# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1047277'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-12-(2,2-Dimethylpropylidene)-2-methyl-5,6,7,12-tetrahydro-dibenzo[a,d]cyclooctene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26'
_chemical_formula_weight         290.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.4844(7)
_cell_length_b                   8.0920(5)
_cell_length_c                   17.7356(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.4990(10)
_cell_angle_gamma                90
_cell_volume                     1790.01(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cube
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19322
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         28.440
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4277
_reflns_number_gt                3403
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0880P)²+0.4207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4277
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1678
_refine_ls_wR_factor_gt          0.1539
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.19837(11) 0.30433(16) 0.01034(7) 0.0418(3) Uani 1 1 d . . . . .
H1 H 0.1254 0.2928 0.0176 0.050 Uiso 1 1 calc R U . . .
C2 C 0.23088(9) 0.15297(15) 0.13181(7) 0.0372(3) Uani 1 1 d . . . . .
C3 C 0.27148(10) 0.23663(14) 0.06332(7) 0.0377(3) Uani 1 1 d . . . . .
C4 C 0.21011(11) 0.27106(16) 0.19497(7) 0.0406(3) Uani 1 1 d . . . . .
C5 C 0.38176(11) 0.25540(16) 0.05439(8) 0.0436(3) Uani 1 1 d . . . . .
C6 C 0.29166(12) 0.31776(18) 0.24768(8) 0.0484(3) Uani 1 1 d . . . . .
C7 C 0.41375(12) 0.3372(2) -0.01010(8) 0.0541(4) Uani 1 1 d . . . . .
H2 H 0.4865 0.3475 -0.0182 0.065 Uiso 1 1 calc R U . . .
C8 C 0.23115(13) 0.38873(17) -0.05314(7) 0.0496(3) Uani 1 1 d . . . . .
C9 C 0.10813(12) 0.33878(19) 0.19968(8) 0.0510(3) Uani 1 1 d . . . . .
H3 H 0.0542 0.3074 0.1648 0.061 Uiso 1 1 calc R U . . .
C10 C 0.34055(14) 0.40332(19) -0.06219(8) 0.0572(4) Uani 1 1 d . . . . .
H4 H 0.3649 0.4586 -0.1041 0.069 Uiso 1 1 calc R U . . .
C11 C 0.46478(11) 0.1916(2) 0.11165(9) 0.0566(4) Uani 1 1 d . . . . .
H5 H 0.5337 0.1900 0.0884 0.068 Uiso 1 1 calc R U . . .
H6 H 0.4469 0.0784 0.1239 0.068 Uiso 1 1 calc R U . . .
C12 C 0.21041(10) -0.00754(16) 0.13977(7) 0.0433(3) Uani 1 1 d . . . . .
H7 H 0.1852 -0.0345 0.1868 0.052 Uiso 1 1 calc R U . . .
C13 C 0.21982(12) -0.15521(17) 0.08779(8) 0.0505(3) Uani 1 1 d . . . . .
C14 C 0.08534(15) 0.4522(2) 0.25546(9) 0.0651(4) Uani 1 1 d . . . . .
H8 H 0.0167 0.4959 0.2580 0.078 Uiso 1 1 calc R U . . .
C15 C 0.26649(15) 0.4320(2) 0.30312(9) 0.0629(4) Uani 1 1 d . . . . .
H9 H 0.3195 0.4638 0.3387 0.075 Uiso 1 1 calc R U . . .
C16 C 0.40208(13) 0.2414(2) 0.24855(9) 0.0604(4) Uani 1 1 d . . . . .
H10 H 0.3934 0.1223 0.2471 0.073 Uiso 1 1 calc R U . . .
H11 H 0.4383 0.2686 0.2965 0.073 Uiso 1 1 calc R U . . .
C17 C 0.15104(16) 0.4592(2) -0.11020(9) 0.0697(5) Uani 1 1 d . . . . .
H12 H 0.1831 0.5493 -0.1363 0.105 Uiso 1 1 calc R U . . .
H13 H 0.0895 0.4983 -0.0849 0.105 Uiso 1 1 calc R U . . .
H14 H 0.1294 0.3750 -0.1458 0.105 Uiso 1 1 calc R U . . .
C18 C 0.47665(13) 0.2901(2) 0.18545(10) 0.0633(4) Uani 1 1 d . . . . .
H15 H 0.4647 0.4059 0.1738 0.076 Uiso 1 1 calc R U . . .
H16 H 0.5501 0.2792 0.2049 0.076 Uiso 1 1 calc R U . . .
