Isolating the ring-redox states of boron sub-phthalocyanines.
Zhou, Wen; McKearney, Declan; Okada, Yusuke; Kobayashi, Nagao; Leznoff, Daniel B.; Chemical communications (Cambridge, England) 61 (2025) 3832–3835; doi:10.1039/d4cc06727d

data_7134252
_publ_section_title
;
 Isolating the ring-redox states of boron sub-phthalocyanines.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3832
_journal_page_last               3835
_journal_paper_doi               10.1039/d4cc06727d
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety
'3(C76.5 H41 B3 K2 N18 O2.5), 3(C76 H44.5 B3 K2 N18 O2), C15 H15 K O5.5, C13.5 K O6, C12 H4.5 K1 O6, C18.5 H15 K2 O8, C10.5 H3 K O6'
_chemical_formula_sum            'C527 H294 B18 K18 N108 O45'
_chemical_formula_weight         9757.06
_space_group_crystal_system      trigonal
_space_group_IT_number           143
_space_group_name_Hall           'P 3'
_space_group_name_H-M_alt        'P 3'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-11-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-26 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            1
_cell_length_a                   27.0235(7)
_cell_length_b                   27.0235(7)
_cell_length_c                   21.5015(13)
_cell_measurement_reflns_used    9570
_cell_measurement_temperature    150.03
_cell_measurement_theta_max      67.08
_cell_measurement_theta_min      3.27
_cell_volume                     13598.2(10)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.03
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1215
_diffrn_reflns_av_unetI/netI     0.1417
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            73113
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.765
_diffrn_reflns_theta_min         2.791
_exptl_absorpt_coefficient_mu    1.838
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1265 before and 0.0886 after correction.
The Ratio of minimum to maximum transmission is 0.7252.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       Block
_exptl_crystal_F_000             5004
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.066
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.270
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2952
_refine_ls_number_reflns         27856
_refine_ls_number_restraints     6917
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.2500
_refine_ls_R_factor_gt           0.1432
_refine_ls_shift/su_max          0.006
_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          0.3614
_refine_ls_wR_factor_ref         0.4416
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.684
_reflns_Friedel_fraction_max     0.658
_reflns_number_gt                12196
_reflns_number_total             27856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06727d2.cif
_cod_data_source_block           cu_zwsupcbkc8_0m_b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134249--7134252.cif.
