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_7135558
_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, 2(C H2 Cl2), 4(C5 H14 N3), 4[CH2Cl2], 1.5[H2O]'
_chemical_formula_sum            'C194 H171 Cl12 Er4 N12 O17.5'
_chemical_formula_weight         4044.86
_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     iterative
_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                   17.4169(4)
_cell_length_b                   28.5045(8)
_cell_length_c                   35.6754(11)
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    180.00
_cell_measurement_theta_max      24.858
_cell_measurement_theta_min      2.393
_cell_volume                     17711.4(8)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_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  0.0663
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_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            100616
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.077
_diffrn_reflns_theta_max         25.077
_diffrn_reflns_theta_min         2.193
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.125
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5043
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1071 before and 0.0760 after correction.
The Ratio of minimum to maximum transmission is 0.6767.
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    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             8140
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.053
_refine_diff_density_min         -1.617
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details
;
 Flack x determined using 10100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1976
_refine_ls_number_reflns         31294
_refine_ls_number_restraints     1366
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+97.5221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                24993
_reflns_number_total             31294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00777e2.cif
_cod_data_source_block           erno3
_cod_depositor_comments
'Adding full bibliography for 7135556--7135559.cif.'
_cod_original_formula_sum        'C194 H171 Cl12 Er4 N12 O17.50'
_cod_database_code               7135558
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.755
_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
 C190-C189
 3 with sigma of 0.04
 C190-C187
 2.5 with sigma of 0.04
 N1-C188
 2.623 with sigma of 0.04
 N12-C165 \\sim N11-C165
 with sigma of 0.02
 N8-C186 \\sim N1-C186 \\sim N9-C186
 with sigma of 0.02
 N8-N9 \\sim N9-N1
 with sigma of 0.02
 N9-C186 \\sim N9-C187 \\sim N9-C190
 with sigma of 0.02
 N8-C189 \\sim N8-C186 \\sim N8-C188
 with sigma of 0.02
 N1-C187 \\sim N1-C188
 with sigma of 0.02
3. Restrained planarity
 N1, N8, N9, 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 C105
\\sim C106 \\sim C107 \\sim C108 \\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 C124 \\sim C125 \\sim C126 \\sim C128 \\sim C130
\\sim C131 \\sim C132 \\sim C134 \\sim C135 \\sim C136 \\sim C137 \\sim C140
\\sim C141 \\sim C142 \\sim C144 \\sim C147 \\sim C148 \\sim C149 \\sim C150
\\sim C151 \\sim C152 \\sim C154 \\sim C155 \\sim C156 \\sim C157 \\sim C158
\\sim C160 \\sim C161 \\sim C162 \\sim C163 \\sim C164 \\sim C168 \\sim C169
\\sim C170 \\sim C171 \\sim C172 \\sim C173 \\sim C174 \\sim C175 \\sim C176
\\sim C177 \\sim C178 \\sim C179 \\sim C180 \\sim C181 \\sim C182 \\sim C183
\\sim C184 \\sim C159 \\sim C109 \\sim C123 \\sim C138 \\sim C139 \\sim C146
\\sim C129 \\sim C143 \\sim C153 \\sim C165 \\sim C166 \\sim C104 \\sim C127
\\sim C133 \\sim C145 \\sim C167: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.03 within 2A
N1 \\sim N8 \\sim N9 \\sim C186 \\sim C187 \\sim C188 \\sim C189 \\sim C190:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.03 within 2A
Cl3 \\sim Cl4 \\sim C159: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 N3, N11, N12, C129, C143, C153, C165, C166
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, N8, N9, C186, C187, C188, C189, C190
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Everything fixed:
 O1, H1, O2, H2, O3, H3, O4, H4
6.b Riding coordinates:
 C187(H18A,H18B,H18C), C188(H18D,H18E,H18F), C129(H12D,H12E,H12F), C166(H16D,
 H16E,H16F)
6.c Rotating group:
 N2(H2A,H2B)
6.d Secondary CH2 refined with riding coordinates:
 C185(H18J,H18K), C159(H15D,H15E)
6.e Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C10(H10), C13(H13), C14(H14), C21(H21), C24(H24), C34(H34),
 C35(H35), C39(H39), C43(H43), C45(H45), C48(H48), C51(H51), C52(H52), C55(H55),
  C59(H59), C60(H60), C61(H61), C62(H62), C65(H65), C67(H67), C68(H68),
 C73(H73), C76(H76), C79(H79), C80(H80), C81(H81), C82(H82), C83(H83), C85(H85),
  C86(H86), C87(H87), C91(H91), C92(H92), C94(H94), C95(H95), C96(H96),
 C97(H97), C98(H98), C99(H99), C100(H100), C101(H101), C102(H102), C105(H105),
 C106(H106), C107(H107), C110(H110), C111(H111), C112(H112), C113(H113),
 C114(H114), C115(H115), C118(H118), C119(H119), C120(H120), C121(H121),
 C122(H122), C124(H124), C125(H125), C128(H128), C130(H130), C134(H134),
 C135(H135), C136(H136), C137(H137), C142(H142), C144(H144), C147(H147),
 C148(H148), C149(H149), C150(H150), C151(H151), C152(H152), C154(H154),
 C155(H155), C156(H156), C157(H157), C158(H158), C160(H160), C162(H162),
 C163(H163), C164(H164), C168(H168), C169(H169), C170(H170), C171(H171),
 C172(H172), C173(H173), C174(H174), C175(H175), C180(H180), C181(H181),
 C182(H182), C183(H183), C184(H184)
6.f Fitted hexagon refined as free rotating group:
 C116(C117,C118,C119,C120,C121)
6.g X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N3(H3B,H3C), N4(H4A,H4B)
6.h Naphthalene refined as free rotating group:
 C174(C175,C176,C177,C178,C179,C180,C181,C182,C183)
6.i Idealised Me refined as rotating group:
 C189(H18G,H18H,H18I), C190(H19A,H19B,H19C), C109(H10A,H10B,H10C), C138(H13A,
 H13B,H13C), C139(H13D,H13E,H13F), C146(H14A,H14B,H14C), C143(H14G,H14H,H14I),
 C153(H15A,H15B,H15C), C127(H12A,H12B,H12C), C133(H13G,H13H,H13I), C145(H14D,
 H14E,H14F), C167(H16A,H16B,H16C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 728 electrons were 
found in a volume of 3388\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
4[CH2Cl2], 1.5[H2O] per Asymmetric Unit 
which account for 732 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              8327
_shelx_hkl_checksum              57647
_shelx_fab_checksum              8285
_olex2_submission_special_instructions 'No special instructions were received'