# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37

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                   11.2047(16)
_cell_length_b                   12.2098(18)
_cell_length_c                   13.3534(17)
_cell_angle_alpha                97.661(10)
_cell_angle_beta                 96.853(8)
_cell_angle_gamma                99.139(9)
_cell_volume                     1769.0(4)
_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       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13002
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6234
_reflns_number_gt                4601
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1298P)²+0.3489P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6234
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2170
_refine_ls_wR_factor_gt          0.2013
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.34909(14) -0.00874(13) 0.28761(12) 0.0547(4) Uani 1 1 d . . .
O2 O 0.43498(17) 0.02905(14) 0.10930(13) 0.0698(5) Uani 1 1 d . . .
H2A H 0.4869 0.0474 0.0734 0.105 Uiso 1 1 calc R . .
O3 O 0.38845(19) -0.11790(15) -0.01480(14) 0.0785(6) Uani 1 1 d . . .
C7 C 0.2771(2) -0.09815(19) 0.22520(18) 0.0519(5) Uani 1 1 d . . .
C9 C 0.3172(2) -0.0026(2) 0.38618(18) 0.0568(6) Uani 1 1 d . . .
C12 C 0.6439(2) 0.3718(2) 0.46750(19) 0.0583(6) Uani 1 1 d . . .
C13 C 0.3753(2) 0.0770(2) 0.46107(19) 0.0624(6) Uani 1 1 d . . .
H13A H 0.3514 0.0709 0.5247 0.075 Uiso 1 1 calc R . .
C16 C 0.3754(2) -0.0674(2) 0.07207(18) 0.0566(6) Uani 1 1 d . . .
C21 C 0.4706(2) 0.1724(2) 0.45956(18) 0.0563(6) Uani 1 1 d . . .
C22 C 0.2153(2) -0.0945(2) 0.38233(19) 0.0606(6) Uani 1 1 d . . .
C23 C 0.1911(2) -0.1530(2) 0.28456(19) 0.0570(6) Uani 1 1 d . . .
C25 C 0.2890(2) -0.1261(2) 0.12694(19) 0.0576(6) Uani 1 1 d . . .
H25A H 0.2366 -0.1894 0.0907 0.069 Uiso 1 1 calc R . .
C26 C 0.7311(2) 0.4826(2) 0.4707(2) 0.0669(7) Uani 1 1 d . . .
C29 C 0.5043(3) 0.2103(2) 0.3717(2) 0.0757(8) Uani 1 1 d . . .
H29A H 0.4697 0.1695 0.3082 0.091 Uiso 1 1 calc R . .
C32 C 0.5304(3) 0.2350(2) 0.55031(19) 0.0735(8) Uani 1 1 d . . .
H32A H 0.5130 0.2114 0.6112 0.088 Uiso 1 1 calc R . .
C33 C 0.5882(3) 0.3075(2) 0.37701(19) 0.0760(8) Uani 1 1 d . . .
H33A H 0.6079 0.3304 0.3164 0.091 Uiso 1 1 calc R . .
C34 C 0.6148(3) 0.3308(2) 0.5541(2) 0.0755(8) Uani 1 1 d . . .
H34A H 0.6534 0.3693 0.6174 0.091 Uiso 1 1 calc R . .
C37 C 0.0957(3) -0.2430(2) 0.2554(2) 0.0757(8) Uani 1 1 d . . .
H37A H 0.0803 -0.2816 0.1890 0.091 Uiso 1 1 calc R . .
C40 C 0.0488(4) -0.2141(3) 0.4260(3) 0.1048(12) Uani 1 1 d . . .
H40A H -0.0008 -0.2356 0.4736 0.126 Uiso 1 1 calc R . .
C41 C 0.1433(3) -0.1255(3) 0.4552(2) 0.0872(9) Uani 1 1 d . . .
H41A H 0.1588 -0.0871 0.5217 0.105 Uiso 1 1 calc R . .
C42 C 0.0248(3) -0.2732(3) 0.3269(3) 0.0996(11) Uani 1 1 d . . .
H42A H -0.0398 -0.3335 0.3094 0.119 Uiso 1 1 calc R . .
C43 C 0.8406(5) 0.4602(4) 0.4248(7) 0.242(5) Uani 1 1 d . . .
