# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_hem_0524
_database_code_depnum_ccdc_archive 'CCDC 1847732'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-12-14 downloaded from the CCDC.
;
_audit_creation_date             2018-05-25
_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         'C13 H22 O2'
_chemical_formula_sum            'C13 H22 O2'
_chemical_formula_weight         210.31
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   11.8513(6)
_cell_length_b                   8.0917(4)
_cell_length_c                   24.6768(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2366.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1114
_cell_measurement_temperature    295.38(10)
_cell_measurement_theta_max      26.3710
_cell_measurement_theta_min      4.2580
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83300
_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    1.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5202
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.72
_diffrn_ambient_temperature      295.38(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   55.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000   90.0000 117
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0364481000
_diffrn_orient_matrix_UB_12      0.0585023000
_diffrn_orient_matrix_UB_13      0.0123399000
_diffrn_orient_matrix_UB_21      0.0298402000
_diffrn_orient_matrix_UB_22      0.0651178000
_diffrn_orient_matrix_UB_23      -0.0127988000
_diffrn_orient_matrix_UB_31      -0.0369157000
_diffrn_orient_matrix_UB_32      -0.0050277000
_diffrn_orient_matrix_UB_33      -0.0225774000
_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                1648
_reflns_number_total             2321
_reflns_odcompleteness_completeness 99.46
_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         0.618
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_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         2321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.066
_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)+(0.0603P)²+1.6193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1749
_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 Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), 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 0.17540(14) 0.1870(2) 0.25835(8) 0.0434(5) Uani 1 d . . .
H1 H 0.1592 0.2775 0.2456 0.065 Uiso 1 calc . . GR
O2 O -0.14650(15) 0.0112(2) 0.29289(7) 0.0392(5) Uani 1 d . . .
H2 H -0.1962 0.0656 0.2782 0.059 Uiso 1 calc . . GR
C1 C 0.06166(19) 0.1570(3) 0.37610(9) 0.0303(6) Uani 1 d . . .
H1A H 0.1397 0.1185 0.3724 0.036 Uiso 1 calc . . R
C2 C 0.01328(18) 0.2014(3) 0.31957(9) 0.0283(5) Uani 1 d . . .
H2A H 0.0038 0.3197 0.3124 0.034 Uiso 1 calc . . R
C3 C 0.07400(19) 0.1041(3) 0.27554(9) 0.0313(6) Uani 1 d . . .
H3 H 0.0236 0.0903 0.2444 0.038 Uiso 1 calc . . R
C7 C -0.09633(19) 0.1067(3) 0.33540(9) 0.0312(6) Uani 1 d . . .
C11 C 0.0543(2) 0.2864(3) 0.42150(10) 0.0395(6) Uani 1 d . . .
C6 C -0.0204(2) 0.0068(3) 0.37420(10) 0.0336(6) Uani 1 d . . .
H6 H -0.0549 -0.0240 0.4089 0.040 Uiso 1 calc . . R
C5 C 0.0369(2) -0.1339(3) 0.34325(10) 0.0386(6) Uani 1 d . . .
H5A H -0.0201 -0.2076 0.3287 0.046 Uiso 1 calc . . R
H5B H 0.0840 -0.1968 0.3679 0.046 Uiso 1 calc . . R
C4 C 0.1101(2) -0.0663(3) 0.29641(10) 0.0377(6) Uani 1 d . . .
H4A H 0.1878 -0.0597 0.3086 0.045 Uiso 1 calc . . R
H4B H 0.1075 -0.1442 0.2665 0.045 Uiso 1 calc . . R
C8 C -0.1878(2) 0.2089(4) 0.36283(11) 0.0428(7) Uani 1 d . . .
H8A H -0.2079 0.2981 0.3384 0.051 Uiso 1 calc . . R
H8B H -0.2539 0.1393 0.3667 0.051 Uiso 1 calc . . R
C10 C -0.0589(3) 0.3826(4) 0.42140(13) 0.0594(9) Uani 1 d . . .
H10A H -0.0628 0.4473 0.4544 0.071 Uiso 1 calc . . R
H10B H -0.0576 0.4597 0.3913 0.071 Uiso 1 calc . . R
C13 C 0.1455(3) 0.4170(4) 0.41128(13) 0.0586(9) Uani 1 d . . .
H13A H 0.2187 0.3676 0.4152 0.088 Uiso 1 calc . . GR
H13B H 0.1374 0.5052 0.4370 0.088 Uiso 1 calc . . GR
H13C H 0.1375 0.4601 0.3752 0.088 Uiso 1 calc . . GR
C9 C -0.1634(3) 0.2840(5) 0.41734(13) 0.0607(9) Uani 1 d . . .
H9A H -0.2265 0.3542 0.4272 0.073 Uiso 1 calc . . R
H9B H -0.1595 0.1956 0.4438 0.073 Uiso 1 calc . . R
C12 C 0.0760(3) 0.2045(4) 0.47532(11) 0.0689(11) Uani 1 d . . .
H12A H 0.0166 0.1272 0.4829 0.103 Uiso 1 calc . . GR
H12B H 0.0784 0.2868 0.5033 0.103 Uiso 1 calc . . GR
H12C H 0.1469 0.1471 0.4740 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 H1 0.8200 . ?
O1 C3 1.440(3) . ?
O2 H2 0.8200 . ?
O2 C7 1.432(3) . ?
C1 H1A 0.9800 . ?
C1 C2 1.550(3) . ?
C1 C11 1.536(3) . ?
C1 C6 1.558(3) . ?
