ?
C1 C2 H4 120.6 . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 H7 120.1 . . ?
C5 C6 H7 120.1 . . ?
C3 C4 C5 118.64(19) . . ?
C3 C4 H5 120.7 . . ?
C5 C4 H5 120.7 . . ?

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
C6 C1 C7 O3 109.2(2) . . . . ?
C2 C1 C7 O3 -70.1(2) . . . . ?
C6 C1 C7 C8 -130.06(18) . . . . ?
C2 C1 C7 C8 50.7(2) . . . . ?
O2 C8 C7 O3 4.8(2) . . . . ?
O1 C8 C7 O3 -175.14(15) . . . . ?
O2 C8 C7 C1 -116.03(19) . . . . ?
O1 C8 C7 C1 64.0(2) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
Br1 C3 C2 C1 -179.93(14) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C7 C1 C2 C3 178.65(17) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C7 C1 C6 C5 -178.63(18) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
Br1 C3 C4 C5 -179.70(16) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.208
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.080
_database_code_depnum_ccdc_archive 'CCDC 1007654'
#######################################################################
#
#                 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_3br_una
_audit_creation_date             2014-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H7 Br O3'
_chemical_formula_sum            'C8 H7 Br1 O3 '
_chemical_formula_weight         231.05
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.8285(5)
_cell_length_b                   9.3102(7)
_cell_length_c                   10.4698(7)
_cell_angle_alpha                92.436(8)
_cell_angle_beta                 90.260(8)
_cell_angle_gamma                94.119(8)
_cell_volume                     857.54(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_exptl_absorpt_coefficient_mu    4.755
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10931
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.87
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.011639
_diffrn_orient_matrix_UB_12      -0.029307
_diffrn_orient_matrix_UB_13      -0.109100
_diffrn_orient_matrix_UB_21      -0.077963
_diffrn_orient_matrix_UB_22      0.071939
_diffrn_orient_matrix_UB_23      -0.019095
_diffrn_orient_matrix_UB_31      0.062787
_diffrn_orient_matrix_UB_32      0.067409
_diffrn_orient_matrix_UB_33      -0.025564
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2551
_reflns_number_total             3907
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-1997 (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0307P)²+0.7511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C107(H107)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C102(H102), C104(H104), C105(H105), C106(H106)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O101(H101), O103(H103)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 1.19602(5) 0.67902(6) 0.55040(6) 0.03553(17) Uani 1 d . . .
O1 O 0.5764(3) 0.6489(3) 0.6506(3) 0.0169(7) Uani 1 d . . .
H1 H 0.5496 0.5816 0.5975 0.025 Uiso 1 calc . . GR
O2 O 0.5357(3) 0.6327(3) 0.3971(3) 0.0220(7) Uani 1 d . . .
O3 O 0.5738(3) 0.8726(3) 0.3816(3) 0.0204(7) Uani 1 d . . .
H3 H 0.5525 0.8536 0.3042 0.031 Uiso 1 calc . . GR
C1 C 0.7713(5) 0.8362(5) 0.6053(4) 0.0154(9) Uani 1 d . . .
C2 C 0.8868(5) 0.7473(5) 0.5747(4) 0.0166(10) Uani 1 d . . .
H2 H 0.8635 0.6526 0.5395 0.020 Uiso 1 calc . . R
C3 C 1.0368(5) 0.7986(5) 0.5962(4) 0.0198(10) Uani 1 d . . .
C4 C 1.0746(5) 0.9354(5) 0.6490(4) 0.0230(11) Uani 1 d . . .
H4 H 1.1776 0.9681 0.6649 0.028 Uiso 1 calc . . R
C5 C 0.9586(5) 1.0232(5) 0.6780(4) 0.0235(11) Uani 1 d . . .
H5 H 0.9824 1.1180 0.7130 0.028 Uiso 1 calc . . R
C6 C 0.8067(5) 0.9744(5) 0.6566(4) 0.0202(10) Uani 1 d . . .
H6 H 0.7280 1.0357 0.6772 0.024 Uiso 1 calc . . R
C7 C 0.6058(4) 0.7788(5) 0.5855(4) 0.0141(9) Uani 1 d . . .
H7 H 0.5388 0.8523 0.6216 0.017 Uiso 1 calc . . R
C8 C 0.5676(4) 0.7516(5) 0.4441(4) 0.0160(10) Uani 1 d . . .
Br11 Br 1.17232(5) 0.17969(6) 1.02839(6) 0.03408(17) Uani 1 d . . .
O101 O 0.5486(3) 0.1494(3) 0.8475(3) 0.0193(7) Uani 1 d . . .
H101 H 0.5345 0.0800 0.8959 0.029 Uiso 1 calc . . GR
O102 O 0.5274(3) 0.1386(3) 1.1048(3) 0.0213(7) Uani 1 d . . .
O103 O 0.5590(4) 0.3794(3) 1.1281(3) 0.0219(7) Uani 1 d . . .
H103 H 0.5302 0.3643 1.2030 0.033 Uiso 1 calc . . GR
C101 C 0.7632(5) 0.3183(5) 0.9046(4) 0.0153(9) Uani 1 d . . .
C102 C 0.8719(5) 0.2448(5) 0.9658(4) 0.0177(10) Uani 1 d . . .
H102 H 0.8421 0.1703 1.0216 0.021 Uiso 1 calc . . R
C103 C 1.0242(5) 0.2813(5) 0.9447(4) 0.0177(10) Uani 1 d . . .
C104 C 1.0721(5) 0.3909(5) 0.8667(4) 0.0230(11) Uani 1 d . . .
H104 H 1.1772 0.4153 0.8542 0.028 Uiso 1 calc . . R
C105 C 0.9625(5) 0.4648(5) 0.8070(5) 0.0256(11) Uani 1 d . . .
H105 H 0.9926 0.5404 0.7524 0.031 Uiso 1 calc . . R
C106 C 0.8091(5) 0.4290(5) 0.8264(4) 0.0223(11) Uani 1 d . . .
H106 H 0.7351 0.4810 0.7857 0.027 Uiso 1 calc . . R
C107 C 0.5940(5) 0.2769(5) 0.9218(4) 0.0158(10) Uani 1 d . . .
H107 H 0.5356 0.3570 0.8911 0.019 Uiso 1 calc . . R
C108 C 0.5556(5) 0.2560(5) 1.0611(4) 0.0164(10) Uani 1 d . . .


_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
Br1 C3 1.905(4) . ?
O1 H1 0.8400 . ?
O1 C7 1.421(5) . ?
O2 C8 1.206(5) . ?
O3 H3 0.8400 . ?
O3 C8 1.324(5) . ?
C1 C2 1.389(6) . ?
C1 C6 1.387(6) . ?
C1 C7 1.529(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(6) . ?
C3 C4 1.384(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(6) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.523(6) . ?
Br11 C103 1.901(4) . ?
O101 H101 0.8400 . ?
O101 C107 1.423(5) . ?
O102 C108 1.212(5) . ?
O103 H103 0.8400 . ?
O103 C108 1.319(5) . ?
C101 C102 1.388(5) . ?
C101 C106 1.382(6) . ?
C101 C107 1.529(6) . ?
C102 H102 0.9500 . ?
C102 C103 1.384(6) . ?
C103 C104 1.378(6) . ?
C104 H104 0.9500 . ?
C104 C105 1.388(6) . ?
C105 H105 0.9500 . ?
C105 C106 1.389(6) . ?
C106 H106 0.9500 . ?
C107 H107 1.0000 . ?
C107 C108 1.516(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
C7 O1 H1 109.5 . . ?
C8 O3 H3 109.5 . . ?
C2 C1 C7 119.5(4) . . ?
C6 C1 C2 119.8(4) . . ?
C6 C1 C7 120.7(4) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 Br1 119.5(3) . . ?
C4 C3 Br1 118.7(3) . . ?
C4 C3 C2 121.8(4) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.8(4) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O1 C7 C1 110.4(3) . . ?
O1 C7 H7 108.5 . . ?
O1 C7 C8 109.4(3) . . ?
C1 C7 H7 108.5 . . ?
C8 C7 C1 111.4(4) . . ?
C8 C7 H7 108.5 . . ?
O2 C8 O3 125.2(4) . . ?
O2 C8 C7 122.8(4) . . ?
O3 C8 C7 112.0(4) . . ?
C107 O101 H101 109.5 . . ?
C108 O103 H103 109.5 . . ?
C102 C101 C107 120.6(4) . . ?
C106 C101 C102 119.4(4) . . ?
C106 C101 C107 119.9(4) . . ?
C101 C102 H102 120.4 . . ?
C103 C102 C101 119.3(4) . . ?
C103 C102 H102 120.4 . . ?
C102 C103 Br11 119.0(3) . . ?
C104 C103 Br11 118.8(3) . . ?
C104 C103 C102 122.1(4) . . ?
C103 C104 H104 120.9 . . ?
C103 C104 C105 118.1(4) . . ?
C105 C104 H104 120.9 . . ?
C104 C105 H105 119.7 . . ?
C104 C105 C106 120.6(4) . . ?
C106 C105 H105 119.7 . . ?
C101 C106 C105 120.5(4) . . ?
C101 C106 H106 119.8 . . ?
C105 C106 H106 119.8 . . ?
O101 C107 C101 110.7(3) . . ?
O101 C107 H107 108.2 . . ?
O101 C107 C108 109.8(3) . . ?
C101 C107 H107 108.2 . . ?
C108 C107 C101 111.5(3) . . ?
C108 C107 H107 108.2 . . ?
O102 C108 O103 124.6(4) . . ?
O102 C108 C107 123.3(4) . . ?
O103 C108 C107 112.1(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
Br1 C3 C4 C5 177.9(3) . . . . ?
O1 C7 C8 O2 -8.1(6) . . . . ?
O1 C7 C8 O3 171.8(3) . . . . ?
C1 C2 C3 Br1 -178.4(3) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C1 C7 C8 O2 114.1(5) . . . . ?
C1 C7 C8 O3 -66.0(5) . . . . ?
C2 C1 C6 C5 -0.4(7) . . . . ?
C2 C1 C7 O1 54.7(5) . . . . ?
C2 C1 C7 C8 -67.1(5) . . . . ?
C2 C3 C4 C5 -1.4(7) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 C1 -0.2(7) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
C6 C1 C7 O1 -123.6(4) . . . . ?
C6 C1 C7 C8 114.7(5) . . . . ?
C7 C1 C2 C3 -178.2(4) . . . . ?
C7 C1 C6 C5 177.8(4) . . . . ?
Br11 C103 C104 C105 -179.5(3) . . . . ?
O101 C107 C108 O102 17.1(5) . . . . ?
O101 C107 C108 O103 -163.9(3) . . . . ?
C101 C102 C103 Br11 -179.8(3) . . . . ?
C101 C102 C103 C104 1.5(7) . . . . ?
C101 C107 C108 O102 -106.0(5) . . . . ?
C101 C107 C108 O103 73.0(4) . . . . ?
C102 C101 C106 C105 1.3(7) . . . . ?
C102 C101 C107 O101 -76.8(5) . . . . ?
C102 C101 C107 C108 45.8(6) . . . . ?
C102 C103 C104 C105 -0.8(7) . . . . ?
C103 C104 C105 C106 0.4(7) . . . . ?
C104 C105 C106 C101 -0.6(7) . . . . ?
C106 C101 C102 C103 -1.7(7) . . . . ?
C106 C101 C107 O101 102.5(5) . . . . ?
C106 C101 C107 C108 -134.9(4) . . . . ?
C107 C101 C102 C103 177.7(4) . . . . ?
C107 C101 C106 C105 -178.1(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1007655'
#######################################################################
#
#                 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_2012tsb0001a-RS-3ClMA-3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7 Cl O3'
_chemical_formula_weight         186.59

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6521(15)
_cell_length_b                   8.9195(15)
_cell_length_c                   10.7309(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.900(6)
_cell_angle_gamma                90.00
_cell_volume                     828.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4047
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9916
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax'
_diffrn_source                   'Rotating Anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'

_diffrn_reflns_number            5526
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0845
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1895
_reflns_number_gt                1217
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0588P)²+0.0000P] where P=(Fo²+2Fc²)/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         1895
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7750(3) 0.3217(3) 0.8978(2) 0.0236(6) Uani 1 1 d . . .
C2 C 0.8939(3) 0.2399(3) 0.9535(3) 0.0262(6) Uani 1 1 d . . .
H2 H 0.8710 0.1554 1.0038 0.031 Uiso 1 1 calc R . .
C3 C 1.0455(4) 0.2819(3) 0.9356(3) 0.0314(7) Uani 1 1 d . . .
C4 C 1.0808(4) 0.4029(3) 0.8623(3) 0.0359(7) Uani 1 1 d . . .
H4 H 1.1856 0.4300 0.8495 0.043 Uiso 1 1 calc R . .
C5 C 0.9637(4) 0.4843(3) 0.8075(3) 0.0380(8) Uani 1 1 d . . .
H5 H 0.9879 0.5686 0.7573 0.046 Uiso 1 1 calc R . .
C6 C 0.8108(4) 0.4453(3) 0.8246(2) 0.0321(7) Uani 1 1 d . . .
H6 H 0.7305 0.5027 0.7864 0.039 Uiso 1 1 calc R . .
C7 C 0.6086(3) 0.2758(3) 0.9161(2) 0.0228(6) Uani 1 1 d . . .
H7 H 0.5392 0.3555 0.8813 0.027 Uiso 1 1 calc R . .
C8 C 0.5762(3) 0.2561(3) 1.0529(2) 0.0218(6) Uani 1 1 d . . .
Cl1 Cl 1.19307(9) 0.17999(9) 1.00650(9) 0.0473(3) Uani 1 1 d . . .
O1 O 0.5792(2) 0.13929(19) 0.85201(16) 0.0303(5) Uani 1 1 d . . .
H1 H 0.5431 0.0761 0.9017 0.045 Uiso 1 1 calc R . .
O2 O 0.5464(2) 0.13644(18) 1.09950(16) 0.0259(4) Uani 1 1 d . . .
O3 O 0.5858(2) 0.38384(18) 1.11360(16) 0.0279(5) Uani 1 1 d . . .
H3 H 0.5829 0.3674 1.1906 0.042 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.389(4) . ?
C1 C6 1.392(3) . ?
C1 C7 1.513(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(4) . ?
C3 Cl1 1.733(3) . ?
C4 C5 1.371(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.419(3) . ?
C7 C8 1.509(4) . ?
C7 H7 1.0000 . ?
C8 O2 1.208(3) . ?
C8 O3 1.314(3) . ?
O1 H1 0.8400 . ?
O3 H3 0.8400 . ?

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
C2 C1 C6 119.3(3) . . ?
C2 C1 C7 120.1(2) . . ?
C6 C1 C7 120.5(3) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 Cl1 119.7(2) . . ?
C2 C3 Cl1 119.5(2) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 C8 109.71(19) . . ?
O1 C7 C1 109.5(2) . . ?
C8 C7 C1 110.5(2) . . ?
O1 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C1 C7 H7 109.1 . . ?
O2 C8 O3 125.0(2) . . ?
O2 C8 C7 123.3(2) . . ?
O3 C8 C7 111.7(2) . . ?
C7 O1 H1 109.5 . . ?
C8 O3 H3 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
C6 C1 C2 C3 0.0(4) . . . . ?
C7 C1 C2 C3 179.5(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 Cl1 179.5(2) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
Cl1 C3 C4 C5 -179.2(2) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C7 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C7 O1 -69.7(3) . . . . ?
C6 C1 C7 O1 109.9(3) . . . . ?
C2 C1 C7 C8 51.2(3) . . . . ?
C6 C1 C7 C8 -129.2(2) . . . . ?
O1 C7 C8 O2 7.4(4) . . . . ?
C1 C7 C8 O2 -113.3(3) . . . . ?
O1 C7 C8 O3 -173.1(2) . . . . ?
C1 C7 C8 O3 66.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 2.05 2.742(2) 139.6 3_657
O1 H1 O2 0.84 2.19 2.675(2) 116.8 .
O3 H3 O1 0.84 1.73 2.568(2) 171.9 4_566

