# Electronic Supplementary Material (ESI) for ChemComm.
# 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_xumh_9312
_database_code_depnum_ccdc_archive 'CCDC 1836259'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-14
_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         'C22 H23 F O'
_chemical_formula_sum            'C22 H23 F O'
_chemical_formula_weight         322.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C42 H54 O6'
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'
F F 0.0727 0.0534 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.6134(3)
_cell_length_b                   8.4407(3)
_cell_length_c                   17.1212(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.760(2)
_cell_angle_gamma                90.00
_cell_volume                     1816.53(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    290.55(16)
_cell_measurement_theta_max      68.6180
_cell_measurement_theta_min      5.1620
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78754
_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    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6384
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_temperature      290.55(16)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -61.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  131.0000 -141.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega  -78.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -32.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   30.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -71.0000  -69.9736 30

#__ type_ start__ end____ width___ exp.time_
  6 omega   27.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega   68.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   56.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega  123.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega   84.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
 15 omega  111.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   43.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 57

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0125345000
_diffrn_orient_matrix_UB_12      -0.0125523000
_diffrn_orient_matrix_UB_13      0.0900550000
_diffrn_orient_matrix_UB_21      0.0144675000
_diffrn_orient_matrix_UB_22      0.1808734000
_diffrn_orient_matrix_UB_23      0.0060322000
_diffrn_orient_matrix_UB_31      -0.1211201000
_diffrn_orient_matrix_UB_32      0.0202831000
_diffrn_orient_matrix_UB_33      0.0023834000
_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                2560
_reflns_number_total             3059
_reflns_odcompleteness_completeness 95.60
_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         0.133
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.038
_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)+(0.0643P)²+0.3522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1390
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4AA(H4AA,H4AB), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
F1 F 0.44376(13) -0.02901(19) 0.41636(8) 0.1099(5) Uani 1 d . . .
O1 O 0.14426(13) 0.13656(18) 0.02998(8) 0.0852(5) Uani 1 d . . .
C1 C 0.17507(12) 0.09544(19) -0.14922(9) 0.0509(4) Uani 1 d . . .
C2 C 0.21397(18) 0.0770(3) -0.22198(11) 0.0800(6) Uani 1 d . . .
H2 H 0.2723 0.0114 -0.2270 0.096 Uiso 1 calc . . R
C3 C 0.1674(2) 0.1546(4) -0.28731(12) 0.1008(8) Uani 1 d . . .
H3 H 0.1944 0.1389 -0.3357 0.121 Uiso 1 calc . . R
C4 C 0.0841(2) 0.2520(4) -0.28228(16) 0.1017(9) Uani 1 d . . .
H4 H 0.0549 0.3059 -0.3263 0.122 Uiso 1 calc . . R
C4AA C 0.34375(13) -0.0223(2) -0.07963(12) 0.0661(5) Uani 1 d . . .
H4AA H 0.3691 -0.1056 -0.0438 0.079 Uiso 1 calc . . R
H4AB H 0.3609 -0.0499 -0.1321 0.079 Uiso 1 calc . . R
C5 C 0.0430(2) 0.2706(3) -0.21199(18) 0.1066(9) Uani 1 d . . .
H5 H -0.0158 0.3356 -0.2082 0.128 Uiso 1 calc . . R
C6 C 0.08859(16) 0.1930(3) -0.14544(13) 0.0816(6) Uani 1 d . . .
H6 H 0.0598 0.2076 -0.0977 0.098 Uiso 1 calc . . R
C7 C 0.22300(11) 0.00378(18) -0.07691(9) 0.0478(4) Uani 1 d . . .
C8 C 0.22030(15) 0.1138(2) -0.00577(10) 0.0622(4) Uani 1 d . . .
C9 C 0.3284(2) 0.1870(3) 0.01151(14) 0.0954(8) Uani 1 d . . .
H9A H 0.3232 0.3016 0.0135 0.114 Uiso 1 calc . . R
H9B H 0.3613 0.1493 0.0613 0.114 Uiso 1 calc . . R
C10 C 0.39189(15) 0.1361(3) -0.05471(15) 0.0888(7) Uani 1 d . . .
