Tuning Up an Electronic Structure of the Subphthalocyanine Derivatives toward Electron-Transfer Process in Noncovalent Complexes with C<sub>60</sub> and C<sub>70</sub> Fullerenes: Experimental and Theoretical Studies.
Rhoda, Hannah M.; Kayser, Mathew P.; Wang, Yefeng; Nazarenko, Alexander Y.; Belosludov, Rodion V.; Kiprof, Paul; Blank, David A.; Nemykin, Victor N.; Inorganic chemistry 55 (2016) 9549–9563; doi:10.1021/acs.inorgchem.6b00992

data_4348124
_publ_section_title
;
 Tuning Up an Electronic Structure of the Subphthalocyanine Derivatives
 toward Electron-Transfer Process in Noncovalent Complexes with
 C<sub>60</sub> and C<sub>70</sub> Fullerenes: Experimental and
 Theoretical Studies.
;
_journal_issue                   19
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9549
_journal_page_last               9563
_journal_paper_doi               10.1021/acs.inorgchem.6b00992
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         '2(C60 H36 B1 Cl1 N6 S6), 12(C60), 2(C6)'
_chemical_formula_sum            'C852 H72 B2 Cl2 N12 S12'
_chemical_formula_weight         10950.89
_space_group_crystal_system      hexagonal
_space_group_IT_number           176
_space_group_name_Hall           '-P 6c'
_space_group_name_H-M_alt        'P 63/m'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   25.560(7)
_cell_length_b                   25.560(7)
_cell_length_c                   39.513(5)
_cell_measurement_reflns_used    6461
_cell_measurement_temperature    123
_cell_measurement_theta_max      17.2
_cell_measurement_theta_min      0.9
_cell_volume                     22356(9)
_computing_cell_refinement
;
CrystalClear 2.0 r12 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear 2.0 r12 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.420
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
scan:
	Number of images: 30
	           Slice: 124.0000 - 184.0000
	     Image width: 2.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 30.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
;
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.031319
_diffrn_orient_matrix_UB_12      0.012477
_diffrn_orient_matrix_UB_13      0.001175
_diffrn_orient_matrix_UB_21      -0.014294
_diffrn_orient_matrix_UB_22      -0.021294
_diffrn_orient_matrix_UB_23      0.022195
_diffrn_orient_matrix_UB_31      0.029251
_diffrn_orient_matrix_UB_32      0.037838
_diffrn_orient_matrix_UB_33      0.012103
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.420
_diffrn_reflns_Laue_measured_fraction_max 0.42
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            25807
_diffrn_reflns_point_group_measured_fraction_full 0.420
_diffrn_reflns_point_group_measured_fraction_max 0.42
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         18.923
_diffrn_reflns_theta_min         0.920
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.410
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             11008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     707
