# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_fred13
_database_code_depnum_ccdc_archive 'CCDC 1816383'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   5.5798(4)
_cell_length_b                   26.592(2)
_cell_length_c                   8.0005(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.6560(9)
_cell_angle_gamma                90
_cell_volume                     1124.72(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6979
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      29.29

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7095
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13822
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.794
_diffrn_reflns_theta_max         29.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2939
_reflns_number_gt                2630
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+0.4252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2939
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.49890(18) 0.15760(4) 0.24972(13) 0.0156(2) Uani 1 1 d . . . . .
H1 H 0.3453 0.1795 0.2222 0.019 Uiso 1 1 calc R U . . .
C2 C 0.5861(2) 0.14523(4) 0.09509(14) 0.0192(2) Uani 1 1 d . . . . .
H2 H 0.4894 0.1281 -0.0089 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8206(2) 0.16217(5) 0.12781(14) 0.0232(2) Uani 1 1 d . . . . .
H3 H 0.9100 0.1583 0.0455 0.028 Uiso 1 1 calc R U . . .
C5 C 0.74384(19) 0.18057(4) 0.38083(13) 0.0161(2) Uani 1 1 d . . . . .
C6 C 0.51253(18) 0.11422(4) 0.38656(13) 0.01484(19) Uani 1 1 d . . . . .
H6 H 0.3822 0.1198 0.4462 0.018 Uiso 1 1 calc R U . . .
C7 C 0.77426(19) 0.13446(4) 0.50487(13) 0.0155(2) Uani 1 1 d . . . . .
H7 H 0.9207 0.1122 0.5097 0.019 Uiso 1 1 calc R U . . .
C8 C 0.7791(2) 0.15574(4) 0.68307(14) 0.0231(2) Uani 1 1 d . . . . .
H8A H 0.9551 0.1607 0.7613 0.028 Uiso 1 1 calc R U . . .
H8B H 0.6906 0.1331 0.7422 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6398(2) 0.20637(4) 0.63642(16) 0.0254(2) Uani 1 1 d . . . . .
H9A H 0.4541 0.2015 0.5941 0.030 Uiso 1 1 calc R U . . .
H9B H 0.6853 0.2293 0.7394 0.030 Uiso 1 1 calc R U . . .
C10 C 0.7334(2) 0.22695(4) 0.48907(15) 0.0224(2) Uani 1 1 d . . . . .
H10A H 0.6143 0.2522 0.4170 0.027 Uiso 1 1 calc R U . . .
H10B H 0.9028 0.2425 0.5382 0.027 Uiso 1 1 calc R U . . .
C11 C 0.49715(18) 0.06176(4) 0.32046(13) 0.0148(2) Uani 1 1 d . . . . .
C12 C 0.25760(19) 0.04192(4) 0.18730(15) 0.0211(2) Uani 1 1 d . . . . .
H12A H 0.2186 0.0605 0.0744 0.025 Uiso 1 1 calc R U . . .
H12B H 0.1124 0.0451 0.2324 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3146(2) -0.01360(4) 0.16259(14) 0.0204(2) Uani 1 1 d . . . . .
H13A H 0.2039 -0.0359 0.2047 0.025 Uiso 1 1 calc R U . . .
H13B H 0.2890 -0.0211 0.0368 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5912(2) -0.02070(4) 0.27302(14) 0.0189(2) Uani 1 1 d . . . . .
C15 C 0.67996(19) 0.02666(4) 0.36616(13) 0.0172(2) Uani 1 1 d . . . . .
H15 H 0.8443 0.0318 0.4477 0.021 Uiso 1 1 calc R U . . .
O1 O 0.92662(15) 0.18566(3) 0.28805(10) 0.02370(19) Uani 1 1 d . . . . .
O2 O 0.71460(17) -0.05901(3) 0.27974(12) 0.0290(2) 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 C2 1.5035(14) . ?
C1 C5 1.5570(14) . ?
C1 C6 1.5752(13) . ?
C1 H1 1.0000 . ?
C2 C3 1.3286(15) . ?
C2 H2 0.9500 . ?
C3 O1 1.3778(13) . ?
C3 H3 0.9500 . ?
C5 O1 1.4470(12) . ?
C5 C10 1.5187(14) . ?
C5 C7 1.5522(14) . ?
C6 C11 1.4848(13) . ?
C6 C7 1.5601(13) . ?
C6 H6 1.0000 . ?
C7 C8 1.5260(14) . ?
C7 H7 1.0000 . ?
C8 C9 1.5396(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5350(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.3441(14) . ?
C11 C12 1.5129(14) . ?
C12 C13 1.5365(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5247(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O2 1.2212(13) . ?
C14 C15 1.4664(14) . ?
C15 H15 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
C2 C1 C5 101.24(8) . . ?
C2 C1 C6 117.08(8) . . ?
C5 C1 C6 88.99(7) . . ?
C2 C1 H1 115.2 . . ?
C5 C1 H1 115.2 . . ?
C6 C1 H1 115.2 . . ?
C3 C2 C1 108.74(9) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
C2 C3 O1 116.08(10) . . ?
C2 C3 H3 122.0 . . ?
O1 C3 H3 122.0 . . ?
O1 C5 C10 112.23(8) . . ?
O1 C5 C7 116.80(8) . . ?
C10 C5 C7 107.05(8) . . ?
O1 C5 C1 107.58(8) . . ?
C10 C5 C1 121.16(9) . . ?
C7 C5 C1 90.78(7) . . ?
C11 C6 C7 118.45(8) . . ?
C11 C6 C1 117.13(8) . . ?
C7 C6 C1 89.82(7) . . ?
C11 C6 H6 110.0 . . ?
C7 C6 H6 110.0 . . ?
C1 C6 H6 110.0 . . ?
C8 C7 C5 105.66(8) . . ?
C8 C7 C6 115.35(8) . . ?
C5 C7 C6 89.71(7) . . ?
C8 C7 H7 114.4 . . ?
C5 C7 H7 114.4 . . ?
C6 C7 H7 114.4 . . ?
C7 C8 C9 103.95(9) . . ?
C7 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C10 C9 C8 103.21(9) . . ?
C10 C9 H9A 111.1 . . ?
C8 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C5 C10 C9 103.46(8) . . ?
C5 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
C5 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
C15 C11 C6 127.10(9) . . ?
C15 C11 C12 111.85(9) . . ?
C6 C11 C12 121.05(9) . . ?
C11 C12 C13 104.65(8) . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C14 C13 C12 104.91(8) . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
O2 C14 C15 126.86(10) . . ?
O2 C14 C13 125.50(10) . . ?
C15 C14 C13 107.64(9) . . ?
C11 C15 C14 110.76(9) . . ?
C11 C15 H15 124.6 . . ?
C14 C15 H15 124.6 . . ?
C3 O1 C5 105.77(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 -4.87(11) . . . . ?
C6 C1 C2 C3 -99.53(11) . . . . ?
C1 C2 C3 O1 0.49(14) . . . . ?
C2 C1 C5 O1 7.44(10) . . . . ?
C6 C1 C5 O1 124.88(8) . . . . ?
C2 C1 C5 C10 138.38(9) . . . . ?
C6 C1 C5 C10 -104.18(10) . . . . ?
C2 C1 C5 C7 -111.07(8) . . . . ?
C6 C1 C5 C7 6.36(7) . . . . ?
C2 C1 C6 C11 -26.48(12) . . . . ?
C5 C1 C6 C11 -128.59(9) . . . . ?
C2 C1 C6 C7 95.78(9) . . . . ?
C5 C1 C6 C7 -6.33(7) . . . . ?
O1 C5 C7 C8 127.07(9) . . . . ?
C10 C5 C7 C8 0.31(11) . . . . ?
C1 C5 C7 C8 -122.74(8) . . . . ?
O1 C5 C7 C6 -116.62(9) . . . . ?
C10 C5 C7 C6 116.63(8) . . . . ?
C1 C5 C7 C6 -6.43(7) . . . . ?
C11 C6 C7 C8 -125.28(10) . . . . ?
C1 C6 C7 C8 113.59(9) . . . . ?
C11 C6 C7 C5 127.48(9) . . . . ?
C1 C6 C7 C5 6.35(7) . . . . ?
C5 C7 C8 C9 23.91(11) . . . . ?
C6 C7 C8 C9 -73.39(11) . . . . ?
C7 C8 C9 C10 -39.25(11) . . . . ?
O1 C5 C10 C9 -153.85(9) . . . . ?
C7 C5 C10 C9 -24.44(11) . . . . ?
C1 C5 C10 C9 77.22(11) . . . . ?
C8 C9 C10 C5 39.22(11) . . . . ?
C7 C6 C11 C15 7.90(15) . . . . ?
C1 C6 C11 C15 113.77(11) . . . . ?
C7 C6 C11 C12 -172.32(9) . . . . ?
C1 C6 C11 C12 -66.45(12) . . . . ?
C15 C11 C12 C13 2.94(12) . . . . ?
C6 C11 C12 C13 -176.87(9) . . . . ?
C11 C12 C13 C14 -4.26(11) . . . . ?
C12 C13 C14 O2 -174.98(11) . . . . ?
C12 C13 C14 C15 4.29(11) . . . . ?
C6 C11 C15 C14 179.58(9) . . . . ?
C12 C11 C15 C14 -0.22(12) . . . . ?
O2 C14 C15 C11 176.61(11) . . . . ?
C13 C14 C15 C11 -2.65(12) . . . . ?
C2 C3 O1 C5 4.57(13) . . . . ?
C10 C5 O1 C3 -143.11(9) . . . . ?
C7 C5 O1 C3 92.73(10) . . . . ?
C1 C5 O1 C3 -7.41(11) . . . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_fred14
_database_code_depnum_ccdc_archive 'CCDC 1816390'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   16.348(8)
_cell_length_b                   6.781(3)
_cell_length_c                   10.091(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.020(6)
_cell_angle_gamma                90
_cell_volume                     1101.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    4664
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.41

