# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_12cm007
_database_code_depnum_ccdc_archive 'CCDC 1541525'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            12CM007
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 N'
_chemical_formula_sum            'C22 H28 N'
_chemical_formula_weight         306.45

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'
N N 0.0061 0.0033 '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                   5.899(2)
_cell_length_b                   7.547(3)
_cell_length_c                   20.535(8)
_cell_angle_alpha                83.465(9)
_cell_angle_beta                 84.681(10)
_cell_angle_gamma                82.512(8)
_cell_volume                     897.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2051
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      25.72

_exptl_crystal_description       'thin triangle-shaped layer'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_measurement_device_type  'Bruker APEX Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10626
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.72
_reflns_number_total             3361
_reflns_number_gt                2051
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'APEX2 2012.2 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v7.68A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT v7.68A (Bruker AXS Inc.)'
_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 > 2σ(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)+(0.0510P)²+0.1920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3361
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
C1 C 0.9442(4) 2.3006(3) 0.44759(12) 0.0489(7) Uani 1 1 d . . .
H1A H 1.0998 2.2390 0.4517 0.073 Uiso 1 1 calc R . .
H1B H 0.9012 2.3748 0.4840 0.073 Uiso 1 1 calc R . .
H1C H 0.9391 2.3773 0.4058 0.073 Uiso 1 1 calc R . .
H15 H 0.690(3) 0.885(2) 0.0686(9) 0.026(5) Uiso 1 1 d . . .
H16 H 0.637(3) 1.076(3) 0.1517(9) 0.025(5) Uiso 1 1 d . . .
H8B H 0.241(3) 1.454(3) 0.2899(10) 0.030(5) Uiso 1 1 d . . .
H8A H 0.398(3) 1.315(3) 0.3415(10) 0.034(6) Uiso 1 1 d . . .
H6A H 0.364(3) 1.710(3) 0.3424(9) 0.030(5) Uiso 1 1 d . . .
H6B H 0.524(4) 1.576(3) 0.3870(12) 0.044(7) Uiso 1 1 d . . .
H12 H 0.055(3) 0.876(3) 0.2254(10) 0.032(5) Uiso 1 1 d . . .
H13 H 0.113(3) 0.669(3) 0.1446(9) 0.027(5) Uiso 1 1 d . . .
H21 H 0.760(3) 0.544(2) 0.1390(9) 0.021(5) Uiso 1 1 d . . .
H23 H 1.156(3) 0.130(3) 0.0600(9) 0.025(5) Uiso 1 1 d . . .
H19 H 0.078(3) 0.851(3) 0.0261(10) 0.027(5) Uiso 1 1 d . . .
H22 H 1.081(3) 0.331(3) 0.1425(10) 0.028(6) Uiso 1 1 d . . .
H9 H 0.462(4) 1.315(3) 0.2034(11) 0.039(7) Uiso 1 1 d . . .
C17 C 0.4545(3) 0.6230(2) 0.04907(9) 0.0200(5) Uani 1 1 d . . .
C11 C 0.3420(3) 1.0000(2) 0.19659(9) 0.0217(5) Uani 1 1 d . . .
C20 C 0.6429(3) 0.4883(2) 0.05216(9) 0.0200(5) Uani 1 1 d . . .
C18 C 0.3102(3) 0.6358(2) -0.00283(9) 0.0200(5) Uani 1 1 d . . .
C7 C 0.5728(3) 1.5224(3) 0.28973(10) 0.0304(5) Uani 1 1 d . . .
H7A H 0.5678 1.5954 0.2465 0.036 Uiso 1 1 calc R . .
H7B H 0.7291 1.4572 0.2923 0.036 Uiso 1 1 calc R . .
N9 N 0.4597(3) 1.2591(2) 0.24484(9) 0.0296(5) Uani 1 1 d . . .
C5 C 0.6974(3) 1.7829(3) 0.34115(10) 0.0298(5) Uani 1 1 d . . .
H5A H 0.6892 1.8601 0.2989 0.036 Uiso 1 1 calc R . .
