# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_compound_9
_database_code_depnum_ccdc_archive 'CCDC 1937926'
loop_
_audit_author_name
_audit_author_address
'Christian Jandl'
;Technische Universitaet Muenchen
Germany
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 O'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H22 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         242.35
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_Int_Tables_number      60

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,1/2-z
7 1/2-x,1/2+y,z
8 x,-y,1/2+z

_cell_length_a                   31.0922(6)
_cell_length_b                   11.7199(2)
_cell_length_c                   7.5960(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2767.96(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      4.0310
_cell_measurement_theta_max      70.0877
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.114
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.534
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_absorpt_correction_T_min  0.7092
_exptl_absorpt_correction_T_max  0.7533

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             J. Joliffe
scanspeed                           5 s per frame
dx                                  34 mm
2882 frames measured in 9 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
shutterless mode
;
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'IMS microsource'
_diffrn_radiation_monochromator  'Helios optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker Photon CMOS '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CMOS plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            27664
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.03
_diffrn_reflns_theta_max         70.08
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2622
# number of observed reflections (> n sig(I))
_reflns_number_gt                2269
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX III Control Software (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2017)'
_computing_data_reduction        'SAINT (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL2014 (Sheldrick, 2014), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2014)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0747P)²+0.8403P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         2622
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.068