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2844
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12488
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.530
_diffrn_reflns_theta_max         28.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2757
_reflns_number_gt                2178
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1410P)²+0.0861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2757
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14274(9) 0.5356(2) 0.08460(15) 0.0247(4) Uani 1 1 d . . . . .
H1 H 0.1055 0.5459 0.1531 0.030 Uiso 1 1 calc R U . . .
C2 C 0.08822(10) 0.4877(3) -0.05071(16) 0.0281(4) Uani 1 1 d . . . . .
C3 C 0.08111(11) 0.6661(3) -0.14023(18) 0.0343(4) Uani 1 1 d . . . . .
H3A H 0.0225 0.6904 -0.1814 0.041 Uiso 1 1 calc R U . . .
H3B H 0.1141 0.6487 -0.2129 0.041 Uiso 1 1 calc R U . . .
C4 C 0.11526(11) 0.8366(3) -0.04761(18) 0.0319(4) Uani 1 1 d . . . . .
H4A H 0.1440 0.9341 -0.0964 0.038 Uiso 1 1 calc R U . . .
H4B H 0.0700 0.9038 -0.0117 0.038 Uiso 1 1 calc R U . . .
C5 C 0.17565(9) 0.7405(2) 0.06470(15) 0.0251(4) Uani 1 1 d . . . . .
C6 C 0.24447(10) 0.8260(2) 0.12917(17) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.2568 0.9529 0.0980 0.032 Uiso 1 1 calc R U . . .
C7 C 0.30502(10) 0.7448(2) 0.24580(16) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.2817 0.7717 0.3293 0.031 Uiso 1 1 calc R U . . .
C8 C 0.32287(9) 0.5228(2) 0.24275(16) 0.0254(4) Uani 1 1 d . . . . .
C9 C 0.33839(10) 0.4520(2) 0.10738(17) 0.0283(4) Uani 1 1 d . . . . .
H9 H 0.3887 0.4692 0.0736 0.034 Uiso 1 1 calc R U . . .
C10 C 0.27127(11) 0.3625(2) 0.04312(18) 0.0295(4) Uani 1 1 d . . . . .
H10 H 0.2657 0.3031 -0.0432 0.035 Uiso 1 1 calc R U . . .
C11 C 0.20525(10) 0.3705(2) 0.12966(16) 0.0269(4) Uani 1 1 d . . . . .
H11 H 0.1761 0.2406 0.1284 0.032 Uiso 1 1 calc R U . . .
C12 C 0.39213(10) 0.8335(3) 0.26648(18) 0.0318(4) Uani 1 1 d . . . . .
H12A H 0.3927 0.9658 0.3082 0.038 Uiso 1 1 calc R U . . .
H12B H 0.4122 0.8451 0.1797 0.038 Uiso 1 1 calc R U . . .
C13 C 0.44633(11) 0.6879(3) 0.36105(19) 0.0355(4) Uani 1 1 d . . . . .
H13A H 0.4991 0.6620 0.3288 0.043 Uiso 1 1 calc R U . . .
H13B H 0.4593 0.7422 0.4534 0.043 Uiso 1 1 calc R U . . .
C14 C 0.39524(11) 0.4965(3) 0.35947(17) 0.0320(4) Uani 1 1 d . . . . .
H14A H 0.4292 0.3803 0.3446 0.038 Uiso 1 1 calc R U . . .
H14B H 0.3748 0.4794 0.4455 0.038 Uiso 1 1 calc R U . . .
O1 O 0.05722(8) 0.32827(19) -0.07939(13) 0.0381(4) Uani 1 1 d . . . . .
O2 O 0.25110(7) 0.41038(16) 0.26147(11) 0.0272(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.515(2) . ?
C1 C2 1.530(2) . ?
C1 C11 1.531(2) . ?
C1 H1 1.0000 . ?
C2 O1 1.207(2) . ?
C2 C3 1.502(2) . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.515(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.331(2) . ?
C6 C7 1.504(2) . ?
C6 H6 0.9500 . ?
C7 C12 1.526(2) . ?
C7 C8 1.535(2) . ?
C7 H7 1.0000 . ?
C8 O2 1.4389(19) . ?
C8 C9 1.510(2) . ?
C8 C14 1.528(2) . ?
C9 C10 1.321(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.503(2) . ?
C10 H10 0.9500 . ?
C11 O2 1.4342(19) . ?
C11 H11 1.0000 . ?
C12 C13 1.542(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.542(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 103.98(13) . . ?
C5 C1 C11 118.40(13) . . ?
C2 C1 C11 111.40(13) . . ?
C5 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
C11 C1 H1 107.5 . . ?
O1 C2 C3 126.27(16) . . ?
O1 C2 C1 123.99(15) . . ?
C3 C2 C1 109.73(14) . . ?
C2 C3 C4 105.03(14) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C5 C4 C3 104.66(14) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C6 C5 C4 124.31(15) . . ?
C6 C5 C1 128.63(14) . . ?
C4 C5 C1 107.05(13) . . ?
C5 C6 C7 127.46(15) . . ?
C5 C6 H6 116.3 . . ?
C7 C6 H6 116.3 . . ?
C6 C7 C12 115.73(14) . . ?
C6 C7 C8 116.41(13) . . ?
C12 C7 C8 102.29(13) . . ?
C6 C7 H7 107.3 . . ?
C12 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
O2 C8 C9 102.69(12) . . ?
O2 C8 C14 112.15(13) . . ?
C9 C8 C14 115.53(14) . . ?
O2 C8 C7 110.76(13) . . ?
C9 C8 C7 113.09(13) . . ?
C14 C8 C7 102.91(13) . . ?
C10 C9 C8 109.51(15) . . ?
C10 C9 H9 125.2 . . ?
C8 C9 H9 125.2 . . ?
C9 C10 C11 108.51(15) . . ?
C9 C10 H10 125.7 . . ?
C11 C10 H10 125.7 . . ?
O2 C11 C10 103.49(13) . . ?
O2 C11 C1 110.60(13) . . ?
C10 C11 C1 111.33(14) . . ?
O2 C11 H11 110.4 . . ?
C10 C11 H11 110.4 . . ?
C1 C11 H11 110.4 . . ?
C7 C12 C13 104.74(14) . . ?
C7 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C7 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C14 C13 C12 106.30(14) . . ?
C14 C13 H13A 110.5 . . ?
C12 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C8 C14 C13 104.80(14) . . ?
C8 C14 H14A 110.8 . . ?
C13 C14 H14A 110.8 . . ?
C8 C14 H14B 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
C11 O2 C8 106.54(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 O1 172.43(16) . . . . ?
C11 C1 C2 O1 43.8(2) . . . . ?
C5 C1 C2 C3 -6.64(17) . . . . ?
C11 C1 C2 C3 -135.24(15) . . . . ?
O1 C2 C3 C4 168.43(17) . . . . ?
C1 C2 C3 C4 -12.53(18) . . . . ?
C2 C3 C4 C5 26.77(17) . . . . ?
C3 C4 C5 C6 147.39(17) . . . . ?
C3 C4 C5 C1 -31.80(16) . . . . ?
C2 C1 C5 C6 -155.49(16) . . . . ?
C11 C1 C5 C6 -31.3(2) . . . . ?
C2 C1 C5 C4 23.66(16) . . . . ?
C11 C1 C5 C4 147.85(14) . . . . ?
C4 C5 C6 C7 176.64(15) . . . . ?
C1 C5 C6 C7 -4.3(3) . . . . ?
C5 C6 C7 C12 158.18(16) . . . . ?
C5 C6 C7 C8 38.0(2) . . . . ?
C6 C7 C8 O2 -68.87(17) . . . . ?
C12 C7 C8 O2 163.94(13) . . . . ?
C6 C7 C8 C9 45.77(18) . . . . ?
C12 C7 C8 C9 -81.41(15) . . . . ?
C6 C7 C8 C14 171.10(13) . . . . ?
C12 C7 C8 C14 43.91(16) . . . . ?
O2 C8 C9 C10 17.09(17) . . . . ?
C14 C8 C9 C10 139.48(15) . . . . ?
C7 C8 C9 C10 -102.31(16) . . . . ?
C8 C9 C10 C11 1.17(18) . . . . ?
C9 C10 C11 O2 -19.12(17) . . . . ?
C9 C10 C11 C1 99.70(16) . . . . ?
C5 C1 C11 O2 64.27(17) . . . . ?
C2 C1 C11 O2 -175.28(12) . . . . ?
C5 C1 C11 C10 -50.21(19) . . . . ?
C2 C1 C11 C10 70.24(17) . . . . ?
C6 C7 C12 C13 -163.98(14) . . . . ?
C8 C7 C12 C13 -36.36(17) . . . . ?
C7 C12 C13 C14 15.32(18) . . . . ?
O2 C8 C14 C13 -153.41(14) . . . . ?
C9 C8 C14 C13 89.39(18) . . . . ?
C7 C8 C14 C13 -34.33(16) . . . . ?
C12 C13 C14 C8 11.85(18) . . . . ?
C10 C11 O2 C8 29.89(15) . . . . ?
C1 C11 O2 C8 -89.43(15) . . . . ?
C9 C8 O2 C11 -28.96(15) . . . . ?
C14 C8 O2 C11 -153.61(13) . . . . ?
C7 C8 O2 C11 92.05(15) . . . . ?

_refine_diff_density_max         0.646
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_fred39a
_database_code_depnum_ccdc_archive 'CCDC 1816388'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.7209(5)
_cell_length_b                   13.1604(6)
_cell_length_c                   8.2158(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.7891(5)
_cell_angle_gamma                90
_cell_volume                     1115.44(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    5745
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.92