H5B H 0.8540 1.7174 0.3419 0.036 Uiso 1 1 calc R . .
C10 C 0.2965(3) 1.1283(2) 0.24925(10) 0.0267(5) Uani 1 1 d . . .
H10A H 0.1403 1.1933 0.2461 0.032 Uiso 1 1 calc R . .
H10B H 0.3003 1.0577 0.2929 0.032 Uiso 1 1 calc R . .
C4 C 0.6577(3) 1.9022(3) 0.39722(10) 0.0308(5) Uani 1 1 d . . .
H4A H 0.4996 1.9652 0.3971 0.037 Uiso 1 1 calc R . .
H4B H 0.6692 1.8249 0.4394 0.037 Uiso 1 1 calc R . .
C14 C 0.4121(3) 0.7544(2) 0.09994(9) 0.0202(4) Uani 1 1 d . . .
C6 C 0.5262(4) 1.6474(3) 0.34413(11) 0.0313(5) Uani 1 1 d . . .
C3 C 0.8237(4) 2.0413(3) 0.39418(11) 0.0329(5) Uani 1 1 d . . .
H3A H 0.8154 2.1171 0.3516 0.039 Uiso 1 1 calc R . .
H3B H 0.9817 1.9786 0.3957 0.039 Uiso 1 1 calc R . .
C13 C 0.2229(3) 0.7546(3) 0.14621(10) 0.0243(5) Uani 1 1 d . . .
C8 C 0.4018(4) 1.3870(3) 0.29404(11) 0.0312(5) Uani 1 1 d . . .
C22 C 0.9783(3) 0.3398(2) 0.10698(11) 0.0237(5) Uani 1 1 d . . .
C23 C 1.0261(3) 0.2203(3) 0.05759(10) 0.0234(5) Uani 1 1 d . . .
C12 C 0.1880(3) 0.8762(2) 0.19310(10) 0.0256(5) Uani 1 1 d . . .
C16 C 0.5297(3) 1.0002(2) 0.15061(10) 0.0237(5) Uani 1 1 d . . .
C21 C 0.7923(3) 0.4672(2) 0.10451(10) 0.0220(5) Uani 1 1 d . . .
C2 C 0.7767(4) 2.1619(3) 0.44958(11) 0.0366(6) Uani 1 1 d . . .
H2A H 0.7828 2.0858 0.4921 0.044 Uiso 1 1 calc R . .
H2B H 0.6194 2.2255 0.4476 0.044 Uiso 1 1 calc R . .
C15 C 0.5633(3) 0.8800(2) 0.10302(10) 0.0233(5) Uani 1 1 d . . .
C19 C 0.1144(3) 0.7695(2) -0.00843(10) 0.0215(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0579(16) 0.0411(14) 0.0526(16) -0.0123(12) -0.0095(13) -0.0140(12)
C17 0.0174(9) 0.0161(9) 0.0267(11) -0.0017(8) 0.0010(9) -0.0058(8)
C11 0.0216(10) 0.0179(10) 0.0253(11) -0.0018(8) -0.0040(9) 0.0001(8)
C20 0.0173(9) 0.0166(10) 0.0271(11) -0.0017(8) -0.0010(9) -0.0065(8)
C18 0.0168(9) 0.0153(9) 0.0285(11) -0.0008(8) -0.0002(9) -0.0061(7)
C7 0.0340(12) 0.0265(11) 0.0318(12) -0.0077(9) -0.0027(10) -0.0039(9)
N9 0.0346(10) 0.0265(10) 0.0300(11) -0.0107(8) 0.0003(9) -0.0075(8)
C5 0.0317(11) 0.0268(11) 0.0310(12) -0.0069(9) -0.0012(10) -0.0021(9)
C10 0.0264(10) 0.0241(11) 0.0292(12) -0.0041(9) -0.0014(9) -0.0017(9)
C4 0.0341(12) 0.0283(11) 0.0310(12) -0.0058(10) -0.0010(10) -0.0061(9)
C14 0.0191(9) 0.0164(9) 0.0253(11) -0.0016(8) -0.0047(8) -0.0013(8)
