data_mjl18129_0m
_audit_creation_date               2018-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number       '2016/6'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_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           'C19 H26 O3'
_chemical_formula_sum              'C19 H26 O3'
_chemical_formula_weight           302.40
_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' 0.0148 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' 0.0412 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             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
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                     6.36880(10)
_cell_length_b                     12.2935(2)
_cell_length_c                     21.2458(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1663.44(5)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7886
_cell_measurement_temperature      170(2)
_cell_measurement_theta_max        54.75
_cell_measurement_theta_min        3.615
_shelx_estimated_absorpt_T_max     0.996
_shelx_estimated_absorpt_T_min     0.953
_exptl_absorpt_coefficient_mu      0.408
_exptl_absorpt_correction_T_max    0.7508
_exptl_absorpt_correction_T_min    0.4957
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1523 before and 0.0897 after correction. The Ratio of minimum to maximum transmission is 0.6602. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'colourless'
_exptl_crystal_density_diffrn      1.207
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         'prism'
_exptl_crystal_F_000               656
_exptl_crystal_size_max            0.12
_exptl_crystal_size_mid            0.03
_exptl_crystal_size_min            0.01
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0380
_diffrn_reflns_av_unetI/netI       0.0361
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         14
_diffrn_reflns_limit_k_min         -14
_diffrn_reflns_limit_l_max         21
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              10236
_diffrn_reflns_point_group_measured_fraction_full  0.991
_diffrn_reflns_point_group_measured_fraction_max  0.990
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           54.847
_diffrn_reflns_theta_min           3.620
_diffrn_ambient_temperature        169.99
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_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           0.704
_reflns_Friedel_fraction_full      0.983
_reflns_Friedel_fraction_max       0.981
_reflns_number_gt                  2917
_reflns_number_total               3118
_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           0.162
_refine_diff_density_min           -0.225
_refine_diff_density_rms           0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1153 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.03(13)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.095
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       202
_refine_ls_number_reflns           3118
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0460
_refine_ls_R_factor_gt             0.0423
_refine_ls_restrained_S_all        1.095
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0522P)²+0.3788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1025
_refine_ls_wR_factor_ref           0.1062
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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 0.8343(3) 0.34082(14) 0.63491(8) 0.0399(5) Uani 1 1 d . . . . .
 O2 O 0.5090(3) 0.13960(15) 0.59570(9) 0.0408(5) Uani 1 1 d . . . . .
 O3 O 1.0066(3) 0.10638(16) 0.47772(9) 0.0455(5) Uani 1 1 d . . . . .
 C1 C 0.6161(4) 0.12749(19) 0.78685(11) 0.0315(6) Uani 1 1 d . . . . .
 H1A H 0.572562 0.092705 0.746906 0.038 Uiso 1 1 calc R . . . .
 H1B H 0.750743 0.094380 0.800113 0.038 Uiso 1 1 calc R . . . .
 C2 C 0.4496(4) 0.1064(2) 0.83719(12) 0.0356(6) Uani 1 1 d . . . . .
 H2A H 0.438956 0.027029 0.844526 0.043 Uiso 1 1 calc R . . . .
 H2B H 0.311812 0.131910 0.821465 0.043 Uiso 1 1 calc R . . . .
 C3 C 0.4973(5) 0.16301(19) 0.89978(11) 0.0351(6) Uani 1 1 d . . . . .
 H3A H 0.626487 0.131059 0.917970 0.042 Uiso 1 1 calc R . . . .
 H3B H 0.380728 0.148735 0.929468 0.042 Uiso 1 1 calc R . . . .
 C4 C 0.5273(4) 0.28733(18) 0.89343(11) 0.0280(5) Uani 1 1 d . . . . .
 C5 C 0.6899(4) 0.30342(17) 0.84100(11) 0.0250(5) Uani 1 1 d . . . . .
 H5 H 0.817508 0.264891 0.856976 0.030 Uiso 1 1 calc R . . . .
 C6 C 0.7690(4) 0.41771(18) 0.82544(12) 0.0293(5) Uani 1 1 d . . . . .
 H6A H 0.863437 0.445063 0.858899 0.035 Uiso 1 1 calc R . . . .
 H6B H 0.650330 0.469005 0.820435 0.035 Uiso 1 1 calc R . . . .
 C7 C 0.8888(4) 0.40348(18) 0.76285(11) 0.0286(5) Uani 1 1 d . . . . .
 H7A H 1.039946 0.419213 0.768719 0.034 Uiso 1 1 calc R . . . .
 H7B H 0.832284 0.453354 0.730416 0.034 Uiso 1 1 calc R . . . .
 C8 C 0.8565(4) 0.28356(17) 0.74280(11) 0.0253(5) Uani 1 1 d . . . . .