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.149
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7151
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13445
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.974
_diffrn_reflns_theta_max         29.177
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2907
_reflns_number_gt                2527
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0675P)²+0.5056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.70806(13) 1.18031(10) 0.61604(17) 0.0246(3) Uani 1 1 d . . . . .
H1A H 0.6427 1.2074 0.6696 0.029 Uiso 1 1 calc R U . . .
H1B H 0.6945 1.2115 0.5029 0.029 Uiso 1 1 calc R U . . .
C2 C 0.84612(13) 1.19987(10) 0.72716(19) 0.0288(3) Uani 1 1 d . . . . .
H2A H 0.8529 1.2678 0.7805 0.035 Uiso 1 1 calc R U . . .
H2B H 0.9098 1.1952 0.6599 0.035 Uiso 1 1 calc R U . . .
C3 C 0.86863(13) 1.11552(10) 0.86116(18) 0.0269(3) Uani 1 1 d . . . . .
H3A H 0.9624 1.1023 0.9087 0.032 Uiso 1 1 calc R U . . .
H3B H 0.8310 1.1346 0.9544 0.032 Uiso 1 1 calc R U . . .
C4 C 0.80012(12) 1.02184(9) 0.76700(15) 0.0202(2) Uani 1 1 d . . . . .
C5 C 0.70107(11) 1.06464(9) 0.60386(15) 0.0193(2) Uani 1 1 d . . . . .
H5 H 0.6115 1.0364 0.5827 0.023 Uiso 1 1 calc R U . . .
C6 C 0.78281(12) 1.01567(9) 0.49273(16) 0.0215(3) Uani 1 1 d . . . . .
H6 H 0.8273 1.0679 0.4399 0.026 Uiso 1 1 calc R U . . .
C7 C 0.87638(12) 0.96660(10) 0.65371(16) 0.0230(3) Uani 1 1 d . . . . .
H7 H 0.9664 0.9939 0.6747 0.028 Uiso 1 1 calc R U . . .
C8 C 0.87602(12) 0.85252(10) 0.66091(16) 0.0245(3) Uani 1 1 d . . . . .
H8 H 0.9321 0.8202 0.7565 0.029 Uiso 1 1 calc R U . . .
C9 C 0.80094(12) 0.79387(9) 0.54001(15) 0.0219(3) Uani 1 1 d . . . . .
H9 H 0.8055 0.7220 0.5503 0.026 Uiso 1 1 calc R U . . .
C10 C 0.71158(12) 0.84104(10) 0.39164(15) 0.0217(3) Uani 1 1 d . . . . .
C11 C 0.61243(12) 0.79168(9) 0.25639(15) 0.0207(2) Uani 1 1 d . . . . .
C12 C 0.54460(13) 0.87349(10) 0.13304(15) 0.0246(3) Uani 1 1 d . . . . .
H12A H 0.4507 0.8748 0.1245 0.029 Uiso 1 1 calc R U . . .
H12B H 0.5561 0.8610 0.0192 0.029 Uiso 1 1 calc R U . . .
C13 C 0.60871(13) 0.97411(10) 0.20554(16) 0.0240(3) Uani 1 1 d . . . . .
H13A H 0.6518 1.0067 0.1267 0.029 Uiso 1 1 calc R U . . .
H13B H 0.5442 1.0218 0.2287 0.029 Uiso 1 1 calc R U . . .
C14 C 0.70583(12) 0.94284(10) 0.36612(15) 0.0220(3) Uani 1 1 d . . . . .
O1 O 0.58492(9) 0.70110(7) 0.24407(11) 0.0255(2) Uani 1 1 d . . . . .
O2 O 0.75436(10) 0.96159(7) 0.88045(11) 0.0254(2) Uani 1 1 d . . . . .
H2 H 0.7115 0.9125 0.8280 0.038 Uiso 1 1 calc R U . . .


_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 C5 1.5260(17) . ?
C1 C2 1.5347(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.535(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5326(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O2 1.4096(15) . ?
C4 C5 1.5706(17) . ?
C4 C7 1.5739(17) . ?
C5 C6 1.5660(16) . ?
C5 H5 1.0000 . ?
C6 C14 1.4881(17) . ?
C6 C7 1.5655(18) . ?
C6 H6 1.0000 . ?
C7 C8 1.5026(18) . ?
C7 H7 1.0000 . ?
C8 C9 1.3398(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.4675(17) . ?
C9 H9 0.9500 . ?
C10 C14 1.3549(17) . ?
C10 C11 1.4642(17) . ?
C11 O1 1.2256(15) . ?
C11 C12 1.5211(17) . ?
C12 C13 1.5356(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.4988(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O2 H2 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 103.21(10) . . ?
C5 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
C5 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.1 . . ?
C1 C2 C3 104.08(10) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C2 105.04(11) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
O2 C4 C3 108.90(10) . . ?
O2 C4 C5 119.34(10) . . ?
C3 C4 C5 105.19(10) . . ?
O2 C4 C7 117.48(10) . . ?
C3 C4 C7 114.54(10) . . ?
C5 C4 C7 90.02(9) . . ?
C1 C5 C6 115.06(10) . . ?
C1 C5 C4 106.98(10) . . ?
C6 C5 C4 89.67(9) . . ?
C1 C5 H5 114.2 . . ?
C6 C5 H5 114.2 . . ?
C4 C5 H5 114.2 . . ?
C14 C6 C7 115.52(10) . . ?
C14 C6 C5 112.38(10) . . ?
C7 C6 C5 90.50(9) . . ?
C14 C6 H6 112.2 . . ?
C7 C6 H6 112.2 . . ?
C5 C6 H6 112.2 . . ?
C8 C7 C6 115.94(10) . . ?
C8 C7 C4 115.52(11) . . ?
C6 C7 C4 89.57(9) . . ?
C8 C7 H7 111.4 . . ?
C6 C7 H7 111.4 . . ?
C4 C7 H7 111.4 . . ?
C9 C8 C7 123.63(11) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C8 C9 C10 119.80(11) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C14 C10 C11 109.16(11) . . ?
C14 C10 C9 122.59(12) . . ?
C11 C10 C9 128.16(11) . . ?
O1 C11 C10 127.08(11) . . ?
O1 C11 C12 124.94(11) . . ?
C10 C11 C12 107.96(10) . . ?
C11 C12 C13 105.64(10) . . ?
C11 C12 H12A 110.6 . . ?
C13 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
C13 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 C12 103.60(10) . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C10 C14 C6 122.38(11) . . ?
C10 C14 C13 113.52(11) . . ?
C6 C14 C13 123.97(11) . . ?
C4 O2 H2 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 -38.96(13) . . . . ?
C1 C2 C3 C4 36.76(13) . . . . ?
C2 C3 C4 O2 -148.81(11) . . . . ?
C2 C3 C4 C5 -19.79(13) . . . . ?
C2 C3 C4 C7 77.36(13) . . . . ?
C2 C1 C5 C6 -71.28(13) . . . . ?
C2 C1 C5 C4 26.55(13) . . . . ?
O2 C4 C5 C1 118.22(11) . . . . ?
C3 C4 C5 C1 -4.30(13) . . . . ?
C7 C4 C5 C1 -119.80(10) . . . . ?
O2 C4 C5 C6 -125.60(10) . . . . ?
C3 C4 C5 C6 111.87(10) . . . . ?
C7 C4 C5 C6 -3.62(9) . . . . ?
C1 C5 C6 C14 -129.70(11) . . . . ?
C4 C5 C6 C14 121.65(10) . . . . ?
C1 C5 C6 C7 112.29(11) . . . . ?
C4 C5 C6 C7 3.64(9) . . . . ?
C14 C6 C7 C8 -0.46(15) . . . . ?
C5 C6 C7 C8 114.76(11) . . . . ?
C14 C6 C7 C4 -118.86(11) . . . . ?
C5 C6 C7 C4 -3.63(9) . . . . ?
O2 C4 C7 C8 8.40(16) . . . . ?
C3 C4 C7 C8 138.10(12) . . . . ?
C5 C4 C7 C8 -115.14(11) . . . . ?
O2 C4 C7 C6 127.16(11) . . . . ?
C3 C4 C7 C6 -103.13(11) . . . . ?
C5 C4 C7 C6 3.62(9) . . . . ?
C6 C7 C8 C9 -0.45(18) . . . . ?
C4 C7 C8 C9 102.44(15) . . . . ?
C7 C8 C9 C10 -0.91(19) . . . . ?
C8 C9 C10 C14 3.53(19) . . . . ?
C8 C9 C10 C11 -172.70(12) . . . . ?
C14 C10 C11 O1 -175.58(12) . . . . ?
C9 C10 C11 O1 1.1(2) . . . . ?
C14 C10 C11 C12 2.77(14) . . . . ?
C9 C10 C11 C12 179.40(12) . . . . ?
O1 C11 C12 C13 177.60(12) . . . . ?
C10 C11 C12 C13 -0.79(13) . . . . ?
C11 C12 C13 C14 -1.23(13) . . . . ?
C11 C10 C14 C6 172.25(11) . . . . ?
C9 C10 C14 C6 -4.61(19) . . . . ?
C11 C10 C14 C13 -3.77(15) . . . . ?
C9 C10 C14 C13 179.37(11) . . . . ?
C7 C6 C14 C10 2.97(17) . . . . ?
C5 C6 C14 C10 -98.98(14) . . . . ?
C7 C6 C14 C13 178.58(11) . . . . ?
C5 C6 C14 C13 76.62(15) . . . . ?
C12 C13 C14 C10 3.14(14) . . . . ?
C12 C13 C14 C6 -172.81(11) . . . . ?

_refine_diff_density_max         0.957
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_fred25b
_database_code_depnum_ccdc_archive 'CCDC 1816389'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 O2'
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   14.4406(13)
_cell_length_b                   9.5463(9)
_cell_length_c                   10.3489(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.2686(11)
_cell_angle_gamma                90
_cell_volume                     1411.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    7298
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      29.14

