# Electronic Supplementary Material (ESI) for ChemComm.
# 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_HOF-4
_audit_creation_date             2014-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        HOF-4
_chemical_formula_moiety         'C61 H48 N20'
_chemical_formula_sum            'C61 H48 N20'
_chemical_formula_weight         1061.19
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y, z-1/2'

_cell_length_a                   20.212(6)
_cell_length_b                   7.275(2)
_cell_length_c                   26.666(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.606(6)
_cell_angle_gamma                90.00
_cell_volume                     3921(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13649
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.3
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.899
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20646
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.49
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                4534
_reflns_number_total             6927
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.0976
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+7.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2139
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Others
 Fixed U12: C1(0)
 Fixed U23: C1(0)
 Fixed Uiso: H3(0.054) H4(0.066) H6(0.053) H7(0.053) H9(0.103) H10(0.113)
 H12(0.086) H13(0.075) H18(0.05) H19(0.052) H21(0.054) H22(0.054) H24(0.072)
 H25(0.074) H27(0.06) H28(0.06) H4A(0.12) H4B(0.12) H5A(0.17) H5B(0.17)
 H9A(0.084) H9B(0.084) H10A(0.067) H10B(0.067)
 Fixed X: C1(0.25) H3(0.3198) H4(0.4045) H6(0.3954) H7(0.3105) H9(0.5135)
 H10(0.5977) H12(0.5269) H13(0.4409) H18(0.1902) H19(0.2228) H21(0.3976)
 H22(0.364) H24(0.2507) H25(0.2856) H27(0.4716) H28(0.4362) H4A(0.8026)
 H4B(0.765) H5A(0.7372) H5B(0.6745) H9A(0.3658) H9B(0.319) H10A(0.5415)
 H10B(0.5538)
 Fixed Y: H3(1.0873) H4(1.2766) H6(1.5374) H7(1.3462) H9(1.3602) H10(1.5434)
 H12(1.9563) H13(1.7783) H18(0.7863) H19(0.5602) H21(0.8172) H22(1.0404)
 H24(0.4171) H25(0.1546) H27(0.2629) H28(0.5263) H4A(1.8881) H4B(1.7121)
 H5A(2.3574) H5B(2.3425) H9A(-0.3804) H9B(-0.2231) H10A(-0.4182) H10B(-0.2664)
 Fixed Z: C1(0.75) H3(0.8389) H4(0.864) H6(0.7312) H7(0.7069) H9(0.8568)
 H10(0.8864) H12(0.8048) H13(0.7807) H18(0.7067) H19(0.6526) H21(0.6383)
 H22(0.693) H24(0.5845) H25(0.5431) H27(0.5856) H28(0.6254) H4A(0.9517)
 H4B(0.9497) H5A(0.8537) H5B(0.8241) H9A(0.4246) H9B(0.4285) H10A(0.5334)
 H10B(0.5698)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.2500 1.0660(7) 0.7500 0.0363(12) Uani 1 2 d S . .
C2 C 0.30628(19) 1.1906(5) 0.76959(14) 0.0382(9) Uani 1 1 d . . .
C3 C 0.3350(2) 1.1766(5) 0.81689(16) 0.0451(10) Uani 1 1 d . . .
H3 H 0.3198 1.0873 0.8389 0.054 Uiso 1 1 calc R . .
C4 C 0.3858(2) 1.2923(6) 0.83222(17) 0.0548(11) Uani 1 1 d . . .
H4 H 0.4045 1.2766 0.8640 0.066 Uiso 1 1 calc R . .
C5 C 0.4096(2) 1.4306(5) 0.80160(17) 0.0497(11) Uani 1 1 d . . .
C6 C 0.3804(2) 1.4477(5) 0.75311(16) 0.0439(10) Uani 1 1 d . . .
H6 H 0.3954 1.5374 0.7312 0.053 Uiso 1 1 calc R . .
C7 C 0.3297(2) 1.3309(5) 0.73849(15) 0.0439(10) Uani 1 1 d . . .