H43A H 0.8163 0.4247 0.3551 0.363 Uiso 1 1 calc R . .
H43B H 0.8811 0.4116 0.4624 0.363 Uiso 1 1 calc R . .
H43C H 0.8953 0.5297 0.4270 0.363 Uiso 1 1 calc R . .
C45 C 0.7712(9) 0.5418(6) 0.5716(4) 0.322(7) Uani 1 1 d . . .
H45A H 0.7016 0.5505 0.6055 0.484 Uiso 1 1 calc R . .
H45B H 0.8168 0.6145 0.5684 0.484 Uiso 1 1 calc R . .
H45C H 0.8222 0.5003 0.6089 0.484 Uiso 1 1 calc R . .
C47 C 0.6770(6) 0.5562(4) 0.4072(6) 0.225(4) Uani 1 1 d . . .
H47A H 0.6071 0.5775 0.4345 0.338 Uiso 1 1 calc R . .
H47B H 0.6523 0.5170 0.3387 0.338 Uiso 1 1 calc R . .
H47C H 0.7362 0.6222 0.4067 0.338 Uiso 1 1 calc R . .
O4 O 0.67436(14) 0.58674(13) 0.12634(12) 0.0563(4) Uani 1 1 d . . .
O5 O 0.89319(16) 0.55426(14) 0.07018(16) 0.0749(6) Uani 1 1 d . . .
H5A H 0.9579 0.5670 0.0473 0.112 Uiso 1 1 calc R . .
O6 O 0.89823(17) 0.38228(15) -0.00517(16) 0.0760(6) Uani 1 1 d . . .
C8 C 0.6470(2) 0.4724(2) 0.10251(17) 0.0543(6) Uani 1 1 d . . .
C10 C 0.5721(2) 0.6279(2) 0.15524(17) 0.0565(6) Uani 1 1 d . . .
C11 C 0.6738(2) 0.8324(2) 0.18948(18) 0.0589(6) Uani 1 1 d . . .
C14 C 0.4755(2) 0.5318(2) 0.14938(17) 0.0583(6) Uani 1 1 d . . .
C15 C 0.7258(2) 0.4101(2) 0.06772(19) 0.0586(6) Uani 1 1 d . . .
H15A H 0.7009 0.3326 0.0584 0.070 Uiso 1 1 calc R . .
C17 C 0.5753(2) 0.7373(2) 0.18285(18) 0.0596(6) Uani 1 1 d . . .
H17A H 0.5026 0.7560 0.2009 0.071 Uiso 1 1 calc R . .
C18 C 0.5215(2) 0.4360(2) 0.11812(17) 0.0576(6) Uani 1 1 d . . .
C19 C 0.7461(3) 1.0317(2) 0.2398(2) 0.0704(7) Uani 1 1 d . . .
H19A H 0.7318 1.1006 0.2701 0.085 Uiso 1 1 calc R . .
C20 C 0.8452(2) 0.4506(2) 0.04320(19) 0.0576(6) Uani 1 1 d . . .
C24 C 0.8548(2) 1.0269(2) 0.20265(19) 0.0632(6) Uani 1 1 d . . .
C27 C 0.6579(2) 0.9380(2) 0.2336(2) 0.0651(7) Uani 1 1 d . . .
H27A H 0.5857 0.9454 0.2596 0.078 Uiso 1 1 calc R . .
C28 C 0.4504(3) 0.3292(2) 0.1041(2) 0.0719(7) Uani 1 1 d . . .
H28A H 0.4819 0.2656 0.0823 0.086 Uiso 1 1 calc R . .
C30 C 0.3549(2) 0.5231(3) 0.1679(2) 0.0726(8) Uani 1 1 d . . .
H30A H 0.3225 0.5867 0.1883 0.087 Uiso 1 1 calc R . .
C31 C 0.8720(3) 0.9219(2) 0.1605(2) 0.0732(8) Uani 1 1 d . . .
H31A H 0.9452 0.9151 0.1359 0.088 Uiso 1 1 calc R . .
C35 C 0.7852(2) 0.8270(2) 0.1534(2) 0.0692(7) Uani 1 1 d . . .
H35A H 0.8008 0.7581 0.1243 0.083 Uiso 1 1 calc R . .
