data_global
_publ_requested_journal          Org.Lett.
_publ_contact_author_name        'Stephen J. Connon'
_publ_contact_author_address     
;Trinity Biomedical Sciences Institute, 
School of Chemistry, 
The University of Dublin, 
Trinity College, 
Dublin 2, 
Ireland
;
_publ_contact_author_email       'connons@tcd.ie '
loop_
_publ_author_name
_publ_author_address
'Aiello, Maria Luisa '
;Trinity Biomedical Sciences Institute, 
School of Chemistry, 
The University of Dublin, 
Trinity College, 
Dublin 2, 
Ireland
;
'Farid, Umar'
;Trinity Biomedical Sciences Institute, 
School of Chemistry, 
The University of Dublin, 
Trinity College, 
Dublin 2, 
Ireland
;
'Trujillo, Cristina'
;Trinity Biomedical Sciences Institute, 
School of Chemistry, 
The University of Dublin, 
Trinity College, 
Dublin 2, 
Ireland
;
'Twamley, Brendan'
;School of Chemistry, 
The University of Dublin, 
Trinity College, 
Dublin 2, 
Ireland
;
'Connon, Stephen J.'
;Trinity Biomedical Sciences Institute
School of Chemistry, 
The University of Dublin, 
Trinity College, 
Dublin 2, 
Ireland
;



data_tcd838
_audit_creation_date               2018-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bruker (2013). SAINT v8.37A, Bruker AXS Inc., Madison, WI, USA.

Bruker (2016). APEX3 v2016.9-0, Bruker AXS Inc., Madison, WI, USA.

Bruker (2016/2). SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.

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. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C15 H18 O4'
_chemical_formula_sum              'C15 H18 O4'
_chemical_formula_weight           262.29
_chemical_absolute_configuration   ad
_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' 0.0181 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'