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      0.7121
_exptl_crystal_density_method    0.7459
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7121
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17042
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_max         29.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3695
_reflns_number_gt                3231
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+0.4565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3695
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60445(7) 0.19587(10) 0.96330(9) 0.0134(2) Uani 1 1 d . . . . .
C2 C 0.49949(7) 0.19724(11) 0.97040(11) 0.0182(2) Uani 1 1 d . . . . .
H2A H 0.4873 0.2192 1.0599 0.022 Uiso 1 1 calc R U . . .
H2B H 0.4707 0.1057 0.9435 0.022 Uiso 1 1 calc R U . . .
C3 C 0.46135(7) 0.31399(11) 0.87374(11) 0.0198(2) Uani 1 1 d . . . . .
H3A H 0.4105 0.3662 0.9072 0.024 Uiso 1 1 calc R U . . .
H3B H 0.4365 0.2735 0.7876 0.024 Uiso 1 1 calc R U . . .
C4 C 0.54547(7) 0.41259(11) 0.86170(10) 0.0173(2) Uani 1 1 d . . . . .
H4A H 0.5600 0.4130 0.7711 0.021 Uiso 1 1 calc R U . . .
H4B H 0.5313 0.5096 0.8865 0.021 Uiso 1 1 calc R U . . .
C5 C 0.62818(7) 0.35298(10) 0.95609(9) 0.01414(19) Uani 1 1 d . . . . .
H5 H 0.6265 0.3951 1.0442 0.017 Uiso 1 1 calc R U . . .
C6 C 0.72413(7) 0.38322(11) 0.91637(10) 0.0167(2) Uani 1 1 d . . . . .
H6A H 0.7239 0.3492 0.8260 0.020 Uiso 1 1 calc R U . . .
H6B H 0.7329 0.4860 0.9154 0.020 Uiso 1 1 calc R U . . .
C7 C 0.80703(7) 0.31989(10) 1.00095(10) 0.0152(2) Uani 1 1 d . . . . .
C8 C 0.89375(7) 0.40899(11) 1.03172(11) 0.0194(2) Uani 1 1 d . . . . .
H8A H 0.8807 0.4935 1.0815 0.023 Uiso 1 1 calc R U . . .
H8B H 0.9171 0.4385 0.9506 0.023 Uiso 1 1 calc R U . . .
C9 C 0.96461(8) 0.31479(12) 1.11341(13) 0.0243(2) Uani 1 1 d . . . . .
H9A H 1.0189 0.2963 1.0673 0.029 Uiso 1 1 calc R U . . .
H9B H 0.9873 0.3589 1.1987 0.029 Uiso 1 1 calc R U . . .
C10 C 0.91231(7) 0.17974(11) 1.13231(11) 0.0187(2) Uani 1 1 d . . . . .
C11 C 0.81764(7) 0.18926(10) 1.05385(9) 0.0137(2) Uani 1 1 d . . . . .
C12 C 0.74222(7) 0.07520(10) 1.03599(9) 0.01312(19) Uani 1 1 d . . . . .
C13 C 0.76689(7) -0.06240(10) 1.10957(10) 0.0174(2) Uani 1 1 d . . . . .
H13A H 0.7085 -0.1135 1.1187 0.021 Uiso 1 1 calc R U . . .
H13B H 0.7992 -0.0410 1.1984 0.021 Uiso 1 1 calc R U . . .
C14 C 0.83002(8) -0.15657(11) 1.03922(11) 0.0213(2) Uani 1 1 d . . . . .
H14A H 0.8915 -0.1105 1.0398 0.026 Uiso 1 1 calc R U . . .
H14B H 0.8406 -0.2464 1.0869 0.026 Uiso 1 1 calc R U . . .
C15 C 0.78671(8) -0.18595(12) 0.89775(12) 0.0241(2) Uani 1 1 d . . . . .
H15A H 0.8287 -0.2478 0.8559 0.029 Uiso 1 1 calc R U . . .
H15B H 0.7261 -0.2347 0.8966 0.029 Uiso 1 1 calc R U . . .
C16 C 0.77152(7) -0.04840(12) 0.82121(11) 0.0203(2) Uani 1 1 d . . . . .
H16A H 0.8326 -0.0039 0.8146 0.024 Uiso 1 1 calc R U . . .
H16B H 0.7395 -0.0672 0.7318 0.024 Uiso 1 1 calc R U . . .
C17 C 0.71310(7) 0.04723(10) 0.89075(10) 0.0147(2) Uani 1 1 d . . . . .
C18 C 0.63371(7) 0.11445(11) 0.85072(10) 0.0156(2) Uani 1 1 d . . . . .
H18 H 0.6004 0.1118 0.7646 0.019 Uiso 1 1 calc R U . . .
O1 O 0.65752(5) 0.13134(7) 1.07652(7) 0.01385(16) Uani 1 1 d . . . . .
O2 O 0.94507(6) 0.08316(9) 1.20146(9) 0.0294(2) 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 O1 1.4427(11) . ?
C1 C18 1.5105(13) . ?
C1 C2 1.5281(14) . ?
C1 C5 1.5427(14) . ?
C2 C3 1.5452(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5558(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5392(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5283(14) . ?
C5 H5 1.0000 . ?
C6 C7 1.5044(14) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C11 1.3617(14) . ?
C7 C8 1.5094(14) . ?
C8 C9 1.5237(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5210(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O2 1.2201(14) . ?
C10 C11 1.4890(14) . ?
C11 C12 1.5323(14) . ?
C12 O1 1.4516(11) . ?
C12 C17 1.5250(14) . ?
C12 C13 1.5344(13) . ?
C13 C14 1.5362(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5330(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5329(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.4958(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.3271(14) . ?
C18 H18 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
O1 C1 C18 103.41(7) . . ?
O1 C1 C2 112.29(8) . . ?
C18 C1 C2 115.52(8) . . ?
O1 C1 C5 111.02(8) . . ?
C18 C1 C5 111.98(8) . . ?
C2 C1 C5 102.87(8) . . ?
C1 C2 C3 103.81(8) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C2 C3 C4 106.17(8) . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
C4 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C3 105.61(8) . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
C6 C5 C4 114.23(8) . . ?
C6 C5 C1 114.39(8) . . ?
C4 C5 C1 103.45(8) . . ?
C6 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C1 C5 H5 108.2 . . ?
C7 C6 C5 116.36(8) . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C11 C7 C6 129.49(9) . . ?
C11 C7 C8 112.91(9) . . ?
C6 C7 C8 117.58(9) . . ?
C7 C8 C9 104.78(9) . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C9 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C8 105.38(9) . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
O2 C10 C11 127.89(10) . . ?
O2 C10 C9 123.93(10) . . ?
C11 C10 C9 108.19(9) . . ?
C7 C11 C10 108.45(9) . . ?
C7 C11 C12 124.43(9) . . ?
C10 C11 C12 127.10(9) . . ?
O1 C12 C17 103.01(7) . . ?
O1 C12 C11 108.46(8) . . ?
C17 C12 C11 109.50(8) . . ?
O1 C12 C13 108.53(8) . . ?
C17 C12 C13 110.53(8) . . ?
C11 C12 C13 115.99(8) . . ?
C12 C13 C14 112.15(9) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 111.79(9) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 110.19(9) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 108.84(9) . . ?
C17 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C18 C17 C16 131.80(10) . . ?
C18 C17 C12 109.05(9) . . ?
C16 C17 C12 119.10(9) . . ?
C17 C18 C1 109.44(9) . . ?
C17 C18 H18 125.3 . . ?
C1 C18 H18 125.3 . . ?
C1 O1 C12 107.11(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 159.47(8) . . . . ?
C18 C1 C2 C3 -82.27(10) . . . . ?
C5 C1 C2 C3 40.04(10) . . . . ?
C1 C2 C3 C4 -23.33(11) . . . . ?
C2 C3 C4 C5 -2.31(11) . . . . ?
C3 C4 C5 C6 151.77(9) . . . . ?
C3 C4 C5 C1 26.80(10) . . . . ?
O1 C1 C5 C6 73.24(10) . . . . ?
C18 C1 C5 C6 -41.79(11) . . . . ?
C2 C1 C5 C6 -166.46(8) . . . . ?
O1 C1 C5 C4 -161.90(8) . . . . ?
C18 C1 C5 C4 83.08(9) . . . . ?
C2 C1 C5 C4 -41.59(9) . . . . ?
C4 C5 C6 C7 -176.46(8) . . . . ?
C1 C5 C6 C7 -57.51(12) . . . . ?
C5 C6 C7 C11 42.54(15) . . . . ?
C5 C6 C7 C8 -139.16(10) . . . . ?
C11 C7 C8 C9 0.51(12) . . . . ?
C6 C7 C8 C9 -178.07(9) . . . . ?
C7 C8 C9 C10 -3.57(12) . . . . ?
C8 C9 C10 O2 -174.36(11) . . . . ?
C8 C9 C10 C11 5.33(12) . . . . ?
C6 C7 C11 C10 -178.74(10) . . . . ?
C8 C7 C11 C10 2.90(12) . . . . ?
C6 C7 C11 C12 -0.06(17) . . . . ?
C8 C7 C11 C12 -178.42(9) . . . . ?
O2 C10 C11 C7 174.50(11) . . . . ?
C9 C10 C11 C7 -5.18(12) . . . . ?
O2 C10 C11 C12 -4.14(18) . . . . ?
C9 C10 C11 C12 176.19(9) . . . . ?
C7 C11 C12 O1 -54.74(12) . . . . ?
C10 C11 C12 O1 123.70(10) . . . . ?
C7 C11 C12 C17 56.97(12) . . . . ?
C10 C11 C12 C17 -124.59(10) . . . . ?
C7 C11 C12 C13 -177.11(9) . . . . ?
C10 C11 C12 C13 1.32(14) . . . . ?
O1 C12 C13 C14 158.19(8) . . . . ?
C17 C12 C13 C14 45.92(11) . . . . ?
C11 C12 C13 C14 -79.47(11) . . . . ?
C12 C13 C14 C15 -55.18(12) . . . . ?
C13 C14 C15 C16 60.05(12) . . . . ?
C14 C15 C16 C17 -55.61(12) . . . . ?
C15 C16 C17 C18 -125.86(12) . . . . ?
C15 C16 C17 C12 51.48(12) . . . . ?
O1 C12 C17 C18 15.42(10) . . . . ?
C11 C12 C17 C18 -99.83(10) . . . . ?
C13 C12 C17 C18 131.19(9) . . . . ?
O1 C12 C17 C16 -162.48(9) . . . . ?
C11 C12 C17 C16 82.27(11) . . . . ?
C13 C12 C17 C16 -46.71(12) . . . . ?
C16 C17 C18 C1 179.17(10) . . . . ?
C12 C17 C18 C1 1.64(11) . . . . ?
O1 C1 C18 C17 -18.21(11) . . . . ?
C2 C1 C18 C17 -141.29(9) . . . . ?
C5 C1 C18 C17 101.39(10) . . . . ?
C18 C1 O1 C12 27.87(9) . . . . ?
C2 C1 O1 C12 153.07(8) . . . . ?
C5 C1 O1 C12 -92.39(9) . . . . ?
C17 C12 O1 C1 -26.84(9) . . . . ?
C11 C12 O1 C1 89.16(9) . . . . ?
C13 C12 O1 C1 -144.03(8) . . . . ?

