# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2014ncs0445
_audit_block_doi                 10.5517/cc1414s3
_database_code_depnum_ccdc_archive 'CCDC 1043794'
loop_
_audit_author_name
_audit_author_address
'peter horton'
;NCS
United Kingdom
;
_audit_update_record             
;
2019-03-26 deposited with the CCDC.	2019-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

#Dr. Christopher Bray / Harry Shirley
#Refcode: HSAldehyde

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H26 O3'
_chemical_formula_sum            'C15 H26 O3'
_chemical_formula_weight         254.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7264(7)
_cell_length_b                   13.0927(9)
_cell_length_c                   11.7193(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.924(2)
_cell_angle_gamma                90
_cell_volume                     1403.07(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19755
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_process_details   
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            22411
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3215
_reflns_number_gt                2611
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.5327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.07798(14) 0.57640(9) 0.12443(12) 0.0177(3) Uani 1 1 d . . . . .
H1A H 0.0741 0.5760 0.0381 0.021 Uiso 1 1 calc R U . . .
C2 C -0.07396(14) 0.60487(10) 0.12517(12) 0.0201(3) Uani 1 1 d . . . . .
H2A H -0.1436 0.5510 0.0818 0.024 Uiso 1 1 calc R U . . .
H2B H -0.0716 0.6056 0.2103 0.024 Uiso 1 1 calc R U . . .
C3 C -0.13154(15) 0.70780(10) 0.06744(12) 0.0202(3) Uani 1 1 d . . . . .
C4 C -0.01102(14) 0.79055(10) 0.11771(12) 0.0185(3) Uani 1 1 d . . . . .
H4 H -0.0023 0.8028 0.2041 0.022 Uiso 1 1 calc R U . . .
C5 C 0.14555(14) 0.76101(10) 0.11833(12) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.18929(14) 0.65872(9) 0.19249(11) 0.0170(3) Uani 1 1 d . . . . .
H6 H 0.1690 0.6711 0.2694 0.020 Uiso 1 1 calc R U . . .
C7 C 0.35502(14) 0.62819(10) 0.23395(12) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.44874(15) 0.72295(11) 0.28811(13) 0.0256(3) Uani 1 1 d . . . . .
H8A H 0.4394 0.7378 0.3680 0.031 Uiso 1 1 calc R U . . .
H8B H 0.5525 0.7060 0.3025 0.031 Uiso 1 1 calc R U . . .
C9 C 0.41070(16) 0.81927(11) 0.21119(15) 0.0287(3) Uani 1 1 d . . . . .
H9A H 0.4281 0.8080 0.1337 0.034 Uiso 1 1 calc R U . . .
H9B H 0.4741 0.8762 0.2545 0.034 Uiso 1 1 calc R U . . .
C10 C 0.25070(16) 0.84714(10) 0.18551(14) 0.0244(3) Uani 1 1 d . . . . .
H10A H 0.2275 0.9100 0.1357 0.029 Uiso 1 1 calc R U . . .
H10B H 0.2354 0.8617 0.2632 0.029 Uiso 1 1 calc R U . . .
C11 C -0.06420(15) 0.88910(10) 0.05033(13) 0.0224(3) Uani 1 1 d . . . . .
H11 H -0.0816 0.8899 -0.0345 0.027 Uiso 1 1 calc R U . . .
C12 C -0.26824(15) 0.73754(12) 0.09685(14) 0.0270(3) Uani 1 1 d . . . . .
H12A H -0.3420 0.6836 0.0688 0.040 Uiso 1 1 calc R U . . .
H12B H -0.3078 0.8018 0.0558 0.040 Uiso 1 1 calc R U . . .
H12C H -0.2423 0.7462 0.1847 0.040 Uiso 1 1 calc R U . . .
C13 C 0.14957(16) 0.75527(11) -0.01211(12) 0.0233(3) Uani 1 1 d . . . . .
H13A H 0.2493 0.7396 -0.0091 0.035 Uiso 1 1 calc R U . . .
H13B H 0.1190 0.8210 -0.0528 0.035 Uiso 1 1 calc R U . . .
H13C H 0.0830 0.7015 -0.0572 0.035 Uiso 1 1 calc R U . . .
C14 C 0.39183(16) 0.55076(11) 0.33978(13) 0.0249(3) Uani 1 1 d . . . . .
H14A H 0.3486 0.5738 0.3996 0.037 Uiso 1 1 calc R U . . .
H14B H 0.4982 0.5458 0.3784 0.037 Uiso 1 1 calc R U . . .
H14C H 0.3520 0.4836 0.3084 0.037 Uiso 1 1 calc R U . . .
C15 C 0.40214(16) 0.58026(11) 0.13317(13) 0.0253(3) Uani 1 1 d . . . . .
H15A H 0.5046 0.5588 0.1671 0.038 Uiso 1 1 calc R U . . .
H15B H 0.3913 0.6307 0.0689 0.038 Uiso 1 1 calc R U . . .
H15C H 0.3405 0.5208 0.0993 0.038 Uiso 1 1 calc R U . . .
O1 O 0.11142(11) 0.47442(7) 0.17096(8) 0.0215(2) Uani 1 1 d . . . . .
H1 H 0.1002 0.4703 0.2388 0.032 Uiso 1 1 calc R U . . .
O2 O -0.17327(11) 0.70428(8) -0.06266(9) 0.0251(2) Uani 1 1 d . . . . .
H2 H -0.1552 0.6460 -0.0841 0.038 Uiso 1 1 calc R U . . .
O3 O -0.08621(12) 0.96718(7) 0.09666(9) 0.0271(2) Uani 1 1 d . . . . .