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 1007656'
#######################################################################
#
#                 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_ale_cs_6a-RS-3F3CMA-1
_audit_creation_date             2014-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2013-4
_chemical_name_common            '3-Trifluoromomandelic Acid'
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H7 F3 O3'
_chemical_formula_sum            'C9 H7 F3 O3 '
_chemical_formula_weight         220.15
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0086(5)
_cell_length_b                   9.6372(7)
_cell_length_c                   10.5702(7)
_cell_angle_alpha                86.602(5)
_cell_angle_beta                 88.612(5)
_cell_angle_gamma                85.623(4)
_cell_volume                     913.22(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10577
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11647
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.409
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
scan:
	Number of images: 100
	           Slice: -27.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 120.0000
	             XTD: 45.1541
	          2theta: -16.5814
scan:
	Number of images: 90
	           Slice: -68.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 0.0000
	             XTD: 45.1541
	          2theta: -16.5814
scan:
	Number of images: 90
	           Slice: -68.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -180.0000
	             XTD: 45.1541
	          2theta: -16.5814
scan:
	Number of images: 80
	           Slice: -20.0000 - 60.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -8.0000
	             Phi: -60.0000
	             XTD: 45.1541
	          2theta: -16.5814
scan:
	Number of images: 15
	           Slice: 0.0000 - 15.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -40.0000
	             Phi: -180.0000
	             XTD: 45.1541
	          2theta: -16.5814
scan:
	Number of images: 104
	           Slice: -31.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 30.0000
	             XTD: 45.1541
	          2theta: -16.5814
scan:
	Number of images: 71
	           Slice: -64.0000 - 7.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -90.0000
	             XTD: 45.1541
	          2theta: -16.5814
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.071223
_diffrn_orient_matrix_UB_12      -0.084960
_diffrn_orient_matrix_UB_13      0.010405
_diffrn_orient_matrix_UB_21      0.010690
_diffrn_orient_matrix_UB_22      -0.011331
_diffrn_orient_matrix_UB_23      -0.103071
_diffrn_orient_matrix_UB_31      0.073430
_diffrn_orient_matrix_UB_32      -0.056726
_diffrn_orient_matrix_UB_33      0.019375
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3299
_reflns_number_total             4126
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+1.2203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1326
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 F3A, F3B, F1A, F1B, F2A, F2B, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C107(H107), C7(H7)
4.b Aromatic/amide H refined with riding coordinates:
 C102(H102), C104(H104), C105(H105), C106(H106), C2(H2), C4(H4), C5(H5), C6(H6)
4.c Idealised tetrahedral OH refined as rotating group:
 O101(H101), O103(H103), O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F101 F 1.27178(18) 0.71400(19) 0.51312(19) 0.0465(5) Uani 1 1 d . . . . .
F102 F 1.12765(18) 0.90184(18) 0.5207(2) 0.0489(5) Uani 1 1 d . . . . .
F103 F 1.2241(2) 0.8070(2) 0.68972(18) 0.0485(5) Uani 1 1 d . . . . .
O101 O 0.58030(17) 0.85393(16) 0.64698(14) 0.0175(3) Uani 1 1 d . . . . .
H101 H 0.5503 0.9178 0.5941 0.026 Uiso 1 1 calc GR . . . .
O102 O 0.54119(19) 0.86852(17) 0.39554(15) 0.0220(4) Uani 1 1 d . . . . .
O103 O 0.58425(18) 0.63591(16) 0.38266(15) 0.0210(4) Uani 1 1 d . . . . .
H103 H 0.5568 0.6530 0.3076 0.031 Uiso 1 1 calc GR . . . .
C101 C 0.7668(2) 0.6658(2) 0.6062(2) 0.0155(4) Uani 1 1 d . . . . .
C102 C 0.8865(2) 0.7483(2) 0.5802(2) 0.0174(4) Uani 1 1 d . . . . .
H102 H 0.8694 0.8420 0.5474 0.021 Uiso 1 1 calc R . . . .
C103 C 1.0312(2) 0.6915(2) 0.6031(2) 0.0194(5) Uani 1 1 d . . . . .
C104 C 1.0581(3) 0.5530(2) 0.6487(2) 0.0220(5) Uani 1 1 d . . . . .
H104 H 1.1570 0.5151 0.6632 0.026 Uiso 1 1 calc R . . . .
C105 C 0.9393(3) 0.4712(2) 0.6725(2) 0.0231(5) Uani 1 1 d . . . . .
H105 H 0.9569 0.3766 0.7024 0.028 Uiso 1 1 calc R . . . .
C106 C 0.7937(3) 0.5279(2) 0.6526(2) 0.0193(5) Uani 1 1 d . . . . .
H106 H 0.7125 0.4721 0.6707 0.023 Uiso 1 1 calc R . . . .
C107 C 0.6076(2) 0.7263(2) 0.5846(2) 0.0154(4) Uani 1 1 d . . . . .
H107 H 0.5381 0.6580 0.6218 0.018 Uiso 1 1 calc R . . . .
C108 C 0.5744(2) 0.7529(2) 0.4432(2) 0.0168(4) Uani 1 1 d . . . . .
C109 C 1.1623(3) 0.7784(3) 0.5805(2) 0.0253(5) Uani 1 1 d . . . . .
F1A F -0.2002(16) 0.7665(11) -0.0843(13) 0.042(3) Uani 0.225(12) 1 d . . P A 2
F1B F -0.2480(4) 0.8001(4) -0.0220(6) 0.0559(14) Uani 0.775(12) 1 d . . P A 1
F2A F -0.2280(19) 0.666(2) 0.0942(16) 0.056(4) Uani 0.225(12) 1 d . . P A 2
F2B F -0.1859(5) 0.6156(4) 0.0910(4) 0.0412(9) Uani 0.775(12) 1 d . . P A 1
F3A F -0.0706(12) 0.5791(12) -0.0349(19) 0.051(4) Uani 0.225(12) 1 d . . P A 2
F3B F -0.0841(4) 0.6476(9) -0.0927(4) 0.076(2) Uani 0.775(12) 1 d . . P A 1
O1 O 0.45920(18) 0.64678(16) 0.15641(14) 0.0195(3) Uani 1 1 d . . . . .
H1 H 0.4688 0.5795 0.1091 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.48327(19) 0.63866(17) -0.09996(15) 0.0225(4) Uani 1 1 d . . . . .
O3 O 0.45108(19) 0.87320(16) -0.12423(15) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.4815 0.8601 -0.1986 0.031 Uiso 1 1 calc GR . . . .
C1 C 0.2508(2) 0.8137(2) 0.1014(2) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.1409(3) 0.7453(2) 0.0443(2) 0.0200(5) Uani 1 1 d . . . . .
H2 H 0.1685 0.6719 -0.0097 0.024 Uiso 1 1 calc R . . . .
C3 C -0.0093(3) 0.7848(3) 0.0667(2) 0.0222(5) Uani 1 1 d . . . . .
C4 C -0.0514(3) 0.8918(3) 0.1456(3) 0.0305(6) Uani 1 1 d . . . . .
H4 H -0.1538 0.9185 0.1602 0.037 Uiso 1 1 calc R . . . .
C5 C 0.0569(3) 0.9591(3) 0.2025(3) 0.0362(7) Uani 1 1 d . . . . .
H5 H 0.0288 1.0325 0.2564 0.043 Uiso 1 1 calc R . . . .
C6 C 0.2079(3) 0.9200(3) 0.1814(2) 0.0269(5) Uani 1 1 d . . . . .
H6 H 0.2816 0.9662 0.2219 0.032 Uiso 1 1 calc R . . . .
C7 C 0.4158(2) 0.7720(2) 0.0824(2) 0.0167(4) Uani 1 1 d . . . . .
H7 H 0.4736 0.8486 0.1111 0.020 Uiso 1 1 calc R . . . .
C8 C 0.4542(2) 0.7524(2) -0.0576(2) 0.0170(4) Uani 1 1 d . . . . .
C9 C -0.1284(3) 0.7082(3) 0.0098(3) 0.0313(6) Uani 1 1 d . . . . .


_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
F101 C109 1.338(3) . ?
F102 C109 1.332(3) . ?
F103 C109 1.346(3) . ?
O101 H101 0.8400 . ?
O101 C107 1.432(2) . ?
O102 C108 1.214(3) . ?
O103 H103 0.8400 . ?
O103 C108 1.326(3) . ?
C101 C102 1.401(3) . ?
C101 C106 1.394(3) . ?
C101 C107 1.523(3) . ?
C102 H102 0.9500 . ?
C102 C103 1.396(3) . ?
C103 C104 1.397(3) . ?
C103 C109 1.506(3) . ?
C104 H104 0.9500 . ?
C104 C105 1.386(3) . ?
C105 H105 0.9500 . ?
C105 C106 1.398(3) . ?
C106 H106 0.9500 . ?
C107 H107 1.0000 . ?
C107 C108 1.533(3) . ?
F1A C9 1.278(9) . ?
F1B C9 1.377(4) . ?
F2A C9 1.317(14) . ?
F2B C9 1.327(4) . ?
F3A C9 1.415(10) . ?
F3B C9 1.302(4) . ?
O1 H1 0.8400 . ?
O1 C7 1.433(3) . ?
O2 C8 1.216(3) . ?
O3 H3 0.8400 . ?
O3 C8 1.323(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.394(3) . ?
C1 C7 1.522(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 C4 1.390(4) . ?
C3 C9 1.503(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(4) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.531(3) . ?

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
C107 O101 H101 109.5 . . ?
C108 O103 H103 109.5 . . ?
C102 C101 C107 120.27(19) . . ?
C106 C101 C102 119.7(2) . . ?
C106 C101 C107 120.01(19) . . ?
C101 C102 H102 120.4 . . ?
C103 C102 C101 119.3(2) . . ?
C103 C102 H102 120.4 . . ?
C102 C103 C104 120.9(2) . . ?
C102 C103 C109 120.8(2) . . ?
C104 C103 C109 118.3(2) . . ?
C103 C104 H104 120.2 . . ?
C105 C104 C103 119.6(2) . . ?
C105 C104 H104 120.2 . . ?
C104 C105 H105 120.0 . . ?
C104 C105 C106 120.0(2) . . ?
C106 C105 H105 120.0 . . ?
C101 C106 C105 120.5(2) . . ?
C101 C106 H106 119.7 . . ?
C105 C106 H106 119.7 . . ?
O101 C107 C101 110.33(17) . . ?
O101 C107 H107 108.4 . . ?
O101 C107 C108 109.25(17) . . ?
C101 C107 H107 108.4 . . ?
C101 C107 C108 112.06(17) . . ?
C108 C107 H107 108.4 . . ?
O102 C108 O103 125.4(2) . . ?
O102 C108 C107 122.69(19) . . ?
O103 C108 C107 111.93(18) . . ?
F101 C109 F103 105.6(2) . . ?
F101 C109 C103 112.43(19) . . ?
F102 C109 F101 107.2(2) . . ?
F102 C109 F103 105.5(2) . . ?
F102 C109 C103 113.6(2) . . ?
F103 C109 C103 111.9(2) . . ?
C7 O1 H1 109.5 . . ?
C8 O3 H3 109.5 . . ?
C2 C1 C7 121.9(2) . . ?
C6 C1 C2 119.1(2) . . ?
C6 C1 C7 119.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C9 120.5(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 C9 118.9(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C1 111.03(17) . . ?
O1 C7 H7 108.3 . . ?
O1 C7 C8 109.76(17) . . ?
C1 C7 H7 108.3 . . ?
C1 C7 C8 111.08(18) . . ?
C8 C7 H7 108.3 . . ?
O2 C8 O3 125.4(2) . . ?
O2 C8 C7 123.1(2) . . ?
O3 C8 C7 111.53(18) . . ?
F1A C9 F2A 106.9(9) . . ?
F1A C9 F3A 103.7(7) . . ?
F1A C9 C3 118.9(5) . . ?
F1B C9 C3 109.8(3) . . ?
F2A C9 F3A 100.9(9) . . ?
F2A C9 C3 113.0(8) . . ?
F2B C9 F1B 103.9(3) . . ?
F2B C9 C3 113.0(3) . . ?
F3A C9 C3 111.7(5) . . ?
F3B C9 F1B 107.1(3) . . ?
F3B C9 F2B 109.2(4) . . ?
F3B C9 C3 113.2(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O101 H101 O102 0.84 2.17 2.826(2) 135.4 2_676
O103 H103 O1 0.84 1.85 2.661(2) 162.2 .
O1 H1 O2 0.84 2.12 2.855(2) 145.9 2_665
O3 H3 O101 0.84 1.84 2.669(2) 167.8 1_554

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
O101 C107 C108 O102 4.9(3) . . . . ?
O101 C107 C108 O103 -174.11(17) . . . . ?
C101 C102 C103 C104 1.4(3) . . . . ?
C101 C102 C103 C109 -177.9(2) . . . . ?
C101 C107 C108 O102 -117.7(2) . . . . ?
C101 C107 C108 O103 63.3(2) . . . . ?
C102 C101 C106 C105 -0.5(3) . . . . ?
C102 C101 C107 O101 -52.0(3) . . . . ?
C102 C101 C107 C108 70.0(2) . . . . ?
C102 C103 C104 C105 -0.5(3) . . . . ?
C102 C103 C109 F101 -131.5(2) . . . . ?
C102 C103 C109 F102 -9.5(3) . . . . ?
C102 C103 C109 F103 109.8(3) . . . . ?
C103 C104 C105 C106 -0.9(3) . . . . ?
C104 C103 C109 F101 49.1(3) . . . . ?
C104 C103 C109 F102 171.1(2) . . . . ?
C104 C103 C109 F103 -69.6(3) . . . . ?
C104 C105 C106 C101 1.4(3) . . . . ?
C106 C101 C102 C103 -0.9(3) . . . . ?
C106 C101 C107 O101 127.7(2) . . . . ?
C106 C101 C107 C108 -110.4(2) . . . . ?
C107 C101 C102 C103 178.76(19) . . . . ?
C107 C101 C106 C105 179.9(2) . . . . ?
C109 C103 C104 C105 178.9(2) . . . . ?
O1 C7 C8 O2 15.9(3) . . . . ?
O1 C7 C8 O3 -164.24(17) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C9 -177.6(2) . . . . ?
C1 C7 C8 O2 -107.3(2) . . . . ?
C1 C7 C8 O3 72.6(2) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C2 C1 C7 O1 -76.3(3) . . . . ?
C2 C1 C7 C8 46.2(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C2 C3 C9 F1A -105.3(10) . . . . ?
C2 C3 C9 F1B -144.7(3) . . . . ?
C2 C3 C9 F2A 128.3(11) . . . . ?
C2 C3 C9 F2B 99.8(4) . . . . ?
C2 C3 C9 F3A 15.4(10) . . . . ?
C2 C3 C9 F3B -25.1(5) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C3 C9 F1A 77.1(10) . . . . ?
C4 C3 C9 F1B 37.7(4) . . . . ?
C4 C3 C9 F2A -49.3(11) . . . . ?
C4 C3 C9 F2B -77.8(4) . . . . ?
C4 C3 C9 F3A -162.2(9) . . . . ?
C4 C3 C9 F3B 157.3(5) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C1 C7 O1 101.5(2) . . . . ?
C6 C1 C7 C8 -136.1(2) . . . . ?
C7 C1 C2 C3 178.5(2) . . . . ?
C7 C1 C6 C5 -178.9(2) . . . . ?
C9 C3 C4 C5 177.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_database_code_depnum_ccdc_archive 'CCDC 1007657'
#######################################################################
#
#                 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_2012jms0016aa-RS-3FMA-1
_audit_creation_date             2014-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H7 F O3'
_chemical_formula_sum            'C8 H7 F O3'
_chemical_formula_weight         170.14
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1424(6)
_cell_length_b                   10.2396(7)
_cell_length_c                   9.3604(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.016(8)
_cell_angle_gamma                90
_cell_volume                     780.30(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4601
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.069
_diffrn_reflns_theta_min         2.502
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
scan:
	Number of images: 123
	           Slice: -110.0000 - 13.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -45.0000
	             Phi: 240.0000
	             XTD: 45.0000
	          2theta: -20.0000
scan:
	Number of images: 120
	           Slice: -110.0000 - 10.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 45.0000
	          2theta: -20.0000
scan:
	Number of images: 79
	           Slice: -110.0000 - -31.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 45.0000
	          2theta: -20.0000
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.001155
_diffrn_orient_matrix_UB_12      -0.001220
_diffrn_orient_matrix_UB_13      -0.122731
_diffrn_orient_matrix_UB_21      0.032940
_diffrn_orient_matrix_UB_22      -0.091840
_diffrn_orient_matrix_UB_23      0.000603
_diffrn_orient_matrix_UB_31      -0.100487
_diffrn_orient_matrix_UB_32      -0.036045
_diffrn_orient_matrix_UB_33      -0.000588
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                699
_reflns_number_total             1372
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1372
_refine_ls_number_restraints     359
_refine_ls_R_factor_all          0.1836
_refine_ls_R_factor_gt           0.1026
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1310P)²+1.6154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2744
_refine_ls_wR_factor_ref         0.3223
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 F1B-C3B
 1.35 with sigma of 0.02
3. Restrained planarity
 C1, C2B, C6B, C4, C3B, C5B, F1B
 with sigma of 0.1
4. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
6. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(C2B)=Sof(H2B)=Sof(C6B)=Sof(H6B)=Sof(H4B)=Sof(C3B)=Sof(C5B)=Sof(H5B)=
 Sof(F1B)=1-FVAR(1)
 Sof(H4A)=Sof(F1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=
 Sof(H6A)=FVAR(1)
8.a Ternary CH refined with riding coordinates:
 C7(H7)
8.b Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C6B(H6B), C4(H4B), C4(H4A), C5B(H5B), C2A(H2A), C5A(H5A), C6A(H6A)
8.c Fitted hexagon refined as free rotating group:
 C1(C2B,C6B,C4,C3B,C5B)
8.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0747(6) 0.3448(4) 0.1395(5) 0.0578(14) Uani 1 1 d . U . . .
H1 H 0.0818 0.3941 0.0708 0.087 Uiso 1 1 calc GR . . . .
O2 O 0.0309(6) 0.6036(5) 0.1382(5) 0.0630(15) Uani 1 1 d . U . . .
O3 O 0.0624(7) 0.6144(5) 0.3742(5) 0.0656(15) Uani 1 1 d . U . . .
H3 H 0.0009 0.6776 0.3691 0.098 Uiso 1 1 calc GR . . . .
C1 C 0.2991(7) 0.4026(7) 0.2973(7) 0.0512(15) Uani 1 1 d . U . . .
C2B C 0.4107(10) 0.485(3) 0.231(3) 0.072(8) Uani 0.135(10) 1 d G U P A 2
H2B H 0.3735 0.5482 0.1676 0.086 Uiso 0.135(10) 1 calc R . P A 2
C6B C 0.5778(9) 0.472(3) 0.261(3) 0.086(8) Uani 0.135(10) 1 d G U P A 2
H6B H 0.6524 0.5270 0.2170 0.103 Uiso 0.135(10) 1 calc R . P A 2
C4 C 0.6333(7) 0.3772(9) 0.3565(10) 0.088(2) Uani 1 1 d G U . A .
H4B H 0.7452 0.3686 0.3764 0.106 Uiso 0.135(10) 1 calc R . P A 2
H4A H 0.7454 0.3678 0.3745 0.106 Uiso 0.865(10) 1 calc R . P A 1
C3B C 0.5218(11) 0.295(2) 0.422(3) 0.087(8) Uani 0.135(10) 1 d DG U P A 2
C5B C 0.3547(10) 0.308(2) 0.393(3) 0.069(8) Uani 0.135(10) 1 d G U P A 2
H5B H 0.2800 0.2528 0.4368 0.083 Uiso 0.135(10) 1 calc R . P A 2
C7 C 0.1189(8) 0.4132(6) 0.2665(6) 0.0465(15) Uani 1 1 d . U . . .
H7 H 0.0596 0.3745 0.3463 0.056 Uiso 1 1 calc R . . . .
C8 C 0.0664(8) 0.5566(6) 0.2510(7) 0.0472(15) Uani 1 1 d . U . . .
F1A F 0.6887(8) 0.4892(11) 0.1516(9) 0.155(4) Uani 0.865(10) 1 d . U P A 1
C2A C 0.4142(11) 0.4555(12) 0.2068(11) 0.076(3) Uani 0.865(10) 1 d . U P A 1
H2A H 0.3811 0.5019 0.1258 0.091 Uiso 0.865(10) 1 calc R . P A 1
C3A C 0.5795(13) 0.4383(13) 0.2390(13) 0.089(3) Uani 0.865(10) 1 d . U P A 1
C5A C 0.5261(13) 0.3300(12) 0.4473(14) 0.092(3) Uani 0.865(10) 1 d . U P A 1
H5A H 0.5639 0.2897 0.5307 0.110 Uiso 0.865(10) 1 calc R . P A 1
C6A C 0.3549(11) 0.3393(9) 0.4204(11) 0.068(3) Uani 0.865(10) 1 d . U P A 1
H6A H 0.2808 0.3037 0.4841 0.082 Uiso 0.865(10) 1 calc R . P A 1
F1B F 0.617(4) 0.228(4) 0.506(4) 0.107(12) Uani 0.135(10) 1 d D U P A 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
O1 C7 1.419(7) . ?
O2 C8 1.191(7) . ?
O3 C8 1.297(8) . ?
C1 C2B 1.3900 . ?
C1 C5B 1.3900 . ?
C1 C7 1.495(8) . ?
C1 C2A 1.385(11) . ?
C1 C6A 1.391(11) . ?
C2B C6B 1.3900 . ?
C6B C4 1.3900 . ?
C4 C3B 1.3900 . ?
C4 C3A 1.333(14) . ?
C4 C5A 1.321(14) . ?
C3B C5B 1.3900 . ?
C3B F1B 1.291(18) . ?
C7 C8 1.536(9) . ?
F1A C3A 1.325(12) . ?
C2A C3A 1.386(13) . ?
C5A C6A 1.415(13) . ?

