# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ncb-72
_database_code_depnum_ccdc_archive 'CCDC 1861719'
_audit_update_record             
;
2018-08-12 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
_audit_creation_date             2018-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H18 O3'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_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 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.0433(12)
_cell_length_b                   7.9515(14)
_cell_length_c                   13.619(2)
_cell_angle_alpha                83.665(14)
_cell_angle_beta                 80.712(14)
_cell_angle_gamma                66.771(16)
_cell_volume                     690.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    696
_cell_measurement_temperature    294.98(10)
_cell_measurement_theta_max      22.7720
_cell_measurement_theta_min      4.0920
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4503
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      294.98(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   47.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   60.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00   53.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000   30.0000 102
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0608726000
_diffrn_orient_matrix_UB_12      -0.0360702000
_diffrn_orient_matrix_UB_13      0.0358614000
_diffrn_orient_matrix_UB_21      -0.0879097000
_diffrn_orient_matrix_UB_22      0.0475186000
_diffrn_orient_matrix_UB_23      -0.0255405000
_diffrn_orient_matrix_UB_31      0.0279206000
_diffrn_orient_matrix_UB_32      -0.0767393000
_diffrn_orient_matrix_UB_33      -0.0292260000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1433
_reflns_number_total             2714
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0622P)²+0.2325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1918
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.2154(4) 1.2575(3) 0.33977(18) 0.0612(7) Uani 1 d . . .
H1 H -0.2965 1.3630 0.3293 0.092 Uiso 1 calc . . GR
O2 O 0.0546(4) 0.8135(3) 0.42157(18) 0.0619(7) Uani 1 d . . .
O3 O 0.5308(4) 0.6154(3) 0.33351(17) 0.0574(7) Uani 1 d . . .
C1 C 0.0720(5) 0.9096(4) 0.3481(2) 0.0404(7) Uani 1 d . . .
C2 C 0.2463(5) 0.9762(4) 0.3264(3) 0.0484(8) Uani 1 d . . .
H2A H 0.1877 1.1091 0.3242 0.058 Uiso 1 calc . . R
H2B H 0.3203 0.9386 0.2610 0.058 Uiso 1 calc . . R
C3 C 0.4003(5) 0.9071(4) 0.4014(3) 0.0504(9) Uani 1 d . . .
H3A H 0.4870 0.9783 0.3911 0.060 Uiso 1 calc . . R
H3B H 0.3237 0.9287 0.4677 0.060 Uiso 1 calc . . R
C4 C 0.5384(5) 0.7086(4) 0.3968(2) 0.0419(7) Uani 1 d . . .
C5 C -0.0783(5) 0.8448(4) 0.2068(2) 0.0413(7) Uani 1 d . . .
C6 C -0.2201(5) 0.9066(4) 0.1369(2) 0.0447(8) Uani 1 d . . .
C7 C -0.3621(5) 1.0866(4) 0.1385(3) 0.0533(9) Uani 1 d . . .
H7 H -0.4579 1.1276 0.0929 0.064 Uiso 1 calc . . R
C8 C -0.3671(5) 1.2070(4) 0.2050(3) 0.0516(9) Uani 1 d . . .
H8 H -0.4651 1.3268 0.2046 0.062 Uiso 1 calc . . R
C9 C -0.2248(5) 1.1475(4) 0.2720(2) 0.0439(8) Uani 1 d . . .
C10 C -0.0809(4) 0.9671(3) 0.2734(2) 0.0380(7) Uani 1 d . . .
C11 C -0.2178(5) 0.7857(4) 0.0594(3) 0.0537(9) Uani 1 d . . .
C12 C -0.3139(9) 0.6627(6) 0.0833(4) 0.0875(16) Uani 1 d . . .
H12A H -0.314(5) 0.595(4) 0.034(3) 0.069(11) Uiso 1 d . . .
H12B H -0.350(9) 0.637(7) 0.147(4) 0.13(2) Uiso 1 d . . .
C13 C -0.1232(7) 0.8104(6) -0.0383(3) 0.0869(13) Uani 1 d . . .