_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
C1 O1 1.4369(15) . ?
C1 C2 1.5270(18) . ?
C1 C6 1.5433(17) . ?
C1 H1A 1.0000 . ?
C2 C3 1.5261(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.4387(16) . ?
C3 C12 1.5332(19) . ?
C3 C4 1.5570(19) . ?
C4 C11 1.5091(18) . ?
C4 C5 1.5688(18) . ?
C4 H4 1.0000 . ?
C5 C13 1.5443(18) . ?
C5 C10 1.5456(18) . ?
C5 C6 1.5741(17) . ?
C6 C7 1.5686(18) . ?
C6 H6 1.0000 . ?
C7 C15 1.539(2) . ?
C7 C8 1.5422(19) . ?
C7 C14 1.5464(19) . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.2104(17) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1 H1 0.8400 . ?
O2 H2 0.8400 . ?

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
O1 C1 C2 108.61(10) . . ?
O1 C1 C6 115.12(10) . . ?
C2 C1 C6 109.66(10) . . ?
O1 C1 H1A 107.7 . . ?
C2 C1 H1A 107.7 . . ?
C6 C1 H1A 107.7 . . ?
C3 C2 C1 115.01(11) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O2 C3 C2 111.71(10) . . ?
O2 C3 C12 107.06(11) . . ?
C2 C3 C12 109.87(11) . . ?
O2 C3 C4 109.11(11) . . ?
C2 C3 C4 109.36(11) . . ?
C12 C3 C4 109.69(11) . . ?
C11 C4 C3 108.50(11) . . ?
C11 C4 C5 111.86(11) . . ?
C3 C4 C5 115.76(11) . . ?
C11 C4 H4 106.7 . . ?
C3 C4 H4 106.7 . . ?
C5 C4 H4 106.7 . . ?
C13 C5 C10 107.70(11) . . ?
C13 C5 C4 111.06(11) . . ?
C10 C5 C4 107.17(11) . . ?
C13 C5 C6 114.33(10) . . ?
C10 C5 C6 109.39(10) . . ?
C4 C5 C6 106.96(10) . . ?
C1 C6 C7 116.62(11) . . ?
C1 C6 C5 107.39(10) . . ?
C7 C6 C5 116.34(10) . . ?
C1 C6 H6 105.1 . . ?
C7 C6 H6 105.1 . . ?
C5 C6 H6 105.1 . . ?
C15 C7 C8 110.80(12) . . ?
C15 C7 C14 107.47(11) . . ?
C8 C7 C14 104.74(11) . . ?
C15 C7 C6 114.18(11) . . ?
C8 C7 C6 108.87(11) . . ?
C14 C7 C6 110.37(11) . . ?
C9 C8 C7 115.65(12) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 C10 109.95(12) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C9 C10 C5 112.30(11) . . ?
C9 C10 H10A 109.1 . . ?
C5 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C5 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 C4 124.68(12) . . ?
O3 C11 H11 117.7 . . ?
C4 C11 H11 117.7 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C3 O2 H2 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 C1 C2 C3 -174.69(10) . . . . ?
C6 C1 C2 C3 58.73(14) . . . . ?
