 
data_3
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H26 O2' 
_chemical_formula_weight          286.40

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                    8.8797(3)
_cell_length_b                    11.8527(4)
_cell_length_c                    14.9997(5)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1578.69(9)
_cell_formula_units_Z             4
_cell_measurement_temperature   179.99(10) 
_cell_measurement_reflns_used   5672
_cell_measurement_theta_min     2.6980
_cell_measurement_theta_max     29.3150
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.205          
_exptl_crystal_F_000              624
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.35
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.19
_exptl_absorpt_coefficient_mu     0.076
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_T_min                   0.91851
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_correction_type            multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature 179.99(10) 
_diffrn_ambient_environment N~2~
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector 'CCD plate'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             10392
_diffrn_reflns_av_unetI/netI      0.0342
_diffrn_reflns_av_R_equivalents   0.0308
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          2.666
_diffrn_reflns_theta_max          27.483
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3628
_reflns_number_gt                 3375
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.744
_reflns_Friedel_fraction_max      0.997
_reflns_Friedel_fraction_full     0.999
 
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_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)+(0.0580P)²+0.1228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_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
;
 Flack x determined using 1365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.8(5)
_chemical_absolute_configuration  unk
_refine_ls_number_reflns          3628
_refine_ls_number_parameters      193
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0392
_refine_ls_R_factor_gt            0.0352
_refine_ls_wR_factor_ref          0.0960
_refine_ls_wR_factor_gt           0.0939
_refine_ls_goodness_of_fit_ref    1.033
_refine_ls_restrained_S_all       1.033
_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
O1 O 0.50510(13) 0.29426(10) 0.58334(9) 0.0291(3) Uani 1 1 d . . . . .
O2 O 0.21471(16) 0.57186(12) 0.46189(9) 0.0375(3) Uani 1 1 d . . . . .
C1 C 0.63708(18) 0.32006(13) 0.58017(10) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.75933(19) 0.23179(14) 0.58659(12) 0.0257(4) Uani 1 1 d . . . . .
H2A H 0.8267 0.2380 0.5359 0.031 Uiso 1 1 calc R U . . .
H2B H 0.7150 0.1570 0.5861 0.031 Uiso 1 1 calc R U . . .
C3 C 0.8471(2) 0.24990(14) 0.67322(13) 0.0274(4) Uani 1 1 d . . . . .
H3A H 0.9272 0.1944 0.6765 0.033 Uiso 1 1 calc R U . . .
H3B H 0.7800 0.2368 0.7232 0.033 Uiso 1 1 calc R U . . .
C4 C 0.91602(19) 0.36810(15) 0.68250(11) 0.0249(4) Uani 1 1 d . . . . .
C5 C 0.78866(19) 0.45647(13) 0.66575(11) 0.0215(3) Uani 1 1 d . . . . .
H5 H 0.7162 0.4428 0.7138 0.026 Uiso 1 1 calc R U . . .
C6 C 0.8397(2) 0.57894(16) 0.68007(15) 0.0351(5) Uani 1 1 d . . . . .
H6A H 0.8669 0.5887 0.7422 0.042 Uiso 1 1 calc R U . . .
H6B H 0.9292 0.5925 0.6446 0.042 Uiso 1 1 calc R U . . .
C7 C 0.7205(2) 0.66714(15) 0.65555(14) 0.0298(4) Uani 1 1 d . . . . .
H7A H 0.7479 0.7010 0.5990 0.036 Uiso 1 1 calc R U . . .
H7B H 0.7219 0.7263 0.7002 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5589(2) 0.62079(13) 0.64826(11) 0.0216(3) Uani 1 1 d . . . . .
C9 C 0.4567(2) 0.71854(14) 0.61641(12) 0.0271(4) Uani 1 1 d . . . . .
H9A H 0.4449 0.7727 0.6644 0.032 Uiso 1 1 calc R U . . .
H9B H 0.5046 0.7568 0.5668 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3016(2) 0.67654(15) 0.58745(12) 0.0268(4) Uani 1 1 d . . . . .
H10A H 0.2490 0.6455 0.6386 0.032 Uiso 1 1 calc R U . . .
H10B H 0.2430 0.7394 0.5649 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3147(2) 0.58769(14) 0.51639(11) 0.0246(4) Uani 1 1 d . . . . .
C12 C 0.4512(2) 0.51784(14) 0.51751(11) 0.0237(3) Uani 1 1 d . . . . .
H12 H 0.4628 0.4644 0.4726 0.028 Uiso 1 1 calc R U . . .
C13 C 0.56036(19) 0.52604(13) 0.57913(10) 0.0199(3) Uani 1 1 d . . . . .
C14 C 0.69373(18) 0.44370(13) 0.57845(11) 0.0197(3) Uani 1 1 d . . . . .
C15 C 0.7836(2) 0.46534(16) 0.49127(12) 0.0311(4) Uani 1 1 d . . . . .
H15A H 0.8609 0.4093 0.4852 0.047 Uiso 1 1 calc R U . . .
H15B H 0.8287 0.5389 0.4936 0.047 Uiso 1 1 calc R U . . .
H15C H 0.7166 0.4613 0.4411 0.047 Uiso 1 1 calc R U . . .
C16 C 0.9692(2) 0.38165(18) 0.77984(13) 0.0357(5) Uani 1 1 d . . . . .
H16A H 0.8832 0.3860 0.8185 0.053 Uiso 1 1 calc R U . . .
H16B H 1.0275 0.4495 0.7853 0.053 Uiso 1 1 calc R U . . .
H16C H 1.0299 0.3179 0.7963 0.053 Uiso 1 1 calc R U . . .
C17 C 1.0559(2) 0.37829(18) 0.62246(14) 0.0363(4) Uani 1 1 d . . . . .
H17A H 1.1346 0.3307 0.6452 0.054 Uiso 1 1 calc R U . . .
H17B H 1.0898 0.4552 0.6218 0.054 Uiso 1 1 calc R U . . .
H17C H 1.0307 0.3553 0.5629 0.054 Uiso 1 1 calc R U . . .
C18 C 0.5008(2) 0.58123(16) 0.73867(11) 0.0275(4) Uani 1 1 d . . . . .
H18 H 0.5273 0.6248 0.7878 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4171(2) 0.49202(16) 0.75447(13) 0.0328(4) Uani 1 1 d . . . . .
H19A H 0.3874 0.4456 0.7077 0.039 Uiso 1 1 calc R U . . .
H19B H 0.3875 0.4753 0.8125 0.039 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
O1 C1 1.212(2) . ?
O2 C11 1.222(2) . ?
C1 C2 1.511(2) . ?
C1 C14 1.550(2) . ?
C2 C3 1.530(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.535(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C17 1.539(3) . ?
C4 C16 1.543(2) . ?
C4 C5 1.562(2) . ?
C5 C6 1.536(2) . ?
C5 C14 1.565(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.532(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.541(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C18 1.525(2) . ?
C8 C13 1.529(2) . ?
C8 C9 1.547(2) . ?
C9 C10 1.527(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.503(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.468(2) . ?
C12 C13 1.343(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.535(2) . ?
C14 C15 1.553(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.314(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
 
