# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1491658'
_audit_update_record             
;
2016-07-08 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Br O2'
_chemical_formula_weight         383.27

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.277(2)
_cell_length_b                   19.206(6)
_cell_length_c                   11.294(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.738(6)
_cell_angle_gamma                90.00
_cell_volume                     1791.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    773
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      18.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    2.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4994
_exptl_absorpt_correction_T_max  0.5547
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7943
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         22.20
_reflns_number_total             2251
_reflns_number_gt                1259
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL(Sheldrick, 2008)'
_computing_publication_material  'WINGX (Farrugia,1999)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0194P)²+2.1710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2251
_refine_ls_number_parameters     217
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.22757(9) 0.99324(4) 0.98211(7) 0.1011(3) Uani 1 1 d U . .
O2 O 0.5299(5) 0.5992(3) 1.0776(4) 0.1010(16) Uani 1 1 d U . .
C4 C 0.3880(7) 0.7656(3) 0.9061(5) 0.0647(16) Uani 1 1 d U . .
O1 O 0.0966(6) 0.6423(3) 0.7973(4) 0.1235(19) Uani 1 1 d U . .
C5 C 0.4675(7) 0.8058(3) 0.9914(6) 0.0721(17) Uani 1 1 d U . .
H5 H 0.5580 0.7877 1.0338 0.086 Uiso 1 1 calc R . .
C12 C 0.3639(7) 0.6286(3) 0.8992(5) 0.0696(16) Uani 1 1 d U . .
C15 C 0.2418(7) 0.5900(3) 1.0791(6) 0.0631(16) Uani 1 1 d U . .
C6 C 0.4175(7) 0.8720(3) 1.0162(5) 0.0701(17) Uani 1 1 d U . .
H6 H 0.4731 0.8980 1.0752 0.084 Uiso 1 1 calc R . .
C20 C 0.1166(8) 0.6050(3) 0.9982(6) 0.0674(17) Uani 1 1 d U . .
C3 C 0.2518(7) 0.7942(4) 0.8462(6) 0.0785(18) Uani 1 1 d U . .
H3 H 0.1938 0.7679 0.7888 0.094 Uiso 1 1 calc R . .
C13 C 0.4610(7) 0.6955(3) 0.8770(5) 0.0735(16) Uani 1 1 d U . .
H13 H 0.5559 0.6917 0.9333 0.088 Uiso 1 1 calc R . .
C1 C 0.2852(7) 0.8995(3) 0.9537(5) 0.0669(17) Uani 1 1 d U . .
C14 C 0.3966(8) 0.6054(3) 1.0272(6) 0.0699(17) Uani 1 1 d U . .
C9 C 0.5322(8) 0.6876(4) 0.7543(6) 0.0837(19) Uani 1 1 d U . .
C21 C 0.1799(8) 0.6291(3) 0.8868(6) 0.0799(18) Uani 1 1 d U . .
C2 C 0.2014(7) 0.8603(4) 0.8700(6) 0.084(2) Uani 1 1 d U . .
H2 H 0.1097 0.8784 0.8291 0.100 Uiso 1 1 calc R . .
C16 C 0.2149(8) 0.5642(3) 1.1896(6) 0.0811(19) Uani 1 1 d U . .
H16 H 0.2999 0.5536 1.2446 0.097 Uiso 1 1 calc R . .
C19 C -0.0421(8) 0.5954(4) 1.0264(7) 0.089(2) Uani 1 1 d U . .
H19 H -0.1276 0.6058 0.9718 0.106 Uiso 1 1 calc R . .
C18 C -0.0699(9) 0.5705(4) 1.1348(7) 0.096(2) Uani 1 1 d U . .
H18 H -0.1758 0.5640 1.1553 0.115 Uiso 1 1 calc R . .
C17 C 0.0556(9) 0.5548(4) 1.2151(6) 0.089(2) Uani 1 1 d U . .
H17 H 0.0329 0.5373 1.2889 0.107 Uiso 1 1 calc R . .
C10 C 0.5713(8) 0.6103(3) 0.7583(6) 0.096(2) Uani 1 1 d U . .
H10A H 0.5835 0.5927 0.6788 0.116 Uiso 1 1 calc R . .
H10B H 0.6712 0.6020 0.8059 0.116 Uiso 1 1 calc R . .
C11 C 0.4314(9) 0.5749(4) 0.8127(6) 0.098(2) Uani 1 1 d U . .