;
_cod_original_cell_volume        13598.2(11)
_cod_database_code               7134252
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.703
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.50(4)
 0.50(4)
2. 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, All C(H,H,H,H,H,H) groups
3. Restrained distances
 O8-C52 = C52-O18 = C183-C182 = O11-C161 = C166-C164 = O25-C309 = C302-O30 =
 C308-O25
 1.5 with sigma of 0.02
 C321-O15 = O15-C327 = C318-O14 = C162-O3 = C325-O17 = C331-C332 = C332-O20 =
 O1-C166
 1.5 with sigma of 0.02
 C308-C307 = C307-C319 = C184-O23 = O18-C356 = O1-C357 = O20-C359 = C321-C320
 1.5 with sigma of 0.02
 C175-C173 = C329-C360 = O28-C361 = C331-O16 = O29-C301 = O31-C367 = O31-C366
 1.5 with sigma of 0.02
 C176-O27 = C366-C184 = C360-O28 = O9-C320 = C303-C301 = C330-O4 = C325-C322
 1.5 with sigma of 0.02
 C361-C326 = O19-O28
 2 with sigma of 0.02
 O15-K11
 3.371 with sigma of 0.01
 C329-K7
 3.223 with sigma of 0.01
 C359-K6
 3.809 with sigma of 0.01
 C332-K6
 2.626 with sigma of 0.01
4. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
6. Others
 Sof(N35)=Sof(N36)=Sof(C198)=Sof(C199)=Sof(C200)=Sof(C201)=Sof(C202)=Sof(H202)=
 Sof(C203)=Sof(H203)=Sof(C204)=Sof(H204)=Sof(C205)=Sof(H205)=1-FVAR(1)
 Sof(N16)=Sof(N30)=Sof(C54)=Sof(C56)=Sof(C57)=Sof(C58)=Sof(C77)=Sof(H77)=
 Sof(C78)=Sof(H78)=Sof(C79)=Sof(H79)=Sof(C80)=Sof(H80)=FVAR(1)
 Sof(N39)=Sof(C197)=Sof(C206)=Sof(C207)=Sof(C208)=Sof(C209)=Sof(H209)=
 Sof(C210)=Sof(H210)=Sof(C211)=Sof(H211)=Sof(C212)=Sof(H212)=1-FVAR(2)
 Sof(N13)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=FVAR(2)
 Sof(C213)=Sof(C214)=Sof(H214)=Sof(C215)=Sof(H215)=Sof(C216)=Sof(H216)=
 Sof(C217)=Sof(H217)=Sof(C218)=1-FVAR(3)
 Sof(C40)=Sof(C41)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=
 Sof(C46)=Sof(H46)=FVAR(3)
 Sof(N37)=Sof(N38)=Sof(C219)=Sof(C221)=Sof(C222)=Sof(H222)=Sof(C223)=Sof(H223)=
 Sof(C224)=Sof(H224)=Sof(C47)=Sof(H47)=Sof(C73)=1-FVAR(4)
 Sof(N12)=Sof(N14)=Sof(C236)=Sof(H236)=Sof(C48)=Sof(C49)=Sof(C50)=Sof(C74)=
 Sof(H74)=Sof(C75)=Sof(H75)=Sof(C76)=Sof(H76)=FVAR(4)
 Sof(C225)=Sof(H225)=Sof(C226)=Sof(H226)=Sof(C227)=Sof(H227)=Sof(C228)=
 Sof(H228)=1-FVAR(5)
 Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=Sof(C39)=Sof(H39)=FVAR(5)
 Sof(C229)=Sof(C230)=Sof(H230)=Sof(C231)=Sof(H231)=Sof(C232)=Sof(H232)=
 Sof(C233)=Sof(H233)=Sof(C234)=1-FVAR(6)
 Sof(C116)=Sof(C117)=Sof(H117)=Sof(C118)=Sof(H118)=Sof(C119)=Sof(H119)=
 Sof(C120)=Sof(H120)=Sof(C121)=FVAR(6)
 Sof(K11)=Sof(K12)=Sof(K13)=0.33333*(1-FVAR(8))
 Sof(K7)=Sof(K10)=Sof(K9)=0.33333*FVAR(8)
 Fixed Sof: O1(0.166667) O2(0.5) O3(0.166667) O4(0.5) C330(0.5) H33A(0.5)
 H33B(0.5) C331(0.5) C332(0.5) C333(0.5) C334(0.5) C355(0.5) C356(0.5)
 C357(0.5) O6(0.5) O7(0.5) O8(0.5) O9(0.5) O10(0.5) O11(0.5) O12(0.5) O13(0.5)
 C358(0.5) C359(0.5) O14(0.5) O15(0.5) O16(0.5) O17(0.5) O18(0.5) O19(0.5)