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_fred28
_database_code_depnum_ccdc_archive 'CCDC 1816386'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   6.5568(4)
_cell_length_b                   15.0022(10)
_cell_length_c                   11.4025(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.5881(8)
_cell_angle_gamma                90
_cell_volume                     1111.80(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6992
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      29.32

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.195
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13557
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.256
_diffrn_reflns_theta_max         29.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2910
_reflns_number_gt                2630
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.4182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2910
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66441(16) 0.62429(7) 0.61498(9) 0.0207(2) Uani 1 1 d . . . . .
H1A H 0.5582 0.5804 0.6300 0.025 Uiso 1 1 calc R U . . .
H1B H 0.6026 0.6846 0.6098 0.025 Uiso 1 1 calc R U . . .
C2 C 0.85168(18) 0.62018(9) 0.71224(10) 0.0277(3) Uani 1 1 d . . . . .
H2A H 0.8673 0.5596 0.7467 0.033 Uiso 1 1 calc R U . . .
H2B H 0.8358 0.6632 0.7762 0.033 Uiso 1 1 calc R U . . .
C3 C 1.04025(17) 0.64463(8) 0.64964(10) 0.0254(2) Uani 1 1 d . . . . .
H3A H 1.1054 0.7002 0.6832 0.030 Uiso 1 1 calc R U . . .
H3B H 1.1436 0.5962 0.6593 0.030 Uiso 1 1 calc R U . . .
C4 C 0.95693(14) 0.65743(7) 0.51838(8) 0.0169(2) Uani 1 1 d . . . . .
C5 C 0.91732(15) 0.75263(7) 0.47747(9) 0.0189(2) Uani 1 1 d . . . . .
H5 H 0.8585 0.7978 0.5207 0.023 Uiso 1 1 calc R U . . .
C6 C 0.97758(15) 0.76297(7) 0.37194(9) 0.0194(2) Uani 1 1 d . . . . .
H6 H 0.9712 0.8168 0.3278 0.023 Uiso 1 1 calc R U . . .
C7 C 1.05854(15) 0.67449(7) 0.33339(9) 0.0172(2) Uani 1 1 d . . . . .
H7 H 1.1860 0.6832 0.2953 0.021 Uiso 1 1 calc R U . . .
C8 C 0.89552(15) 0.62625(6) 0.25126(9) 0.0158(2) Uani 1 1 d . . . . .
C9 C 0.92413(15) 0.60027(6) 0.13028(9) 0.0172(2) Uani 1 1 d . . . . .
C10 C 0.73478(16) 0.54915(7) 0.07644(9) 0.0195(2) Uani 1 1 d . . . . .
H10A H 0.7713 0.4874 0.0567 0.023 Uiso 1 1 calc R U . . .
H10B H 0.6687 0.5789 0.0037 0.023 Uiso 1 1 calc R U . . .
C11 C 0.59150(15) 0.54952(7) 0.17265(9) 0.0179(2) Uani 1 1 d . . . . .
H11A H 0.4603 0.5799 0.1441 0.021 Uiso 1 1 calc R U . . .
H11B H 0.5612 0.4879 0.1962 0.021 Uiso 1 1 calc R U . . .
C12 C 0.70808(14) 0.59965(6) 0.27533(8) 0.01516(19) Uani 1 1 d . . . . .
C13 C 0.61363(15) 0.61654(6) 0.38652(9) 0.0165(2) Uani 1 1 d . . . . .
H13A H 0.4921 0.5773 0.3861 0.020 Uiso 1 1 calc R U . . .
H13B H 0.5643 0.6789 0.3852 0.020 Uiso 1 1 calc R U . . .
C14 C 0.75700(15) 0.60124(6) 0.50228(8) 0.0162(2) Uani 1 1 d . . . . .
H14 H 0.7966 0.5368 0.5062 0.019 Uiso 1 1 calc R U . . .
O1 O 1.10345(11) 0.62646(5) 0.44336(6) 0.01840(17) Uani 1 1 d . . . . .
O2 O 1.07504(13) 0.61735(5) 0.08111(7) 0.02508(19) 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 C14 1.5316(13) . ?
C1 C2 1.5432(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5510(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5361(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.4449(11) . ?
C4 C5 1.5141(14) . ?
C4 C14 1.5490(13) . ?
C5 C6 1.3243(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.5162(14) . ?
C6 H6 0.9500 . ?
C7 O1 1.4425(12) . ?
C7 C8 1.5096(13) . ?
C7 H7 1.0000 . ?
C8 C12 1.3543(13) . ?
C8 C9 1.4691(13) . ?
C9 O2 1.2270(13) . ?
C9 C10 1.5182(14) . ?
C10 C11 1.5358(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5114(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5042(13) . ?
C13 C14 1.5333(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14 1.0000 . ?

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
C14 C1 C2 103.18(8) . . ?
C14 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
C14 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.1 . . ?
C1 C2 C3 105.48(9) . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
C4 C3 C2 105.98(9) . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
O1 C4 C5 102.79(8) . . ?
O1 C4 C3 110.97(8) . . ?
C5 C4 C3 116.27(9) . . ?
O1 C4 C14 111.92(8) . . ?
C5 C4 C14 111.64(8) . . ?
C3 C4 C14 103.53(8) . . ?
C6 C5 C4 109.32(9) . . ?
C6 C5 H5 125.3 . . ?
C4 C5 H5 125.3 . . ?
C5 C6 C7 108.59(9) . . ?
C5 C6 H6 125.7 . . ?
C7 C6 H6 125.7 . . ?
O1 C7 C8 110.26(8) . . ?
O1 C7 C6 102.97(8) . . ?
C8 C7 C6 110.69(8) . . ?
O1 C7 H7 110.9 . . ?
C8 C7 H7 110.9 . . ?
C6 C7 H7 110.9 . . ?
C12 C8 C9 110.12(9) . . ?
C12 C8 C7 127.06(9) . . ?
C9 C8 C7 122.81(8) . . ?
O2 C9 C8 125.75(10) . . ?
O2 C9 C10 125.90(9) . . ?
C8 C9 C10 108.34(8) . . ?
C9 C10 C11 104.72(8) . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
C12 C11 C10 105.11(8) . . ?
C12 C11 H11A 110.7 . . ?
C10 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C8 C12 C13 127.36(9) . . ?
C8 C12 C11 111.67(8) . . ?
C13 C12 C11 120.95(8) . . ?
C12 C13 C14 115.25(8) . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C1 C14 C13 115.00(8) . . ?
C1 C14 C4 101.58(8) . . ?
C13 C14 C4 115.70(8) . . ?
C1 C14 H14 108.0 . . ?
C13 C14 H14 108.0 . . ?
C4 C14 H14 108.0 . . ?
C7 O1 C4 106.18(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 28.84(11) . . . . ?
C1 C2 C3 C4 -2.64(12) . . . . ?
C2 C3 C4 O1 -144.48(9) . . . . ?
C2 C3 C4 C5 98.55(11) . . . . ?
C2 C3 C4 C14 -24.26(11) . . . . ?
O1 C4 C5 C6 18.05(10) . . . . ?
C3 C4 C5 C6 139.47(9) . . . . ?
C14 C4 C5 C6 -102.07(10) . . . . ?
C4 C5 C6 C7 1.08(11) . . . . ?
C5 C6 C7 O1 -19.85(10) . . . . ?
C5 C6 C7 C8 97.98(10) . . . . ?
O1 C7 C8 C12 53.48(13) . . . . ?
C6 C7 C8 C12 -59.79(13) . . . . ?
O1 C7 C8 C9 -125.64(9) . . . . ?
C6 C7 C8 C9 121.09(10) . . . . ?
C12 C8 C9 O2 177.52(10) . . . . ?
C7 C8 C9 O2 -3.23(16) . . . . ?
C12 C8 C9 C10 -2.21(11) . . . . ?
C7 C8 C9 C10 177.04(9) . . . . ?
O2 C9 C10 C11 -178.09(10) . . . . ?
C8 C9 C10 C11 1.63(10) . . . . ?
C9 C10 C11 C12 -0.58(10) . . . . ?
C9 C8 C12 C13 -176.91(9) . . . . ?
C7 C8 C12 C13 3.88(16) . . . . ?
C9 C8 C12 C11 1.86(11) . . . . ?
C7 C8 C12 C11 -177.35(9) . . . . ?
C10 C11 C12 C8 -0.76(11) . . . . ?
C10 C11 C12 C13 178.09(8) . . . . ?
C8 C12 C13 C14 -44.82(14) . . . . ?
C11 C12 C13 C14 136.52(9) . . . . ?
C2 C1 C14 C13 -169.41(9) . . . . ?
C2 C1 C14 C4 -43.68(10) . . . . ?
C12 C13 C14 C1 176.24(8) . . . . ?
C12 C13 C14 C4 58.20(11) . . . . ?
O1 C4 C14 C1 161.66(8) . . . . ?
C5 C4 C14 C1 -83.74(9) . . . . ?
C3 C4 C14 C1 42.08(9) . . . . ?
O1 C4 C14 C13 -73.07(10) . . . . ?
C5 C4 C14 C13 41.52(11) . . . . ?
C3 C4 C14 C13 167.35(8) . . . . ?
C8 C7 O1 C4 -87.03(9) . . . . ?
C6 C7 O1 C4 31.10(9) . . . . ?
C5 C4 O1 C7 -30.42(9) . . . . ?
C3 C4 O1 C7 -155.39(8) . . . . ?
C14 C4 O1 C7 89.51(9) . . . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_fred40
_database_code_depnum_ccdc_archive 'CCDC 1816384'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 O2'
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.7545(5)
_cell_length_b                   9.4518(5)
_cell_length_c                   15.7484(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.8550(10)
_cell_angle_gamma                90
_cell_volume                     1409.72(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    8868
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.35

