# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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_rev-n_PCBM
_database_code_depnum_ccdc_archive 'CCDC 907694'
_iucr_compatibility_tag          ?
_chemical_name_common            PCBM
_chemical_formula_moiety         'C72 H14 O2'
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C72 H14 O2'
_chemical_formula_weight         910.84
_chemical_melting_point          ?
_chemical_compound_source        commercial
loop_
_atom_type_symbol
_atom_type_description
# _atom_type_scat_dispersion_real
# _atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 'International Tables for Crystallography (Vol. IV)'
H H 'International Tables for Crystallography (Vol. IV)'
O O 'International Tables for Crystallography (Vol. IV)'
#==============================================================================
# 1.5. POWDER SPECIMEN AND CRYSTAL DATA
_space_group_crystal_system      monoclinic
_symmetry_space_group_name_H-M   P21/n
_space_group_name_Hall           ?
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                   13.49507(45)
_cell_length_b                   15.15724(38)
_cell_length_c                   19.09638(69)
_cell_angle_alpha                90
_cell_angle_beta                 107.1420(22)
_cell_angle_gamma                90
_cell_volume                     3732.61(21)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_pd_calibration_special_details  
; ?
;
_cell_special_details            
; ?
;
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      1.61
_exptl_crystal_density_method    floatation
_exptl_crystal_F_000             1848
# The next three fields give the specimen dimensions in mm. The equatorial
# plane contains the incident and diffracted beam.
_pd_spec_size_axial              15 # perpendicular to
# equatorial plane
_pd_spec_size_equat              15 # parallel to the scattering
# vector in transmission
_pd_spec_size_thick              0.25 # parallel to the scattering
# vector in reflection
# The next five fields are character fields that describe the specimen.
_pd_spec_mounting                
;
packed powder pellet
;
_pd_spec_mount_mode              reflection # options are 'reflection'
# or 'transmission'
_pd_spec_shape                   flat_sheet # options are 'cylinder',
# 'flat_sheet' or 'irregular'
_pd_char_particle_morphology     prismatic
_pd_char_colour                  black # use ICDD colour descriptions
# The next four fields are normally only needed for transmission experiments.
_exptl_absorpt_coefficient_mu    ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
#==============================================================================
# 1.6. EXPERIMENTAL DATA
_exptl_special_details           
; ?
;
# This following item is used to identify the equipment used to record the
# powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.
_pd_instr_location               
; ?
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_probe          x-ray
_diffrn_source_target            Cu
_diffrn_source_type              'sealed X-ray tube'
_diffrn_measurement_device_type  'Panalytical XPERT-PRO'
_diffrn_detector_type            "Panalytical X'Celerator RTMS detector"
_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;
loop_
_diffrn_radiation_type
'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  'Ni filter'
# The following four items give details of the measured (not processed)
# powder pattern. Angles are in degrees.
_pd_meas_number_of_points        8976
_pd_meas_2theta_range_min        5
_pd_meas_2theta_range_max        80
_pd_meas_2theta_range_inc        0.0084
# The following three items are used for time-of-flight measurements only.
_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?
# The following fields are used to identify the programs used.
_computing_data_collection       "Panalytical XPERT-PRO X'Pert Data Collector"
_computing_cell_refinement       'TOPAS ACADEMIC 4.1'
_computing_data_reduction        ?
_computing_structure_solution    'TOPAS ACADEMIC 4.1'
_computing_structure_refinement  'TOPAS ACADEMIC 4.1'
_computing_molecular_graphics    ?
_computing_publication_material  ?
#==============================================================================
# 1.7. REFINEMENT DATA
# Use the next field to give any special details about the fitting of the
# powder pattern.
_pd_proc_ls_special_details      
;
1) The use of a rigid body description the entire PCBM molecule
does not allow the derivation of statistically meaningful
s.u.'s for its atoms.