C19 C 0.16487(17) 0.4992(2) 0.30669(9) 0.0700(5) Uani 1 1 d . . . . .
H17 H 0.1506 0.5762 0.3439 0.084 Uiso 1 1 calc R U . . .
C20 C 0.26464(19) -0.1188(2) 0.01109(10) 0.0760(6) Uani 1 1 d . . . . .
H18 H 0.2172 -0.0450 -0.0165 0.114 Uiso 1 1 calc R U . . .
H19 H 0.2710 -0.2200 -0.0166 0.114 Uiso 1 1 calc R U . . .
H20 H 0.3340 -0.0684 0.0180 0.114 Uiso 1 1 calc R U . . .
C21 C 0.2943(2) -0.2825(2) 0.12732(12) 0.0825(6) Uani 1 1 d . . . . .
H21 H 0.3652 -0.2371 0.1338 0.124 Uiso 1 1 calc R U . . .
H22 H 0.2967 -0.3808 0.0971 0.124 Uiso 1 1 calc R U . . .
H23 H 0.2677 -0.3093 0.1758 0.124 Uiso 1 1 calc R U . . .
C22 C 0.10875(18) -0.2317(3) 0.07772(16) 0.0977(8) Uani 1 1 d . . . . .
H24 H 0.0796 -0.2492 0.1263 0.147 Uiso 1 1 calc R U . . .
H25 H 0.1138 -0.3355 0.0520 0.147 Uiso 1 1 calc R U . . .
H26 H 0.0627 -0.1586 0.0486 0.147 Uiso 1 1 calc R U . . .


_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
C1 C3 1.3932(18) . ?
C1 C8 1.3933(18) . ?
C2 C12 1.3325(18) . ?
C2 C3 1.4982(16) . ?
C2 C4 1.5035(17) . ?
C3 C5 1.4010(17) . ?
C4 C9 1.3919(19) . ?
C4 C6 1.4036(19) . ?
C5 C7 1.3950(19) . ?
C5 C11 1.510(2) . ?
C6 C15 1.395(2) . ?
C6 C16 1.510(2) . ?
C7 C10 1.379(2) . ?
C8 C10 1.387(2) . ?
C8 C17 1.504(2) . ?
C9 C14 1.388(2) . ?
C11 C18 1.534(2) . ?
C12 C13 1.5170(19) . ?
C13 C22 1.522(2) . ?
C13 C20 1.522(2) . ?
C13 C21 1.537(2) . ?
C14 C19 1.370(3) . ?
C15 C19 1.384(3) . ?
C16 C18 1.538(2) . ?

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
C3 C1 C8 122.06(13) . . ?
C12 C2 C3 126.84(11) . . ?
C12 C2 C4 120.03(11) . . ?
C3 C2 C4 113.10(10) . . ?
C1 C3 C5 119.95(12) . . ?
C1 C3 C2 119.32(11) . . ?
C5 C3 C2 120.63(11) . . ?
C9 C4 C6 119.53(13) . . ?
C9 C4 C2 118.87(12) . . ?
C6 C4 C2 121.57(12) . . ?
C7 C5 C3 117.51(13) . . ?
C7 C5 C11 120.07(13) . . ?
C3 C5 C11 122.42(12) . . ?
C15 C6 C4 117.94(14) . . ?
C15 C6 C16 119.83(14) . . ?
C4 C6 C16 122.14(13) . . ?
C10 C7 C5 121.90(14) . . ?
C10 C8 C1 117.42(13) . . ?
C10 C8 C17 121.27(14) . . ?
C1 C8 C17 121.30(14) . . ?
C14 C9 C4 121.30(15) . . ?
C7 C10 C8 121.11(13) . . ?
C5 C11 C18 115.74(13) . . ?
C2 C12 C13 133.09(12) . . ?
C12 C13 C22 107.29(13) . . ?
C12 C13 C20 115.59(12) . . ?
C22 C13 C20 110.03(17) . . ?
C12 C13 C21 108.19(13) . . ?
C22 C13 C21 108.13(16) . . ?
C20 C13 C21 107.39(15) . . ?
C19 C14 C9 119.40(16) . . ?
C19 C15 C6 121.83(15) . . ?
C6 C16 C18 117.96(14) . . ?
C11 C18 C16 116.67(14) . . ?
C14 C19 C15 119.99(15) . . ?

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
C8 C1 C3 C5 1.31(19) . . . . ?
C8 C1 C3 C2 177.70(11) . . . . ?
