# 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_compound_1

_database_code_depnum_ccdc_archive 'CCDC 687452'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_chemical_absolute_configuration RM

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   P2(1)

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

_cell_length_a                   7.87590(10)
_cell_length_b                   5.78340(10)
_cell_length_c                   13.3230(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8770(10)
_cell_angle_gamma                90.00
_cell_volume                     605.467(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1989
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      31.59

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3132
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1939
_reflns_number_gt                1825
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0509P)²+0.0515P] 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     SHELXL
_refine_ls_extinction_coef       0.059(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(12)
_refine_ls_number_reflns         1939
_refine_ls_number_parameters     159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 -0.2050(2) -0.2385(4) -0.07161(11) 0.0495(4) Uani 1 1 d . . .
C2 C -0.36192(19) -0.1769(3) -0.13801(11) 0.0466(4) Uani 1 1 d . . .
H2A H -0.4380 -0.3112 -0.1413 0.056 Uiso 1 1 calc R . .
C3 C -0.4577(3) 0.0268(4) -0.09561(14) 0.0684(5) Uani 1 1 d . . .
H3A H -0.4902 -0.0109 -0.0294 0.103 Uiso 1 1 calc R . .
H3B H -0.5577 0.0588 -0.1386 0.103 Uiso 1 1 calc R . .
H3C H -0.3854 0.1606 -0.0921 0.103 Uiso 1 1 calc R . .
C4 C -0.30599(17) -0.1300(3) -0.24369(11) 0.0406(4) Uani 1 1 d . . .
C5 C -0.21402(19) 0.0718(3) -0.26462(11) 0.0463(4) Uani 1 1 d . . .
H5A H -0.1826 0.1737 -0.2127 0.056 Uiso 1 1 calc R . .
C6 C -0.17043(18) 0.1200(3) -0.35983(11) 0.0453(4) Uani 1 1 d . . .
H6A H -0.1093 0.2537 -0.3716 0.054 Uiso 1 1 calc R . .
C7 C -0.21688(16) -0.0304(3) -0.44072(11) 0.0385(4) Uani 1 1 d . . .
C8 C -0.18465(18) 0.0252(3) -0.54200(11) 0.0443(4) Uani 1 1 d . . .
H8A H -0.1255 0.1591 -0.5562 0.053 Uiso 1 1 calc R . .
C9 C -0.24134(18) -0.1198(3) -0.61800(11) 0.0468(4) Uani 1 1 d . . .
C10 C -0.32462(19) -0.3285(4) -0.59655(12) 0.0498(4) Uani 1 1 d . . .
H10A H -0.3600 -0.4274 -0.6489 0.060 Uiso 1 1 calc R . .
C11 C -0.35373(18) -0.3866(3) -0.50055(11) 0.0455(4) Uani 1 1 d . . .
H11A H -0.4070 -0.5260 -0.4877 0.055 Uiso 1 1 calc R . .
C12 C -0.30390(17) -0.2373(3) -0.41969(11) 0.0379(3) Uani 1 1 d . . .
C13 C -0.34704(17) -0.2826(3) -0.32007(11) 0.0397(4) Uani 1 1 d . . .
H13A H -0.4043 -0.4184 -0.3063 0.048 Uiso 1 1 calc R . .
C14 C -0.1459(3) 0.1247(5) -0.74714(13) 0.0725(6) Uani 1 1 d . . .
H14A H -0.1433 0.1293 -0.8191 0.109 Uiso 1 1 calc R . .
H14B H -0.0318 0.1300 -0.7171 0.109 Uiso 1 1 calc R . .
H14C H -0.2088 0.2551 -0.7249 0.109 Uiso 1 1 calc R . .
O1 O -0.1205(2) -0.0963(3) -0.02514(13) 0.0901(5) Uani 1 1 d . . .
O2 O -0.17103(18) -0.4597(3) -0.07226(10) 0.0656(4) Uani 1 1 d . . .
O3 O -0.22567(16) -0.0827(3) -0.71829(8) 0.0638(4) Uani 1 1 d . . .
H2 H -0.081(4) -0.497(5) -0.0362(18) 0.101(9) Uiso 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
C1 O1 1.203(2) . ?
C1 O2 1.307(2) . ?
C1 C2 1.513(2) . ?
C2 C3 1.528(3) . ?
C2 C4 1.528(2) . ?
C2 H2A 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C13 1.369(2) . ?
C4 C5 1.412(2) . ?
C5 C6 1.365(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.414(2) . ?
C6 H6A 0.9300 . ?
C7 C12 1.417(2) . ?
C7 C8 1.426(2) . ?
C8 C9 1.366(2) . ?
C8 H8A 0.9300 . ?
C9 O3 1.3671(19) . ?
C9 C10 1.412(3) . ?
C10 C11 1.357(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.415(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.417(2) . ?
C13 H13A 0.9300 . ?
C14 O3 1.419(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O2 H2 0.86(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
O1 C1 O2 124.49(18) . . ?
O1 C1 C2 122.8(2) . . ?
O2 C1 C2 112.71(15) . . ?
C1 C2 C3 111.70(15) . . ?
C1 C2 C4 107.79(12) . . ?
C3 C2 C4 112.61(15) . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2A 108.2 . . ?
C4 C2 H2A 108.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C13 C4 C5 119.00(14) . . ?
C13 C4 C2 120.16(15) . . ?
C5 C4 C2 120.83(14) . . ?
C6 C5 C4 121.13(14) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C7 120.97(15) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C12 118.21(13) . . ?
C6 C7 C8 121.96(14) . . ?
C12 C7 C8 119.79(13) . . ?
C9 C8 C7 119.52(16) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 O3 125.54(17) . . ?
C8 C9 C10 120.50(14) . . ?
O3 C9 C10 113.96(15) . . ?
C11 C10 C9 120.85(15) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C12 120.72(17) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C11 C12 C7 118.54(13) . . ?
C11 C12 C13 121.92(14) . . ?
C7 C12 C13 119.44(13) . . ?
C4 C13 C12 121.17(14) . . ?
C4 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 O2 H2 114(2) . . ?
C9 O3 C14 117.94(15) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.026
####################################################################### 
# 
# 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_compound_2