_refine_ls_number_reflns         5767
_refine_ls_number_restraints     756
_refine_ls_restrained_S_all      2.032
_refine_ls_R_factor_all          0.2626
_refine_ls_R_factor_gt           0.1990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5096
_refine_ls_wR_factor_ref         0.5480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3060
_reflns_number_total             5767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic6b00992_si_002.cif
_cod_data_source_block           c60fin
_cod_original_cell_volume        22357(12)
_cod_database_code               4348124
_shelxl_version_number           2013-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C21 \\sim C30 \\sim C22 \\sim C26 \\sim C34 \\sim C29 \\sim C35 \\sim C24 \\sim
C25 \\sim C27 \\sim C23 \\sim C33 \\sim C28 \\sim C41 \\sim C36 \\sim C43 \\sim
C65 \\sim C66 \\sim C44 \\sim C32 \\sim C38 \\sim C54 \\sim C50 \\sim C40 \\sim
C79 \\sim C42 \\sim C67 \\sim C64 \\sim C78 \\sim C63 \\sim C73 \\sim C39 \\sim
C76 \\sim C70 \\sim C80 \\sim C74 \\sim C68 \\sim C61 \\sim C45 \\sim C75 \\sim
C59 \\sim C47 \\sim C48 \\sim C71 \\sim C49 \\sim C31 \\sim C37 \\sim C60 \\sim
C55 \\sim C57 \\sim C77 \\sim C58 \\sim C62 \\sim C72 \\sim C52 \\sim C53 \\sim
C56 \\sim C46 \\sim C51 \\sim C69: within 1.7A with sigma of 0.022 and sigma
for terminal atoms of 0.05
C19 \\sim B1 \\sim Cl1 \\sim N1 \\sim C4 \\sim C1AA \\sim C2 \\sim N2 \\sim
C0AA \\sim C13 \\sim C12 \\sim S1 \\sim C14 \\sim S2 \\sim C11 \\sim C5 \\sim
H14 \\sim C15 \\sim H11 \\sim C6 \\sim C10 \\sim C16 \\sim C20 \\sim H6 \\sim
C7 \\sim C9 \\sim H10 \\sim H16 \\sim C17 \\sim H20 \\sim H7 \\sim C8 \\sim H9
\\sim H17 \\sim C18 \\sim H19 \\sim H8 \\sim H18: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
3. Others
 Fixed Sof: C101(0.5) C102(0.5) C103(0.5) C104(0.5) C105(0.5) C106(0.5)
 C107(0.5) C108(0.5) C109(0.5) C110(0.5) C111(0.5) C112(0.5) C113(0.5)
 C114(0.5) C115(0.5) C116(0.5) C117(0.5) C118(0.5) C119(0.5) C120(0.5)
 C121(0.5) C122(0.5) C123(0.5) C124(0.5) C125(0.5) C126(0.5) C127(0.5)
 C128(0.5) C129(0.5) C130(0.5) C131(0.5) C132(0.5) C133(0.5) C134(0.5)
 C135(0.5) C136(0.5) C137(0.5) C138(0.5) C139(0.5) C140(0.5) C141(0.5)
 C142(0.5) C143(0.5) C144(0.5) C145(0.5) C146(0.5) C147(0.5) C148(0.5)
 C149(0.5) C150(0.5) C151(0.5) C152(0.5) C153(0.5) C154(0.5) C155(0.5)
 C156(0.5) C157(0.5) C158(0.5) C159(0.5) C160(0.5) C201(0.16666) C202(0.16666)
 C203(0.16666) C204(0.16666) C205(0.16666) C206(0.16666) C207(0.16666)
 C208(0.16666) C209(0.16666) C210(0.16666) C211(0.16666) C212(0.16666)
 C213(0.16666) C214(0.16666) C215(0.16666) C216(0.16666) C217(0.16666)
 C218(0.16666) C219(0.16666) C220(0.16666) C221(0.16666) C222(0.16666)
 C223(0.16666) C224(0.16666) C225(0.16666) C226(0.16666) C227(0.16666)
 C228(0.16666) C229(0.16666) C230(0.16666) C231(0.16666) C232(0.16666)
 C233(0.16666) C234(0.16666) C235(0.16666) C236(0.16666) C237(0.16666)
 C238(0.16666) C239(0.16666) C240(0.16666) C241(0.16666) C242(0.16666)