H10A H 0.4666 0.1250 -0.0371 0.107 Uiso 1 calc . . R
H10B H 0.3847 0.2118 -0.0975 0.107 Uiso 1 calc . . R
C11 C 0.15694(12) -0.1467(2) -0.06871(9) 0.0545(4) Uani 1 d . . .
H11A H 0.1460 -0.1951 -0.1201 0.065 Uiso 1 calc . . R
H11B H 0.0876 -0.1148 -0.0537 0.065 Uiso 1 calc . . R
C12 C 0.19992(13) -0.2748(2) -0.01098(10) 0.0586(4) Uani 1 d . . .
H12 H 0.2654 -0.3174 -0.0299 0.070 Uiso 1 calc . . R
C13 C 0.22550(13) -0.2155(2) 0.07086(10) 0.0568(4) Uani 1 d . . .
H13 H 0.1726 -0.1601 0.0940 0.068 Uiso 1 calc . . R
C14 C 0.31691(13) -0.2356(2) 0.11261(10) 0.0593(4) Uani 1 d . . .
H14 H 0.3685 -0.2921 0.0886 0.071 Uiso 1 calc . . R
C15 C 0.34730(14) -0.17948(19) 0.19286(10) 0.0576(4) Uani 1 d . . .
C16 C 0.44630(15) -0.2191(2) 0.22868(12) 0.0709(5) Uani 1 d . . .
H16 H 0.4916 -0.2819 0.2017 0.085 Uiso 1 calc . . R
C17 C 0.47958(17) -0.1680(3) 0.30345(13) 0.0797(6) Uani 1 d . . .
H17 H 0.5465 -0.1947 0.3266 0.096 Uiso 1 calc . . R
C18 C 0.41209(19) -0.0781(2) 0.34209(12) 0.0745(5) Uani 1 d . . .
C19 C 0.31466(19) -0.0355(3) 0.31001(13) 0.0806(6) Uani 1 d . . .
H19 H 0.2701 0.0268 0.3379 0.097 Uiso 1 calc . . R
C20 C 0.28254(16) -0.0860(2) 0.23535(12) 0.0730(5) Uani 1 d . . .
H20 H 0.2158 -0.0567 0.2129 0.088 Uiso 1 calc . . R
C21 C 0.11830(18) -0.4092(2) -0.01179(14) 0.0822(6) Uani 1 d . . .
H21A H 0.0536 -0.3704 0.0071 0.123 Uiso 1 calc . . GR
H21B H 0.1461 -0.4937 0.0214 0.123 Uiso 1 calc . . GR
H21C H 0.1041 -0.4478 -0.0644 0.123 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
F1 C18 1.365(2) . ?
O1 C8 1.195(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.372(3) . ?
C1 C7 1.540(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.343(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(4) . ?
C4AA H4AA 0.9700 . ?
C4AA H4AB 0.9700 . ?
C4AA C7 1.544(2) . ?
C4AA C10 1.515(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.534(2) . ?
C7 C11 1.532(2) . ?
C8 C9 1.504(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.504(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.533(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.498(2) . ?
C12 C21 1.532(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.316(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.474(2) . ?
C15 C16 1.386(2) . ?
C15 C20 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.353(3) . ?
C18 C19 1.352(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C2 C1 C7 121.45(16) . . ?
C6 C1 C2 116.89(17) . . ?
C6 C1 C7 121.59(15) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
H4AA C4AA H4AB 109.0 . . ?
C7 C4AA H4AA 111.0 . . ?
C7 C4AA H4AB 111.0 . . ?
C10 C4AA H4AA 111.0 . . ?
C10 C4AA H4AB 111.0 . . ?
C10 C4AA C7 103.83(16) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 121.2(2) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C1 C7 C4AA 111.71(13) . . ?
C8 C7 C1 107.52(13) . . ?
C8 C7 C4AA 101.38(13) . . ?
C11 C7 C1 108.06(12) . . ?
C11 C7 C4AA 115.47(13) . . ?
C11 C7 C8 112.39(13) . . ?
O1 C8 C7 125.14(16) . . ?
O1 C8 C9 125.88(19) . . ?
C9 C8 C7 108.99(17) . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 C8 105.37(17) . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C4AA C10 H10A 111.0 . . ?
C4AA C10 H10B 111.0 . . ?
C9 C10 C4AA 103.79(16) . . ?