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
C2B C1 C5B 120.0 . . ?
C2B C1 C7 121.2(5) . . ?
C5B C1 C7 118.8(5) . . ?
C2A C1 C7 121.8(7) . . ?
C2A C1 C6A 118.3(7) . . ?
C6A C1 C7 119.9(7) . . ?
C1 C2B C6B 120.0 . . ?
C4 C6B C2B 120.0 . . ?
C6B C4 C3B 120.0 . . ?
C5A C4 C3A 119.4(8) . . ?
C5B C3B C4 120.0 . . ?
F1B C3B C4 101.6(19) . . ?
F1B C3B C5B 138.2(19) . . ?
C3B C5B C1 120.0 . . ?
O1 C7 C1 111.1(6) . . ?
O1 C7 C8 109.0(5) . . ?
C1 C7 C8 111.0(5) . . ?
O2 C8 O3 126.5(6) . . ?
O2 C8 C7 122.2(6) . . ?
O3 C8 C7 111.3(5) . . ?
C1 C2A C3A 118.8(9) . . ?
C4 C3A C2A 122.9(10) . . ?
F1A C3A C4 118.7(9) . . ?
F1A C3A C2A 118.4(10) . . ?
C4 C5A C6A 121.4(10) . . ?
C1 C6A C5A 119.0(9) . . ?

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
C2A_a C1 C2B_b C6B_b -82.5(19) . . . . ?
O1 C7 C8 O2 -15.6(9) . . . . ?
O1 C7 C8 O3 162.6(6) . . . . ?
C1 C2B C6B C4 0.0 . . . . ?
C1 C7 C8 O2 107.0(7) . . . . ?
C1 C7 C8 O3 -74.7(7) . . . . ?
C1 C2A C3A C4 -2.7(18) . . . . ?
C1 C2A C3A F1A 180.0(11) . . . . ?
C2B C1 C5B C3B 0.0 . . . . ?
C2B C1 C7 O1 82.7(19) . . . . ?
C2B C1 C7 C8 -39(2) . . . . ?
C2B C1 C2A C3A 89(2) . . . . ?
C2B C1 C6A C5A -18(2) . . . . ?
C2B C6B C4 C3B 0.0 . . . . ?
C2B C6B C4 C3A 81.7(18) . . . . ?
C2B C6B C4 C5A -20.2(19) . . . . ?
C6B C4 C3B C5B 0.0 . . . . ?
C6B C4 C3B F1B -177(3) . . . . ?
C6B C4 C3A F1A 90(2) . . . . ?
C6B C4 C3A C2A -87(2) . . . . ?
C6B C4 C5A C6A 21(2) . . . . ?
C4 C3B C5B C1 0.0 . . . . ?
C4 C5A C6A C1 -1.6(17) . . . . ?
C3B C4 C3A F1A -162.4(18) . . . . ?
C3B C4 C3A C2A 20(2) . . . . ?
C3B C4 C5A C6A -82.6(19) . . . . ?
C5B C1 C2B C6B 0.0 . . . . ?
C5B C1 C7 O1 -96.7(19) . . . . ?
C5B C1 C7 C8 141.8(18) . . . . ?
C5B C1 C2A C3A -16(2) . . . . ?
C5B C1 C6A C5A 89(2) . . . . ?
C7 C1 C2B C6B -179.4(6) . . . . ?
C7 C1 C5B C3B 179.4(6) . . . . ?
C7 C1 C2A C3A -177.7(9) . . . . ?
C7 C1 C6A C5A 179.8(8) . . . . ?
C2A C1 C5B C3B 17.5(19) . . . . ?
C2A C1 C7 O1 64.3(10) . . . . ?
C2A C1 C7 C8 -57.2(10) . . . . ?
C2A C1 C6A C5A -0.8(14) . . . . ?
C3A C4 C3B C5B -19(2) . . . . ?
C3A C4 C3B F1B 164.5(19) . . . . ?
C3A C4 C5A C6A 1.9(18) . . . . ?
C5A C4 C3B C5B 86.2(18) . . . . ?
C5A C4 C3B F1B -91(3) . . . . ?
C5A C4 C3A F1A 177.6(12) . . . . ?
C5A C4 C3A C2A 0.2(19) . . . . ?
C6A C1 C2B C6B 19.0(19) . . . . ?
C6A C1 C5B C3B -82.1(18) . . . . ?
C6A C1 C7 O1 -116.3(8) . . . . ?
C6A C1 C7 C8 122.2(8) . . . . ?
C6A C1 C2A C3A 2.9(15) . . . . ?
F1B C3B C5B C1 175(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1007658'
#######################################################################
#
#                 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_2012jms0011aa-RS-3IMA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 I O3'
_chemical_formula_sum            'C8 H7 I O3'
_chemical_formula_weight         278.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8488(4)
_cell_length_b                   14.1055(10)
_cell_length_c                   15.0534(10)
_cell_angle_alpha                104.634(7)
_cell_angle_beta                 94.543(7)
_cell_angle_gamma                90.699(6)
_cell_volume                     1401.86(16)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14085
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    3.391
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7731
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16687
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4945
_reflns_number_gt                3279
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0343P)²+4.1426P] where P=(Fo²+2Fc²)/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         4945
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
I3 I 0.37330(11) 0.02935(5) 0.26702(5) 0.1078(3) Uani 1 1 d . . .
I2 I 0.94103(9) 0.60078(5) 0.38306(4) 0.0846(2) Uani 1 1 d . . .
I1 I 0.36839(11) 0.79113(5) 0.46970(4) 0.0985(3) Uani 1 1 d . . .
O1 O 0.9807(7) 0.7113(3) 0.1229(3) 0.0598(13) Uani 1 1 d . . .
H1 H 1.0541 0.6632 0.1117 0.090 Uiso 1 1 calc R . .
O3 O 0.4648(6) 0.7272(3) 0.0975(3) 0.0540(12) Uani 1 1 d . . .
H3 H 0.4441 0.6741 0.1113 0.081 Uiso 1 1 calc R . .
O23 O -0.2617(8) 0.2812(3) 0.0712(3) 0.0601(13) Uani 1 1 d . . .
H23 H -0.3144 0.2793 0.0184 0.090 Uiso 1 1 calc R . .
O12 O 0.0201(7) 0.4486(4) 0.1016(4) 0.0728(15) Uani 1 1 d . . .
H11 H -0.0595 0.4927 0.0984 0.109 Uiso 1 1 calc R . .
O22 O -0.4992(7) 0.1227(3) 0.0333(3) 0.0571(12) Uani 1 1 d . . .
O2 O 0.7425(7) 0.5959(3) 0.0933(3) 0.0525(11) Uani 1 1 d . . .
O13 O 0.2843(7) 0.3181(3) 0.0854(3) 0.0537(12) Uani 1 1 d . . .
H13 H 0.3759 0.2786 0.0808 0.081 Uiso 1 1 calc R . .
O11 O 0.2399(6) 0.5728(3) 0.1226(3) 0.0536(12) Uani 1 1 d . . .
O21 O -0.2488(7) 0.0229(3) 0.0241(4) 0.0691(15) Uani 1 1 d . . .
H21 H -0.3392 -0.0201 0.0155 0.104 Uiso 1 1 calc R . .
C22 C 0.0673(10) 0.1295(5) 0.1728(5) 0.0527(17) Uani 1 1 d . . .
H24 H 0.1146 0.0885 0.1192 0.063 Uiso 1 1 calc R . .
C13 C 0.6899(10) 0.5077(5) 0.3400(5) 0.0511(17) Uani 1 1 d . . .
C1 C 0.6717(9) 0.8127(5) 0.2348(5) 0.0473(17) Uani 1 1 d . . .
C24 C 0.0863(11) 0.1863(6) 0.3379(5) 0.061(2) Uani 1 1 d . . .
H25 H 0.1435 0.1842 0.3970 0.074 Uiso 1 1 calc R . .
C7 C 0.6557(9) 0.7638(5) 0.1321(5) 0.0474(16) Uani 1 1 d . . .
H2 H 0.6938 0.8134 0.0989 0.057 Uiso 1 1 calc R . .
C23 C 0.1486(10) 0.1268(5) 0.2597(5) 0.0531(18) Uani 1 1 d . . .
C27 C -0.1733(10) 0.1916(5) 0.0701(4) 0.0479(16) Uani 1 1 d . . .
H22 H -0.0694 0.1809 0.0258 0.058 Uiso 1 1 calc R . .
C12 C 0.6068(9) 0.4953(5) 0.2519(4) 0.0458(16) Uani 1 1 d . . .
H14 H 0.6597 0.5297 0.2121 0.055 Uiso 1 1 calc R . .
C4 C 0.7038(12) 0.9008(6) 0.4224(6) 0.068(2) Uani 1 1 d . . .
H5 H 0.7139 0.9308 0.4867 0.081 Uiso 1 1 calc R . .
C2 C 0.5456(10) 0.7858(5) 0.2913(5) 0.0486(17) Uani 1 1 d . . .
H4 H 0.4462 0.7365 0.2665 0.058 Uiso 1 1 calc R . .
C11 C 0.4460(9) 0.4328(5) 0.2215(4) 0.0407(15) Uani 1 1 d . . .
C3 C 0.5642(11) 0.8301(5) 0.3833(5) 0.0550(18) Uani 1 1 d . . .
C15 C 0.4535(12) 0.3983(6) 0.3683(5) 0.066(2) Uani 1 1 d . . .
H16 H 0.3986 0.3651 0.4085 0.079 Uiso 1 1 calc R . .
C17 C 0.3621(9) 0.4155(4) 0.1222(4) 0.0432(15) Uani 1 1 d . . .
H12 H 0.4689 0.4273 0.0842 0.052 Uiso 1 1 calc R . .
C6 C 0.8150(11) 0.8831(6) 0.2729(5) 0.063(2) Uani 1 1 d . . .
H7 H 0.9048 0.9015 0.2348 0.075 Uiso 1 1 calc R . .
C18 C 0.1993(9) 0.4862(5) 0.1147(4) 0.0434(15) Uani 1 1 d . . .
C21 C -0.0823(9) 0.1922(4) 0.1650(4) 0.0418(15) Uani 1 1 d . . .
C8 C 0.7999(10) 0.6802(5) 0.1129(4) 0.0464(16) Uani 1 1 d . . .
C14 C 0.6152(11) 0.4588(5) 0.3991(5) 0.0567(19) Uani 1 1 d . . .
H15 H 0.6749 0.4670 0.4598 0.068 Uiso 1 1 calc R . .
C28 C -0.3236(10) 0.1095(5) 0.0406(4) 0.0465(16) Uani 1 1 d . . .
C26 C -0.1476(10) 0.2518(5) 0.2434(5) 0.0533(17) Uani 1 1 d . . .
H27 H -0.2517 0.2947 0.2391 0.064 Uiso 1 1 calc R . .
C16 C 0.3686(11) 0.3846(5) 0.2791(5) 0.0566(18) Uani 1 1 d . . .
H17 H 0.2568 0.3419 0.2583 0.068 Uiso 1 1 calc R . .
C25 C -0.0601(11) 0.2487(6) 0.3291(5) 0.062(2) Uani 1 1 d . . .
H26 H -0.1036 0.2912 0.3830 0.075 Uiso 1 1 calc R . .
C5 C 0.8300(12) 0.9272(6) 0.3656(6) 0.079(3) Uani 1 1 d . . .
H6 H 0.9289 0.9766 0.3909 0.095 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
I3 C23 2.090(6) . ?
I2 C13 2.107(7) . ?
I1 C3 2.100(7) . ?
O1 C8 1.293(8) . ?
O1 H1 0.8400 . ?
O3 C7 1.410(7) . ?
O3 H3 0.8400 . ?
O23 C27 1.404(7) . ?
O23 H23 0.8400 . ?
O12 C18 1.311(8) . ?
O12 H11 0.8400 . ?
O22 C28 1.220(7) . ?
O2 C8 1.203(8) . ?
O13 C17 1.424(7) . ?
O13 H13 0.8400 . ?
O11 C18 1.225(7) . ?
O21 C28 1.303(7) . ?
O21 H21 0.8400 . ?
C22 C21 1.379(8) . ?
C22 C23 1.391(9) . ?
C22 H24 0.9500 . ?
C13 C12 1.369(9) . ?
C13 C14 1.379(10) . ?
C1 C6 1.370(10) . ?
C1 C2 1.374(9) . ?
C1 C7 1.520(9) . ?
C24 C25 1.363(10) . ?
C24 C23 1.364(10) . ?
C24 H25 0.9500 . ?
C7 C8 1.533(9) . ?
C7 H2 1.0000 . ?
C27 C28 1.496(9) . ?
C27 C21 1.510(8) . ?
C27 H22 1.0000 . ?
C12 C11 1.376(9) . ?
C12 H14 0.9500 . ?
C4 C3 1.358(10) . ?
C4 C5 1.374(11) . ?
C4 H5 0.9500 . ?
C2 C3 1.363(9) . ?
C2 H4 0.9500 . ?
C11 C16 1.362(9) . ?
C11 C17 1.518(8) . ?
C15 C14 1.366(11) . ?
C15 C16 1.385(10) . ?
C15 H16 0.9500 . ?
C17 C18 1.521(8) . ?
C17 H12 1.0000 . ?
C6 C5 1.372(11) . ?
C6 H7 0.9500 . ?
C21 C26 1.375(9) . ?
C14 H15 0.9500 . ?
C26 C25 1.390(9) . ?
C26 H27 0.9500 . ?
C16 H17 0.9500 . ?
C25 H26 0.9500 . ?
C5 H6 0.9500 . ?