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.243
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16771
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3466
_reflns_number_gt                3165
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+0.5671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3466
_refine_ls_number_parameters     185
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.053
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16104(11) 0.64032(13) 0.57037(7) 0.0191(2) Uani 1 1 d . . . . .
C2 C 0.15535(13) 0.50293(14) 0.61991(8) 0.0243(3) Uani 1 1 d . . . . .
H2A H 0.056682 0.478244 0.619821 0.029 Uiso 1 1 calc R U . . .
H2B H 0.210760 0.511063 0.681210 0.029 Uiso 1 1 calc R U . . .
C3 C 0.21963(13) 0.39194(13) 0.57054(8) 0.0227(2) Uani 1 1 d . . . . .
H3A H 0.301206 0.344965 0.610031 0.027 Uiso 1 1 calc R U . . .
H3B H 0.148826 0.319210 0.544770 0.027 Uiso 1 1 calc R U . . .
C4 C 0.26597(11) 0.47334(12) 0.49985(7) 0.0172(2) Uani 1 1 d . . . . .
C5 C 0.24080(11) 0.61424(12) 0.50280(7) 0.0160(2) Uani 1 1 d . . . . .
C6 C 0.32760(12) 0.39258(12) 0.43553(7) 0.0192(2) Uani 1 1 d . . . . .
H6A H 0.314396 0.290100 0.443863 0.023 Uiso 1 1 calc R U . . .
H6B H 0.430411 0.411070 0.448366 0.023 Uiso 1 1 calc R U . . .
C7 C 0.26224(12) 0.43035(12) 0.33957(7) 0.0181(2) Uani 1 1 d . . . . .
H7 H 0.158060 0.413341 0.325702 0.022 Uiso 1 1 calc R U . . .
C8 C 0.32939(13) 0.34253(13) 0.27737(8) 0.0246(3) Uani 1 1 d D . . . .
H8A H 0.369259 0.253019 0.305437 0.029 Uiso 1 1 calc R U . A 1
H8B H 0.258920 0.320267 0.222451 0.029 Uiso 1 1 calc R U . A 1
C9A C 0.44625(15) 0.43854(15) 0.25961(9) 0.0256(3) Uani 0.882(3) 1 d D . P B 1
H9A1 H 0.530988 0.436310 0.308970 0.031 Uiso 0.882(3) 1 calc R U P B 1
H9A2 H 0.473284 0.410327 0.205307 0.031 Uiso 0.882(3) 1 calc R U P B 1
C9B C 0.3550(11) 0.4339(10) 0.2107(7) 0.0256(3) Uani 0.118(3) 1 d D . P B 2
H9B1 H 0.273151 0.433274 0.159466 0.031 Uiso 0.118(3) 1 calc R U P B 2
H9B2 H 0.439622 0.402445 0.191613 0.031 Uiso 0.118(3) 1 calc R U P B 2
C10 C 0.37800(14) 0.58302(14) 0.25025(8) 0.0264(3) Uani 1 1 d D . . . .
H10A H 0.315482 0.594935 0.191103 0.032 Uiso 1 1 calc R U . B 1
H10B H 0.450634 0.658326 0.260058 0.032 Uiso 1 1 calc R U . B 1
C11 C 0.29239(12) 0.58930(12) 0.32017(7) 0.0178(2) Uani 1 1 d . . . . .
C12 C 0.16345(12) 0.68345(13) 0.29854(7) 0.0203(2) Uani 1 1 d . . . . .
H12 H 0.096422 0.685355 0.243732 0.024 Uiso 1 1 calc R U . . .
C13 C 0.15708(11) 0.76316(12) 0.36695(7) 0.0174(2) Uani 1 1 d . . . . .
C14 C 0.28197(11) 0.72468(11) 0.44235(7) 0.0152(2) Uani 1 1 d . . . . .
C15 C 0.35735(12) 0.85688(12) 0.48913(8) 0.0195(2) Uani 1 1 d . . . . .
H15A H 0.409713 0.829469 0.548760 0.023 Uiso 1 1 calc R U . . .
H15B H 0.427345 0.889784 0.457206 0.023 Uiso 1 1 calc R U . . .
C16 C 0.25859(13) 0.98053(12) 0.49632(8) 0.0239(3) Uani 1 1 d . . . . .
H16A H 0.204036 0.956624 0.539899 0.029 Uiso 1 1 calc R U . . .
H16B H 0.315964 1.065533 0.517431 0.029 Uiso 1 1 calc R U . . .
C17 C 0.15611(13) 1.01426(12) 0.40882(9) 0.0249(3) Uani 1 1 d . . . . .
H17A H 0.209877 1.040735 0.365275 0.030 Uiso 1 1 calc R U . . .
H17B H 0.095781 1.095454 0.416032 0.030 Uiso 1 1 calc R U . . .
C18 C 0.06295(12) 0.88464(13) 0.37596(8) 0.0220(2) Uani 1 1 d . . . . .
H18A H 0.005686 0.860326 0.417986 0.026 Uiso 1 1 calc R U . . .
H18B H -0.001975 0.905870 0.318735 0.026 Uiso 1 1 calc R U . . .
O1 O 0.10440(10) 0.75058(10) 0.58362(6) 0.0274(2) Uani 1 1 d . . . . .
O2 O 0.37771(8) 0.65565(8) 0.39802(5) 0.01690(18) 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 O1 1.2207(15) . ?
C1 C5 1.4815(15) . ?
C1 C2 1.5228(17) . ?
C2 C3 1.5270(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5087(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.3570(15) . ?
C4 C6 1.5040(15) . ?
C5 C14 1.5299(15) . ?
C6 C7 1.5350(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5442(15) . ?
C7 C11 1.5748(16) . ?
C7 H7 1.0000 . ?
C8 C9B 1.427(10) . ?
C8 C9A 1.5342(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9A C10 1.5109(19) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C9B C10 1.535(10) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10 C11 1.5342(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O2 1.4492(13) . ?
C11 C12 1.5115(16) . ?
C12 C13 1.3282(16) . ?
C12 H12 0.9500 . ?
C13 C18 1.4980(16) . ?
C13 C14 1.5276(14) . ?
C14 O2 1.4483(12) . ?
C14 C15 1.5444(15) . ?
C15 C16 1.5359(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5299(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5393(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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 C5 127.01(11) . . ?
O1 C1 C2 124.53(10) . . ?
C5 C1 C2 108.42(10) . . ?
C1 C2 C3 104.78(9) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C4 C3 C2 104.92(9) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
C5 C4 C6 128.75(10) . . ?
C5 C4 C3 112.74(10) . . ?
C6 C4 C3 118.48(10) . . ?
C4 C5 C1 108.56(10) . . ?
C4 C5 C14 124.87(10) . . ?
C1 C5 C14 126.49(10) . . ?
C4 C6 C7 113.97(9) . . ?
C4 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C4 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 111.11(10) . . ?
C6 C7 C11 111.10(9) . . ?
C8 C7 C11 105.22(9) . . ?
C6 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
C11 C7 H7 109.8 . . ?
C9B C8 C7 108.5(4) . . ?
C9A C8 C7 104.13(10) . . ?
C9A C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C9A C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9A C8 102.89(10) . . ?
C10 C9A H9A1 111.2 . . ?
C8 C9A H9A1 111.2 . . ?
C10 C9A H9A2 111.2 . . ?
C8 C9A H9A2 111.2 . . ?
H9A1 C9A H9A2 109.1 . . ?
C8 C9B C10 107.0(6) . . ?
C8 C9B H9B1 110.3 . . ?
C10 C9B H9B1 110.3 . . ?
C8 C9B H9B2 110.3 . . ?
C10 C9B H9B2 110.3 . . ?
H9B1 C9B H9B2 108.6 . . ?
C9A C10 C11 105.53(10) . . ?
C11 C10 C9B 105.9(4) . . ?
C9A C10 H10A 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C9A C10 H10B 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
O2 C11 C12 102.37(9) . . ?
O2 C11 C10 108.84(9) . . ?
C12 C11 C10 115.31(10) . . ?
O2 C11 C7 110.17(9) . . ?
C12 C11 C7 114.93(9) . . ?
C10 C11 C7 105.15(9) . . ?
C13 C12 C11 110.43(10) . . ?
C13 C12 H12 124.8 . . ?
C11 C12 H12 124.8 . . ?
C12 C13 C18 131.33(10) . . ?
C12 C13 C14 108.18(10) . . ?
C18 C13 C14 120.11(9) . . ?
O2 C14 C13 102.64(8) . . ?
O2 C14 C5 106.75(8) . . ?
C13 C14 C5 111.52(9) . . ?
O2 C14 C15 107.83(8) . . ?
C13 C14 C15 112.22(9) . . ?
C5 C14 C15 114.90(9) . . ?
C16 C15 C14 114.55(9) . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 112.23(10) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 110.04(10) . . ?
C16 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C13 C18 C17 108.43(9) . . ?
C13 C18 H18A 110.0 . . ?
C17 C18 H18A 110.0 . . ?
C13 C18 H18B 110.0 . . ?
C17 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C14 O2 C11 107.26(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 171.03(11) . . . . ?
C5 C1 C2 C3 -6.77(12) . . . . ?
C1 C2 C3 C4 3.36(12) . . . . ?
C2 C3 C4 C5 1.45(13) . . . . ?
C2 C3 C4 C6 -176.75(10) . . . . ?
C6 C4 C5 C1 172.13(10) . . . . ?
C3 C4 C5 C1 -5.83(13) . . . . ?
C6 C4 C5 C14 -4.85(18) . . . . ?
C3 C4 C5 C14 177.18(9) . . . . ?
O1 C1 C5 C4 -169.81(11) . . . . ?
C2 C1 C5 C4 7.92(12) . . . . ?
O1 C1 C5 C14 7.12(18) . . . . ?
C2 C1 C5 C14 -175.15(10) . . . . ?
C5 C4 C6 C7 -47.13(16) . . . . ?
C3 C4 C6 C7 130.73(10) . . . . ?
C4 C6 C7 C8 -179.43(9) . . . . ?
C4 C6 C7 C11 63.79(12) . . . . ?
C6 C7 C8 C9B -136.9(5) . . . . ?
C11 C7 C8 C9B -16.6(5) . . . . ?
C6 C7 C8 C9A -94.92(12) . . . . ?
C11 C7 C8 C9A 25.42(12) . . . . ?
C7 C8 C9A C10 -40.17(13) . . . . ?
C7 C8 C9B C10 28.2(7) . . . . ?
C8 C9A C10 C11 39.61(13) . . . . ?
C8 C9B C10 C11 -28.8(7) . . . . ?
C9A C10 C11 O2 94.51(11) . . . . ?
C9B C10 C11 O2 135.6(4) . . . . ?
C9A C10 C11 C12 -151.18(11) . . . . ?
C9B C10 C11 C12 -110.1(4) . . . . ?
C9A C10 C11 C7 -23.51(13) . . . . ?
C9B C10 C11 C7 17.6(4) . . . . ?
C6 C7 C11 O2 1.73(12) . . . . ?
C8 C7 C11 O2 -118.61(9) . . . . ?
C6 C7 C11 C12 -113.26(10) . . . . ?
C8 C7 C11 C12 126.40(10) . . . . ?
C6 C7 C11 C10 118.84(10) . . . . ?
C8 C7 C11 C10 -1.49(12) . . . . ?
O2 C11 C12 C13 -16.54(12) . . . . ?
C10 C11 C12 C13 -134.53(11) . . . . ?
C7 C11 C12 C13 102.88(11) . . . . ?
C11 C12 C13 C18 171.09(11) . . . . ?
C11 C12 C13 C14 -1.61(13) . . . . ?
C12 C13 C14 O2 19.18(11) . . . . ?
C18 C13 C14 O2 -154.49(9) . . . . ?
C12 C13 C14 C5 -94.77(11) . . . . ?
C18 C13 C14 C5 91.56(12) . . . . ?
C12 C13 C14 C15 134.68(10) . . . . ?
C18 C13 C14 C15 -38.99(14) . . . . ?
C4 C5 C14 O2 -12.75(14) . . . . ?
C1 C5 C14 O2 170.80(9) . . . . ?
C4 C5 C14 C13 98.62(12) . . . . ?
C1 C5 C14 C13 -77.83(13) . . . . ?
C4 C5 C14 C15 -132.23(11) . . . . ?
C1 C5 C14 C15 51.32(14) . . . . ?
O2 C14 C15 C16 148.64(10) . . . . ?
C13 C14 C15 C16 36.32(13) . . . . ?
C5 C14 C15 C16 -92.48(11) . . . . ?
C14 C15 C16 C17 -49.04(14) . . . . ?
C15 C16 C17 C18 60.37(13) . . . . ?
C12 C13 C18 C17 -121.94(14) . . . . ?
C14 C13 C18 C17 50.04(14) . . . . ?
C16 C17 C18 C13 -58.48(13) . . . . ?
C13 C14 O2 C11 -29.74(10) . . . . ?
C5 C14 O2 C11 87.65(9) . . . . ?
C15 C14 O2 C11 -148.38(9) . . . . ?
C12 C11 O2 C14 28.73(10) . . . . ?
C10 C11 O2 C14 151.23(9) . . . . ?
C7 C11 O2 C14 -93.97(10) . . . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_fred30c
_database_code_depnum_ccdc_archive 'CCDC 1816385'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8954(6)
_cell_length_b                   8.3622(8)
_cell_length_c                   12.1458(11)
_cell_angle_alpha                106.4923(11)
_cell_angle_beta                 92.7147(11)
_cell_angle_gamma                108.8989(10)
_cell_volume                     627.78(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    3078
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      29.04

