# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1992385'
loop_
_audit_author_name
_audit_author_address
'Lu Liu'
;East China Normal University
China
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 Br O3'
_chemical_formula_weight         413.30

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                   9.9479(4)
_cell_length_b                   18.8377(8)
_cell_length_c                   10.7780(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.3710(10)
_cell_angle_gamma                90.00
_cell_volume                     1965.00(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5448
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      22.06

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5340
_exptl_absorpt_correction_T_max  0.5896
_exptl_absorpt_process_details   sadabs

_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 Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22719
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3462
_reflns_number_gt                2620
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0319P)²+0.8828P] 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         3462
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.64694(4) 0.158247(17) 0.10882(3) 0.09033(16) Uani 1 1 d . . .
O1 O 0.08545(16) 0.43838(9) 0.11957(15) 0.0553(4) Uani 1 1 d . . .
O2 O 0.01888(15) 0.45852(8) 0.30229(14) 0.0453(4) Uani 1 1 d . . .
O3 O 0.32955(16) 0.38410(8) 0.11603(13) 0.0466(4) Uani 1 1 d . . .
H3B H 0.2516 0.4010 0.1025 0.070 Uiso 1 1 calc R . .
C1 C 0.3808(2) 0.37739(11) 0.24404(19) 0.0364(5) Uani 1 1 d . . .
C2 C 0.4747(2) 0.32002(11) 0.2816(2) 0.0373(5) Uani 1 1 d . . .
C3 C 0.5074(2) 0.27327(11) 0.1908(2) 0.0431(5) Uani 1 1 d . . .
H3A H 0.4675 0.2792 0.1045 0.052 Uiso 1 1 calc R . .
C4 C 0.5979(3) 0.21941(12) 0.2309(2) 0.0512(6) Uani 1 1 d . . .
C5 C 0.6588(3) 0.20787(14) 0.3597(3) 0.0597(7) Uani 1 1 d . . .
H5A H 0.7200 0.1704 0.3845 0.072 Uiso 1 1 calc R . .
C6 C 0.6272(3) 0.25202(13) 0.4478(3) 0.0556(7) Uani 1 1 d . . .
H6A H 0.6673 0.2443 0.5336 0.067 Uiso 1 1 calc R . .
C7 C 0.5351(2) 0.30956(12) 0.4130(2) 0.0424(5) Uani 1 1 d . . .
C8 C 0.5009(3) 0.35614(12) 0.5027(2) 0.0476(6) Uani 1 1 d . . .
H8A H 0.5394 0.3497 0.5892 0.057 Uiso 1 1 calc R . .
C9 C 0.4120(2) 0.41036(12) 0.4636(2) 0.0444(6) Uani 1 1 d . . .
H9A H 0.3916 0.4408 0.5246 0.053 Uiso 1 1 calc R . .
C10 C 0.3489(2) 0.42262(11) 0.3339(2) 0.0371(5) Uani 1 1 d . . .
C11 C 0.2496(2) 0.48492(11) 0.3012(2) 0.0387(5) Uani 1 1 d . . .
H11A H 0.2374 0.5040 0.3825 0.046 Uiso 1 1 calc R . .
C12 C 0.2968(2) 0.54664(11) 0.2306(2) 0.0390(5) Uani 1 1 d . . .
C13 C 0.2146(3) 0.60662(13) 0.2076(3) 0.0576(7) Uani 1 1 d . . .
H13A H 0.1306 0.6072 0.2315 0.069 Uiso 1 1 calc R . .
C14 C 0.2548(3) 0.66531(14) 0.1501(3) 0.0682(8) Uani 1 1 d . . .
H14A H 0.1978 0.7050 0.1353 0.082 Uiso 1 1 calc R . .
C15 C 0.3780(3) 0.66583(14) 0.1145(3) 0.0651(8) Uani 1 1 d . . .
H15A H 0.4058 0.7059 0.0768 0.078 Uiso 1 1 calc R . .
