# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_wuxx1210
_database_code_depnum_ccdc_archive 'CCDC 1040858'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_audit_creation_date             2014-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H19 Br'
_chemical_formula_sum            'C20 H19 Br'
_chemical_formula_weight         339.26
_chemical_absolute_configuration ad
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y, z+1/2'

_cell_length_a                   6.0119(6)
_cell_length_b                   15.8060(14)
_cell_length_c                   8.3765(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.292(9)
_cell_angle_gamma                90.00
_cell_volume                     787.65(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    625
_cell_measurement_temperature    290.92(10)
_cell_measurement_theta_max      21.5290
_cell_measurement_theta_min      3.6560
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2904
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.56
_diffrn_ambient_temperature      290.92(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   40.00   94.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       19.9508  178.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   65.00   96.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       19.9508 -178.0000 -150.0000 21

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00   64.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       19.9508  -19.0000  120.0000 78
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0845764000
_diffrn_orient_matrix_UB_12      0.0290558000
_diffrn_orient_matrix_UB_13      0.0148128000
_diffrn_orient_matrix_UB_21      -0.0317408000
_diffrn_orient_matrix_UB_22      -0.0274136000
_diffrn_orient_matrix_UB_23      0.0598817000
_diffrn_orient_matrix_UB_31      0.0778481000
_diffrn_orient_matrix_UB_32      0.0204209000
_diffrn_orient_matrix_UB_33      0.0592964000
_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                1624
_reflns_number_total             2032
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2032
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.045
_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)+(0.0270P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0999
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_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
Br1 Br 0.70728(15) -0.02268(4) 0.47926(13) 0.0419(2) Uani 1 d . . .
C1 C 0.5134(13) 0.1776(6) 0.7501(9) 0.030(2) Uani 1 d . . .
H1 H 0.5813 0.2115 0.8341 0.036 Uiso 1 calc . . R
C2 C 0.6330(12) 0.1123(5) 0.6927(9) 0.0316(19) Uani 1 d . . .
H2 H 0.7811 0.1023 0.7382 0.038 Uiso 1 calc . . R
C3 C 0.5338(13) 0.0624(4) 0.5688(9) 0.0312(18) Uani 1 d . . .
C4 C 0.3121(12) 0.0739(5) 0.5013(9) 0.0322(19) Uani 1 d . . .
H4 H 0.2454 0.0386 0.4192 0.039 Uiso 1 calc . . R
C5 C 0.1917(13) 0.1391(5) 0.5584(8) 0.0343(19) Uani 1 d . . .
H5 H 0.0425 0.1469 0.5132 0.041 Uiso 1 calc . . R
C6 C 0.2840(12) 0.1933(5) 0.6802(8) 0.0262(17) Uani 1 d . . .
C7 C 0.1509(11) 0.2641(5) 0.7268(8) 0.0273(17) Uani 1 d . . .
H7 H -0.0004 0.2614 0.6837 0.033 Uiso 1 calc . . R
C8 C 0.2043(11) 0.3317(5) 0.8190(8) 0.0254(17) Uani 1 d . . .
C9 C 0.4336(11) 0.3555(5) 0.9129(8) 0.0274(17) Uani 1 d . . .
H9A H 0.5452 0.3610 0.8407 0.033 Uiso 1 calc . . R
H9B H 0.4838 0.3130 0.9936 0.033 Uiso 1 calc . . R
C10 C 0.3953(12) 0.4407(5) 0.9930(8) 0.0273(18) Uani 1 d . . .
H10A H 0.5251 0.4772 0.9939 0.033 Uiso 1 calc . . R
H10B H 0.3676 0.4324 1.1032 0.033 Uiso 1 calc . . R
C11 C 0.1870(11) 0.4795(5) 0.8890(8) 0.0264(17) Uani 1 d . . .
H11 H 0.2323 0.5038 0.7910 0.032 Uiso 1 calc . . R
C12 C 0.0406(11) 0.4017(5) 0.8438(8) 0.0257(17) Uani 1 d . . .
H12A H -0.0450 0.3873 0.9297 0.031 Uiso 1 calc . . R
H12B H -0.0630 0.4118 0.7457 0.031 Uiso 1 calc . . R
C13 C 0.0700(12) 0.5467(5) 0.9747(9) 0.0309(19) Uani 1 d . . .