 C243(0.16666) C244(0.16666) C245(0.16666) C246(0.16666) C247(0.16666)
 C248(0.16666) C249(0.16666) C250(0.16666) C251(0.16666) C252(0.16666)
 C253(0.16666) C254(0.16666) C255(0.16666) C256(0.16666) C257(0.16666)
 C258(0.16666) C259(0.16666) C260(0.16666) C301(0.16666) C302(0.16666)
 C303(0.16666) C304(0.16666) C305(0.16666) C306(0.16666) C307(0.16666)
 C308(0.16666) C309(0.16666) C310(0.16666) C311(0.16666) C312(0.16666)
 C313(0.16666) C314(0.16666) C315(0.16666) C316(0.16666) C317(0.16666)
 C318(0.16666) C319(0.16666) C320(0.16666) C321(0.16666) C322(0.16666)
 C323(0.16666) C324(0.16666) C325(0.16666) C326(0.16666) C327(0.16666)
 C328(0.16666) C329(0.16666) C330(0.16666) C331(0.16666) C332(0.16666)
 C333(0.16666) C334(0.16666) C335(0.16666) C336(0.16666) C337(0.16666)
 C338(0.16666) C339(0.16666) C340(0.16666) C341(0.16666) C342(0.16666)
 C343(0.16666) C344(0.16666) C345(0.16666) C346(0.16666) C347(0.16666)
 C348(0.16666) C349(0.16666) C350(0.16666) C351(0.16666) C352(0.16666)
 C353(0.16666) C354(0.16666) C355(0.16666) C356(0.16666) C357(0.16666)
 C358(0.16666) C359(0.16666) C360(0.16666) C401(0.16666) C402(0.16666)
 C403(0.16666) C404(0.16666) C405(0.16666) C406(0.16666) C407(0.16666)
 C408(0.16666) C409(0.16666) C410(0.16666) C411(0.16666) C412(0.16666)
 C413(0.16666) C414(0.16666) C415(0.16666) C416(0.16666) C417(0.16666)
 C418(0.16666) C419(0.16666) C420(0.16666) C421(0.16666) C422(0.16666)
 C423(0.16666) C424(0.16666) C425(0.16666) C426(0.16666) C427(0.16666)
 C428(0.16666) C429(0.16666) C430(0.16666) C431(0.16666) C432(0.16666)
 C433(0.16666) C434(0.16666) C435(0.16666) C436(0.16666) C437(0.16666)
 C438(0.16666) C439(0.16666) C440(0.16666) C441(0.16666) C442(0.16666)
 C443(0.16666) C444(0.16666) C445(0.16666) C446(0.16666) C447(0.16666)
 C448(0.16666) C449(0.16666) C450(0.16666) C451(0.16666) C452(0.16666)
 C453(0.16666) C454(0.16666) C455(0.16666) C456(0.16666) C457(0.16666)
 C458(0.16666) C459(0.16666) C460(0.16666) C270(0.25) C271(0.25) C273(0.25)
 C274(0.5) C276(0.25)
 Fixed Uiso: C137(0.1) C201(0.08) C202(0.08) C203(0.08) C204(0.08) C205(0.08)
 C206(0.08) C207(0.08) C208(0.08) C209(0.08) C210(0.08) C211(0.08) C212(0.08)
 C213(0.08) C214(0.08) C215(0.08) C216(0.08) C217(0.08) C218(0.08) C219(0.08)
 C220(0.08) C221(0.08) C222(0.08) C223(0.08) C224(0.08) C225(0.08) C226(0.08)
 C227(0.08) C228(0.08) C229(0.08) C230(0.08) C231(0.08) C232(0.08) C233(0.08)
 C234(0.08) C235(0.08) C236(0.08) C237(0.08) C238(0.08) C239(0.08) C240(0.08)
 C241(0.08) C242(0.08) C243(0.08) C244(0.08) C245(0.08) C246(0.08) C247(0.08)
 C248(0.08) C249(0.08) C250(0.08) C251(0.08) C252(0.08) C253(0.08) C254(0.08)
 C255(0.08) C256(0.08) C257(0.08) C258(0.08) C259(0.08) C260(0.08) C301(0.08)
 C302(0.08) C303(0.08) C304(0.08) C305(0.08) C306(0.08) C307(0.08) C308(0.08)
 C309(0.08) C310(0.08) C311(0.08) C312(0.08) C313(0.08) C314(0.08) C315(0.08)
 C316(0.08) C317(0.08) C318(0.08) C319(0.08) C320(0.08) C321(0.08) C322(0.08)
