 
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
 'C11 H22 O2' 
_chemical_formula_weight          186.28

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            61
_space_group_name_H-M_alt         'P b c a'
_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'
 '-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                    9.6851(3)
_cell_length_b                    7.3807(3)
_cell_length_c                    31.3965(11)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2244.31(14)
_cell_formula_units_Z             8
_cell_measurement_temperature   180.01(12) 
_cell_measurement_reflns_used   6075
_cell_measurement_theta_min     5.3470
_cell_measurement_theta_max     71.6080
 
_exptl_crystal_description        'sheet-like'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.103          
_exptl_crystal_F_000              832
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.42
_exptl_crystal_size_mid           0.34
_exptl_crystal_size_min           0.03
_exptl_absorpt_coefficient_mu     0.574
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_T_min                   0.60615
_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 180.01(12) 
_diffrn_ambient_environment N~2~
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix'
_diffrn_detector 'CCD plate'
_diffrn_detector_type HyPix
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             17673
_diffrn_reflns_av_unetI/netI      0.0258
_diffrn_reflns_av_R_equivalents   0.0468
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -37
_diffrn_reflns_limit_l_max        37
_diffrn_reflns_theta_min          2.815
_diffrn_reflns_theta_max          66.587
_diffrn_reflns_theta_full         66.587
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              1988
_reflns_number_gt                 1801
_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        ?
_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)+(0.0513P)²+4.7514P] 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_number_reflns          1988
_refine_ls_number_parameters      123
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0795
_refine_ls_R_factor_gt            0.0755
_refine_ls_wR_factor_ref          0.1820
_refine_ls_wR_factor_gt           0.1797
_refine_ls_goodness_of_fit_ref    1.022
_refine_ls_restrained_S_all       1.022
_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
O1 O 0.62684(18) 0.6855(3) 0.66119(6) 0.0396(5) Uani 1 1 d . . . . .
H1 H 0.6175 0.5839 0.6713 0.059 Uiso 1 1 calc R U . . .
O2 O 0.3505(2) 0.8473(3) 0.79938(7) 0.0508(6) Uani 1 1 d . . . . .
H2 H 0.2974 0.8048 0.8171 0.076 Uiso 1 1 calc R U . . .
C1 C 0.4032(4) 0.7515(5) 0.52968(11) 0.0603(10) Uani 1 1 d . . . . .
H1A H 0.4340 0.8330 0.5078 0.091 Uiso 1 1 calc R U . . .
H1B H 0.3087 0.7775 0.5366 0.091 Uiso 1 1 calc R U . . .
H1C H 0.4105 0.6290 0.5197 0.091 Uiso 1 1 calc R U . . .
C2 C 0.6440(3) 0.7432(5) 0.55759(11) 0.0538(9) Uani 1 1 d . . . . .
H2A H 0.6546 0.6230 0.5464 0.081 Uiso 1 1 calc R U . . .
H2B H 0.7003 0.7565 0.5826 0.081 Uiso 1 1 calc R U . . .
H2C H 0.6722 0.8299 0.5365 0.081 Uiso 1 1 calc R U . . .
C3 C 0.4925(3) 0.7754(4) 0.56924(9) 0.0414(7) Uani 1 1 d . . . . .
C4 C 0.4750(4) 0.9672(4) 0.58820(10) 0.0514(8) Uani 1 1 d . . . . .
H4A H 0.5330 1.0534 0.5732 0.062 Uiso 1 1 calc R U . . .
H4B H 0.3797 1.0065 0.5859 0.062 Uiso 1 1 calc R U . . .
C5 C 0.5177(3) 0.9532(4) 0.63444(10) 0.0466(8) Uani 1 1 d . . . . .
H5A H 0.4624 1.0338 0.6519 0.056 Uiso 1 1 calc R U . . .
H5B H 0.6141 0.9857 0.6378 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4940(3) 0.7536(4) 0.64773(9) 0.0359(7) Uani 1 1 d . . . . .
C7 C 0.4434(3) 0.6601(4) 0.60669(9) 0.0402(7) Uani 1 1 d . . . . .
H7 H 0.3425 0.6705 0.6070 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4741(4) 0.4593(4) 0.60366(11) 0.0533(9) Uani 1 1 d . . . . .
H8A H 0.4386 0.4128 0.5773 0.080 Uiso 1 1 calc R U . . .
H8B H 0.4312 0.3972 0.6270 0.080 Uiso 1 1 calc R U . . .
H8C H 0.5722 0.4405 0.6047 0.080 Uiso 1 1 calc R U . . .
C9 C 0.3902(3) 0.7314(5) 0.68377(9) 0.0433(7) Uani 1 1 d . . . . .
H9A H 0.3041 0.7871 0.6749 0.052 Uiso 1 1 calc R U . . .
H9B H 0.3726 0.6030 0.6874 0.052 Uiso 1 1 calc R U . . .
C10 C 0.4291(3) 0.8090(5) 0.72674(9) 0.0477(8) Uani 1 1 d . . . . .
H10A H 0.5139 0.7529 0.7366 0.057 Uiso 1 1 calc R U . . .
H10B H 0.4455 0.9382 0.7240 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3178(3) 0.7773(5) 0.75856(9) 0.0490(8) Uani 1 1 d . . . . .
H11A H 0.2333 0.8336 0.7485 0.059 Uiso 1 1 calc R U . . .
H11B H 0.3012 0.6481 0.7609 0.059 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 C6 1.445(3) . ?
O1 H1 0.8200 . ?
O2 C11 1.418(4) . ?
O2 H2 0.8200 . ?
C1 C3 1.524(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.531(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C7 1.528(4) . ?
C3 C4 1.545(4) . ?
C4 C5 1.513(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.549(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.522(4) . ?
C6 C7 1.542(4) . ?
C7 C8 1.515(4) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.489(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
 