C6 0.0345(12) 0.0277(12) 0.0325(13) -0.0095(10) 0.0008(11) -0.0040(10)
C3 0.0359(12) 0.0302(12) 0.0335(12) -0.0060(10) -0.0015(10) -0.0064(10)
C13 0.0203(10) 0.0220(10) 0.0317(12) -0.0025(9) -0.0021(9) -0.0068(8)
C8 0.0346(13) 0.0269(12) 0.0333(13) -0.0110(10) -0.0003(11) -0.0034(10)
C22 0.0223(10) 0.0186(10) 0.0310(12) -0.0015(9) -0.0065(10) -0.0035(8)
C23 0.0177(10) 0.0172(10) 0.0348(12) 0.0000(9) -0.0044(9) -0.0012(8)
C12 0.0225(10) 0.0260(11) 0.0279(12) -0.0039(9) 0.0026(9) -0.0031(9)
C16 0.0183(10) 0.0181(10) 0.0363(12) -0.0042(9) -0.0040(9) -0.0051(8)
C21 0.0219(10) 0.0175(10) 0.0279(11) -0.0042(9) -0.0013(9) -0.0055(8)
C2 0.0451(13) 0.0313(12) 0.0359(13) -0.0095(10) -0.0049(11) -0.0071(10)
C15 0.0197(10) 0.0202(10) 0.0302(12) -0.0053(9) 0.0014(9) -0.0036(8)
C19 0.0182(10) 0.0147(10) 0.0318(12) -0.0030(9) -0.0001(9) -0.0029(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.525(3) . ?
C17 C20 1.406(2) . ?
C17 C18 1.412(3) . ?
C17 C14 1.503(2) . ?
C11 C16 1.387(2) . ?
C11 C12 1.397(3) . ?
C11 C10 1.515(2) . ?
C20 C21 1.434(3) . ?
C20 C18 1.441(2) 2_665 ?
C18 C19 1.436(3) . ?
C18 C20 1.441(2) 2_665 ?
C7 C8 1.517(3) . ?
C7 C6 1.526(3) . ?
N9 C10 1.456(2) . ?
N9 C8 1.464(2) . ?
C5 C6 1.521(3) . ?
C5 C4 1.524(3) . ?
C4 C3 1.519(3) . ?
C14 C15 1.393(3) . ?
C14 C13 1.397(2) . ?
C3 C2 1.520(3) . ?
C13 C12 1.388(3) . ?
C22 C21 1.362(3) . ?
C22 C23 1.418(3) . ?
C23 C19 1.354(3) 2_665 ?
C16 C15 1.392(3) . ?
C19 C23 1.354(3) 2_665 ?

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
C20 C17 C18 119.44(16) . . ?
C20 C17 C14 119.81(18) . . ?
C18 C17 C14 120.74(17) . . ?
C16 C11 C12 117.73(16) . . ?
C16 C11 C10 123.08(16) . . ?
C12 C11 C10 119.19(15) . . ?
C17 C20 C21 121.71(16) . . ?
C17 C20 C18 120.57(18) . 2_665 ?
C21 C20 C18 117.72(17) . 2_665 ?
C17 C18 C19 122.06(16) . . ?
C17 C18 C20 120.00(17) . 2_665 ?
C19 C18 C20 117.94(19) . 2_665 ?
C8 C7 C6 112.95(16) . . ?
C10 N9 C8 112.25(15) . . ?
C6 C5 C4 113.88(16) . . ?
N9 C10 C11 113.97(14) . . ?
C3 C4 C5 114.61(16) . . ?
C15 C14 C13 117.43(16) . . ?
C15 C14 C17 120.77(15) . . ?
C13 C14 C17 121.79(16) . . ?
C5 C6 C7 113.80(16) . . ?
C4 C3 C2 113.62(16) . . ?
C12 C13 C14 120.83(17) . . ?
N9 C8 C7 112.21(16) . . ?
C21 C22 C23 120.0(2) . . ?