H13A H -0.1877 0.9358 -0.0617 0.130 Uiso 1 calc . . GR
H13B H -0.1406 0.7319 -0.0819 0.130 Uiso 1 calc . . GR
H13C H 0.0226 0.7801 -0.0374 0.130 Uiso 1 calc . . GR
C14 C 0.0818(6) 0.6506(4) 0.2084(3) 0.0625(10) Uani 1 d . . .
H14A H 0.1964 0.6450 0.2402 0.094 Uiso 1 calc . . GR
H14B H 0.1313 0.6126 0.1413 0.094 Uiso 1 calc . . GR
H14C H 0.0193 0.5707 0.2446 0.094 Uiso 1 calc . . GR
C15 C 0.6859(6) 0.6306(4) 0.4722(3) 0.0592(10) Uani 1 d . . .
H15A H 0.7427 0.4993 0.4715 0.089 Uiso 1 calc . . GR
H15B H 0.6134 0.6677 0.5371 0.089 Uiso 1 calc . . GR
H15C H 0.7967 0.6745 0.4566 0.089 Uiso 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 C9 1.366(3) . ?
O2 C1 1.211(3) . ?
O3 C4 1.218(3) . ?
C1 C2 1.495(4) . ?
C1 C10 1.505(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.512(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.494(4) . ?
C4 C15 1.487(4) . ?
C5 C6 1.401(4) . ?
C5 C10 1.395(4) . ?
C5 C14 1.511(4) . ?
C6 C7 1.386(4) . ?
C6 C11 1.498(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(4) . ?
C9 C10 1.392(4) . ?
C11 C12 1.379(5) . ?
C11 C13 1.419(5) . ?
C12 H12A 0.91(4) . ?
C12 H12B 0.89(6) . ?
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
C9 O1 H1 109.5 . . ?
O2 C1 C2 122.0(3) . . ?
O2 C1 C10 121.5(3) . . ?
C2 C1 C10 116.6(3) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C1 C2 C3 114.2(3) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 C2 114.8(2) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
O3 C4 C3 121.1(3) . . ?
O3 C4 C15 121.6(3) . . ?
C15 C4 C3 117.2(3) . . ?
C6 C5 C14 121.0(3) . . ?
C10 C5 C6 119.1(2) . . ?
C10 C5 C14 119.8(3) . . ?
C5 C6 C11 121.9(3) . . ?
C7 C6 C5 118.5(3) . . ?
C7 C6 C11 119.6(3) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 C6 122.6(3) . . ?
C8 C7 H7 118.7 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 H8 120.6 . . ?
O1 C9 C8 123.2(3) . . ?
O1 C9 C10 116.5(3) . . ?
C8 C9 C10 120.3(3) . . ?
C5 C10 C1 121.4(2) . . ?
C9 C10 C1 118.0(2) . . ?
C9 C10 C5 120.6(3) . . ?
C12 C11 C6 120.0(4) . . ?
C12 C11 C13 122.6(4) . . ?
C13 C11 C6 117.4(3) . . ?
C11 C12 H12A 118(2) . . ?
C11 C12 H12B 119(3) . . ?
H12A C12 H12B 122(4) . . ?
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 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 C9 C10 C1 -0.4(4) . . . . ?
O1 C9 C10 C5 -179.9(3) . . . . ?
O2 C1 C2 C3 2.3(4) . . . . ?
O2 C1 C10 C5 -74.8(4) . . . . ?
O2 C1 C10 C9 105.8(3) . . . . ?
C1 C2 C3 C4 71.7(4) . . . . ?
C2 C1 C10 C5 104.9(3) . . . . ?
C2 C1 C10 C9 -74.5(4) . . . . ?
C2 C3 C4 O3 3.4(5) . . . . ?
C2 C3 C4 C15 -177.0(3) . . . . ?
C5 C6 C7 C8 0.9(5) . . . . ?
C5 C6 C11 C12 82.0(5) . . . . ?
C5 C6 C11 C13 -101.0(4) . . . . ?
C6 C5 C10 C1 -178.2(3) . . . . ?