C16 C 0.4601(3) 0.60646(13) 0.1352(3) 0.0582(7) Uani 1 1 d . . .
H16A H 0.5434 0.6060 0.1098 0.070 Uiso 1 1 calc R . .
C17 C 0.4201(2) 0.54738(12) 0.1932(2) 0.0464(6) Uani 1 1 d . . .
H17A H 0.4770 0.5076 0.2073 0.056 Uiso 1 1 calc R . .
C18 C 0.1086(2) 0.45806(12) 0.2296(2) 0.0416(5) Uani 1 1 d . . .
C19 C -0.1240(2) 0.43005(13) 0.2553(2) 0.0521(6) Uani 1 1 d . . .
C20 C -0.1995(3) 0.47419(16) 0.1442(3) 0.0683(8) Uani 1 1 d . . .
H20A H -0.1606 0.4658 0.0719 0.102 Uiso 1 1 calc R . .
H20B H -0.1904 0.5236 0.1667 0.102 Uiso 1 1 calc R . .
H20C H -0.2955 0.4614 0.1233 0.102 Uiso 1 1 calc R . .
C21 C -0.1841(3) 0.44067(17) 0.3709(3) 0.0754(9) Uani 1 1 d . . .
H21A H -0.1896 0.4905 0.3876 0.113 Uiso 1 1 calc R . .
H21B H -0.1259 0.4179 0.4435 0.113 Uiso 1 1 calc R . .
H21C H -0.2750 0.4203 0.3549 0.113 Uiso 1 1 calc R . .
C22 C -0.1149(3) 0.35213(15) 0.2235(3) 0.0787(9) Uani 1 1 d . . .
H22A H -0.0777 0.3474 0.1492 0.118 Uiso 1 1 calc R . .
H22B H -0.2055 0.3314 0.2069 0.118 Uiso 1 1 calc R . .
H22C H -0.0557 0.3282 0.2941 0.118 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 C4 1.895(2) . ?
O1 C18 1.213(3) . ?
O2 C18 1.317(3) . ?
O2 C19 1.494(3) . ?
O3 C1 1.362(2) . ?
O3 H3B 0.8200 . ?
C1 C10 1.381(3) . ?
C1 C2 1.425(3) . ?
C2 C3 1.410(3) . ?
C2 C7 1.418(3) . ?
C3 C4 1.359(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(4) . ?
C5 C6 1.353(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.413(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.404(3) . ?
C8 C9 1.353(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.413(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.521(3) . ?
C11 C12 1.522(3) . ?
C11 C18 1.523(3) . ?
C11 H11A 0.9800 . ?
C12 C17 1.377(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.371(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.366(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C19 C20 1.507(4) . ?
C19 C22 1.515(4) . ?
C19 C21 1.516(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C18 O2 C19 121.24(18) . . ?
C1 O3 H3B 109.5 . . ?
O3 C1 C10 124.10(19) . . ?
O3 C1 C2 115.20(18) . . ?
C10 C1 C2 120.70(19) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C1 119.2(2) . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 122.3(2) . . ?
C3 C4 Br1 119.42(19) . . ?
C5 C4 Br1 118.24(18) . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 H6A 119.1 . . ?
C7 C6 H6A 119.1 . . ?
C8 C7 C6 122.9(2) . . ?
C8 C7 C2 119.1(2) . . ?
C6 C7 C2 118.1(2) . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 122.7(2) . . ?
C8 C9 H9A 118.6 . . ?
C10 C9 H9A 118.6 . . ?
C1 C10 C9 118.1(2) . . ?
C1 C10 C11 123.77(19) . . ?
C9 C10 C11 118.11(19) . . ?
C10 C11 C12 116.52(17) . . ?
C10 C11 C18 109.47(17) . . ?
C12 C11 C18 110.76(17) . . ?
C10 C11 H11A 106.5 . . ?
C12 C11 H11A 106.5 . . ?
C18 C11 H11A 106.5 . . ?
C17 C12 C13 118.0(2) . . ?
C17 C12 C11 123.53(19) . . ?