C36 C 0.9546(3) 1.1308(2) 0.2073(2) 0.0713(7) Uani 1 1 d . . .
C38 C 0.2850(3) 0.4169(3) 0.1549(2) 0.0861(10) Uani 1 1 d . . .
H38A H 0.2044 0.4091 0.1673 0.103 Uiso 1 1 calc R . .
C39 C 0.3322(3) 0.3213(3) 0.1236(2) 0.0863(9) Uani 1 1 d . . .
H39A H 0.2829 0.2510 0.1158 0.104 Uiso 1 1 calc R . .
C44 C 0.9133(4) 1.2392(3) 0.2473(4) 0.1204(14) Uani 1 1 d . . .
H44A H 0.8918 1.2355 0.3144 0.181 Uiso 1 1 calc R . .
H44B H 0.8435 1.2490 0.2023 0.181 Uiso 1 1 calc R . .
H44C H 0.9785 1.3015 0.2503 0.181 Uiso 1 1 calc R . .
C46 C 0.9857(4) 1.1395(3) 0.0998(3) 0.1204(15) Uani 1 1 d . . .
H46A H 1.0473 1.2046 0.1024 0.181 Uiso 1 1 calc R . .
H46B H 0.9137 1.1460 0.0558 0.181 Uiso 1 1 calc R . .
H46C H 1.0157 1.0735 0.0739 0.181 Uiso 1 1 calc R . .
C48 C 1.0687(4) 1.1224(3) 0.2766(4) 0.1227(15) Uani 1 1 d . . .
H48A H 1.0490 1.1146 0.3436 0.184 Uiso 1 1 calc R . .
H48B H 1.1284 1.1891 0.2804 0.184 Uiso 1 1 calc R . .
H48C H 1.1011 1.0582 0.2497 0.184 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 C7 1.362(3) . ?
O1 C9 1.400(3) . ?
O2 C16 1.263(3) . ?
O3 C16 1.275(3) . ?
C7 C25 1.339(3) . ?
C7 C23 1.458(3) . ?
C9 C13 1.324(3) . ?
C9 C22 1.460(3) . ?
C12 C33 1.370(4) . ?
C12 C34 1.374(4) . ?
C12 C26 1.530(4) . ?
C13 C21 1.454(3) . ?
C16 C25 1.440(3) . ?
C21 C32 1.377(3) . ?
C21 C29 1.388(4) . ?
C22 C23 1.376(4) . ?
C22 C41 1.389(4) . ?
C23 C37 1.384(3) . ?
C26 C45 1.426(5) . ?
C26 C47 1.466(6) . ?
C26 C43 1.482(6) . ?
C29 C33 1.380(4) . ?
C32 C34 1.374(4) . ?
C37 C42 1.363(4) . ?
C40 C41 1.367(4) . ?
C40 C42 1.395(5) . ?
O4 C8 1.366(3) . ?
O4 C10 1.397(3) . ?
O5 C20 1.280(3) . ?
O6 C20 1.253(3) . ?
C8 C15 1.338(3) . ?
C8 C18 1.455(3) . ?
C10 C17 1.330(4) . ?
C10 C14 1.452(3) . ?
C11 C27 1.392(4) . ?
C11 C35 1.398(4) . ?
C11 C17 1.456(4) . ?
C14 C18 1.386(4) . ?
C14 C30 1.392(4) . ?
C15 C20 1.442(3) . ?
C18 C28 1.392(4) . ?
C19 C27 1.374(4) . ?
C19 C24 1.376(4) . ?
C24 C31 1.382(4) . ?
C24 C36 1.541(4) . ?
C28 C39 1.370(4) . ?
C30 C38 1.383(4) . ?
C31 C35 1.374(4) . ?
C36 C48 1.511(5) . ?
C36 C44 1.523(4) . ?
C36 C46 1.530(5) . ?
C38 C39 1.391(5) . ?

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
C7 O1 C9 110.01(17) . . ?
C25 C7 O1 123.1(2) . . ?
C25 C7 C23 128.8(2) . . ?
O1 C7 C23 108.1(2) . . ?
C13 C9 O1 121.3(2) . . ?
C13 C9 C22 132.2(2) . . ?
O1 C9 C22 106.50(19) . . ?
