# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_formI
_database_code_depnum_ccdc_archive 'CCDC 1026352'
_audit_update_record             
;
2014-10-07 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        p-cresol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H8 O'
_chemical_formula_weight         108.13

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/n

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

_cell_length_a                   5.6775(3)
_cell_length_b                   11.7141(7)
_cell_length_c                   18.3172(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.8320(10)
_cell_angle_gamma                90.00
_cell_volume                     1203.77(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2143
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      26.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8636
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.48
_reflns_number_total             2479
_reflns_number_gt                2143
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0561P)²+0.8939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2479
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1484
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
O9 O -0.0158(3) 0.48678(12) 0.60543(7) 0.0442(4) Uani 1 1 d . . .
H9 H -0.1280 0.4464 0.5710 0.053 Uiso 1 1 calc R . .
C13 C 0.4633(3) 0.25940(15) 0.72554(9) 0.0328(4) Uani 1 1 d . . .
C10 C 0.1389(3) 0.41015(15) 0.64520(9) 0.0322(4) Uani 1 1 d . . .
C3 C 0.5534(4) 0.73100(17) 0.50035(10) 0.0426(5) Uani 1 1 d . . .
H3 H 0.5877 0.6815 0.4623 0.051 Uiso 1 1 calc R . .
C14 C 0.5175(3) 0.37454(16) 0.71909(10) 0.0380(4) Uani 1 1 d . . .
H14 H 0.6677 0.4022 0.7424 0.046 Uiso 1 1 calc R . .
C12 C 0.2416(3) 0.22218(15) 0.69068(10) 0.0359(4) Uani 1 1 d . . .
H12 H 0.2001 0.1440 0.6943 0.043 Uiso 1 1 calc R . .
C5 C 0.6433(3) 0.90263(15) 0.57287(9) 0.0346(4) Uani 1 1 d . . .
C4 C 0.6883(3) 0.82805(17) 0.51786(10) 0.0407(4) Uani 1 1 d . . .
H4 H 0.8158 0.8442 0.4914 0.049 Uiso 1 1 calc R . .
C11 C 0.0792(3) 0.29619(15) 0.65079(10) 0.0354(4) Uani 1 1 d . . .
H11 H -0.0713 0.2689 0.6276 0.042 Uiso 1 1 calc R . .
C15 C 0.3582(3) 0.44965(16) 0.67963(10) 0.0379(4) Uani 1 1 d . . .
H15 H 0.3990 0.5279 0.6761 0.045 Uiso 1 1 calc R . .
C2 C 0.3693(3) 0.70666(17) 0.53847(10) 0.0414(5) Uani 1 1 d . . .
C6 C 0.4563(3) 0.87601(17) 0.61049(10) 0.0393(4) Uani 1 1 d . . .
H6 H 0.4213 0.9255 0.6485 0.047 Uiso 1 1 calc R . .
C7 C 0.3191(3) 0.77848(19) 0.59373(10) 0.0442(5) Uani 1 1 d . . .
H7 H 0.1919 0.7615 0.6201 0.053 Uiso 1 1 calc R . .
C16 C 0.6388(4) 0.17870(18) 0.76865(11) 0.0430(5) Uani 1 1 d . . .
H16A H 0.7836 0.2206 0.7889 0.065 Uiso 0.50 1 calc PR . .
H16B H 0.6792 0.1179 0.7359 0.065 Uiso 0.50 1 calc PR . .
H16C H 0.5677 0.1451 0.8092 0.065 Uiso 0.50 1 calc PR . .
H16D H 0.5701 0.1018 0.7671 0.065 Uiso 0.50 1 calc PR . .
H16E H 0.6745 0.2044 0.8201 0.065 Uiso 0.50 1 calc PR . .
H16F H 0.7859 0.1773 0.7468 0.065 Uiso 0.50 1 calc PR . .
C8 C 0.7922(4) 1.00840(18) 0.59045(12) 0.0523(6) Uani 1 1 d . . .
H8A H 0.9144 1.0121 0.5581 0.078 Uiso 0.50 1 calc PR . .