 O20(0.5) O21(0.5) O22(0.5) O23(0.5) O24(0.5) O25(0.5) O26(0.5) O27(0.5)
 O28(0.5) O29(0.5) O30(0.5) O31(0.166667) C51(0.5) C52(0.5) C70(0.5) H70A(0.5)
 H70B(0.5) H70C(0.5) C72(0.5) H72A(0.5) H72B(0.5) C81(0.5) H81A(0.5) H81B(0.5)
 H81C(0.5) C115(0.5) H11A(0.5) H11B(0.5) C161(0.5) H16A(0.5) H16B(0.5)
 C162(0.5) C164(0.5) C166(0.5) C168(0.5) H16E(0.5) H16F(0.5) C169(0.5)
 H16G(0.5) H16H(0.5) C173(0.5) C175(0.5) C176(0.5) C180(0.5) C181(0.5)
 H18A(0.5) H18B(0.5) H18C(0.5) C182(0.5) H18D(0.5) H18E(0.5) C183(0.5)
 H18F(0.5) H18G(0.5) C184(0.5) C185(0.5) H18H(0.5) H18I(0.5) H18J(0.5)
 C300(0.5) H30A(0.5) H30B(0.5) H30C(0.5) C301(0.5) H30D(0.5) H30E(0.5)
 C302(0.5) H30F(0.5) H30G(0.5) H30H(0.5) C303(0.5) H30I(0.5) H30J(0.5)
 C304(0.5) C305(0.5) H30K(0.5) H30L(0.5) H30M(0.5) C306(0.5) C307(0.5)
 C308(0.5) C309(0.5) C311(0.5) C312(0.5) H31A(0.5) H31B(0.5) C313(0.5)
 C318(0.5) C319(0.5) C320(0.5) C321(0.5) C322(0.5) H32G(0.5) H32H(0.5)
 C323(0.5) C324(0.5) C325(0.5) C326(0.5) C327(0.5) H32A(0.25) H32B(0.25)
 H32C(0.25) H32D(0.25) H32E(0.25) H32F(0.25) C329(0.5) C360(0.5) C361(0.5)
 C362(0.5) C366(0.5) C367(0.166667)
7.a Secondary CH2 refined with riding coordinates:
 C330(H33A,H33B), C72(H72A,H72B), C115(H11A,H11B), C161(H16A,H16B), C167(H16C,
 H16D), C168(H16E,H16F), C169(H16G,H16H), C182(H18D,H18E), C183(H18F,H18G),
 C301(H30D,H30E), C303(H30I,H30J), C312(H31A,H31B), C322(H32G,H32H)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C36(H36), C37(H37), C38(H38), C39(H39),
  C43(H43), C44(H44), C45(H45), C46(H46), C61(H61), C62(H62), C63(H63),
 C64(H64), C65(H65), C66(H66), C67(H67), C68(H68), C236(H236), C74(H74),
 C75(H75), C76(H76), C77(H77), C78(H78), C79(H79), C80(H80), C83(H83), C84(H84),
  C85(H85), C86(H86), C98(H98), C99(H99), C100(H100), C101(H101), C102(H102),
 C103(H103), C104(H104), C105(H105), C117(H117), C118(H118), C119(H119),
 C120(H120), C130(H130), C131(H131), C132(H132), C133(H133), C139(H139),
 C140(H140), C141(H141), C142(H142), C145(H145), C146(H146), C147(H147),
 C148(H148), C152(H152), C153(H153), C154(H154), C155(H155), C156(H156),
 C157(H157), C158(H158), C159(H159), C230(H230), C231(H231), C232(H232),
 C233(H233), C225(H225), C226(H226), C227(H227), C228(H228), C222(H222),
 C223(H223), C224(H224), C47(H47), C214(H214), C215(H215), C216(H216),
 C217(H217), C209(H209), C210(H210), C211(H211), C212(H212), C202(H202),
 C203(H203), C204(H204), C205(H205)
7.c Fitted hexagon refined as free rotating group:
 C221(C222,C223,C224,C47,C73)
7.d Disordered Me refined with riding coordinates:
 C327(H32A,H32B,H32C,H32D,H32E,H32F)
7.e Idealised Me refined as rotating group:
 C70(H70A,H70B,H70C), C81(H81A,H81B,H81C), C181(H18A,H18B,H18C), C185(H18H,
 H18I,H18J), C300(H30A,H30B,H30C), C302(H30F,H30G,H30H), C305(H30K,H30L,H30M)
;
_shelx_res_checksum              60382
_shelx_hkl_checksum              82324
_olex2_submission_special_instructions 'No special instructions were received'