S.u.'s are available only for the center of mass (X, Y, Z),
the rotation angles (RX, RZ, RZ) and the 6 refined torsion (PHI1-PHI6)
of PCBM
X, Y, Z -0.4803(3), 0.1353(3), -0.7215(3)
RX, RY, RZ -264.4(2), 20.50(7), 190.6(2)
PHI1(C72-O1-C71-C70) -177.7 (1.7)
PHI2(O1-C71-C70-C69) 123.5 (9)
PHI3(C71-C70-C69-C68) -44.7(9)
PHI4(C70-C69-C68-C61) 175.7(3)
PHI5(CC69-C68-C61-C59) -150.8(6)
PHI6(C63-C62-C61-C59) -56.3(4)
2) The imperfect agreement between the experimental and the calculated
traces are reasonably due to the low number of of optimized structural
parameters with respect to the structure complexity
;
# The next three items are given as text
_pd_proc_ls_profile_function     'empirical parametrization'
_pd_proc_ls_background_function  'Chebychev polynomial'
_pd_proc_ls_pref_orient_corr     
; March-Dollase
AXIS 1 Ratio= 0.986(2) h= 2.000 k= 0.000 l=13.000
;
_pd_proc_ls_prof_R_factor        0.0824
_pd_proc_ls_prof_wR_factor       0.1068
_pd_proc_ls_prof_wR_expected     0.0238
_refine_special_details          
; ?
;
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           fullcycle
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     38
_refine_ls_number_restraints     ?
_refine_ls_number_constraints    ?
# The following item is 'CHI squared'
_refine_ls_goodness_of_fit_all   ?
_refine_ls_restrained_S_all      ?
_refine_ls_restrained_S_obs      ?
_refine_ls_shift/su_max          .01
_refine_ls_shift/su_mean         ?
# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the
# intensities used in the refinement.
_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        80
_pd_proc_2theta_range_inc        0.0084
loop_
_pd_proc_wavelength
1.540562
1.544390
_pd_block_diffractogram_id       ? # The id used for the block
# containing the powder
# pattern profile (section 11).
# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?
#==============================================================================
# 1.8. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1 C 4 -0.7578111 0.3610159 -1.778474 1 18.55(17)
C2 C 4 -0.7632577 0.2704728 -1.770574 1 18.55(17)
C3 C 4 -0.7747035 0.2332223 -1.70362 1 18.55(17)
C4 C 4 -0.7812991 0.2886201 -1.647224 1 18.55(17)
C5 C 4 -0.7746194 0.3834633 -1.655168 1 18.55(17)
C6 C 4 -0.7633376 0.4188472 -1.719109 1 18.55(17)
C7 C 4 -0.8217182 0.4971198 -1.75154 1 18.55(17)
C8 C 4 -0.8524206 0.4869884 -1.830229 1 18.55(17)
C9 C 4 -0.8133298 0.4031029 -1.847152 1 18.55(17)
C10 C 4 -0.8719816 0.3523552 -1.905014 1 18.55(17)
C11 C 4 -0.8777969 0.2571387 -1.897198 1 18.55(17)
C12 C 4 -0.8240987 0.2170619 -1.831109 1 18.55(17)
C13 C 4 -0.8728568 0.1474287 -1.801524 1 18.55(17)
C14 C 4 -0.8421398 0.1573456 -1.7223 1 18.55(17)
C15 C 4 -0.9135535 0.1397532 -1.684085 1 18.55(17)
C16 C 4 -0.9193306 0.1982189 -1.625278 1 18.55(17)
C17 C 4 -0.854903 0.2710865 -1.607408 1 18.55(17)
C18 C 4 -0.8951448 0.3548767 -1.591282 1 18.55(17)
C19 C 4 -0.8455387 0.4244692 -1.620413 1 18.55(17)
C20 C 4 -0.9008499 0.4989388 -1.650818 1 18.55(17)
C21 C 4 -0.8886431 0.5361947 -1.717646 1 18.55(17)
C22 C 4 -0.9895041 0.5665896 -1.762032 1 18.55(17)
C23 C 4 -1.01958 0.5570461 -1.837555 1 18.55(17)
C24 C 4 -0.9495805 0.5163805 -1.872544 1 18.55(17)
