# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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#######################################################################

data_lhx
_database_code_depnum_ccdc_archive 'CCDC 1935679'
_audit_update_record             
;
2019-06-21 deposited with the CCDC.	2019-08-16 downloaded from the CCDC.
;
_audit_creation_date             2019-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 O'
_chemical_formula_sum            'C25 H24 O'
_chemical_formula_weight         338.42
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.220(2)
_cell_length_b                   9.550(2)
_cell_length_c                   20.071(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.737(13)
_cell_angle_gamma                90
_cell_volume                     1954.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9398
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      68.75
_cell_measurement_theta_min      4.63
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16572
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.671
_diffrn_reflns_theta_min         6.404
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2969
_reflns_number_total             3594
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.282
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.081
_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)+(0.0488P)²+1.1375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1530
_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
2.a Ternary CH refined with riding coordinates:
 C006(H006), C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00I,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00K), C00K(H00L), C00L(H00M),
 C00N(H00Q), C00O(H00R), C00P(H00S)
2.d X=CH2 refined with riding coordinates:
 C00Q(H00T,H00U)
2.e Idealised Me refined as rotating group:
 C00M(H00N,H00O,H00P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.95435(16) 0.85305(18) 0.88755(8) 0.0663(5) Uani 1 1 d . . . . .
C002 C 0.64056(19) 0.5129(2) 0.62559(10) 0.0411(4) Uani 1 1 d . . . . .
C003 C 0.60677(19) 0.3631(2) 0.60742(9) 0.0423(5) Uani 1 1 d . . . . .
C004 C 0.52654(19) 0.6005(2) 0.64444(10) 0.0443(5) Uani 1 1 d . . . . .
C005 C 0.81313(18) 0.6250(2) 0.72034(10) 0.0438(5) Uani 1 1 d . . . . .
C006 C 0.77659(19) 0.5335(2) 0.66213(10) 0.0445(5) Uani 1 1 d . . . . .
H006 H 0.8261 0.4456 0.6646 0.053 Uiso 1 1 calc R . . . .
C007 C 0.7523(2) 0.5813(2) 0.59100(11) 0.0482(5) Uani 1 1 d . . . . .
H007 H 0.7915 0.5192 0.5589 0.058 Uiso 1 1 calc R . . . .
C008 C 0.8067(2) 0.8353(2) 0.78795(11) 0.0492(5) Uani 1 1 d . . . . .
H008 H 0.7714 0.9235 0.7948 0.059 Uiso 1 1 calc R . . . .
C009 C 0.9033(2) 0.7835(2) 0.83195(11) 0.0498(5) Uani 1 1 d . . . . .
C00A C 0.7617(2) 0.7560(2) 0.73328(11) 0.0493(5) Uani 1 1 d . . . . .
H00A H 0.6951 0.7918 0.7044 0.059 Uiso 1 1 calc R . . . .
C00B C 0.9117(2) 0.5766(2) 0.76561(11) 0.0530(5) Uani 1 1 d . . . . .
H00B H 0.9485 0.4892 0.7586 0.064 Uiso 1 1 calc R . . . .
C00C C 0.4885(2) 0.6017(3) 0.70930(11) 0.0560(6) Uani 1 1 d . . . . .
H00C H 0.5352 0.5494 0.7419 0.067 Uiso 1 1 calc R . . . .
C00D C 0.7005(2) 0.2696(2) 0.58605(11) 0.0528(5) Uani 1 1 d . . . . .
H00D H 0.7853 0.3011 0.5807 0.063 Uiso 1 1 calc R . . . .
C00E C 0.4818(2) 0.3104(2) 0.61409(11) 0.0527(5) Uani 1 1 d . . . . .
H00E H 0.4168 0.3700 0.6279 0.063 Uiso 1 1 calc R . . . .
C00F C 0.9565(2) 0.6533(3) 0.82027(12) 0.0598(6) Uani 1 1 d . . . . .
H00F H 1.0227 0.6176 0.8495 0.072 Uiso 1 1 calc R . . . .
C00G C 0.5451(3) 0.0818(2) 0.58021(13) 0.0671(7) Uani 1 1 d . . . . .
H00G H 0.5247 -0.0116 0.5714 0.081 Uiso 1 1 calc R . . . .
C00H C 0.4513(2) 0.1719(3) 0.60079(13) 0.0646(6) Uani 1 1 d . . . . .