C9 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C7 C11 H11A 107.7 . . ?
C7 C11 H11B 107.7 . . ?
C7 C11 C12 118.54(12) . . ?
H11A C11 H11B 107.1 . . ?
C12 C11 H11A 107.7 . . ?
C12 C11 H11B 107.7 . . ?
C11 C12 H12 108.0 . . ?
C13 C12 C11 113.89(14) . . ?
C13 C12 H12 108.0 . . ?
C13 C12 C21 110.39(15) . . ?
C21 C12 C11 108.37(15) . . ?
C21 C12 H12 108.0 . . ?
C12 C13 H13 117.4 . . ?
C14 C13 C12 125.17(16) . . ?
C14 C13 H13 117.4 . . ?
C13 C14 H14 116.1 . . ?
C13 C14 C15 127.81(17) . . ?
C15 C14 H14 116.1 . . ?
C16 C15 C14 119.34(17) . . ?
C20 C15 C14 123.63(16) . . ?
C20 C15 C16 117.02(18) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.84(19) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.20(19) . . ?
C18 C17 H17 120.9 . . ?
C17 C18 F1 118.6(2) . . ?
C19 C18 F1 118.9(2) . . ?
C19 C18 C17 122.5(2) . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.8(2) . . ?
C20 C19 H19 120.6 . . ?
C15 C20 H20 119.2 . . ?
C19 C20 C15 121.56(19) . . ?
C19 C20 H20 119.2 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
F1 C18 C19 C20 -179.56(19) . . . . ?
O1 C8 C9 C10 -173.7(2) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C1 C7 C8 O1 81.1(2) . . . . ?
C1 C7 C8 C9 -99.11(16) . . . . ?
C1 C7 C11 C12 168.50(14) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C7 C4AA 33.6(2) . . . . ?
C2 C1 C7 C8 143.97(17) . . . . ?
C2 C1 C7 C11 -94.48(19) . . . . ?
C2 C3 C4 C5 -2.0(4) . . . . ?
C3 C4 C5 C6 1.7(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4AA C7 C8 O1 -161.56(18) . . . . ?
C4AA C7 C8 C9 18.23(18) . . . . ?
C4AA C7 C11 C12 42.6(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 C7 C4AA -149.72(18) . . . . ?
C6 C1 C7 C8 -39.3(2) . . . . ?
C6 C1 C7 C11 82.2(2) . . . . ?
C7 C1 C2 C3 177.2(2) . . . . ?
C7 C1 C6 C5 -177.4(2) . . . . ?
C7 C4AA C10 C9 41.3(2) . . . . ?
C7 C8 C9 C10 6.5(2) . . . . ?
C7 C11 C12 C13 55.0(2) . . . . ?
C7 C11 C12 C21 178.23(15) . . . . ?
C8 C7 C11 C12 -73.02(18) . . . . ?
C8 C9 C10 C4AA -29.3(2) . . . . ?
C10 C4AA C7 C1 78.23(18) . . . . ?
C10 C4AA C7 C8 -36.01(17) . . . . ?
C10 C4AA C7 C11 -157.77(15) . . . . ?
C11 C7 C8 O1 -37.7(2) . . . . ?
C11 C7 C8 C9 142.10(16) . . . . ?
C11 C12 C13 C14 -127.47(18) . . . . ?
C12 C13 C14 C15 179.47(15) . . . . ?
C13 C14 C15 C16 176.93(18) . . . . ?
C13 C14 C15 C20 -3.9(3) . . . . ?
C14 C15 C16 C17 179.12(17) . . . . ?
C14 C15 C20 C19 -179.56(18) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C15 C20 C19 -0.4(3) . . . . ?
C16 C17 C18 F1 179.09(18) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C21 C12 C13 C14 110.4(2) . . . . ?