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
C8 O1 H1 109.5 . . ?
C7 O3 H3 109.5 . . ?
C27 O23 H23 109.5 . . ?
C18 O12 H11 109.5 . . ?
C17 O13 H13 109.5 . . ?
C28 O21 H21 109.5 . . ?
C21 C22 C23 119.6(6) . . ?
C21 C22 H24 120.2 . . ?
C23 C22 H24 120.2 . . ?
C12 C13 C14 121.3(7) . . ?
C12 C13 I2 118.5(5) . . ?
C14 C13 I2 120.2(5) . . ?
C6 C1 C2 118.8(7) . . ?
C6 C1 C7 120.5(7) . . ?
C2 C1 C7 120.7(6) . . ?
C25 C24 C23 118.3(6) . . ?
C25 C24 H25 120.9 . . ?
C23 C24 H25 120.9 . . ?
O3 C7 C1 113.0(6) . . ?
O3 C7 C8 109.6(5) . . ?
C1 C7 C8 109.2(5) . . ?
O3 C7 H2 108.3 . . ?
C1 C7 H2 108.3 . . ?
C8 C7 H2 108.3 . . ?
C24 C23 C22 121.5(6) . . ?
C24 C23 I3 120.8(5) . . ?
C22 C23 I3 117.8(5) . . ?
O23 C27 C28 109.9(5) . . ?
O23 C27 C21 110.4(5) . . ?
C28 C27 C21 108.6(5) . . ?
O23 C27 H22 109.3 . . ?
C28 C27 H22 109.3 . . ?
C21 C27 H22 109.3 . . ?
C13 C12 C11 119.5(6) . . ?
C13 C12 H14 120.3 . . ?
C11 C12 H14 120.3 . . ?
C3 C4 C5 117.6(8) . . ?
C3 C4 H5 121.2 . . ?
C5 C4 H5 121.2 . . ?
C3 C2 C1 119.5(6) . . ?
C3 C2 H4 120.2 . . ?
C1 C2 H4 120.2 . . ?
C16 C11 C12 120.2(6) . . ?
C16 C11 C17 120.8(6) . . ?
C12 C11 C17 118.9(6) . . ?
C4 C3 C2 122.7(7) . . ?
C4 C3 I1 117.6(6) . . ?
C2 C3 I1 119.7(5) . . ?
C14 C15 C16 120.9(7) . . ?
C14 C15 H16 119.6 . . ?
C16 C15 H16 119.6 . . ?
O13 C17 C11 112.2(5) . . ?
O13 C17 C18 108.2(5) . . ?
C11 C17 C18 110.3(5) . . ?
O13 C17 H12 108.7 . . ?
C11 C17 H12 108.7 . . ?
C18 C17 H12 108.7 . . ?
C1 C6 C5 120.6(7) . . ?
C1 C6 H7 119.7 . . ?
C5 C6 H7 119.7 . . ?
O11 C18 O12 124.1(6) . . ?
O11 C18 C17 119.8(6) . . ?
O12 C18 C17 116.1(6) . . ?
C26 C21 C22 119.4(6) . . ?
C26 C21 C27 121.8(6) . . ?
C22 C21 C27 118.8(6) . . ?
O2 C8 O1 126.3(7) . . ?
O2 C8 C7 120.9(6) . . ?
O1 C8 C7 112.8(6) . . ?
C15 C14 C13 118.5(6) . . ?
C15 C14 H15 120.8 . . ?
C13 C14 H15 120.8 . . ?
O22 C28 O21 123.5(6) . . ?
O22 C28 C27 123.0(6) . . ?
O21 C28 C27 113.5(6) . . ?
C21 C26 C25 119.5(7) . . ?
C21 C26 H27 120.3 . . ?
C25 C26 H27 120.3 . . ?
C11 C16 C15 119.7(7) . . ?
C11 C16 H17 120.2 . . ?
C15 C16 H17 120.2 . . ?
C24 C25 C26 121.7(7) . . ?
C24 C25 H26 119.1 . . ?
C26 C25 H26 119.1 . . ?
C6 C5 C4 120.8(8) . . ?
C6 C5 H6 119.6 . . ?
C4 C5 H6 119.6 . . ?

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
C6 C1 C7 O3 -154.7(6) . . . . ?
C2 C1 C7 O3 26.8(8) . . . . ?
C6 C1 C7 C8 83.1(7) . . . . ?
C2 C1 C7 C8 -95.5(7) . . . . ?
C25 C24 C23 C22 0.5(11) . . . . ?
C25 C24 C23 I3 179.7(6) . . . . ?
C21 C22 C23 C24 -1.3(11) . . . . ?
C21 C22 C23 I3 179.5(5) . . . . ?
C14 C13 C12 C11 -0.2(10) . . . . ?
I2 C13 C12 C11 178.2(5) . . . . ?
C6 C1 C2 C3 0.8(10) . . . . ?
C7 C1 C2 C3 179.4(6) . . . . ?
C13 C12 C11 C16 0.9(9) . . . . ?
C13 C12 C11 C17 -176.7(6) . . . . ?
C5 C4 C3 C2 -0.1(12) . . . . ?
C5 C4 C3 I1 -179.1(6) . . . . ?
C1 C2 C3 C4 -0.1(11) . . . . ?
C1 C2 C3 I1 178.8(5) . . . . ?
C16 C11 C17 O13 -31.4(8) . . . . ?
C12 C11 C17 O13 146.2(6) . . . . ?
C16 C11 C17 C18 89.4(7) . . . . ?
C12 C11 C17 C18 -93.0(7) . . . . ?
C2 C1 C6 C5 -1.2(11) . . . . ?
C7 C1 C6 C5 -179.8(7) . . . . ?
O13 C17 C18 O11 -163.7(6) . . . . ?
C11 C17 C18 O11 73.2(8) . . . . ?
O13 C17 C18 O12 17.5(8) . . . . ?
C11 C17 C18 O12 -105.6(6) . . . . ?
C23 C22 C21 C26 0.6(10) . . . . ?
C23 C22 C21 C27 -177.9(6) . . . . ?
O23 C27 C21 C26 24.7(9) . . . . ?
C28 C27 C21 C26 -95.8(7) . . . . ?
O23 C27 C21 C22 -156.8(6) . . . . ?
C28 C27 C21 C22 82.7(7) . . . . ?
O3 C7 C8 O2 -17.1(8) . . . . ?
C1 C7 C8 O2 107.2(7) . . . . ?
O3 C7 C8 O1 164.8(5) . . . . ?
C1 C7 C8 O1 -70.9(7) . . . . ?
C16 C15 C14 C13 1.3(11) . . . . ?
C12 C13 C14 C15 -0.9(11) . . . . ?
I2 C13 C14 C15 -179.3(5) . . . . ?
O23 C27 C28 O22 -10.4(9) . . . . ?
C21 C27 C28 O22 110.5(7) . . . . ?
O23 C27 C28 O21 170.0(6) . . . . ?
C21 C27 C28 O21 -69.1(7) . . . . ?
C22 C21 C26 C25 0.8(10) . . . . ?
C27 C21 C26 C25 179.3(6) . . . . ?
C12 C11 C16 C15 -0.6(10) . . . . ?
C17 C11 C16 C15 177.0(6) . . . . ?
C14 C15 C16 C11 -0.6(11) . . . . ?
C23 C24 C25 C26 0.9(12) . . . . ?
C21 C26 C25 C24 -1.6(11) . . . . ?
C1 C6 C5 C4 1.0(13) . . . . ?
C3 C4 C5 C6 -0.3(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 1007659'
#######################################################################
#
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#                                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
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# 
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#  data retrieval see:
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#  to carry out CIF format checking respectively.
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data_ale_cs_8ba
_audit_creation_date             2014-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        '3-methylmandelic acid'
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_weight         166.17
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5713(5)
_cell_length_b                   9.3327(7)
_cell_length_c                   10.5393(7)
_cell_angle_alpha                92.391(6)
_cell_angle_beta                 94.241(6)
_cell_angle_gamma                90.556(6)
_cell_volume                     839.96(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'Seeded with 3-chloromandelic acid'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10784
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.859
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.007239
_diffrn_orient_matrix_UB_12      0.001970
_diffrn_orient_matrix_UB_13      0.116758
_diffrn_orient_matrix_UB_21      -0.003630
_diffrn_orient_matrix_UB_22      0.107191
_diffrn_orient_matrix_UB_23      -0.000205
_diffrn_orient_matrix_UB_31      -0.094343
_diffrn_orient_matrix_UB_32      0.000885
_diffrn_orient_matrix_UB_33      0.012936
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2773
_reflns_number_total             3847
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.4430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1321
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C107(H107)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C102(H102), C104(H104), C105(H105), C106(H106)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C109(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O101(H101), O103(H103)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49151(17) 0.35632(14) 0.64866(12) 0.0253(3) Uani 1 1 d . . . . .
H1 H 0.4724 0.4333 0.6124 0.038 Uiso 1 1 calc GR . . . .
O2 O 0.53693(18) 0.35754(14) 0.39504(13) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.48719(18) 0.12204(14) 0.37545(13) 0.0264(3) Uani 1 1 d . . . . .
H3 H 0.5285 0.1299 0.3062 0.040 Uiso 1 1 calc GR . . . .
C1 C 0.2520(2) 0.2315(2) 0.55960(18) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.1748(2) 0.1379(2) 0.63471(18) 0.0227(4) Uani 1 1 d . . . . .
H2 H 0.2346 0.0784 0.6903 0.027 Uiso 1 1 calc R . . . .
C3 C 0.0120(2) 0.1300(2) 0.62987(19) 0.0256(4) Uani 1 1 d . . . . .
C4 C -0.0732(2) 0.2171(2) 0.5466(2) 0.0298(5) Uani 1 1 d . . . . .
H4 H -0.1843 0.2119 0.5409 0.036 Uiso 1 1 calc R . . . .
C5 C 0.0014(3) 0.3111(2) 0.4720(2) 0.0339(5) Uani 1 1 d . . . . .
H5 H -0.0586 0.3702 0.4161 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1636(3) 0.3193(2) 0.4787(2) 0.0288(5) Uani 1 1 d . . . . .
H6 H 0.2145 0.3847 0.4281 0.035 Uiso 1 1 calc R . . . .
C7 C 0.4297(2) 0.23855(19) 0.56937(17) 0.0213(4) Uani 1 1 d . . . . .
H7 H 0.4692 0.1481 0.6073 0.026 Uiso 1 1 calc R . . . .
C8 C 0.4908(2) 0.24687(19) 0.43760(18) 0.0214(4) Uani 1 1 d . . . . .
C9 C -0.0703(3) 0.0309(2) 0.7129(2) 0.0350(5) Uani 1 1 d . . . . .
H9A H 0.0027 -0.0420 0.7442 0.053 Uiso 1 1 calc GR . . . .
H9B H -0.1592 -0.0159 0.6633 0.053 Uiso 1 1 calc GR . . . .
H9C H -0.1081 0.0862 0.7854 0.053 Uiso 1 1 calc GR . . . .
O101 O 0.60718(15) 0.13571(13) 0.15421(12) 0.0202(3) Uani 1 1 d . . . . .
H101 H 0.5652 0.0736 0.1023 0.030 Uiso 1 1 calc GR . . . .
O102 O 0.54136(16) 0.12829(14) -0.09839(12) 0.0226(3) Uani 1 1 d . . . . .
O103 O 0.56837(16) 0.36734(14) -0.10806(13) 0.0233(3) Uani 1 1 d . . . . .
H103 H 0.5403 0.3509 -0.1854 0.035 Uiso 1 1 calc GR . . . .
C101 C 0.7860(2) 0.32734(19) 0.11269(17) 0.0175(4) Uani 1 1 d . . . . .
C102 C 0.9089(2) 0.2463(2) 0.07100(18) 0.0214(4) Uani 1 1 d . . . . .
H102 H 0.8873 0.1543 0.0312 0.026 Uiso 1 1 calc R . . . .
C103 C 1.0629(2) 0.2967(2) 0.0862(2) 0.0264(5) Uani 1 1 d . . . . .
C104 C 1.0910(2) 0.4318(2) 0.14417(19) 0.0281(5) Uani 1 1 d . . . . .
H104 H 1.1953 0.4681 0.1558 0.034 Uiso 1 1 calc R . . . .
C105 C 0.9701(3) 0.5146(2) 0.18537(19) 0.0287(5) Uani 1 1 d . . . . .
H105 H 0.9915 0.6072 0.2240 0.034 Uiso 1 1 calc R . . . .
C106 C 0.8165(2) 0.4619(2) 0.17021(18) 0.0222(4) Uani 1 1 d . . . . .
H106 H 0.7334 0.5181 0.1992 0.027 Uiso 1 1 calc R . . . .
C107 C 0.6206(2) 0.26843(19) 0.09282(17) 0.0170(4) Uani 1 1 d . . . . .
H107 H 0.5483 0.3391 0.1307 0.020 Uiso 1 1 calc R . . . .
C108 C 0.5724(2) 0.24586(19) -0.04864(17) 0.0174(4) Uani 1 1 d . . . . .
C109 C 1.1957(3) 0.2080(3) 0.0381(3) 0.0396(6) Uani 1 1 d . . . . .
H10A H 1.2650 0.1795 0.1106 0.059 Uiso 1 1 calc GR . . . .
H10B H 1.2550 0.2651 -0.0182 0.059 Uiso 1 1 calc GR . . . .
H10C H 1.1526 0.1221 -0.0091 0.059 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C7 1.426(2) . ?
O2 C8 1.217(2) . ?
O3 H3 0.8400 . ?
O3 C8 1.311(2) . ?
C1 C2 1.397(3) . ?
C1 C6 1.396(3) . ?
C1 C7 1.520(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(3) . ?
C3 C4 1.393(3) . ?
C3 C9 1.505(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.525(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O101 H101 0.8400 . ?
O101 C107 1.4287(19) . ?
O102 C108 1.215(2) . ?
O103 H103 0.8400 . ?
O103 C108 1.317(2) . ?
C101 C102 1.389(3) . ?
C101 C106 1.386(3) . ?
C101 C107 1.512(2) . ?
C102 H102 0.9500 . ?
C102 C103 1.393(3) . ?
C103 C104 1.389(3) . ?
C103 C109 1.519(3) . ?
C104 H104 0.9500 . ?
C104 C105 1.383(3) . ?
C105 H105 0.9500 . ?
C105 C106 1.396(3) . ?
C106 H106 0.9500 . ?
C107 H107 1.0000 . ?
C107 C108 1.523(2) . ?
C109 H10A 0.9800 . ?
C109 H10B 0.9800 . ?
C109 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C8 O3 H3 109.5 . . ?
C2 C1 C7 119.73(16) . . ?
C6 C1 C2 119.06(18) . . ?
C6 C1 C7 121.20(17) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.41(17) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C9 121.11(17) . . ?
C4 C3 C2 118.29(18) . . ?
C4 C3 C9 120.60(19) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.16(18) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.02(18) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 112.89(16) . . ?
O1 C7 H7 107.9 . . ?
O1 C7 C8 109.37(15) . . ?
C1 C7 H7 107.9 . . ?
C1 C7 C8 110.57(15) . . ?
C8 C7 H7 107.9 . . ?
O2 C8 O3 124.01(18) . . ?
O2 C8 C7 123.48(18) . . ?
O3 C8 C7 112.51(15) . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C107 O101 H101 109.5 . . ?
C108 O103 H103 109.5 . . ?
C102 C101 C107 119.57(17) . . ?
C106 C101 C102 119.48(17) . . ?
C106 C101 C107 120.95(17) . . ?
C101 C102 H102 119.2 . . ?
C101 C102 C103 121.60(19) . . ?
C103 C102 H102 119.2 . . ?
C102 C103 C109 121.0(2) . . ?
C104 C103 C102 118.01(19) . . ?
C104 C103 C109 120.99(19) . . ?
C103 C104 H104 119.4 . . ?
C105 C104 C103 121.24(18) . . ?
C105 C104 H104 119.4 . . ?
C104 C105 H105 120.0 . . ?
C104 C105 C106 119.96(19) . . ?
C106 C105 H105 120.0 . . ?
C101 C106 C105 119.71(19) . . ?
C101 C106 H106 120.1 . . ?
C105 C106 H106 120.1 . . ?
O101 C107 C101 110.61(13) . . ?
O101 C107 H107 108.7 . . ?
O101 C107 C108 109.49(14) . . ?
C101 C107 H107 108.7 . . ?
C101 C107 C108 110.57(14) . . ?
C108 C107 H107 108.7 . . ?
O102 C108 O103 125.15(17) . . ?
O102 C108 C107 122.71(15) . . ?
O103 C108 C107 112.14(15) . . ?
C103 C109 H10A 109.5 . . ?
C103 C109 H10B 109.5 . . ?
C103 C109 H10C 109.5 . . ?
H10A C109 H10B 109.5 . . ?
H10A C109 H10C 109.5 . . ?
H10B C109 H10C 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
O1 C7 C8 O2 -23.2(2) . . . . ?
O1 C7 C8 O3 157.19(16) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C9 -178.8(2) . . . . ?
C1 C7 C8 O2 101.7(2) . . . . ?
C1 C7 C8 O3 -77.9(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C7 O1 -99.0(2) . . . . ?
C2 C1 C7 C8 138.12(19) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C1 C7 O1 79.6(2) . . . . ?
C6 C1 C7 C8 -43.3(2) . . . . ?
C7 C1 C2 C3 179.00(18) . . . . ?
C7 C1 C6 C5 -179.7(2) . . . . ?
C9 C3 C4 C5 178.4(2) . . . . ?
O101 C107 C108 O102 -5.7(2) . . . . ?
O101 C107 C108 O103 174.03(14) . . . . ?
C101 C102 C103 C104 -0.3(3) . . . . ?
C101 C102 C103 C109 -178.95(18) . . . . ?
C101 C107 C108 O102 116.45(18) . . . . ?
C101 C107 C108 O103 -63.85(19) . . . . ?
C102 C101 C106 C105 0.1(3) . . . . ?
C102 C101 C107 O101 59.0(2) . . . . ?
C102 C101 C107 C108 -62.4(2) . . . . ?
C102 C103 C104 C105 -0.3(3) . . . . ?
C103 C104 C105 C106 0.7(3) . . . . ?
C104 C105 C106 C101 -0.6(3) . . . . ?
C106 C101 C102 C103 0.3(3) . . . . ?
C106 C101 C107 O101 -121.93(17) . . . . ?
C106 C101 C107 C108 116.61(18) . . . . ?
C107 C101 C102 C103 179.39(16) . . . . ?
C107 C101 C106 C105 -178.91(16) . . . . ?
C109 C103 C104 C105 178.42(18) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1007660'
#######################################################################
#
#                 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
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2011jms0022aa-RS-4BrMA
_audit_creation_date             2014-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H7 Br O3'
_chemical_formula_sum            'C8 H7 Br O3'
_chemical_formula_weight         231.05
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.5315(14)
_cell_length_b                   9.7410(7)
_cell_length_c                   9.1389(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.132(4)
_cell_angle_gamma                90
_cell_volume                     1706.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9395
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.780
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3843
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_min         2.982
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -110.0000 - 70.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 10.0000
	             Phi: 0.0000
	             XTD: 44.9853
	          2theta: -20.0848
scan:
	Number of images: 64
	           Slice: -62.0000 - 2.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -50.0000
	             Phi: 240.0000
	             XTD: 44.9853
	          2theta: -20.0848
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.104187
_diffrn_orient_matrix_UB_12      0.039585
_diffrn_orient_matrix_UB_13      -0.003085
_diffrn_orient_matrix_UB_21      -0.036364
_diffrn_orient_matrix_UB_22      0.094321
_diffrn_orient_matrix_UB_23      -0.017807
_diffrn_orient_matrix_UB_31      0.007561
_diffrn_orient_matrix_UB_32      0.012375
_diffrn_orient_matrix_UB_33      0.050108
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2773
_reflns_number_total             3843
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.878
_refine_diff_density_min         -1.377
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0847
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+15.2549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2205
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C28(H28), C1(H1), C33(H33), C42(H42), C48(H48), C51(H51), C56(H56)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O12(H12), O14(H14), O18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br4 Br 0.36375(5) 0.39245(13) 0.16465(19) 0.0714(5) Uani 1 1 d . . . . .
Br5 Br 0.86995(5) 0.33900(11) 0.26482(12) 0.0439(3) Uani 1 1 d . . . . .
O4 O 0.5333(3) 0.6113(6) 0.1300(6) 0.0302(13) Uani 1 1 d . . . . .
H4 H 0.5107 0.6851 0.1247 0.045 Uiso 1 1 calc GR . . . .
O7 O 0.5109(3) 0.6030(5) 0.3612(6) 0.0284(12) Uani 1 1 d . . . . .
O12 O 0.5383(3) 0.3370(5) 0.3899(6) 0.0237(11) Uani 1 1 d . . . . .
H12 H 0.5261 0.3966 0.4462 0.036 Uiso 1 1 calc GR . . . .
O14 O 0.0456(3) 0.5495(6) 0.3898(6) 0.0343(13) Uani 1 1 d . . . . .
H14 H 0.0331 0.6317 0.3936 0.052 Uiso 1 1 calc GR . . . .
O18 O 0.0158(3) 0.2965(6) 0.1074(7) 0.0332(13) Uani 1 1 d . . . . .
H18 H 0.0107 0.3498 0.0339 0.050 Uiso 1 1 calc GR . . . .
C24 C 0.6335(4) 0.3911(7) 0.2639(8) 0.0225(15) Uani 1 1 d . . . . .
O28 O -0.0083(3) 0.5671(6) 0.1539(7) 0.0336(13) Uani 1 1 d . . . . .
C29 C 0.5558(4) 0.4027(7) 0.2614(9) 0.0244(15) Uani 1 1 d . . . . .
H29 H 0.5302 0.3552 0.1700 0.029 Uiso 1 1 calc R . . . .
C6 C 0.2706(5) 0.3865(9) 0.1928(12) 0.041(2) Uani 1 1 d . . . . .
C8 C 0.6818(4) 0.4717(8) 0.3577(10) 0.0300(17) Uani 1 1 d . . . . .
H8 H 0.6663 0.5379 0.4203 0.036 Uiso 1 1 calc R . . . .
C12 C 0.1313(5) 0.3727(8) 0.2214(9) 0.0303(18) Uani 1 1 d . . . . .
C15 C 0.5314(4) 0.5506(7) 0.2574(9) 0.0243(16) Uani 1 1 d . . . . .
C21 C 0.0566(4) 0.3627(8) 0.2345(10) 0.0312(18) Uani 1 1 d . . . . .
H21 H 0.0537 0.3069 0.3250 0.037 Uiso 1 1 calc R . . . .
C28 C 0.7272(5) 0.2794(10) 0.1776(11) 0.041(2) Uani 1 1 d . . . . .
H28 H 0.7430 0.2127 0.1159 0.049 Uiso 1 1 calc R . . . .
C1 C 0.1817(5) 0.2870(10) 0.3055(11) 0.040(2) Uani 1 1 d . . . . .
H1 H 0.1680 0.2229 0.3727 0.048 Uiso 1 1 calc R . . . .
C31 C 0.7745(4) 0.3595(9) 0.2691(9) 0.0297(17) Uani 1 1 d . . . . .
C33 C 0.2511(6) 0.2941(10) 0.2926(12) 0.050(3) Uani 1 1 d . . . . .
H33 H 0.2848 0.2364 0.3514 0.060 Uiso 1 1 calc R . . . .
C42 C 0.7517(4) 0.4563(9) 0.3607(10) 0.0333(19) Uani 1 1 d . . . . .
H42 H 0.7846 0.5115 0.4252 0.040 Uiso 1 1 calc R . . . .
C48 C 0.6568(4) 0.2946(9) 0.1740(10) 0.0341(19) Uani 1 1 d . . . . .
H48 H 0.6243 0.2387 0.1096 0.041 Uiso 1 1 calc R . . . .
C51 C 0.2220(5) 0.4736(9) 0.1112(11) 0.040(2) Uani 1 1 d . . . . .
H51 H 0.2359 0.5382 0.0446 0.048 Uiso 1 1 calc R . . . .
C56 C 0.1540(5) 0.4668(9) 0.1263(10) 0.0343(19) Uani 1 1 d . . . . .
H56 H 0.1211 0.5280 0.0704 0.041 Uiso 1 1 calc R . . . .
C58 C 0.0273(4) 0.5043(8) 0.2539(10) 0.0302(17) Uani 1 1 d . . . . .