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 C2 121.17(15) . . ?
O1 C1 C14 123.58(15) . . ?
C2 C1 C14 115.01(13) . . ?
C1 C2 C3 108.83(14) . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C2 C3 C4 114.08(15) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C17 109.90(15) . . ?
C3 C4 C16 107.63(15) . . ?
C17 C4 C16 107.38(15) . . ?
C3 C4 C5 107.98(13) . . ?
C17 C4 C5 115.95(15) . . ?
C16 C4 C5 107.69(14) . . ?
C6 C5 C14 111.55(14) . . ?
C6 C5 C4 113.45(14) . . ?
C14 C5 C4 117.37(13) . . ?
C6 C5 H5 104.3 . . ?
C14 C5 H5 104.3 . . ?
C4 C5 H5 104.3 . . ?
C7 C6 C5 114.06(15) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 114.65(14) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C18 C8 C13 112.36(13) . . ?
C18 C8 C7 111.20(15) . . ?
C13 C8 C7 107.58(14) . . ?
C18 C8 C9 107.84(14) . . ?
C13 C8 C9 110.23(14) . . ?
C7 C8 C9 107.53(14) . . ?
C10 C9 C8 111.87(14) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 111.10(15) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O2 C11 C12 121.41(15) . . ?
O2 C11 C10 121.72(16) . . ?
C12 C11 C10 116.83(15) . . ?
C13 C12 C11 124.27(15) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C12 C13 C8 120.91(15) . . ?
C12 C13 C14 120.44(14) . . ?
C8 C13 C14 118.58(14) . . ?
C13 C14 C1 110.53(13) . . ?
C13 C14 C15 107.27(13) . . ?
C1 C14 C15 109.69(13) . . ?
C13 C14 C5 110.40(13) . . ?
C1 C14 C5 104.62(12) . . ?
C15 C14 C5 114.33(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C8 126.81(16) . . ?
C19 C18 H18 116.6 . . ?
C8 C18 H18 116.6 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
 