 H8 H 0.972651 0.239698 0.761720 0.030 Uiso 1 1 calc R . . . .
 C9 C 0.8641(4) 0.26747(18) 0.67199(11) 0.0280(5) Uani 1 1 d . . . . .
 C10 C 0.6478(4) 0.24975(17) 0.77605(10) 0.0246(5) Uani 1 1 d . . . . .
 C11 C 0.9193(4) 0.15385(19) 0.64970(11) 0.0307(5) Uani 1 1 d . . . . .
 H11A H 1.070103 0.140581 0.657935 0.037 Uiso 1 1 calc R . . . .
 H11B H 0.838010 0.100508 0.674703 0.037 Uiso 1 1 calc R . . . .
 C12 C 0.8766(4) 0.13462(18) 0.58122(11) 0.0276(5) Uani 1 1 d . . . . .
 C13 C 0.6600(4) 0.13176(18) 0.55933(11) 0.0297(5) Uani 1 1 d . . . . .
 C14 C 0.6392(5) 0.1182(2) 0.49186(12) 0.0385(6) Uani 1 1 d . . . . .
 H14 H 0.503484 0.117206 0.473286 0.046 Uiso 1 1 calc R . . . .
 C15 C 0.8081(5) 0.1071(2) 0.45576(13) 0.0445(7) Uani 1 1 d . . . . .
 H15 H 0.787756 0.099233 0.411696 0.053 Uiso 1 1 calc R . . . .
 C16 C 1.0331(4) 0.12124(19) 0.54069(12) 0.0346(6) Uani 1 1 d . . . . .
 H16 H 1.172409 0.122088 0.556653 0.042 Uiso 1 1 calc R . . . .
 C18 C 0.6212(4) 0.3321(2) 0.95474(12) 0.0374(6) Uani 1 1 d . . . . .
 H18A H 0.760154 0.299963 0.961603 0.056 Uiso 1 1 calc GR . . . .
 H18B H 0.529008 0.313548 0.990080 0.056 Uiso 1 1 calc GR . . . .
 H18C H 0.634362 0.411341 0.951681 0.056 Uiso 1 1 calc GR . . . .
 C19 C 0.3163(4) 0.3442(2) 0.88306(12) 0.0354(6) Uani 1 1 d . . . . .
 H19A H 0.340697 0.420253 0.871245 0.053 Uiso 1 1 calc GR . . . .
 H19B H 0.233882 0.341551 0.921986 0.053 Uiso 1 1 calc GR . . . .
 H19C H 0.239237 0.307345 0.849326 0.053 Uiso 1 1 calc GR . . . .
 C20 C 0.4625(4) 0.2975(2) 0.73898(12) 0.0315(5) Uani 1 1 d . . . . .
 H20A H 0.330391 0.276401 0.759268 0.047 Uiso 1 1 calc GR . . . .
 H20B H 0.465043 0.269478 0.695798 0.047 Uiso 1 1 calc GR . . . .
 H20C H 0.473711 0.376951 0.738222 0.047 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 C9 1.212(3) . ?
 O2 C13 1.237(3) . ?
 O3 C15 1.347(4) . ?
 O3 C16 1.361(3) . ?
 C1 H1A 0.9900 . ?
 C1 H1B 0.9900 . ?
 C1 C2 1.529(4) . ?
 C1 C10 1.534(3) . ?
 C2 H2A 0.9900 . ?
 C2 H2B 0.9900 . ?
 C2 C3 1.532(3) . ?
 C3 H3A 0.9900 . ?
 C3 H3B 0.9900 . ?
 C3 C4 1.546(3) . ?
 C4 C5 1.534(3) . ?
 C4 C18 1.535(3) . ?
 C4 C19 1.531(3) . ?
 C5 H5 1.0000 . ?
 C5 C6 1.529(3) . ?
 C5 C10 1.553(3) . ?
 C6 H6A 0.9900 . ?
 C6 H6B 0.9900 . ?
 C6 C7 1.543(3) . ?
 C7 H7A 0.9900 . ?
 C7 H7B 0.9900 . ?
 C7 C8 1.548(3) . ?
 C8 H8 1.0000 . ?
 C8 C9 1.518(3) . ?
 C8 C10 1.562(3) . ?
 C9 C11 1.516(3) . ?
 C10 C20 1.535(3) . ?
 C11 H11A 0.9900 . ?
 C11 H11B 0.9900 . ?
 C11 C12 1.499(3) . ?
 C12 C13 1.456(3) . ?
 C12 C16 1.327(3) . ?
 C13 C14 1.449(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.329(4) . ?
 C15 H15 0.9500 . ?
 C16 H16 0.9500 . ?
 C18 H18A 0.9800 . ?