_database_code_depnum_ccdc_archive 'CCDC 687453'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.28
_chemical_absolute_configuration RM

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   P2(1)2(1)2(1)

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'

_cell_length_a                   5.89120(10)
_cell_length_b                   7.9258(2)
_cell_length_c                   28.6878(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1339.50(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2630
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      23.99

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7218
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         27.44
_reflns_number_total             2999
_reflns_number_gt                2232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)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     SHELXL
_refine_ls_extinction_coef       0.010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(18)
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 -0.7816(3) -0.06767(19) 0.09103(5) 0.0714(4) Uani 1 1 d . . .
O2 O -0.7481(4) 0.4282(2) -0.17584(5) 0.0913(6) Uani 1 1 d . . .
O3 O -0.5808(6) 0.2374(3) -0.21732(10) 0.1857(16) Uani 1 1 d . . .
C1 C -0.6851(3) -0.0694(2) 0.00872(7) 0.0550(4) Uani 1 1 d . . .
H1A H -0.5529 -0.1309 0.0137 0.066 Uiso 1 1 calc R . .
C2 C -0.8241(3) -0.0297(2) 0.04535(6) 0.0548(4) Uani 1 1 d . . .
C3 C -1.0296(3) 0.0581(2) 0.03777(7) 0.0589(5) Uani 1 1 d . . .
H3A H -1.1243 0.0822 0.0628 0.071 Uiso 1 1 calc R . .
C4 C -1.0897(3) 0.1075(2) -0.00575(7) 0.0571(5) Uani 1 1 d . . .
H4A H -1.2259 0.1646 -0.0102 0.069 Uiso 1 1 calc R . .
C5 C -0.9493(3) 0.0736(2) -0.04428(6) 0.0508(4) Uani 1 1 d . . .
C6 C -1.0020(3) 0.1307(2) -0.08980(7) 0.0580(5) Uani 1 1 d . . .
H6A H -1.1354 0.1909 -0.0947 0.070 Uiso 1 1 calc R . .
C7 C -0.8614(4) 0.0993(3) -0.12677(7) 0.0636(5) Uani 1 1 d . . .
C8 C -0.6594(4) 0.0079(3) -0.11895(8) 0.0681(5) Uani 1 1 d . . .
H8A H -0.5629 -0.0144 -0.1439 0.082 Uiso 1 1 calc R . .
C9 C -0.6033(3) -0.0479(3) -0.07577(7) 0.0619(5) Uani 1 1 d . . .
H9A H -0.4695 -0.1085 -0.0717 0.074 Uiso 1 1 calc R . .
C10 C -0.7442(3) -0.0161(2) -0.03676(6) 0.0522(4) Uani 1 1 d . . .
C11 C -0.5745(4) -0.1497(3) 0.10205(8) 0.0789(6) Uani 1 1 d . . .
H11A H -0.5666 -0.1688 0.1351 0.118 Uiso 1 1 calc R . .
H11B H -0.4494 -0.0800 0.0926 0.118 Uiso 1 1 calc R . .
H11C H -0.5672 -0.2558 0.0860 0.118 Uiso 1 1 calc R . .
C12 C -0.9204(5) 0.1624(3) -0.17532(7) 0.0809(7) Uani 1 1 d . . .
H12A H -1.0610 0.2282 -0.1735 0.097 Uiso 1 1 calc R . .
C13 C -0.9569(9) 0.0153(4) -0.20988(9) 0.1312(14) Uani 1 1 d . . .
H13A H -0.9937 0.0598 -0.2401 0.197 Uiso 1 1 calc R . .
H13B H -1.0792 -0.0546 -0.1991 0.197 Uiso 1 1 calc R . .
H13C H -0.8206 -0.0506 -0.2119 0.197 Uiso 1 1 calc R . .
C14 C -0.7318(5) 0.2770(3) -0.19242(8) 0.0874(8) Uani 1 1 d . . .
C15 C -0.5724(7) 0.5475(4) -0.18870(10) 0.1130(10) Uani 1 1 d . . .
H15A H -0.6029 0.6545 -0.1743 0.169 Uiso 1 1 calc R . .
H15B H -0.5702 0.5607 -0.2220 0.169 Uiso 1 1 calc R . .
H15C H -0.4277 0.5063 -0.1783 0.169 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
O1 C2 1.368(2) . ?
O1 C11 1.418(3) . ?
O2 C14 1.293(3) . ?
O2 C15 1.450(4) . ?
O3 C14 1.183(3) . ?
C1 C2 1.369(3) . ?
C1 C10 1.414(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.414(3) . ?
C3 C4 1.355(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.406(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.417(3) . ?
C5 C10 1.419(2) . ?
C6 C7 1.369(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.411(3) . ?
C7 C12 1.520(3) . ?
C8 C9 1.356(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.416(3) . ?
C9 H9A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.517(4) . ?
C12 C13 1.545(4) . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C11 118.15(17) . . ?
C14 O2 C15 117.3(2) . . ?
C2 C1 C10 119.52(17) . . ?
C2 C1 H1A 120.2 . . ?
C10 C1 H1A 120.2 . . ?
O1 C2 C1 125.15(18) . . ?
O1 C2 C3 114.37(17) . . ?
C1 C2 C3 120.48(18) . . ?
C4 C3 C2 120.49(17) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 121.03(17) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 122.32(16) . . ?
C4 C5 C10 118.49(16) . . ?
C6 C5 C10 119.15(16) . . ?
C7 C6 C5 121.58(17) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C8 118.72(18) . . ?
C6 C7 C12 120.80(19) . . ?
C8 C7 C12 120.5(2) . . ?
C9 C8 C7 121.20(18) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C8 C9 C10 121.41(18) . . ?
C8 C9 H9A 119.3 . . ?
C10 C9 H9A 119.3 . . ?
C1 C10 C9 122.13(17) . . ?
C1 C10 C5 119.94(16) . . ?
C9 C10 C5 117.92(17) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C7 109.0(2) . . ?
C14 C12 C13 110.3(2) . . ?
C7 C12 C13 111.8(2) . . ?
C14 C12 H12A 108.6 . . ?
C7 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O2 121.6(3) . . ?
O3 C14 C12 126.0(3) . . ?
O2 C14 C12 112.4(2) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.025
####################################################################### 
# 
# 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_compound_3