H8B H 0.8692 1.0058 0.6421 0.078 Uiso 0.50 1 calc PR . .
H8C H 0.6900 1.0761 0.5826 0.078 Uiso 0.50 1 calc PR . .
H8D H 0.7347 1.0505 0.6304 0.078 Uiso 0.50 1 calc PR . .
H8E H 0.7798 1.0569 0.5464 0.078 Uiso 0.50 1 calc PR . .
H8F H 0.9591 0.9866 0.6059 0.078 Uiso 0.50 1 calc PR . .
O1 O 0.2416(3) 0.60802(15) 0.51863(9) 0.0720(6) Uani 1 1 d . . .
H1 H 0.1088 0.6042 0.5444 0.086 Uiso 1 1 calc R . .


_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
O9 C10 1.383(2) . ?
O9 H9 0.9500 . ?
C13 C12 1.391(2) . ?
C13 C14 1.393(3) . ?
C13 C16 1.506(3) . ?
C10 C11 1.385(2) . ?
C10 C15 1.386(2) . ?
C3 C2 1.373(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C12 C11 1.389(3) . ?
C12 H12 0.9500 . ?
C5 C4 1.387(3) . ?
C5 C6 1.387(3) . ?
C5 C8 1.507(3) . ?
C4 H4 0.9500 . ?
C11 H11 0.9500 . ?
C15 H15 0.9500 . ?
C2 C7 1.379(3) . ?
C2 O1 1.383(2) . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C8 H8F 0.9800 . ?
O1 H1 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
C10 O9 H9 109.5 . . ?
C12 C13 C14 117.44(17) . . ?
C12 C13 C16 121.53(16) . . ?
C14 C13 C16 121.03(17) . . ?
O9 C10 C11 121.46(16) . . ?
O9 C10 C15 118.47(16) . . ?
C11 C10 C15 120.07(17) . . ?
C2 C3 C4 119.42(18) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C15 C14 C13 121.67(17) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C11 C12 C13 121.77(16) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C4 C5 C6 117.38(16) . . ?
C4 C5 C8 120.88(18) . . ?
C6 C5 C8 121.73(18) . . ?
C3 C4 C5 122.01(17) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C10 C11 C12 119.38(17) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C14 C15 C10 119.67(17) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C3 C2 C7 120.37(17) . . ?
C3 C2 O1 116.69(19) . . ?
C7 C2 O1 122.94(19) . . ?
C5 C6 C7 121.38(17) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C6 119.44(17) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C16 H16D 109.5 . . ?
H16A C16 H16D 141.1 . . ?
H16B C16 H16D 56.3 . . ?
H16C C16 H16D 56.3 . . ?
C13 C16 H16E 109.5 . . ?
H16A C16 H16E 56.3 . . ?
H16B C16 H16E 141.1 . . ?
H16C C16 H16E 56.3 . . ?
H16D C16 H16E 109.5 . . ?
C13 C16 H16F 109.5 . . ?
H16A C16 H16F 56.3 . . ?
H16B C16 H16F 56.3 . . ?
H16C C16 H16F 141.1 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C8 H8D 109.5 . . ?
H8A C8 H8D 141.1 . . ?
H8B C8 H8D 56.3 . . ?
H8C C8 H8D 56.3 . . ?
C5 C8 H8E 109.5 . . ?
H8A C8 H8E 56.3 . . ?
H8B C8 H8E 141.1 . . ?
H8C C8 H8E 56.3 . . ?
H8D C8 H8E 109.5 . . ?
C5 C8 H8F 109.5 . . ?
H8A C8 H8F 56.3 . . ?
H8B C8 H8F 56.3 . . ?
H8C C8 H8F 141.1 . . ?
H8D C8 H8F 109.5 . . ?
H8E C8 H8F 109.5 . . ?