H13 H -0.0165 0.5261 1.0496 0.037 Uiso 1 calc . . R
C14 C 0.0704(12) 0.6298(5) 0.9605(8) 0.0284(18) Uani 1 d . . .
H14 H -0.0196 0.6588 1.0237 0.034 Uiso 1 calc . . R
C15 C 0.1951(12) 0.6841(5) 0.8572(8) 0.0280(18) Uani 1 d . . .
C16 C 0.1047(13) 0.7631(5) 0.8107(9) 0.0349(19) Uani 1 d . . .
H16 H -0.0269 0.7806 0.8470 0.042 Uiso 1 calc . . R
C17 C 0.2071(16) 0.8158(6) 0.7118(10) 0.050(2) Uani 1 d . . .
H17 H 0.1425 0.8676 0.6791 0.060 Uiso 1 calc . . R
C18 C 0.4086(18) 0.7908(6) 0.6611(10) 0.050(3) Uani 1 d . . .
H18 H 0.4778 0.8253 0.5930 0.060 Uiso 1 calc . . R
C19 C 0.5021(14) 0.7159(6) 0.7121(10) 0.041(2) Uani 1 d . . .
H19 H 0.6382 0.7002 0.6802 0.049 Uiso 1 calc . . R
C20 C 0.4007(13) 0.6616(5) 0.8106(9) 0.0343(19) Uani 1 d . . .
H20 H 0.4692 0.6107 0.8451 0.041 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
Br1 C3 1.920(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(11) . ?
C1 C6 1.440(10) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(10) . ?
C3 C4 1.383(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(9) . ?
C6 C7 1.461(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.330(9) . ?
C8 C9 1.533(9) . ?
C8 C12 1.515(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.537(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.545(9) . ?
C11 H11 0.9800 . ?
C11 C12 1.527(9) . ?
C11 C13 1.511(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.319(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.494(10) . ?
C15 C16 1.394(10) . ?
C15 C20 1.395(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(13) . ?
C18 H18 0.9300 . ?
C18 C19 1.353(12) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(11) . ?
C20 H20 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 119.9 . . ?
C2 C1 C6 120.2(7) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(7) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 Br1 119.8(6) . . ?
C2 C3 C4 121.5(7) . . ?
C4 C3 Br1 118.6(6) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(7) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 122.7(7) . . ?
C6 C5 H5 118.6 . . ?
C1 C6 C7 123.5(7) . . ?
C5 C6 C1 116.9(7) . . ?
C5 C6 C7 119.6(7) . . ?
C6 C7 H7 113.8 . . ?
C8 C7 C6 132.5(6) . . ?
C8 C7 H7 113.8 . . ?
C7 C8 C9 128.2(7) . . ?
C7 C8 C12 124.0(6) . . ?
C12 C8 C9 107.7(6) . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C8 C9 C10 105.0(6) . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C9 C10 C11 105.2(6) . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C10 C11 H11 109.1 . . ?
C12 C11 C10 102.2(6) . . ?
C12 C11 H11 109.1 . . ?
C13 C11 C10 114.0(6) . . ?
C13 C11 H11 109.1 . . ?
C13 C11 C12 113.1(6) . . ?
C8 C12 C11 105.0(6) . . ?
C8 C12 H12A 110.7 . . ?
C8 C12 H12B 110.7 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C11 C13 H13 114.7 . . ?
C14 C13 C11 130.6(8) . . ?
C14 C13 H13 114.7 . . ?
C13 C14 H14 115.4 . . ?
C13 C14 C15 129.2(7) . . ?
C15 C14 H14 115.4 . . ?
C16 C15 C14 117.9(7) . . ?
C16 C15 C20 118.4(8) . . ?
C20 C15 C14 123.6(7) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(8) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.5(8) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(10) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 122.0(9) . . ?
C20 C19 H19 119.0 . . ?
C15 C20 H20 120.3 . . ?
C19 C20 C15 119.4(8) . . ?
C19 C20 H20 120.3 . . ?

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
Br1 C3 C4 C5 -175.6(5) . . . . ?
C1 C2 C3 Br1 175.5(6) . . . . ?
C1 C2 C3 C4 -1.9(12) . . . . ?
C1 C6 C7 C8 9.2(12) . . . . ?
C2 C1 C6 C5 1.6(11) . . . . ?
C2 C1 C6 C7 -176.0(7) . . . . ?