_database_code_depnum_ccdc_archive 'CCDC 687454'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_chemical_absolute_configuration RM

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   P2(1)

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

_cell_length_a                   8.1459(9)
_cell_length_b                   5.8321(6)
_cell_length_c                   15.3640(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.919(5)
_cell_angle_gamma                90.00
_cell_volume                     711.43(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    873
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      21.04

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3275
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2196
_reflns_number_gt                1387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0831P)²+0.0774P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2196
_refine_ls_number_parameters     173
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 -0.2616(3) -0.4992(5) -0.67759(16) 0.0855(8) Uani 1 1 d . . .
O2 O -0.2433(5) -0.6619(8) -0.0770(3) 0.1533(17) Uani 1 1 d . . .
O3 O -0.4878(5) -0.5198(9) -0.1371(3) 0.1541(17) Uani 1 1 d . . .
C1 C -0.1906(4) -0.5875(6) -0.5183(2) 0.0699(10) Uani 1 1 d . . .
H1A H -0.1337 -0.7211 -0.5266 0.084 Uiso 1 1 calc R . .
C2 C -0.2600(4) -0.4547(6) -0.5896(2) 0.0670(10) Uani 1 1 d . . .
C3 C -0.3438(4) -0.2462(7) -0.5770(3) 0.0711(10) Uani 1 1 d . . .
H3A H -0.3901 -0.1544 -0.6258 0.085 Uiso 1 1 calc R . .
C4 C -0.3557(4) -0.1826(6) -0.4940(2) 0.0665(9) Uani 1 1 d . . .
H4A H -0.4091 -0.0455 -0.4864 0.080 Uiso 1 1 calc R . .
C5 C -0.2892(4) -0.3187(6) -0.4190(2) 0.0620(9) Uani 1 1 d . . .
C6 C -0.3070(4) -0.2602(7) -0.3326(2) 0.0661(9) Uani 1 1 d . . .
H6A H -0.3631 -0.1258 -0.3245 0.079 Uiso 1 1 calc R . .
C7 C -0.2434(4) -0.3970(6) -0.2602(2) 0.0706(10) Uani 1 1 d . . .
C8 C -0.1594(5) -0.5981(7) -0.2746(2) 0.0773(11) Uani 1 1 d . . .
H8A H -0.1157 -0.6924 -0.2261 0.093 Uiso 1 1 calc R . .
C9 C -0.1396(4) -0.6597(6) -0.3562(2) 0.0750(10) Uani 1 1 d . . .
H9A H -0.0820 -0.7942 -0.3625 0.090 Uiso 1 1 calc R . .
C10 C -0.2045(4) -0.5240(6) -0.4321(2) 0.0615(9) Uani 1 1 d . . .
C11 C -0.1864(5) -0.7079(8) -0.6972(3) 0.0974(13) Uani 1 1 d . . .
H11A H -0.1952 -0.7191 -0.7604 0.146 Uiso 1 1 calc R . .
H11B H -0.2434 -0.8353 -0.6776 0.146 Uiso 1 1 calc R . .
H11C H -0.0698 -0.7100 -0.6668 0.146 Uiso 1 1 calc R . .
C12 C -0.2577(5) -0.3238(8) -0.1672(2) 0.0860(12) Uani 1 1 d . . .
H12A H -0.3378 -0.1963 -0.1732 0.103 Uiso 1 1 calc R . .
C13 C -0.3253(7) -0.5192(11) -0.1221(3) 0.1012(14) Uani 1 1 d . . .
C14 C -0.0886(6) -0.2430(11) -0.1103(3) 0.1158(17) Uani 1 1 d . . .
H14A H -0.0485 -0.1149 -0.1388 0.174 Uiso 1 1 calc R . .
H14B H -0.0084 -0.3658 -0.1040 0.174 Uiso 1 1 calc R . .
H14C H -0.1030 -0.1977 -0.0524 0.174 Uiso 1 1 calc R . .
C15 C -0.5618(10) -0.721(2) -0.1003(6) 0.245(6) Uani 1 1 d D . .
H15A H -0.5266 -0.8593 -0.1259 0.294 Uiso 1 1 calc R . .
H15B H -0.5167 -0.7268 -0.0363 0.294 Uiso 1 1 calc R . .
C16 C -0.7156(10) -0.7190(19) -0.1143(5) 0.204(4) Uani 1 1 d D . .
H16A H -0.7539 -0.8559 -0.0902 0.306 Uiso 1 1 calc R . .
H16B H -0.7619 -0.7126 -0.1774 0.306 Uiso 1 1 calc R . .
H16C H -0.7518 -0.5873 -0.0861 0.306 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
O1 C2 1.373(4) . ?
O1 C11 1.425(5) . ?
O2 C13 1.188(6) . ?
O3 C13 1.292(5) . ?
O3 C15 1.486(9) . ?
C1 C2 1.357(5) . ?
C1 C10 1.405(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.429(5) . ?
C3 C4 1.353(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.404(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.409(4) . ?
C5 C10 1.418(5) . ?
C6 C7 1.373(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.400(5) . ?
C7 C12 1.520(5) . ?
C8 C9 1.348(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.411(5) . ?
C9 H9A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.501(7) . ?
C12 C14 1.531(5) . ?
C12 H12A 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.223(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C11 117.4(3) . . ?
C13 O3 C15 114.9(5) . . ?
C2 C1 C10 120.3(3) . . ?
C2 C1 H1A 119.9 . . ?
C10 C1 H1A 119.9 . . ?
C1 C2 O1 126.7(3) . . ?
C1 C2 C3 120.1(3) . . ?
O1 C2 C3 113.2(3) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 C10 118.2(3) . . ?
C6 C5 C10 119.5(3) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C8 117.9(3) . . ?
C6 C7 C12 120.3(4) . . ?
C8 C7 C12 121.8(3) . . ?
C9 C8 C7 122.3(3) . . ?
C9 C8 H8A 118.8 . . ?
C7 C8 H8A 118.8 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C1 C10 C9 122.5(3) . . ?
C1 C10 C5 120.0(3) . . ?
C9 C10 C5 117.5(3) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C7 109.5(4) . . ?
C13 C12 C14 110.2(4) . . ?
C7 C12 C14 112.0(3) . . ?
C13 C12 H12A 108.3 . . ?
C7 C12 H12A 108.3 . . ?
C14 C12 H12A 108.3 . . ?
O2 C13 O3 121.5(5) . . ?
O2 C13 C12 125.8(5) . . ?
O3 C13 C12 112.8(5) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 O3 114.4(8) . . ?
C16 C15 H15A 108.7 . . ?
O3 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
O3 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.916
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.916
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_compound_4

_database_code_depnum_ccdc_archive 'CCDC 687455'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 O3'
_chemical_formula_weight         272.33
_chemical_absolute_configuration RM

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   P2(1)2(1)2(1)

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'

_cell_length_a                   5.6809(12)
_cell_length_b                   8.0485(17)
_cell_length_c                   33.742(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1542.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3501
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      22.62