C2 O1 H1 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
O9 H9 O1 0.95 1.79 2.673(2) 153.8 3_566
O1 H1 O9 0.95 1.97 2.719(2) 134.1 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.049
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_formII
_database_code_depnum_ccdc_archive 'CCDC 1026353'
_audit_update_record             
;
2014-10-07 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        p-cresol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H8 O'
_chemical_formula_weight         108.13

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   C2/c

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

_cell_length_a                   26.2548(16)
_cell_length_b                   6.0047(4)
_cell_length_c                   27.3511(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.786(2)
_cell_angle_gamma                90.00
_cell_volume                     3814.8(4)
_cell_formula_units_Z            24
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3201
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      26.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12863
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.49
_reflns_number_total             3933
_reflns_number_gt                3201
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0453P)²+1.8169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3933
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O9 O 0.71831(4) 0.56468(15) 0.60686(4) 0.0450(2) Uani 1 1 d . . .
H9 H 0.7023 0.4255 0.5891 0.076(5) Uiso 1 1 calc R . .
O17 O 0.75879(4) 0.87849(16) 0.56578(4) 0.0438(2) Uani 1 1 d . . .
H17 H 0.7480 0.7536 0.5802 0.053 Uiso 1 1 calc R . .
O1 O 0.68111(4) 0.19739(15) 0.54841(4) 0.0450(2) Uani 1 1 d . . .
H1 H 0.7054 0.0761 0.5508 0.054 Uiso 1 1 calc R . .
C15 C 0.66926(5) 0.4561(2) 0.65905(5) 0.0359(3) Uani 1 1 d . . .
H15 H 0.6586 0.3172 0.6403 0.043 Uiso 1 1 calc R . .
C10 C 0.70046(5) 0.6087(2) 0.64608(5) 0.0339(3) Uani 1 1 d . . .
C7 C 0.60975(5) -0.0600(2) 0.48599(5) 0.0367(3) Uani 1 1 d . . .
H7 H 0.6383 -0.1704 0.4930 0.044 Uiso 1 1 calc R . .
C12 C 0.69971(5) 0.8595(2) 0.71370(5) 0.0383(3) Uani 1 1 d . . .
H12 H 0.7103 0.9988 0.7323 0.046 Uiso 1 1 calc R . .
C2 C 0.62477(5) 0.1447(2) 0.51207(5) 0.0337(3) Uani 1 1 d . . .
C18 C 0.81750(5) 0.9113(2) 0.59560(5) 0.0349(3) Uani 1 1 d . . .
C13 C 0.66840(5) 0.7091(2) 0.72774(5) 0.0373(3) Uani 1 1 d . . .
C3 C 0.58312(5) 0.3045(2) 0.50189(5) 0.0386(3) Uani 1 1 d . . .
H3 H 0.5935 0.4447 0.5200 0.046 Uiso 1 1 calc R . .
C6 C 0.55236(5) -0.1016(2) 0.44939(5) 0.0399(3) Uani 1 1 d . . .
H6 H 0.5420 -0.2424 0.4316 0.048 Uiso 1 1 calc R . .
C23 C 0.83995(6) 1.1087(2) 0.58788(5) 0.0422(3) Uani 1 1 d . . .
H23 H 0.8152 1.2182 0.5631 0.051 Uiso 1 1 calc R . .
C14 C 0.65357(5) 0.5075(2) 0.69968(5) 0.0384(3) Uani 1 1 d . . .
H14 H 0.6321 0.4020 0.7085 0.046 Uiso 1 1 calc R . .
C5 C 0.50973(5) 0.0562(2) 0.43808(5) 0.0389(3) Uani 1 1 d . . .
C11 C 0.71585(5) 0.8115(2) 0.67337(5) 0.0377(3) Uani 1 1 d . . .
H11 H 0.7373 0.9167 0.6645 0.045 Uiso 1 1 calc R . .
C4 C 0.52621(5) 0.2591(2) 0.46515(5) 0.0399(3) Uani 1 1 d . . .
H4 H 0.4978 0.3696 0.4583 0.048 Uiso 1 1 calc R . .
C22 C 0.89860(6) 1.1454(2) 0.61650(5) 0.0468(3) Uani 1 1 d . . .
H22 H 0.9138 1.2814 0.6111 0.056 Uiso 1 1 calc R . .
C19 C 0.85345(6) 0.7533(2) 0.63166(5) 0.0427(3) Uani 1 1 d . . .
