 
data_V19305 
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H22 O' 
_chemical_formula_weight          254.35 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0492   0.0322 
 '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                    6.7708(6) 
_cell_length_b                    10.8979(10) 
_cell_length_c                    19.414(2) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      1432.5(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     9317 
_cell_measurement_theta_min       4.06 
_cell_measurement_theta_max       74.41 
  
_exptl_crystal_description        Block 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_density_diffrn     1.179 
_exptl_crystal_F_000              552 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.350 
_exptl_crystal_size_mid           0.300 
_exptl_crystal_size_min           0.150 
_exptl_absorpt_coefficient_mu     0.541 
_shelx_estimated_absorpt_T_min    0.833 
_shelx_estimated_absorpt_T_max    0.923 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6977 
_exptl_absorpt_correction_T_max   0.7538 
_exptl_absorpt_process_details    'SADABS-2016/2 (Sheldrick, 2014)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'I\mS HB micro-focus sealed tube' 
_diffrn_measurement_device_type   'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  7.69 
_diffrn_reflns_number             48838 
_diffrn_reflns_av_unetI/netI      0.0174 
_diffrn_reflns_av_R_equivalents   0.0345 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          4.555 
_diffrn_reflns_theta_max          74.559 
_diffrn_reflns_theta_full         67.679 
_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              2938 
_reflns_number_gt                 2929 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.715 
_reflns_Friedel_fraction_max      0.998 
_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        'APEX3 v2017.3-0 (Bruker-AXS, 2017)' 
_computing_cell_refinement        'SAINT v8.38A (Bruker-AXS, 2013)' 
_computing_data_reduction         'SAINT v8.38A (Bruker-AXS, 2013)' 
_computing_structure_solution     'SHELXS-2013/1 (Sheldrick, 2013)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0371P)²+0.2874P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1220 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    0.10(4) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          2938 
_refine_ls_number_parameters      174 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0283 
_refine_ls_R_factor_gt            0.0282 
_refine_ls_wR_factor_ref          0.0700 
_refine_ls_wR_factor_gt           0.0699 
_refine_ls_goodness_of_fit_ref    1.059 
_refine_ls_restrained_S_all       1.059 
_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 0.7111(2) 0.28519(12) 0.66762(6) 0.0158(3) Uani 1 1 d . . . . . 
C2 C 0.5291(2) 0.26989(12) 0.70939(7) 0.0185(3) Uani 1 1 d . . . . . 
O1 O 0.48648(16) 0.18136(10) 0.74487(6) 0.0253(2) Uani 1 1 d . . . . . 
C3 C 0.4012(2) 0.38323(13) 0.69991(8) 0.0233(3) Uani 1 1 d . . . . . 
H3A H 0.393369 0.430873 0.743240 0.028 Uiso 1 1 calc R U . . . 
H3B H 0.265935 0.360063 0.685592 0.028 Uiso 1 1 calc R U . . . 
C4 C 0.5034(2) 0.45764(12) 0.64364(7) 0.0219(3) Uani 1 1 d . . . . . 
H4A H 0.421351 0.460702 0.601467 0.026 Uiso 1 1 calc R U . . . 
H4B H 0.529344 0.542512 0.659404 0.026 Uiso 1 1 calc R U . . . 
C5 C 0.6946(2) 0.39008(12) 0.63034(7) 0.0171(3) Uani 1 1 d . . . . . 
C6 C 0.8389(2) 0.44202(12) 0.58312(7) 0.0198(3) Uani 1 1 d . . . . . 
H6 H 0.824125 0.526951 0.573375 0.024 Uiso 1 1 calc R U . . . 
C7 C 0.9894(2) 0.38605(13) 0.55165(7) 0.0211(3) Uani 1 1 d . . . . . 
H7 H 1.071599 0.438387 0.525026 0.025 Uiso 1 1 calc R U . . . 
C8 C 1.0489(2) 0.25343(13) 0.55178(8) 0.0218(3) Uani 1 1 d . . . . . 
H8A H 1.180307 0.248024 0.573900 0.026 Uiso 1 1 calc R U . . . 
H8B H 1.065984 0.228019 0.503182 0.026 Uiso 1 1 calc R U . . . 
C9 C 0.9146(2) 0.15774(12) 0.58671(7) 0.0157(3) Uani 1 1 d . . . . . 
H9 H 0.786885 0.156467 0.560826 0.019 Uiso 1 1 calc R U . . . 
C10 C 1.0099(2) 0.03016(12) 0.57859(7) 0.0175(3) Uani 1 1 d . . . . . 
H10 H 1.077532 0.029432 0.532795 0.021 Uiso 1 1 calc R U . . . 
C15 C 0.8664(2) -0.07665(12) 0.57883(7) 0.0185(3) Uani 1 1 d . . . . . 
