Bulky metallocavitands with a chiral cavity constructed by aluminum and magnesium atrane-likes: enantioselective recognition and separation of racemic alcohols.
Li, Yingguo; Yu, Dawei; Dai, Zhongran; Zhang, Jinjin; Shao, Yongliang; Tang, Ning; Wu, Jincai; Dalton transactions (Cambridge, England : 2003) 44 (2015) 5692–5702; doi:10.1039/c4dt03848g

data_7033986
_publ_section_title
;
 Bulky metallocavitands with a chiral cavity constructed by aluminum and
 magnesium atrane-likes: enantioselective recognition and separation of
 racemic alcohols.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5692
_journal_page_last               5702
_journal_paper_doi               10.1039/c4dt03848g
_journal_volume                  44
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety
'4(C7 H8), C107 H164 Mg4 N3 O14, C6 H16 N, C4 H9 O'
_chemical_formula_sum            'C145 H221 Mg4 N4 O15'
_chemical_formula_weight         2357.50
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-01-21 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.577(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.8715(5)
_cell_length_b                   26.8064(8)
_cell_length_c                   17.2847(5)
_cell_measurement_reflns_used    15167
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3190
_cell_measurement_theta_min      4.1790
_cell_volume                     7148.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega    1.00   70.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 46

  2 omega  -82.00  -47.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -60.0000 23

  3 omega    0.00   27.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 18

  4 omega   44.00   69.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 17

  5 omega   -6.00   79.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -150.0000 57

  6 omega   33.00  115.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 55

  7 omega    1.00   85.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -68.0000  152.6535 56

  8 omega   26.00   53.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  150.0000 18

  9 omega   15.00   69.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000    0.0000 36

 10 omega   39.00   96.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -44.0000   92.0123 38

 11 omega   42.00   81.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -90.0000 26

 12 omega  105.00  153.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000    0.0000 32

 13 omega   55.00  124.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 46

 14 omega   41.00   77.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -30.0000 24

 15 omega   55.00   82.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  150.0000 18

 16 omega   40.00   82.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -150.0000 28

 17 omega  130.00  176.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  150.0000 31

 18 omega   59.00   93.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -60.0000 23

 19 omega   48.00  112.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 43

 20 omega  111.00  138.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000 -150.0000 18

 21 omega  113.00  177.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  150.0000 43

 22 omega   72.00   99.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000    0.0000 18

 23 omega   91.00  116.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 17

 24 omega   49.00  115.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 44

 25 omega   55.00   91.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 24

 26 omega   54.00   91.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000    0.0000 25

 27 omega   63.00  103.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -120.0000 27

 28 omega   54.00   79.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -21.0000   68.4130 17

 29 omega  113.00  150.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 25

 30 omega   73.00  100.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 18

 31 omega   43.00   97.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000  -30.0000 36

 32 omega   57.00   91.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  150.0000 23

 33 omega   65.00   92.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -90.0000 18

