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

#######################################################################
#
#                 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_dimetanol

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 trans-1,4-cyclohexanedimethanol 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 O2'
_chemical_formula_weight         144.21

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   P21/c

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                   10.6792(15)
_cell_length_b                   9.1741(14)
_cell_length_c                   9.0549(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.211(3)
_cell_angle_gamma                90.00
_cell_volume                     873.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    704
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_reflns_number            5023
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.71
_reflns_number_total             2257
_reflns_number_gt                1093
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_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. 
;

_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)+(0.0677P)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         2257
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1573
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 0.10461(15) 0.5186(2) 0.13055(16) 0.0431(5) Uani 1 1 d . . .
H1A H 0.1753 0.5361 0.0770 0.052 Uiso 1 1 calc R . .
C2 C 0.04858(19) 0.3699(2) 0.08335(18) 0.0542(5) Uani 1 1 d . . .
H2A H -0.0185 0.3480 0.1395 0.065 Uiso 1 1 calc R . .
H2B H 0.1142 0.2963 0.1075 0.065 Uiso 1 1 calc R . .
C3 C 0.00544(18) 0.6363(2) 0.08411(18) 0.0509(5) Uani 1 1 d . . .
H3A H 0.0437 0.7311 0.1085 0.061 Uiso 1 1 calc R . .
H3B H -0.0632 0.6244 0.1403 0.061 Uiso 1 1 calc R . .
C4 C 0.15751(19) 0.5215(2) 0.29734(18) 0.0580(6) Uani 1 1 d . . .
H4A H 0.0884 0.5158 0.3536 0.070 Uiso 1 1 calc R . .
H4B H 0.2129 0.4382 0.3241 0.070 Uiso 1 1 calc R . .
O1 O 0.22653(14) 0.65180(17) 0.33352(13) 0.0695(5) Uani 1 1 d . . .
H1 H 0.248(2) 0.656(3) 0.422(3) 0.104 Uiso 1 1 d . . .
O2 O 0.30662(15) 0.65386(17) 0.63633(13) 0.0649(5) Uani 1 1 d . . .
H2 H 0.285(2) 0.714(3) 0.688(3) 0.097 Uiso 1 1 d . . .
C5 C 0.39643(15) 0.5307(2) 0.87267(16) 0.0431(5) Uani 1 1 d . . .
H5 H 0.3425 0.5906 0.9255 0.052 Uiso 1 1 calc R . .
C6 C 0.52376(16) 0.6055(2) 0.88788(18) 0.0529(5) Uani 1 1 d . . .
H6A H 0.5119 0.7024 0.8447 0.063 Uiso 1 1 calc R . .
H6B H 0.5778 0.5512 0.8320 0.063 Uiso 1 1 calc R . .
C7 C 0.41072(18) 0.3825(2) 0.9492(2) 0.0565(6) Uani 1 1 d . . .
H7A H 0.3273 0.3392 0.9448 0.068 Uiso 1 1 calc R . .
H7B H 0.4599 0.3189 0.8958 0.068 Uiso 1 1 calc R . .
C8 C 0.32928(19) 0.5173(2) 0.71060(18) 0.0612(6) Uani 1 1 d . . .
H8A H 0.3806 0.4573 0.6562 0.073 Uiso 1 1 calc R . .
H8B H 0.2486 0.4681 0.7083 0.073 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0486(10) 0.0493(12) 0.0292(7) -0.0014(7) 0.0004(7) -0.0067(9)