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.51531(4) 0.08847(10) 0.58856(14) 1.000 0.0425(4) d . . .
C1 C Uani 0.67596(4) 0.27999(9) 0.36827(15) 1.000 0.0162(3) d . . .
C2 C Uani 0.63963(4) 0.34008(10) 0.41507(14) 1.000 0.0165(3) d . . .
C3 C Uani 0.64601(4) 0.44626(10) 0.50190(16) 1.000 0.0203(3) d . . .
C4 C Uani 0.68608(4) 0.48886(10) 0.53582(16) 1.000 0.0209(4) d . . .
C5 C Uani 0.72346(4) 0.42839(10) 0.48593(15) 1.000 0.0178(3) d . . .
C6 C Uani 0.76578(4) 0.46974(11) 0.51680(16) 1.000 0.0221(4) d . . .
C7 C Uani 0.80067(4) 0.40710(11) 0.46626(17) 1.000 0.0249(4) d . . .
C8 C Uani 0.79536(4) 0.30043(11) 0.38280(18) 1.000 0.0241(4) d . . .
C9 C Uani 0.75503(4) 0.25829(10) 0.35134(16) 1.000 0.0198(3) d . . .
C10 C Uani 0.71807(4) 0.32093(10) 0.40183(15) 1.000 0.0159(3) d . . .
C11 C Uani 0.59408(4) 0.29668(10) 0.37055(16) 1.000 0.0179(3) d . . .
C12 C Uani 0.57739(4) 0.21116(10) 0.51756(15) 1.000 0.0178(3) d . . .
C13 C Uani 0.53140(4) 0.17356(13) 0.47118(18) 1.000 0.0300(4) d . . .
C14 C Uani 0.59537(4) 0.23966(12) 0.18758(16) 1.000 0.0253(4) d . . .
C15 C Uani 0.56318(4) 0.39920(11) 0.35206(19) 1.000 0.0276(4) d . . .
C16 C Uani 0.60593(5) 0.10503(11) 0.53084(19) 1.000 0.0305(4) d . . .
C17 C Uani 0.57657(4) 0.26730(11) 0.69972(16) 1.000 0.0247(4) d . . .
H1 H Uiso 0.67270 0.20840 0.31130 1.000 0.0190 c RU . .
H1O H Uiso 0.51290 0.11630 0.69000 0.500 0.0640 c RUP A 1
H2O H Uiso 0.49970 0.04260 0.53260 0.500 0.0640 c RUP B 2
H3 H Uiso 0.62160 0.48910 0.53760 1.000 0.0240 c RU . .
H4 H Uiso 0.68880 0.56030 0.59390 1.000 0.0250 c RU . .
H6 H Uiso 0.76980 0.54140 0.57290 1.000 0.0270 c RU . .
H7 H Uiso 0.82880 0.43560 0.48750 1.000 0.0300 c RU . .
H8 H Uiso 0.81990 0.25770 0.34830 1.000 0.0290 c RU . .
H9 H Uiso 0.75180 0.18640 0.29510 1.000 0.0240 c RU . .
H13A H Uiso 0.51220 0.24080 0.47480 1.000 0.0360 c RU . .
H13B H Uiso 0.53110 0.14310 0.34960 1.000 0.0360 c RU . .
H14A H Uiso 0.60820 0.29240 0.10220 1.000 0.0380 c RU . .
H14B H Uiso 0.56610 0.22040 0.15060 1.000 0.0380 c RU . .
H14C H Uiso 0.61270 0.16990 0.19360 1.000 0.0380 c RU . .
H15A H Uiso 0.57660 0.45790 0.27850 1.000 0.0410 c RU . .
H15B H Uiso 0.55700 0.43080 0.46880 1.000 0.0410 c RU . .
H15C H Uiso 0.53630 0.37390 0.29710 1.000 0.0410 c RU . .
H16A H Uiso 0.60630 0.06540 0.41730 1.000 0.0460 c RU . .
H16B H Uiso 0.59450 0.05390 0.62160 1.000 0.0460 c RU . .
H16C H Uiso 0.63530 0.12790 0.56220 1.000 0.0460 c RU . .
H17A H Uiso 0.60560 0.29350 0.73030 1.000 0.0370 c RU . .
H17B H Uiso 0.56680 0.21170 0.78740 1.000 0.0370 c RU . .
H17C H Uiso 0.55690 0.33260 0.69800 1.000 0.0370 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.4282(18) . . yes
O1 H1O 0.8400 . . no
O1 H2O 0.8400 . . no
C1 C2 1.3778(17) . . no
C1 C10 1.4176(17) . . no
C2 C3 1.4223(17) . . no
C2 C11 1.5424(17) . . no
C3 C4 1.3667(17) . . no
C4 C5 1.4130(17) . . no
C5 C10 1.4221(17) . . no
C5 C6 1.4217(18) . . no
C6 C7 1.3650(18) . . no
C7 C8 1.4114(18) . . no
C8 C9 1.3687(18) . . no
C9 C10 1.4166(17) . . no
C11 C14 1.5427(17) . . no
C11 C15 1.5448(18) . . no
C11 C12 1.5877(17) . . no
C12 C17 1.5324(17) . . no
C12 C13 1.5372(18) . . no
C12 C16 1.5313(18) . . no
C1 H1 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C13 H13A 0.9900 . . no
C13 H13B 0.9900 . . no
C14 H14A 0.9800 . . no
C14 H14B 0.9800 . . no
C14 H14C 0.9800 . . no
C15 H15A 0.9800 . . no
C15 H15B 0.9800 . . no
C15 H15C 0.9800 . . no
C16 H16A 0.9800 . . no
C16 H16B 0.9800 . . no
C16 H16C 0.9800 . . no
C17 H17A 0.9800 . . no
C17 H17B 0.9800 . . no
C17 H17C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1O O1 H2O 131.00 . . . no
C13 O1 H2O 109.00 . . . no
C13 O1 H1O 109.00 . . . no
C2 C1 C10 122.54(10) . . . no
C3 C2 C11 121.22(11) . . . no
C1 C2 C11 121.85(10) . . . no
C1 C2 C3 116.91(11) . . . no
C2 C3 C4 122.29(11) . . . no
C3 C4 C5 121.07(11) . . . no
C4 C5 C6 123.10(11) . . . no
C4 C5 C10 117.89(11) . . . no
C6 C5 C10 119.02(11) . . . no
C5 C6 C7 120.39(12) . . . no
C6 C7 C8 120.65(12) . . . no
C7 C8 C9 120.34(12) . . . no
C8 C9 C10 120.59(11) . . . no
C1 C10 C5 119.30(11) . . . no
C5 C10 C9 119.01(11) . . . no
C1 C10 C9 121.68(11) . . . no
C2 C11 C15 109.54(10) . . . no
C2 C11 C14 108.45(10) . . . no
C14 C11 C15 105.74(10) . . . no
C12 C11 C14 111.64(10) . . . no
C12 C11 C15 110.59(10) . . . no
C2 C11 C12 110.74(9) . . . no
C13 C12 C16 108.74(11) . . . no
C13 C12 C17 108.33(10) . . . no
C16 C12 C17 107.39(10) . . . no
C11 C12 C17 111.68(10) . . . no
C11 C12 C13 108.89(10) . . . no
C11 C12 C16 111.70(10) . . . no
O1 C13 C12 112.52(11) . . . yes
C2 C1 H1 119.00 . . . no
C10 C1 H1 119.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C3 C4 H4 119.00 . . . no
C5 C4 H4 120.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
O1 C13 H13A 109.00 . . . no
O1 C13 H13B 109.00 . . . no
C12 C13 H13A 109.00 . . . no
C12 C13 H13B 109.00 . . . no
H13A C13 H13B 108.00 . . . no
C11 C14 H14A 109.00 . . . no
C11 C14 H14B 110.00 . . . no
C11 C14 H14C 109.00 . . . no
H14A C14 H14B 109.00 . . . no
H14A C14 H14C 109.00 . . . no
H14B C14 H14C 109.00 . . . no
C11 C15 H15A 109.00 . . . no
C11 C15 H15B 109.00 . . . no
C11 C15 H15C 109.00 . . . no
H15A C15 H15B 110.00 . . . no
H15A C15 H15C 109.00 . . . no
H15B C15 H15C 109.00 . . . no
C12 C16 H16A 110.00 . . . no
C12 C16 H16B 109.00 . . . no
C12 C16 H16C 109.00 . . . no
H16A C16 H16B 109.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 109.00 . . . no
C12 C17 H17A 109.00 . . . no
C12 C17 H17B 109.00 . . . no
C12 C17 H17C 109.00 . . . no
H17A C17 H17B 109.00 . . . no
H17A C17 H17C 109.00 . . . no
H17B C17 H17C 110.00 . . . no