C12 C2 C3 C1 93.13(16) . . . . ?
C4 C2 C3 C1 -85.08(14) . . . . ?
C12 C2 C3 C5 -90.51(16) . . . . ?
C4 C2 C3 C5 91.28(14) . . . . ?
C12 C2 C4 C9 -86.64(16) . . . . ?
C3 C2 C4 C9 91.70(14) . . . . ?
C12 C2 C4 C6 95.20(16) . . . . ?
C3 C2 C4 C6 -86.46(14) . . . . ?
C1 C3 C5 C7 -2.49(19) . . . . ?
C2 C3 C5 C7 -178.83(12) . . . . ?
C1 C3 C5 C11 177.17(12) . . . . ?
C2 C3 C5 C11 0.83(19) . . . . ?
C9 C4 C6 C15 -0.1(2) . . . . ?
C2 C4 C6 C15 178.00(13) . . . . ?
C9 C4 C6 C16 176.27(13) . . . . ?
C2 C4 C6 C16 -5.6(2) . . . . ?
C3 C5 C7 C10 2.4(2) . . . . ?
C11 C5 C7 C10 -177.28(14) . . . . ?
C3 C1 C8 C10 0.1(2) . . . . ?
C3 C1 C8 C17 179.25(13) . . . . ?
C6 C4 C9 C14 0.2(2) . . . . ?
C2 C4 C9 C14 -178.04(14) . . . . ?
C5 C7 C10 C8 -1.0(2) . . . . ?
C1 C8 C10 C7 -0.2(2) . . . . ?
C17 C8 C10 C7 -179.40(15) . . . . ?
C7 C5 C11 C18 106.01(16) . . . . ?
C3 C5 C11 C18 -73.64(18) . . . . ?
C3 C2 C12 C13 0.4(2) . . . . ?
C4 C2 C12 C13 178.50(13) . . . . ?
C2 C12 C13 C22 -120.98(19) . . . . ?
C2 C12 C13 C20 2.2(2) . . . . ?
C2 C12 C13 C21 122.58(18) . . . . ?
C4 C9 C14 C19 0.3(2) . . . . ?
C4 C6 C15 C19 -0.4(2) . . . . ?
C16 C6 C15 C19 -176.86(16) . . . . ?
C15 C6 C16 C18 -110.79(17) . . . . ?
C4 C6 C16 C18 72.9(2) . . . . ?
C5 C11 C18 C16 87.33(19) . . . . ?
C6 C16 C18 C11 -85.6(2) . . . . ?
C9 C14 C19 C15 -0.8(3) . . . . ?
C6 C15 C19 C14 0.9(3) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1047278'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-5-(2,2-Dimethylpropylidene)-10,11-dihydro-3-methyl-5H-dibenzo[a,d]cycloheptene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24'
_chemical_formula_weight         276.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   5.881(5)
_cell_length_b                   16.344(13)
_cell_length_c                   17.969(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.555(10)
_cell_angle_gamma                90
_cell_volume                     1719(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9235
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.278
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3933
_reflns_number_gt                2384
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0949P)²+0.1917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3933
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1667
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.133
_refine_ls_shift/su_mean         0.003

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9814(3) 0.11990(10) 0.15865(10) 0.0496(5) Uani 1 1 d . . . . .
H1 H 1.0516 0.0865 0.1960 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8043(3) 0.17160(10) 0.17676(10) 0.0472(5) Uani 1 1 d . . . . .
C3 C 0.7398(3) 0.17015(10) 0.25629(10) 0.0443(4) Uani 1 1 d . . . . .
C4 C 0.6967(4) 0.22301(11) 0.12070(11) 0.0546(5) Uani 1 1 d . . . . .
C5 C 0.9110(3) 0.27762(11) 0.34626(10) 0.0506(5) Uani 1 1 d . . . . .
H2 H 1.0281 0.2414 0.3618 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6984(3) 0.09790(11) 0.28773(10) 0.0496(5) Uani 1 1 d . . . . .
H3 H 0.7176 0.0534 0.2567 0.059 Uiso 1 1 calc R U . . .
C7 C 0.7378(3) 0.25297(10) 0.29251(10) 0.0444(4) Uani 1 1 d . . . . .
C8 C 0.5636(3) 0.30850(11) 0.26764(11) 0.0491(5) Uani 1 1 d . . . . .
C9 C 0.6263(3) 0.07403(11) 0.36402(11) 0.0528(5) Uani 1 1 d . . . . .