C2 0.0680(12) 0.0444(12) 0.0433(9) 0.0013(8) -0.0086(9) 0.0006(10)
C3 0.0621(11) 0.0468(12) 0.0397(8) -0.0099(8) -0.0022(8) -0.0030(10)
C4 0.0731(12) 0.0595(14) 0.0349(9) 0.0042(9) -0.0082(8) -0.0155(11)
O1 0.0992(11) 0.0700(11) 0.0304(6) 0.0030(7) -0.0128(7) -0.0344(9)
O2 0.0919(11) 0.0659(11) 0.0297(6) 0.0027(6) -0.0086(6) 0.0215(9)
C5 0.0488(10) 0.0466(12) 0.0308(7) 0.0035(7) -0.0010(7) 0.0044(9)
C6 0.0585(11) 0.0545(13) 0.0425(9) 0.0151(9) 0.0004(8) 0.0002(10)
C7 0.0618(11) 0.0525(14) 0.0488(10) 0.0080(9) -0.0073(9) -0.0071(10)
C8 0.0759(13) 0.0591(15) 0.0410(9) -0.0006(10) -0.0106(9) 0.0067(11)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.516(2) . ?
C1 C3 1.519(2) . ?
C1 C2 1.520(2) . ?
C1 H1A 0.9800 . ?
C2 C3 1.525(2) 3_565 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C2 1.525(2) 3_565 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O1 1.412(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O1 H1 0.79(3) . ?
O2 C8 1.422(2) . ?
O2 H2 0.78(3) . ?
C5 C6 1.507(2) . ?
C5 C8 1.520(2) . ?
C5 C7 1.521(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.521(2) 3_667 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C6 1.521(2) 3_667 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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 C1 C3 112.45(14) . . ?
C4 C1 C2 110.77(14) . . ?
C3 C1 C2 109.85(14) . . ?
C4 C1 H1A 107.9 . . ?
C3 C1 H1A 107.9 . . ?
C2 C1 H1A 107.9 . . ?
C1 C2 C3 111.95(15) . 3_565 ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 3_565 . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 3_565 . ?
H2A C2 H2B 107.9 . . ?
C1 C3 C2 111.79(14) . 3_565 ?
C1 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 3_565 . ?
C1 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 3_565 . ?
H3A C3 H3B 107.9 . . ?
O1 C4 C1 109.45(14) . . ?
O1 C4 H4A 109.8 . . ?
C1 C4 H4A 109.8 . . ?
O1 C4 H4B 109.8 . . ?
C1 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C4 O1 H1 108(2) . . ?
C8 O2 H2 112.2(18) . . ?
C6 C5 C8 112.87(14) . . ?
C6 C5 C7 110.44(14) . . ?
C8 C5 C7 111.07(15) . . ?
C6 C5 H5 107.4 . . ?
C8 C5 H5 107.4 . . ?
C7 C5 H5 107.4 . . ?
C5 C6 C7 111.96(14) . 3_667 ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 3_667 . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 3_667 . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C5 111.65(16) 3_667 . ?
C6 C7 H7A 109.3 3_667 . ?
C5 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 3_667 . ?
C5 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O2 C8 C5 113.38(15) . . ?
O2 C8 H8A 108.9 . . ?
C5 C8 H8A 108.9 . . ?
O2 C8 H8B 108.9 . . ?
C5 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 989757'
#######################################################################
#
#                 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_t14revised2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 trans-1,4-cyclohexanedimethanol 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 O2'
_chemical_formula_weight         144.21