H11A H 0.4679 0.5332 0.8551 0.118 Uiso 1 1 calc R . .
H11B H 0.3488 0.5619 0.7518 0.118 Uiso 1 1 calc R . .
C7 C 0.4159(9) 0.7042(4) 0.6481(6) 0.133(3) Uani 1 1 d U . .
H7A H 0.3216 0.6753 0.6503 0.200 Uiso 1 1 calc R . .
H7B H 0.4683 0.6955 0.5762 0.200 Uiso 1 1 calc R . .
H7C H 0.3846 0.7522 0.6509 0.200 Uiso 1 1 calc R . .
C8 C 0.6824(8) 0.7316(4) 0.7503(7) 0.126(3) Uani 1 1 d U . .
H8A H 0.6526 0.7799 0.7469 0.188 Uiso 1 1 calc R . .
H8B H 0.7383 0.7197 0.6813 0.188 Uiso 1 1 calc R . .
H8C H 0.7519 0.7232 0.8203 0.188 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
Br1 C1 1.895(6) . ?
O2 C14 1.214(6) . ?
C4 C5 1.369(7) . ?
C4 C3 1.389(7) . ?
C4 C13 1.521(8) . ?
O1 C21 1.213(7) . ?
C5 C6 1.371(7) . ?
C5 H5 0.9300 . ?
C12 C21 1.519(8) . ?
C12 C14 1.520(8) . ?
C12 C13 1.545(8) . ?
C12 C11 1.550(8) . ?
C15 C20 1.367(7) . ?
C15 C16 1.375(8) . ?
C15 C14 1.473(8) . ?
C6 C1 1.370(7) . ?
C6 H6 0.9300 . ?
C20 C19 1.383(8) . ?
C20 C21 1.469(8) . ?
C3 C2 1.368(8) . ?
C3 H3 0.9300 . ?
C13 C9 1.549(8) . ?
C13 H13 0.9800 . ?
C1 C2 1.363(8) . ?
C9 C8 1.506(8) . ?
C9 C7 1.521(8) . ?
C9 C10 1.520(8) . ?
C2 H2 0.9300 . ?
C16 C17 1.379(8) . ?
C16 H16 0.9300 . ?
C19 C18 1.348(8) . ?
C19 H19 0.9300 . ?
C18 C17 1.367(8) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C10 C11 1.508(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C5 C4 C3 117.2(6) . . ?
C5 C4 C13 118.1(6) . . ?
C3 C4 C13 124.5(6) . . ?
C4 C5 C6 121.9(6) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C21 C12 C14 101.8(5) . . ?
C21 C12 C13 120.6(5) . . ?
C14 C12 C13 109.6(5) . . ?
C21 C12 C11 110.3(5) . . ?
C14 C12 C11 110.8(5) . . ?
C13 C12 C11 103.8(5) . . ?
C20 C15 C16 121.5(6) . . ?
C20 C15 C14 109.5(6) . . ?
C16 C15 C14 129.1(6) . . ?
C1 C6 C5 119.6(6) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C15 C20 C19 120.5(6) . . ?
C15 C20 C21 110.0(6) . . ?
C19 C20 C21 129.5(6) . . ?
C2 C3 C4 121.3(6) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C4 C13 C12 118.9(5) . . ?
C4 C13 C9 117.3(5) . . ?
C12 C13 C9 107.3(5) . . ?
C4 C13 H13 103.8 . . ?
C12 C13 H13 103.8 . . ?
C9 C13 H13 103.8 . . ?
C2 C1 C6 119.8(6) . . ?
C2 C1 Br1 121.4(5) . . ?
C6 C1 Br1 118.8(5) . . ?
O2 C14 C15 125.6(6) . . ?
O2 C14 C12 125.1(6) . . ?
C15 C14 C12 109.4(5) . . ?
C8 C9 C7 109.9(6) . . ?
C8 C9 C10 112.0(6) . . ?
C7 C9 C10 110.5(6) . . ?
C8 C9 C13 109.6(6) . . ?
C7 C9 C13 115.3(6) . . ?
C10 C9 C13 99.3(5) . . ?
O1 C21 C20 124.3(7) . . ?
O1 C21 C12 126.2(7) . . ?
C20 C21 C12 109.3(5) . . ?
C1 C2 C3 120.1(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C15 C16 C17 116.7(6) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 H16 121.6 . . ?