C13 C12 C11 118.5(2) . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C12 C17 C16 120.7(2) . . ?
C12 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
O1 C18 O2 125.6(2) . . ?
O1 C18 C11 122.8(2) . . ?
O2 C18 C11 111.60(19) . . ?
O2 C19 C20 109.35(19) . . ?
O2 C19 C22 108.8(2) . . ?
C20 C19 C22 113.6(2) . . ?
O2 C19 C21 101.5(2) . . ?
C20 C19 C21 111.2(2) . . ?
C22 C19 C21 111.7(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O3 C1 C2 C3 -1.6(3) . . . . ?
C10 C1 C2 C3 179.6(2) . . . . ?
O3 C1 C2 C7 178.98(18) . . . . ?
C10 C1 C2 C7 0.2(3) . . . . ?
C7 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C4 179.7(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C2 C3 C4 Br1 -177.95(16) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
Br1 C4 C5 C6 178.5(2) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 -179.9(2) . . . . ?
C5 C6 C7 C2 0.4(4) . . . . ?
C3 C2 C7 C8 -179.5(2) . . . . ?
C1 C2 C7 C8 -0.1(3) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
C1 C2 C7 C6 179.6(2) . . . . ?
C6 C7 C8 C9 180.0(2) . . . . ?
C2 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
O3 C1 C10 C9 -178.58(19) . . . . ?
C2 C1 C10 C9 0.0(3) . . . . ?
O3 C1 C10 C11 1.4(3) . . . . ?
C2 C1 C10 C11 -179.95(19) . . . . ?
C8 C9 C10 C1 -0.5(3) . . . . ?
C8 C9 C10 C11 179.5(2) . . . . ?
C1 C10 C11 C12 -68.3(3) . . . . ?
C9 C10 C11 C12 111.7(2) . . . . ?
C1 C10 C11 C18 58.3(3) . . . . ?
C9 C10 C11 C18 -121.7(2) . . . . ?
C10 C11 C12 C17 1.8(3) . . . . ?
C18 C11 C12 C17 -124.2(2) . . . . ?
C10 C11 C12 C13 -175.16(19) . . . . ?
C18 C11 C12 C13 58.9(3) . . . . ?
C17 C12 C13 C14 -0.4(4) . . . . ?
C11 C12 C13 C14 176.7(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C13 C12 C17 C16 0.3(3) . . . . ?
C11 C12 C17 C16 -176.7(2) . . . . ?
C15 C16 C17 C12 0.5(4) . . . . ?
C19 O2 C18 O1 3.3(3) . . . . ?
C19 O2 C18 C11 -176.02(18) . . . . ?
C10 C11 C18 O1 -73.6(3) . . . . ?
C12 C11 C18 O1 56.2(3) . . . . ?
C10 C11 C18 O2 105.7(2) . . . . ?
C12 C11 C18 O2 -124.43(19) . . . . ?
C18 O2 C19 C20 -63.6(3) . . . . ?
C18 O2 C19 C22 61.0(3) . . . . ?
C18 O2 C19 C21 178.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1992387'
loop_
_audit_author_name
_audit_author_address
'Lu Liu'
;East China Normal University
China
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.34

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           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   16.4021(8)
_cell_length_b                   9.0310(4)
_cell_length_c                   12.2547(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.1250(10)
_cell_angle_gamma                90.00
_cell_volume                     1629.80(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3534
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      22.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   sadabs

_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 Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9126
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2499
_reflns_number_gt                2203
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0554P)²+0.3492P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(13)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2499
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.057
_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 0.65293(11) 0.6203(2) 0.65064(18) 0.0861(7) Uani 1 1 d . . .
O2 O 0.68834(11) 0.7743(2) 0.80442(16) 0.0793(6) Uani 1 1 d . . .
O3 O 0.35784(9) 0.70698(18) 0.50362(12) 0.0566(4) Uani 1 1 d . . .
H3B H 0.3029 0.6937 0.4658 0.085 Uiso 1 1 calc R . .