C2 C3 C4 C5 1.8(11) . . . . ?
C3 C4 C5 C6 0.1(11) . . . . ?
C4 C5 C6 C1 -1.7(11) . . . . ?
C4 C5 C6 C7 176.0(7) . . . . ?
C5 C6 C7 C8 -168.3(7) . . . . ?
C6 C1 C2 C3 0.1(12) . . . . ?
C6 C7 C8 C9 -1.9(12) . . . . ?
C6 C7 C8 C12 175.9(7) . . . . ?
C7 C8 C9 C10 178.6(7) . . . . ?
C7 C8 C12 C11 -155.3(6) . . . . ?
C8 C9 C10 C11 -23.4(7) . . . . ?
C9 C8 C12 C11 22.9(7) . . . . ?
C9 C10 C11 C12 37.2(7) . . . . ?
C9 C10 C11 C13 159.6(6) . . . . ?
C10 C11 C12 C8 -36.7(7) . . . . ?
C10 C11 C13 C14 104.1(9) . . . . ?
C11 C13 C14 C15 -2.2(14) . . . . ?
C12 C8 C9 C10 0.5(7) . . . . ?
C12 C11 C13 C14 -139.6(8) . . . . ?
C13 C11 C12 C8 -159.7(6) . . . . ?
C13 C14 C15 C16 153.9(8) . . . . ?
C13 C14 C15 C20 -28.8(12) . . . . ?
C14 C15 C16 C17 -178.2(7) . . . . ?
C14 C15 C20 C19 179.0(6) . . . . ?
C15 C16 C17 C18 -2.0(12) . . . . ?
C16 C15 C20 C19 -3.7(10) . . . . ?
C16 C17 C18 C19 -1.1(13) . . . . ?
C17 C18 C19 C20 1.7(13) . . . . ?
C18 C19 C20 C15 0.8(12) . . . . ?
C20 C15 C16 C17 4.4(10) . . . . ?

_olex2_date_sample_data_collection 2014-12-10
_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_wuxx1118
_database_code_depnum_ccdc_archive 'CCDC 1040859'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_audit_creation_date             2014-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H22 O'
_chemical_formula_sum            'C21 H22 O'
_chemical_formula_weight         290.39
_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      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                   17.7810(8)
_cell_length_b                   15.3478(9)
_cell_length_c                   6.0728(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.114(5)
_cell_angle_gamma                90.00
_cell_volume                     1636.33(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1166
_cell_measurement_temperature    294.68(10)
_cell_measurement_theta_max      23.5940
_cell_measurement_theta_min      3.9810
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85728
_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_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6904
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.48
_diffrn_ambient_temperature      294.68(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00  -12.60   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -57.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   45.00   93.00   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   67.40   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   77.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega  -40.00   44.00   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000  -90.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0303938000
_diffrn_orient_matrix_UB_12      -0.0002032000
_diffrn_orient_matrix_UB_13      -0.0628828000
_diffrn_orient_matrix_UB_21      0.0097265000
_diffrn_orient_matrix_UB_22      0.0430935000
_diffrn_orient_matrix_UB_23      0.0358989000
_diffrn_orient_matrix_UB_31      0.0248024000
_diffrn_orient_matrix_UB_32      -0.0166654000
_diffrn_orient_matrix_UB_33      0.0935201000
_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                1792
_reflns_number_total             3215
_reflns_odcompleteness_completeness 99.74
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.073
_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)+(0.0487P)²+0.6679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1875
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9') \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H8A(0.65) H8B(0.35) H10A(0.65) H10B(0.65) H10C(0.35) H10D(0.35)
 H13A(0.65) H13B(0.65) H13C(0.35) H13D(0.35) C9(0.65) H9(0.65) C9'(0.35)
 H9'(0.35)
4.a Ternary CH refined with riding coordinates:
 C9(H9), C9'(H9')
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C12(H12A,H12B), C13(H13A,H13B), C13(H13C,H13D)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8A), C8(H8B), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
4.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
_atom_site_refinement_flags_adp
O1 O 0.87975(11) 0.12592(14) 0.5528(3) 0.0642(6) Uani 1 d D . . .
C1 C 0.13852(17) 0.0788(2) 0.7196(5) 0.0621(8) Uani 1 d . . . .
H1 H 0.1506 0.0505 0.5944 0.075 Uiso 1 calc . . R .