C6 C5 C10 C9 1.2(4) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C6 C11 C12 -99.9(4) . . . . ?
C7 C6 C11 C13 77.1(4) . . . . ?
C7 C8 C9 O1 179.0(3) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C8 C9 C10 C1 179.7(3) . . . . ?
C8 C9 C10 C5 0.3(5) . . . . ?
C10 C1 C2 C3 -177.3(2) . . . . ?
C10 C5 C6 C7 -1.8(4) . . . . ?
C10 C5 C6 C11 176.4(3) . . . . ?
C11 C6 C7 C8 -177.3(3) . . . . ?
C14 C5 C6 C7 -179.4(3) . . . . ?
C14 C5 C6 C11 -1.3(5) . . . . ?
C14 C5 C10 C1 -0.6(5) . . . . ?
C14 C5 C10 C9 178.9(3) . . . . ?

_olex2_date_sample_data_collection 2018-05-29
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b1116
_database_code_depnum_ccdc_archive 'CCDC 1861720'
_audit_update_record             
;
2018-08-12 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
_audit_creation_date             2018-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H14 O3'
_chemical_formula_sum            'C12 H14 O3'
_chemical_formula_weight         206.23
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2734(2)
_cell_length_b                   12.6013(4)
_cell_length_c                   10.9726(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.864(3)
_cell_angle_gamma                90.00
_cell_volume                     1105.67(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1991
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1380
_cell_measurement_theta_min      5.4540
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4478
_diffrn_reflns_theta_full        66.56
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         5.45
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   37.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -63.00  -36.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   27.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00   59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   63.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega   87.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega   31.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega  -14.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
  9 omega   78.00  117.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   -7.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
 13 omega   68.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   43.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
 15 omega   65.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
 20 omega   61.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
 21 omega   52.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
 22 omega   48.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 23 omega   36.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   35.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0384833000
_diffrn_orient_matrix_UB_12      0.0894999000
_diffrn_orient_matrix_UB_13      0.0988357000
_diffrn_orient_matrix_UB_21      0.0539656000
_diffrn_orient_matrix_UB_22      -0.0830232000
_diffrn_orient_matrix_UB_23      0.1056356000
_diffrn_orient_matrix_UB_31      0.1809697000
_diffrn_orient_matrix_UB_32      0.0057340000
_diffrn_orient_matrix_UB_33      -0.0128561000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1583
_reflns_number_total             1862
_reflns_odcompleteness_completeness 95.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0063(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.1723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1191
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.16048(13) 0.01904(9) 0.84048(11) 0.0538(3) Uani 1 d . . .
O2 O -0.51213(13) 0.06063(11) 0.84546(12) 0.0637(4) Uani 1 d . . .
H2 H -0.6035 0.0555 0.8612 0.096 Uiso 1 calc . . GR
C3 C -0.26098(17) 0.15642(12) 0.90277(14) 0.0419(4) Uani 1 d . . .
O4 O -0.18134(16) 0.14314(11) 0.71126(11) 0.0634(4) Uani 1 d . . .
C5 C -0.1572(2) 0.23235(12) 0.97700(15) 0.0491(4) Uani 1 d . . .
C6 C -0.20528(16) 0.09748(13) 0.80209(13) 0.0427(4) Uani 1 d . . .
C7 C -0.41717(18) 0.13399(12) 0.92392(15) 0.0482(4) Uani 1 d . . .
C8 C -0.17582(18) -0.01983(12) 0.82136(15) 0.0482(4) Uani 1 d . . .
H8A H -0.2828 -0.0548 0.8117 0.058 Uiso 1 calc . . R
H8B H -0.1101 -0.0319 0.9071 0.058 Uiso 1 calc . . R
C9 C -0.4705(2) 0.18628(15) 1.01717(18) 0.0622(5) Uani 1 d . . .
H9 H -0.5755 0.1724 1.0297 0.075 Uiso 1 calc . . R
C10 C -0.0869(2) -0.07028(15) 0.73152(16) 0.0554(4) Uani 1 d . . .