C18 C19 C20 118.5(7) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C18 C17 120.9(7) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C17 C16 121.9(7) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C11 C10 C9 106.6(6) . . ?
C11 C10 H10A 110.4 . . ?
C9 C10 H10A 110.4 . . ?
C11 C10 H10B 110.4 . . ?
C9 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 C12 105.9(5) . . ?
C10 C11 H11A 110.5 . . ?
C12 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C9 C7 H7A 109.5 . . ?
C9 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C9 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C3 C4 C5 C6 -1.1(9) . . . . ?
C13 C4 C5 C6 174.6(5) . . . . ?
C4 C5 C6 C1 -0.6(10) . . . . ?
C16 C15 C20 C19 0.9(10) . . . . ?
C14 C15 C20 C19 -179.5(6) . . . . ?
C16 C15 C20 C21 -177.9(6) . . . . ?
C14 C15 C20 C21 1.7(7) . . . . ?
C5 C4 C3 C2 1.3(9) . . . . ?
C13 C4 C3 C2 -174.0(6) . . . . ?
C5 C4 C13 C12 117.6(6) . . . . ?
C3 C4 C13 C12 -67.1(8) . . . . ?
C5 C4 C13 C9 -110.6(7) . . . . ?
C3 C4 C13 C9 64.7(8) . . . . ?
C21 C12 C13 C4 31.7(8) . . . . ?
C14 C12 C13 C4 -85.9(7) . . . . ?
C11 C12 C13 C4 155.7(6) . . . . ?
C21 C12 C13 C9 -104.4(6) . . . . ?
C14 C12 C13 C9 138.0(5) . . . . ?
C11 C12 C13 C9 19.6(7) . . . . ?
C5 C6 C1 C2 2.0(9) . . . . ?
C5 C6 C1 Br1 -175.7(5) . . . . ?
C20 C15 C14 O2 178.2(7) . . . . ?
C16 C15 C14 O2 -2.3(11) . . . . ?
C20 C15 C14 C12 -3.2(7) . . . . ?
C16 C15 C14 C12 176.3(6) . . . . ?
C21 C12 C14 O2 -178.1(6) . . . . ?
C13 C12 C14 O2 -49.3(9) . . . . ?
C11 C12 C14 O2 64.6(9) . . . . ?
C21 C12 C14 C15 3.3(6) . . . . ?
C13 C12 C14 C15 132.1(5) . . . . ?
C11 C12 C14 C15 -114.0(6) . . . . ?
C4 C13 C9 C8 68.7(8) . . . . ?
C12 C13 C9 C8 -154.4(5) . . . . ?
C4 C13 C9 C7 -55.9(8) . . . . ?
C12 C13 C9 C7 81.0(7) . . . . ?
C4 C13 C9 C10 -173.8(6) . . . . ?
C12 C13 C9 C10 -37.0(7) . . . . ?
C15 C20 C21 O1 175.7(7) . . . . ?
C19 C20 C21 O1 -3.0(12) . . . . ?
C15 C20 C21 C12 0.5(7) . . . . ?
C19 C20 C21 C12 -178.2(6) . . . . ?
C14 C12 C21 O1 -177.4(7) . . . . ?
C13 C12 C21 O1 61.1(9) . . . . ?
C11 C12 C21 O1 -59.8(9) . . . . ?
C14 C12 C21 C20 -2.3(7) . . . . ?
C13 C12 C21 C20 -123.8(6) . . . . ?
C11 C12 C21 C20 115.3(6) . . . . ?
C6 C1 C2 C3 -1.8(10) . . . . ?
Br1 C1 C2 C3 175.9(5) . . . . ?
C4 C3 C2 C1 0.1(10) . . . . ?
C20 C15 C16 C17 -0.6(10) . . . . ?
C14 C15 C16 C17 180.0(6) . . . . ?
C15 C20 C19 C18 -0.5(10) . . . . ?
C21 C20 C19 C18 178.1(7) . . . . ?
C20 C19 C18 C17 -0.3(11) . . . . ?
C19 C18 C17 C16 0.7(12) . . . . ?
C15 C16 C17 C18 -0.3(10) . . . . ?
C8 C9 C10 C11 156.6(6) . . . . ?
C7 C9 C10 C11 -80.6(7) . . . . ?
C13 C9 C10 C11 41.0(7) . . . . ?