_olex2_date_sample_data_collection 2018-03-14
_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_xumh_0314
_database_code_depnum_ccdc_archive 'CCDC 1836270'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-16
_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         'C28 H28 O'
_chemical_formula_sum            'C28 H28 O'
_chemical_formula_weight         380.50
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y+1/2, z+1/2'
4 'x+1/2, -y+1/2, z'

_cell_length_a                   18.3080(5)
_cell_length_b                   19.0516(6)
_cell_length_c                   6.22760(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2172.16(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    292.6(5)
_cell_measurement_theta_max      69.5470
_cell_measurement_theta_min      5.2280
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87909
_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    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_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  0.0157
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6904
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.64
_diffrn_ambient_temperature      292.6(5)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -58.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega   64.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega   42.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  8 omega   77.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   45.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  -90.0000 116

#__ type_ start__ end____ width___ exp.time_
 10 omega  -82.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   51.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   99.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
 16 omega   94.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   94.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  120.0000 30
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0224754000
_diffrn_orient_matrix_UB_12      -0.0779082000
_diffrn_orient_matrix_UB_13      0.0098468000
_diffrn_orient_matrix_UB_21      -0.0810165000
_diffrn_orient_matrix_UB_22      -0.0214048000
_diffrn_orient_matrix_UB_23      0.0146415000
_diffrn_orient_matrix_UB_31      -0.0038894000
_diffrn_orient_matrix_UB_32      -0.0042598000
_diffrn_orient_matrix_UB_33      -0.2465531000
_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                2794
_reflns_number_total             3030
_reflns_odcompleteness_completeness 97.85
_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         0.097
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.076
_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)+(0.0452P)²+0.1088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0817
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
;
_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 -0.66911(6) -0.32468(7) -0.5330(2) 0.0623(3) Uani 1 d . . .
C1 C -0.87812(9) -0.33906(10) -0.2561(4) 0.0620(5) Uani 1 d . . .
H1 H -0.8537 -0.3132 -0.3604 0.074 Uiso 1 calc . . R
C2 C -0.94596(10) -0.36694(11) -0.3011(5) 0.0791(7) Uani 1 d . . .
H2 H -0.9672 -0.3594 -0.4349 0.095 Uiso 1 calc . . R
C3 C -0.98223(11) -0.40573(12) -0.1491(6) 0.0882(9) Uani 1 d . . .
H3 H -1.0279 -0.4246 -0.1802 0.106 Uiso 1 calc . . R
C4 C -0.95154(13) -0.41665(12) 0.0469(6) 0.0916(9) Uani 1 d . . .
H4 H -0.9763 -0.4430 0.1495 0.110 Uiso 1 calc . . R
C5 C -0.88381(11) -0.38874(10) 0.0942(4) 0.0721(6) Uani 1 d . . .
H5 H -0.8633 -0.3965 0.2287 0.086 Uiso 1 calc . . R
C6 C -0.84601(8) -0.34926(8) -0.0569(3) 0.0509(4) Uani 1 d . . .
C7 C -0.77410(8) -0.32046(8) 0.0026(3) 0.0501(4) Uani 1 d . . .
H7 H -0.7562 -0.3334 0.1367 0.060 Uiso 1 calc . . R
C8 C -0.73214(8) -0.27850(8) -0.1120(3) 0.0434(3) Uani 1 d . . .
H8 H -0.7482 -0.2653 -0.2478 0.052 Uiso 1 calc . . R
C9 C -0.65987(8) -0.25092(8) -0.0352(3) 0.0440(3) Uani 1 d . . .
H9 H -0.6488 -0.2740 0.1015 0.053 Uiso 1 calc . . R
C10 C -0.66446(8) -0.17247(8) 0.0071(3) 0.0471(4) Uani 1 d . . .
C11 C -0.64819(11) -0.14568(11) 0.2061(4) 0.0670(5) Uani 1 d . . .
H11 H -0.6354 -0.1761 0.3166 0.080 Uiso 1 calc . . R
C12 C -0.65049(13) -0.07396(13) 0.2453(5) 0.0853(7) Uani 1 d . . .
H12 H -0.6388 -0.0567 0.3807 0.102 Uiso 1 calc . . R
C13 C -0.66999(11) -0.02869(11) 0.0850(5) 0.0825(8) Uani 1 d . . .
H13 H -0.6717 0.0193 0.1114 0.099 Uiso 1 calc . . R
C14 C -0.68712(10) -0.05415(10) -0.1153(4) 0.0719(6) Uani 1 d . . .
H14 H -0.7007 -0.0234 -0.2242 0.086 Uiso 1 calc . . R
C15 C -0.68415(8) -0.12580(9) -0.1549(4) 0.0565(4) Uani 1 d . . .