H10A H -0.0893 -0.1468 0.7409 0.067 Uiso 1 calc . . R
H10B H -0.1476 -0.0533 0.6458 0.067 Uiso 1 calc . . R
C11 C 0.09118(19) -0.03549(12) 0.75127(15) 0.0461(4) Uani 1 d . . .
C12 C -0.2117(3) 0.28191(15) 1.07202(18) 0.0638(5) Uani 1 d . . .
H12 H -0.1428 0.3312 1.1235 0.077 Uiso 1 calc . . R
C13 C 0.1804(3) -0.07283(17) 0.65659(19) 0.0692(5) Uani 1 d . . .
H13A H 0.1287 -0.0424 0.5758 0.104 Uiso 1 calc . . GR
H13B H 0.1743 -0.1488 0.6507 0.104 Uiso 1 calc . . GR
H13C H 0.2954 -0.0512 0.6825 0.104 Uiso 1 calc . . GR
C14 C -0.3657(3) 0.25945(16) 1.09143(19) 0.0700(6) Uani 1 d . . .
H14 H -0.3998 0.2941 1.1555 0.084 Uiso 1 calc . . R
C15 C 0.0094(2) 0.26120(16) 0.9542(2) 0.0685(5) Uani 1 d . . .
H15A H 0.0662 0.1978 0.9400 0.103 Uiso 1 calc . . GR
H15B H 0.0759 0.2978 1.0265 0.103 Uiso 1 calc . . GR
H15C H -0.0079 0.3064 0.8815 0.103 Uiso 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 C11 1.2130(19) . ?
O2 H2 0.8200 . ?
O2 C7 1.366(2) . ?
C3 C5 1.399(2) . ?
C3 C6 1.499(2) . ?
C3 C7 1.399(2) . ?
O4 C6 1.2102(18) . ?
C5 C12 1.386(2) . ?
C5 C15 1.507(2) . ?
C6 C8 1.504(2) . ?
C7 C9 1.381(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C10 1.513(2) . ?
C9 H9 0.9300 . ?
C9 C14 1.380(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.498(2) . ?
C11 C13 1.496(2) . ?
C12 H12 0.9300 . ?
C12 C14 1.375(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
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
C7 O2 H2 109.5 . . ?
C5 C3 C6 120.61(13) . . ?
C7 C3 C5 119.78(15) . . ?
C7 C3 C6 119.60(14) . . ?
C3 C5 C15 121.28(15) . . ?
C12 C5 C3 118.46(16) . . ?
C12 C5 C15 120.25(16) . . ?
C3 C6 C8 116.92(12) . . ?
O4 C6 C3 121.18(15) . . ?
O4 C6 C8 121.88(15) . . ?
O2 C7 C3 116.01(14) . . ?
O2 C7 C9 123.25(15) . . ?
C9 C7 C3 120.72(16) . . ?
C6 C8 H8A 108.7 . . ?
C6 C8 H8B 108.7 . . ?
C6 C8 C10 114.18(14) . . ?
H8A C8 H8B 107.6 . . ?
C10 C8 H8A 108.7 . . ?
C10 C8 H8B 108.7 . . ?
C7 C9 H9 120.5 . . ?
C14 C9 C7 118.98(17) . . ?
C14 C9 H9 120.5 . . ?
C8 C10 H10A 108.7 . . ?
C8 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C8 114.03(13) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
O1 C11 C10 121.74(14) . . ?
O1 C11 C13 121.55(15) . . ?
C13 C11 C10 116.70(15) . . ?
C5 C12 H12 119.4 . . ?
C14 C12 C5 121.14(19) . . ?
C14 C12 H12 119.4 . . ?
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 . . ?
C9 C14 H14 119.6 . . ?
C12 C14 C9 120.88(17) . . ?
C12 C14 H14 119.6 . . ?
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 . . ?

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
O2 C7 C9 C14 -179.74(16) . . . . ?
C3 C5 C12 C14 -1.7(3) . . . . ?
C3 C6 C8 C10 -168.12(12) . . . . ?
C3 C7 C9 C14 -1.5(2) . . . . ?
O4 C6 C8 C10 10.1(2) . . . . ?