C25 C 4 -1.010533 0.4635652 -1.933291 1 18.55(17)
C26 C 4 -0.9725476 0.3830147 -1.949025 1 18.55(17)
C27 C 4 -1.040517 0.3075059 -1.967788 1 18.55(17)
C28 C 4 -0.9820266 0.2295374 -1.935888 1 18.55(17)
C29 C 4 -1.028981 0.1634184 -1.907275 1 18.55(17)
C30 C 4 -0.9731036 0.1210212 -1.838699 1 18.55(17)
C31 C 4 -1.047002 0.1025848 -1.798946 1 18.55(17)
C32 C 4 -1.017411 0.1118133 -1.722925 1 18.55(17)
C33 C 4 -1.063365 0.5480139 -1.721988 1 18.55(17)
C34 C 4 -1.009157 0.5069599 -1.653465 1 18.55(17)
C35 C 4 -1.163271 0.5204373 -1.759443 1 18.55(17)
C36 C 4 -1.193667 0.5107449 -1.838144 1 18.55(17)
C37 C 4 -1.123145 0.5290108 -1.876696 1 18.55(17)
C38 C 4 -1.265349 0.4377689 -1.858442 1 18.55(17)
C39 C 4 -1.259036 0.381665 -1.913691 1 18.55(17)
C40 C 4 -1.1835 0.3988005 -1.952619 1 18.55(17)
C41 C 4 -1.118798 0.4712855 -1.936054 1 18.55(17)
C42 C 4 -1.144172 0.3150749 -1.969118 1 18.55(17)
C43 C 4 -1.19346 0.2457052 -1.939464 1 18.55(17)
C44 C 4 -1.264932 0.285491 -1.905093 1 18.55(17)
C45 C 4 -1.137045 0.1711478 -1.909919 1 18.55(17)
C46 C 4 -1.147871 0.1336933 -1.842844 1 18.55(17)
C47 C 4 -1.214297 0.1740973 -1.809115 1 18.55(17)
C48 C 4 -1.183832 0.1837644 -1.730798 1 18.55(17)
C49 C 4 -1.087789 0.1529156 -1.688236 1 18.55(17)
C50 C 4 -1.027879 0.2058268 -1.628066 1 18.55(17)
C51 C 4 -1.067278 0.2868183 -1.613313 1 18.55(17)
C52 C 4 -0.9989995 0.3620438 -1.594195 1 18.55(17)
C53 C 4 -1.057522 0.4399329 -1.626163 1 18.55(17)
C54 C 4 -1.16216 0.4129173 -1.665069 1 18.55(17)
C55 C 4 -1.167821 0.3164549 -1.656467 1 18.55(17)
C56 C 4 -1.226644 0.2651886 -1.713367 1 18.55(17)
C57 C 4 -1.276669 0.2492847 -1.841779 1 18.55(17)
C58 C 4 -1.215468 0.4535655 -1.729668 1 18.55(17)
C59 C 4 -1.291395 0.4081837 -1.791879 1 18.55(17)
C60 C 4 -1.297595 0.3019374 -1.782242 1 18.55(17)
C61 C 4 -1.390136 0.3626692 -1.789249 1 19.55(17)
C62 C 4 -1.477738 0.3526581 -1.859272 1 19.55(17)
C63 C 4 -1.518981 0.4268859 -1.900757 1 20.55(17)
C64 C 4 -1.599949 0.4185705 -1.965579 1 20.55(17)
C65 C 4 -1.639782 0.3360405 -1.98899 1 20.55(17)
C66 C 4 -1.599422 0.2618569 -1.948226 1 20.55(17)
C67 C 4 -1.518839 0.2699857 -1.883697 1 20.55(17)
C68 C 4 -1.422897 0.3770524 -1.719727 1 19.55(17)
C69 C 4 -1.483944 0.3006609 -1.700595 1 21.55(17)
C70 C 4 -1.506448 0.3174563 -1.627392 1 21.55(17)
C71 C 4 -1.412422 0.3515419 -1.569477 1 21.55(17)
O1 O 4 -1.431605 0.4288635 -1.542018 1 21.55(17)
C72 C 4 -1.344339 0.4692521 -1.487541 1 22.55(17)
O2 O 4 -1.329251 0.3146174 -1.549507 1 21.55(17)
H1 H 4 -1.492195 0.484151 -1.883131 1 22.55(17)
H2 H 4 -1.626956 0.4685678 -1.993892 1 22.55(17)
H3 H 4 -1.693649 0.3264417 -2.033643 1 22.55(17)
H4 H 4 -1.625511 0.2029297 -1.965142 1 22.55(17)
H5 H 4 -1.488271 0.2151966 -1.856171 1 22.55(17)
H6 H 4 -1.355161 0.3856371 -1.67652 1 23.55(17)
H7 H 4 -1.468774 0.4314512 -1.725703 1 23.55(17)
H8 H 4 -1.551858 0.2958307 -1.741825 1 23.55(17)
H9 H 4 -1.442071 0.2409136 -1.695873 1 23.55(17)
H10 H 4 -1.564063 0.3630772 -1.633569 1 23.55(17)
H11 H 4 -1.532578 0.2615314 -1.613971 1 23.55(17)
H12 H 4 -1.291777 0.4823014 -1.511342 1 24.55(17)
H13 H 4 -1.372813 0.5246842 -1.470737 1 24.55(17)
H14 H 4 -1.314493 0.4269698 -1.443958 1 24.55(17)