H00H H 0.3667 0.1396 0.6058 0.077 Uiso 1 1 calc R . . . .
C00I C 0.7556(2) 0.7343(2) 0.57082(13) 0.0590(6) Uani 1 1 d . . . . .
H00I H 0.7178 0.7442 0.5255 0.071 Uiso 1 1 calc R . . . .
H00J H 0.7025 0.7884 0.5998 0.071 Uiso 1 1 calc R . . . .
C00J C 0.4532(2) 0.6763(2) 0.59633(13) 0.0576(6) Uani 1 1 d . . . . .
H00K H 0.4757 0.6742 0.5522 0.069 Uiso 1 1 calc R . . . .
C00K C 0.6696(3) 0.1313(2) 0.57271(13) 0.0635(6) Uani 1 1 d . . . . .
H00L H 0.7336 0.0710 0.5585 0.076 Uiso 1 1 calc R . . . .
C00L C 0.3814(3) 0.6801(3) 0.72623(15) 0.0754(8) Uani 1 1 d . . . . .
H00M H 0.3567 0.6802 0.7700 0.091 Uiso 1 1 calc R . . . .
C00M C 0.8963(3) 0.9827(3) 0.90290(14) 0.0754(8) Uani 1 1 d . . . . .
H00N H 0.9048 1.0469 0.8666 0.113 Uiso 1 1 calc GR . . . .
H00O H 0.9395 1.0205 0.9428 0.113 Uiso 1 1 calc GR . . . .
H00P H 0.8050 0.9687 0.9096 0.113 Uiso 1 1 calc GR . . . .
C00N C 0.3468(3) 0.7550(3) 0.61350(17) 0.0771(8) Uani 1 1 d . . . . .
H00Q H 0.2988 0.8064 0.5810 0.093 Uiso 1 1 calc R . . . .
C00O C 0.3119(3) 0.7576(3) 0.6784(2) 0.0859(10) Uani 1 1 d . . . . .
H00R H 0.2412 0.8117 0.6899 0.103 Uiso 1 1 calc R . . . .
C00P C 0.8934(3) 0.7915(3) 0.57500(18) 0.0844(9) Uani 1 1 d . . . . .
H00S H 0.9356 0.7915 0.6175 0.101 Uiso 1 1 calc R . . . .
C00Q C 0.9581(4) 0.8381(4) 0.5306(2) 0.1218(14) Uani 1 1 d . . . . .
H00T H 0.9221 0.8414 0.4868 0.146 Uiso 1 1 calc R . . . .
H00U H 1.0430 0.8702 0.5407 0.146 Uiso 1 1 calc R . . . .


_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
O001 C009 1.372(3) . ?
O001 C00M 1.416(3) . ?
C002 C003 1.512(3) . ?
C002 C004 1.503(3) . ?
C002 C006 1.541(3) . ?
C002 C007 1.522(3) . ?
C003 C00D 1.397(3) . ?
C003 C00E 1.387(3) . ?
C004 C00C 1.383(3) . ?
C004 C00J 1.387(3) . ?
C005 C006 1.487(3) . ?
C005 C00A 1.388(3) . ?
C005 C00B 1.391(3) . ?
C006 H006 0.9800 . ?
C006 C007 1.504(3) . ?
C007 H007 0.9800 . ?
C007 C00I 1.517(3) . ?
C008 H008 0.9300 . ?
C008 C009 1.373(3) . ?
C008 C00A 1.387(3) . ?
C009 C00F 1.384(3) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00B C00F 1.373(3) . ?
C00C H00C 0.9300 . ?
C00C C00L 1.386(3) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.380(3) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.381(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.372(4) . ?
C00G C00K 1.375(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00I C00P 1.508(4) . ?
C00J H00K 0.9300 . ?
C00J C00N 1.384(3) . ?
C00K H00L 0.9300 . ?
C00L H00M 0.9300 . ?
C00L C00O 1.374(4) . ?
C00M H00N 0.9600 . ?
C00M H00O 0.9600 . ?
C00M H00P 0.9600 . ?
C00N H00Q 0.9300 . ?
C00N C00O 1.372(4) . ?
C00O H00R 0.9300 . ?
C00P H00S 0.9300 . ?
C00P C00Q 1.227(4) . ?
C00Q H00T 0.9300 . ?
C00Q H00U 0.9300 . ?

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
C009 O001 C00M 117.23(19) . . ?