H18 H 0.8381 0.6179 0.6371 0.051 Uiso 1 1 calc R . .
C20 C 0.91228(6) 0.7933(3) 0.65997(6) 0.0493(3) Uani 1 1 d . . .
H19 H 0.9369 0.6837 0.6848 0.059 Uiso 1 1 calc R . .
C21 C 0.93585(6) 0.9892(3) 0.65283(5) 0.0473(3) Uani 1 1 d . . .
C8 C 0.44755(6) 0.0095(3) 0.39787(6) 0.0570(4) Uani 1 1 d . . .
H8A H 0.4241 0.1402 0.3954 0.086 Uiso 0.50 1 calc PR . .
H8B H 0.4341 -0.1188 0.4108 0.086 Uiso 0.50 1 calc PR . .
H8C H 0.4442 -0.0231 0.3614 0.086 Uiso 0.50 1 calc PR . .
H8D H 0.4441 -0.1413 0.3830 0.086 Uiso 0.50 1 calc PR . .
H8E H 0.4341 0.1176 0.3676 0.086 Uiso 0.50 1 calc PR . .
H8F H 0.4240 0.0219 0.4170 0.086 Uiso 0.50 1 calc PR . .
C16 C 0.65171(6) 0.7644(3) 0.77217(6) 0.0544(4) Uani 1 1 d . . .
H16A H 0.6659 0.9132 0.7869 0.082 Uiso 0.50 1 calc PR . .
H16B H 0.6687 0.6546 0.8020 0.082 Uiso 0.50 1 calc PR . .
H16C H 0.6097 0.7612 0.7565 0.082 Uiso 0.50 1 calc PR . .
H16D H 0.6303 0.6394 0.7767 0.082 Uiso 0.50 1 calc PR . .
H16E H 0.6275 0.8981 0.7616 0.082 Uiso 0.50 1 calc PR . .
H16F H 0.6865 0.7915 0.8071 0.082 Uiso 0.50 1 calc PR . .
C24 C 1.00004(7) 1.0297(4) 0.68203(7) 0.0734(5) Uani 1 1 d . . .
H24A H 1.0082 1.1767 0.6718 0.110 Uiso 0.50 1 calc PR . .
H24B H 1.0193 0.9150 0.6711 0.110 Uiso 0.50 1 calc PR . .
H24C H 1.0142 1.0236 0.7221 0.110 Uiso 0.50 1 calc PR . .
H24D H 1.0196 0.9001 0.7049 0.110 Uiso 0.50 1 calc PR . .
H24E H 1.0085 1.1619 0.7056 0.110 Uiso 0.50 1 calc PR . .
H24F H 1.0136 1.0533 0.6546 0.110 Uiso 0.50 1 calc PR . .


_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
O9 C10 1.3818(14) . ?
O9 H9 0.9600 . ?
O17 C18 1.3813(14) . ?
O17 H17 0.9500 . ?
O1 C2 1.3804(14) . ?
O1 H1 0.9500 . ?
C15 C10 1.3811(16) . ?
C15 C14 1.3881(17) . ?
C15 H15 0.9500 . ?
C10 C11 1.3867(17) . ?
C7 C2 1.3832(17) . ?
C7 C6 1.3887(17) . ?
C7 H7 0.9500 . ?
C12 C11 1.3839(17) . ?
C12 C13 1.3903(18) . ?
C12 H12 0.9500 . ?
C2 C3 1.3818(17) . ?
C18 C19 1.3767(18) . ?
C18 C23 1.3830(18) . ?
C13 C14 1.3886(18) . ?
C13 C16 1.5084(18) . ?
C3 C4 1.3844(17) . ?
C3 H3 0.9500 . ?
C6 C5 1.3871(19) . ?
C6 H6 0.9500 . ?
C23 C22 1.3817(18) . ?
C23 H23 0.9500 . ?
C14 H14 0.9500 . ?
C5 C4 1.3859(19) . ?
C5 C8 1.5097(18) . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C22 C21 1.385(2) . ?
C22 H22 0.9500 . ?
C19 C20 1.3884(19) . ?
C19 H18 0.9500 . ?
C20 C21 1.385(2) . ?
