data_mjr17052
_audit_creation_date              2017-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number      '2017/1'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C15 H22 O3'
_chemical_formula_sum             'C15 H22 O3'
_chemical_formula_weight          250.32
_chemical_absolute_configuration  rmad
_chemical_melting_point           ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0150 0.0070 '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' 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system       'orthorhombic'
_space_group_IT_number            18
_space_group_name_H-M_alt         'P 21 21 2'
_space_group_name_Hall            'P 2 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z'
 '-x+1/2, y+1/2, -z'
 'x+1/2, -y+1/2, -z'

_cell_length_a                    13.5577(5)
_cell_length_b                    14.5611(5)
_cell_length_c                    6.8904(2)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1360.27(8)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     9972
_cell_measurement_temperature     304(2)
_cell_measurement_theta_max       60.33
_cell_measurement_theta_min       3.88
_shelx_estimated_absorpt_T_max    0.958
_shelx_estimated_absorpt_T_min    0.919
_exptl_absorpt_coefficient_mu     0.430
_exptl_absorpt_correction_T_max   0.7519
_exptl_absorpt_correction_T_min   0.6212
_exptl_absorpt_correction_type    'none'
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1412 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.8262.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.222
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        'block'
_exptl_crystal_F_000              544
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.1
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0415
_diffrn_reflns_av_unetI/netI      0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_number             18109
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full         53.594
_diffrn_reflns_theta_max          54.871
_diffrn_reflns_theta_min          3.876
_diffrn_ambient_temperature       303.95
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type   'Bruker D8 Venture'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_type            GaK\a
_diffrn_radiation_wavelength      1.34139
_diffrn_source                    ?
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.713
_reflns_Friedel_fraction_full     0.999
_reflns_Friedel_fraction_max      0.999
_reflns_number_gt                 2399
_reflns_number_total              2587
_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.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection        ?
_computing_data_reduction         'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.154
_refine_diff_density_min          -0.096
_refine_diff_density_rms          0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 929 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.11(10)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.044
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      167
_refine_ls_number_reflns          2587
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0358
_refine_ls_R_factor_gt            0.0324
_refine_ls_restrained_S_all       1.044
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0355P)²+0.1629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0765
_refine_ls_wR_factor_ref          0.0790
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C4(H4), C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
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 0.60445(11) 0.15913(13) 0.6627(2) 0.0687(5) Uani 1 1 d . . . . .
 H1 H 0.661731 0.144557 0.685325 0.103 Uiso 1 1 calc GR . . . .
 O2 O 0.47407(10) 0.34980(9) 0.86783(19) 0.0470(3) Uani 1 1 d . . . . .
 O3 O 0.30838(11) 0.36953(12) 0.2805(2) 0.0625(4) Uani 1 1 d . . . . .
 C1 C 0.57048(15) 0.22058(16) 0.8095(3) 0.0531(5) Uani 1 1 d . . . . .
 H1A H 0.625666 0.259672 0.849653 0.064 Uiso 1 1 calc R . . . .
 C2 C 0.53229(16) 0.16999(17) 0.9857(3) 0.0597(6) Uani 1 1 d . . . . .
 H2A H 0.522206 0.213598 1.090218 0.072 Uiso 1 1 calc R . . . .
 H2B H 0.581646 0.126103 1.027909 0.072 Uiso 1 1 calc R . . . .
 C3 C 0.43645(17) 0.11970(16) 0.9471(3) 0.0560(5) Uani 1 1 d . . . . .
 H3A H 0.412954 0.092573 1.067045 0.067 Uiso 1 1 calc R . . . .
 H3B H 0.448409 0.070339 0.855515 0.067 Uiso 1 1 calc R . . . .
 C4 C 0.35682(14) 0.18364(13) 0.8654(3) 0.0431(4) Uani 1 1 d . . . . .
 H4 H 0.346776 0.232754 0.960600 0.052 Uiso 1 1 calc R . . . .
 C5 C 0.39295(13) 0.22957(12) 0.6750(3) 0.0369(4) Uani 1 1 d . . . . .