C19 C23 C22 120.24(19) 2_665 . ?
C13 C12 C11 121.49(16) . . ?
C11 C16 C15 120.83(17) . . ?
C22 C21 C20 122.03(18) . . ?
C3 C2 C1 114.15(17) . . ?
C16 C15 C14 121.66(16) . . ?
C23 C19 C18 122.03(18) 2_665 . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.72
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_12cm104
_database_code_depnum_ccdc_archive 'CCDC 1541528'
loop_
_audit_author_name
_audit_author_address
'Aline Lacoudre'
;ISM Universit? de Bordeaux 
France
;
_audit_update_record             
;
2017-03-31 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            12CM104
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 O2'
_chemical_formula_sum            'C28 H18 O2'
_chemical_formula_weight         386.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   13.0175(5)
_cell_length_b                   9.3290(3)
_cell_length_c                   8.3512(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.370(2)
_cell_angle_gamma                90.00
_cell_volume                     973.06(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1503
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      65.86

_exptl_crystal_description       'no information'
_exptl_crystal_colour            'no information'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8873
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_measurement_device_type  'Bruker APEX Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10846
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         65.86
_reflns_number_total             1662
_reflns_number_gt                1503
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'APEX2 2012.2 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v7.68A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT v7.68A (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ORTEP

_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 > 2σ(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)+(0.0529P)²+0.2180P] 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         1662
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
H2 H -0.0357 0.1262 0.1969 0.050 Uiso 1 1 d . . .
C10 C 0.49748(9) 0.06110(12) 0.15393(14) 0.0289(3) Uani 1 1 d . . .
C9 C 0.40146(9) 0.04058(12) 0.02777(15) 0.0290(3) Uani 1 1 d . . .
C6 C 0.29684(9) 0.08254(12) 0.05665(14) 0.0295(3) Uani 1 1 d . . .
C15 C 0.59792(9) 0.02045(12) 0.12586(14) 0.0288(3) Uani 1 1 d . . .
C12 C 0.59353(10) 0.14266(13) 0.43292(16) 0.0350(3) Uani 1 1 d . . .
H12 H 0.5928 0.1819 0.5375 0.042 Uiso 1 1 calc R . .
O1 O -0.04488(8) 0.31493(14) 0.10099(14) 0.0593(3) Uani 1 1 d . . .
C11 C 0.49996(10) 0.12256(13) 0.31201(15) 0.0327(3) Uani 1 1 d . . .
H11 H 0.4346 0.1499 0.3329 0.039 Uiso 1 1 calc R . .
C14 C 0.69423(9) 0.04658(13) 0.25571(15) 0.0322(3) Uani 1 1 d . . .
H14 H 0.7611 0.0223 0.2381 0.039 Uiso 1 1 calc R . .
C13 C 0.69238(10) 0.10535(13) 0.40387(16) 0.0353(3) Uani 1 1 d . . .
H13 H 0.7576 0.1215 0.4883 0.042 Uiso 1 1 calc R . .
C5 C 0.25360(10) 0.21816(13) 0.01064(16) 0.0353(3) Uani 1 1 d . . .
H5 H 0.2909 0.2846 -0.0388 0.042 Uiso 1 1 calc R . .
C8 C 0.14469(10) 0.02546(14) 0.15578(16) 0.0358(3) Uani 1 1 d . . .
H8 H 0.1076 -0.0405 0.2061 0.043 Uiso 1 1 calc R . .
C7 C 0.24166(10) -0.01329(13) 0.12988(15) 0.0330(3) Uani 1 1 d . . .
H7 H 0.2706 -0.1058 0.1623 0.040 Uiso 1 1 calc R . .
C3 C 0.10174(10) 0.16052(14) 0.10830(15) 0.0348(3) Uani 1 1 d . . .
C2 C -0.00087(11) 0.20082(17) 0.13905(17) 0.0453(4) Uani 1 1 d . . .
C4 C 0.15674(10) 0.25697(14) 0.03638(16) 0.0360(3) Uani 1 1 d . . .