H7 H 0.3105 1.3462 0.7069 0.053 Uiso 1 1 calc R . .
C8 C 0.4648(3) 1.5511(6) 0.81770(18) 0.0586(12) Uani 1 1 d . . .
C9 C 0.5146(4) 1.4833(9) 0.8475(3) 0.142(4) Uani 1 1 d . . .
H9 H 0.5135 1.3602 0.8568 0.103 Uiso 1 1 calc R . .
C10 C 0.5664(4) 1.5917(10) 0.8642(4) 0.147(4) Uani 1 1 d . . .
H10 H 0.5977 1.5434 0.8864 0.113 Uiso 1 1 calc R . .
C11 C 0.5720(3) 1.7701(7) 0.84827(18) 0.0683(14) Uani 1 1 d . . .
C12 C 0.5241(3) 1.8362(7) 0.8166(2) 0.0718(15) Uani 1 1 d . . .
H12 H 0.5269 1.9563 0.8048 0.086 Uiso 1 1 calc R . .
C13 C 0.4726(3) 1.7286(6) 0.80223(19) 0.0622(13) Uani 1 1 d . . .
H13 H 0.4409 1.7783 0.7807 0.075 Uiso 1 1 calc R . .
C14 C 0.6312(3) 1.8763(7) 0.86438(19) 0.0660(14) Uani 1 1 d . . .
C15 C 0.7255(3) 1.9012(8) 0.9106(2) 0.091(2) Uani 1 1 d . . .
C16 C 0.6908(4) 2.1362(10) 0.8656(4) 0.135(4) Uani 1 1 d . . .
C17 C 0.27383(19) 0.9351(5) 0.70830(14) 0.0383(9) Uani 1 1 d . . .
C18 C 0.2327(2) 0.7910(5) 0.69375(15) 0.0413(9) Uani 1 1 d . . .
H18 H 0.1902 0.7863 0.7067 0.050 Uiso 1 1 calc R . .
C19 C 0.2519(2) 0.6546(5) 0.66092(15) 0.0437(10) Uani 1 1 d . . .
H19 H 0.2228 0.5602 0.6526 0.052 Uiso 1 1 calc R . .
C20 C 0.3155(2) 0.6584(5) 0.64007(14) 0.0432(10) Uani 1 1 d . . .
C21 C 0.3559(2) 0.8081(5) 0.65260(15) 0.0451(10) Uani 1 1 d . . .
H21 H 0.3976 0.8172 0.6383 0.054 Uiso 1 1 calc R . .
C22 C 0.3358(2) 0.9429(5) 0.68571(15) 0.0449(10) Uani 1 1 d . . .
H22 H 0.3640 1.0404 0.6930 0.054 Uiso 1 1 calc R . .
C23 C 0.3389(2) 0.4995(5) 0.61019(15) 0.0441(10) Uani 1 1 d . . .
C24 C 0.2954(3) 0.3869(6) 0.58507(18) 0.0604(13) Uani 1 1 d . . .
H24 H 0.2507 0.4171 0.5845 0.072 Uiso 1 1 calc R . .
C25 C 0.3161(2) 0.2277(6) 0.56021(18) 0.0614(13) Uani 1 1 d . . .
H25 H 0.2856 0.1546 0.5431 0.074 Uiso 1 1 calc R . .
C26 C 0.3818(2) 0.1806(6) 0.56126(16) 0.0529(11) Uani 1 1 d . . .
C27 C 0.4269(2) 0.2930(6) 0.58543(16) 0.0500(10) Uani 1 1 d . . .
H27 H 0.4716 0.2629 0.5856 0.060 Uiso 1 1 calc R . .
C28 C 0.4054(2) 0.4510(5) 0.60943(17) 0.0502(11) Uani 1 1 d . . .
H28 H 0.4362 0.5263 0.6254 0.060 Uiso 1 1 calc R . .
C29 C 0.4042(2) 0.0081(6) 0.53551(17) 0.0511(11) Uani 1 1 d . . .