C33 C12 C34 115.5(2) . . ?
C33 C12 C26 121.7(2) . . ?
C34 C12 C26 122.8(2) . . ?
C9 C13 C21 130.2(2) . . ?
O2 C16 O3 122.3(2) . . ?
O2 C16 C25 121.0(2) . . ?
O3 C16 C25 116.7(2) . . ?
C32 C21 C29 115.6(2) . . ?
C32 C21 C13 119.5(2) . . ?
C29 C21 C13 124.8(2) . . ?
C23 C22 C41 120.1(2) . . ?
C23 C22 C9 108.0(2) . . ?
C41 C22 C9 131.9(3) . . ?
C22 C23 C37 121.9(2) . . ?
C22 C23 C7 107.4(2) . . ?
C37 C23 C7 130.6(2) . . ?
C7 C25 C16 126.2(2) . . ?
C45 C26 C47 109.5(5) . . ?
C45 C26 C43 108.0(5) . . ?
C47 C26 C43 104.6(5) . . ?
C45 C26 C12 113.2(3) . . ?
C47 C26 C12 111.6(3) . . ?
C43 C26 C12 109.5(3) . . ?
C33 C29 C21 121.1(2) . . ?
C34 C32 C21 122.4(2) . . ?
C12 C33 C29 123.0(2) . . ?
C12 C34 C32 122.2(2) . . ?
C42 C37 C23 118.1(3) . . ?
C41 C40 C42 121.9(3) . . ?
C40 C41 C22 117.8(3) . . ?
C37 C42 C40 120.3(3) . . ?
C8 O4 C10 109.60(18) . . ?
C15 C8 O4 123.1(2) . . ?
C15 C8 C18 128.5(2) . . ?
O4 C8 C18 108.4(2) . . ?
C17 C10 O4 121.4(2) . . ?
C17 C10 C14 131.4(2) . . ?
O4 C10 C14 107.1(2) . . ?
C27 C11 C35 116.2(2) . . ?
C27 C11 C17 118.9(2) . . ?
C35 C11 C17 124.9(2) . . ?
C18 C14 C30 120.1(2) . . ?
C18 C14 C10 107.8(2) . . ?
C30 C14 C10 132.1(3) . . ?
C8 C15 C20 126.7(2) . . ?
C10 C17 C11 130.6(2) . . ?
C14 C18 C28 122.0(2) . . ?
C14 C18 C8 107.0(2) . . ?
C28 C18 C8 131.0(2) . . ?
C27 C19 C24 122.2(2) . . ?
O6 C20 O5 122.1(2) . . ?
O6 C20 C15 118.3(2) . . ?
O5 C20 C15 119.6(2) . . ?
C19 C24 C31 116.3(3) . . ?
C19 C24 C36 123.3(2) . . ?
C31 C24 C36 120.4(3) . . ?
C19 C27 C11 121.7(2) . . ?
C39 C28 C18 117.6(3) . . ?
C38 C30 C14 117.7(3) . . ?
C35 C31 C24 122.6(3) . . ?
C31 C35 C11 121.0(2) . . ?
C48 C36 C44 107.6(3) . . ?
C48 C36 C46 109.2(3) . . ?
C44 C36 C46 107.6(3) . . ?
C48 C36 C24 110.9(3) . . ?
C44 C36 C24 112.1(3) . . ?
C46 C36 C24 109.3(2) . . ?
C30 C38 C39 121.7(3) . . ?
C28 C39 C38 120.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 940368'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 O3'
_chemical_formula_weight         278.29

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                   8.0584(10)
_cell_length_b                   13.7851(14)
_cell_length_c                   14.5897(16)
_cell_angle_alpha                107.134(7)
_cell_angle_beta                 105.844(8)
_cell_angle_gamma                103.626(8)
_cell_volume                     1399.1(3)
_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       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12548
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         27.59
_reflns_number_total             6409
_reflns_number_gt                3390
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0875P)²+0.0177P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6409
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O4 O 0.5449(2) 0.64243(11) 0.47883(10) 0.0541(4) Uani 1 1 d . . .
O6 O 0.6547(2) 0.56160(13) 0.32110(11) 0.0680(5) Uani 1 1 d . . .