_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                     9.1791(4)
_cell_length_b                     9.4637(4)
_cell_length_c                     15.3758(7)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1335.67(10)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9390
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        70.01
_cell_measurement_theta_min        2.87
_shelx_estimated_absorpt_T_max     0.927
_shelx_estimated_absorpt_T_min     0.733
_exptl_absorpt_coefficient_mu      0.772
_exptl_absorpt_correction_T_max    0.7533
_exptl_absorpt_correction_T_min    0.6450
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1121 before and 0.0348 after correction. The Ratio of minimum to maximum transmission is 0.8139. 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      1.304
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         'block fragment'
_exptl_crystal_F_000               560
_exptl_crystal_size_max            0.43
_exptl_crystal_size_mid            0.36
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0393
_diffrn_reflns_av_unetI/netI       0.0185
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.989
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -18
_diffrn_reflns_number              19493
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.984
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           70.004
_diffrn_reflns_theta_min           5.489
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CCD area detector'
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.989
_diffrn_measurement_device         'Kappa diffractometer'
_diffrn_measurement_device_type    'Bruker SMART APEX2 area detector'
_diffrn_measurement_method         'ω and φ scans'
_diffrn_radiation_detector         APEX2
_diffrn_radiation_monochromator    'mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_target              Mok\a
_diffrn_source_type                'Incoatec I\ms'
_diffrn_standards_number           .
_reflns_Friedel_coverage           0.711
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       0.978
_reflns_number_gt                  2498
_reflns_number_total               2503
_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         'APEX 3 (Bruker, 2016) '
_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    'XL (Sheldrick, 2008)'
_computing_structure_solution      'XT (Sheldrick, 2015)'
_refine_diff_density_max           0.171
_refine_diff_density_min           -0.128
_refine_diff_density_rms           0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.00(3)
_refine_ls_extinction_coef         0.0085(7)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       176
_refine_ls_number_reflns           2503
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0243
_refine_ls_R_factor_gt             0.0242
_refine_ls_restrained_S_all        1.063
_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)+(0.0372P)²+0.2383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0657
_refine_ls_wR_factor_ref           0.0658
_refine_special_details           
 'The model has Chirality at C10 and C15 (Chiral SPGR) and both are assigned as R'
_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:
 C10(H10), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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 0.45673(12) 0.79852(10) 0.44295(7) 0.0181(2) Uani 1 1 d . . . . .
 O3 O 0.38973(12) 0.98246(11) 0.52088(8) 0.0244(3) Uani 1 1 d . . . . .
 O12 O 0.28381(12) 0.56551(12) 0.54194(7) 0.0235(3) Uani 1 1 d . . . . .
 O13 O 0.40018(12) 0.37534(11) 0.49005(7) 0.0226(3) Uani 1 1 d . . . . .
 C2 C 0.45680(16) 0.87205(15) 0.51760(10) 0.0181(3) Uani 1 1 d . . . . .
 C4 C 0.53233(15) 0.80997(16) 0.59394(10) 0.0178(3) Uani 1 1 d . . . . .
 C5 C 0.55754(17) 0.89394(17) 0.66693(10) 0.0220(3) Uani 1 1 d . . . . .
 H5 H 0.5331 0.9915 0.6658 0.026 Uiso 1 1 calc R . . . .
 C6 C 0.61803(17) 0.83537(18) 0.74101(10) 0.0250(3) Uani 1 1 d . . . . .
 H6 H 0.6356 0.8926 0.7907 0.030 Uiso 1 1 calc R . . . .
 C7 C 0.65306(17) 0.6922(2) 0.74255(11) 0.0260(4) Uani 1 1 d . . . . .
 H7 H 0.6933 0.6514 0.7937 0.031 Uiso 1 1 calc R . . . .