C30 C 0.3878(3) -0.2159(7) 0.47819(19) 0.0680(14) Uani 1 1 d . . .
C31 C 0.4760(2) -0.2296(5) 0.52986(16) 0.0449(10) Uani 1 1 d . . .
N1 N 0.6748(3) 1.7952(7) 0.8948(2) 0.105(2) Uani 1 1 d . . .
N2 N 0.7355(3) 2.0702(7) 0.8990(2) 0.0877(16) Uani 1 1 d . . .
N3 N 0.6367(3) 2.0449(6) 0.8472(2) 0.0914(17) Uani 1 1 d . . .
N4 N 0.7694(4) 1.8250(9) 0.9408(3) 0.159(4) Uani 1 1 d . . .
H4A H 0.8026 1.8881 0.9517 0.120 Uiso 1 1 calc R . .
H4B H 0.7650 1.7121 0.9497 0.120 Uiso 1 1 calc R . .
N5 N 0.7021(6) 2.2971(11) 0.8455(7) 0.212(14) Uani 1 1 d . . .
H5A H 0.7372 2.3574 0.8537 0.170 Uiso 1 1 calc R . .
H5B H 0.6745 2.3425 0.8241 0.170 Uiso 1 1 calc R . .
N6 N 0.3658(2) -0.0554(5) 0.49859(16) 0.0650(12) Uani 1 1 d . . .
N7 N 0.44070(19) -0.3097(5) 0.49326(13) 0.0513(9) Uani 1 1 d . . .
N8 N 0.46019(17) -0.0689(4) 0.55298(13) 0.0455(8) Uani 1 1 d . . .
N9 N 0.3535(3) -0.2808(7) 0.4392(2) 0.105(2) Uani 1 1 d . . .
H9A H 0.3658 -0.3804 0.4246 0.084 Uiso 1 1 calc R . .
H9B H 0.3190 -0.2231 0.4285 0.084 Uiso 1 1 calc R . .
N10 N 0.53013(18) -0.3147(5) 0.54629(15) 0.0555(10) Uani 1 1 d . . .
H10A H 0.5415 -0.4182 0.5334 0.067 Uiso 1 1 calc R . .
H10B H 0.5538 -0.2664 0.5698 0.067 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
C1 C2 1.541(5) . ?
C1 C2 1.541(5) 2_556 ?
C1 C17 1.545(5) . ?
C1 C17 1.545(5) 2_556 ?
C2 C3 1.387(5) . ?
C2 C7 1.401(5) . ?
C3 C4 1.386(6) . ?
C4 C5 1.385(6) . ?
C5 C6 1.421(6) . ?
C5 C8 1.479(6) . ?
C6 C7 1.384(5) . ?
C8 C9 1.368(7) . ?
C8 C13 1.365(6) . ?
C9 C10 1.382(8) . ?
C10 C11 1.370(8) . ?
C11 C12 1.366(7) . ?
C11 C14 1.484(7) . ?
C12 C13 1.354(7) . ?
C14 N1 1.328(7) . ?
C14 N3 1.315(7) . ?
C15 N1 1.346(7) . ?
C15 N2 1.285(7) . ?
C15 N4 1.316(8) . ?
C16 N2 1.349(9) . ?
C16 N3 1.365(8) . ?
C16 N5 1.309(10) . ?
C17 C18 1.390(5) . ?
C17 C22 1.396(6) . ?
C18 C19 1.382(5) . ?
C19 C20 1.405(6) . ?
C20 C21 1.400(6) . ?
C20 C23 1.485(5) . ?
C21 C22 1.384(6) . ?
C23 C24 1.371(6) . ?
C23 C28 1.390(6) . ?
C24 C25 1.401(6) . ?
C25 C26 1.370(6) . ?
C26 C27 1.380(6) . ?
C26 C29 1.503(5) . ?
C27 C28 1.388(6) . ?
C29 N6 1.329(6) . ?
C29 N8 1.342(5) . ?
C30 N6 1.364(6) . ?
C30 N7 1.327(6) . ?
C30 N9 1.331(6) . ?