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13524
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3561
_reflns_number_gt                2430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0707P)²+0.1834P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_number_reflns         3561
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1551
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 -0.1901(3) -0.8062(2) -0.29986(5) 0.0818(5) Uani 1 1 d . . .
O2 O -0.1643(4) -1.0093(4) -0.02510(7) 0.1162(8) Uani 1 1 d . . .
O3 O -0.5169(4) -1.0047(2) -0.05456(5) 0.0807(5) Uani 1 1 d . . .
C1 C -0.0771(4) -0.8702(3) -0.23217(7) 0.0637(6) Uani 1 1 d . . .
H1A H 0.0552 -0.9293 -0.2402 0.076 Uiso 1 1 calc R . .
C2 C -0.2206(4) -0.8007(3) -0.25986(7) 0.0637(6) Uani 1 1 d . . .
C3 C -0.4252(4) -0.7121(3) -0.24773(8) 0.0739(7) Uani 1 1 d . . .
H3A H -0.5233 -0.6644 -0.2666 0.089 Uiso 1 1 calc R . .
C4 C -0.4772(4) -0.6972(3) -0.20890(7) 0.0698(6) Uani 1 1 d . . .
H4A H -0.6128 -0.6402 -0.2015 0.084 Uiso 1 1 calc R . .
C5 C -0.3315(4) -0.7657(3) -0.17899(6) 0.0576(5) Uani 1 1 d . . .
C6 C -0.3772(4) -0.7464(3) -0.13815(7) 0.0634(6) Uani 1 1 d . . .
H6A H -0.5143 -0.6927 -0.1302 0.076 Uiso 1 1 calc R . .
C7 C -0.2246(4) -0.8047(3) -0.10978(7) 0.0618(6) Uani 1 1 d . . .
C8 C -0.0224(4) -0.8915(3) -0.12256(7) 0.0690(6) Uani 1 1 d . . .
H8A H 0.0822 -0.9323 -0.1037 0.083 Uiso 1 1 calc R . .
C9 C 0.0235(4) -0.9170(3) -0.16137(7) 0.0686(6) Uani 1 1 d . . .
H9A H 0.1562 -0.9774 -0.1686 0.082 Uiso 1 1 calc R . .
C10 C -0.1273(4) -0.8534(3) -0.19119(7) 0.0575(5) Uani 1 1 d . . .
C11 C 0.0172(6) -0.8813(5) -0.31441(9) 0.0998(9) Uani 1 1 d . . .
H11A H 0.0172 -0.8773 -0.3428 0.150 Uiso 1 1 calc R . .
H11B H 0.0233 -0.9950 -0.3058 0.150 Uiso 1 1 calc R . .
H11C H 0.1520 -0.8228 -0.3045 0.150 Uiso 1 1 calc R . .
C12 C -0.2716(5) -0.7770(3) -0.06607(7) 0.0739(7) Uani 1 1 d . . .
H12A H -0.4180 -0.7136 -0.0635 0.089 Uiso 1 1 calc R . .
C13 C -0.0739(7) -0.6784(5) -0.04565(10) 0.1176(12) Uani 1 1 d . . .
H13A H -0.1119 -0.6635 -0.0182 0.176 Uiso 1 1 calc R . .
H13B H -0.0581 -0.5718 -0.0581 0.176 Uiso 1 1 calc R . .
H13C H 0.0716 -0.7383 -0.0479 0.176 Uiso 1 1 calc R . .
C14 C -0.3053(5) -0.9416(4) -0.04584(7) 0.0751(7) Uani 1 1 d . . .
C15 C -0.5761(7) -1.1681(4) -0.04003(10) 0.1057(11) Uani 1 1 d . . .
H15A H -0.4679 -1.1983 -0.0190 0.127 Uiso 1 1 calc R . .
H15B H -0.7336 -1.1660 -0.0290 0.127 Uiso 1 1 calc R . .
C16 C -0.566(2) -1.2861(5) -0.06946(18) 0.282(5) Uani 1 1 d . . .
H16B H -0.4477 -1.3629 -0.0598 0.338 Uiso 1 1 calc R . .
H16A H -0.7145 -1.3443 -0.0666 0.338 Uiso 1 1 calc R . .
C17 C -0.5325(16) -1.2871(6) -0.10659(14) 0.194(3) Uani 1 1 d . . .
H17A H -0.5221 -1.3998 -0.1157 0.291 Uiso 1 1 calc R . .
H17B H -0.3887 -1.2298 -0.1126 0.291 Uiso 1 1 calc R . .
H17C H -0.6615 -1.2325 -0.1196 0.291 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
O1 C2 1.362(3) . ?
O1 C11 1.412(4) . ?
O2 C14 1.195(3) . ?
O3 C14 1.338(3) . ?
O3 C15 1.443(4) . ?
C1 C2 1.360(3) . ?
C1 C10 1.418(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.424(3) . ?
C3 C4 1.348(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.417(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.411(3) . ?
C5 C10 1.418(3) . ?
C6 C7 1.374(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.412(3) . ?
C7 C12 1.515(3) . ?
C8 C9 1.351(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.418(3) . ?
C9 H9A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.502(4) . ?
C12 C13 1.538(4) . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.375(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.267(6) . ?
C16 H16B 0.9700 . ?
C16 H16A 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C11 117.7(2) . . ?
C14 O3 C15 118.7(3) . . ?
C2 C1 C10 120.6(2) . . ?
C2 C1 H1A 119.7 . . ?
C10 C1 H1A 119.7 . . ?
C1 C2 O1 126.2(2) . . ?
C1 C2 C3 119.9(2) . . ?
O1 C2 C3 113.9(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C6 C5 C4 123.0(2) . . ?
C6 C5 C10 119.27(19) . . ?
C4 C5 C10 117.7(2) . . ?
C7 C6 C5 121.8(2) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C6 C7 C8 118.0(2) . . ?
C6 C7 C12 121.1(2) . . ?
C8 C7 C12 120.9(2) . . ?
C9 C8 C7 121.9(2) . . ?
C9 C8 H8A 119.0 . . ?
C7 C8 H8A 119.0 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C9 C10 C5 117.9(2) . . ?
C9 C10 C1 122.4(2) . . ?
C5 C10 C1 119.67(19) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C7 109.6(2) . . ?
C14 C12 C13 110.2(2) . . ?
C7 C12 C13 112.5(2) . . ?
C14 C12 H12A 108.1 . . ?
C7 C12 H12A 108.1 . . ?
C13 C12 H12A 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 O3 123.9(3) . . ?
O2 C14 C12 125.6(3) . . ?
O3 C14 C12 110.5(2) . . ?
C16 C15 O3 112.0(3) . . ?
C16 C15 H15A 109.2 . . ?
O3 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
O3 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 136.5(4) . . ?
C17 C16 H16B 103.0 . . ?
C15 C16 H16B 103.0 . . ?
C17 C16 H16A 103.0 . . ?
C15 C16 H16A 103.0 . . ?
H16B C16 H16A 105.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_compound_5