C1 C 0.51348(16) 0.6128(2) 0.81110(19) 0.0548(6) Uani 1 1 d . . .
H1A H 0.5741 0.6286 0.8647 0.066 Uiso 1 1 calc R . .
C2 C 0.4593(2) 0.5311(3) 0.8484(2) 0.0663(7) Uani 1 1 d . . .
H2A H 0.4831 0.4921 0.9266 0.080 Uiso 1 1 calc R . .
C3 C 0.37025(19) 0.5079(3) 0.7695(2) 0.0660(7) Uani 1 1 d . . .
H3A H 0.3340 0.4529 0.7953 0.079 Uiso 1 1 calc R . .
C4 C 0.33257(16) 0.5636(3) 0.6529(2) 0.0576(6) Uani 1 1 d . . .
C5 C 0.38806(13) 0.6463(2) 0.61663(18) 0.0440(5) Uani 1 1 d . . .
C6 C 0.47912(13) 0.6718(2) 0.69505(17) 0.0420(5) Uani 1 1 d . . .
C7 C 0.53427(13) 0.7638(2) 0.64772(18) 0.0437(5) Uani 1 1 d . . .
H7A H 0.5129 0.7388 0.5617 0.052 Uiso 1 1 calc R . .
C8 C 0.52080(13) 0.9295(2) 0.65460(19) 0.0450(5) Uani 1 1 d . . .
C9 C 0.49125(18) 1.0141(3) 0.5511(2) 0.0643(6) Uani 1 1 d . . .
H9A H 0.4789 0.9688 0.4773 0.077 Uiso 1 1 calc R . .
C10 C 0.4796(2) 1.1647(3) 0.5544(3) 0.0854(9) Uani 1 1 d . . .
H10A H 0.4595 1.2203 0.4834 0.103 Uiso 1 1 calc R . .
C11 C 0.4977(2) 1.2324(3) 0.6626(4) 0.0858(9) Uani 1 1 d . . .
H11A H 0.4907 1.3343 0.6655 0.103 Uiso 1 1 calc R . .
C12 C 0.5260(2) 1.1501(3) 0.7660(3) 0.0812(9) Uani 1 1 d . . .
H12A H 0.5379 1.1959 0.8395 0.097 Uiso 1 1 calc R . .
C13 C 0.53695(17) 0.9996(3) 0.7623(2) 0.0611(6) Uani 1 1 d . . .
H13A H 0.5555 0.9443 0.8333 0.073 Uiso 1 1 calc R . .
C14 C 0.2346(2) 0.5340(4) 0.5666(3) 0.0950(11) Uani 1 1 d . . .
H14A H 0.2071 0.4754 0.6069 0.142 Uiso 1 1 calc R . .
H14B H 0.2316 0.4814 0.4968 0.142 Uiso 1 1 calc R . .
H14C H 0.2027 0.6263 0.5412 0.142 Uiso 1 1 calc R . .
C15 C 0.63404(14) 0.7217(2) 0.7121(2) 0.0516(5) Uani 1 1 d . . .
C16 C 0.7459(2) 0.5595(5) 0.6984(4) 0.1194(18) Uani 1 1 d . . .
H16A H 0.7892 0.6271 0.7586 0.143 Uiso 1 1 calc R . .
C18 C 0.7660(3) 0.5463(7) 0.5909(7) 0.174(3) Uani 1 1 d . . .
H18A H 0.8258 0.5058 0.6164 0.262 Uiso 1 1 calc R . .
H18B H 0.7630 0.6424 0.5559 0.262 Uiso 1 1 calc R . .
H18C H 0.7222 0.4821 0.5316 0.262 Uiso 1 1 calc R . .
C17 C 0.7444(4) 0.4181(8) 0.7550(6) 0.198(3) Uani 1 1 d . . .
H17A H 0.7311 0.4347 0.8228 0.296 Uiso 1 1 calc R . .
H17B H 0.8026 0.3710 0.7827 0.296 Uiso 1 1 calc R . .