H6B H 0.5953 0.5910 0.3500 0.102 Uiso 1 1 calc R . .
O1 O 0.6589(2) 0.19558(11) -0.00774(10) 0.0552(4) Uani 1 1 d . . .
O3 O 0.7566(2) 0.38243(13) 0.15311(11) 0.0687(5) Uani 1 1 d . . .
H3B H 0.7745 0.4190 0.2128 0.103 Uiso 1 1 calc R . .
O5 O 0.8550(2) 0.47813(13) 0.35321(11) 0.0651(5) Uani 1 1 d . . .
O2 O 0.5908(2) 0.48667(13) 0.12463(12) 0.0702(5) Uani 1 1 d . . .
C36 C 0.6864(3) 0.61910(17) 0.53486(15) 0.0505(5) Uani 1 1 d . . .
C25 C 0.2173(3) 0.69837(18) 0.39561(17) 0.0552(6) Uani 1 1 d . . .
C29 C 0.4569(3) 0.68742(17) 0.54180(16) 0.0515(5) Uani 1 1 d . . .
C35 C 0.6928(3) 0.65256(17) 0.64021(16) 0.0534(6) Uani 1 1 d . . .
C5 C 0.7979(3) 0.04006(17) 0.06887(16) 0.0516(5) Uani 1 1 d . . .
C9 C 0.6515(3) 0.09675(17) -0.07404(15) 0.0514(5) Uani 1 1 d . . .
C30 C 0.5540(3) 0.69500(16) 0.64503(15) 0.0512(5) Uani 1 1 d . . .
C10 C 0.5691(3) 0.09006(18) -0.17862(15) 0.0537(6) Uani 1 1 d . . .
C8 C 0.7153(3) 0.02952(17) -0.03724(16) 0.0553(6) Uani 1 1 d . . .
H8A H 0.7055 -0.0340 -0.0872 0.066 Uiso 1 1 calc R . .
C28 C 0.3109(3) 0.71316(18) 0.50240(17) 0.0564(6) Uani 1 1 d . . .
H28A H 0.2622 0.7448 0.5494 0.068 Uiso 1 1 calc R . .
C16 C 0.5869(3) 0.25041(19) -0.06375(16) 0.0537(6) Uani 1 1 d . . .
C4 C 0.8013(3) 0.12084(19) 0.15455(17) 0.0594(6) Uani 1 1 d . . .
H4A H 0.7457 0.1709 0.1451 0.071 Uiso 1 1 calc R . .
C37 C 0.7882(3) 0.57178(17) 0.49165(16) 0.0551(6) Uani 1 1 d . . .
H37A H 0.8836 0.5605 0.5350 0.066 Uiso 1 1 calc R . .
C14 C 0.4478(3) 0.2005(2) -0.26100(18) 0.0679(7) Uani 1 1 d . . .
H14A H 0.4197 0.2629 -0.2573 0.081 Uiso 1 1 calc R . .
C18 C 0.6479(3) 0.40826(19) 0.09229(17) 0.0563(6) Uani 1 1 d . . .
C2 C 0.9729(3) 0.0556(2) 0.27145(17) 0.0610(6) Uani 1 1 d . . .
C38 C 0.7633(3) 0.53651(17) 0.38339(17) 0.0538(6) Uani 1 1 d . . .
C7 C 0.9705(4) -0.0242(2) 0.18686(18) 0.0700(7) Uani 1 1 d . . .
H7A H 1.0280 -0.0734 0.1968 0.084 Uiso 1 1 calc R . .
C17 C 0.5798(3) 0.34792(19) -0.01755(17) 0.0582(6) Uani 1 1 d . . .
H17A H 0.5263 0.3797 -0.0600 0.070 Uiso 1 1 calc R . .
C34 C 0.8089(3) 0.64694(19) 0.72730(18) 0.0672(7) Uani 1 1 d . . .
H34A H 0.9016 0.6182 0.7240 0.081 Uiso 1 1 calc R . .
C27 C 0.1465(3) 0.6192(2) 0.21232(19) 0.0695(7) Uani 1 1 d . . .
H27A H 0.1631 0.5725 0.1576 0.083 Uiso 1 1 calc R . .
C26 C 0.2404(3) 0.63094(19) 0.31205(17) 0.0625(6) Uani 1 1 d . . .