_database_code_depnum_ccdc_archive 'CCDC 717531'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 O3'
_chemical_formula_weight         286.36
_chemical_absolute_configuration RM

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   P2(1)

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

_cell_length_a                   8.067(2)
_cell_length_b                   5.7361(15)
_cell_length_c                   17.495(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.528(4)
_cell_angle_gamma                90.00
_cell_volume                     795.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    761
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.31

_exptl_crystal_description       needle
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7035
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.60
_reflns_number_total             3332
_reflns_number_gt                1512
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0246P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4.3(15)
_refine_ls_number_reflns         3332
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.7844(3) 1.2104(4) 1.07289(12) 0.0715(7) Uani 1 1 d . . .
O2 O 0.2736(2) 0.8152(4) 0.61346(11) 0.0657(6) Uani 1 1 d . . .
O3 O 0.2768(3) 1.1417(4) 0.54411(12) 0.0825(7) Uani 1 1 d . . .
C1 C 0.8040(4) 0.8905(6) 0.89876(18) 0.0655(9) Uani 1 1 d . . .
H1A H 0.8569 0.7560 0.8857 0.079 Uiso 1 1 calc R . .
C2 C 0.8284(4) 0.9613(6) 0.97360(19) 0.0698(10) Uani 1 1 d . . .
H2A H 0.8965 0.8737 1.0117 0.084 Uiso 1 1 calc R . .
C3 C 0.7518(4) 1.1663(6) 0.99456(19) 0.0579(8) Uani 1 1 d . . .
C4 C 0.6540(3) 1.2975(6) 0.93987(17) 0.0579(8) Uani 1 1 d . . .
H4A H 0.6047 1.4335 0.9541 0.070 Uiso 1 1 calc R . .
C5 C 0.6266(4) 1.2275(5) 0.86087(17) 0.0539(8) Uani 1 1 d . . .
C6 C 0.5241(3) 1.3559(6) 0.80101(17) 0.0626(9) Uani 1 1 d . . .
H6A H 0.4748 1.4942 0.8133 0.075 Uiso 1 1 calc R . .
C7 C 0.4962(3) 1.2817(5) 0.72591(17) 0.0607(9) Uani 1 1 d . . .
H7A H 0.4291 1.3710 0.6880 0.073 Uiso 1 1 calc R . .
C8 C 0.5662(3) 1.0740(5) 0.70454(17) 0.0526(8) Uani 1 1 d . . .
C9 C 0.6651(3) 0.9465(5) 0.76095(17) 0.0542(8) Uani 1 1 d . . .
H9A H 0.7120 0.8079 0.7474 0.065 Uiso 1 1 calc R . .
C10 C 0.6984(3) 1.0195(5) 0.83971(17) 0.0526(8) Uani 1 1 d . . .
C11 C 0.7067(4) 1.4105(7) 1.09870(17) 0.0885(12) Uani 1 1 d . . .
H11A H 0.7384 1.4236 1.1542 0.133 Uiso 1 1 calc R . .
H11B H 0.5865 1.3960 1.0847 0.133 Uiso 1 1 calc R . .
H11C H 0.7429 1.5471 1.0746 0.133 Uiso 1 1 calc R . .
C12 C 0.5360(3) 0.9948(5) 0.61994(16) 0.0571(9) Uani 1 1 d . . .
H12A H 0.5765 0.8342 0.6182 0.068 Uiso 1 1 calc R . .
C13 C 0.6334(4) 1.1488(7) 0.57163(16) 0.0851(11) Uani 1 1 d . . .
H13A H 0.6138 1.0948 0.5188 0.128 Uiso 1 1 calc R . .
H13B H 0.7518 1.1407 0.5928 0.128 Uiso 1 1 calc R . .
H13C H 0.5957 1.3072 0.5731 0.128 Uiso 1 1 calc R . .
C14 C 0.3505(4) 0.9984(6) 0.58726(18) 0.0594(8) Uani 1 1 d . . .