C9 C10 C11 C12 -30.4(7) . . . . ?
C21 C12 C11 C10 136.6(6) . . . . ?
C14 C12 C11 C10 -111.5(6) . . . . ?
C13 C12 C11 C10 6.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        22.20
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_llf20161208_0m
_database_code_depnum_ccdc_archive 'CCDC 1523563'
_audit_update_record             
;
2016-12-20 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 O2'
_chemical_formula_weight         372.48

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.914(10)
_cell_length_b                   9.542(11)
_cell_length_c                   13.652(15)
_cell_angle_alpha                86.106(14)
_cell_angle_beta                 80.322(12)
_cell_angle_gamma                67.976(12)
_cell_volume                     1061(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    892
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      21.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5627
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.28
_reflns_number_total             3827
_reflns_number_gt                1865
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'SHELXTL(Sheldrick, 2008)'
_computing_publication_material  'WINGX (Farrugia,1999)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1208P)²+2.2901P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3827
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1976
_refine_ls_R_factor_gt           0.1187
_refine_ls_wR_factor_ref         0.3561
_refine_ls_wR_factor_gt          0.3120
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6485(7) 0.2576(6) 0.6021(4) 0.0990(17) Uani 1 1 d . . .
C13 C 0.9771(7) 0.1060(6) 0.7415(5) 0.0599(16) Uani 1 1 d . . .
C3 C 0.4011(7) 0.5304(6) 0.7979(4) 0.0582(15) Uani 1 1 d . . .
H3A H 0.3799 0.5331 0.7302 0.070 Uiso 1 1 calc R . .
H3B H 0.4287 0.6175 0.8065 0.070 Uiso 1 1 calc R . .
C10 C 0.6954(7) 0.1390(6) 0.8583(5) 0.0649(16) Uani 1 1 d . . .
C25 C 0.7295(7) 0.4734(8) 0.5838(5) 0.0703(18) Uani 1 1 d . . .
C8 C 0.7113(7) 0.3521(6) 0.7444(5) 0.0588(15) Uani 1 1 d . . .
C20 C 0.7767(8) 0.5485(7) 0.6459(5) 0.0686(17) Uani 1 1 d . . .
C26 C 0.6927(7) 0.3476(7) 0.6368(5) 0.0671(17) Uani 1 1 d . . .
C9 C 0.8168(7) 0.2109(6) 0.8005(5) 0.0642(16) Uani 1 1 d . . .
H9 H 0.8511 0.2529 0.8525 0.077 Uiso 1 1 calc R . .
C6 C 0.3828(8) 0.2797(7) 0.9338(5) 0.083(2) Uani 1 1 d . . .
H6A H 0.4045 0.2775 1.0013 0.099 Uiso 1 1 calc R . .
H6B H 0.3577 0.1913 0.9251 0.099 Uiso 1 1 calc R . .
C18 C 0.9886(8) 0.0277(7) 0.6593(5) 0.0718(18) Uani 1 1 d . . .
H18 H 0.8942 0.0377 0.6344 0.086 Uiso 1 1 calc R . .
O2 O 0.8209(10) 0.5150(8) 0.8149(5) 0.145(3) Uani 1 1 d . . .
C19 C 0.7758(10) 0.4803(8) 0.7439(6) 0.083(2) Uani 1 1 d . . .
C1 C 0.0992(8) 0.6814(7) 0.8580(6) 0.085(2) Uani 1 1 d . . .
H1A H 0.1308 0.7574 0.8205 0.128 Uiso 1 1 calc R . .
H1B H 0.0444 0.7195 0.9230 0.128 Uiso 1 1 calc R . .
H1C H 0.0266 0.6558 0.8244 0.128 Uiso 1 1 calc R . .
C14 C 1.1167(8) 0.0964(8) 0.7763(6) 0.083(2) Uani 1 1 d . . .
H14 H 1.1100 0.1518 0.8314 0.099 Uiso 1 1 calc R . .
C11 C 0.6905(8) 0.0008(8) 0.8126(5) 0.082(2) Uani 1 1 d . . .
H11A H 0.7943 -0.0809 0.8119 0.124 Uiso 1 1 calc R . .
H11B H 0.6679 0.0237 0.7458 0.124 Uiso 1 1 calc R . .
H11C H 0.6060 -0.0281 0.8512 0.124 Uiso 1 1 calc R . .