H26A H 0.3202 0.5930 0.3232 0.075 Uiso 1 1 calc R . .
C15 C 0.5266(3) 0.18317(18) -0.17257(16) 0.0556(6) Uani 1 1 d . . .
C11 C 0.5342(3) 0.0110(2) -0.27417(17) 0.0688(7) Uani 1 1 d . . .
H11A H 0.5631 -0.0513 -0.2787 0.083 Uiso 1 1 calc R . .
C3 C 0.8867(3) 0.1272(2) 0.25349(17) 0.0636(6) Uani 1 1 d . . .
H3A H 0.8858 0.1811 0.3093 0.076 Uiso 1 1 calc R . .
C6 C 0.8839(3) -0.03214(19) 0.08765(17) 0.0655(7) Uani 1 1 d . . .
H6A H 0.8833 -0.0872 0.0322 0.079 Uiso 1 1 calc R . .
C24 C 0.0938(3) 0.7514(2) 0.3745(2) 0.0703(7) Uani 1 1 d . . .
H24A H 0.0720 0.7953 0.4286 0.084 Uiso 1 1 calc R . .
C31 C 0.5270(4) 0.73317(18) 0.73733(17) 0.0637(6) Uani 1 1 d . . .
H31A H 0.4337 0.7613 0.7408 0.076 Uiso 1 1 calc R . .
C22 C 0.0290(3) 0.6751(2) 0.1923(2) 0.0697(7) Uani 1 1 d . . .
C1 C 1.0694(4) 0.0667(2) 0.38052(19) 0.0856(9) Uani 1 1 d . . .
H1A H 1.0555 0.1263 0.4282 0.128 Uiso 1 1 calc R . .
H1B H 1.1976 0.0794 0.3936 0.128 Uiso 1 1 calc R . .
H1C H 1.0165 0.0014 0.3890 0.128 Uiso 1 1 calc R . .
C23 C 0.0027(4) 0.7406(2) 0.2751(2) 0.0782(8) Uani 1 1 d . . .
H23A H -0.0777 0.7781 0.2637 0.094 Uiso 1 1 calc R . .
C33 C 0.7821(4) 0.6850(2) 0.81784(19) 0.0779(8) Uani 1 1 d . . .
H33A H 0.8582 0.6822 0.8770 0.094 Uiso 1 1 calc R . .
C12 C 0.4559(4) 0.0287(2) -0.36085(18) 0.0786(8) Uani 1 1 d . . .
H12A H 0.4310 -0.0227 -0.4253 0.094 Uiso 1 1 calc R . .
C13 C 0.4129(4) 0.1210(2) -0.35485(19) 0.0788(8) Uani 1 1 d . . .
H13A H 0.3592 0.1300 -0.4154 0.095 Uiso 1 1 calc R . .
C32 C 0.6428(4) 0.7281(2) 0.82355(18) 0.0744(8) Uani 1 1 d . . .
H32A H 0.6280 0.7536 0.8863 0.089 Uiso 1 1 calc R . .
C21 C -0.0657(4) 0.6647(3) 0.0834(2) 0.0978(10) Uani 1 1 d . . .
H21A H -0.0298 0.6161 0.0370 0.147 Uiso 1 1 calc R . .
H21B H -0.0311 0.7344 0.0793 0.147 Uiso 1 1 calc R . .
H21C H -0.1964 0.6370 0.0647 0.147 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
O4 C36 1.375(2) . ?
O4 C29 1.400(2) . ?
O6 C38 1.267(2) . ?
O1 C16 1.374(2) . ?
O1 C9 1.396(2) . ?
O3 C18 1.261(2) . ?
O5 C38 1.279(2) . ?
O2 C18 1.286(3) . ?
C36 C37 1.337(3) . ?
C36 C35 1.451(3) . ?
C25 C26 1.387(3) . ?
C25 C24 1.389(3) . ?
C25 C28 1.462(3) . ?
C29 C28 1.337(3) . ?
C29 C30 1.455(3) . ?
C35 C30 1.388(3) . ?
C35 C34 1.392(3) . ?
C5 C6 1.388(3) . ?
C5 C4 1.396(3) . ?
C5 C8 1.456(3) . ?
C9 C8 1.334(3) . ?