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   0.7070
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7070
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6802
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.770
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2566
_reflns_number_gt                2170
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.2556P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2566
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36207(19) 0.59212(17) 0.78025(11) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.1678(2) 0.54625(19) 0.84024(13) 0.0346(3) Uani 1 1 d . . . . .
H2A H 0.0708 0.5996 0.8184 0.042 Uiso 1 1 calc R U . . .
H2B H 0.0969 0.4168 0.8171 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2428(2) 0.6220(2) 0.97123(14) 0.0446(4) Uani 1 1 d . . . . .
H3A H 0.2226 0.5255 1.0051 0.054 Uiso 1 1 calc R U . . .
H3B H 0.1665 0.6973 1.0093 0.054 Uiso 1 1 calc R U . . .
C4 C 0.4744(2) 0.73219(19) 0.98612(12) 0.0341(3) Uani 1 1 d . . . . .
H4A H 0.5100 0.8448 1.0495 0.041 Uiso 1 1 calc R U . . .
H4B H 0.5595 0.6660 1.0035 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5098(2) 0.76698(16) 0.87006(11) 0.0264(3) Uani 1 1 d . . . . .
H5 H 0.4578 0.8634 0.8675 0.032 Uiso 1 1 calc R U . . .
C6 C 0.74102(19) 0.83007(17) 0.85946(11) 0.0266(3) Uani 1 1 d . . . . .
H6A H 0.7949 0.7390 0.8691 0.032 Uiso 1 1 calc R U . . .
H6B H 0.8113 0.9385 0.9251 0.032 Uiso 1 1 calc R U . . .
C7 C 0.80639(19) 0.86990(16) 0.74844(11) 0.0251(3) Uani 1 1 d . . . . .
C8 C 0.79860(18) 0.71028(16) 0.64641(11) 0.0242(3) Uani 1 1 d . . . . .
C9 C 0.7164(2) 0.53336(17) 0.62444(11) 0.0276(3) Uani 1 1 d . . . . .
H9 H 0.7394 0.4667 0.5531 0.033 Uiso 1 1 calc R U . . .
C10 C 0.5974(2) 0.42458(17) 0.69085(12) 0.0299(3) Uani 1 1 d . . . . .
H10 H 0.6271 0.3207 0.6851 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4542(2) 0.44685(16) 0.75814(11) 0.0282(3) Uani 1 1 d . . . . .
H11 H 0.4047 0.3617 0.7964 0.034 Uiso 1 1 calc R U . . .
C12 C 1.0421(2) 0.98171(17) 0.76962(12) 0.0310(3) Uani 1 1 d . . . . .
H12A H 1.0676 1.1071 0.8119 0.037 Uiso 1 1 calc R U . . .
H12B H 1.1210 0.9364 0.8146 0.037 Uiso 1 1 calc R U . . .
C13 C 1.1042(2) 0.96134(18) 0.64814(12) 0.0328(3) Uani 1 1 d . . . . .
H13A H 1.0881 1.0549 0.6189 0.039 Uiso 1 1 calc R U . . .
H13B H 1.2482 0.9664 0.6490 0.039 Uiso 1 1 calc R U . . .
C14 C 0.9555(2) 0.77967(18) 0.57490(12) 0.0282(3) Uani 1 1 d . . . . .
C15 C 0.6868(2) 0.97564(18) 0.70849(13) 0.0325(3) Uani 1 1 d . . . . .
H15A H 0.7477 1.0153 0.6462 0.049 Uiso 1 1 calc R U . . .
H15B H 0.6947 1.0783 0.7733 0.049 Uiso 1 1 calc R U . . .
H15C H 0.5427 0.8999 0.6808 0.049 Uiso 1 1 calc R U . . .
O1 O 0.31615(15) 0.62606(12) 0.67508(8) 0.0320(2) Uani 1 1 d . . . . .
H1 H 0.2352 0.5329 0.6270 0.048 Uiso 1 1 calc R U . . .
O2 O 0.96775(15) 0.70355(13) 0.47481(8) 0.0363(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4277(15) . ?
C1 C11 1.5106(18) . ?
C1 C2 1.5463(18) . ?
C1 C5 1.5458(17) . ?
C2 C3 1.529(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.535(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.5332(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.5333(18) . ?
C5 H5 0.9900 . ?
C6 C7 1.5322(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.5259(17) . ?
C7 C15 1.5411(18) . ?
C7 C12 1.5561(17) . ?
C8 C9 1.3414(18) . ?
C8 C14 1.4933(18) . ?
C9 C10 1.4653(19) . ?
C9 H9 0.9400 . ?
C10 C11 1.3369(19) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C13 1.5341(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.5125(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 O2 1.2229(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
O1 H1 0.8300 . ?

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 C11 110.93(10) . . ?
O1 C1 C2 111.23(11) . . ?
C11 C1 C2 111.23(11) . . ?
O1 C1 C5 109.16(10) . . ?
C11 C1 C5 111.47(10) . . ?
C2 C1 C5 102.54(10) . . ?
C3 C2 C1 106.91(11) . . ?
C3 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 C4 105.87(11) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C3 105.72(11) . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
C4 C5 C6 111.51(11) . . ?
C4 C5 C1 102.80(10) . . ?
C6 C5 C1 118.73(10) . . ?
C4 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C1 C5 H5 107.8 . . ?
C5 C6 C7 118.97(11) . . ?
C5 C6 H6A 107.6 . . ?
C7 C6 H6A 107.6 . . ?
C5 C6 H6B 107.6 . . ?
C7 C6 H6B 107.6 . . ?
H6A C6 H6B 107.0 . . ?
C8 C7 C6 116.19(10) . . ?
C8 C7 C15 109.84(10) . . ?
C6 C7 C15 111.85(11) . . ?
C8 C7 C12 100.01(10) . . ?
C6 C7 C12 110.04(10) . . ?
C15 C7 C12 108.04(10) . . ?
C9 C8 C14 118.16(12) . . ?
C9 C8 C7 133.52(12) . . ?
C14 C8 C7 106.78(10) . . ?
C8 C9 C10 132.05(12) . . ?
C8 C9 H9 114.0 . . ?
C10 C9 H9 114.0 . . ?
C11 C10 C9 131.44(12) . . ?
C11 C10 H10 114.3 . . ?
C9 C10 H10 114.3 . . ?
C10 C11 C1 127.92(12) . . ?
C10 C11 H11 116.0 . . ?
C1 C11 H11 116.0 . . ?
C13 C12 C7 105.28(10) . . ?
C13 C12 H12A 110.7 . . ?
C7 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
C7 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C14 C13 C12 103.80(11) . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
O2 C14 C8 126.81(12) . . ?
O2 C14 C13 124.65(12) . . ?
C8 C14 C13 108.52(11) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -145.93(12) . . . . ?
C11 C1 C2 C3 89.88(14) . . . . ?
C5 C1 C2 C3 -29.38(14) . . . . ?
C1 C2 C3 C4 7.46(16) . . . . ?
C2 C3 C4 C5 17.78(16) . . . . ?
C3 C4 C5 C6 -164.29(12) . . . . ?
C3 C4 C5 C1 -36.02(14) . . . . ?
O1 C1 C5 C4 157.81(11) . . . . ?
C11 C1 C5 C4 -79.31(13) . . . . ?
C2 C1 C5 C4 39.77(13) . . . . ?
O1 C1 C5 C6 -78.60(14) . . . . ?
C11 C1 C5 C6 44.28(15) . . . . ?
C2 C1 C5 C6 163.37(11) . . . . ?
C4 C5 C6 C7 179.44(11) . . . . ?
C1 C5 C6 C7 60.26(16) . . . . ?
C5 C6 C7 C8 -83.69(14) . . . . ?
C5 C6 C7 C15 43.53(15) . . . . ?
C5 C6 C7 C12 163.62(11) . . . . ?
C6 C7 C8 C9 12.1(2) . . . . ?
C15 C7 C8 C9 -116.12(16) . . . . ?
C12 C7 C8 C9 130.43(15) . . . . ?
C6 C7 C8 C14 -152.97(11) . . . . ?
C15 C7 C8 C14 78.82(12) . . . . ?
C12 C7 C8 C14 -34.63(12) . . . . ?
C14 C8 C9 C10 164.99(13) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C8 C9 C10 C11 36.6(2) . . . . ?
C9 C10 C11 C1 3.9(2) . . . . ?
O1 C1 C11 C10 42.73(18) . . . . ?
C2 C1 C11 C10 167.09(13) . . . . ?
C5 C1 C11 C10 -79.14(17) . . . . ?
C8 C7 C12 C13 39.15(13) . . . . ?
C6 C7 C12 C13 161.94(11) . . . . ?
C15 C7 C12 C13 -75.68(13) . . . . ?
C7 C12 C13 C14 -29.17(13) . . . . ?
C9 C8 C14 O2 28.7(2) . . . . ?
C7 C8 C14 O2 -163.52(13) . . . . ?
C9 C8 C14 C13 -149.82(12) . . . . ?
C7 C8 C14 C13 17.93(13) . . . . ?
C12 C13 C14 O2 -171.38(13) . . . . ?
C12 C13 C14 C8 7.21(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.83 2.01 2.8393(14) 173.7 2_666
O1 H1 O2 0.83 2.01 2.8393(14) 173.7 2_666
O1 H1 O2 0.83 2.01 2.8393(14) 173.7 2_666
O1 H1 O2 0.83 2.01 2.8393(14) 173.7 2_666

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_fred15
_database_code_depnum_ccdc_archive 'CCDC 1816387'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   10.3761(13)
_cell_length_b                   10.8200(14)
_cell_length_c                   10.8988(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1223.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    5280
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.04

