Chiral biphenanthrene-diol-based lanthanide cubanes.
Qin, Haowei; Wang, Tingting; Feng, Tingting; Zhu, Zhenhua; Ying, Xu; Zhang, Peng; Tang, Jinkui; Chemical communications (Cambridge, England) 62 (2026) 6591–6595; doi:10.1039/d6cc00777e

data_7135559
_publ_section_title
;
 Chiral biphenanthrene-diol-based lanthanide cubanes.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6591
_journal_page_last               6595
_journal_paper_doi               10.1039/d6cc00777e
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration rmad
_chemical_formula_moiety
'C168 H100 Er4 O16, 4(C5 H14 N3), C H2 Cl2, 6[CH2Cl2], 1[H2O]'
_chemical_formula_sum            'C195 H172 Cl14 Er4 N12 O17'
_chemical_formula_weight         4120.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2026-01-04 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5439(6)
_cell_length_b                   28.4744(11)
_cell_length_c                   35.6072(14)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    180.00
_cell_measurement_theta_max      24.520
_cell_measurement_theta_min      2.322
_cell_volume                     17787.6(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      180.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            100808
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.085
_diffrn_reflns_theta_max         25.085
_diffrn_reflns_theta_min         2.322
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.146
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0895 before and 0.0796 after correction.
The Ratio of minimum to maximum transmission is 0.7917.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       block
_exptl_crystal_F_000             8288
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.807
_refine_diff_density_min         -1.256
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Flack x determined using 8946 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1961
_refine_ls_number_reflns         31373
_refine_ls_number_restraints     1486
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0501P)^2^+38.0049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                24144
_reflns_number_total             31373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00777e2.cif
_cod_data_source_block           123_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7135556--7135559.cif.'
_cod_database_code               7135559
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.753
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-C1B
 1.78 with sigma of 0.02
 Cl1-C1B
 1.77 with sigma of 0.02
 Cl2-C1B = Cl1-C1B
 1.771 with sigma of 0.01
 Cl2-Cl1
 2.916 with sigma of 0.03
 Cl2-Cl1
 2.92 with sigma of 0.04
 N10-C178 \\sim N10-C160 \\sim N7-C179 \\sim N7-C151
 with sigma of 0.02
 N10-C153 \\sim N7-C153
 with sigma of 0.02
3. Restrained planarity
 N2, N7, N10, C153
 with sigma of 0.1
 N3, N11, N12, C186
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57
\\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65
\\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C73
\\sim C74 \\sim C75 \\sim C76 \\sim C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81
\\sim C82 \\sim C83 \\sim C84 \\sim C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89
\\sim C90 \\sim C91 \\sim C92 \\sim C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97
\\sim C98 \\sim C99 \\sim C100 \\sim C101 \\sim C102 \\sim C103 \\sim C104
\\sim C105 \\sim C106 \\sim C107 \\sim C108 \\sim C109 \\sim C110 \\sim C111
\\sim C112 \\sim C113 \\sim C114 \\sim C115 \\sim C116 \\sim C117 \\sim C118
\\sim C119 \\sim C120 \\sim C121 \\sim C122 \\sim C123 \\sim C124 \\sim C125
\\sim C126 \\sim C128 \\sim C129 \\sim C130 \\sim C131 \\sim C132 \\sim C133
\\sim C134 \\sim C135 \\sim C136 \\sim C137 \\sim C139 \\sim C141 \\sim C143
\\sim C144 \\sim C145 \\sim C146 \\sim C147 \\sim C148 \\sim C149 \\sim C150
\\sim C152 \\sim C154 \\sim C155 \\sim C156 \\sim C158 \\sim C159 \\sim C161
\\sim C162 \\sim C164 \\sim C165 \\sim C166 \\sim C167 \\sim C168 \\sim C169
\\sim C170 \\sim C171 \\sim C172 \\sim C173 \\sim C174 \\sim C175 \\sim C176
\\sim C177 \\sim C127 \\sim C138 \\sim C140 \\sim C142 \\sim C163 \\sim C151
\\sim C153 \\sim C160 \\sim C178 \\sim C179 \\sim C185 \\sim C186 \\sim C187
\\sim C188 \\sim C189 \\sim C180 \\sim C181 \\sim C182 \\sim C183 \\sim C184:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
N2 \\sim N7 \\sim N10 \\sim C151 \\sim C153 \\sim C160 \\sim C178 \\sim C179:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
N4 \\sim N8 \\sim N9 \\sim C180 \\sim C181 \\sim C182 \\sim C183 \\sim C184:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Cl1 \\sim Cl2 \\sim C1B: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