_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
Br4 C6 1.887(9) . ?
Br5 C31 1.883(8) . ?
O4 H4 0.8400 . ?
O4 C15 1.312(9) . ?
O7 C15 1.212(10) . ?
O12 H12 0.8400 . ?
O12 C29 1.436(9) . ?
O14 H14 0.8400 . ?
O14 C58 1.301(10) . ?
O18 H18 0.8400 . ?
O18 C21 1.429(10) . ?
C24 C29 1.518(10) . ?
C24 C8 1.389(11) . ?
C24 C48 1.382(11) . ?
O28 C58 1.203(10) . ?
C29 H29 1.0000 . ?
C29 C15 1.515(10) . ?
C6 C33 1.386(15) . ?
C6 C51 1.380(13) . ?
C8 H8 0.9500 . ?
C8 C42 1.368(11) . ?
C12 C21 1.491(12) . ?
C12 C1 1.401(12) . ?
C12 C56 1.393(12) . ?
C21 H21 1.0000 . ?
C21 C58 1.517(11) . ?
C28 H28 0.9500 . ?
C28 C31 1.364(12) . ?
C28 C48 1.377(12) . ?
C1 H1 0.9500 . ?
C1 C33 1.384(14) . ?
C31 C42 1.390(12) . ?
C33 H33 0.9500 . ?
C42 H42 0.9500 . ?
C48 H48 0.9500 . ?
C51 H51 0.9500 . ?
C51 C56 1.364(12) . ?
C56 H56 0.9500 . ?

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
C15 O4 H4 109.5 . . ?
C29 O12 H12 109.5 . . ?
C58 O14 H14 109.5 . . ?
C21 O18 H18 109.5 . . ?
C8 C24 C29 121.7(7) . . ?
C48 C24 C29 119.0(7) . . ?
C48 C24 C8 119.3(7) . . ?
O12 C29 C24 110.5(6) . . ?
O12 C29 H29 108.4 . . ?
O12 C29 C15 108.6(6) . . ?
C24 C29 H29 108.4 . . ?
C15 C29 C24 112.3(6) . . ?
C15 C29 H29 108.4 . . ?
C33 C6 Br4 120.3(7) . . ?
C51 C6 Br4 119.1(8) . . ?
C51 C6 C33 120.5(9) . . ?
C24 C8 H8 119.8 . . ?
C42 C8 C24 120.4(8) . . ?
C42 C8 H8 119.8 . . ?
C1 C12 C21 120.8(8) . . ?
C56 C12 C21 121.8(7) . . ?
C56 C12 C1 117.4(8) . . ?
O4 C15 C29 112.8(7) . . ?
O7 C15 O4 125.1(7) . . ?
O7 C15 C29 122.1(7) . . ?
O18 C21 C12 111.4(7) . . ?
O18 C21 H21 108.4 . . ?
O18 C21 C58 109.9(7) . . ?
C12 C21 H21 108.4 . . ?
C12 C21 C58 110.3(7) . . ?
C58 C21 H21 108.4 . . ?
C31 C28 H28 119.8 . . ?
C31 C28 C48 120.5(8) . . ?
C48 C28 H28 119.8 . . ?
C12 C1 H1 119.4 . . ?
C33 C1 C12 121.2(9) . . ?
C33 C1 H1 119.4 . . ?
C28 C31 Br5 118.8(7) . . ?
C28 C31 C42 120.0(8) . . ?
C42 C31 Br5 121.2(6) . . ?
C6 C33 H33 120.4 . . ?
C1 C33 C6 119.1(9) . . ?
C1 C33 H33 120.4 . . ?
C8 C42 C31 119.7(8) . . ?
C8 C42 H42 120.1 . . ?
C31 C42 H42 120.1 . . ?
C24 C48 H48 120.0 . . ?
C28 C48 C24 120.0(8) . . ?
C28 C48 H48 120.0 . . ?
C6 C51 H51 120.1 . . ?
C56 C51 C6 119.8(9) . . ?
C56 C51 H51 120.1 . . ?
C12 C56 H56 119.0 . . ?
C51 C56 C12 121.9(8) . . ?
C51 C56 H56 119.0 . . ?
O14 C58 C21 112.3(7) . . ?
O28 C58 O14 124.4(8) . . ?
O28 C58 C21 123.4(8) . . ?

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
Br4 C6 C33 C1 -176.7(7) . . . . ?
Br4 C6 C51 C56 177.5(7) . . . . ?
Br5 C31 C42 C8 177.9(7) . . . . ?
O12 C29 C15 O4 -167.9(6) . . . . ?
O12 C29 C15 O7 10.1(10) . . . . ?
O18 C21 C58 O14 158.0(7) . . . . ?
O18 C21 C58 O28 -22.5(11) . . . . ?
C24 C29 C15 O4 69.5(9) . . . . ?
C24 C29 C15 O7 -112.4(8) . . . . ?
C24 C8 C42 C31 0.1(13) . . . . ?
C29 C24 C8 C42 178.1(8) . . . . ?
C29 C24 C48 C28 -178.1(8) . . . . ?
C6 C51 C56 C12 -0.7(15) . . . . ?
C8 C24 C29 O12 -75.7(9) . . . . ?
C8 C24 C29 C15 45.8(10) . . . . ?
C8 C24 C48 C28 -0.3(13) . . . . ?
C12 C21 C58 O14 -78.8(9) . . . . ?
C12 C21 C58 O28 100.8(9) . . . . ?
C12 C1 C33 C6 -0.9(15) . . . . ?
C21 C12 C1 C33 179.1(9) . . . . ?
C21 C12 C56 C51 -178.2(8) . . . . ?
C28 C31 C42 C8 -0.6(13) . . . . ?
C1 C12 C21 O18 -105.4(9) . . . . ?
C1 C12 C21 C58 132.2(8) . . . . ?
C1 C12 C56 C51 2.0(13) . . . . ?
C31 C28 C48 C24 -0.2(15) . . . . ?
C33 C6 C51 C56 -1.4(15) . . . . ?
C48 C24 C29 O12 102.0(8) . . . . ?
C48 C24 C29 C15 -136.5(8) . . . . ?
C48 C24 C8 C42 0.4(12) . . . . ?
C48 C28 C31 Br5 -177.8(7) . . . . ?
C48 C28 C31 C42 0.7(14) . . . . ?
C51 C6 C33 C1 2.2(15) . . . . ?
C56 C12 C21 O18 74.7(10) . . . . ?
C56 C12 C21 C58 -47.7(11) . . . . ?
C56 C12 C1 C33 -1.1(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1007661'
#######################################################################
#
#                 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  to carry out CIF format checking respectively.
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data_2014ncs0027a-RS-4ClMA
_audit_creation_date             2014-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H7 Cl O3'
_chemical_formula_sum            'C8 H7 Cl O3'
_chemical_formula_weight         186.59
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9711(4)
_cell_length_b                   14.9062(12)
_cell_length_c                   16.7920(13)
_cell_angle_alpha                88.109(8)
_cell_angle_beta                 85.871(8)
_cell_angle_gamma                84.381(9)
_cell_volume                     1234.68(17)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    0
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1684
_diffrn_reflns_av_unetI/netI     0.3104
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8678
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         2.747
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
scan:
	Number of images: 128
	           Slice: -110.0000 - 18.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 90.0000
	             XTD: 45.0000
	          2theta: -20.0000
scan:
	Number of images: 128
	           Slice: -110.0000 - 18.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 270.0000
	             XTD: 45.0000
	          2theta: -20.0000
scan:
	Number of images: 47
	           Slice: -63.0000 - -16.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 0.0000
	             XTD: 45.0000
	          2theta: -20.0000
scan:
	Number of images: 45
	           Slice: -42.0000 - 3.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 45.0000
	          2theta: -20.0000
scan:
	Number of images: 30
	           Slice: -20.0000 - 10.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 225.0000
	             XTD: 45.0000
	          2theta: -20.0000
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.181394
_diffrn_orient_matrix_UB_12      -0.089164
_diffrn_orient_matrix_UB_13      0.015234
_diffrn_orient_matrix_UB_21      -0.035682
_diffrn_orient_matrix_UB_22      -0.057031
_diffrn_orient_matrix_UB_23      0.005010
_diffrn_orient_matrix_UB_31      -0.000972
_diffrn_orient_matrix_UB_32      -0.002784
_diffrn_orient_matrix_UB_33      -0.059673
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1427
_reflns_number_total             4218
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4218
_refine_ls_number_restraints     252
_refine_ls_R_factor_all          0.3050
_refine_ls_R_factor_gt           0.1238
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0942P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.3039
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C7(H7), C207(H207), C107(H107)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C202(H202), C203(H20A), C205(H205),
 C206(H206), C102(H102), C103(H10A), C105(H105), C106(H106)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O201(H201), O203(H203), O101(H101), O103(H103)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2330(7) 0.0966(2) -0.03028(19) 0.0657(11) Uani 1 1 d . . . . .
O1 O 0.3539(15) 0.2263(5) 0.3313(4) 0.0422(19) Uani 1 1 d . . . . .
H1 H 0.2823 0.2044 0.3735 0.063 Uiso 1 1 calc GR . . . .
O2 O 0.4338(16) 0.0713(5) 0.4136(5) 0.048(2) Uani 1 1 d . . . . .
O3 O 0.8064(17) 0.0258(5) 0.3357(5) 0.056(2) Uani 1 1 d . . . . .
H3 H 0.8418 -0.0089 0.3748 0.084 Uiso 1 1 calc GR . . . .
C1 C 0.500(2) 0.1377(7) 0.2154(7) 0.041(3) Uani 1 1 d . . . . .
C2 C 0.611(2) 0.1811(8) 0.1497(7) 0.049(3) Uani 1 1 d . . . . .
H2 H 0.7460 0.2206 0.1565 0.059 Uiso 1 1 calc R . . . .
C3 C 0.532(3) 0.1687(8) 0.0731(7) 0.052(3) Uani 1 1 d . . . . .
H3A H 0.6081 0.2002 0.0283 0.063 Uiso 1 1 calc R . . . .
C4 C 0.340(2) 0.1098(8) 0.0639(7) 0.045(3) Uani 1 1 d . . . . .
C5 C 0.229(3) 0.0656(8) 0.1288(7) 0.053(3) Uani 1 1 d . . . . .
H5 H 0.0965 0.0254 0.1220 0.064 Uiso 1 1 calc R . . . .
C6 C 0.308(3) 0.0783(8) 0.2032(7) 0.057(3) Uani 1 1 d . . . . .
H6 H 0.2302 0.0462 0.2475 0.069 Uiso 1 1 calc R . . . .
C7 C 0.561(2) 0.1617(7) 0.2978(7) 0.043(3) Uani 1 1 d . . . . .
H7 H 0.7365 0.1898 0.2937 0.051 Uiso 1 1 calc R . . . .
C8 C 0.587(3) 0.0831(8) 0.3558(7) 0.045(3) Uani 1 1 d . . . . .
Cl21 Cl 0.1945(8) 0.6813(2) 0.11219(19) 0.0664(11) Uani 1 1 d . . . . .
O201 O -0.0612(16) 0.9059(5) 0.4466(5) 0.053(2) Uani 1 1 d . . . . .
H201 H -0.1168 0.8966 0.4944 0.079 Uiso 1 1 calc GR . . . .
O202 O 0.0910(15) 0.7826(5) 0.5565(4) 0.044(2) Uani 1 1 d . . . . .
O203 O 0.4791(16) 0.7374(5) 0.4811(5) 0.048(2) Uani 1 1 d . . . . .
H203 H 0.4734 0.6864 0.5037 0.071 Uiso 1 1 calc GR . . . .
C201 C 0.202(2) 0.8128(7) 0.3495(7) 0.042(3) Uani 1 1 d . . . . .
C202 C 0.373(2) 0.8351(8) 0.2860(7) 0.053(3) Uani 1 1 d . . . . .
H202 H 0.4969 0.8783 0.2931 0.063 Uiso 1 1 calc R . . . .
C203 C 0.372(3) 0.7968(8) 0.2114(7) 0.053(3) Uani 1 1 d . . . . .
H20A H 0.4891 0.8145 0.1678 0.064 Uiso 1 1 calc R . . . .
C204 C 0.194(3) 0.7319(9) 0.2026(7) 0.053(3) Uani 1 1 d . . . . .
C205 C 0.032(2) 0.7076(8) 0.2666(7) 0.049(3) Uani 1 1 d . . . . .
H205 H -0.0852 0.6622 0.2602 0.059 Uiso 1 1 calc R . . . .
C206 C 0.030(2) 0.7454(8) 0.3401(7) 0.047(3) Uani 1 1 d . . . . .
H206 H -0.0858 0.7262 0.3836 0.056 Uiso 1 1 calc R . . . .
C207 C 0.201(2) 0.8551(7) 0.4306(7) 0.045(3) Uani 1 1 d . . . . .
H207 H 0.3464 0.8970 0.4294 0.054 Uiso 1 1 calc R . . . .
C208 C 0.238(3) 0.7880(7) 0.4969(7) 0.042(3) Uani 1 1 d . . . . .
Cl11 Cl 1.1148(7) 0.3874(2) 0.04825(19) 0.0656(11) Uani 1 1 d . . . . .
O101 O 0.3883(16) 0.3891(5) 0.4006(4) 0.044(2) Uani 1 1 d . . . . .
H101 H 0.3908 0.3495 0.3661 0.066 Uiso 1 1 calc GR . . . .
O102 O 0.7756(14) 0.4308(5) 0.4869(4) 0.0381(19) Uani 1 1 d . . . . .
O103 O 0.8469(16) 0.5531(5) 0.4109(4) 0.041(2) Uani 1 1 d . . . . .
H103 H 0.9566 0.5618 0.4450 0.062 Uiso 1 1 calc GR . . . .
C101 C 0.672(2) 0.4444(7) 0.2884(6) 0.036(2) Uani 1 1 d . . . . .
C102 C 0.598(2) 0.4940(8) 0.2211(6) 0.046(3) Uani 1 1 d . . . . .
H102 H 0.4566 0.5416 0.2260 0.055 Uiso 1 1 calc R . . . .
C103 C 0.727(3) 0.4756(8) 0.1463(7) 0.048(3) Uani 1 1 d . . . . .
H10A H 0.6666 0.5075 0.1000 0.057 Uiso 1 1 calc R . . . .
C104 C 0.947(3) 0.4094(8) 0.1404(7) 0.050(3) Uani 1 1 d . . . . .
C105 C 1.024(2) 0.3598(8) 0.2073(7) 0.045(3) Uani 1 1 d . . . . .
H105 H 1.1723 0.3145 0.2031 0.054 Uiso 1 1 calc R . . . .
C106 C 0.887(2) 0.3759(7) 0.2792(6) 0.036(2) Uani 1 1 d . . . . .
H106 H 0.9379 0.3400 0.3245 0.044 Uiso 1 1 calc R . . . .
C107 C 0.532(2) 0.4624(7) 0.3682(6) 0.036(2) Uani 1 1 d . . . . .
H107 H 0.4011 0.5176 0.3641 0.043 Uiso 1 1 calc R . . . .
C108 C 0.735(2) 0.4776(7) 0.4294(6) 0.034(3) Uani 1 1 d . . . . .