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 -113.83(19) . . . . ?
C14 C1 C2 C3 60.66(18) . . . . ?
C1 C2 C3 C4 -56.94(19) . . . . ?
C2 C3 C4 C17 -75.57(19) . . . . ?
C2 C3 C4 C16 167.79(15) . . . . ?
C2 C3 C4 C5 51.79(19) . . . . ?
C3 C4 C5 C6 175.59(16) . . . . ?
C17 C4 C5 C6 -60.6(2) . . . . ?
C16 C4 C5 C6 59.6(2) . . . . ?
C3 C4 C5 C14 -51.92(18) . . . . ?
C17 C4 C5 C14 71.86(19) . . . . ?
C16 C4 C5 C14 -167.88(15) . . . . ?
C14 C5 C6 C7 39.4(2) . . . . ?
C4 C5 C6 C7 174.61(15) . . . . ?
C5 C6 C7 C8 17.4(2) . . . . ?
C6 C7 C8 C18 66.3(2) . . . . ?
C6 C7 C8 C13 -57.1(2) . . . . ?
C6 C7 C8 C9 -175.83(16) . . . . ?
C18 C8 C9 C10 -72.44(18) . . . . ?
C13 C8 C9 C10 50.55(19) . . . . ?
C7 C8 C9 C10 167.54(15) . . . . ?
C8 C9 C10 C11 -55.9(2) . . . . ?
C9 C10 C11 O2 -152.92(17) . . . . ?
C9 C10 C11 C12 29.3(2) . . . . ?
O2 C11 C12 C13 -175.42(17) . . . . ?
C10 C11 C12 C13 2.4(2) . . . . ?
C11 C12 C13 C8 -7.4(3) . . . . ?
C11 C12 C13 C14 175.77(15) . . . . ?
C18 C8 C13 C12 100.90(18) . . . . ?
C7 C8 C13 C12 -136.38(16) . . . . ?
C9 C8 C13 C12 -19.4(2) . . . . ?
C18 C8 C13 C14 -82.18(18) . . . . ?
C7 C8 C13 C14 40.54(18) . . . . ?
C9 C8 C13 C14 157.51(14) . . . . ?
C12 C13 C14 C1 -54.49(19) . . . . ?
C8 C13 C14 C1 128.58(15) . . . . ?
C12 C13 C14 C15 65.07(19) . . . . ?
C8 C13 C14 C15 -111.86(16) . . . . ?
C12 C13 C14 C5 -169.76(14) . . . . ?
C8 C13 C14 C5 13.31(19) . . . . ?
O1 C1 C14 C13 -1.3(2) . . . . ?
C2 C1 C14 C13 -175.65(13) . . . . ?
O1 C1 C14 C15 -119.39(18) . . . . ?
C2 C1 C14 C15 66.27(18) . . . . ?
O1 C1 C14 C5 117.54(18) . . . . ?
C2 C1 C14 C5 -56.80(17) . . . . ?
C6 C5 C14 C13 -54.80(18) . . . . ?
C4 C5 C14 C13 171.86(13) . . . . ?
C6 C5 C14 C1 -173.73(14) . . . . ?
C4 C5 C14 C1 52.93(17) . . . . ?
C6 C5 C14 C15 66.25(19) . . . . ?
C4 C5 C14 C15 -67.08(18) . . . . ?
C13 C8 C18 C19 -20.9(3) . . . . ?
C7 C8 C18 C19 -141.51(19) . . . . ?
C9 C8 C18 C19 100.8(2) . . . . ?
 
_refine_diff_density_max    0.199
_refine_diff_density_min   -0.175
_refine_diff_density_rms    0.037