N3 \\sim N11 \\sim N12 \\sim C185 \\sim C186 \\sim C187 \\sim C188 \\sim C189:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57
\\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65
\\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C73
\\sim C74 \\sim C75 \\sim C76 \\sim C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81
\\sim C82 \\sim C83 \\sim C84 \\sim C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89
\\sim C90 \\sim C91 \\sim C92 \\sim C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97
\\sim C98 \\sim C99 \\sim C100 \\sim C101 \\sim C102 \\sim C103 \\sim C104
\\sim C105 \\sim C106 \\sim C107 \\sim C108 \\sim C109 \\sim C110 \\sim C111
\\sim C112 \\sim C113 \\sim C114 \\sim C115 \\sim C116 \\sim C117 \\sim C118
\\sim C119 \\sim C120 \\sim C121 \\sim C122 \\sim C123 \\sim C124 \\sim C125
\\sim C126 \\sim C128 \\sim C129 \\sim C130 \\sim C131 \\sim C132 \\sim C133
\\sim C134 \\sim C135 \\sim C136 \\sim C137 \\sim C139 \\sim C141 \\sim C143
\\sim C144 \\sim C145 \\sim C146 \\sim C147 \\sim C148 \\sim C149 \\sim C150
\\sim C152 \\sim C154 \\sim C155 \\sim C156 \\sim C158 \\sim C159 \\sim C161
\\sim C162 \\sim C164 \\sim C165 \\sim C166 \\sim C167 \\sim C168 \\sim C169
\\sim C170 \\sim C171 \\sim C172 \\sim C173 \\sim C174 \\sim C175 \\sim C176
\\sim C177 \\sim C1B \\sim C127 \\sim C138 \\sim C140 \\sim C142 \\sim C163
\\sim C151 \\sim C153 \\sim C160 \\sim C178 \\sim C179 \\sim C185 \\sim C186
\\sim C187 \\sim C188 \\sim C189 \\sim C180 \\sim C181 \\sim C182 \\sim C183
\\sim C184: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Uanis(C146) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C139) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C168) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C171) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C170) \\sim Ueq, Uanis(C169) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C153) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 N3, N11, N12, C185, C186, C187, C188, C189
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N2, N7, N10, C151, C153, C160, C178, C179
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 Cl1, Cl2, C1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, H2A, H2B, N7, N10, C151, H15A, H15B, H15C, C153, C160, H16A, H16B, H16C,
 C178, H17A, H17B, H17C, C179, H17D, H17E, H17F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N3, H3A, H3B, N11, N12, C185, H18M, H18N, H18O, C186, C187, H18P, H18Q, H18R,
 C188, H18S, H18T, H18U, C189, H18V, H18W, H18X
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6.a Everything fixed:
 O1, H1, O2, H2, O3, H3, O4, H4
6.b Riding coordinates:
 C178(H17A,H17B,H17C), C185(H18M,H18N,H18O), C189(H18V,H18W,H18X), C181(H18A,
 H18B,H18C)
6.c Rotating group:
 N1(H1B,H1C)
6.d Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB)
6.e Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C11(H11), C16(H16), C17(H17), C20(H20), C24(H24), C31(H31),
 C32(H32), C33(H33), C35(H35), C43(H43), C44(H44), C48(H48), C55(H55), C56(H56),
  C57(H57), C58(H58), C62(H62), C63(H63), C65(H65), C67(H67), C71(H71),
 C77(H77), C78(H78), C80(H80), C81(H81), C84(H84), C85(H85), C86(H86), C88(H88),
  C89(H89), C90(H90), C91(H91), C92(H92), C94(H94), C96(H96), C97(H97),
 C98(H98), C99(H99), C100(H100), C102(H102), C103(H103), C105(H105), C106(H106),
  C107(H107), C108(H108), C110(H110), C111(H111), C112(H112), C113(H113),
 C114(H114), C115(H115), C116(H116), C117(H117), C118(H118), C119(H119),
 C120(H120), C122(H122), C123(H123), C124(H124), C126(H126), C128(H128),
 C130(H130), C131(H131), C132(H132), C133(H133), C134(H134), C135(H135),
 C136(H136), C137(H137), C139(H139), C141(H141), C143(H143), C144(H144),
 C148(H148), C149(H149), C146(H146), C147(H147), C150(H150), C152(H152),
 C154(H154), C155(H155), C159(H159), C161(H161), C162(H162), C164(H164),
 C165(H165), C166(H166), C167(H167), C168(H168), C171(H171), C172(H172),
 C173(H173), C174(H174), C177(H177)
6.f Fitted hexagon refined as free rotating group:
 C148(C149,C146,C15,C14,C147), C169(C170,C171,C172,C173,C174)
6.g X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B)
6.h Idealised Me refined as rotating group:
 C138(H13A,H13B,H13C), C140(H14A,H14B,H14C), C142(H14D,H14E,H14F), C163(H16D,
 H16E,H16F), C151(H15A,H15B,H15C), C160(H16A,H16B,H16C), C179(H17D,H17E,H17F),
 C187(H18P,H18Q,H18R), C188(H18S,H18T,H18U), C182(H18D,H18E,H18F), C183(H18G,
 H18H,H18I), C184(H18J,H18K,H18L)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 1024 electrons were 
found in a volume of 3920\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
6[CH2Cl2], 1[H2O] per Asymmetric Unit 
which account for 1048 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'