C2 C 0.06470(18) 0.0749(2) 0.7645(5) 0.0735(10) Uani 1 d . . . .
H2 H 0.0277 0.0443 0.6697 0.088 Uiso 1 calc . . R .
C3 C 0.04623(18) 0.1162(2) 0.9484(6) 0.0782(10) Uani 1 d . . . .
H3 H -0.0034 0.1140 0.9787 0.094 Uiso 1 calc . . R .
C4 C 0.1005(2) 0.1603(3) 1.0861(5) 0.0787(10) Uani 1 d . . . .
H4 H 0.0883 0.1882 1.2116 0.094 Uiso 1 calc . . R .
C5 C 0.17378(18) 0.1638(2) 1.0405(5) 0.0684(9) Uani 1 d . . . .
H5 H 0.2105 0.1942 1.1368 0.082 Uiso 1 calc . . R .
C6 C 0.19434(15) 0.12361(18) 0.8565(4) 0.0514(7) Uani 1 d . . . .
C7 C 0.27407(18) 0.1284(2) 0.8172(5) 0.0736(10) Uani 1 d D . . .
H7 H 0.3063 0.1618 0.9195 0.088 Uiso 1 calc . . R .
C8 C 0.30537(18) 0.0935(3) 0.6637(5) 0.0792(11) Uani 1 d . . . .
H8A H 0.2700 0.0710 0.5486 0.095 Uiso 0.65 calc A 1 R .
H8B H 0.2850 0.0476 0.5733 0.095 Uiso 0.35 calc A 2 R .
C10 C 0.44759(17) 0.1086(2) 0.8085(5) 0.0673(9) Uani 1 d . . . .
H10A H 0.4561 0.0647 0.9246 0.081 Uiso 0.65 calc B 1 R .
H10B H 0.4337 0.1628 0.8738 0.081 Uiso 0.65 calc B 1 R .
H10C H 0.4393 0.0475 0.8371 0.081 Uiso 0.35 calc B 2 R .
H10D H 0.4517 0.1405 0.9479 0.081 Uiso 0.35 calc B 2 R .
C11 C 0.51825(16) 0.12079(18) 0.7028(4) 0.0509(7) Uani 1 d D . . .
C12 C 0.49180(16) 0.1407(2) 0.4602(4) 0.0602(8) Uani 1 d . . . .
H12A H 0.5149 0.1009 0.3661 0.072 Uiso 1 calc D . R .
H12B H 0.5050 0.1999 0.4256 0.072 Uiso 1 calc . . R .
C13 C 0.40530(17) 0.1289(2) 0.4249(5) 0.0726(10) Uani 1 d D . . .
H13A H 0.3802 0.1852 0.4115 0.087 Uiso 0.65 calc C 1 R .
H13B H 0.3886 0.0960 0.2896 0.087 Uiso 0.65 calc C 1 R .
H13C H 0.3800 0.1718 0.3214 0.087 Uiso 0.35 calc C 2 R .
H13D H 0.3907 0.0710 0.3702 0.087 Uiso 0.35 calc C 2 R .
C14 C 0.58893(16) 0.11146(19) 0.8096(4) 0.0563(8) Uani 1 d . . . .
H14 H 0.5925 0.0989 0.9607 0.068 Uiso 1 calc D . R .
C15 C 0.66254(15) 0.11761(17) 0.7295(4) 0.0464(7) Uani 1 d D . . .
C16 C 0.67449(15) 0.16323(18) 0.5399(4) 0.0515(7) Uani 1 d . . . .
H16 H 0.6337 0.1916 0.4547 0.062 Uiso 1 calc D . R .
C17 C 0.74572(16) 0.16731(19) 0.4751(4) 0.0533(7) Uani 1 d D . . .
H17 H 0.7523 0.1984 0.3481 0.064 Uiso 1 calc . . R .
C18 C 0.80685(15) 0.12530(17) 0.5989(4) 0.0477(7) Uani 1 d . . . .
C19 C 0.79618(16) 0.07931(19) 0.7868(4) 0.0540(7) Uani 1 d D . . .
H19 H 0.8369 0.0502 0.8704 0.065 Uiso 1 calc . . R .
C20 C 0.72557(16) 0.07644(19) 0.8505(4) 0.0534(7) Uani 1 d . . . .
H20 H 0.7196 0.0459 0.9790 0.064 Uiso 1 calc D . R .