 C18 H18B 0.9800 . ?
 C18 H18C 0.9800 . ?
 C19 H19A 0.9800 . ?
 C19 H19B 0.9800 . ?
 C19 H19C 0.9800 . ?
 C20 H20A 0.9800 . ?
 C20 H20B 0.9800 . ?
 C20 H20C 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
 C15 O3 C16 117.1(2) . . ?
 H1A C1 H1B 108.0 . . ?
 C2 C1 H1A 109.4 . . ?
 C2 C1 H1B 109.4 . . ?
 C2 C1 C10 111.25(19) . . ?
 C10 C1 H1A 109.4 . . ?
 C10 C1 H1B 109.4 . . ?
 C1 C2 H2A 109.0 . . ?
 C1 C2 H2B 109.0 . . ?
 C1 C2 C3 113.1(2) . . ?
 H2A C2 H2B 107.8 . . ?
 C3 C2 H2A 109.0 . . ?
 C3 C2 H2B 109.0 . . ?
 C2 C3 H3A 108.9 . . ?
 C2 C3 H3B 108.9 . . ?
 C2 C3 C4 113.47(19) . . ?
 H3A C3 H3B 107.7 . . ?
 C4 C3 H3A 108.9 . . ?
 C4 C3 H3B 108.9 . . ?
 C5 C4 C3 105.92(19) . . ?
 C5 C4 C18 107.89(19) . . ?
 C18 C4 C3 109.2(2) . . ?
 C19 C4 C3 110.8(2) . . ?
 C19 C4 C5 115.41(19) . . ?
 C19 C4 C18 107.5(2) . . ?
 C4 C5 H5 103.9 . . ?
 C4 C5 C10 118.29(19) . . ?
 C6 C5 C4 119.87(19) . . ?
 C6 C5 H5 103.9 . . ?
 C6 C5 C10 104.79(18) . . ?
 C10 C5 H5 103.9 . . ?
 C5 C6 H6A 110.9 . . ?
 C5 C6 H6B 110.9 . . ?
 C5 C6 C7 104.18(18) . . ?
 H6A C6 H6B 108.9 . . ?
 C7 C6 H6A 110.9 . . ?
 C7 C6 H6B 110.9 . . ?
 C6 C7 H7A 110.5 . . ?
 C6 C7 H7B 110.5 . . ?
 C6 C7 C8 106.23(18) . . ?
 H7A C7 H7B 108.7 . . ?
 C8 C7 H7A 110.5 . . ?
 C8 C7 H7B 110.5 . . ?
 C7 C8 H8 107.7 . . ?
 C7 C8 C10 104.01(18) . . ?
 C9 C8 C7 113.11(19) . . ?
 C9 C8 H8 107.7 . . ?
 C9 C8 C10 116.16(19) . . ?
 C10 C8 H8 107.7 . . ?
 O1 C9 C8 122.8(2) . . ?
 O1 C9 C11 121.2(2) . . ?
 C11 C9 C8 115.91(19) . . ?
 C1 C10 C5 107.82(18) . . ?
 C1 C10 C8 116.12(18) . . ?
 C1 C10 C20 110.5(2) . . ?
 C5 C10 C8 98.15(17) . . ?
 C20 C10 C5 115.24(19) . . ?
 C20 C10 C8 108.70(18) . . ?
 C9 C11 H11A 108.8 . . ?
 C9 C11 H11B 108.8 . . ?
 H11A C11 H11B 107.7 . . ?
 C12 C11 C9 114.0(2) . . ?
 C12 C11 H11A 108.8 . . ?
 C12 C11 H11B 108.8 . . ?
 C13 C12 C11 119.0(2) . . ?
 C16 C12 C11 120.9(2) . . ?
 C16 C12 C13 120.1(2) . . ?
 O2 C13 C12 122.3(2) . . ?
 O2 C13 C14 123.7(2) . . ?
 C14 C13 C12 113.9(2) . . ?
 C13 C14 H14 119.7 . . ?
 C15 C14 C13 120.6(3) . . ?
 C15 C14 H14 119.7 . . ?
 O3 C15 H15 117.9 . . ?
 C14 C15 O3 124.1(3) . . ?
 C14 C15 H15 117.9 . . ?
 O3 C16 H16 117.9 . . ?
 C12 C16 O3 124.1(2) . . ?
 C12 C16 H16 117.9 . . ?
 C4 C18 H18A 109.5 . . ?
 C4 C18 H18B 109.5 . . ?
 C4 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 C4 C19 H19A 109.5 . . ?
 C4 C19 H19B 109.5 . . ?
 C4 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 C10 C20 H20A 109.5 . . ?
 C10 C20 H20B 109.5 . . ?
 C10 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