C5 C3 C6 O4 -64.67(19) . . . . ?
C5 C3 C6 C8 113.54(15) . . . . ?
C5 C3 C7 O2 178.58(13) . . . . ?
C5 C3 C7 C9 0.2(2) . . . . ?
C5 C12 C14 C9 0.4(3) . . . . ?
C6 C3 C5 C12 -177.63(14) . . . . ?
C6 C3 C5 C15 3.1(2) . . . . ?
C6 C3 C7 O2 -2.4(2) . . . . ?
C6 C3 C7 C9 179.20(14) . . . . ?
C6 C8 C10 C11 67.70(19) . . . . ?
C7 C3 C5 C12 1.4(2) . . . . ?
C7 C3 C5 C15 -177.96(15) . . . . ?
C7 C3 C6 O4 116.35(16) . . . . ?
C7 C3 C6 C8 -65.44(17) . . . . ?
C7 C9 C14 C12 1.2(3) . . . . ?
C8 C10 C11 O1 7.6(2) . . . . ?
C8 C10 C11 C13 -173.33(15) . . . . ?
C15 C5 C12 C14 177.66(17) . . . . ?

_olex2_date_sample_data_collection 2018-07-19
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ncb-19
_database_code_depnum_ccdc_archive 'CCDC 1861721'
_audit_update_record             
;
2018-08-12 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
_audit_creation_date             2018-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_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                   10.44121(16)
_cell_length_b                   11.19736(18)
_cell_length_c                   11.71740(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1369.93(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13586
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6600
_cell_measurement_theta_min      4.2020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17862
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.777
_diffrn_reflns_theta_min         5.465
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  39.00   1.00    1.00    --  -41.11  19.00 -90.00  121
  2  ω     23.00  97.00   1.00    1.00    --   41.11-125.00 120.00   74
  3  ω      1.00  82.00   1.00    1.00    --   41.11 -99.00 120.00   81
  4  ω     94.00 178.00   1.00    1.12    --  107.58 125.00 -30.00   84
  5  ω     34.00 122.00   1.00    1.12    --  107.58-125.00-150.00   88
  6  ω    101.00 178.00   1.00    1.12    --  107.58 107.00   1.00   77
  7  ω     94.00 178.00   1.00    1.12    --  107.58 125.00 150.00   84
  8  ω     31.00 136.00   1.00    1.12    --  107.58 -30.00 -30.00  105
  9  ω     78.00 178.00   1.00    1.12    --  107.58  61.00 150.00  100
 10  ω   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00-120.00  108
 11  ω   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00 120.00  108
 12  ω     78.00 178.00   1.00    1.12    --  107.58  61.00  90.00  100
 13  ω     78.00 178.00   1.00    1.12    --  107.58  61.00  30.00  100
 14  ω     75.00 178.00   1.00    1.12    --  107.58  77.00-120.00  103
 15  ω     79.00 178.00   1.00    1.12    --  107.58  30.00 -30.00   99
 16  ω    -69.00  16.00   1.00    1.00    --  -41.11  57.00   0.00   85
 17  ω   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00   0.00  108
 18  ω   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00 -90.00  100
 19  ω   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00-180.00  100
 20  ω   -114.00 -11.00   1.00    1.00    --  -41.23 -66.00 143.00  103
 21  ω   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00  30.00  100
 22  ω   -116.00 -17.00   1.00    1.00    --  -41.23 -38.00 120.00   99
 23  ω   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00 -30.00  108
 24  ω     23.00  97.00   1.00    1.00    --   41.23-125.00-150.00   74
 25  ω     78.00 125.00   1.00    1.12    --  107.58  61.00  60.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0969505000
_diffrn_orient_matrix_UB_12      -0.0507500000
_diffrn_orient_matrix_UB_13      0.0864086000
_diffrn_orient_matrix_UB_21      0.1052060000
_diffrn_orient_matrix_UB_22      -0.0807384000
_diffrn_orient_matrix_UB_23      0.0505805000
_diffrn_orient_matrix_UB_31      0.0361156000
_diffrn_orient_matrix_UB_32      0.0991187000
_diffrn_orient_matrix_UB_33      0.0852581000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2673
_reflns_number_total             2733
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 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         0.211
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_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     168
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.095
_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)+(0.0632P)²+0.1309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0935
_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:
 C15(H15), C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C6(H6A,H6B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C14(H14A,H14B,
 H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O3 O 0.29535(11) 0.48083(11) 0.25598(10) 0.0160(3) Uani 1 1 d . . . . .