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

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

_cell_length_a                   5.1064(4)
_cell_length_b                   5.1749(4)
_cell_length_c                   16.3054(10)
_cell_angle_alpha                88.250(5)
_cell_angle_beta                 81.485(5)
_cell_angle_gamma                79.662(5)
_cell_volume                     419.20(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    470
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      24.53

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             160
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.445
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_reflns_number            3603
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0498
_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       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.79
_diffrn_reflns_theta_max         25.84
_reflns_number_total             1594
_reflns_number_gt                765
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_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. 
;

_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)+(0.1353P)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         1594
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.2336
_refine_ls_wR_factor_gt          0.1756
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0542(4) 0.1862(5) 0.72366(12) 0.0697(8) Uani 1 1 d . . .
H1 H -0.091(7) 0.252(6) 0.7348(19) 0.084 Uiso 1 1 d . . .
C1 C 0.1029(5) -0.0347(5) 0.67122(15) 0.0502(8) Uani 1 1 d . . .
H1A H -0.0297 -0.1447 0.6897 0.060 Uiso 1 1 calc R . .
H1B H 0.2787 -0.1361 0.6767 0.060 Uiso 1 1 calc R . .
C2 C 0.0930(4) 0.0326(4) 0.58069(13) 0.0357(7) Uani 1 1 d . . .
H2A H 0.2127 0.1594 0.5644 0.043 Uiso 1 1 calc R . .
C3 C 0.1961(4) -0.2122(4) 0.52743(14) 0.0419(7) Uani 1 1 d . . .
H3A H 0.3797 -0.2824 0.5356 0.050 Uiso 1 1 calc R . .
H3B H 0.0873 -0.3447 0.5454 0.050 Uiso 1 1 calc R . .
C4 C -0.1879(4) 0.1562(5) 0.56388(14) 0.0414(7) Uani 1 1 d . . .
H4A H -0.3121 0.0386 0.5834 0.050 Uiso 1 1 calc R . .
H4B H -0.2463 0.3190 0.5946 0.050 Uiso 1 1 calc R . .
O2 O 0.5036(4) 0.3403(5) 0.77196(12) 0.0716(9) Uani 1 1 d . . .
H2 H 0.385(7) 0.286(6) 0.7606(18) 0.086 Uiso 1 1 d . . .
C5 C 0.4155(5) 0.5537(5) 0.82760(14) 0.0528(8) Uani 1 1 d . . .
H5A H 0.2347 0.6360 0.8198 0.063 Uiso 1 1 calc R . .
H5B H 0.5314 0.6830 0.8142 0.063 Uiso 1 1 calc R . .
C6 C 0.4155(4) 0.4756(4) 0.91723(13) 0.0364(7) Uani 1 1 d . . .
H6 H 0.2972 0.3457 0.9300 0.044 Uiso 1 1 calc R . .
C7 C 0.3033(4) 0.7120(4) 0.97300(14) 0.0426(7) Uani 1 1 d . . .
H7A H 0.4088 0.8489 0.9576 0.051 Uiso 1 1 calc R . .
H7B H 0.1200 0.7797 0.9639 0.051 Uiso 1 1 calc R . .
C8 C 0.6949(4) 0.3514(5) 0.93563(14) 0.0424(7) Uani 1 1 d . . .
H8A H 0.7568 0.1912 0.9037 0.051 Uiso 1 1 calc R . .
H8B H 0.8190 0.4709 0.9183 0.051 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0490(12) 0.109(2) 0.0508(14) -0.0372(12) -0.0118(10) -0.0046(12)
C1 0.0462(15) 0.070(2) 0.0348(16) -0.0041(14) -0.0143(11) -0.0032(14)
C2 0.0334(13) 0.0435(15) 0.0318(14) -0.0014(11) -0.0092(10) -0.0073(11)
C3 0.0383(14) 0.0442(16) 0.0424(17) -0.0035(12) -0.0151(11) 0.0028(12)
C4 0.0366(13) 0.0485(16) 0.0375(15) -0.0105(12) -0.0074(10) -0.0003(12)
O2 0.0468(12) 0.121(2) 0.0469(14) -0.0371(13) -0.0112(10) -0.0048(12)
C5 0.0514(16) 0.076(2) 0.0320(16) -0.0064(14) -0.0124(12) -0.0089(15)
C6 0.0328(13) 0.0438(15) 0.0336(15) -0.0051(11) -0.0076(10) -0.0062(11)
C7 0.0386(14) 0.0471(16) 0.0417(17) -0.0046(12) -0.0164(11) 0.0027(12)
C8 0.0339(13) 0.0544(17) 0.0368(15) -0.0130(12) -0.0086(10) 0.0024(12)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.412(3) . ?
O1 H1 0.76(3) . ?
C1 C2 1.512(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.523(3) . ?
C2 C3 1.526(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.513(3) 2_556 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C3 1.513(3) 2_556 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O2 C5 1.417(3) . ?
O2 H2 0.76(3) . ?
C5 C6 1.504(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.521(3) . ?
C6 C8 1.525(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.517(3) 2_667 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C7 1.517(3) 2_667 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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
C1 O1 H1 116(2) . . ?
O1 C1 C2 114.1(2) . . ?
O1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
O1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C4 112.69(19) . . ?
C1 C2 C3 110.2(2) . . ?
C4 C2 C3 109.74(17) . . ?
C1 C2 H2A 108.0 . . ?
C4 C2 H2A 108.0 . . ?
C3 C2 H2A 108.0 . . ?
C4 C3 C2 112.41(19) 2_556 . ?
C4 C3 H3A 109.1 2_556 . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 2_556 . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C2 111.91(18) 2_556 . ?
C3 C4 H4A 109.2 2_556 . ?
C2 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 2_556 . ?
C2 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C5 O2 H2 111(2) . . ?
O2 C5 C6 113.6(2) . . ?
O2 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
O2 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 110.4(2) . . ?
C5 C6 C8 112.32(19) . . ?
C7 C6 C8 109.97(17) . . ?
C5 C6 H6 108.0 . . ?
C7 C6 H6 108.0 . . ?
C8 C6 H6 108.0 . . ?
C8 C7 C6 113.1(2) 2_667 . ?
C8 C7 H7A 109.0 2_667 . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 2_667 . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C6 112.07(18) 2_667 . ?
C7 C8 H8A 109.2 2_667 . ?
C6 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 2_667 . ?
C6 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 1016822'