C31 N7 1.336(5) . ?
C31 N8 1.361(5) . ?
C31 N10 1.328(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
C2 C1 C2 108.0(4) . 2_556 ?
C2 C1 C17 111.8(2) . . ?
C2 C1 C17 110.7(2) 2_556 . ?
C2 C1 C17 110.7(2) . 2_556 ?
C2 C1 C17 111.8(2) 2_556 2_556 ?
C17 C1 C17 103.9(4) 2_556 . ?
C3 C2 C1 124.5(3) . . ?
C3 C2 C7 116.8(3) . . ?
C7 C2 C1 118.7(3) . . ?
C4 C3 C2 121.7(4) . . ?
C5 C4 C3 121.9(4) . . ?
C4 C5 C6 117.2(4) . . ?
C4 C5 C8 121.7(4) . . ?
C6 C5 C8 121.1(4) . . ?
C7 C6 C5 120.1(4) . . ?
C6 C7 C2 122.3(4) . . ?
C9 C8 C5 120.2(4) . . ?
C13 C8 C5 124.2(4) . . ?
C13 C8 C9 115.4(4) . . ?
C8 C9 C10 122.2(5) . . ?
C11 C10 C9 120.3(6) . . ?
C10 C11 C14 118.2(5) . . ?
C12 C11 C10 117.7(5) . . ?
C12 C11 C14 124.0(5) . . ?
C13 C12 C11 120.6(5) . . ?
C12 C13 C8 123.5(5) . . ?
N1 C14 C11 118.2(5) . . ?
N3 C14 C11 117.1(5) . . ?
N3 C14 N1 124.6(5) . . ?
N2 C15 N1 126.4(6) . . ?
N2 C15 N4 116.4(5) . . ?
N4 C15 N1 117.2(5) . . ?
N2 C16 N3 126.2(6) . . ?
N5 C16 N2 118.0(6) . . ?
N5 C16 N3 115.6(7) . . ?
C18 C17 C1 118.4(3) . . ?
C18 C17 C22 116.5(3) . . ?
C22 C17 C1 125.0(3) . . ?
C19 C18 C17 123.1(4) . . ?
C18 C19 C20 120.1(4) . . ?
C19 C20 C23 119.7(4) . . ?
C21 C20 C19 117.1(3) . . ?
C21 C20 C23 123.0(4) . . ?
C22 C21 C20 121.9(4) . . ?
C21 C22 C17 121.2(4) . . ?
C24 C23 C20 121.4(4) . . ?
C24 C23 C28 117.1(4) . . ?
C28 C23 C20 121.3(4) . . ?
C23 C24 C25 122.1(4) . . ?
C26 C25 C24 119.5(4) . . ?
C25 C26 C27 119.8(4) . . ?
C25 C26 C29 119.7(4) . . ?
C27 C26 C29 120.4(4) . . ?
C26 C27 C28 119.8(4) . . ?
C27 C28 C23 121.7(4) . . ?
N6 C29 C26 116.9(4) . . ?
N6 C29 N8 126.5(4) . . ?
N8 C29 C26 116.6(4) . . ?
N7 C30 N6 125.8(4) . . ?
N7 C30 N9 117.8(4) . . ?
N9 C30 N6 116.5(4) . . ?
N7 C31 N8 125.4(4) . . ?
N10 C31 N7 118.0(4) . . ?
N10 C31 N8 116.6(4) . . ?
C14 N1 C15 115.8(5) . . ?
C15 N2 C16 113.2(5) . . ?
C14 N3 C16 113.6(5) . . ?
C29 N6 C30 113.7(4) . . ?
C30 N7 C31 114.7(4) . . ?
C29 N8 C31 113.7(4) . . ?

_platon_squeeze_details          
;
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.500 -0.036 0.000 384.1 11.7
2 0.250 0.039 0.250 425.5 13.7
3 1.000 -0.027 0.500 384.1 11.7
4 0.750 -0.101 0.750 425.6 13.4

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
_database_code_depnum_ccdc_archive 'CCDC 1010353'