C21 C 0.89516(18) 0.1757(3) 0.3683(5) 0.0790(10) Uani 1 d . . . .
H21A H 0.8657 0.1535 0.2338 0.118 Uiso 1 calc D . GR .
H21B H 0.9484 0.1718 0.3580 0.118 Uiso 1 calc . . GR .
H21C H 0.8819 0.2355 0.3882 0.118 Uiso 1 calc . . GR .
C9 C 0.3861(2) 0.0803(3) 0.6256(7) 0.0503(10) Uani 0.65 d D 1 . U
H9 H 0.3931 0.0180 0.6002 0.060 Uiso 0.65 calc D 1 R .
C9' C 0.3878(5) 0.1423(6) 0.6495(13) 0.053(2) Uani 0.35 d D 2 . U
H9' H 0.3827 0.2049 0.6755 0.064 Uiso 0.35 calc D 2 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 C18 1.369(3) . ?
O1 C21 1.418(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(4) . ?
C1 C6 1.374(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(4) . ?
C6 C7 1.476(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.277(4) . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C8 C9 1.503(5) . ?
C8 C9' 1.661(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C10 C11 1.510(4) . ?
C10 C9 1.495(5) . ?
C10 C9' 1.415(8) . ?
C11 C12 1.505(4) . ?
C11 C14 1.328(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.530(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C13 H13D 0.9700 . ?
C13 C9 1.514(5) . ?
C13 C9' 1.461(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.470(4) . ?
C15 C16 1.392(3) . ?
C15 C20 1.391(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(4) . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C9 H9 0.9800 . ?
C9' H9' 0.9800 . ?

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
C18 O1 C21 118.2(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C6 C1 C2 121.3(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.9(3) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 117.2(3) . . ?
C1 C6 C7 123.2(3) . . ?
C5 C6 C7 119.6(3) . . ?
C6 C7 H7 115.2 . . ?
C8 C7 C6 129.6(3) . . ?
C8 C7 H7 115.2 . . ?
C7 C8 H8A 112.5 . . ?
C7 C8 H8B 125.1 . . ?
C7 C8 C9 134.9(4) . . ?
C7 C8 C9' 109.8(4) . . ?
H8A C8 H8B 28.5 . . ?
C9 C8 H8A 112.5 . . ?
C9 C8 H8B 95.7 . . ?
C9 C8 C9' 35.0(3) . . ?
C9' C8 H8A 128.8 . . ?
C9' C8 H8B 125.1 . . ?
H10A C10 H10B 108.7 . . ?
H10A C10 H10C 37.6 . . ?
H10A C10 H10D 74.6 . . ?
H10B C10 H10C 134.5 . . ?
H10B C10 H10D 36.9 . . ?
H10C C10 H10D 108.9 . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
C11 C10 H10C 110.9 . . ?
C11 C10 H10D 110.9 . . ?
C9 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
C9 C10 H10C 74.8 . . ?
C9 C10 H10D 137.7 . . ?
C9 C10 C11 106.3(3) . . ?
C9' C10 H10A 139.8 . . ?
C9' C10 H10B 75.8 . . ?
C9' C10 H10C 110.9 . . ?
C9' C10 H10D 110.9 . . ?
C9' C10 C11 104.5(4) . . ?
C9' C10 C9 38.5(4) . . ?
C12 C11 C10 106.8(2) . . ?
C14 C11 C10 124.5(2) . . ?
C14 C11 C12 128.7(2) . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C11 C12 C13 105.3(2) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
C12 C13 H13A 110.3 . . ?
C12 C13 H13B 110.3 . . ?
C12 C13 H13C 111.3 . . ?
C12 C13 H13D 111.3 . . ?
H13A C13 H13B 108.5 . . ?
H13A C13 H13C 35.0 . . ?
H13A C13 H13D 133.9 . . ?
H13B C13 H13C 75.9 . . ?
H13B C13 H13D 37.1 . . ?
H13C C13 H13D 109.2 . . ?
C9 C13 C12 107.2(3) . . ?
C9 C13 H13A 110.3 . . ?
C9 C13 H13B 110.3 . . ?
C9 C13 H13C 135.6 . . ?
C9 C13 H13D 75.0 . . ?
C9' C13 C12 102.1(4) . . ?
C9' C13 H13A 77.9 . . ?