C15 C 0.0925(4) 0.8040(7) 0.58925(17) 0.0774(11) Uani 1 1 d . . .
H15A H 0.0632 0.7840 0.5334 0.093 Uiso 1 1 calc R . .
H15B H 0.0407 0.9465 0.6033 0.093 Uiso 1 1 calc R . .
C16 C 0.0329(4) 0.5993(7) 0.63015(18) 0.0794(10) Uani 1 1 d . . .
H16A H -0.0880 0.5843 0.6131 0.095 Uiso 1 1 calc R . .
H16B H 0.0846 0.4595 0.6139 0.095 Uiso 1 1 calc R . .
C17 C 0.0687(4) 0.6090(7) 0.71640(18) 0.0778(10) Uani 1 1 d . . .
H17A H 0.0149 0.7465 0.7329 0.093 Uiso 1 1 calc R . .
H17B H 0.1893 0.6263 0.7337 0.093 Uiso 1 1 calc R . .
C18 C 0.0104(4) 0.3998(7) 0.75571(19) 0.1005(13) Uani 1 1 d . . .
H18A H 0.0359 0.4210 0.8110 0.151 Uiso 1 1 calc R . .
H18B H 0.0672 0.2632 0.7419 0.151 Uiso 1 1 calc R . .
H18C H -0.1090 0.3811 0.7393 0.151 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
O1 C3 1.371(3) . ?
O1 C11 1.420(4) . ?
O2 C14 1.343(3) . ?
O2 C15 1.446(3) . ?
O3 C14 1.198(3) . ?
C1 C2 1.351(4) . ?
C1 C10 1.421(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.408(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.352(4) . ?
C4 C5 1.417(3) . ?
C4 H4A 0.9300 . ?
C5 C10 1.405(3) . ?
C5 C6 1.417(4) . ?
C6 C7 1.360(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.398(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.363(4) . ?
C8 C12 1.525(4) . ?
C9 C10 1.418(4) . ?
C9 H9A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.502(4) . ?
C12 C13 1.534(4) . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.500(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.485(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.501(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C11 116.8(2) . . ?
C14 O2 C15 116.1(2) . . ?
C2 C1 C10 120.7(3) . . ?
C2 C1 H1A 119.7 . . ?
C10 C1 H1A 119.7 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 O1 125.8(3) . . ?
C4 C3 C2 120.5(3) . . ?
O1 C3 C2 113.7(3) . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C10 C5 C6 117.4(3) . . ?
C10 C5 C4 120.0(3) . . ?
C6 C5 C4 122.6(3) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7A 119.3 . . ?
C8 C7 H7A 119.3 . . ?
C9 C8 C7 118.4(3) . . ?
C9 C8 C12 120.8(3) . . ?
C7 C8 C12 120.9(3) . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 H9A 119.1 . . ?
C10 C9 H9A 119.1 . . ?
C5 C10 C9 119.5(3) . . ?
C5 C10 C1 118.1(3) . . ?
C9 C10 C1 122.3(3) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C8 109.7(2) . . ?
C14 C12 C13 111.0(3) . . ?
C8 C12 C13 110.9(2) . . ?
C14 C12 H12A 108.4 . . ?
C8 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O2 123.0(3) . . ?
O3 C14 C12 126.5(3) . . ?
O2 C14 C12 110.5(3) . . ?
O2 C15 C16 106.9(3) . . ?
O2 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O2 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.6 . . ?
C17 C16 C15 115.8(3) . . ?
C17 C16 H16A 108.3 . . ?
C15 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
C15 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C16 C17 C18 114.6(3) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_compound_6

