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_7135556
_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_formula_moiety
'C168 H100 Dy4 O16, 3(C H2 Cl2), 4(C5 H14 N3), 4[CH2Cl2], 1.5[H2O]'
_chemical_formula_sum            'C195 H173 Cl14 Dy4 N12 O17.5'
_chemical_formula_weight         4110.74
_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                   17.7008(6)
_cell_length_b                   28.3765(12)
_cell_length_c                   36.0385(15)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    180.00
_cell_measurement_theta_max      24.511
_cell_measurement_theta_min      2.432
_cell_volume                     18101.7(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  0.1205
_diffrn_reflns_av_unetI/netI     0.1270
_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       -21
_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            100598
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.061
_diffrn_reflns_theta_max         25.061
_diffrn_reflns_theta_min         2.301
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.906
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5979
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0947 before and 0.0839 after correction.
The Ratio of minimum to maximum transmission is 0.8023.
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    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             8276
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 7377 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2028
_refine_ls_number_reflns         31806
_refine_ls_number_restraints     599
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0535P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                22454
_reflns_number_total             31806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00777e2.cif
_cod_data_source_block           123
_cod_depositor_comments
'Adding full bibliography for 7135556--7135559.cif.'
_cod_original_formula_sum        'C195 H173 Cl14 Dy4 N12 O17.50'
_cod_database_code               7135556
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.832
_shelx_estimated_absorpt_t_min   0.776
_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
 N5-C47 = N6-C47 = N2-C47
 1.3 with sigma of 0.02
 Cl3-C189
 1.78 with sigma of 0.02
 Cl4-C189
 1.77 with sigma of 0.02
 Cl3-C189 = Cl4-C189
 1.771 with sigma of 0.01
 Cl3-Cl4
 2.916 with sigma of 0.03
 Cl5-C95
 1.78 with sigma of 0.02
 Cl6-C95
 1.77 with sigma of 0.02
 Cl5-C95 = Cl6-C95
 1.771 with sigma of 0.01
 Cl5-Cl6
 2.916 with sigma of 0.03
 Cl3-Cl4
 2.92 with sigma of 0.04
 Cl5-Cl6
 2.92 with sigma of 0.04
 N5-C187 \\sim N5-C93 \\sim N6-C185 \\sim N6-C23
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C5 \\sim C22 \\sim C41 \\sim C45 \\sim C81 \\sim C91 \\sim C92 \\sim C151 \\sim
C159 \\sim C161 \\sim C163 \\sim C165 \\sim C181 \\sim C183: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
N1 \\sim N7 \\sim N10 \\sim C11 \\sim C77 \\sim C139 \\sim C155 \\sim C177:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C27 \\sim C28 \\sim C37 \\sim C44 \\sim C49 \\sim C53 \\sim C67 \\sim C71 \\sim
C88 \\sim C94 \\sim C114 \\sim C133 \\sim C152 \\sim C162: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
Cl3 \\sim Cl4 \\sim C189: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Cl5 \\sim Cl6 \\sim C95: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C17 \\sim C33 \\sim C57 \\sim C59 \\sim C78 \\sim C83 \\sim C103 \\sim C105
\\sim C164 \\sim C173: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C30 \\sim C66 \\sim C102 \\sim C108 \\sim C120 \\sim C126: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
C12 \\sim C38 \\sim C82 \\sim C96 \\sim C150: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C2 \\sim C13 \\sim C26 \\sim C31 \\sim C39 \\sim C70 \\sim C129 \\sim C134
\\sim C169 \\sim C174: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(C159) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C183) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C41) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N1, H1A, H1B, N7, N10, C11, H11A, H11B, H11C, C77, H77A, H77B, H77C, C139,
 C155, H15A, H15B, H15C, C177, H17A, H17B, H17C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N2, N5, N6, C23, C47, C93, C185, C187
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl3, Cl4, C189
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl5, Cl6, C95
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Everything fixed:
 O1, H1, O2, H2, O3, H3, O4, H4
5.b Riding coordinates:
 C111(H11D,H11E,H11F), C185(H18A,H18B,H18C), C187(H18D,H18E,H18F)
5.c Rotating group:
 N1(H1A,H1B)
5.d Secondary CH2 refined with riding coordinates:
 C95(H95A,H95B), C157(H15D,H15E), C189(H18G,H18H)
5.e Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C4(H4A), C7(H7), C8(H8), C15(H15), C17(H17), C18(H18),
 C21(H21), C25(H25), C27(H27), C29(H29), C31(H31), C33(H33), C36(H36), C37(H37),
  C39(H39), C45(H45), C51(H51), C52(H52), C53(H53), C55(H55), C56(H56),
 C58(H58), C59(H59), C61(H61), C62(H62), C67(H67), C68(H68), C69(H69), C71(H71),
  C74(H74), C75(H75), C79(H79), C83(H83), C85(H85), C89(H89), C91(H91),
 C99(H99), C101(H101), C102(H102), C103(H103), C104(H104), C107(H107),
 C109(H109), C110(H110), C112(H112), C113(H113), C114(H114), C115(H115),
 C117(H117), C118(H118), C119(H119), C123(H123), C125(H125), C126(H126),
 C127(H127), C129(H129), C130(H130), C131(H131), C133(H133), C134(H134),
 C135(H135), C136(H136), C138(H138), C140(H140), C141(H141), C143(H143),
 C144(H144), C146(H146), C148(H148), C151(H151), C153(H153), C154(H154),
 C156(H156), C158(H158), C159(H159), C41(H41), C162(H162), C165(H165),
 C168(H168), C169(H169), C170(H170), C171(H171), C173(H173), C175(H175),
 C178(H178), C179(H179), C180(H180), C181(H181), C182(H182), C183(H183),
 C184(H184), C186(H186), C188(H188), C190(H190)
5.f Fitted hexagon refined as free rotating group:
 C159(C5,C161,C81,C163,C41)
5.g X=CH2 refined with riding coordinates:
 N2(H2B,H2C), N3(H3B,H3C), N4(H4B,H4C)
5.h Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C23(H23A,H23B,H23C), C43(H43A,H43B,
 H43C), C65(H65A,H65B,H65C), C73(H73A,H73B,H73C), C77(H77A,H77B,H77C), C93(H93A,
 H93B,H93C), C145(H14A,H14B,H14C), C147(H14D,H14E,H14F), C149(H14G,H14H,H14I),
 C155(H15A,H15B,H15C), C177(H17A,H17B,H17C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 780 electrons were 
found in a volume of 3320\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
4[CH2Cl2] per Asymmetric Unit 
which account for 672 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'