C1 C2 C3 O2 73.00(14) . . . . ?
C1 C2 C3 C12 -168.34(11) . . . . ?
C1 C2 C3 C4 -47.89(15) . . . . ?
O2 C3 C4 C11 51.84(14) . . . . ?
C2 C3 C4 C11 174.30(10) . . . . ?
C12 C3 C4 C11 -65.14(14) . . . . ?
O2 C3 C4 C5 -74.85(13) . . . . ?
C2 C3 C4 C5 47.61(15) . . . . ?
C12 C3 C4 C5 168.17(11) . . . . ?
C11 C4 C5 C13 -55.51(14) . . . . ?
C3 C4 C5 C13 69.46(14) . . . . ?
C11 C4 C5 C10 61.88(14) . . . . ?
C3 C4 C5 C10 -173.14(11) . . . . ?
C11 C4 C5 C6 179.11(10) . . . . ?
C3 C4 C5 C6 -55.91(14) . . . . ?
O1 C1 C6 C7 39.96(16) . . . . ?
C2 C1 C6 C7 162.77(11) . . . . ?
O1 C1 C6 C5 172.57(10) . . . . ?
C2 C1 C6 C5 -64.62(13) . . . . ?
C13 C5 C6 C1 -61.22(14) . . . . ?
C10 C5 C6 C1 177.92(10) . . . . ?
C4 C5 C6 C1 62.16(12) . . . . ?
C13 C5 C6 C7 71.54(14) . . . . ?
C10 C5 C6 C7 -49.32(15) . . . . ?
C4 C5 C6 C7 -165.08(11) . . . . ?
C1 C6 C7 C15 49.93(16) . . . . ?
C5 C6 C7 C15 -78.47(14) . . . . ?
C1 C6 C7 C8 174.31(11) . . . . ?
C5 C6 C7 C8 45.92(15) . . . . ?
C1 C6 C7 C14 -71.25(14) . . . . ?
C5 C6 C7 C14 160.36(11) . . . . ?
C15 C7 C8 C9 76.65(15) . . . . ?
C14 C7 C8 C9 -167.76(12) . . . . ?
C6 C7 C8 C9 -49.71(16) . . . . ?
C7 C8 C9 C10 57.39(17) . . . . ?
C8 C9 C10 C5 -59.03(16) . . . . ?
C13 C5 C10 C9 -70.10(15) . . . . ?
C4 C5 C10 C9 170.33(11) . . . . ?
C6 C5 C10 C9 54.71(15) . . . . ?
C3 C4 C11 O3 116.78(15) . . . . ?
C5 C4 C11 O3 -114.31(15) . . . . ?

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
C1 H1A O1 1.00 2.58 3.3873(16) 137.2 3_565
O1 H1 O3 0.84 1.98 2.8180(14) 175.8 2_545
O2 H2 O1 0.84 2.00 2.8227(13) 166.0 3_565

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2014ncs0340
_audit_block_doi                 10.5517/cc1414r2
_database_code_depnum_ccdc_archive 'CCDC 1043793'
loop_
_audit_author_name
_audit_author_address
'peter horton'
;NCS
United Kingdom
;
_audit_update_record             
;
2019-03-26 deposited with the CCDC.	2019-05-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT905_2014ncs0340         
;
PROBLEM: Negative K value in the Analysis of Variance ...     -0.321 Report
RESPONSE: unknown
;
# Added during the CSD deposition process: Tuesday 26 March 2019 04:53 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2013