C17 C 1.1391(12) -0.0663(9) 0.6126(6) 0.098(3) Uani 1 1 d . . .
H17 H 1.1432 -0.1215 0.5580 0.117 Uiso 1 1 calc R . .
C5 C 0.5329(8) 0.2712(8) 0.8635(7) 0.124(4) Uani 1 1 d . . .
H5 H 0.4998 0.2332 0.8091 0.148 Uiso 1 1 calc R . .
C16 C 1.2804(11) -0.0813(10) 0.6429(8) 0.110(3) Uani 1 1 d . . .
H16 H 1.3806 -0.1439 0.6093 0.132 Uiso 1 1 calc R . .
C4 C 0.5435(9) 0.3916(8) 0.8116(7) 0.117(4) Uani 1 1 d . . .
H4 H 0.5746 0.4329 0.8654 0.141 Uiso 1 1 calc R . .
C12 C 0.7442(11) 0.0905(8) 0.9616(5) 0.104(3) Uani 1 1 d . . .
H12A H 0.8488 0.0088 0.9549 0.156 Uiso 1 1 calc R . .
H12B H 0.6635 0.0580 1.0014 0.156 Uiso 1 1 calc R . .
H12C H 0.7509 0.1745 0.9931 0.156 Uiso 1 1 calc R . .
C21 C 0.8202(11) 0.6738(9) 0.6122(8) 0.114(3) Uani 1 1 d . . .
H21 H 0.8561 0.7242 0.6536 0.137 Uiso 1 1 calc R . .
C24 C 0.7186(11) 0.5147(11) 0.4836(7) 0.112(3) Uani 1 1 d . . .
H24 H 0.6872 0.4627 0.4408 0.135 Uiso 1 1 calc R . .
C15 C 1.2723(10) 0.0001(12) 0.7265(9) 0.117(3) Uani 1 1 d . . .
H15 H 1.3679 -0.0085 0.7495 0.140 Uiso 1 1 calc R . .
C22 C 0.8063(12) 0.7172(12) 0.5144(10) 0.126(4) Uani 1 1 d . . .
H22 H 0.8302 0.8009 0.4896 0.152 Uiso 1 1 calc R . .
C7 C 0.2372(9) 0.4182(9) 0.9201(8) 0.130(4) Uani 1 1 d . . .
H7A H 0.1653 0.3857 0.8893 0.157 Uiso 1 1 calc R . .
H7B H 0.1803 0.4531 0.9861 0.157 Uiso 1 1 calc R . .
C23 C 0.7590(13) 0.6409(15) 0.4543(9) 0.144(5) Uani 1 1 d . . .
H23 H 0.7529 0.6743 0.3890 0.173 Uiso 1 1 calc R . .
C2 C 0.2487(10) 0.5433(10) 0.8675(8) 0.135(4) Uani 1 1 d . . .
H2 H 0.2787 0.5836 0.9223 0.162 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
O1 C26 1.220(7) . ?
C13 C18 1.358(9) . ?
C13 C14 1.375(9) . ?
C13 C9 1.530(8) . ?
C3 C4 1.479(8) . ?
C3 C2 1.491(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C10 C11 1.515(9) . ?
C10 C5 1.517(9) . ?
C10 C12 1.537(9) . ?
C10 C9 1.569(8) . ?
C25 C20 1.356(9) . ?
C25 C24 1.406(10) . ?
C25 C26 1.473(9) . ?
C8 C26 1.512(9) . ?
C8 C19 1.534(9) . ?
C8 C4 1.544(9) . ?
C8 C9 1.561(8) . ?
C20 C21 1.417(10) . ?
C20 C19 1.447(10) . ?
C9 H9 0.9800 . ?
C6 C5 1.489(9) . ?
C6 C7 1.492(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C18 C17 1.378(10) . ?
C18 H18 0.9300 . ?
O2 C19 1.219(8) . ?
C1 C2 1.500(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C14 C15 1.429(11) . ?
C14 H14 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C17 C16 1.345(12) . ?
C17 H17 0.9300 . ?
C5 C4 1.333(9) . ?
C5 H5 0.9800 . ?
C16 C15 1.400(13) . ?
C16 H16 0.9300 . ?
C4 H4 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C21 C22 1.383(13) . ?
C21 H21 0.9300 . ?
C24 C23 1.397(15) . ?
C24 H24 0.9300 . ?
C15 H15 0.9300 . ?
C22 C23 1.344(15) . ?