H4 H 0.1280 0.3497 0.0048 0.043 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C10 0.0318(6) 0.0239(5) 0.0343(6) 0.0017(5) 0.0150(5) -0.0003(4)
C9 0.0303(6) 0.0246(6) 0.0354(6) 0.0029(5) 0.0147(5) 0.0006(4)
C6 0.0283(6) 0.0320(6) 0.0299(6) -0.0028(5) 0.0107(5) -0.0002(5)
C15 0.0304(6) 0.0245(6) 0.0340(6) 0.0024(4) 0.0133(5) -0.0001(4)
C12 0.0409(7) 0.0321(6) 0.0342(6) -0.0053(5) 0.0140(5) -0.0017(5)
O1 0.0377(6) 0.0745(8) 0.0657(7) -0.0147(6) 0.0148(5) 0.0160(5)
C11 0.0338(6) 0.0304(6) 0.0379(6) -0.0022(5) 0.0167(5) 0.0008(5)
C14 0.0296(6) 0.0311(6) 0.0382(6) 0.0017(5) 0.0132(5) 0.0007(5)
C13 0.0347(6) 0.0328(6) 0.0373(7) -0.0014(5) 0.0083(5) -0.0024(5)
C5 0.0353(6) 0.0341(6) 0.0408(7) 0.0028(5) 0.0175(5) 0.0018(5)
C8 0.0330(6) 0.0415(7) 0.0365(6) -0.0038(5) 0.0155(5) -0.0070(5)
C7 0.0337(6) 0.0313(6) 0.0365(6) -0.0002(5) 0.0138(5) -0.0005(5)
C3 0.0280(6) 0.0458(7) 0.0311(6) -0.0089(5) 0.0090(5) -0.0002(5)
C2 0.0316(7) 0.0627(9) 0.0423(7) -0.0151(7) 0.0113(6) 0.0009(6)
C4 0.0343(6) 0.0375(7) 0.0368(6) -0.0004(5) 0.0108(5) 0.0076(5)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C10 C9 1.4025(17) . ?
C10 C11 1.4313(17) . ?
C10 C15 1.4424(16) . ?
C9 C15 1.4058(17) 3_655 ?
C9 C6 1.5004(15) . ?
C6 C7 1.3917(17) . ?
C6 C5 1.3941(18) . ?
C15 C9 1.4058(17) 3_655 ?
C15 C14 1.4286(17) . ?
C12 C11 1.3584(18) . ?
C12 C13 1.4184(17) . ?
O1 C2 1.208(2) . ?
C14 C13 1.3597(18) . ?
C5 C4 1.3857(17) . ?
C8 C7 1.3873(17) . ?
C8 C3 1.3901(19) . ?
C3 C4 1.3875(19) . ?
C3 C2 1.4782(17) . ?

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
C9 C10 C11 122.08(10) . . ?
C9 C10 C15 119.92(11) . . ?
C11 C10 C15 117.99(11) . . ?
C10 C9 C15 120.51(10) . 3_655 ?
C10 C9 C6 120.06(10) . . ?
C15 C9 C6 119.43(10) 3_655 . ?
C7 C6 C5 119.07(11) . . ?
C7 C6 C9 120.49(10) . . ?
C5 C6 C9 120.45(10) . . ?
C9 C15 C14 122.16(10) 3_655 . ?
C9 C15 C10 119.57(11) 3_655 . ?
C14 C15 C10 118.27(10) . . ?
C11 C12 C13 120.38(11) . . ?
C12 C11 C10 121.55(11) . . ?
C13 C14 C15 121.51(11) . . ?
C14 C13 C12 120.28(11) . . ?
C4 C5 C6 120.58(11) . . ?
C7 C8 C3 120.14(11) . . ?
C8 C7 C6 120.41(11) . . ?
C4 C3 C8 119.75(11) . . ?
C4 C3 C2 120.79(12) . . ?
C8 C3 C2 119.44(12) . . ?
O1 C2 C3 124.27(14) . . ?
C5 C4 C3 120.05(12) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        65.86
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035