C16 C 0.6898(2) -0.07434(13) 0.60842(7) 0.0223(3) Uani 1 1 d . . . . . 
H16A H 0.607124 -0.144691 0.606639 0.027 Uiso 1 1 calc R U . . . 
H16B H 0.646066 -0.002329 0.631394 0.027 Uiso 1 1 calc R U . . . 
C17 C 0.9404(3) -0.18963(13) 0.54189(8) 0.0273(3) Uani 1 1 d . . . . . 
H17A H 0.843309 -0.255788 0.546524 0.041 Uiso 1 1 calc R U . . . 
H17B H 1.066184 -0.215643 0.562187 0.041 Uiso 1 1 calc R U . . . 
H17C H 0.959885 -0.170764 0.493007 0.041 Uiso 1 1 calc R U . . . 
C11 C 1.1718(2) 0.01327(13) 0.63362(8) 0.0210(3) Uani 1 1 d . . . . . 
H11A H 1.231082 -0.069307 0.628704 0.025 Uiso 1 1 calc R U . . . 
H11B H 1.277325 0.074712 0.626089 0.025 Uiso 1 1 calc R U . . . 
C12 C 1.0898(2) 0.02762(12) 0.70628(7) 0.0202(3) Uani 1 1 d . . . . . 
H12A H 1.017628 -0.048178 0.718748 0.024 Uiso 1 1 calc R U . . . 
H12B H 1.201715 0.036390 0.738741 0.024 Uiso 1 1 calc R U . . . 
C13 C 0.95327(19) 0.13567(12) 0.71521(7) 0.0171(3) Uani 1 1 d . . . . . 
C18 C 0.9244(2) 0.17345(13) 0.78908(7) 0.0211(3) Uani 1 1 d . . . . . 
H18A H 0.826200 0.239365 0.791451 0.032 Uiso 1 1 calc R U . . . 
H18B H 1.050096 0.202687 0.807996 0.032 Uiso 1 1 calc R U . . . 
H18C H 0.878183 0.102900 0.815909 0.032 Uiso 1 1 calc R U . . . 
C14 C 0.86725(19) 0.19148(11) 0.66129(6) 0.0150(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 1.3575(18) . ? 
C1 C14 1.4751(18) . ? 
C1 C2 1.4843(18) . ? 
C2 O1 1.2201(18) . ? 
C2 C3 1.5198(19) . ? 
C3 C4 1.526(2) . ? 
C3 H3A 0.9900 . ? 
C3 H3B 0.9900 . ? 
C4 C5 1.5119(19) . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C5 C6 1.454(2) . ? 
C6 C7 1.335(2) . ? 
C6 H6 0.9500 . ? 
C7 C8 1.500(2) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.5408(18) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 C14 1.5278(18) . ? 
C9 C10 1.5411(17) . ? 
C9 H9 1.0000 . ? 
C10 C15 1.5166(19) . ? 
C10 C11 1.5414(19) . ? 
C10 H10 1.0000 . ? 
C15 C16 1.327(2) . ? 
C15 C17 1.5105(19) . ? 
C16 H16A 0.9500 . ? 
C16 H16B 0.9500 . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
C11 C12 1.524(2) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 C13 1.5073(19) . ? 
C12 H12A 0.9900 . ? 
C12 H12B 0.9900 . ? 
C13 C14 1.3436(18) . ? 
C13 C18 1.5048(19) . ? 
C18 H18A 0.9800 . ? 
C18 H18B 0.9800 . ? 
C18 H18C 0.9800 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C5 C1 C14 126.68(12) . . ? 
C5 C1 C2 108.52(12) . . ? 
C14 C1 C2 124.24(11) . . ? 
O1 C2 C1 126.43(13) . . ? 
O1 C2 C3 125.18(13) . . ? 
C1 C2 C3 108.39(11) . . ? 
C2 C3 C4 105.08(12) . . ? 
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 104.58(11) . . ? 
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 . . ? 
C1 C5 C6 127.50(13) . . ? 
C1 C5 C4 112.91(12) . . ? 
C6 C5 C4 119.56(12) . . ? 
C7 C6 C5 128.54(13) . . ? 
C7 C6 H6 115.7 . . ? 
C5 C6 H6 115.7 . . ? 
C6 C7 C8 130.09(13) . . ? 
C6 C7 H7 115.0 . . ? 
C8 C7 H7 115.0 . . ? 
C7 C8 C9 119.62(12) . . ? 
C7 C8 H8A 107.4 . . ? 
C9 C8 H8A 107.4 . . ? 
C7 C8 H8B 107.4 . . ? 
C9 C8 H8B 107.4 . . ? 
H8A C8 H8B 106.9 . . ? 
C14 C9 C8 112.21(11) . . ? 
C14 C9 C10 113.70(11) . . ? 
C8 C9 C10 108.55(11) . . ? 
C14 C9 H9 107.4 . . ? 