C003 C002 C006 114.86(16) . . ?
C003 C002 C007 117.57(17) . . ?
C004 C002 C003 114.78(16) . . ?
C004 C002 C006 119.95(16) . . ?
C004 C002 C007 119.56(17) . . ?
C007 C002 C006 58.80(13) . . ?
C00D C003 C002 121.91(18) . . ?
C00E C003 C002 121.14(18) . . ?
C00E C003 C00D 116.89(19) . . ?
C00C C004 C002 120.81(19) . . ?
C00C C004 C00J 118.6(2) . . ?
C00J C004 C002 120.52(19) . . ?
C00A C005 C006 126.73(18) . . ?
C00A C005 C00B 116.38(19) . . ?
C00B C005 C006 116.86(18) . . ?
C002 C006 H006 111.2 . . ?
C005 C006 C002 128.41(17) . . ?
C005 C006 H006 111.2 . . ?
C005 C006 C007 125.81(18) . . ?
C007 C006 C002 59.95(13) . . ?
C007 C006 H006 111.2 . . ?
C002 C007 H007 113.0 . . ?
C006 C007 C002 61.25(13) . . ?
C006 C007 H007 113.0 . . ?
C006 C007 C00I 122.72(19) . . ?
C00I C007 C002 124.41(18) . . ?
C00I C007 H007 113.0 . . ?
C009 C008 H008 120.0 . . ?
C009 C008 C00A 120.0(2) . . ?
C00A C008 H008 120.0 . . ?
O001 C009 C008 124.6(2) . . ?
O001 C009 C00F 116.11(19) . . ?
C008 C009 C00F 119.2(2) . . ?
C005 C00A H00A 119.0 . . ?
C008 C00A C005 122.0(2) . . ?
C008 C00A H00A 119.0 . . ?
C005 C00B H00B 118.9 . . ?
C00F C00B C005 122.3(2) . . ?
C00F C00B H00B 118.9 . . ?
C004 C00C H00C 119.7 . . ?
C004 C00C C00L 120.7(2) . . ?
C00L C00C H00C 119.7 . . ?
C003 C00D H00D 119.4 . . ?
C00K C00D C003 121.2(2) . . ?
C00K C00D H00D 119.4 . . ?
C003 C00E H00E 119.1 . . ?
C00H C00E C003 121.7(2) . . ?
C00H C00E H00E 119.1 . . ?
C009 C00F H00F 120.0 . . ?
C00B C00F C009 120.1(2) . . ?
C00B C00F H00F 120.0 . . ?
C00H C00G H00G 120.4 . . ?
C00H C00G C00K 119.1(2) . . ?
C00K C00G H00G 120.4 . . ?
C00E C00H H00H 119.8 . . ?
C00G C00H C00E 120.4(2) . . ?
C00G C00H H00H 119.8 . . ?
C007 C00I H00I 109.3 . . ?
C007 C00I H00J 109.3 . . ?
H00I C00I H00J 107.9 . . ?
C00P C00I C007 111.8(2) . . ?
C00P C00I H00I 109.3 . . ?
C00P C00I H00J 109.3 . . ?
C004 C00J H00K 119.7 . . ?
C00N C00J C004 120.5(2) . . ?
C00N C00J H00K 119.7 . . ?
C00D C00K H00L 119.7 . . ?
C00G C00K C00D 120.6(2) . . ?
C00G C00K H00L 119.7 . . ?
C00C C00L H00M 120.0 . . ?
C00O C00L C00C 120.0(3) . . ?
C00O C00L H00M 120.0 . . ?
O001 C00M H00N 109.5 . . ?
O001 C00M H00O 109.5 . . ?
O001 C00M H00P 109.5 . . ?
H00N C00M H00O 109.5 . . ?
H00N C00M H00P 109.5 . . ?
H00O C00M H00P 109.5 . . ?
C00J C00N H00Q 119.9 . . ?
C00O C00N C00J 120.2(3) . . ?
C00O C00N H00Q 119.9 . . ?
C00L C00O H00R 120.0 . . ?
C00N C00O C00L 119.9(2) . . ?
C00N C00O H00R 120.0 . . ?
C00I C00P H00S 115.3 . . ?
C00Q C00P C00I 129.5(4) . . ?
C00Q C00P H00S 115.3 . . ?
C00P C00Q H00T 120.0 . . ?
C00P C00Q H00U 120.0 . . ?
H00T C00Q H00U 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