 C8 C 0.62934(17) 0.60883(18) 0.66968(10) 0.0228(3) Uani 1 1 d . . . . .
 H8 H 0.6543 0.5114 0.6710 0.027 Uiso 1 1 calc R . . . .
 C9 C 0.56939(15) 0.66683(16) 0.59480(10) 0.0174(3) Uani 1 1 d . . . . .
 C10 C 0.54255(16) 0.58046(15) 0.51359(10) 0.0171(3) Uani 1 1 d . . . . .
 H10 H 0.6192 0.5057 0.5094 0.021 Uiso 1 1 calc R . . . .
 C11 C 0.39395(16) 0.50948(15) 0.51743(9) 0.0165(3) Uani 1 1 d . . . . .
 C14 C 0.26186(18) 0.30082(17) 0.49093(11) 0.0249(3) Uani 1 1 d . . . . .
 H14A H 0.1914 0.3516 0.4546 0.037 Uiso 1 1 calc GR . . . .
 H14B H 0.2253 0.2955 0.5507 0.037 Uiso 1 1 calc GR . . . .
 H14C H 0.2756 0.2051 0.4680 0.037 Uiso 1 1 calc GR . . . .
 C15 C 0.55598(16) 0.67875(15) 0.43472(9) 0.0168(3) Uani 1 1 d . . . . .
 H15 H 0.6579 0.7160 0.4327 0.020 Uiso 1 1 calc R . . . .
 C16 C 0.52247(17) 0.61030(16) 0.34778(10) 0.0191(3) Uani 1 1 d . . . . .
 H16A H 0.4208 0.5754 0.3489 0.023 Uiso 1 1 calc R . . . .
 H16B H 0.5870 0.5273 0.3404 0.023 Uiso 1 1 calc R . . . .
 C17 C 0.54110(16) 0.70751(15) 0.26876(9) 0.0183(3) Uani 1 1 d . . . . .
 H17 H 0.4710 0.7878 0.2748 0.022 Uiso 1 1 calc R . . . .
 C18 C 0.69507(17) 0.76892(18) 0.26255(10) 0.0220(3) Uani 1 1 d . . . . .
 H18A H 0.7139 0.8289 0.3133 0.033 Uiso 1 1 calc GR . . . .
 H18B H 0.7036 0.8255 0.2094 0.033 Uiso 1 1 calc GR . . . .
 H18C H 0.7662 0.6917 0.2610 0.033 Uiso 1 1 calc GR . . . .
 C19 C 0.50346(17) 0.62702(17) 0.18560(10) 0.0225(3) Uani 1 1 d . . . . .
 H19A H 0.5068 0.6918 0.1359 0.034 Uiso 1 1 calc GR . . . .
 H19B H 0.4054 0.5870 0.1907 0.034 Uiso 1 1 calc GR . . . .
 H19C H 0.5740 0.5506 0.1768 0.034 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 C2 1.3423(18) . ?
 O1 C15 1.4596(18) . ?
 O3 C2 1.2139(19) . ?
 O12 C11 1.2022(19) . ?
 O13 C11 1.3387(18) . ?
 O13 C14 1.4525(19) . ?
 C2 C4 1.484(2) . ?
 C4 C5 1.395(2) . ?
 C4 C9 1.397(2) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.383(2) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.393(3) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.387(2) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.389(2) . ?
 C9 C10 1.513(2) . ?
 C10 H10 1.0000 . ?
 C10 C11 1.522(2) . ?
 C10 C15 1.5334(19) . ?
 C14 H14A 0.9800 . ?
 C14 H14B 0.9800 . ?
 C14 H14C 0.9800 . ?
 C15 H15 1.0000 . ?
 C15 C16 1.5169(19) . ?
 C16 H16A 0.9900 . ?
 C16 H16B 0.9900 . ?
 C16 C17 1.534(2) . ?
 C17 H17 1.0000 . ?
 C17 C18 1.531(2) . ?
 C17 C19 1.528(2) . ?
 C18 H18A 0.9800 . ?
 C18 H18B 0.9800 . ?
 C18 H18C 0.9800 . ?
 C19 H19A 0.9800 . ?
 C19 H19B 0.9800 . ?
 C19 H19C 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
 C2 O1 C15 118.45(11) . . ?
 C11 O13 C14 114.85(12) . . ?
 O1 C2 C4 118.11(12) . . ?
 O3 C2 O1 118.79(14) . . ?
 O3 C2 C4 123.01(14) . . ?
 C5 C4 C2 119.23(13) . . ?
 C5 C4 C9 120.31(14) . . ?
 C9 C4 C2 120.34(13) . . ?
 C4 C5 H5 120.0 . . ?
 C6 C5 C4 120.07(15) . . ?
 C6 C5 H5 120.0 . . ?
 C5 C6 H6 120.1 . . ?
 C5 C6 C7 119.77(15) . . ?
 C7 C6 H6 120.1 . . ?
 C6 C7 H7 119.9 . . ?
 C8 C7 C6 120.21(15) . . ?
 C8 C7 H7 119.9 . . ?
 C7 C8 H8 119.8 . . ?
 C7 C8 C9 120.45(15) . . ?
 C9 C8 H8 119.8 . . ?
 C4 C9 C10 118.46(13) . . ?
 C8 C9 C4 119.18(14) . . ?
 C8 C9 C10 122.36(13) . . ?
 C9 C10 H10 108.7 . . ?
 C9 C10 C11 110.65(12) . . ?
 C9 C10 C15 108.18(11) . . ?
 C11 C10 H10 108.7 . . ?
 C11 C10 C15 111.75(12) . . ?
 C15 C10 H10 108.7 . . ?
 O12 C11 O13 123.56(14) . . ?
 O12 C11 C10 124.84(13) . . ?
 O13 C11 C10 111.60(12) . . ?
 O13 C14 H14A 109.5 . . ?
 O13 C14 H14B 109.5 . . ?
 O13 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 O1 C15 C10 110.63(11) . . ?
 O1 C15 H15 108.2 . . ?
 O1 C15 C16 106.35(11) . . ?
 C10 C15 H15 108.2 . . ?
 C16 C15 C10 114.93(12) . . ?
 C16 C15 H15 108.2 . . ?
 C15 C16 H16A 108.6 . . ?
 C15 C16 H16B 108.6 . . ?
 C15 C16 C17 114.79(12) . . ?
 H16A C16 H16B 107.5 . . ?
 C17 C16 H16A 108.6 . . ?
 C17 C16 H16B 108.6 . . ?
 C16 C17 H17 108.1 . . ?
 C18 C17 C16 112.33(12) . . ?
 C18 C17 H17 108.1 . . ?
 C19 C17 C16 109.80(12) . . ?
 C19 C17 H17 108.1 . . ?
 C19 C17 C18 110.24(12) . . ?
 C17 C18 H18A 109.5 . . ?
 C17 C18 H18B 109.5 . . ?
 C17 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 C17 C19 H19A 109.5 . . ?
 C17 C19 H19B 109.5 . . ?
 C17 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?