#Dr. Christopher Bray / Harry Shirley
#Refcode:- HSEPOXIDE

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H26 O3'
_chemical_formula_sum            'C15 H26 O3'
_chemical_formula_weight         254.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6454(9)
_cell_length_b                   6.3501(4)
_cell_length_c                   18.3909(13)
_cell_angle_alpha                90
_cell_angle_beta                 106.614(3)
_cell_angle_gamma                90
_cell_volume                     1415.13(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10186
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_process_details   
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            12739
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.394
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3236
_reflns_number_gt                1944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1003P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3236
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1809
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37746(19) 0.1453(4) 0.51617(13) 0.0271(5) Uani 1 1 d . . . . .
H1 H 0.3791 0.0173 0.4848 0.032 Uiso 1 1 calc R U . . .
C2 C 0.39275(19) 0.1101(4) 0.59746(13) 0.0280(5) Uani 1 1 d . . . . .
H2 H 0.4040 -0.0399 0.6145 0.034 Uiso 1 1 calc R U . . .
C3 C 0.34130(19) 0.2512(4) 0.64471(13) 0.0265(5) Uani 1 1 d . . . . .
C4 C 0.28254(19) 0.4458(4) 0.59859(12) 0.0261(5) Uani 1 1 d . . . . .
H4 H 0.3428 0.5450 0.5961 0.031 Uiso 1 1 calc R U . . .
C5 C 0.21871(18) 0.3927(4) 0.51400(13) 0.0250(5) Uani 1 1 d . . . . .
C6 C 0.30935(18) 0.3293(4) 0.47552(12) 0.0249(5) Uani 1 1 d . . . . .
H6 H 0.3618 0.4509 0.4856 0.030 Uiso 1 1 calc R U . . .
C7 C 0.27378(19) 0.3038(4) 0.38745(13) 0.0265(5) Uani 1 1 d . . . . .
C8 C 0.2124(2) 0.5054(4) 0.35271(13) 0.0305(6) Uani 1 1 d . . . . .
H8A H 0.2659 0.6230 0.3606 0.037 Uiso 1 1 calc R U . . .
H8B H 0.1811 0.4850 0.2973 0.037 Uiso 1 1 calc R U . . .
C9 C 0.1201(2) 0.5655(4) 0.38641(14) 0.0333(6) Uani 1 1 d . . . . .
H9A H 0.0626 0.4548 0.3742 0.040 Uiso 1 1 calc R U . . .
H9B H 0.0860 0.6987 0.3631 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1617(2) 0.5930(4) 0.47258(14) 0.0300(6) Uani 1 1 d . . . . .