O1 O 0.14606(12) 0.55892(12) 0.52035(10) 0.0191(3) Uani 1 1 d . . . . .
H1 H 0.177952 0.557088 0.584278 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.46242(12) 0.62780(11) 0.40921(11) 0.0190(3) Uani 1 1 d . . . . .
C11 C 0.50223(17) 0.52477(16) 0.34423(15) 0.0178(4) Uani 1 1 d . . . . .
C15 C 0.39117(16) 0.43608(15) 0.33546(14) 0.0150(4) Uani 1 1 d . . . . .
H15 H 0.422068 0.357285 0.311647 0.018 Uiso 1 1 calc R . . . .
C7 C 0.14492(18) 0.30599(17) 0.35292(16) 0.0204(4) Uani 1 1 d . . . . .
H7A H 0.077515 0.249191 0.370216 0.025 Uiso 1 1 calc R . . . .
H7B H 0.195918 0.272827 0.291406 0.025 Uiso 1 1 calc R . . . .
C4 C 0.24242(17) 0.54234(16) 0.43792(13) 0.0153(4) Uani 1 1 d . . . . .
C5 C 0.32110(16) 0.42802(16) 0.44921(14) 0.0160(4) Uani 1 1 d . . . . .
H5 H 0.380549 0.432054 0.513819 0.019 Uiso 1 1 calc R . . . .
C1 C 0.15242(17) 0.64707(16) 0.27739(14) 0.0186(4) Uani 1 1 d . . . . .
H1A H 0.075914 0.678065 0.313827 0.022 Uiso 1 1 calc R . . . .
H1B H 0.140605 0.648125 0.195283 0.022 Uiso 1 1 calc R . . . .
C6 C 0.23047(17) 0.32011(16) 0.45884(16) 0.0188(4) Uani 1 1 d . . . . .
H6A H 0.280858 0.248106 0.468941 0.023 Uiso 1 1 calc R . . . .
H6B H 0.176757 0.329690 0.525764 0.023 Uiso 1 1 calc R . . . .
C9 C 0.18329(17) 0.52236(16) 0.31952(14) 0.0158(4) Uani 1 1 d . . . . .
C8 C 0.08297(16) 0.42342(17) 0.31118(15) 0.0186(4) Uani 1 1 d . . . . .
H8 H 0.064993 0.412606 0.229743 0.022 Uiso 1 1 calc R . . . .
C13 C 0.61201(18) 0.46937(17) 0.41227(17) 0.0227(4) Uani 1 1 d . . . . .
H13A H 0.680844 0.525839 0.418415 0.034 Uiso 1 1 calc GR . . . .
H13B H 0.641876 0.398896 0.373938 0.034 Uiso 1 1 calc GR . . . .
H13C H 0.582290 0.448548 0.487205 0.034 Uiso 1 1 calc GR . . . .
C3 C 0.32767(17) 0.65677(15) 0.42036(15) 0.0173(4) Uani 1 1 d . . . . .
C12 C 0.55128(18) 0.56223(18) 0.22638(16) 0.0241(4) Uani 1 1 d . . . . .
H12A H 0.482638 0.597706 0.183699 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.582632 0.493308 0.186447 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.619334 0.619155 0.235103 0.036 Uiso 1 1 calc GR . . . .
C10 C 0.32456(19) 0.74039(18) 0.52176(16) 0.0230(4) Uani 1 1 d . . . . .
H10A H 0.351386 0.698214 0.588963 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.238976 0.769691 0.532386 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.381334 0.806333 0.508262 0.035 Uiso 1 1 calc GR . . . .
