3D supramolecular chiral crystal structures of radical anion salts of (−)-NDI-Δ and possible magnetic phase diagrams
Mizuno, Asato; Shuku, Yoshiaki; Suizu, Rie; Tsuchiizu, Masahisa; Awaga, Kunio; CrystEngComm 23 (2021) 5053–5059; doi:10.1039/D1CE00628B

data_7243061
_publ_section_title
;
 3D supramolecular chiral crystal structures of radical anion salts of
 (&#x2212;)-NDI-\D and possible magnetic phase diagrams
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              5053
_journal_page_last               5059
_journal_paper_doi               10.1039/D1CE00628B
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety
'2(C76 H72 N6 O21 Rb1.175), C78.077 H76.724 N6 O22.039 Rb1.268, C12 H24 O6 Rb0.472, 5.076(C4 H6 O3)'
_chemical_formula_sum            'C262.38 H275.18 N18 O85.27 Rb3.98'
_chemical_formula_weight         5385.37
_chemical_name_systematic        Rb@18-crown
_chemical_properties_physical    Air-sensitive
_space_group_crystal_system      tetragonal
_space_group_IT_number           80
_space_group_name_Hall           'I 4bw'
_space_group_name_H-M_alt        'I 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-02-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-02-26 deposited with the CCDC.	2021-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   57.3567(10)
_cell_length_b                   57.3567(10)
_cell_length_c                   29.2250(5)
_cell_measurement_reflns_used    564020
_cell_measurement_temperature    123
_cell_measurement_theta_max      3.02
_cell_measurement_theta_min      68.27
_cell_volume                     96144(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       69
_diffrn_reflns_limit_h_min       -69
_diffrn_reflns_limit_k_max       69
_diffrn_reflns_limit_k_min       -69
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            904631
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.082
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    0.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             22440
_exptl_crystal_recrystallization_method Electrocrystallization
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 16048 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3681
_refine_ls_number_reflns         87867
_refine_ls_number_restraints     5458
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1081P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1806
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                41551
_reflns_number_total             87867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00628b2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7243061.cif.'
_cod_original_cell_volume        96144(4)
_cod_database_code               7243061
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.794
_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. Restrained distances
 Rb7-O25 = Rb7-O35
 2.8 with sigma of 0.1
 C283-C282
 1.5 with sigma of 0.02
 C276-O95 = C276-O96
 1.4 with sigma of 0.02
 O85-C264
 1.4 with sigma of 0.02
 C282-O99 = O98-C281
 1.4 with sigma of 0.02
 C264-O86
 1.4 with sigma of 0.02
 O88-C268
 1.2 with sigma of 0.02
 C276-O94
 1.2 with sigma of 0.02
 O97-C280
 1.2 with sigma of 0.02
 C280-O99 = C280-O98
 1.4 with sigma of 0.02
 C268-O90 = C268-O89
 1.4 with sigma of 0.02
 C264-O84
 1.2 with sigma of 0.02
 C259-C258 = C257-C256 = C255-C254 = C253-C252 = C263-C262 = C261-C260
 1.5 with sigma of 0.02