H10A H 0.0986 0.6298 0.4919 0.036 Uiso 1 1 calc R U . . .
H10B H 0.2147 0.7116 0.4844 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4316(2) 0.3122(4) 0.71650(14) 0.0342(6) Uani 1 1 d . . . . .
H11A H 0.3986 0.3877 0.7511 0.051 Uiso 1 1 calc R U . . .
H11B H 0.4857 0.4033 0.7030 0.051 Uiso 1 1 calc R U . . .
H11C H 0.4685 0.1848 0.7415 0.051 Uiso 1 1 calc R U . . .
C12 C 0.2125(2) 0.5644(4) 0.64154(14) 0.0313(6) Uani 1 1 d . . . . .
H12A H 0.1582 0.6546 0.6054 0.038 Uiso 1 1 calc R U . . .
H12B H 0.1712 0.4612 0.6632 0.038 Uiso 1 1 calc R U . . .
C13 C 0.13128(19) 0.2200(4) 0.51069(14) 0.0291(5) Uani 1 1 d . . . . .
H13A H 0.0938 0.2476 0.5496 0.044 Uiso 1 1 calc R U . . .
H13B H 0.1675 0.0821 0.5199 0.044 Uiso 1 1 calc R U . . .
H13C H 0.0771 0.2207 0.4605 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2027(2) 0.1080(4) 0.35804(13) 0.0313(6) Uani 1 1 d . . . . .
H14A H 0.1302 0.1251 0.3666 0.047 Uiso 1 1 calc R U . . .
H14B H 0.2391 -0.0171 0.3852 0.047 Uiso 1 1 calc R U . . .
H14C H 0.1935 0.0913 0.3036 0.047 Uiso 1 1 calc R U . . .
C15 C 0.3788(2) 0.2859(4) 0.36179(14) 0.0325(6) Uani 1 1 d . . . . .
H15A H 0.3592 0.2935 0.3063 0.049 Uiso 1 1 calc R U . . .
H15B H 0.4151 0.1511 0.3789 0.049 Uiso 1 1 calc R U . . .
H15C H 0.4290 0.4016 0.3838 0.049 Uiso 1 1 calc R U . . .
O1 O 0.48085(13) 0.2014(3) 0.57244(9) 0.0317(4) Uani 1 1 d . . . . .
O2 O 0.26282(14) 0.1138(3) 0.66480(9) 0.0308(4) Uani 1 1 d . . . . .
H2A H 0.2534 0.1536 0.7061 0.046 Uiso 1 1 calc R U . . .
O3 O 0.27971(15) 0.6935(3) 0.70184(9) 0.0336(4) Uani 1 1 d . . . . .
H3 H 0.2786 0.8186 0.6868 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.461(3) . ?
C1 C2 1.469(3) . ?
C1 C6 1.516(3) . ?
C1 H1 1.0000 . ?
C2 O1 1.443(3) . ?
C2 C3 1.518(3) . ?
C2 H2 1.0000 . ?
C3 O2 1.447(3) . ?
C3 C11 1.528(3) . ?
C3 C4 1.561(3) . ?
C4 C12 1.541(3) . ?
C4 C5 1.571(3) . ?
C4 H4 1.0000 . ?
C5 C13 1.546(3) . ?
C5 C10 1.550(3) . ?
C5 C6 1.562(3) . ?
C6 C7 1.561(3) . ?
C6 H6 1.0000 . ?
C7 C15 1.535(3) . ?
C7 C8 1.538(3) . ?
C7 C14 1.539(3) . ?
C8 C9 1.518(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.444(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 H2A 0.8400 . ?
O3 H3 0.8400 . ?