C2 H2A 0.9800 . ?
C2 C3 1.523(3) . ?
C2 C7 1.558(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.533(3) . ?
C7 C6 1.542(3) . ?
C7 C8 1.522(3) . ?
C11 C10 1.551(4) . ?
C11 C13 1.533(4) . ?
C11 C12 1.507(4) . ?
C6 H6 0.9800 . ?
C6 C5 1.530(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.545(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.504(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.476(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C3 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 C6 85.56(17) . . ?
C11 C1 H1A 109.8 . . ?
C11 C1 C2 118.5(2) . . ?
C11 C1 C6 121.2(2) . . ?
C6 C1 H1A 109.8 . . ?
C1 C2 H2A 115.5 . . ?
C1 C2 C7 88.21(17) . . ?
C3 C2 C1 110.33(18) . . ?
C3 C2 H2A 115.5 . . ?
C3 C2 C7 108.56(18) . . ?
C7 C2 H2A 115.5 . . ?
O1 C3 C2 111.33(19) . . ?
O1 C3 H3 109.3 . . ?
O1 C3 C4 106.54(19) . . ?
C2 C3 H3 109.3 . . ?
C2 C3 C4 110.94(19) . . ?
C4 C3 H3 109.3 . . ?
O2 C7 C2 115.35(19) . . ?
O2 C7 C6 114.47(19) . . ?
O2 C7 C8 108.86(19) . . ?
C6 C7 C2 85.82(17) . . ?
C8 C7 C2 115.9(2) . . ?
C8 C7 C6 115.1(2) . . ?
C1 C11 C10 113.0(2) . . ?
C13 C11 C1 108.0(2) . . ?
C13 C11 C10 105.3(2) . . ?
C12 C11 C1 109.4(2) . . ?
C12 C11 C10 111.7(3) . . ?
C12 C11 C13 109.2(2) . . ?
C1 C6 H6 115.6 . . ?
C7 C6 C1 88.52(17) . . ?
C7 C6 H6 115.6 . . ?
C5 C6 C1 108.5(2) . . ?
C5 C6 C7 109.82(19) . . ?
C5 C6 H6 115.6 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C6 C5 C4 111.1(2) . . ?
H5A C5 H5B 108.0 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C3 C4 C5 114.4(2) . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C7 C8 H8A 107.6 . . ?
C7 C8 H8B 107.6 . . ?
H8A C8 H8B 107.1 . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 H8A 107.6 . . ?
C9 C8 H8B 107.6 . . ?
C11 C10 H10A 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.3 . . ?
C9 C10 C11 117.0(3) . . ?
C9 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
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 . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C10 C9 C8 116.1(3) . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
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 . . ?

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 C3 C4 C5 147.5(2) . . . . ?
O2 C7 C6 C1 141.61(19) . . . . ?
O2 C7 C6 C5 32.4(3) . . . . ?
O2 C7 C8 C9 163.9(3) . . . . ?
C1 C2 C3 O1 -85.9(2) . . . . ?
C1 C2 C3 C4 32.5(3) . . . . ?
C1 C2 C7 O2 -140.9(2) . . . . ?
C1 C2 C7 C6 -25.74(17) . . . . ?
C1 C2 C7 C8 90.2(2) . . . . ?
C1 C11 C10 C9 48.1(4) . . . . ?
C1 C6 C5 C4 -35.7(3) . . . . ?
C2 C1 C11 C10 39.6(3) . . . . ?
C2 C1 C11 C13 -76.5(3) . . . . ?
C2 C1 C11 C12 164.7(2) . . . . ?
C2 C1 C6 C7 -25.76(16) . . . . ?
C2 C1 C6 C5 84.68(19) . . . . ?
C2 C3 C4 C5 26.1(3) . . . . ?
C2 C7 C6 C1 25.61(16) . . . . ?
C2 C7 C6 C5 -83.6(2) . . . . ?
C2 C7 C8 C9 -64.0(3) . . . . ?
C3 C2 C7 O2 -30.0(3) . . . . ?
C3 C2 C7 C6 85.12(19) . . . . ?
C3 C2 C7 C8 -159.0(2) . . . . ?
C7 C2 C3 O1 178.96(18) . . . . ?
C7 C2 C3 C4 -62.6(2) . . . . ?
C7 C6 C5 C4 59.6(3) . . . . ?
C7 C8 C9 C10 52.0(4) . . . . ?
C11 C1 C2 C3 153.0(2) . . . . ?
C11 C1 C2 C7 -97.9(2) . . . . ?
C11 C1 C6 C7 95.1(2) . . . . ?
C11 C1 C6 C5 -154.5(2) . . . . ?
C11 C10 C9 C8 -72.9(4) . . . . ?
C6 C1 C2 C3 -83.67(19) . . . . ?
C6 C1 C2 C7 25.48(16) . . . . ?
C6 C1 C11 C10 -63.5(3) . . . . ?
C6 C1 C11 C13 -179.6(2) . . . . ?
C6 C1 C11 C12 61.7(3) . . . . ?
C6 C7 C8 C9 33.9(3) . . . . ?
C6 C5 C4 C3 -24.4(3) . . . . ?
C8 C7 C6 C1 -91.1(2) . . . . ?
C8 C7 C6 C5 159.7(2) . . . . ?
C13 C11 C10 C9 165.8(3) . . . . ?
C12 C11 C10 C9 -75.8(3) . . . . ?


_olex2_date_sample_data_collection 2018-05-24
_olex2_submission_special_instructions 'No special instructions were received'