_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
Cl1 C4 1.728(12) . ?
O1 H1 0.8400 . ?
O1 C7 1.437(12) . ?
O2 C8 1.209(13) . ?
O3 H3 0.8400 . ?
O3 C8 1.348(14) . ?
C1 C2 1.369(14) . ?
C1 C6 1.396(15) . ?
C1 C7 1.499(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(15) . ?
C3 H3A 0.9500 . ?
C3 C4 1.378(15) . ?
C4 C5 1.363(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.358(16) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.501(15) . ?
Cl21 C204 1.717(13) . ?
O201 H201 0.8400 . ?
O201 C207 1.452(13) . ?
O202 C208 1.201(12) . ?
O203 H203 0.8400 . ?
O203 C208 1.366(14) . ?
C201 C202 1.368(15) . ?
C201 C206 1.401(14) . ?
C201 C207 1.520(15) . ?
C202 H202 0.9500 . ?
C202 C203 1.394(15) . ?
C203 H20A 0.9500 . ?
C203 C204 1.391(16) . ?
C204 C205 1.355(15) . ?
C205 H205 0.9500 . ?
C205 C206 1.372(15) . ?
C206 H206 0.9500 . ?
C207 H207 1.0000 . ?
C207 C208 1.480(15) . ?
Cl11 C104 1.730(12) . ?
O101 H101 0.8400 . ?
O101 C107 1.433(11) . ?
O102 C108 1.189(11) . ?
O103 H103 0.8400 . ?
O103 C108 1.323(11) . ?
C101 C102 1.383(14) . ?
C101 C106 1.407(15) . ?
C101 C107 1.486(14) . ?
C102 H102 0.9500 . ?
C102 C103 1.391(15) . ?
C103 H10A 0.9500 . ?
C103 C104 1.400(16) . ?
C104 C105 1.380(15) . ?
C105 H105 0.9500 . ?
C105 C106 1.360(14) . ?
C106 H106 0.9500 . ?
C107 H107 1.0000 . ?
C107 C108 1.528(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C8 O3 H3 109.5 . . ?
C2 C1 C6 117.6(11) . . ?
C2 C1 C7 120.5(10) . . ?
C6 C1 C7 121.6(10) . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.8(12) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 C2 118.6(11) . . ?
C4 C3 H3A 120.7 . . ?
C3 C4 Cl1 118.8(9) . . ?
C5 C4 Cl1 120.9(10) . . ?
C5 C4 C3 120.2(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(12) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(11) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C1 110.7(9) . . ?
O1 C7 H7 108.1 . . ?
O1 C7 C8 107.2(10) . . ?
C1 C7 H7 108.1 . . ?
C1 C7 C8 114.4(10) . . ?
C8 C7 H7 108.1 . . ?
O2 C8 O3 123.2(11) . . ?
O2 C8 C7 125.5(12) . . ?
O3 C8 C7 111.3(11) . . ?
C207 O201 H201 109.5 . . ?
C208 O203 H203 109.5 . . ?
C202 C201 C206 118.6(11) . . ?
C202 C201 C207 122.5(11) . . ?
C206 C201 C207 118.9(10) . . ?
C201 C202 H202 118.8 . . ?
C201 C202 C203 122.4(12) . . ?
C203 C202 H202 118.8 . . ?
C202 C203 H20A 120.9 . . ?
C204 C203 C202 118.1(11) . . ?
C204 C203 H20A 120.9 . . ?
C203 C204 Cl21 119.2(10) . . ?
C205 C204 Cl21 121.7(10) . . ?
C205 C204 C203 119.0(12) . . ?
C204 C205 H205 118.3 . . ?
C204 C205 C206 123.4(12) . . ?
C206 C205 H205 118.3 . . ?
C201 C206 H206 120.8 . . ?
C205 C206 C201 118.4(11) . . ?
C205 C206 H206 120.8 . . ?
O201 C207 C201 107.9(9) . . ?
O201 C207 H207 109.4 . . ?
O201 C207 C208 107.3(9) . . ?
C201 C207 H207 109.4 . . ?
C208 C207 C201 113.4(10) . . ?
C208 C207 H207 109.4 . . ?
O202 C208 O203 125.8(11) . . ?
O202 C208 C207 126.1(12) . . ?
O203 C208 C207 108.0(10) . . ?
C107 O101 H101 109.5 . . ?
C108 O103 H103 109.5 . . ?
C102 C101 C106 117.8(11) . . ?
C102 C101 C107 121.6(11) . . ?
C106 C101 C107 120.6(10) . . ?
C101 C102 H102 119.4 . . ?
C101 C102 C103 121.3(12) . . ?
C103 C102 H102 119.4 . . ?
C102 C103 H10A 120.5 . . ?
C102 C103 C104 118.9(11) . . ?
C104 C103 H10A 120.5 . . ?
C103 C104 Cl11 119.6(9) . . ?
C105 C104 Cl11 120.2(10) . . ?
C105 C104 C103 120.2(12) . . ?
C104 C105 H105 120.1 . . ?
C106 C105 C104 119.9(12) . . ?
C106 C105 H105 120.1 . . ?
C101 C106 H106 119.1 . . ?
C105 C106 C101 121.7(11) . . ?
C105 C106 H106 119.1 . . ?
O101 C107 C101 113.6(8) . . ?
O101 C107 H107 109.0 . . ?
O101 C107 C108 105.3(8) . . ?
C101 C107 H107 109.0 . . ?
C101 C107 C108 110.8(9) . . ?
C108 C107 H107 109.0 . . ?
O102 C108 O103 125.3(10) . . ?
O102 C108 C107 125.0(10) . . ?
O103 C108 C107 109.6(9) . . ?

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
Cl1 C4 C5 C6 -178.0(10) . . . . ?
O1 C7 C8 O2 9.8(16) . . . . ?
O1 C7 C8 O3 -169.8(9) . . . . ?
C1 C2 C3 C4 -1.3(19) . . . . ?
C1 C7 C8 O2 -113.3(14) . . . . ?
C1 C7 C8 O3 67.1(13) . . . . ?
C2 C1 C6 C5 -1.5(19) . . . . ?
C2 C1 C7 O1 95.4(12) . . . . ?
C2 C1 C7 C8 -143.4(11) . . . . ?
C2 C3 C4 Cl1 178.2(9) . . . . ?
C2 C3 C4 C5 0.5(18) . . . . ?
C3 C4 C5 C6 -0.3(19) . . . . ?
C4 C5 C6 C1 1(2) . . . . ?
C6 C1 C2 C3 1.7(18) . . . . ?
C6 C1 C7 O1 -77.7(13) . . . . ?
C6 C1 C7 C8 43.5(16) . . . . ?
C7 C1 C2 C3 -171.6(11) . . . . ?
C7 C1 C6 C5 171.8(12) . . . . ?
Cl21 C204 C205 C206 178.8(10) . . . . ?
O201 C207 C208 O202 -6.6(16) . . . . ?
O201 C207 C208 O203 177.7(9) . . . . ?
C201 C202 C203 C204 -1.7(19) . . . . ?
C201 C207 C208 O202 -125.7(12) . . . . ?
C201 C207 C208 O203 58.7(12) . . . . ?
C202 C201 C206 C205 -2.9(18) . . . . ?
C202 C201 C207 O201 116.1(12) . . . . ?
C202 C201 C207 C208 -125.2(13) . . . . ?
C202 C203 C204 Cl21 -178.2(10) . . . . ?
C202 C203 C204 C205 -0.9(18) . . . . ?
C203 C204 C205 C206 2(2) . . . . ?
C204 C205 C206 C201 0.4(19) . . . . ?
C206 C201 C202 C203 3.6(19) . . . . ?
C206 C201 C207 O201 -67.0(13) . . . . ?
C206 C201 C207 C208 51.7(15) . . . . ?
C207 C201 C202 C203 -179.4(11) . . . . ?
C207 C201 C206 C205 -180.0(10) . . . . ?
Cl11 C104 C105 C106 -178.4(8) . . . . ?
O101 C107 C108 O102 6.5(15) . . . . ?
O101 C107 C108 O103 -170.1(8) . . . . ?
C101 C102 C103 C104 -4.1(17) . . . . ?
C101 C107 C108 O102 -116.6(12) . . . . ?
C101 C107 C108 O103 66.8(11) . . . . ?
C102 C101 C106 C105 1.7(15) . . . . ?
C102 C101 C107 O101 115.3(11) . . . . ?
C102 C101 C107 C108 -126.5(11) . . . . ?
C102 C103 C104 Cl11 -178.5(8) . . . . ?
C102 C103 C104 C105 3.7(18) . . . . ?
C103 C104 C105 C106 -0.6(17) . . . . ?
C104 C105 C106 C101 -2.2(16) . . . . ?
C106 C101 C102 C103 1.5(16) . . . . ?
C106 C101 C107 O101 -64.9(13) . . . . ?
C106 C101 C107 C108 53.3(13) . . . . ?
C107 C101 C102 C103 -178.6(10) . . . . ?
C107 C101 C106 C105 -178.1(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1007662'
#######################################################################
#
#                 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_2012jms0013a-RS-4F3MeMA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 F3 O3'
_chemical_formula_sum            'C9 H7 F3 O3'
_chemical_formula_weight         220.15

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P bca'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8173(5)
_cell_length_b                   9.6920(5)
_cell_length_c                   19.9217(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1895.54(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16778
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9894
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30644
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2173
_reflns_number_gt                1123
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0285P)²+0.7024P] where P=(Fo²+2Fc²)/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         2173
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1612
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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
C4 C 0.6212(4) -0.3175(4) -0.23458(19) 0.0802(9) Uani 1 1 d . A .
C7 C 0.6285(3) -0.2776(3) -0.44837(14) 0.0571(7) Uani 1 1 d . . .
H2 H 0.6808 -0.1947 -0.4597 0.069 Uiso 1 1 calc R . .
C8 C 0.4864(3) -0.2613(3) -0.47696(13) 0.0549(7) Uani 1 1 d . . .
C5 C 0.6932(4) -0.2155(4) -0.2640(2) 0.0994(11) Uani 1 1 d . . .
H6 H 0.7425 -0.1543 -0.2375 0.119 Uiso 1 1 calc R . .
C1 C 0.6240(3) -0.2900(3) -0.37276(15) 0.0569(7) Uani 1 1 d . . .
C2 C 0.5521(3) -0.3942(3) -0.34260(18) 0.0852(10) Uani 1 1 d . . .
H4 H 0.5043 -0.4570 -0.3689 0.102 Uiso 1 1 calc R . .
C6 C 0.6946(3) -0.2010(3) -0.33288(19) 0.0867(10) Uani 1 1 d . . .
H7 H 0.7442 -0.1297 -0.3523 0.104 Uiso 1 1 calc R . .
C3 C 0.5500(4) -0.4068(4) -0.2740(2) 0.0959(11) Uani 1 1 d . . .
H5 H 0.4995 -0.4771 -0.2542 0.115 Uiso 1 1 calc R . .
F1A F 0.4975(6) -0.375(2) -0.1351(4) 0.144(5) Uani 0.69(2) 1 d P A 1
F2A F 0.7016(8) -0.4323(13) -0.1397(5) 0.133(4) Uani 0.69(2) 1 d P A 1
F3A F 0.655(3) -0.2211(12) -0.1270(4) 0.185(7) Uani 0.69(2) 1 d P A 1
F1B F 0.598(10) -0.447(4) -0.1456(9) 0.30(3) Uani 0.31(2) 1 d P A 2
F2B F 0.733(3) -0.301(8) -0.1332(10) 0.25(2) Uani 0.31(2) 1 d P A 2
F3B F 0.542(5) -0.248(5) -0.1367(9) 0.178(13) Uani 0.31(2) 1 d P A 2
C9 C 0.6192(7) -0.3329(8) -0.1606(3) 0.1150(15) Uani 1 1 d . . .
O3 O 0.69423(16) -0.39298(17) -0.47823(11) 0.0677(6) Uani 1 1 d . . .
H3 H 0.6382 -0.4540 -0.4852 0.101 Uiso 1 1 calc R . .
O1 O 0.43893(18) -0.13729(17) -0.46677(10) 0.0734(6) Uani 1 1 d . . .
H1 H 0.3622 -0.1312 -0.4828 0.110 Uiso 1 1 calc R . .
O2 O 0.42537(17) -0.35242(17) -0.50436(10) 0.0707(6) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C4 C5 1.349(4) . ?
C4 C3 1.362(4) . ?
C4 C9 1.482(6) . ?
C7 O3 1.421(3) . ?
C7 C1 1.512(4) . ?
C7 C8 1.515(4) . ?
C7 H2 0.9800 . ?
C8 O2 1.198(3) . ?
C8 O1 1.305(3) . ?
C5 C6 1.379(4) . ?
C5 H6 0.9300 . ?
C1 C6 1.362(4) . ?
C1 C2 1.371(4) . ?
C2 C3 1.372(4) . ?
C2 H4 0.9300 . ?
C6 H7 0.9300 . ?
C3 H5 0.9300 . ?
F1A C9 1.362(11) . ?
F2A C9 1.325(11) . ?
F3A C9 1.322(11) . ?
F1B C9 1.17(2) . ?
F2B C9 1.28(3) . ?
F3B C9 1.216(17) . ?
O3 H3 0.8200 . ?
O1 H1 0.8200 . ?