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
O1 C1 C2 59.02(14) . . ?
O1 C1 C6 115.39(19) . . ?
C2 C1 C6 120.7(2) . . ?
O1 C1 H1 116.4 . . ?
C2 C1 H1 116.4 . . ?
C6 C1 H1 116.4 . . ?
O1 C2 C1 60.21(15) . . ?
O1 C2 C3 116.23(19) . . ?
C1 C2 C3 122.7(2) . . ?
O1 C2 H2 115.4 . . ?
C1 C2 H2 115.4 . . ?
C3 C2 H2 115.4 . . ?
O2 C3 C2 103.16(18) . . ?
O2 C3 C11 109.27(18) . . ?
C2 C3 C11 107.90(19) . . ?
O2 C3 C4 111.19(18) . . ?
C2 C3 C4 111.80(18) . . ?
C11 C3 C4 113.0(2) . . ?
C12 C4 C3 111.24(19) . . ?
C12 C4 C5 113.86(18) . . ?
C3 C4 C5 113.47(18) . . ?
C12 C4 H4 105.8 . . ?
C3 C4 H4 105.8 . . ?
C5 C4 H4 105.8 . . ?
C13 C5 C10 109.63(19) . . ?
C13 C5 C6 114.10(18) . . ?
C10 C5 C6 106.67(18) . . ?
C13 C5 C4 110.51(19) . . ?
C10 C5 C4 110.23(18) . . ?
C6 C5 C4 105.55(17) . . ?
C1 C6 C7 112.72(19) . . ?
C1 C6 C5 111.24(18) . . ?
C7 C6 C5 117.77(18) . . ?
C1 C6 H6 104.5 . . ?
C7 C6 H6 104.5 . . ?
C5 C6 H6 104.5 . . ?
C15 C7 C8 108.2(2) . . ?
C15 C7 C14 107.6(2) . . ?
C8 C7 C14 110.60(19) . . ?
C15 C7 C6 107.99(18) . . ?
C8 C7 C6 107.82(18) . . ?
C14 C7 C6 114.50(19) . . ?
C9 C8 C7 113.3(2) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 112.0(2) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C5 112.9(2) . . ?
C9 C10 H10A 109.0 . . ?
C5 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C5 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 C4 111.91(19) . . ?
O3 C12 H12A 109.2 . . ?
C4 C12 H12A 109.2 . . ?
O3 C12 H12B 109.2 . . ?
C4 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 O1 C1 60.77(14) . . ?
C3 O2 H2A 109.5 . . ?
C12 O3 H3 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
C6 C1 C2 O1 -103.0(2) . . . . ?
O1 C1 C2 C3 103.8(2) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
O1 C2 C3 O2 -176.37(17) . . . . ?
C1 C2 C3 O2 113.6(2) . . . . ?
O1 C2 C3 C11 -60.8(2) . . . . ?
C1 C2 C3 C11 -130.8(2) . . . . ?
O1 C2 C3 C4 64.1(3) . . . . ?
C1 C2 C3 C4 -5.9(3) . . . . ?
O2 C3 C4 C12 54.6(2) . . . . ?
C2 C3 C4 C12 169.30(19) . . . . ?
C11 C3 C4 C12 -68.7(3) . . . . ?
O2 C3 C4 C5 -75.4(2) . . . . ?
C2 C3 C4 C5 39.4(3) . . . . ?
C11 C3 C4 C5 161.34(19) . . . . ?
C12 C4 C5 C13 -70.6(2) . . . . ?
C3 C4 C5 C13 58.0(2) . . . . ?
C12 C4 C5 C10 50.7(3) . . . . ?
C3 C4 C5 C10 179.31(19) . . . . ?
C12 C4 C5 C6 165.54(19) . . . . ?
C3 C4 C5 C6 -65.9(2) . . . . ?
O1 C1 C6 C7 129.4(2) . . . . ?
C2 C1 C6 C7 -163.0(2) . . . . ?
O1 C1 C6 C5 -95.8(2) . . . . ?
C2 C1 C6 C5 -28.2(3) . . . . ?
C13 C5 C6 C1 -63.8(2) . . . . ?
C10 C5 C6 C1 175.04(19) . . . . ?
C4 C5 C6 C1 57.8(2) . . . . ?
C13 C5 C6 C7 68.5(3) . . . . ?
C10 C5 C6 C7 -52.7(3) . . . . ?
C4 C5 C6 C7 -169.93(18) . . . . ?
C1 C6 C7 C15 -59.6(2) . . . . ?
C5 C6 C7 C15 168.79(19) . . . . ?
C1 C6 C7 C8 -176.26(19) . . . . ?
C5 C6 C7 C8 52.1(3) . . . . ?
C1 C6 C7 C14 60.2(3) . . . . ?
C5 C6 C7 C14 -71.4(3) . . . . ?
C15 C7 C8 C9 -168.1(2) . . . . ?
C14 C7 C8 C9 74.3(3) . . . . ?
C6 C7 C8 C9 -51.6(3) . . . . ?
C7 C8 C9 C10 56.8(3) . . . . ?
C8 C9 C10 C5 -57.8(3) . . . . ?
C13 C5 C10 C9 -71.0(3) . . . . ?
C6 C5 C10 C9 53.0(3) . . . . ?
C4 C5 C10 C9 167.15(19) . . . . ?
C3 C4 C12 O3 77.5(2) . . . . ?
C5 C4 C12 O3 -152.77(19) . . . . ?
C3 C2 O1 C1 -114.3(2) . . . . ?
C6 C1 O1 C2 111.9(2) . . . . ?

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
O2 H2A O3 0.84 1.87 2.705(2) 169.4 2_546
O3 H3 O2 0.84 1.92 2.747(2) 170.3 1_565

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