H17C H 0.6986 0.3555 0.6967 0.296 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 C15 1.306(3) . ?
O1 C16 1.478(3) . ?
O2 C15 1.188(3) . ?
O3 C5 1.363(2) . ?
O3 H3B 0.8200 . ?
C1 C2 1.379(4) . ?
C1 C6 1.385(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.367(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.393(3) . ?
C4 C14 1.509(4) . ?
C5 C6 1.394(3) . ?
C6 C7 1.519(3) . ?
C7 C15 1.519(3) . ?
C7 C8 1.520(3) . ?
C7 H7A 0.9800 . ?
C8 C9 1.374(3) . ?
C8 C13 1.381(3) . ?
C9 C10 1.376(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.369(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.363(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C17 1.459(8) . ?
C16 C18 1.496(8) . ?
C16 H16A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C15 O1 C16 119.8(2) . . ?
C5 O3 H3B 109.5 . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 122.0(2) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 C14 121.0(2) . . ?
C5 C4 C14 121.0(2) . . ?
O3 C5 C4 122.91(18) . . ?
O3 C5 C6 115.72(18) . . ?
C4 C5 C6 121.37(18) . . ?
C1 C6 C5 118.21(19) . . ?
C1 C6 C7 124.12(18) . . ?
C5 C6 C7 117.66(17) . . ?
C6 C7 C15 110.56(17) . . ?
C6 C7 C8 113.06(17) . . ?
C15 C7 C8 111.54(17) . . ?
C6 C7 H7A 107.1 . . ?
C15 C7 H7A 107.1 . . ?
C8 C7 H7A 107.1 . . ?
C9 C8 C13 118.0(2) . . ?
C9 C8 C7 119.8(2) . . ?
C13 C8 C7 122.2(2) . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C8 120.8(3) . . ?
C12 C13 H13A 119.6 . . ?
C8 C13 H13A 119.6 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 O1 124.1(2) . . ?
O2 C15 C7 125.3(2) . . ?
O1 C15 C7 110.54(17) . . ?
C17 C16 O1 106.4(4) . . ?
C17 C16 C18 113.9(4) . . ?
O1 C16 C18 105.7(4) . . ?
C17 C16 H16A 110.2 . . ?
O1 C16 H16A 110.2 . . ?
C18 C16 H16A 110.2 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C6 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 C14 178.8(3) . . . . ?
C3 C4 C5 O3 -179.8(2) . . . . ?
C14 C4 C5 O3 1.1(4) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C14 C4 C5 C6 -178.7(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 179.5(2) . . . . ?
O3 C5 C6 C1 179.95(19) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
O3 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C7 -179.7(2) . . . . ?
C1 C6 C7 C15 28.0(3) . . . . ?
C5 C6 C7 C15 -152.54(17) . . . . ?
C1 C6 C7 C8 -97.9(2) . . . . ?
C5 C6 C7 C8 81.6(2) . . . . ?
C6 C7 C8 C9 -123.0(2) . . . . ?
C15 C7 C8 C9 111.6(2) . . . . ?
C6 C7 C8 C13 56.7(3) . . . . ?
C15 C7 C8 C13 -68.6(3) . . . . ?
C13 C8 C9 C10 1.2(4) . . . . ?
C7 C8 C9 C10 -179.1(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
C11 C12 C13 C8 0.9(5) . . . . ?
C9 C8 C13 C12 -1.6(4) . . . . ?
C7 C8 C13 C12 178.6(2) . . . . ?
C16 O1 C15 O2 2.8(5) . . . . ?
C16 O1 C15 C7 -178.3(3) . . . . ?
C6 C7 C15 O2 -88.1(3) . . . . ?
C8 C7 C15 O2 38.6(3) . . . . ?
C6 C7 C15 O1 93.0(2) . . . . ?
C8 C7 C15 O1 -140.3(2) . . . . ?
C15 O1 C16 C17 99.7(4) . . . . ?
C15 O1 C16 C18 -138.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.026