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
C5 C4 C3 118.9(3) . . ?
C5 C4 C9 120.9(5) . . ?
C3 C4 C9 120.2(5) . . ?
O3 C7 C1 111.6(2) . . ?
O3 C7 C8 110.1(2) . . ?
C1 C7 C8 110.9(2) . . ?
O3 C7 H2 108.1 . . ?
C1 C7 H2 108.1 . . ?
C8 C7 H2 108.1 . . ?
O2 C8 O1 124.8(2) . . ?
O2 C8 C7 123.7(2) . . ?
O1 C8 C7 111.5(2) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H6 119.6 . . ?
C6 C5 H6 119.6 . . ?
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 121.1(3) . . ?
C2 C1 C7 120.7(3) . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H4 119.7 . . ?
C3 C2 H4 119.7 . . ?
C1 C6 C5 120.7(3) . . ?
C1 C6 H7 119.7 . . ?
C5 C6 H7 119.7 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H5 119.7 . . ?
C2 C3 H5 119.7 . . ?
F1B C9 F3B 116(3) . . ?
F1B C9 F2B 106(2) . . ?
F3B C9 F2B 102.2(16) . . ?
F1B C9 F3A 134.2(14) . . ?
F3B C9 F3A 54.1(18) . . ?
F2B C9 F3A 50(2) . . ?
F1B C9 F2A 49(5) . . ?
F3B C9 F2A 138.6(11) . . ?
F2B C9 F2A 61(3) . . ?
F3A C9 F2A 105.8(9) . . ?
F1B C9 F1A 57(4) . . ?
F3B C9 F1A 61(2) . . ?
F2B C9 F1A 132.8(14) . . ?
F3A C9 F1A 107.1(9) . . ?
F2A C9 F1A 101.5(9) . . ?
F1B C9 C4 110.6(12) . . ?
F3B C9 C4 109.2(11) . . ?
F2B C9 C4 112.8(14) . . ?
F3A C9 C4 114.7(7) . . ?
F2A C9 C4 112.2(6) . . ?
F1A C9 C4 114.4(6) . . ?
C7 O3 H3 109.5 . . ?
C8 O1 H1 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
O3 C7 C8 O2 20.3(4) . . . . ?
C1 C7 C8 O2 -103.7(3) . . . . ?
O3 C7 C8 O1 -160.9(2) . . . . ?
C1 C7 C8 O1 75.2(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C9 C4 C5 C6 -179.8(4) . . . . ?
O3 C7 C1 C6 113.8(3) . . . . ?
C8 C7 C1 C6 -123.2(3) . . . . ?
O3 C7 C1 C2 -64.0(3) . . . . ?
C8 C7 C1 C2 59.0(3) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C7 C1 C2 C3 178.8(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C7 C1 C6 C5 -178.0(3) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C5 C4 C3 C2 0.4(5) . . . . ?
C9 C4 C3 C2 -179.4(4) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C5 C4 C9 F1B -154(5) . . . . ?
C3 C4 C9 F1B 26(6) . . . . ?
C5 C4 C9 F3B 78(3) . . . . ?
C3 C4 C9 F3B -102(3) . . . . ?
C5 C4 C9 F2B -35(4) . . . . ?
C3 C4 C9 F2B 145(4) . . . . ?
C5 C4 C9 F3A 19.5(17) . . . . ?
C3 C4 C9 F3A -160.6(15) . . . . ?
C5 C4 C9 F2A -101.3(10) . . . . ?
C3 C4 C9 F2A 78.6(9) . . . . ?
C5 C4 C9 F1A 143.8(10) . . . . ?
C3 C4 C9 F1A -36.3(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.026
_database_code_depnum_ccdc_archive 'CCDC 1007663'
#######################################################################
#
#                 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_2012jms0007a-RS-4IMA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 I O3'
_chemical_formula_sum            'C8 H7 I O3'
_chemical_formula_weight         278.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9583(5)
_cell_length_b                   10.3607(11)
_cell_length_c                   17.675(2)
_cell_angle_alpha                76.455(5)
_cell_angle_beta                 83.237(6)
_cell_angle_gamma                88.779(6)
_cell_volume                     876.58(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6716
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    3.616
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8571
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4017
_reflns_number_gt                2837
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0752P)²+5.8796P] where P=(Fo²+2Fc²)/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         4017
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1692
_refine_ls_wR_factor_gt          0.1576
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C4 C 1.0032(19) 0.6298(8) 0.3281(5) 0.0198(18) Uani 1 1 d . . .
C14 C 0.6375(17) 0.1338(8) 0.3302(5) 0.0148(16) Uani 1 1 d . . .
C2 C 1.3131(18) 0.4902(8) 0.2701(5) 0.0189(18) Uani 1 1 d . . .
H4 H 1.4565 0.4275 0.2743 0.023 Uiso 1 1 calc R . .
C13 C 0.447(2) 0.0350(9) 0.3374(5) 0.0238(19) Uani 1 1 d . . .
H15 H 0.3617 -0.0100 0.3873 0.029 Uiso 1 1 calc R . .
C11 C 0.5034(17) 0.0709(8) 0.1957(5) 0.0147(16) Uani 1 1 d . . .
C15 C 0.7617(17) 0.2049(8) 0.2577(5) 0.0151(16) Uani 1 1 d . . .
H16 H 0.8896 0.2737 0.2541 0.018 Uiso 1 1 calc R . .
C5 C 0.8983(19) 0.6771(9) 0.2572(5) 0.0221(19) Uani 1 1 d . . .
H6 H 0.7569 0.7408 0.2528 0.027 Uiso 1 1 calc R . .
C1 C 1.2095(16) 0.5355(8) 0.1989(5) 0.0145(16) Uani 1 1 d . . .
C12 C 0.3833(18) 0.0036(8) 0.2693(5) 0.0193(18) Uani 1 1 d . . .
H14 H 0.2554 -0.0652 0.2730 0.023 Uiso 1 1 calc R . .
C17 C 0.4268(16) 0.0427(8) 0.1200(5) 0.0139(16) Uani 1 1 d . . .
H12 H 0.3160 -0.0408 0.1331 0.017 Uiso 1 1 calc R . .
C7 C 1.3230(17) 0.4812(8) 0.1294(5) 0.0149(16) Uani 1 1 d . . .
H2 H 1.5003 0.4370 0.1403 0.018 Uiso 1 1 calc R . .
C8 C 1.3689(16) 0.5924(7) 0.0550(4) 0.0125(15) Uani 1 1 d . . .
C16 C 0.6907(16) 0.1711(8) 0.1910(5) 0.0145(16) Uani 1 1 d . . .
H17 H 0.7722 0.2176 0.1409 0.017 Uiso 1 1 calc R . .
C18 C 0.6805(16) 0.0239(8) 0.0674(5) 0.0140(16) Uani 1 1 d . . .
C3 C 1.2068(19) 0.5367(9) 0.3355(5) 0.0214(19) Uani 1 1 d . . .
H5 H 1.2743 0.5045 0.3846 0.026 Uiso 1 1 calc R . .
C6 C 1.0053(18) 0.6288(8) 0.1929(5) 0.0182(17) Uani 1 1 d . . .
H7 H 0.9366 0.6605 0.1440 0.022 Uiso 1 1 calc R . .
I2 I 0.74129(13) 0.18636(6) 0.43082(3) 0.0260(2) Uani 1 1 d . . .
I1 I 0.83347(13) 0.69940(6) 0.42519(3) 0.0285(2) Uani 1 1 d . . .
O2 O 1.2410(11) 0.6019(5) 0.0001(3) 0.0144(11) Uani 1 1 d . . .
O12 O 0.7398(11) 0.0965(5) 0.0026(3) 0.0116(11) Uani 1 1 d . . .
O3 O 1.1424(12) 0.3870(5) 0.1145(3) 0.0168(12) Uani 1 1 d . . .
H3 H 1.0715 0.4205 0.0735 0.025 Uiso 1 1 calc R . .
O1 O 1.5628(12) 0.6731(6) 0.0607(3) 0.0169(12) Uani 1 1 d . . .
H1 H 1.5828 0.7349 0.0201 0.025 Uiso 1 1 calc R . .
O13 O 0.2767(12) 0.1463(6) 0.0777(3) 0.0164(12) Uani 1 1 d . . .
H13 H 0.2392 0.2030 0.1044 0.025 Uiso 1 1 calc R . .
O11 O 0.8217(11) -0.0827(5) 0.0964(3) 0.0144(11) Uani 1 1 d . . .
H11 H 0.9628 -0.0866 0.0657 0.022 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C4 C3 1.377(12) . ?
C4 C5 1.391(12) . ?
C4 I1 2.095(8) . ?
C14 C13 1.382(12) . ?
C14 C15 1.399(11) . ?
C14 I2 2.099(7) . ?
C2 C1 1.390(11) . ?
C2 C3 1.398(11) . ?
C2 H4 0.9500 . ?
C13 C12 1.390(11) . ?
C13 H15 0.9500 . ?
C11 C16 1.389(11) . ?
C11 C12 1.394(11) . ?
C11 C17 1.526(11) . ?
C15 C16 1.391(10) . ?
C15 H16 0.9500 . ?
C5 C6 1.392(12) . ?
C5 H6 0.9500 . ?
C1 C6 1.381(12) . ?
C1 C7 1.513(11) . ?
C12 H14 0.9500 . ?
C17 O13 1.409(9) . ?
C17 C18 1.512(11) . ?
C17 H12 1.0000 . ?
C7 O3 1.427(9) . ?
C7 C8 1.530(11) . ?
C7 H2 1.0000 . ?
C8 O2 1.204(9) . ?
C8 O1 1.315(10) . ?
C16 H17 0.9500 . ?
C18 O12 1.221(10) . ?
C18 O11 1.327(9) . ?
C3 H5 0.9500 . ?
C6 H7 0.9500 . ?
O3 H3 0.8400 . ?
O1 H1 0.8400 . ?
O13 H13 0.8400 . ?
O11 H11 0.8400 . ?

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
C3 C4 C5 121.5(8) . . ?
C3 C4 I1 120.4(6) . . ?
C5 C4 I1 118.1(6) . . ?
C13 C14 C15 122.8(7) . . ?
C13 C14 I2 119.8(6) . . ?
C15 C14 I2 117.4(6) . . ?
C1 C2 C3 120.2(8) . . ?
C1 C2 H4 119.9 . . ?
C3 C2 H4 119.9 . . ?
C14 C13 C12 117.9(8) . . ?
C14 C13 H15 121.0 . . ?
C12 C13 H15 121.0 . . ?
C16 C11 C12 118.9(7) . . ?
C16 C11 C17 118.8(7) . . ?
C12 C11 C17 122.3(7) . . ?
C16 C15 C14 117.4(7) . . ?
C16 C15 H16 121.3 . . ?
C14 C15 H16 121.3 . . ?
C4 C5 C6 118.4(8) . . ?
C4 C5 H6 120.8 . . ?
C6 C5 H6 120.8 . . ?
C6 C1 C2 119.5(8) . . ?
C6 C1 C7 121.3(7) . . ?
C2 C1 C7 119.2(7) . . ?
C13 C12 C11 121.4(8) . . ?
C13 C12 H14 119.3 . . ?
C11 C12 H14 119.3 . . ?
O13 C17 C18 107.7(6) . . ?
O13 C17 C11 112.7(6) . . ?
C18 C17 C11 109.9(6) . . ?
O13 C17 H12 108.8 . . ?
C18 C17 H12 108.8 . . ?
C11 C17 H12 108.8 . . ?
O3 C7 C1 111.6(7) . . ?
O3 C7 C8 107.2(6) . . ?
C1 C7 C8 111.0(6) . . ?
O3 C7 H2 109.0 . . ?
C1 C7 H2 109.0 . . ?
C8 C7 H2 109.0 . . ?
O2 C8 O1 126.4(7) . . ?
O2 C8 C7 123.2(7) . . ?
O1 C8 C7 110.4(6) . . ?
C11 C16 C15 121.6(7) . . ?
C11 C16 H17 119.2 . . ?
C15 C16 H17 119.2 . . ?
O12 C18 O11 123.7(7) . . ?
O12 C18 C17 122.6(7) . . ?
O11 C18 C17 113.6(7) . . ?
C4 C3 C2 119.2(7) . . ?
C4 C3 H5 120.4 . . ?
C2 C3 H5 120.4 . . ?
C1 C6 C5 121.2(8) . . ?
C1 C6 H7 119.4 . . ?
C5 C6 H7 119.4 . . ?
C7 O3 H3 109.5 . . ?
C8 O1 H1 109.5 . . ?
C17 O13 H13 109.5 . . ?
C18 O11 H11 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
C15 C14 C13 C12 1.9(14) . . . . ?
I2 C14 C13 C12 179.8(7) . . . . ?
C13 C14 C15 C16 -1.3(13) . . . . ?
I2 C14 C15 C16 -179.3(6) . . . . ?
C3 C4 C5 C6 -0.4(14) . . . . ?
I1 C4 C5 C6 -178.4(7) . . . . ?
C3 C2 C1 C6 1.4(13) . . . . ?
C3 C2 C1 C7 -178.5(8) . . . . ?
C14 C13 C12 C11 -1.2(14) . . . . ?
C16 C11 C12 C13 0.2(13) . . . . ?
C17 C11 C12 C13 -177.0(8) . . . . ?
C16 C11 C17 O13 -68.6(9) . . . . ?
C12 C11 C17 O13 108.6(9) . . . . ?
C16 C11 C17 C18 51.5(9) . . . . ?
C12 C11 C17 C18 -131.3(8) . . . . ?
C6 C1 C7 O3 -76.0(9) . . . . ?
C2 C1 C7 O3 103.9(9) . . . . ?
C6 C1 C7 C8 43.5(10) . . . . ?
C2 C1 C7 C8 -136.6(8) . . . . ?
O3 C7 C8 O2 9.1(11) . . . . ?
C1 C7 C8 O2 -113.1(8) . . . . ?
O3 C7 C8 O1 -171.2(6) . . . . ?
C1 C7 C8 O1 66.7(8) . . . . ?
C12 C11 C16 C15 0.4(12) . . . . ?
C17 C11 C16 C15 177.6(7) . . . . ?
C14 C15 C16 C11 0.2(12) . . . . ?
O13 C17 C18 O12 4.8(10) . . . . ?
C11 C17 C18 O12 -118.3(8) . . . . ?
O13 C17 C18 O11 -171.4(6) . . . . ?
C11 C17 C18 O11 65.5(8) . . . . ?
C5 C4 C3 C2 1.0(14) . . . . ?
I1 C4 C3 C2 178.9(7) . . . . ?
C1 C2 C3 C4 -1.5(14) . . . . ?
C2 C1 C6 C5 -0.9(13) . . . . ?
C7 C1 C6 C5 179.0(8) . . . . ?
C4 C5 C6 C1 0.4(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         3.722
_refine_diff_density_min         -1.624
_refine_diff_density_rms         0.261
_database_code_depnum_ccdc_archive 'CCDC 1007664'
#######################################################################
#
#                 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_racemate4methylmandelicacid-RS-4MeMA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_weight         166.17

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  -P2ac2ab

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.8365(7)
_cell_length_b                   9.4215(7)
_cell_length_c                   19.2390(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1783.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5376
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9807
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15878
_diffrn_reflns_av_R_equivalents  0.1212
_diffrn_reflns_av_sigmaI/netI    0.0888
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2038
_reflns_number_gt                790
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0923P)²+0.0700P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2038
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1920
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.2198
_refine_ls_wR_factor_gt          0.1594
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
O2 O 0.4254(2) 0.1316(2) 0.46160(14) 0.0917(9) Uani 1 1 d . . .
H2 H 0.3471 0.1287 0.4789 0.138 Uiso 1 1 calc R . .
O1 O 0.68806(19) 0.3877(2) 0.47687(12) 0.0887(8) Uani 1 1 d . . .
H1 H 0.6362 0.4585 0.4767 0.133 Uiso 1 1 calc R . .
O3 O 0.4212(2) 0.3501(2) 0.50439(14) 0.0966(9) Uani 1 1 d . . .
C8 C 0.6213(3) 0.2704(3) 0.44434(17) 0.0759(9) Uani 1 1 d . . .
H8 H 0.6726 0.1823 0.4567 0.091 Uiso 1 1 calc R . .
C9 C 0.4796(3) 0.2565(3) 0.47352(18) 0.0757(9) Uani 1 1 d . . .
C5 C 0.6200(3) 0.2830(3) 0.36637(18) 0.0763(9) Uani 1 1 d . . .
C4 C 0.5413(4) 0.3823(4) 0.3332(2) 0.1061(12) Uani 1 1 d . . .
H4 H 0.4844 0.4432 0.3596 0.127 Uiso 1 1 calc R . .
C2 C 0.6233(5) 0.3085(5) 0.2214(2) 0.1071(12) Uani 1 1 d . . .
C6 C 0.7007(4) 0.1981(4) 0.3255(2) 0.1027(12) Uani 1 1 d . . .
H6 H 0.7569 0.1286 0.3468 0.123 Uiso 1 1 calc R . .
C3 C 0.5440(5) 0.3945(4) 0.2612(3) 0.1165(14) Uani 1 1 d . . .
H3 H 0.4892 0.4645 0.2393 0.140 Uiso 1 1 calc R . .
C7 C 0.7016(5) 0.2119(5) 0.2539(2) 0.1213(14) Uani 1 1 d . . .
H7 H 0.7587 0.1518 0.2271 0.146 Uiso 1 1 calc R . .
C1 C 0.6222(6) 0.3231(6) 0.1425(2) 0.161(2) Uani 1 1 d . . .
H1A H 0.5406 0.3750 0.1281 0.242 Uiso 1 1 calc R . .
H1B H 0.6220 0.2286 0.1213 0.242 Uiso 1 1 calc R . .
H1C H 0.7033 0.3752 0.1275 0.242 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O2 C9 1.311(3) . ?
O2 H2 0.8400 . ?
O1 C8 1.430(3) . ?
O1 H1 0.8400 . ?
O3 C9 1.209(3) . ?
C8 C5 1.505(4) . ?
C8 C9 1.508(5) . ?
C8 H8 1.0000 . ?
C5 C4 1.372(5) . ?
C5 C6 1.374(4) . ?
C4 C3 1.389(6) . ?
C4 H4 0.9500 . ?
C2 C7 1.346(6) . ?
C2 C3 1.361(6) . ?
C2 C1 1.524(5) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C7 H7 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 109.5 . . ?
C8 O1 H1 109.5 . . ?
O1 C8 C5 112.3(3) . . ?
O1 C8 C9 109.2(3) . . ?
C5 C8 C9 111.7(3) . . ?
O1 C8 H8 107.8 . . ?
C5 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
O3 C9 O2 123.2(3) . . ?
O3 C9 C8 124.0(3) . . ?
O2 C9 C8 112.8(3) . . ?
C4 C5 C6 117.1(4) . . ?
C4 C5 C8 121.5(3) . . ?
C6 C5 C8 121.3(3) . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C7 C2 C3 118.0(4) . . ?
C7 C2 C1 121.9(5) . . ?
C3 C2 C1 120.2(5) . . ?
C5 C6 C7 121.3(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C2 C7 C6 121.5(4) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84 1.79 2.624(3) 174.0 4_456
O1 H1 O3 0.84 1.92 2.718(3) 157.2 5_666

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1007665'
#######################################################################
#
#                 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_2011jms0016ba-RS-4MeOMA-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 O4'
_chemical_formula_sum            'C9 H10 O4'
_chemical_formula_weight         182.17