C2 C 0.27147(18) 0.71892(16) 0.31240(15) 0.0203(4) Uani 1 1 d . . . . .
H2A H 0.248243 0.800855 0.329558 0.024 Uiso 1 1 calc R . . . .
H2B H 0.333987 0.719159 0.251165 0.024 Uiso 1 1 calc R . . . .
C14 C -0.04581(17) 0.44921(19) 0.36865(17) 0.0243(4) Uani 1 1 d . . . . .
H14A H -0.104873 0.385977 0.351577 0.036 Uiso 1 1 calc GR . . . .
H14B H -0.079347 0.523469 0.340657 0.036 Uiso 1 1 calc GR . . . .
H14C H -0.033953 0.454348 0.449747 0.036 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
O3 C15 1.4558(19) . ?
O3 C9 1.463(2) . ?
O1 H1 0.8200 . ?
O1 C4 1.407(2) . ?
O2 C11 1.443(2) . ?
O2 C3 1.450(2) . ?
C11 C15 1.530(2) . ?
C11 C13 1.528(3) . ?
C11 C12 1.531(3) . ?
C15 H15 0.9800 . ?
C15 C5 1.523(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.537(2) . ?
C7 C8 1.545(3) . ?
C4 C5 1.527(2) . ?
C4 C9 1.535(2) . ?
C4 C3 1.574(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.539(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C9 1.516(2) . ?
C1 C2 1.537(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 C8 1.528(2) . ?
C8 H8 0.9800 . ?
C8 C14 1.531(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C3 C10 1.513(2) . ?
C3 C2 1.559(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C15 O3 C9 109.48(11) . . ?
C4 O1 H1 109.5 . . ?
C11 O2 C3 120.39(13) . . ?
O2 C11 C15 109.63(13) . . ?
O2 C11 C13 105.39(14) . . ?
O2 C11 C12 110.68(15) . . ?
C15 C11 C12 111.76(14) . . ?
C13 C11 C15 109.88(15) . . ?
C13 C11 C12 109.32(15) . . ?
O3 C15 C11 109.90(14) . . ?
O3 C15 H15 110.7 . . ?
O3 C15 C5 104.49(13) . . ?
C11 C15 H15 110.7 . . ?
C5 C15 C11 110.10(14) . . ?
C5 C15 H15 110.7 . . ?
H7A C7 H7B 107.6 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.29(15) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
O1 C4 C5 115.84(14) . . ?
O1 C4 C9 110.61(14) . . ?
O1 C4 C3 112.76(14) . . ?
C5 C4 C9 99.94(13) . . ?
C5 C4 C3 112.93(14) . . ?
C9 C4 C3 103.18(13) . . ?
C15 C5 C4 97.64(13) . . ?
C15 C5 H5 111.7 . . ?
C15 C5 C6 113.96(14) . . ?
C4 C5 H5 111.7 . . ?
C4 C5 C6 109.50(14) . . ?
C6 C5 H5 111.7 . . ?
H1A C1 H1B 109.1 . . ?
C9 C1 H1A 111.2 . . ?
C9 C1 H1B 111.2 . . ?
C9 C1 C2 102.91(14) . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
C7 C6 C5 112.26(15) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O3 C9 C4 100.64(12) . . ?
O3 C9 C1 107.29(14) . . ?
O3 C9 C8 106.57(13) . . ?
C1 C9 C4 104.22(14) . . ?
C1 C9 C8 120.10(15) . . ?
C8 C9 C4 116.06(15) . . ?
C7 C8 H8 106.5 . . ?
C9 C8 C7 108.05(14) . . ?
C9 C8 H8 106.5 . . ?
C9 C8 C14 115.92(15) . . ?
C14 C8 C7 112.89(16) . . ?
C14 C8 H8 106.5 . . ?
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 . . ?
O2 C3 C4 112.25(14) . . ?
O2 C3 C10 103.30(14) . . ?
O2 C3 C2 113.09(15) . . ?
C10 C3 C4 112.90(14) . . ?
C10 C3 C2 110.66(14) . . ?
C2 C3 C4 104.88(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C2 C3 106.71(15) . . ?