H15 H -0.6954 -0.1428 -0.2909 0.068 Uiso 1 calc . . R
C16 C -0.59480(8) -0.26455(8) -0.1887(3) 0.0437(4) Uani 1 d . . .
H16A H -0.5512 -0.2462 -0.1204 0.052 Uiso 1 calc . . R
H16B H -0.6029 -0.2370 -0.3175 0.052 Uiso 1 calc . . R
C17 C -0.57829(8) -0.34088(8) -0.2596(3) 0.0408(3) Uani 1 d . . .
C18 C -0.58211(9) -0.39227(9) -0.0680(3) 0.0515(4) Uani 1 d . . .
H18A H -0.5429 -0.3812 0.0312 0.062 Uiso 1 calc . . R
H18B H -0.6280 -0.3851 0.0069 0.062 Uiso 1 calc . . R
C19 C -0.57623(10) -0.46963(9) -0.1310(3) 0.0621(5) Uani 1 d . . .
H19A H -0.5293 -0.4783 -0.1981 0.075 Uiso 1 calc . . R
H19B H -0.5796 -0.4987 -0.0036 0.075 Uiso 1 calc . . R
C20 C -0.63689(12) -0.48845(10) -0.2852(4) 0.0723(6) Uani 1 d . . .
H20A H -0.6838 -0.4817 -0.2157 0.087 Uiso 1 calc . . R
H20B H -0.6328 -0.5375 -0.3255 0.087 Uiso 1 calc . . R
C21 C -0.63261(11) -0.44283(10) -0.4847(3) 0.0642(5) Uani 1 d . . .
H21A H -0.5888 -0.4548 -0.5642 0.077 Uiso 1 calc . . R
H21B H -0.6743 -0.4529 -0.5759 0.077 Uiso 1 calc . . R
C22 C -0.63150(8) -0.36564(9) -0.4342(3) 0.0454(4) Uani 1 d . . .
C23 C -0.50239(8) -0.33899(8) -0.3676(3) 0.0487(4) Uani 1 d . . .
C24 C -0.49396(10) -0.30791(11) -0.5675(3) 0.0614(5) Uani 1 d . . .
H24 H -0.5348 -0.2904 -0.6384 0.074 Uiso 1 calc . . R
C25 C -0.42562(12) -0.30234(13) -0.6644(4) 0.0840(8) Uani 1 d . . .
H25 H -0.4210 -0.2812 -0.7983 0.101 Uiso 1 calc . . R
C26 C -0.36504(12) -0.32830(14) -0.5608(6) 0.0998(11) Uani 1 d . . .
H26 H -0.3193 -0.3256 -0.6254 0.120 Uiso 1 calc . . R
C27 C -0.37237(11) -0.35794(13) -0.3632(6) 0.0938(9) Uani 1 d . . .
H27 H -0.3312 -0.3747 -0.2924 0.113 Uiso 1 calc . . R
C28 C -0.43986(9) -0.36363(10) -0.2660(4) 0.0674(6) Uani 1 d . . .
H28 H -0.4435 -0.3842 -0.1310 0.081 Uiso 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
O1 C22 1.209(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.386(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 C7 1.474(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.319(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.502(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.520(2) . ?
C9 C16 1.549(2) . ?
C10 C11 1.373(3) . ?
C10 C15 1.392(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.550(2) . ?
C17 C18 1.545(2) . ?
C17 C22 1.534(2) . ?
C17 C23 1.544(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.529(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.512(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.518(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.504(2) . ?
C23 C24 1.387(3) . ?
C23 C28 1.389(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.393(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.375(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.360(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.380(3) . ?
C28 H28 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
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.08(17) . . ?
C1 C6 C7 123.49(16) . . ?
C5 C6 C7 118.43(19) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 C6 127.57(17) . . ?
C8 C7 H7 116.2 . . ?
C7 C8 H8 118.2 . . ?
C7 C8 C9 123.56(16) . . ?
C9 C8 H8 118.2 . . ?
C8 C9 H9 107.6 . . ?
C8 C9 C10 110.52(12) . . ?
C8 C9 C16 114.98(14) . . ?
C10 C9 H9 107.6 . . ?
C10 C9 C16 108.33(12) . . ?
C16 C9 H9 107.6 . . ?
C11 C10 C9 120.68(17) . . ?