 C323(0.08) C324(0.08) C325(0.08) C326(0.08) C327(0.08) C328(0.08) C329(0.08)
 C330(0.08) C331(0.08) C332(0.08) C333(0.08) C334(0.08) C335(0.08) C336(0.08)
 C337(0.08) C338(0.08) C339(0.08) C340(0.08) C341(0.08) C342(0.08) C343(0.08)
 C344(0.08) C345(0.08) C346(0.08) C347(0.08) C348(0.08) C349(0.08) C350(0.08)
 C351(0.08) C352(0.08) C353(0.08) C354(0.08) C355(0.08) C356(0.08) C357(0.08)
 C358(0.08) C359(0.08) C360(0.08) C401(0.08) C402(0.08) C403(0.08) C404(0.08)
 C405(0.08) C406(0.08) C407(0.08) C408(0.08) C409(0.08) C410(0.08) C411(0.08)
 C412(0.08) C413(0.08) C414(0.08) C415(0.08) C416(0.08) C417(0.08) C418(0.08)
 C419(0.08) C420(0.08) C421(0.08) C422(0.08) C423(0.08) C424(0.08) C425(0.08)
 C426(0.08) C427(0.08) C428(0.08) C429(0.08) C430(0.08) C431(0.08) C432(0.08)
 C433(0.08) C434(0.08) C435(0.08) C436(0.08) C437(0.08) C438(0.08) C439(0.08)
 C440(0.08) C441(0.08) C442(0.08) C443(0.08) C444(0.08) C445(0.08) C446(0.08)
 C447(0.08) C448(0.08) C449(0.08) C450(0.08) C451(0.08) C452(0.08) C453(0.08)
 C454(0.08) C455(0.08) C456(0.08) C457(0.08) C458(0.08) C459(0.08) C460(0.08)
 C272(0.15) C270(0.15) C271(0.15) C273(0.15) C274(0.15) C276(0.15)
4.a Free rotating group:
 C101(C102,C103,C104,C105,C106,C107,C108,C109,C110,C111,C112,C113,C114,C115,
 C116,C117,C118,C119,C120,C121,C122,C123,C124,C125,C126,C127,C128,C129,C130,
 C131,C132,C133,C134,C135,C136,C137,C138,C139,C140,C141,C142,C143,C144,C145,
 C146,C147,C148,C149,C150,C151,C152,C153,C154,C155,C156,C157,C158,C159,C160),
 C201(C202,C203,C204,C205,C206,C207,C208,C209,C210,C211,C212,C213,C214,C215,
 C216,C217,C218,C219,C220,C221,C222,C223,C224,C225,C226,C227,C228,C229,C230,
 C231,C232,C233,C234,C235,C236,C237,C238,C239,C240,C241,C242,C243,C244,C245,
 C246,C247,C248,C249,C250,C251,C252,C253,C254,C255,C256,C257,C258,C259,C260),
 C301(C302,C303,C304,C305,C306,C307,C308,C309,C310,C311,C312,C313,C314,C315,
 C316,C317,C318,C319,C320,C321,C322,C323,C324,C325,C326,C327,C328,C329,C330,
 C331,C332,C333,C334,C335,C336,C337,C338,C339,C340,C341,C342,C343,C344,C345,
 C346,C347,C348,C349,C350,C351,C352,C353,C354,C355,C356,C357,C358,C359,C360),
 C401(C402,C403,C404,C405,C406,C407,C408,C409,C410,C411,C412,C413,C414,C415,
 C416,C417,C418,C419,C420,C421,C422,C423,C424,C425,C426,C427,C428,C429,C430,
 C431,C432,C433,C434,C435,C436,C437,C438,C439,C440,C441,C442,C443,C444,C445,
 C446,C447,C448,C449,C450,C451,C452,C453,C454,C455,C456,C457,C458,C459,C460)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
4.c Fitted pentagon refined as free rotating group:
 C21(C30,C34,C35,C22), C23(C24,C43,C67,C44), C25(C26,C27,C66,C65), C29(C28,C54,
 C50,C41), C33(C32,C40,C39,C38), C36(C79,C80,C74,C42), C48(C58,C71,C70,C76),
 C49(C47,C77,C46,C62), C51(C69,C53,C55,C56), C52(C37,C68,C31,C72), C78(C64,C61,
 C60,C45), C75(C63,C73,C59,C57)
4.d Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10), C11(C12,C0AA,C2,C13,C14), C15(C16,C17,C18,C19,C20),
 C272(C270,C271,C273,C274,C276)
;
_shelx_res_checksum              9597
_shelx_hkl_checksum              5868