C10 C 1.0574(4) 0.11605(12) 0.08765(11) 0.0573(5) Uani 1 1 d . . . . .
C11 C 0.5650(4) 0.38604(11) 0.30011(12) 0.0579(5) Uani 1 1 d . . . . .
H4 H 0.4481 0.4226 0.2852 0.069 Uiso 1 1 calc R U . . .
C12 C 0.3916(3) 0.28298(13) 0.20424(13) 0.0622(6) Uani 1 1 d . . . . .
H23 H 0.2642 0.3209 0.2007 0.075 Uiso 1 1 calc R U . . .
H24 H 0.3333 0.2291 0.2146 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7360(4) 0.40979(12) 0.35391(12) 0.0613(6) Uani 1 1 d . . . . .
H6 H 0.7339 0.4619 0.3746 0.074 Uiso 1 1 calc R U . . .
C14 C 0.9107(4) 0.35592(12) 0.37692(11) 0.0588(5) Uani 1 1 d . . . . .
H7 H 1.0272 0.3719 0.4127 0.071 Uiso 1 1 calc R U . . .
C15 C 0.7782(4) 0.21850(14) 0.04960(12) 0.0686(6) Uani 1 1 d . . . . .
H8 H 0.7116 0.2522 0.0119 0.082 Uiso 1 1 calc R U . . .
C16 C 0.4968(4) 0.28110(13) 0.12942(12) 0.0665(6) Uani 1 1 d . . . . .
H25 H 0.3759 0.2676 0.0908 0.080 Uiso 1 1 calc R U . . .
H26 H 0.5475 0.3361 0.1193 0.080 Uiso 1 1 calc R U . . .
C17 C 0.9506(4) 0.16700(14) 0.03313(12) 0.0692(6) Uani 1 1 d . . . . .
H10 H 0.9963 0.1662 -0.0150 0.083 Uiso 1 1 calc R U . . .
C18 C 1.2507(4) 0.05873(15) 0.07254(14) 0.0771(7) Uani 1 1 d . . . . .
H11 H 1.3227 0.0383 0.1191 0.116 Uiso 1 1 calc R U . . .
H12 H 1.3610 0.0878 0.0467 0.116 Uiso 1 1 calc R U . . .
H13 H 1.1908 0.0138 0.0423 0.116 Uiso 1 1 calc R U . . .
C19 C 0.4725(6) -0.00206(19) 0.35214(17) 0.1100(11) Uani 1 1 d . . . . .
H14 H 0.3384 0.0116 0.3198 0.165 Uiso 1 1 calc R U . . .
H15 H 0.4286 -0.0204 0.3995 0.165 Uiso 1 1 calc R U . . .
H16 H 0.5547 -0.0448 0.3298 0.165 Uiso 1 1 calc R U . . .
C20 C 0.8342(5) 0.0482(3) 0.41460(17) 0.1225(13) Uani 1 1 d . . . . .
H17 H 0.9178 0.0077 0.3897 0.184 Uiso 1 1 calc R U . . .
H18 H 0.7868 0.0256 0.4599 0.184 Uiso 1 1 calc R U . . .
H19 H 0.9301 0.0949 0.4263 0.184 Uiso 1 1 calc R U . . .
C21 C 0.4929(6) 0.13901(18) 0.40106(19) 0.1208(14) Uani 1 1 d . . . . .
H20 H 0.5901 0.1851 0.4137 0.181 Uiso 1 1 calc R U . . .
H21 H 0.4386 0.1171 0.4456 0.181 Uiso 1 1 calc R U . . .
H22 H 0.3652 0.1561 0.3673 0.181 Uiso 1 1 calc R U . . .


_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
C1 C10 1.393(3) . ?
C1 C2 1.404(3) . ?
C2 C4 1.413(3) . ?
C2 C3 1.514(3) . ?
C3 C6 1.341(3) . ?
C3 C7 1.503(3) . ?
C4 C15 1.409(3) . ?
C4 C16 1.531(3) . ?
C5 C7 1.394(3) . ?
C5 C14 1.393(3) . ?
C6 C9 1.524(3) . ?
C7 C8 1.409(3) . ?
C8 C11 1.395(3) . ?
C8 C12 1.507(3) . ?
C9 C20 1.511(3) . ?
C9 C21 1.513(3) . ?
C9 C19 1.540(3) . ?
C10 C17 1.389(3) . ?
C10 C18 1.518(3) . ?
C11 C13 1.382(3) . ?
C12 C16 1.533(3) . ?