C20 H19 0.9500 . ?
C21 C24 1.511(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C8 H8F 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 H24D 0.9800 . ?
C24 H24E 0.9800 . ?
C24 H24F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O9 H9 109.5 . . ?
C18 O17 H17 109.5 . . ?
C2 O1 H1 109.5 . . ?
C10 C15 C14 119.41(11) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C10 O9 121.94(11) . . ?
C15 C10 C11 120.23(11) . . ?
O9 C10 C11 117.81(10) . . ?
C2 C7 C6 118.98(11) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C11 C12 C13 121.67(11) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
O1 C2 C3 117.90(11) . . ?
O1 C2 C7 121.81(11) . . ?
C3 C2 C7 120.30(11) . . ?
C19 C18 O17 121.90(11) . . ?
C19 C18 C23 120.08(12) . . ?
O17 C18 C23 118.02(11) . . ?
C14 C13 C12 117.62(11) . . ?
C14 C13 C16 121.66(12) . . ?
C12 C13 C16 120.72(12) . . ?
C2 C3 C4 119.63(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C6 C7 121.95(12) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C22 C23 C18 119.47(12) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
C15 C14 C13 121.65(11) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C4 C5 C6 117.57(11) . . ?
C4 C5 C8 120.98(13) . . ?
C6 C5 C8 121.45(13) . . ?
C12 C11 C10 119.42(11) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C3 C4 C5 121.56(12) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C23 C22 C21 121.75(13) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C18 C19 C20 119.57(12) . . ?
C18 C19 H18 120.2 . . ?
C20 C19 H18 120.2 . . ?
C21 C20 C19 121.47(13) . . ?
C21 C20 H19 119.3 . . ?
C19 C20 H19 119.3 . . ?
C22 C21 C20 117.65(12) . . ?
C22 C21 C24 120.73(14) . . ?
C20 C21 C24 121.59(14) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C8 H8D 109.5 . . ?
H8A C8 H8D 141.1 . . ?
H8B C8 H8D 56.3 . . ?
H8C C8 H8D 56.3 . . ?
C5 C8 H8E 109.5 . . ?
H8A C8 H8E 56.3 . . ?
H8B C8 H8E 141.1 . . ?
H8C C8 H8E 56.3 . . ?
H8D C8 H8E 109.5 . . ?
C5 C8 H8F 109.5 . . ?
H8A C8 H8F 56.3 . . ?
H8B C8 H8F 56.3 . . ?
H8C C8 H8F 141.1 . . ?
H8D C8 H8F 109.5 . . ?
H8E C8 H8F 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C16 H16D 109.5 . . ?
H16A C16 H16D 141.1 . . ?
H16B C16 H16D 56.3 . . ?
H16C C16 H16D 56.3 . . ?
C13 C16 H16E 109.5 . . ?
H16A C16 H16E 56.3 . . ?
H16B C16 H16E 141.1 . . ?
H16C C16 H16E 56.3 . . ?
H16D C16 H16E 109.5 . . ?
C13 C16 H16F 109.5 . . ?
H16A C16 H16F 56.3 . . ?
H16B C16 H16F 56.3 . . ?
H16C C16 H16F 141.1 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C24 H24D 109.5 . . ?
H24A C24 H24D 141.1 . . ?
H24B C24 H24D 56.3 . . ?
H24C C24 H24D 56.3 . . ?
C21 C24 H24E 109.5 . . ?
H24A C24 H24E 56.3 . . ?
H24B C24 H24E 141.1 . . ?
H24C C24 H24E 56.3 . . ?
H24D C24 H24E 109.5 . . ?
C21 C24 H24F 109.5 . . ?
H24A C24 H24F 56.3 . . ?
H24B C24 H24F 56.3 . . ?
H24C C24 H24F 141.1 . . ?
H24D C24 H24F 109.5 . . ?
H24E C24 H24F 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
O17 H17 O9 0.95 1.72 2.6563(12) 168.2 .
O1 H1 O17 0.95 1.73 2.6737(13) 169.7 1_545
O9 H9 O1 0.96 1.69 2.6302(12) 166.7 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.030
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