_database_code_depnum_ccdc_archive 'CCDC 1407685'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 O3'
_chemical_formula_weight         300.38
_chemical_absolute_configuration RM

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   P2(1)2(1)2(1)

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'

_cell_length_a                   5.806(4)
_cell_length_b                   8.297(6)
_cell_length_c                   37.02(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1784(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    566(2)
_cell_measurement_reflns_used    3773
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.30

_exptl_crystal_description       bar
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_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      566(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9901
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         27.28
_reflns_number_total             3909
_reflns_number_gt                2470
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1066P)²+0.7118P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         3909
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.2304
_refine_ls_wR_factor_gt          0.2000
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.1081(6) 0.5311(4) 1.03963(9) 0.0560(8) Uani 1 1 d . . .
C2 C -0.0278(6) 0.5728(4) 1.01085(9) 0.0538(8) Uani 1 1 d . . .
H2A H -0.1594 0.6346 1.0145 0.065 Uiso 1 1 calc R . .
C3 C 0.0328(5) 0.5212(3) 0.97533(9) 0.0499(7) Uani 1 1 d . . .
C4 C 0.2381(5) 0.4298(3) 0.96968(10) 0.0521(8) Uani 1 1 d . . .
C5 C 0.3758(5) 0.3933(4) 1.00005(10) 0.0577(9) Uani 1 1 d . . .
H5A H 0.5107 0.3346 0.9969 0.069 Uiso 1 1 calc R . .
C6 C 0.3152(6) 0.4423(4) 1.03412(11) 0.0614(9) Uani 1 1 d . . .
H6A H 0.4094 0.4175 1.0537 0.074 Uiso 1 1 calc R . .
C7 C -0.1090(6) 0.5548(4) 0.94467(10) 0.0607(9) Uani 1 1 d . . .
H7A H -0.2428 0.6151 0.9475 0.073 Uiso 1 1 calc R . .
C8 C -0.0500(6) 0.4991(4) 0.91125(10) 0.0649(10) Uani 1 1 d . . .
H8A H -0.1441 0.5233 0.8917 0.078 Uiso 1 1 calc R . .
C9 C 0.1526(6) 0.4045(4) 0.90554(10) 0.0611(9) Uani 1 1 d . . .
C10 C 0.2905(5) 0.3730(4) 0.93432(10) 0.0540(8) Uani 1 1 d . . .
H10A H 0.4234 0.3125 0.9308 0.065 Uiso 1 1 calc R . .
C11 C 0.2175(8) 0.3455(5) 0.86744(11) 0.0765(11) Uani 1 1 d . . .
H11A H 0.3481 0.2713 0.8696 0.092 Uiso 1 1 calc R . .
C12 C 0.0144(9) 0.2535(6) 0.85132(13) 0.0895(13) Uani 1 1 d . . .
C13 C -0.1573(13) -0.0100(9) 0.84643(17) 0.146(3) Uani 1 1 d . . .
H13A H -0.1916 -0.0890 0.8650 0.176 Uiso 1 1 calc R . .
H13B H -0.2962 0.0518 0.8420 0.176 Uiso 1 1 calc R . .
C14 C -0.0929(13) -0.0910(9) 0.81435(18) 0.135(2) Uani 1 1 d . . .
H14A H 0.0544 -0.1431 0.8184 0.162 Uiso 1 1 calc R . .
H14B H -0.0706 -0.0111 0.7955 0.162 Uiso 1 1 calc R . .
C15 C -0.2573(12) -0.2138(8) 0.80089(18) 0.130(2) Uani 1 1 d . . .
H15A H -0.4129 -0.1716 0.8024 0.156 Uiso 1 1 calc R . .
H15B H -0.2485 -0.3090 0.8160 0.156 Uiso 1 1 calc R . .
C16 C -0.2057(14) -0.2592(10) 0.7624(2) 0.148(3) Uani 1 1 d . . .
H16A H -0.1933 -0.1619 0.7480 0.177 Uiso 1 1 calc R . .
H16B H -0.0582 -0.3139 0.7615 0.177 Uiso 1 1 calc R . .