C13 C14 1.385(3) . ?
C15 C17 1.372(3) . ?

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
C10 C1 C2 123.40(18) . . ?
C1 C2 C4 118.92(18) . . ?
C1 C2 C3 117.95(16) . . ?
C4 C2 C3 123.13(18) . . ?
C6 C3 C7 126.96(17) . . ?
C6 C3 C2 118.93(16) . . ?
C7 C3 C2 114.08(14) . . ?
C15 C4 C2 116.6(2) . . ?
C15 C4 C16 117.21(18) . . ?
C2 C4 C16 126.22(19) . . ?
C7 C5 C14 120.72(17) . . ?
C3 C6 C9 132.97(17) . . ?
C5 C7 C8 119.59(17) . . ?
C5 C7 C3 121.66(16) . . ?
C8 C7 C3 118.62(17) . . ?
C11 C8 C7 118.55(18) . . ?
C11 C8 C12 122.96(17) . . ?
C7 C8 C12 118.40(17) . . ?
C20 C9 C21 110.8(3) . . ?
C20 C9 C6 109.46(17) . . ?
C21 C9 C6 114.67(18) . . ?
C20 C9 C19 106.7(2) . . ?
C21 C9 C19 107.8(2) . . ?
C6 C9 C19 107.02(18) . . ?
C17 C10 C1 117.1(2) . . ?
C17 C10 C18 122.7(2) . . ?
C1 C10 C18 120.27(19) . . ?
C13 C11 C8 121.49(18) . . ?
C8 C12 C16 111.74(18) . . ?
C11 C13 C14 119.93(19) . . ?
C13 C14 C5 119.66(19) . . ?
C17 C15 C4 123.4(2) . . ?
C4 C16 C12 118.75(17) . . ?
C15 C17 C10 120.6(2) . . ?

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
C10 C1 C2 C4 -0.3(3) . . . . ?
C10 C1 C2 C3 -179.55(16) . . . . ?
C1 C2 C3 C6 -50.7(2) . . . . ?
C4 C2 C3 C6 130.1(2) . . . . ?
C1 C2 C3 C7 127.30(17) . . . . ?
C4 C2 C3 C7 -51.9(2) . . . . ?
C1 C2 C4 C15 -0.3(3) . . . . ?
C3 C2 C4 C15 178.91(17) . . . . ?
C1 C2 C4 C16 177.95(17) . . . . ?
C3 C2 C4 C16 -2.8(3) . . . . ?
C7 C3 C6 C9 3.8(3) . . . . ?
C2 C3 C6 C9 -178.50(19) . . . . ?
C14 C5 C7 C8 1.5(3) . . . . ?
C14 C5 C7 C3 177.36(18) . . . . ?
C6 C3 C7 C5 72.7(3) . . . . ?
C2 C3 C7 C5 -105.1(2) . . . . ?
C6 C3 C7 C8 -111.5(2) . . . . ?
C2 C3 C7 C8 70.8(2) . . . . ?
C5 C7 C8 C11 -2.6(3) . . . . ?
C3 C7 C8 C11 -178.52(17) . . . . ?
C5 C7 C8 C12 174.13(17) . . . . ?
C3 C7 C8 C12 -1.8(3) . . . . ?
C3 C6 C9 C20 -98.6(3) . . . . ?
C3 C6 C9 C21 26.7(3) . . . . ?
C3 C6 C9 C19 146.1(2) . . . . ?
C2 C1 C10 C17 0.4(3) . . . . ?
C2 C1 C10 C18 179.76(18) . . . . ?
C7 C8 C11 C13 2.0(3) . . . . ?
C12 C8 C11 C13 -174.57(19) . . . . ?
C11 C8 C12 C16 104.6(2) . . . . ?
C7 C8 C12 C16 -71.9(2) . . . . ?
C8 C11 C13 C14 -0.3(3) . . . . ?
C11 C13 C14 C5 -0.8(3) . . . . ?
C7 C5 C14 C13 0.2(3) . . . . ?
C2 C4 C15 C17 0.8(3) . . . . ?
C16 C4 C15 C17 -177.6(2) . . . . ?
C15 C4 C16 C12 175.50(18) . . . . ?
C2 C4 C16 C12 -2.8(3) . . . . ?
C8 C12 C16 C4 61.0(2) . . . . ?
C4 C15 C17 C10 -0.7(3) . . . . ?
C1 C10 C17 C15 0.1(3) . . . . ?
C18 C10 C17 C15 -179.3(2) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