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   0.8656
_exptl_transmission_factor_max   0.9918
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8656
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14255
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         28.205
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3004
_reflns_number_gt                2789
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.2141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details unk
_refine_ls_abs_structure_Flack   0.4(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.13184(15) 1.04432(14) -0.04697(15) 0.0178(3) Uani 1 1 d . . . . .
H1 H 0.1647 0.9997 -0.1209 0.021 Uiso 1 1 calc R U . . .
C2 C 0.20091(17) 1.17007(16) -0.0415(2) 0.0271(4) Uani 1 1 d . . . . .
H2A H 0.1499 1.2302 0.0068 0.033 Uiso 1 1 calc R U . . .
H2B H 0.2142 1.2036 -0.1250 0.033 Uiso 1 1 calc R U . . .
C3 C 0.33212(16) 1.14404(15) 0.02174(17) 0.0213(3) Uani 1 1 d . . . . .
H3A H 0.4043 1.1620 -0.0349 0.026 Uiso 1 1 calc R U . . .
H3B H 0.3420 1.1958 0.0960 0.026 Uiso 1 1 calc R U . . .
C4 C 0.33019(16) 1.00544(14) 0.05621(17) 0.0199(3) Uani 1 1 d . . . . .
H4A H 0.3708 0.9544 -0.0085 0.024 Uiso 1 1 calc R U . . .
H4B H 0.3749 0.9906 0.1351 0.024 Uiso 1 1 calc R U . . .
C5 C 0.18629(15) 0.97847(13) 0.06658(16) 0.0161(3) Uani 1 1 d . . . . .
C6 C 0.12456(16) 1.02357(16) 0.18347(16) 0.0203(3) Uani 1 1 d . . . . .
H6 H 0.1443 1.0989 0.2241 0.024 Uiso 1 1 calc R U . . .
C7 C 0.03846(17) 0.94132(17) 0.22032(15) 0.0217(3) Uani 1 1 d . . . . .
H7 H -0.0146 0.9489 0.2910 0.026 Uiso 1 1 calc R U . . .
C8 C 0.03787(15) 0.83363(15) 0.13234(15) 0.0181(3) Uani 1 1 d . . . . .
H8 H 0.0405 0.7545 0.1796 0.022 Uiso 1 1 calc R U . . .
C9 C -0.07982(15) 0.83288(14) 0.04501(14) 0.0162(3) Uani 1 1 d . . . . .
H9 H -0.0859 0.7467 0.0123 0.019 Uiso 1 1 calc R U . . .
C10 C -0.08319(15) 0.91984(14) -0.06959(15) 0.0168(3) Uani 1 1 d . . . . .
C11 C -0.01512(15) 1.04683(15) -0.05560(16) 0.0184(3) Uani 1 1 d . . . . .
H11A H -0.0394 1.0990 -0.1265 0.022 Uiso 1 1 calc R U . . .
H11B H -0.0491 1.0875 0.0191 0.022 Uiso 1 1 calc R U . . .
C12 C -0.03225(18) 0.85143(18) -0.18255(16) 0.0239(4) Uani 1 1 d . . . . .
H12A H -0.0428 0.9037 -0.2553 0.036 Uiso 1 1 calc R U . . .
H12B H -0.0806 0.7744 -0.1936 0.036 Uiso 1 1 calc R U . . .
H12C H 0.0593 0.8324 -0.1710 0.036 Uiso 1 1 calc R U . . .
C13 C -0.23059(16) 0.94353(16) -0.08459(17) 0.0232(4) Uani 1 1 d . . . . .
H13A H -0.2459 1.0236 -0.1260 0.028 Uiso 1 1 calc R U . . .
H13B H -0.2706 0.8771 -0.1341 0.028 Uiso 1 1 calc R U . . .
C14 C -0.28748(17) 0.94508(17) 0.04482(19) 0.0264(4) Uani 1 1 d . . . . .
H14A H -0.2826 1.0289 0.0810 0.032 Uiso 1 1 calc R U . . .
H14B H -0.3785 0.9178 0.0441 0.032 Uiso 1 1 calc R U . . .
C15 C -0.20415(15) 0.85520(15) 0.11531(16) 0.0185(3) Uani 1 1 d . . . . .
O1 O -0.23028(12) 0.80871(12) 0.21361(12) 0.0251(3) Uani 1 1 d . . . . .
O2 O 0.15615(10) 0.84833(9) 0.06537(11) 0.0183(2) 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 C11 1.528(2) . ?
C1 C5 1.536(2) . ?
C1 C2 1.539(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.552(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.546(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O2 1.4425(18) . ?
C5 C6 1.507(2) . ?
C6 C7 1.323(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.509(2) . ?
C7 H7 0.9500 . ?
C8 O2 1.437(2) . ?
C8 C9 1.548(2) . ?
C8 H8 1.0000 . ?
C9 C15 1.520(2) . ?
C9 C10 1.564(2) . ?
C9 H9 1.0000 . ?
C10 C12 1.531(2) . ?
C10 C11 1.552(2) . ?
C10 C13 1.559(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.529(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.511(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O1 1.214(2) . ?

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
C11 C1 C5 115.15(14) . . ?
C11 C1 C2 116.84(14) . . ?
C5 C1 C2 101.97(13) . . ?
C11 C1 H1 107.4 . . ?
C5 C1 H1 107.4 . . ?
C2 C1 H1 107.4 . . ?
C1 C2 C3 105.40(13) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C4 C3 C2 105.82(13) . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C3 102.49(13) . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4B 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
O2 C5 C6 103.40(13) . . ?
O2 C5 C4 113.47(12) . . ?
C6 C5 C4 114.63(14) . . ?
O2 C5 C1 111.45(13) . . ?
C6 C5 C1 112.00(13) . . ?
C4 C5 C1 102.22(13) . . ?
C7 C6 C5 109.01(15) . . ?
C7 C6 H6 125.5 . . ?
C5 C6 H6 125.5 . . ?
C6 C7 C8 109.22(15) . . ?
C6 C7 H7 125.4 . . ?
C8 C7 H7 125.4 . . ?
O2 C8 C7 103.52(13) . . ?
O2 C8 C9 111.23(13) . . ?
C7 C8 C9 113.44(13) . . ?
O2 C8 H8 109.5 . . ?
C7 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C15 C9 C8 111.03(13) . . ?
C15 C9 C10 106.74(13) . . ?
C8 C9 C10 120.36(13) . . ?
C15 C9 H9 105.9 . . ?
C8 C9 H9 105.9 . . ?
C10 C9 H9 105.9 . . ?
C12 C10 C11 110.48(13) . . ?
C12 C10 C13 109.50(14) . . ?
C11 C10 C13 108.12(13) . . ?
C12 C10 C9 110.10(13) . . ?
C11 C10 C9 116.35(13) . . ?
C13 C10 C9 101.80(13) . . ?
C1 C11 C10 116.38(13) . . ?
C1 C11 H11A 108.2 . . ?
C10 C11 H11A 108.2 . . ?
C1 C11 H11B 108.2 . . ?
C10 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C10 106.48(14) . . ?
C14 C13 H13A 110.4 . . ?
C10 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
C10 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C15 C14 C13 103.94(14) . . ?
C15 C14 H14A 111.0 . . ?
C13 C14 H14A 111.0 . . ?
C15 C14 H14B 111.0 . . ?
C13 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
O1 C15 C14 125.97(15) . . ?
O1 C15 C9 124.65(15) . . ?
C14 C15 C9 109.37(14) . . ?
C8 O2 C5 106.77(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 156.08(15) . . . . ?
C5 C1 C2 C3 29.63(18) . . . . ?
C1 C2 C3 C4 -2.90(19) . . . . ?
C2 C3 C4 C5 -25.18(18) . . . . ?
C3 C4 C5 O2 164.10(14) . . . . ?
C3 C4 C5 C6 -77.42(17) . . . . ?
C3 C4 C5 C1 43.97(16) . . . . ?
C11 C1 C5 O2 65.08(18) . . . . ?
C2 C1 C5 O2 -167.38(13) . . . . ?
C11 C1 C5 C6 -50.22(18) . . . . ?
C2 C1 C5 C6 77.32(16) . . . . ?
C11 C1 C5 C4 -173.40(14) . . . . ?
C2 C1 C5 C4 -45.86(16) . . . . ?
O2 C5 C6 C7 -17.85(17) . . . . ?
C4 C5 C6 C7 -141.87(15) . . . . ?
C1 C5 C6 C7 102.26(16) . . . . ?
C5 C6 C7 C8 1.14(19) . . . . ?
C6 C7 C8 O2 16.07(18) . . . . ?
C6 C7 C8 C9 -104.60(17) . . . . ?
O2 C8 C9 C15 -163.38(12) . . . . ?
C7 C8 C9 C15 -47.16(17) . . . . ?
O2 C8 C9 C10 -37.74(19) . . . . ?
C7 C8 C9 C10 78.48(19) . . . . ?
C15 C9 C10 C12 -138.79(13) . . . . ?
C8 C9 C10 C12 93.60(17) . . . . ?
C15 C9 C10 C11 94.56(15) . . . . ?
C8 C9 C10 C11 -33.1(2) . . . . ?
C15 C9 C10 C13 -22.71(16) . . . . ?
C8 C9 C10 C13 -150.32(14) . . . . ?
C5 C1 C11 C10 -64.2(2) . . . . ?
C2 C1 C11 C10 176.18(14) . . . . ?
C12 C10 C11 C1 -56.83(19) . . . . ?
C13 C10 C11 C1 -176.65(15) . . . . ?
C9 C10 C11 C1 69.64(19) . . . . ?
C12 C10 C13 C14 150.39(15) . . . . ?
C11 C10 C13 C14 -89.19(16) . . . . ?
C9 C10 C13 C14 33.87(17) . . . . ?
C10 C13 C14 C15 -32.07(18) . . . . ?
C13 C14 C15 O1 -163.73(16) . . . . ?
C13 C14 C15 C9 17.25(18) . . . . ?
C8 C9 C15 O1 -42.3(2) . . . . ?
C10 C9 C15 O1 -175.20(15) . . . . ?
C8 C9 C15 C14 136.76(14) . . . . ?
C10 C9 C15 C14 3.84(17) . . . . ?
C7 C8 O2 C5 -27.20(15) . . . . ?
C9 C8 O2 C5 94.96(14) . . . . ?
C6 C5 O2 C8 27.86(15) . . . . ?
C4 C5 O2 C8 152.63(14) . . . . ?
C1 C5 O2 C8 -92.63(15) . . . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036