 C6 C 0.32182(13) 0.30476(12) 0.6000(2) 0.0366(4) Uani 1 1 d . . . . .
 H6 H 0.258291 0.275919 0.570189 0.044 Uiso 1 1 calc R . . . .
 C7 C 0.36245(15) 0.34697(14) 0.4141(3) 0.0445(4) Uani 1 1 d . . . . .
 C8 C 0.46934(15) 0.36172(16) 0.4031(3) 0.0528(5) Uani 1 1 d . . . . .
 H8 H 0.495900 0.393557 0.298461 0.063 Uiso 1 1 calc R . . . .
 C9 C 0.52821(14) 0.33017(15) 0.5406(3) 0.0512(5) Uani 1 1 d . . . . .
 H9 H 0.595861 0.338473 0.526778 0.061 Uiso 1 1 calc R . . . .
 C10 C 0.49084(14) 0.28140(14) 0.7186(3) 0.0417(4) Uani 1 1 d . . . . .
 C11 C 0.30444(13) 0.38007(13) 0.7539(3) 0.0414(4) Uani 1 1 d . . . . .
 H11 H 0.272145 0.351214 0.865626 0.050 Uiso 1 1 calc R . . . .
 C12 C 0.40226(15) 0.41853(13) 0.8229(3) 0.0490(5) Uani 1 1 d . . . . .
 H12A H 0.428681 0.458459 0.722885 0.059 Uiso 1 1 calc R . . . .
 H12B H 0.390873 0.455666 0.937578 0.059 Uiso 1 1 calc R . . . .
 C13 C 0.23797(17) 0.45770(15) 0.6837(4) 0.0593(6) Uani 1 1 d . . . . .
 H13A H 0.270239 0.490419 0.580711 0.089 Uiso 1 1 calc GR . . . .
 H13B H 0.224844 0.498983 0.789176 0.089 Uiso 1 1 calc GR . . . .
 H13C H 0.176981 0.432580 0.636853 0.089 Uiso 1 1 calc GR . . . .
 C14 C 0.25823(16) 0.13342(16) 0.8428(4) 0.0607(6) Uani 1 1 d . . . . .
 H14A H 0.210728 0.174030 0.785224 0.091 Uiso 1 1 calc GR . . . .
 H14B H 0.235144 0.114044 0.967943 0.091 Uiso 1 1 calc GR . . . .
 H14C H 0.267017 0.080692 0.760910 0.091 Uiso 1 1 calc GR . . . .
 C15 C 0.40335(16) 0.15700(14) 0.5127(3) 0.0505(5) Uani 1 1 d . . . . .
 H15A H 0.339033 0.138963 0.468615 0.076 Uiso 1 1 calc GR . . . .
 H15B H 0.437598 0.104282 0.562316 0.076 Uiso 1 1 calc GR . . . .
 H15C H 0.439871 0.182652 0.406383 0.076 Uiso 1 1 calc GR . . . .


_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 H1 0.8200 . ?
 O1 C1 1.427(3) . ?
 O2 C10 1.449(2) . ?
 O2 C12 1.430(2) . ?
 O3 C7 1.222(2) . ?
 C1 H1A 0.9800 . ?
 C1 C2 1.511(3) . ?
 C1 C10 1.530(3) . ?
 C2 H2A 0.9700 . ?
 C2 H2B 0.9700 . ?
 C2 C3 1.515(3) . ?
 C3 H3A 0.9700 . ?
 C3 H3B 0.9700 . ?
 C3 C4 1.533(3) . ?
 C4 H4 0.9800 . ?
 C4 C5 1.552(2) . ?
 C4 C14 1.532(3) . ?
 C5 C6 1.548(3) . ?
 C5 C10 1.556(2) . ?
 C5 C15 1.545(2) . ?
 C6 H6 0.9800 . ?
 C6 C7 1.524(2) . ?
 C6 C11 1.544(2) . ?
 C7 C8 1.467(3) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.321(3) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.505(3) . ?
 C11 H11 0.9800 . ?