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
C10 C1 C2 C3 -0.72(17) . . . . no
C10 C1 C2 C11 177.36(10) . . . . no
C2 C1 C10 C5 -0.42(17) . . . . no
C2 C1 C10 C9 -179.46(11) . . . . no
C1 C2 C3 C4 1.04(17) . . . . no
C11 C2 C3 C4 -177.06(11) . . . . no
C1 C2 C11 C12 85.66(13) . . . . no
C1 C2 C11 C14 -37.15(15) . . . . no
C1 C2 C11 C15 -152.10(11) . . . . no
C3 C2 C11 C12 -96.33(12) . . . . no
C3 C2 C11 C14 140.85(11) . . . . no
C3 C2 C11 C15 25.90(15) . . . . no
C2 C3 C4 C5 -0.18(18) . . . . no
C3 C4 C5 C6 179.36(12) . . . . no
C3 C4 C5 C10 -0.99(17) . . . . no
C4 C5 C6 C7 179.69(12) . . . . no
C10 C5 C6 C7 0.03(17) . . . . no
C4 C5 C10 C1 1.27(16) . . . . no
C4 C5 C10 C9 -179.66(11) . . . . no
C6 C5 C10 C1 -179.06(11) . . . . no
C6 C5 C10 C9 0.00(17) . . . . no
C5 C6 C7 C8 -0.04(19) . . . . no
C6 C7 C8 C9 0.0(2) . . . . no
C7 C8 C9 C10 0.03(19) . . . . no
C8 C9 C10 C1 179.00(12) . . . . no
C8 C9 C10 C5 -0.03(17) . . . . no
C2 C11 C12 C13 178.01(10) . . . . no
C2 C11 C12 C16 -61.88(13) . . . . no
C2 C11 C12 C17 58.42(13) . . . . no
C14 C11 C12 C13 -61.04(13) . . . . no
C14 C11 C12 C16 59.07(13) . . . . no
C14 C11 C12 C17 179.37(10) . . . . no
C15 C11 C12 C13 56.39(13) . . . . no
C15 C11 C12 C16 176.50(10) . . . . no
C15 C11 C12 C17 -63.21(13) . . . . no
C11 C12 C13 O1 174.77(10) . . . . no
C16 C12 C13 O1 52.84(14) . . . . no
C17 C12 C13 O1 -63.58(14) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1O O1 0.8400 1.9200 2.6309(15) 141.00 4_656 yes
O1 H2O O1 0.8400 1.8500 2.6489(16) 158.00 5_656 yes
C16 H16B O1 0.9800 2.5100 2.858(2) 101.00 . yes