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
C6 O1 H1 109.5 . . ?
C11 O2 H2 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 C2 109.4(3) . . ?
C1 C3 C7 112.7(3) . . ?
C2 C3 C7 113.3(3) . . ?
C1 C3 C4 110.9(3) . . ?
C2 C3 C4 109.9(3) . . ?
C7 C3 C4 100.3(2) . . ?
C5 C4 C3 106.1(3) . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C4 C5 C6 106.4(2) . . ?
C4 C5 H5A 110.4 . . ?
C6 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C6 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
O1 C6 C9 109.5(2) . . ?
O1 C6 C7 111.8(2) . . ?
C9 C6 C7 111.3(2) . . ?
O1 C6 C5 106.1(2) . . ?
C9 C6 C5 113.6(2) . . ?
C7 C6 C5 104.4(2) . . ?
C8 C7 C3 115.8(3) . . ?
C8 C7 C6 115.3(3) . . ?
C3 C7 C6 107.2(2) . . ?
C8 C7 H7 105.9 . . ?
C3 C7 H7 105.9 . . ?
C6 C7 H7 105.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C6 117.2(2) . . ?
C10 C9 H9A 108.0 . . ?
C6 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
C6 C9 H9B 108.0 . . ?
H9A C9 H9B 107.2 . . ?
C11 C10 C9 111.0(3) . . ?
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 C10 112.8(3) . . ?
O2 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
O2 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
 
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
C1 C3 C4 C5 157.7(3) . . . . ?
C2 C3 C4 C5 -81.2(3) . . . . ?
C7 C3 C4 C5 38.4(3) . . . . ?
C3 C4 C5 C6 -25.7(3) . . . . ?
C4 C5 C6 O1 120.6(3) . . . . ?
C4 C5 C6 C9 -119.1(3) . . . . ?
C4 C5 C6 C7 2.4(3) . . . . ?
C1 C3 C7 C8 74.6(3) . . . . ?
C2 C3 C7 C8 -50.3(4) . . . . ?
C4 C3 C7 C8 -167.4(3) . . . . ?
C1 C3 C7 C6 -155.1(3) . . . . ?
C2 C3 C7 C6 80.0(3) . . . . ?
C4 C3 C7 C6 -37.1(3) . . . . ?
O1 C6 C7 C8 38.5(3) . . . . ?
C9 C6 C7 C8 -84.3(3) . . . . ?
C5 C6 C7 C8 152.8(3) . . . . ?
O1 C6 C7 C3 -92.0(3) . . . . ?
C9 C6 C7 C3 145.2(2) . . . . ?
C5 C6 C7 C3 22.2(3) . . . . ?
O1 C6 C9 C10 53.1(4) . . . . ?
C7 C6 C9 C10 177.2(3) . . . . ?
C5 C6 C9 C10 -65.3(4) . . . . ?
C6 C9 C10 C11 179.9(3) . . . . ?
C9 C10 C11 O2 179.7(3) . . . . ?
 
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  0.82 2.00 2.795(3) 164.0 3_646
O2 H2 O1  0.82 1.99 2.766(3) 157.1 6_557
 
_refine_diff_density_max    0.386
_refine_diff_density_min   -0.235
_refine_diff_density_rms    0.060