C9 C10 1.453(3) . ?
C30 C31 1.390(3) . ?
C10 C15 1.389(3) . ?
C10 C11 1.399(3) . ?
C16 C17 1.337(3) . ?
C16 C15 1.455(3) . ?
C4 C3 1.386(3) . ?
C37 C38 1.449(3) . ?
C14 C13 1.384(4) . ?
C14 C15 1.390(3) . ?
C18 C17 1.442(3) . ?
C2 C3 1.379(3) . ?
C2 C7 1.382(3) . ?
C2 C1 1.512(3) . ?
C7 C6 1.383(3) . ?
C34 C33 1.367(4) . ?
C27 C22 1.379(3) . ?
C27 C26 1.385(3) . ?
C11 C12 1.370(3) . ?
C24 C23 1.379(3) . ?
C31 C32 1.378(3) . ?
C22 C23 1.381(4) . ?
C22 C21 1.510(3) . ?
C33 C32 1.399(4) . ?
C12 C13 1.380(4) . ?

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
C36 O4 C29 110.29(16) . . ?
C16 O1 C9 110.11(15) . . ?
C37 C36 O4 122.12(19) . . ?
C37 C36 C35 130.6(2) . . ?
O4 C36 C35 107.26(18) . . ?
C26 C25 C24 117.1(2) . . ?
C26 C25 C28 123.6(2) . . ?
C24 C25 C28 119.3(2) . . ?
C28 C29 O4 120.52(19) . . ?
C28 C29 C30 132.7(2) . . ?
O4 C29 C30 106.80(18) . . ?
C30 C35 C34 121.1(2) . . ?
C30 C35 C36 108.18(18) . . ?
C34 C35 C36 130.7(2) . . ?
C6 C5 C4 117.1(2) . . ?
C6 C5 C8 118.8(2) . . ?
C4 C5 C8 124.1(2) . . ?
C8 C9 O1 121.06(18) . . ?
C8 C9 C10 132.1(2) . . ?
O1 C9 C10 106.85(17) . . ?
C35 C30 C31 120.7(2) . . ?
C35 C30 C29 107.44(18) . . ?
C31 C30 C29 131.8(2) . . ?
C15 C10 C11 120.9(2) . . ?
C15 C10 C9 107.88(19) . . ?
C11 C10 C9 131.2(2) . . ?
C9 C8 C5 130.1(2) . . ?
C29 C28 C25 128.9(2) . . ?
C17 C16 O1 121.50(19) . . ?
C17 C16 C15 130.8(2) . . ?
O1 C16 C15 107.73(18) . . ?
C3 C4 C5 120.7(2) . . ?
C36 C37 C38 125.9(2) . . ?
C13 C14 C15 117.2(2) . . ?
O3 C18 O2 122.2(2) . . ?
O3 C18 C17 120.2(2) . . ?
O2 C18 C17 117.55(19) . . ?
C3 C2 C7 117.7(2) . . ?
C3 C2 C1 120.4(2) . . ?
C7 C2 C1 121.9(2) . . ?
O6 C38 O5 121.4(2) . . ?
O6 C38 C37 121.6(2) . . ?
O5 C38 C37 117.03(19) . . ?
C2 C7 C6 121.1(2) . . ?
C16 C17 C18 125.8(2) . . ?
C33 C34 C35 117.8(2) . . ?
C22 C27 C26 121.5(2) . . ?
C27 C26 C25 121.1(2) . . ?
C10 C15 C14 121.1(2) . . ?
C10 C15 C16 107.40(18) . . ?
C14 C15 C16 131.4(2) . . ?
C12 C11 C10 117.5(2) . . ?
C2 C3 C4 121.8(2) . . ?
C7 C6 C5 121.6(2) . . ?
C23 C24 C25 121.6(3) . . ?
C32 C31 C30 118.0(2) . . ?
C27 C22 C23 117.6(2) . . ?
C27 C22 C21 120.6(3) . . ?
C23 C22 C21 121.8(2) . . ?
C24 C23 C22 121.1(2) . . ?
C34 C33 C32 121.5(2) . . ?
C11 C12 C13 121.6(2) . . ?
C12 C13 C14 121.7(2) . . ?
C31 C32 C33 120.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 940369'