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P bca'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.805(3)
_cell_length_b                   15.649(3)
_cell_length_c                   5.3033(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1726.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8617
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16890
_diffrn_reflns_av_R_equivalents  0.1451
_diffrn_reflns_av_sigmaI/netI    0.1102
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         27.43
_reflns_number_total             1971
_reflns_number_gt                832
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0439P)²+0.0000P] where P=(Fo²+2Fc²)/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         1971
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1957
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
O4 O 0.84864(10) 0.12391(14) 0.1864(4) 0.0591(7) Uani 1 1 d . . .
O2 O 0.51526(11) 0.09948(13) 0.4343(4) 0.0545(6) Uani 1 1 d . . .
O1 O 0.55533(13) -0.01268(13) 0.2319(4) 0.0680(8) Uani 1 1 d . . .
H1 H 0.5397 -0.0386 0.3517 0.102 Uiso 1 1 calc R . .
O3 O 0.55203(11) 0.20579(13) 0.0591(4) 0.0522(6) Uani 1 1 d . . .
H3 H 0.5489 0.2243 0.2032 0.078 Uiso 1 1 calc R . .
C1 C 0.65115(14) 0.12191(18) 0.1045(5) 0.0377(8) Uani 1 1 d . . .
C4 C 0.78330(15) 0.1248(2) 0.1723(6) 0.0426(8) Uani 1 1 d . . .
C8 C 0.54617(15) 0.0698(2) 0.2621(6) 0.0423(8) Uani 1 1 d . . .
C9 C 0.87741(16) 0.1691(2) 0.3899(7) 0.0702(11) Uani 1 1 d . . .
H8 H 0.8630 0.2274 0.3882 0.105 Uiso 1 1 calc R . .
H9 H 0.9233 0.1677 0.3724 0.105 Uiso 1 1 calc R . .
H10 H 0.8654 0.1428 0.5465 0.105 Uiso 1 1 calc R . .
C2 C 0.67811(15) 0.16431(19) 0.3061(6) 0.0430(8) Uani 1 1 d . . .
H4 H 0.6515 0.1921 0.4207 0.052 Uiso 1 1 calc R . .
C5 C 0.75683(16) 0.0815(2) -0.0270(6) 0.0468(9) Uani 1 1 d . . .
H6 H 0.7834 0.0530 -0.1402 0.056 Uiso 1 1 calc R . .
C7 C 0.57898(14) 0.12315(19) 0.0656(6) 0.0417(8) Uani 1 1 d . . .
H2 H 0.5704 0.0965 -0.0982 0.050 Uiso 1 1 calc R . .
C6 C 0.69136(15) 0.07968(18) -0.0609(5) 0.0430(8) Uani 1 1 d . . .
H7 H 0.6740 0.0498 -0.1963 0.052 Uiso 1 1 calc R . .
C3 C 0.74338(16) 0.16632(19) 0.3409(6) 0.0432(8) Uani 1 1 d . . .
H5 H 0.7608 0.1955 0.4776 0.052 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O4 C4 1.362(3) . ?
O4 C9 1.423(4) . ?
O2 C8 1.209(3) . ?
O1 C8 1.314(3) . ?
O1 H1 0.8200 . ?
O3 C7 1.410(3) . ?
O3 H3 0.8200 . ?
C1 C2 1.377(4) . ?
C1 C6 1.381(4) . ?
C1 C7 1.516(4) . ?
C4 C5 1.371(4) . ?
C4 C3 1.383(4) . ?
C8 C7 1.500(4) . ?
C9 H8 0.9600 . ?
C9 H9 0.9600 . ?
C9 H10 0.9600 . ?
C2 C3 1.371(4) . ?
C2 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H6 0.9300 . ?
C7 H2 0.9800 . ?
C6 H7 0.9300 . ?
C3 H5 0.9300 . ?

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
C4 O4 C9 117.2(3) . . ?
C8 O1 H1 109.5 . . ?
C7 O3 H3 109.5 . . ?
C2 C1 C6 118.5(3) . . ?
C2 C1 C7 120.2(3) . . ?
C6 C1 C7 121.3(3) . . ?
O4 C4 C5 116.0(3) . . ?
O4 C4 C3 124.7(3) . . ?
C5 C4 C3 119.3(3) . . ?
O2 C8 O1 123.1(3) . . ?
O2 C8 C7 123.5(3) . . ?
O1 C8 C7 113.3(3) . . ?
O4 C9 H8 109.5 . . ?
O4 C9 H9 109.5 . . ?
H8 C9 H9 109.5 . . ?
O4 C9 H10 109.5 . . ?
H8 C9 H10 109.5 . . ?
H9 C9 H10 109.5 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H4 119.4 . . ?
C1 C2 H4 119.4 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H6 119.7 . . ?
C6 C5 H6 119.7 . . ?
O3 C7 C8 110.3(2) . . ?
O3 C7 C1 114.1(2) . . ?
C8 C7 C1 110.4(3) . . ?
O3 C7 H2 107.2 . . ?
C8 C7 H2 107.2 . . ?
C1 C7 H2 107.2 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H7 119.7 . . ?
C1 C6 H7 119.7 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H5 120.1 . . ?
C4 C3 H5 120.1 . . ?

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
C9 O4 C4 C5 179.4(3) . . . . ?
C9 O4 C4 C3 0.0(4) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C7 C1 C2 C3 -178.0(3) . . . . ?
O4 C4 C5 C6 -178.9(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
O2 C8 C7 O3 -19.5(4) . . . . ?
O1 C8 C7 O3 161.8(3) . . . . ?
O2 C8 C7 C1 107.6(3) . . . . ?
O1 C8 C7 C1 -71.2(3) . . . . ?
C2 C1 C7 O3 53.7(4) . . . . ?
C6 C1 C7 O3 -125.4(3) . . . . ?
C2 C1 C7 C8 -71.2(3) . . . . ?
C6 C1 C7 C8 109.7(3) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C7 C1 C6 C5 178.0(3) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
O4 C4 C3 C2 178.8(3) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 1007666'
#######################################################################
#
#                 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_2011jms0005a-RS-4MeOMA-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 O4'
_chemical_formula_sum            'C9 H10 O4'
_chemical_formula_weight         182.17

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.6794(13)
_cell_length_b                   5.1376(2)
_cell_length_c                   9.214(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.682(12)
_cell_angle_gamma                90.00
_cell_volume                     859.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15095
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9867
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18014
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1971
_reflns_number_gt                1584
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0439P)²+0.1478P] where P=(Fo²+2Fc²)/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         1971
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
O4 O 0.41343(5) 0.5693(2) 0.12523(14) 0.0693(4) Uani 1 1 d . . .
O1 O 0.06547(5) 0.66955(16) -0.08340(10) 0.0384(2) Uani 1 1 d . . .
H1 H 0.0347 0.6903 -0.0341 0.058 Uiso 1 1 calc R . .
O2 O 0.03142(4) 0.25228(16) -0.08035(10) 0.0375(2) Uani 1 1 d . . .
O3 O 0.11539(5) 0.10416(17) -0.26091(10) 0.0425(2) Uani 1 1 d . . .
H3 H 0.0990 0.0162 -0.2018 0.064 Uiso 1 1 calc R . .
C9 C 0.45596(9) 0.7744(4) 0.0842(3) 0.0849(6) Uani 1 1 d . . .
H9 H 0.4626 0.7433 -0.0145 0.127 Uiso 1 1 calc R . .
H10 H 0.5032 0.7812 0.1536 0.127 Uiso 1 1 calc R . .
H8 H 0.4308 0.9369 0.0859 0.127 Uiso 1 1 calc R . .
C1 C 0.20117(6) 0.4271(2) -0.12392(13) 0.0334(3) Uani 1 1 d . . .
C5 C 0.31292(7) 0.6776(3) -0.08837(17) 0.0486(3) Uani 1 1 d . . .
H6 H 0.3398 0.8096 -0.1198 0.058 Uiso 1 1 calc R . .
C8 C 0.06830(6) 0.4230(2) -0.11776(12) 0.0306(3) Uani 1 1 d . . .
C2 C 0.23311(7) 0.2838(3) 0.00240(15) 0.0435(3) Uani 1 1 d . . .
H4 H 0.2065 0.1502 0.0331 0.052 Uiso 1 1 calc R . .
C7 C 0.12339(6) 0.3651(2) -0.21088(13) 0.0338(3) Uani 1 1 d . . .
H2 H 0.1119 0.4783 -0.2989 0.041 Uiso 1 1 calc R . .
C4 C 0.34368(7) 0.5332(3) 0.03737(16) 0.0463(3) Uani 1 1 d . . .
C6 C 0.24151(7) 0.6241(3) -0.16744(15) 0.0412(3) Uani 1 1 d . . .
H7 H 0.2205 0.7229 -0.2513 0.049 Uiso 1 1 calc R . .
C3 C 0.30346(7) 0.3362(3) 0.08291(16) 0.0500(4) Uani 1 1 d . . .
H5 H 0.3240 0.2395 0.1679 0.060 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O4 C4 1.3741(16) . ?
O4 C9 1.423(2) . ?
O1 C8 1.3096(14) . ?
O1 H1 0.8200 . ?
O2 C8 1.2146(14) . ?
O3 C7 1.4142(15) . ?
O3 H3 0.8200 . ?
C9 H9 0.9600 . ?
C9 H10 0.9600 . ?
C9 H8 0.9600 . ?
C1 C6 1.3767(17) . ?
C1 C2 1.3872(17) . ?
C1 C7 1.5177(16) . ?
C5 C4 1.381(2) . ?
C5 C6 1.3879(19) . ?
C5 H6 0.9300 . ?
C8 C7 1.5170(16) . ?
C2 C3 1.3742(18) . ?
C2 H4 0.9300 . ?
C7 H2 0.9800 . ?
C4 C3 1.383(2) . ?
C6 H7 0.9300 . ?
C3 H5 0.9300 . ?

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
C4 O4 C9 117.04(14) . . ?
C8 O1 H1 109.5 . . ?
C7 O3 H3 109.5 . . ?
O4 C9 H9 109.5 . . ?
O4 C9 H10 109.5 . . ?
H9 C9 H10 109.5 . . ?
O4 C9 H8 109.5 . . ?
H9 C9 H8 109.5 . . ?
H10 C9 H8 109.5 . . ?
C6 C1 C2 118.56(11) . . ?
C6 C1 C7 121.47(11) . . ?
C2 C1 C7 119.97(11) . . ?
C4 C5 C6 119.42(12) . . ?
C4 C5 H6 120.3 . . ?
C6 C5 H6 120.3 . . ?
O2 C8 O1 124.88(10) . . ?
O2 C8 C7 121.67(10) . . ?
O1 C8 C7 113.44(10) . . ?
C3 C2 C1 121.03(12) . . ?
C3 C2 H4 119.5 . . ?
C1 C2 H4 119.5 . . ?
O3 C7 C8 109.68(9) . . ?
O3 C7 C1 112.65(9) . . ?
C8 C7 C1 110.67(9) . . ?
O3 C7 H2 107.9 . . ?
C8 C7 H2 107.9 . . ?
C1 C7 H2 107.9 . . ?
O4 C4 C5 124.74(13) . . ?
O4 C4 C3 115.30(13) . . ?
C5 C4 C3 119.96(12) . . ?
C1 C6 C5 121.14(12) . . ?
C1 C6 H7 119.4 . . ?
C5 C6 H7 119.4 . . ?
C2 C3 C4 119.89(13) . . ?
C2 C3 H5 120.1 . . ?
C4 C3 H5 120.1 . . ?

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
C6 C1 C2 C3 0.0(2) . . . . ?
C7 C1 C2 C3 179.97(12) . . . . ?
O2 C8 C7 O3 8.61(15) . . . . ?
O1 C8 C7 O3 -171.58(9) . . . . ?
O2 C8 C7 C1 -116.30(12) . . . . ?
O1 C8 C7 C1 63.52(13) . . . . ?
C6 C1 C7 O3 122.56(12) . . . . ?
C2 C1 C7 O3 -57.39(14) . . . . ?
C6 C1 C7 C8 -114.24(12) . . . . ?
C2 C1 C7 C8 65.81(14) . . . . ?
C9 O4 C4 C5 1.3(2) . . . . ?
C9 O4 C4 C3 -178.50(15) . . . . ?
C6 C5 C4 O4 -179.46(14) . . . . ?
C6 C5 C4 C3 0.4(2) . . . . ?
C2 C1 C6 C5 0.72(19) . . . . ?
C7 C1 C6 C5 -179.23(12) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
O4 C4 C3 C2 -179.81(14) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 1007667'
#######################################################################
#
#                 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_2012tsb0006a-RS-3FMA-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 F O3'
_chemical_formula_sum            'C8 H7 F O3'
_chemical_formula_weight         170.14

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0748(10)
_cell_length_b                   5.2814(10)
_cell_length_c                   15.032(4)
_cell_angle_alpha                91.142(7)
_cell_angle_beta                 92.370(7)
_cell_angle_gamma                111.420(8)
_cell_volume                     374.47(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2367
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      27.4

_exptl_crystal_description       lath
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             176
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax'
_diffrn_source                   'Rotating Anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            3166
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.07
_diffrn_reflns_theta_max         27.45
_reflns_number_total             1677
_reflns_number_gt                1128
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0535P)²+0.4486P] where P=(Fo²+2Fc²)/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         1677
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1666
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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 0.2544(5) 0.7633(5) 0.2310(2) 0.0168(6) Uani 1 1 d . . .
C2 C 0.1128(6) 0.9025(6) 0.2773(2) 0.0217(7) Uani 1 1 d . C .
H2 H 0.0181 1.0018 0.2460 0.026 Uiso 1 1 calc R . .
C3 C 0.1114(6) 0.8949(6) 0.3682(2) 0.0243(7) Uani 1 1 d . . .
H3A H 0.0146 0.9900 0.3992 0.029 Uiso 0.50 1 calc PR A 2
C4 C 0.2483(6) 0.7511(6) 0.4167(2) 0.0251(7) Uani 1 1 d . C .
H4 H 0.2462 0.7476 0.4798 0.030 Uiso 1 1 calc R . .
C5 C 0.3863(6) 0.6150(6) 0.3697(2) 0.0243(7) Uani 1 1 d . . .
H5 H 0.4801 0.5155 0.4014 0.029 Uiso 0.50 1 calc PR B 1
C6 C 0.3925(6) 0.6185(5) 0.2777(2) 0.0223(7) Uani 1 1 d . C .
H6 H 0.4898 0.5234 0.2468 0.027 Uiso 1 1 calc R . .
C7 C 0.2601(5) 0.7741(5) 0.1305(2) 0.0173(6) Uani 1 1 d . . .
H7 H 0.3619 0.6563 0.1088 0.021 Uiso 1 1 calc R . .
C8 C 0.4128(5) 1.0614(5) 0.10041(19) 0.0163(6) Uani 1 1 d . . .
F1A F -0.0182(7) 1.0433(7) 0.4130(3) 0.0311(9) Uani 0.50 1 d P C 1
F1B F 0.5372(8) 0.4836(7) 0.4131(3) 0.0324(9) Uani 0.50 1 d P C 2
O1 O 0.3041(4) 1.1739(4) 0.04910(14) 0.0210(5) Uani 1 1 d . . .
O2 O 0.6749(4) 1.1702(4) 0.13557(15) 0.0216(5) Uani 1 1 d . . .
H2A H 0.7557 1.3244 0.1148 0.032 Uiso 1 1 calc R . .
O3 O -0.0225(4) 0.6699(4) 0.09262(15) 0.0244(5) Uani 1 1 d . . .
H3 H -0.0376 0.7676 0.0508 0.037 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.393(4) . ?
C1 C2 1.396(4) . ?
C1 C7 1.514(4) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9500 . ?
C3 F1A 1.376(4) . ?
C3 C4 1.399(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C5 F1B 1.363(4) . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O3 1.424(3) . ?
C7 C8 1.518(3) . ?
C7 H7 1.0000 . ?
C8 O1 1.215(3) . ?
C8 O2 1.323(3) . ?
O2 H2A 0.8400 . ?
O3 H3 0.8400 . ?

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
C6 C1 C2 119.7(3) . . ?
C6 C1 C7 120.5(3) . . ?
C2 C1 C7 119.7(2) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 F1A 118.7(3) . . ?
C2 C3 C4 122.0(3) . . ?
F1A C3 C4 119.3(3) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
F1B C5 C4 120.7(3) . . ?
F1B C5 C6 117.2(3) . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O3 C7 C1 109.4(2) . . ?
O3 C7 C8 109.9(2) . . ?
C1 C7 C8 111.8(2) . . ?
O3 C7 H7 108.5 . . ?
C1 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
O1 C8 O2 124.7(2) . . ?
O1 C8 C7 123.0(2) . . ?
O2 C8 C7 112.3(2) . . ?
C8 O2 H2A 109.5 . . ?
C7 O3 H3 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
C6 C1 C2 C3 0.0(4) . . . . ?
C7 C1 C2 C3 -179.2(2) . . . . ?
C1 C2 C3 F1A 177.1(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
F1A C3 C4 C5 -177.2(3) . . . . ?
C3 C4 C5 F1B 176.3(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
F1B C5 C6 C1 -176.4(3) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C7 C1 C6 C5 179.3(2) . . . . ?
C6 C1 C7 O3 121.9(3) . . . . ?
C2 C1 C7 O3 -59.0(3) . . . . ?
C6 C1 C7 C8 -116.1(3) . . . . ?
C2 C1 C7 C8 63.0(3) . . . . ?
O3 C7 C8 O1 -2.3(4) . . . . ?
C1 C7 C8 O1 -124.0(3) . . . . ?
O3 C7 C8 O2 178.5(2) . . . . ?
C1 C7 C8 O2 56.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 1008570'