C17 C -0.3833(14) -0.3647(12) 0.7463(2) 0.188(4) Uani 1 1 d . . .
H17A H -0.3390 -0.3932 0.7222 0.282 Uiso 1 1 calc R . .
H17B H -0.5280 -0.3089 0.7458 0.282 Uiso 1 1 calc R . .
H17C H -0.3981 -0.4607 0.7606 0.282 Uiso 1 1 calc R . .
C18 C -0.1442(8) 0.6552(5) 1.08315(12) 0.0833(13) Uani 1 1 d . . .
H18A H -0.1530 0.6747 1.1087 0.125 Uiso 1 1 calc R . .
H18B H -0.2741 0.5918 1.0757 0.125 Uiso 1 1 calc R . .
H18C H -0.1452 0.7562 1.0705 0.125 Uiso 1 1 calc R . .
C19 C 0.2891(12) 0.4862(7) 0.84247(13) 0.1174(19) Uani 1 1 d . . .
H19A H 0.3288 0.4447 0.8191 0.176 Uiso 1 1 calc R . .
H19B H 0.4197 0.5407 0.8527 0.176 Uiso 1 1 calc R . .
H19C H 0.1632 0.5605 0.8402 0.176 Uiso 1 1 calc R . .
O1 O -0.1379(9) 0.3143(6) 0.83364(14) 0.1458(18) Uani 1 1 d . . .
O2 O 0.0232(7) 0.0979(5) 0.85941(10) 0.1118(12) Uani 1 1 d . . .
O3 O 0.0657(5) 0.5695(3) 1.07501(7) 0.0739(8) 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
C1 O3 1.370(4) . ?
C1 C2 1.370(5) . ?
C1 C6 1.425(5) . ?
C2 C3 1.427(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.428(4) . ?
C3 C7 1.430(5) . ?
C4 C5 1.412(5) . ?
C4 C10 1.424(5) . ?
C5 C6 1.371(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.364(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.430(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.358(5) . ?
C9 C11 1.540(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.526(7) . ?
C11 C19 1.546(7) . ?
C11 H11A 0.9800 . ?
C12 O1 1.210(6) . ?
C12 O2 1.326(6) . ?
C13 C14 1.415(8) . ?
C13 O2 1.460(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.483(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.505(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.477(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O3 1.443(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 C2 125.5(3) . . ?
O3 C1 C6 114.1(3) . . ?
C2 C1 C6 120.3(3) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 C7 122.1(3) . . ?
C4 C3 C7 117.9(3) . . ?
C5 C4 C10 122.7(3) . . ?
C5 C4 C3 118.0(3) . . ?
C10 C4 C3 119.2(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
C8 C7 C3 120.6(3) . . ?
C8 C7 H7A 119.7 . . ?
C3 C7 H7A 119.7 . . ?
C7 C8 C9 121.8(3) . . ?
C7 C8 H8A 119.1 . . ?
C9 C8 H8A 119.1 . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 C11 120.9(3) . . ?
C8 C9 C11 120.8(3) . . ?
C9 C10 C4 122.1(3) . . ?
C9 C10 H10A 118.9 . . ?
C4 C10 H10A 118.9 . . ?
C12 C11 C9 109.2(3) . . ?
C12 C11 C19 110.6(4) . . ?
C9 C11 C19 111.9(3) . . ?
C12 C11 H11A 108.4 . . ?
C9 C11 H11A 108.4 . . ?
C19 C11 H11A 108.4 . . ?
O1 C12 O2 123.8(5) . . ?
O1 C12 C11 124.6(5) . . ?
O2 C12 C11 111.6(5) . . ?
C14 C13 O2 112.2(5) . . ?
C14 C13 H13A 109.2 . . ?
O2 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
O2 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 116.0(6) . . ?
C13 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 C16 111.3(6) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 113.0(6) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 O2 C13 119.7(5) . . ?
C1 O3 C18 117.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.28
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039




#==END of File