 C11 C12 1.516(3) . ?
 C11 C13 1.525(3) . ?
 C12 H12A 0.9700 . ?
 C12 H12B 0.9700 . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 0.9600 . ?
 C15 H15A 0.9600 . ?
 C15 H15B 0.9600 . ?
 C15 H15C 0.9600 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C1 O1 H1 109.5 . . ?
 C12 O2 C10 115.72(14) . . ?
 O1 C1 H1A 108.5 . . ?
 O1 C1 C2 111.99(19) . . ?
 O1 C1 C10 107.49(16) . . ?
 C2 C1 H1A 108.5 . . ?
 C2 C1 C10 111.65(17) . . ?
 C10 C1 H1A 108.5 . . ?
 C1 C2 H2A 109.0 . . ?
 C1 C2 H2B 109.0 . . ?
 C1 C2 C3 112.86(18) . . ?
 H2A C2 H2B 107.8 . . ?
 C3 C2 H2A 109.0 . . ?
 C3 C2 H2B 109.0 . . ?
 C2 C3 H3A 109.2 . . ?
 C2 C3 H3B 109.2 . . ?
 C2 C3 C4 112.02(18) . . ?
 H3A C3 H3B 107.9 . . ?
 C4 C3 H3A 109.2 . . ?
 C4 C3 H3B 109.2 . . ?
 C3 C4 H4 107.2 . . ?
 C3 C4 C5 110.48(16) . . ?
 C5 C4 H4 107.2 . . ?
 C14 C4 C3 111.23(17) . . ?
 C14 C4 H4 107.2 . . ?
 C14 C4 C5 113.28(16) . . ?
 C4 C5 C10 108.36(14) . . ?
 C6 C5 C4 112.98(14) . . ?
 C6 C5 C10 104.64(14) . . ?
 C15 C5 C4 110.24(15) . . ?
 C15 C5 C6 107.40(15) . . ?
 C15 C5 C10 113.18(15) . . ?
 C5 C6 H6 108.3 . . ?
 C7 C6 C5 109.92(15) . . ?
 C7 C6 H6 108.3 . . ?
 C7 C6 C11 110.26(15) . . ?
 C11 C6 C5 111.60(14) . . ?
 C11 C6 H6 108.3 . . ?
 O3 C7 C6 121.65(17) . . ?
 O3 C7 C8 120.96(18) . . ?
 C8 C7 C6 117.36(17) . . ?
 C7 C8 H8 119.7 . . ?
 C9 C8 C7 120.59(19) . . ?
 C9 C8 H8 119.7 . . ?
 C8 C9 H9 118.5 . . ?
 C8 C9 C10 123.02(18) . . ?
 C10 C9 H9 118.5 . . ?
 O2 C10 C1 102.60(14) . . ?
 O2 C10 C5 109.66(13) . . ?
 O2 C10 C9 107.85(15) . . ?
 C1 C10 C5 113.58(16) . . ?
 C9 C10 C1 111.65(16) . . ?
 C9 C10 C5 111.01(15) . . ?
 C6 C11 H11 107.7 . . ?
 C12 C11 C6 110.13(14) . . ?
 C12 C11 H11 107.7 . . ?
 C12 C11 C13 110.04(16) . . ?
 C13 C11 C6 113.49(16) . . ?
 C13 C11 H11 107.7 . . ?
 O2 C12 C11 113.88(15) . . ?
 O2 C12 H12A 108.8 . . ?
 O2 C12 H12B 108.8 . . ?
 C11 C12 H12A 108.8 . . ?
 C11 C12 H12B 108.8 . . ?
 H12A C12 H12B 107.7 . . ?
 C11 C13 H13A 109.5 . . ?
 C11 C13 H13B 109.5 . . ?
 C11 C13 H13C 109.5 . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?
 C4 C14 H14A 109.5 . . ?
 C4 C14 H14B 109.5 . . ?
 C4 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 C5 C15 H15A 109.5 . . ?
 C5 C15 H15B 109.5 . . ?
 C5 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