 C251-C250 = C249-C248 = C247-C246 = C245-C244 = C243-C242 = C241-C240
 1.5 with sigma of 0.02
 C172-O55
 1.4 with sigma of 0.02
 C172-O56
 1.4 with sigma of 0.02
 O54-C172
 1.2 with sigma of 0.02
 C78-C79 \\sim C75-C76
 with sigma of 0.02
 O21-C78 \\sim O23-C75
 with sigma of 0.02
 O94-O96 \\sim O94-O95
 with sigma of 0.02
 O81-C259 \\sim O100-C257 \\sim O79-C255 \\sim O78-C253 \\sim O83-C263 \\sim
O82-C261 \\sim C260-O81 ~
 C258-O100 \\sim C256-O79 \\sim C254-O78 \\sim C252-O83 \\sim C262-O82
 with sigma of 0.02
 C74-C75 \\sim C77-C78
 with sigma of 0.02
 O22-C77 \\sim O20-C74
 with sigma of 0.02
 C278-O96 \\sim O95-C277
 with sigma of 0.02
 O97-O98 \\sim O97-O99
 with sigma of 0.02
 C260-C259 \\sim C258-C257 \\sim C256-C255 \\sim C254-C253 \\sim C252-C263
\\sim C262-C261
 with sigma of 0.02
 C254-C260 \\sim C255-C261 \\sim C252-C258 \\sim C253-C259 \\sim C262-C256
\\sim C263-C257
 with sigma of 0.02
 C250-O76 \\sim C248-O75 \\sim C246-O74 \\sim C244-O73 \\sim C242-O72 \\sim
C240-O77 \\sim O76-C249 ~
 O75-C247 \\sim O74-C245 \\sim O73-C243 \\sim O72-C241 \\sim O77-C251
 with sigma of 0.02
 C250-C249 \\sim C248-C247 \\sim C246-C245 \\sim C244-C243 \\sim C242-C241
\\sim C240-C251
 with sigma of 0.02
 Rb3-O82 \\sim Rb3-O81 \\sim Rb3-O100 \\sim Rb3-O79 \\sim Rb3-O78 \\sim Rb3-O83
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
Uanis(C276) = Uanis(O94)
4. Others
 Sof(C175)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C174)=Sof(H174)=Sof(C173)=
 Sof(H17D)=Sof(H17E)=Sof(C172)=Sof(O54)=Sof(O56)=Sof(O55)=FVAR(1)
 Sof(C171)=Sof(H17F)=Sof(H17G)=Sof(H17H)=Sof(C170)=Sof(H170)=Sof(C169)=
 Sof(H16Q)=Sof(H16R)=Sof(C168)=Sof(O51)=Sof(O53)=Sof(O52)=FVAR(2)
 Sof(C179)=Sof(H17I)=Sof(H17J)=Sof(H17K)=Sof(C178)=Sof(H178)=Sof(C177)=
 Sof(H17L)=Sof(H17M)=Sof(C176)=Sof(O57)=Sof(O59)=Sof(O58)=FVAR(3)
 Sof(O87)=1-FVAR(4)
 Sof(O84)=Sof(O86)=Sof(O85)=Sof(C266)=Sof(H266)=Sof(C265)=Sof(H26A)=Sof(H26B)=
 Sof(C264)=Sof(C267)=Sof(H26I)=Sof(H26J)=Sof(H26K)=FVAR(4)
 Sof(Rb4)=Sof(O74)=Sof(O73)=Sof(O72)=Sof(O77)=Sof(O76)=Sof(O75)=Sof(C244)=
 Sof(H24A)=Sof(H24B)=Sof(C245)=Sof(H24C)=Sof(H24D)=Sof(C248)=Sof(H24E)=
 Sof(H24F)=Sof(C249)=Sof(H24G)=Sof(H24H)=Sof(C242)=Sof(H24I)=Sof(H24J)=
 Sof(C243)=Sof(H24K)=Sof(H24L)=Sof(C241)=Sof(H24M)=Sof(H24N)=Sof(C246)=
 Sof(H24O)=Sof(H24P)=Sof(C240)=Sof(H24Q)=Sof(H24R)=Sof(C247)=Sof(H24S)=
 Sof(H24T)=Sof(C250)=Sof(H25O)=Sof(H25P)=Sof(C251)=Sof(H25Q)=Sof(H25R)=FVAR(5)
 Sof(O21)=Sof(C78)=Sof(H78)=Sof(O22)=Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(C79)=
 Sof(H79A)=Sof(H79B)=Sof(H79C)=1-FVAR(6)
 Sof(O20)=Sof(C76)=Sof(H76A)=Sof(H76B)=Sof(H76C)=Sof(C74)=Sof(H74A)=Sof(H74B)=
 Sof(O23)=Sof(C75)=Sof(H75)=FVAR(6)
 Sof(Rb3)=Sof(O82)=Sof(O81)=Sof(O100)=Sof(O79)=Sof(O78)=Sof(O83)=Sof(C260)=
 Sof(H26C)=Sof(H26D)=Sof(C253)=Sof(H25A)=Sof(H25B)=Sof(C261)=Sof(H26E)=
 Sof(H26F)=Sof(C255)=Sof(H25C)=Sof(H25D)=Sof(C256)=Sof(H25E)=Sof(H25F)=
 Sof(C257)=Sof(H25G)=Sof(H25H)=Sof(C254)=Sof(H25I)=Sof(H25J)=Sof(C262)=
 Sof(H26G)=Sof(H26H)=Sof(C259)=Sof(H25K)=Sof(H25L)=Sof(C258)=Sof(H25M)=
 Sof(H25N)=Sof(C252)=Sof(H25S)=Sof(H25T)=Sof(C263)=Sof(H26L)=Sof(H26M)=FVAR(7)
 Sof(O99)=Sof(C283)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C282)=Sof(H282)=Sof(O98)=
 Sof(O97)=Sof(C280)=Sof(C281)=Sof(H28D)=Sof(H28E)=FVAR(8)
 Sof(O96)=Sof(C276)=Sof(O94)=Sof(O95)=Sof(C277)=Sof(H27I)=Sof(H27J)=Sof(C278)=
 Sof(H278)=Sof(C279)=Sof(H27K)=Sof(H27L)=Sof(H27M)=FVAR(9)