 34 omega  132.00  169.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  -60.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0323856000
_diffrn_orient_matrix_UB_12      0.0160903000
_diffrn_orient_matrix_UB_13      0.0874818000
_diffrn_orient_matrix_UB_21      0.0299745000
_diffrn_orient_matrix_UB_22      0.0503074000
_diffrn_orient_matrix_UB_23      -0.0273879000
_diffrn_orient_matrix_UB_31      -0.0895412000
_diffrn_orient_matrix_UB_32      0.0226826000
_diffrn_orient_matrix_UB_33      -0.0014258000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41479
_diffrn_reflns_theta_full        70.77
_diffrn_reflns_theta_max         70.77
_diffrn_reflns_theta_min         3.30
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2574
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.866
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1582
_refine_ls_number_reflns         21494
_refine_ls_number_restraints     109
_refine_ls_restrained_S_all      3.628
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.140
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1394P)^2^+1.5354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2030
_reflns_number_gt                19227
_reflns_number_total             21494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt03848g2.cif
_cod_data_source_block           yudawei1118
_cod_depositor_comments
'Adding full bibliography for 7033982--7033987.cif.'
_cod_database_code               7033986
_reflns_odcompleteness_completeness 92.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C132-C133
 1.54 with sigma of 0.02
 C140-C145
 1.54 with sigma of 0.02
 C132-C134 \\sim C132-C138
 with sigma of 0.02
 C145-C139 \\sim C145-C141
 with sigma of 0.02
3. Restrained atomic chiral volume
 C133
 fixed at 0 with sigma of 0.1
 C140
 fixed at 0 with sigma of 0.1
4. Rigid bond restraints
 C12, C13, C14, C15, C13', C14', C15'
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C60, C61, C62, C63
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Uiso/Uaniso restraints and constraints
C12 \\sim C13 \\sim C14 \\sim C15 \\sim C13' \\sim C14' \\sim C15': within 1.7A
with sigma of 0.0001 and sigma for terminal atoms of 0.0002
C60 \\sim C61 \\sim C62 \\sim C63: within 1.7A with sigma of 0.002 and sigma
for terminal atoms of 0.004
6. Others
 Sof(C13')=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C14')=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=Sof(C15')=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
 Sof(C45')=Sof(C46')=Sof(H46D)=Sof(H46E)=Sof(H46F)=Sof(C47')=Sof(H47D)=
 Sof(H47E)=Sof(H47F)=Sof(C48')=Sof(H48D)=Sof(H48E)=Sof(H48F)=1-FVAR(2)
 Sof(C45)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C47)=Sof(H47A)=Sof(H47B)=
 Sof(H47C)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(2)
 Sof(C94')=Sof(H94D)=Sof(H94E)=Sof(H94F)=Sof(C95')=Sof(H95D)=Sof(H95E)=
 Sof(H95F)=Sof(C96')=Sof(H96D)=Sof(H96E)=Sof(H96F)=1-FVAR(3)
 Sof(C94)=Sof(H94A)=Sof(H94B)=Sof(H94C)=Sof(C95)=Sof(H95A)=Sof(H95B)=Sof(H95C)=
 Sof(C96)=Sof(H96A)=Sof(H96B)=Sof(H96C)=FVAR(3)
7.a Riding coordinates:
 O13(H13), O14(H14)
7.b Ternary CH refined with riding coordinates:
 N4(H4), C31(H31), C64(H64), C97(H97), C101(H101), C105(H105)
7.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C22(H22A,H22B), C40(H40A,H40B), C55(H55A,H55B), C73(H73A,H73B),
 C88(H88A,H88B), C102(H10G,H10H), C106(H10O,H10P), C110(H11V,H11W), C112(H11D,
 H11E), C114(H11I,H11J), C116(H11N,H11O)
7.d Me refined with riding coordinates:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13'(H13D,H13E,H13F),
 C14'(H14D,H14E,H14F), C15'(H15D,H15E,H15F), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C33(H33A,H33B,H33C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C),
 C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,
 H48C), C46'(H46D,H46E,H46F), C47'(H47D,H47E,H47F), C48'(H48D,H48E,H48F),
 C57(H57A,H57B,H57C), C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C61(H61A,H61B,
 H61C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C66(H66A,H66B,H66C), C75(H75A,
 H75B,H75C), C76(H76A,H76B,H76C), C77(H77A,H77B,H77C), C79(H79A,H79B,H79C),
 C80(H80A,H80B,H80C), C81(H81A,H81B,H81C), C90(H90A,H90B,H90C), C91(H91A,H91B,
 H91C), C92(H92A,H92B,H92C), C94(H94A,H94B,H94C), C95(H95A,H95B,H95C), C96(H96A,
 H96B,H96C), C94'(H94D,H94E,H94F), C95'(H95D,H95E,H95F), C96'(H96D,H96E,H96F),
 C99(H99A,H99B,H99C), C100(H10D,H10E,H10F), C103(H10I,H10J,H10K), C104(H10L,
 H10M,H10N), C107(H10Q,H10R,H10S), C108(H10T,H10U,H10V), C111(H11X,H11Y,H),
 C113(H11F,H11G,H11H), C115(H11K,H11L,H11M), C117(H11P,H11Q,H11R), C118(H11S,
 H11T,H11U), C125(H12A,H12B,H12C), C132(H13G,H13H,H13I), C145(H14G,H14H,H14I)
7.e Aromatic/amide H refined with riding coordinates:
 C134(H134), C135(H135), C136(H136), C137(H137), C138(H138), C3(H3), C5(H5),
 C18(H18), C20(H20), C36(H36), C38(H38), C51(H51), C53(H53), C69(H69), C71(H71),
  C84(H84), C86(H86), C120(H120), C121(H121), C122(H122), C123(H123),
 C124(H124), C127(H127), C128(H128), C129(H129), C130(H130), C131(H131),
 C139(H139), C141(H141), C142(H142), C143(H143), C144(H144)
7.f Fitted hexagon refined as free rotating group:
 C133(C134,C135,C136,C137,C138), C139(C140,C141,C142,C143,C144)
7.g Tetrahedral OH refined with riding coordinates:
 O15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'