Semiconducting single crystals comprising segregated arrays of complexes of c60.
Barnes, Jonathan C.; Dale, Edward J.; Prokofjevs, Aleksandrs; Narayanan, Ashwin; Gibbs-Hall, Ian C; Juríček, Michal; Stern, Charlotte L.; Sarjeant, Amy A.; Botros, Youssry Y.; Stupp, Samuel I.; Stoddart, J. Fraser; Journal of the American Chemical Society 137 (2015) 2392–2399; doi:10.1021/ja512959g

data_4123419
_publ_section_title
;
 Semiconducting single crystals comprising segregated arrays of complexes
 of c60.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2392
_journal_page_last               2399
_journal_paper_doi               10.1021/ja512959g
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety
'C60 H48 N4, C60, 4(F6 P), 6(C7 H8), 2(C3 H7 N O)'
_chemical_formula_sum            'C168 H110 F24 N6 O2 P4'
_chemical_formula_weight         2824.49
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2013-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                83.1741(17)
_cell_angle_beta                 65.6972(15)
_cell_angle_gamma                82.9265(16)
_cell_formula_units_Z            2
_cell_length_a                   17.5692(4)
_cell_length_b                   19.4448(5)
_cell_length_c                   20.6000(5)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.850
_cell_measurement_theta_min      6.405
_cell_volume                     6347.0(3)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.94
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43241
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         63.687
_diffrn_reflns_theta_min         5.325
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0603 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.8655.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       needle
_exptl_crystal_F_000             2904
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.276
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1776
_refine_ls_number_reflns         20638
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.1091
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0955P)^2^+41.5581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2692
_refine_ls_wR_factor_ref         0.2826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16095
_reflns_number_total             20638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja512959g_si_004.cif
_cod_data_source_block           n3200
_cod_depositor_comments
'Adding full bibliography for 4123417--4123419.cif.'
_cod_database_code               4123419
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.574
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1D) = Uanis(C1F) = Uanis(C1G) = Uanis(C1B) = Uanis(C1A) = Uanis(C1C) =
Uanis(C156) = Uanis(C157) = Uanis(C161) = Uanis(C158) = Uanis(C160) =
Uanis(C159)
Uanis(C162) = Uanis(C1E)
Uanis(C152) = Uanis(C153) = Uanis(C151) = Uanis(C154) = Uanis(C150) =
Uanis(C149) = Uanis(C155)
Uanis(C1N) = Uanis(C155)
Uanis(C152) = Uanis(C153) = Uanis(C151) = Uanis(C154) = Uanis(C150) =
Uanis(C149) = Uanis(C155) = Uanis(C1K) = Uanis(C1H) = Uanis(C1M) = Uanis(C1L) =
Uanis(C1N) = Uanis(C1J) = Uanis(C1I)
3. Rigid body (RIGU) restrains
 C1E, C1B, C1C, C1D, C1A, C1F, C1G, C162, C156, C157, C161, C158, C160, C159,
 C155, C152, C153, C151, C154, C150, C149, C1I, C1H, C1M, C1L, C1N, C1K, C1J
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C168, O2, C166, N6, H166, C167, H16J, H16K, H16L, H16M, H16N, H16O, N5, O1,
 C163, H163, C164, C165, H16D, H16E, H16F, H16G, H16H, H16I
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(C1B)=Sof(C1C)=Sof(H1C)=Sof(C1A)=Sof(H1AA)=Sof(C1G)=Sof(H1G)=Sof(C1F)=
 Sof(H1F)=Sof(C1D)=Sof(H1D)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=1-FVAR(1)
 Sof(C156)=Sof(C157)=Sof(H157)=Sof(C158)=Sof(H158)=Sof(C159)=Sof(H159)=
 Sof(C160)=Sof(H160)=Sof(C161)=Sof(H161)=Sof(C162)=Sof(H16A)=Sof(H16B)=
 Sof(H16C)=FVAR(1)
 Sof(C1H)=Sof(C1M)=Sof(H1M)=Sof(C1K)=Sof(H1K)=Sof(C1I)=Sof(H1I)=Sof(C1J)=
 Sof(H1J)=Sof(C1L)=Sof(H1L)=Sof(C1N)=Sof(H1NA)=Sof(H1NB)=Sof(H1NC)=1-FVAR(2)
 Sof(C149)=Sof(C150)=Sof(H150)=Sof(C151)=Sof(H151)=Sof(C152)=Sof(H152)=
 Sof(C153)=Sof(H153)=Sof(C154)=Sof(H154)=Sof(C155)=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C18(H18A,H18B), C31(H31A,H31B), C48(H48A,H48B)
5.b Me refined with riding coordinates:
 C1E(H1EA,H1EB,H1EC), C167(H16J,H16K,H16L), C168(H16M,H16N,H16O)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
  C27(H27), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36),
 C38(H38), C39(H39), C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47),
  C50(H50), C51(H51), C53(H53), C54(H54), C56(H56), C57(H57), C59(H59),
 C60(H60), C129(H129), C130(H130), C131(H131), C132(H132), C133(H133),
 C122(H122), C123(H123), C124(H124), C125(H125), C126(H126), C157(H157),
 C158(H158), C159(H159), C160(H160), C161(H161), C150(H150), C151(H151),
 C152(H152), C153(H153), C154(H154), C143(H143), C144(H144), C145(H145),
 C146(H146), C147(H147), C136(H136), C137(H137), C138(H138), C139(H139),
 C140(H140), C1M(H1M), C1K(H1K), C1I(H1I), C1J(H1J), C1L(H1L), C1C(H1C),
 C1A(H1AA), C1G(H1G), C1F(H1F), C1D(H1D), C163(H163), C166(H166)
5.d Fitted hexagon refined as free rotating group:
 C156(C157,C158,C159,C160,C161), C149(C150,C151,C152,C153,C154), C1H(C1M,C1K,
 C1I,C1J,C1L), C1B(C1C,C1A,C1G,C1F,C1D)
5.e Idealised Me refined as rotating group:
 C134(H13A,H13B,H13C), C127(H12A,H12B,H12C), C162(H16A,H16B,H16C), C155(H15A,
 H15B,H15C), C148(H14A,H14B,H14C), C141(H14D,H14E,H14F), C1N(H1NA,H1NB,H1NC),
 C164(H16D,H16E,H16F), C165(H16G,H16H,H16I)
;
_shelx_res_checksum              36209
_shelx_hkl_checksum              90495