C11 C10 C15 118.21(17) . . ?
C15 C10 C9 121.10(16) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C9 C16 H16A 107.6 . . ?
C9 C16 H16B 107.6 . . ?
C9 C16 C17 118.89(13) . . ?
H16A C16 H16B 107.0 . . ?
C17 C16 H16A 107.6 . . ?
C17 C16 H16B 107.6 . . ?
C18 C17 C16 111.45(14) . . ?
C22 C17 C16 111.51(12) . . ?
C22 C17 C18 108.89(13) . . ?
C22 C17 C23 105.67(13) . . ?
C23 C17 C16 106.12(12) . . ?
C23 C17 C18 113.07(13) . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 C17 114.17(15) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 C18 109.87(15) . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
C19 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
C19 C20 C21 110.26(15) . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C20 112.92(16) . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
O1 C22 C17 121.59(15) . . ?
O1 C22 C21 121.14(16) . . ?
C21 C22 C17 117.22(14) . . ?
C24 C23 C17 120.05(15) . . ?
C24 C23 C28 117.45(18) . . ?
C28 C23 C17 122.38(17) . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.4(2) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 119.4 . . ?
C26 C27 C28 121.2(2) . . ?
C28 C27 H27 119.4 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.8(2) . . ?
C27 C28 H28 119.6 . . ?

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
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C6 C7 C8 4.5(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C7 -179.40(17) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 179.70(19) . . . . ?
C5 C6 C7 C8 -175.47(17) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C7 C8 C9 178.97(15) . . . . ?
C7 C8 C9 C10 -110.71(18) . . . . ?
C7 C8 C9 C16 126.28(17) . . . . ?
C8 C9 C10 C11 122.25(18) . . . . ?
C8 C9 C10 C15 -58.7(2) . . . . ?
C8 C9 C16 C17 -55.35(19) . . . . ?
C9 C10 C11 C12 178.44(17) . . . . ?
C9 C10 C15 C14 -179.04(15) . . . . ?
C9 C16 C17 C18 -44.44(18) . . . . ?
C9 C16 C17 C22 77.48(18) . . . . ?
C9 C16 C17 C23 -167.93(13) . . . . ?
C10 C9 C16 C17 -179.53(14) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C10 C15 C14 0.0(2) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C10 0.5(3) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C16 C9 C10 C11 -110.95(17) . . . . ?
C16 C9 C10 C15 68.09(17) . . . . ?
C16 C17 C18 C19 172.45(13) . . . . ?
C16 C17 C22 O1 15.4(2) . . . . ?
C16 C17 C22 C21 -167.24(15) . . . . ?
C16 C17 C23 C24 -71.62(18) . . . . ?
C16 C17 C23 C28 104.23(17) . . . . ?
C17 C18 C19 C20 -58.7(2) . . . . ?
C17 C23 C24 C25 176.84(17) . . . . ?
C17 C23 C28 C27 -176.78(17) . . . . ?
C18 C17 C22 O1 138.82(16) . . . . ?
C18 C17 C22 C21 -43.85(19) . . . . ?
C18 C17 C23 C24 165.91(15) . . . . ?
C18 C17 C23 C28 -18.2(2) . . . . ?
C18 C19 C20 C21 58.9(2) . . . . ?
C19 C20 C21 C22 -53.9(2) . . . . ?
C20 C21 C22 O1 -134.77(18) . . . . ?
C20 C21 C22 C17 47.9(2) . . . . ?
C22 C17 C18 C19 49.03(18) . . . . ?
C22 C17 C23 C24 46.90(18) . . . . ?
C22 C17 C23 C28 -137.25(16) . . . . ?
C23 C17 C18 C19 -68.10(18) . . . . ?
C23 C17 C22 O1 -99.44(18) . . . . ?
C23 C17 C22 C21 77.89(18) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C24 C23 C28 C27 -0.8(3) . . . . ?
C24 C25 C26 C27 -1.2(3) . . . . ?
C25 C26 C27 C28 1.2(4) . . . . ?
C26 C27 C28 C23 -0.2(3) . . . . ?
C28 C23 C24 C25 0.8(3) . . . . ?

_olex2_date_sample_data_collection 2018-03-14
_olex2_submission_special_instructions 'No special instructions were received'