C22 H22 0.9300 . ?
C7 C2 1.379(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C23 H23 0.9300 . ?
C2 H2 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 C13 C14 120.0(6) . . ?
C18 C13 C9 125.0(6) . . ?
C14 C13 C9 115.0(6) . . ?
C4 C3 C2 114.0(6) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C11 C10 C5 111.9(6) . . ?
C11 C10 C12 106.4(5) . . ?
C5 C10 C12 112.1(7) . . ?
C11 C10 C9 116.9(5) . . ?
C5 C10 C9 101.6(5) . . ?
C12 C10 C9 108.0(6) . . ?
C20 C25 C24 123.0(7) . . ?
C20 C25 C26 110.2(6) . . ?
C24 C25 C26 126.8(8) . . ?
C26 C8 C19 102.1(5) . . ?
C26 C8 C4 110.4(6) . . ?
C19 C8 C4 110.9(6) . . ?
C26 C8 C9 122.7(5) . . ?
C19 C8 C9 110.4(5) . . ?
C4 C8 C9 100.4(5) . . ?
C25 C20 C21 121.1(7) . . ?
C25 C20 C19 110.3(6) . . ?
C21 C20 C19 128.6(8) . . ?
O1 C26 C25 126.8(7) . . ?
O1 C26 C8 124.9(6) . . ?
C25 C26 C8 108.3(6) . . ?
C13 C9 C8 116.9(5) . . ?
C13 C9 C10 118.2(5) . . ?
C8 C9 C10 106.4(5) . . ?
C13 C9 H9 104.6 . . ?
C8 C9 H9 104.6 . . ?
C10 C9 H9 104.6 . . ?
C5 C6 C7 113.3(5) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C13 C18 C17 120.5(7) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
O2 C19 C20 126.7(7) . . ?
O2 C19 C8 124.5(7) . . ?
C20 C19 C8 108.7(6) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 C15 119.0(8) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C17 C18 122.6(9) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C4 C5 C6 121.7(6) . . ?
C4 C5 C10 113.3(6) . . ?
C6 C5 C10 124.1(6) . . ?
C4 C5 H5 93.3 . . ?
C6 C5 H5 93.3 . . ?
C10 C5 H5 93.3 . . ?
C17 C16 C15 118.1(8) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C5 C4 C3 124.1(6) . . ?
C5 C4 C8 111.2(6) . . ?
C3 C4 C8 122.6(6) . . ?
C5 C4 H4 94.8 . . ?
C3 C4 H4 94.8 . . ?
C8 C4 H4 94.8 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C22 C21 C20 116.3(9) . . ?
C22 C21 H21 121.9 . . ?
C20 C21 H21 121.9 . . ?
C23 C24 C25 113.9(9) . . ?
C23 C24 H24 123.0 . . ?
C25 C24 H24 123.0 . . ?
C16 C15 C14 119.8(8) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C23 C22 C21 121.4(9) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C2 C7 C6 123.0(7) . . ?
C2 C7 H7A 106.6 . . ?
C6 C7 H7A 106.6 . . ?
C2 C7 H7B 106.6 . . ?
C6 C7 H7B 106.6 . . ?
H7A C7 H7B 106.5 . . ?
C22 C23 C24 124.3(10) . . ?
C22 C23 H23 117.9 . . ?
C24 C23 H23 117.9 . . ?
C7 C2 C3 120.0(6) . . ?
C7 C2 C1 121.1(7) . . ?
C3 C2 C1 117.1(6) . . ?
C7 C2 H2 94.5 . . ?
C3 C2 H2 94.5 . . ?
C1 C2 H2 94.5 . . ?

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
C24 C25 C20 C21 -0.8(11) . . . . ?
C26 C25 C20 C21 179.5(6) . . . . ?
C24 C25 C20 C19 179.9(7) . . . . ?
C26 C25 C20 C19 0.1(8) . . . . ?
C20 C25 C26 O1 -179.4(6) . . . . ?
C24 C25 C26 O1 0.9(11) . . . . ?
C20 C25 C26 C8 3.3(7) . . . . ?
C24 C25 C26 C8 -176.5(7) . . . . ?
C19 C8 C26 O1 177.6(6) . . . . ?
C4 C8 C26 O1 -64.4(8) . . . . ?
C9 C8 C26 O1 53.5(9) . . . . ?
C19 C8 C26 C25 -4.9(6) . . . . ?