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
 C10 H10 O3 1.00 2.53 3.2851(19) 132 4_566
 C14 H14C O3 0.98 2.49 3.266(2) 136 1_545
 C15 H15 O12 1.00 2.40 3.2187(18) 139 4_566
 C18 H18A O12 0.98 2.52 3.4864(19) 168 4_566

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 C2 C4 C5 168.27(13) . . . . ?
 O1 C2 C4 C9 -15.8(2) . . . . ?
 O1 C15 C16 C17 59.24(16) . . . . ?
 O3 C2 C4 C5 -15.3(2) . . . . ?
 O3 C2 C4 C9 160.65(14) . . . . ?
 C2 O1 C15 C10 49.93(16) . . . . ?
 C2 O1 C15 C16 175.38(11) . . . . ?
 C2 C4 C5 C6 175.25(14) . . . . ?
 C2 C4 C9 C8 -174.85(14) . . . . ?
 C2 C4 C9 C10 5.2(2) . . . . ?
 C4 C5 C6 C7 -0.3(2) . . . . ?
 C4 C9 C10 C11 -92.94(15) . . . . ?
 C4 C9 C10 C15 29.78(17) . . . . ?
 C5 C4 C9 C8 1.1(2) . . . . ?
 C5 C4 C9 C10 -178.92(13) . . . . ?
 C5 C6 C7 C8 0.9(2) . . . . ?
 C6 C7 C8 C9 -0.5(2) . . . . ?
 C7 C8 C9 C4 -0.4(2) . . . . ?
 C7 C8 C9 C10 179.55(14) . . . . ?
 C8 C9 C10 C11 87.08(16) . . . . ?
 C8 C9 C10 C15 -150.20(14) . . . . ?
 C9 C4 C5 C6 -0.7(2) . . . . ?
 C9 C10 C11 O12 43.0(2) . . . . ?
 C9 C10 C11 O13 -136.90(12) . . . . ?
 C9 C10 C15 O1 -55.83(15) . . . . ?
 C9 C10 C15 C16 -176.27(12) . . . . ?
 C10 C15 C16 C17 -177.99(12) . . . . ?
 C11 C10 C15 O1 66.22(15) . . . . ?
 C11 C10 C15 C16 -54.23(16) . . . . ?
 C14 O13 C11 O12 0.7(2) . . . . ?
 C14 O13 C11 C10 -179.37(13) . . . . ?
 C15 O1 C2 O3 170.13(13) . . . . ?
 C15 O1 C2 C4 -13.29(18) . . . . ?
 C15 C10 C11 O12 -77.59(19) . . . . ?
 C15 C10 C11 O13 102.48(13) . . . . ?
 C15 C16 C17 C18 57.30(17) . . . . ?
 C15 C16 C17 C19 -179.66(13) . . . . ?

_olex2_exptl_crystal_mounting_method  'mounted in oil on a MiTeGen holder'
_olex2_submission_original_sample_id  MLA438
_olex2_submission_special_instructions  'No special instructions were received'