 Sof(O93)=Sof(C274)=Sof(H274)=Sof(C275)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(O92)=
 Sof(C273)=Sof(H27D)=Sof(H27E)=Sof(C272)=Sof(O91)=FVAR(10)
 Sof(C269)=Sof(H26N)=Sof(H26O)=Sof(C270)=Sof(H270)=Sof(O88)=Sof(O90)=Sof(O89)=
 Sof(C271)=Sof(H27F)=Sof(H27G)=Sof(H27H)=Sof(C268)=FVAR(11)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C154(H154), C78(H78), C6(H6), C21(H21), C26(H26), C41(H41), C46(H46),
 C80(H80), C85(H85), C100(H100), C105(H105), C120(H120), C125(H125), C200(H200),
  C205(H205), C220(H220), C225(H225), C180(H180), C185(H185), C174(H174),
 C170(H170), C178(H178), C266(H266), C75(H75), C274(H274), C270(H270),
 C282(H282), C278(H278)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C153(H15D,H15E), C74(H74A,H74B), C4(H4A,H4B),
 C5(H5A,H5B), C22(H22I,H22J), C23(H23A,H23B), C24(H24U,H24V), C25(H25U,H25V),
 C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C61(H61A,H61B),
  C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B), C66(H66A,
 H66B), C67(H67A,H67B), C68(H68A,H68B), C69(H69A,H69B), C70(H70A,H70B),
 C71(H71A,H71B), C72(H72A,H72B), C81(H81A,H81B), C82(H82A,H82B), C83(H83A,H83B),
  C84(H84A,H84B), C101(H10A,H10B), C102(H10C,H10D), C103(H10E,H10F), C104(H10G,
 H10H), C121(H12A,H12B), C122(H12C,H12D), C123(H12E,H12F), C124(H12G,H12H),
 C140(H14A,H14B), C141(H14C,H14D), C142(H14E,H14F), C143(H14G,H14H), C144(H14I,
 H14J), C145(H14K,H14L), C146(H14M,H14N), C147(H14O,H14P), C148(H14Q,H14R),
 C149(H14S,H14T), C150(H15F,H15G), C151(H15H,H15I), C201(H20A,H20B), C202(H20C,
 H20D), C203(H20E,H20F), C204(H20G,H20H), C221(H22A,H22B), C222(H22C,H22D),
 C223(H22E,H22F), C224(H22G,H22H), C181(H18A,H18B), C182(H18C,H18D), C183(H18E,
 H18F), C184(H18G,H18H), C158(H15J,H15K), C159(H15L,H15M), C160(H16A,H16B),
 C161(H16C,H16D), C162(H16E,H16F), C163(H16G,H16H), C164(H16I,H16J), C165(H16K,
 H16L), C166(H16M,H16N), C167(H16O,H16P), C156(H15N,H15O), C157(H15P,H15Q),
 C173(H17D,H17E), C169(H16Q,H16R), C177(H17L,H17M), C265(H26A,H26B), C260(H26C,
 H26D), C253(H25A,H25B), C261(H26E,H26F), C255(H25C,H25D), C256(H25E,H25F),
 C257(H25G,H25H), C254(H25I,H25J), C262(H26G,H26H), C259(H25K,H25L), C258(H25M,
 H25N), C244(H24A,H24B), C245(H24C,H24D), C248(H24E,H24F), C249(H24G,H24H),
 C242(H24I,H24J), C243(H24K,H24L), C241(H24M,H24N), C246(H24O,H24P), C240(H24Q,
 H24R), C247(H24S,H24T), C250(H25O,H25P), C251(H25Q,H25R), C77(H77A,H77B),
 C252(H25S,H25T), C263(H26L,H26M), C269(H26N,H26O), C273(H27D,H27E), C281(H28D,
 H28E), C277(H27I,H27J)
5.c Me refined with riding coordinates:
 C76(H76A,H76B,H76C), C175(H17A,H17B,H17C), C79(H79A,H79B,H79C), C271(H27F,
 H27G,H27H)
5.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C16(H16), C31(H31), C33(H33), C34(H34),
 C36(H36), C51(H51), C53(H53), C54(H54), C56(H56), C90(H90), C92(H92), C93(H93),
  C95(H95), C110(H110), C112(H112), C113(H113), C115(H115), C130(H130),
 C132(H132), C133(H133), C135(H135), C210(H210), C212(H212), C213(H213),
 C215(H215), C230(H230), C232(H232), C233(H233), C235(H235), C190(H190),
 C192(H192), C193(H193), C195(H195)
5.e Idealised Me refined as rotating group:
 C155(H15A,H15B,H15C), C171(H17F,H17G,H17H), C179(H17I,H17J,H17K), C267(H26I,
 H26J,H26K), C275(H27A,H27B,H27C), C283(H28A,H28B,H28C), C279(H27K,H27L,H27M)
;
_shelx_res_checksum              636
_shelx_hkl_checksum              62277
_shelx_fab_checksum              36692
_olex2_submission_special_instructions 'No special instructions were received'