C9' C13 H13B 141.4 . . ?
C9' C13 H13C 111.3 . . ?
C9' C13 H13D 111.3 . . ?
C9' C13 C9 37.7(4) . . ?
C11 C14 H14 114.5 . . ?
C11 C14 C15 130.9(2) . . ?
C15 C14 H14 114.5 . . ?
C16 C15 C14 124.5(2) . . ?
C20 C15 C14 118.8(2) . . ?
C20 C15 C16 116.7(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
O1 C18 C17 125.1(2) . . ?
O1 C18 C19 115.5(2) . . ?
C17 C18 C19 119.3(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 118.9 . . ?
C19 C20 C15 122.2(2) . . ?
C19 C20 H20 118.9 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 C9 C13 113.6(3) . . ?
C8 C9 H9 107.7 . . ?
C10 C9 C8 116.8(3) . . ?
C10 C9 C13 102.9(3) . . ?
C10 C9 H9 107.7 . . ?
C13 C9 H9 107.7 . . ?
C8 C9' H9' 109.1 . . ?
C10 C9' C8 111.9(6) . . ?
C10 C9' C13 109.8(6) . . ?
C10 C9' H9' 109.1 . . ?
C13 C9' C8 107.8(5) . . ?
C13 C9' H9' 109.1 . . ?

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 C18 C19 C20 178.4(2) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C6 C7 C8 -1.5(6) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C1 C6 C7 179.1(3) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C5 C6 C7 C8 177.1(4) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C6 C7 C8 C9 -167.5(4) . . . . ?
C6 C7 C8 C9' 163.0(4) . . . . ?
C7 C8 C9 C10 4.1(7) . . . . ?
C7 C8 C9 C13 -115.4(5) . . . . ?
C7 C8 C9' C10 83.1(7) . . . . ?
C7 C8 C9' C13 -156.1(5) . . . . ?
C10 C11 C12 C13 -6.5(3) . . . . ?
C10 C11 C14 C15 177.3(3) . . . . ?
C11 C10 C9 C8 -159.2(3) . . . . ?
C11 C10 C9 C13 -34.1(4) . . . . ?
C11 C10 C9' C8 150.9(5) . . . . ?
C11 C10 C9' C13 31.3(7) . . . . ?
C11 C12 C13 C9 -14.7(4) . . . . ?
C11 C12 C13 C9' 23.9(5) . . . . ?
C11 C14 C15 C16 23.1(5) . . . . ?
C11 C14 C15 C20 -157.8(3) . . . . ?
C12 C11 C14 C15 0.3(5) . . . . ?
C12 C13 C9 C8 157.3(3) . . . . ?
C12 C13 C9 C10 30.1(4) . . . . ?
C12 C13 C9' C8 -157.2(4) . . . . ?
C12 C13 C9' C10 -35.0(7) . . . . ?
C14 C11 C12 C13 170.9(3) . . . . ?
C14 C15 C16 C17 179.2(3) . . . . ?
C14 C15 C20 C19 -179.9(3) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C15 C20 C19 -0.7(4) . . . . ?
C16 C17 C18 O1 -179.0(3) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C19 C20 C15 1.0(4) . . . . ?
C20 C15 C16 C17 0.0(4) . . . . ?
C21 O1 C18 C17 2.2(4) . . . . ?
C21 O1 C18 C19 -176.9(3) . . . . ?
C9 C8 C9' C10 -59.5(6) . . . . ?
C9 C8 C9' C13 61.3(6) . . . . ?
C9 C10 C11 C12 25.7(4) . . . . ?
C9 C10 C11 C14 -151.8(3) . . . . ?
C9 C10 C9' C8 52.9(6) . . . . ?
C9 C10 C9' C13 -66.7(7) . . . . ?
C9 C13 C9' C8 -54.7(5) . . . . ?
C9 C13 C9' C10 67.5(7) . . . . ?
C9' C8 C9 C10 57.9(6) . . . . ?
C9' C8 C9 C13 -61.6(6) . . . . ?
C9' C10 C11 C12 -14.2(5) . . . . ?
C9' C10 C11 C14 168.2(5) . . . . ?
C9' C10 C9 C8 -66.3(7) . . . . ?
C9' C10 C9 C13 58.8(6) . . . . ?
C9' C13 C9 C8 69.6(6) . . . . ?
C9' C13 C9 C10 -57.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