C1 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
C3 C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O3 C15 C5 C4 -38.88(15) . . . . ?
O3 C15 C5 C6 76.47(17) . . . . ?
O3 C9 C8 C7 54.22(17) . . . . ?
O3 C9 C8 C14 -177.96(15) . . . . ?
O1 C4 C5 C15 169.99(14) . . . . ?
O1 C4 C5 C6 51.17(19) . . . . ?
O1 C4 C9 O3 -167.58(13) . . . . ?
O1 C4 C9 C1 81.35(17) . . . . ?
O1 C4 C9 C8 -53.1(2) . . . . ?
O1 C4 C3 O2 138.47(14) . . . . ?
O1 C4 C3 C10 22.2(2) . . . . ?
O1 C4 C3 C2 -98.37(16) . . . . ?
O2 C11 C15 O3 73.61(16) . . . . ?
O2 C11 C15 C5 -40.95(18) . . . . ?
O2 C3 C2 C1 127.08(15) . . . . ?
C11 O2 C3 C4 40.1(2) . . . . ?
C11 O2 C3 C10 162.05(14) . . . . ?
C11 O2 C3 C2 -78.28(19) . . . . ?
C11 C15 C5 C4 79.08(16) . . . . ?
C11 C15 C5 C6 -165.57(14) . . . . ?
C15 O3 C9 C4 20.81(16) . . . . ?
C15 O3 C9 C1 129.49(14) . . . . ?
C15 O3 C9 C8 -100.67(14) . . . . ?
C15 C5 C6 C7 -47.1(2) . . . . ?
C4 C5 C6 C7 61.01(19) . . . . ?
C4 C9 C8 C7 -56.88(19) . . . . ?
C4 C9 C8 C14 70.9(2) . . . . ?
C4 C3 C2 C1 4.46(18) . . . . ?
C5 C4 C9 O3 -44.98(15) . . . . ?
C5 C4 C9 C1 -156.06(14) . . . . ?
C5 C4 C9 C8 69.53(17) . . . . ?
C5 C4 C3 O2 4.8(2) . . . . ?
C5 C4 C3 C10 -111.49(17) . . . . ?
C5 C4 C3 C2 127.94(14) . . . . ?
C1 C9 C8 C7 176.28(15) . . . . ?
C1 C9 C8 C14 -55.9(2) . . . . ?
C6 C7 C8 C9 41.2(2) . . . . ?
C6 C7 C8 C14 -88.35(18) . . . . ?
C9 O3 C15 C11 -106.53(14) . . . . ?
C9 O3 C15 C5 11.58(16) . . . . ?
C9 C4 C5 C15 51.18(15) . . . . ?
C9 C4 C5 C6 -67.65(16) . . . . ?
C9 C4 C3 O2 -102.17(16) . . . . ?
C9 C4 C3 C10 141.56(15) . . . . ?
C9 C4 C3 C2 20.99(17) . . . . ?
C9 C1 C2 C3 -28.55(17) . . . . ?
C8 C7 C6 C5 -45.6(2) . . . . ?
C13 C11 C15 O3 -171.01(14) . . . . ?
C13 C11 C15 C5 74.42(18) . . . . ?
C3 O2 C11 C15 -21.9(2) . . . . ?
C3 O2 C11 C13 -140.06(15) . . . . ?
C3 O2 C11 C12 101.87(17) . . . . ?
C3 C4 C5 C15 -57.82(16) . . . . ?
C3 C4 C5 C6 -176.65(14) . . . . ?
C3 C4 C9 O3 71.59(15) . . . . ?
C3 C4 C9 C1 -39.48(17) . . . . ?
C3 C4 C9 C8 -173.89(14) . . . . ?
C12 C11 C15 O3 -49.48(19) . . . . ?
C12 C11 C15 C5 -164.04(15) . . . . ?
C10 C3 C2 C1 -117.58(16) . . . . ?
C2 C1 C9 O3 -63.78(15) . . . . ?
C2 C1 C9 C4 42.38(17) . . . . ?
C2 C1 C9 C8 174.50(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.646