C4 C8 C26 C25 113.0(6) . . . . ?
C9 C8 C26 C25 -129.1(6) . . . . ?
C18 C13 C9 C8 -62.2(8) . . . . ?
C14 C13 C9 C8 116.5(6) . . . . ?
C18 C13 C9 C10 67.0(8) . . . . ?
C14 C13 C9 C10 -114.4(6) . . . . ?
C26 C8 C9 C13 38.1(8) . . . . ?
C19 C8 C9 C13 -82.2(7) . . . . ?
C4 C8 C9 C13 160.7(6) . . . . ?
C26 C8 C9 C10 -96.5(6) . . . . ?
C19 C8 C9 C10 143.2(5) . . . . ?
C4 C8 C9 C10 26.1(7) . . . . ?
C11 C10 C9 C13 -32.5(8) . . . . ?
C5 C10 C9 C13 -154.6(7) . . . . ?
C12 C10 C9 C13 87.4(7) . . . . ?
C11 C10 C9 C8 101.3(6) . . . . ?
C5 C10 C9 C8 -20.8(7) . . . . ?
C12 C10 C9 C8 -138.8(5) . . . . ?
C14 C13 C18 C17 2.7(10) . . . . ?
C9 C13 C18 C17 -178.7(6) . . . . ?
C25 C20 C19 O2 175.4(8) . . . . ?
C21 C20 C19 O2 -3.9(14) . . . . ?
C25 C20 C19 C8 -3.4(8) . . . . ?
C21 C20 C19 C8 177.3(7) . . . . ?
C26 C8 C19 O2 -173.8(8) . . . . ?
C4 C8 C19 O2 68.6(10) . . . . ?
C9 C8 C19 O2 -41.7(10) . . . . ?
C26 C8 C19 C20 5.0(7) . . . . ?
C4 C8 C19 C20 -112.6(7) . . . . ?
C9 C8 C19 C20 137.1(6) . . . . ?
C18 C13 C14 C15 -1.8(10) . . . . ?
C9 C13 C14 C15 179.5(6) . . . . ?
C13 C18 C17 C16 -2.5(11) . . . . ?
C7 C6 C5 C4 15.2(15) . . . . ?
C7 C6 C5 C10 -177.0(9) . . . . ?
C11 C10 C5 C4 -119.0(10) . . . . ?
C12 C10 C5 C4 121.5(10) . . . . ?
C9 C10 C5 C4 6.4(12) . . . . ?
C11 C10 C5 C6 72.2(12) . . . . ?
C12 C10 C5 C6 -47.3(12) . . . . ?
C9 C10 C5 C6 -162.3(9) . . . . ?
C18 C17 C16 C15 1.3(13) . . . . ?
C6 C5 C4 C3 -16.1(18) . . . . ?
C10 C5 C4 C3 174.8(8) . . . . ?
C6 C5 C4 C8 -179.9(9) . . . . ?
C10 C5 C4 C8 11.0(14) . . . . ?
C2 C3 C4 C5 15.2(15) . . . . ?
C2 C3 C4 C8 177.2(9) . . . . ?
C26 C8 C4 C5 107.6(10) . . . . ?
C19 C8 C4 C5 -140.0(9) . . . . ?
C9 C8 C4 C5 -23.3(11) . . . . ?
C26 C8 C4 C3 -56.5(10) . . . . ?
C19 C8 C4 C3 56.0(11) . . . . ?
C9 C8 C4 C3 172.6(8) . . . . ?
C25 C20 C21 C22 2.1(12) . . . . ?
C19 C20 C21 C22 -178.7(8) . . . . ?
C20 C25 C24 C23 -0.6(12) . . . . ?
C26 C25 C24 C23 179.1(7) . . . . ?
C17 C16 C15 C14 -0.4(13) . . . . ?
C13 C14 C15 C16 0.7(12) . . . . ?
C20 C21 C22 C23 -2.0(15) . . . . ?
C5 C6 C7 C2 -16.3(16) . . . . ?
C21 C22 C23 C24 0.7(19) . . . . ?
C25 C24 C23 C22 0.7(16) . . . . ?
C6 C7 C2 C3 17.5(18) . . . . ?
C6 C7 C2 C1 -178.4(9) . . . . ?
C4 C3 C2 C7 -15.4(15) . . . . ?
C4 C3 C2 C1 179.9(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.28
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.055