C8 C9 H9 107.4 . . ? 
C10 C9 H9 107.4 . . ? 
C15 C10 C9 115.06(11) . . ? 
C15 C10 C11 111.22(11) . . ? 
C9 C10 C11 109.56(11) . . ? 
C15 C10 H10 106.9 . . ? 
C9 C10 H10 106.9 . . ? 
C11 C10 H10 106.9 . . ? 
C16 C15 C17 121.35(13) . . ? 
C16 C15 C10 124.36(13) . . ? 
C17 C15 C10 114.29(12) . . ? 
C15 C16 H16A 120.0 . . ? 
C15 C16 H16B 120.0 . . ? 
H16A C16 H16B 120.0 . . ? 
C15 C17 H17A 109.5 . . ? 
C15 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
C15 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
C12 C11 C10 111.74(11) . . ? 
C12 C11 H11A 109.3 . . ? 
C10 C11 H11A 109.3 . . ? 
C12 C11 H11B 109.3 . . ? 
C10 C11 H11B 109.3 . . ? 
H11A C11 H11B 107.9 . . ? 
C13 C12 C11 114.21(11) . . ? 
C13 C12 H12A 108.7 . . ? 
C11 C12 H12A 108.7 . . ? 
C13 C12 H12B 108.7 . . ? 
C11 C12 H12B 108.7 . . ? 
H12A C12 H12B 107.6 . . ? 
C14 C13 C18 124.23(12) . . ? 
C14 C13 C12 122.00(12) . . ? 
C18 C13 C12 113.77(12) . . ? 
C13 C18 H18A 109.5 . . ? 
C13 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
C13 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C13 C14 C1 124.00(12) . . ? 
C13 C14 C9 122.59(12) . . ? 
C1 C14 C9 113.32(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 
C5 C1 C2 O1 173.96(14) . . . . ? 
C14 C1 C2 O1 2.0(2) . . . . ? 
C5 C1 C2 C3 -5.26(15) . . . . ? 
C14 C1 C2 C3 -177.21(12) . . . . ? 
O1 C2 C3 C4 -172.03(14) . . . . ? 
C1 C2 C3 C4 7.20(14) . . . . ? 
C2 C3 C4 C5 -6.34(14) . . . . ? 
C14 C1 C5 C6 -9.2(2) . . . . ? 
C2 C1 C5 C6 179.09(13) . . . . ? 
C14 C1 C5 C4 172.73(12) . . . . ? 
C2 C1 C5 C4 1.03(15) . . . . ? 
C3 C4 C5 C1 3.51(15) . . . . ? 
C3 C4 C5 C6 -174.72(12) . . . . ? 
C1 C5 C6 C7 20.2(2) . . . . ? 
C4 C5 C6 C7 -161.89(14) . . . . ? 
C5 C6 C7 C8 4.0(3) . . . . ? 
C6 C7 C8 C9 6.5(2) . . . . ? 
C7 C8 C9 C14 -53.97(17) . . . . ? 
C7 C8 C9 C10 179.52(12) . . . . ? 
C14 C9 C10 C15 81.49(14) . . . . ? 
C8 C9 C10 C15 -152.87(11) . . . . ? 
C14 C9 C10 C11 -44.68(15) . . . . ? 
C8 C9 C10 C11 80.97(14) . . . . ? 
C9 C10 C15 C16 -24.94(19) . . . . ? 
C11 C10 C15 C16 100.38(16) . . . . ? 
C9 C10 C15 C17 155.08(12) . . . . ? 
C11 C10 C15 C17 -79.61(15) . . . . ? 
C15 C10 C11 C12 -70.33(14) . . . . ? 
C9 C10 C11 C12 58.00(14) . . . . ? 
C10 C11 C12 C13 -44.76(16) . . . . ? 
C11 C12 C13 C14 18.31(18) . . . . ? 
C11 C12 C13 C18 -161.66(12) . . . . ? 
C18 C13 C14 C1 -9.3(2) . . . . ? 
C12 C13 C14 C1 170.73(12) . . . . ? 
C18 C13 C14 C9 174.39(13) . . . . ? 
C12 C13 C14 C9 -5.6(2) . . . . ? 
C5 C1 C14 C13 138.53(14) . . . . ? 
C2 C1 C14 C13 -51.01(19) . . . . ? 
C5 C1 C14 C9 -44.87(18) . . . . ? 
C2 C1 C14 C9 125.60(13) . . . . ? 
C8 C9 C14 C13 -104.09(14) . . . . ? 
C10 C9 C14 C13 19.59(18) . . . . ? 
C8 C9 C14 C1 79.25(14) . . . . ? 
C10 C9 C14 C1 -157.07(11) . . . . ? 
  
_refine_diff_density_max    0.172 
_refine_diff_density_min   -0.158 
_refine_diff_density_rms    0.038 
  
  
  
