A systematic study of the interplay between guest molecule structure and intermolecular interactions in crystalline sponges
Carroll, Robert C.; Harrowven, David C.; Pearce, James E.; Coles, Simon J.; IUCrJ 10 (2023) 497–508; doi:10.1107/S2052252523005146

data_1569413
_publ_section_title
;
 A systematic study of the interplay between guest molecule structure and
 intermolecular interactions in crystalline sponges
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first              497
_journal_page_last               508
_journal_paper_doi               10.1107/S2052252523005146
_journal_volume                  10
_journal_year                    2023
_chemical_formula_moiety         'C36 H24 I6 N12 Zn3, 1.328(C15 H16 O)'
_chemical_formula_sum            'C55.92 H45.25 I6 N12 O1.33 Zn3'
_chemical_formula_weight         1864.16
_chemical_name_common
'Benzyl Biaryl Alcohol (absorbed in crystalline sponge)'
_chemical_name_systematic
'(2',6'-dimethyl-[1,1'-biphenyl]-2-yl)methanol (absorbed into crystalline sponge)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-05-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.1207(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.6703(5)
_cell_length_b                   14.9029(2)
_cell_length_c                   30.5678(6)
_cell_measurement_reflns_used    18016
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9200
_cell_measurement_theta_min      3.2130
_cell_volume                     15887.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_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      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_dtime           0.000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -134.00-109.00   0.50    0.80    -- -103.00-153.00-112.00   50
  2  \w   -130.00 -31.00   0.50    0.80    -- -103.00 153.00 -71.00  198
  3  \w   -151.00-126.00   0.50    0.80    -- -103.00-120.00  46.00   50
  4  \w    -98.00 -58.00   0.50    0.80    -- -103.00 120.00 129.00   80
  5  \w    -95.00 -68.00   0.50    0.80    -- -103.00 125.00-180.00   54
  6  \w   -121.00 -90.00   0.50    0.80    -- -103.00 -30.00 -60.00   62
  7  \w   -173.00-146.00   0.50    0.80    -- -103.00 -30.00 -60.00   54
  8  \w    -56.00 -31.00   0.50    0.80    -- -103.00  61.00-150.00   50
  9  \w    -68.00 -33.00   0.50    0.80    -- -103.00  61.00-120.00   70
 10  \w    -62.00 -37.00   0.50    0.80    -- -103.00 125.00-180.00   50
 11  \w   -172.00 -92.00   0.50    0.80    -- -103.00 -15.00-150.00  160
 12  \w    -66.00 -36.00   0.50    0.80    -- -103.00 125.00-150.00   60
 13  \w    -64.00 -35.00   0.50    0.80    -- -103.00  61.00 150.00   58
 14  \w    -66.00 -33.00   0.50    0.80    -- -103.00  61.00 -60.00   66
 15  \w     43.00 130.00   0.50    0.80    --  101.75-153.00-112.00  174
 16  \w     65.00 109.00   0.50    0.80    --  101.75-120.00  46.00   88
 17  \w    106.00 139.00   0.50    0.80    --  101.75 120.00 129.00   66
 18  \w     89.00 114.00   0.50    0.80    --  101.75 153.00 -71.00   50
 19  \w     89.00 116.00   0.50    0.80    --  101.75  30.00-120.00   54
 20  \w     31.00  62.00   0.50    0.80    --  101.75 -61.00 -90.00   62
 21  \w     95.00 172.00   0.50    0.80    --  101.75  61.00  30.00  154
 22  \w     45.00  71.00   0.50    0.80    --  101.75 -61.00  60.00   52
 23  \w     85.00 172.00   0.50    0.80    --  101.75  61.00 120.00  174
 24  \w    120.00 147.00   0.50    0.80    --  101.75  30.00-120.00   54
 25  \w     58.00 102.00   0.50    0.80    --  101.75 -94.00-120.00   88
 26  \w     30.00  73.00   0.50    0.80    --  101.75 -61.00  30.00   86
 27  \w     56.00 103.00   0.50    0.80    --  101.75 -94.00  90.00   94
 28  \w     64.00 105.00   0.50    0.80    --  101.75 -94.00 -90.00   82
 29  \w     32.00  72.00   0.50    0.80    --  101.75 -61.00  90.00   80
 30  \w     84.00 170.00   0.50    0.80    --  101.75  77.00-150.00  172
 31  \w     36.00  70.00   0.50    0.80    --  101.75 -94.00  60.00   68
 32  \w     77.00 102.00   0.50    0.80    --  101.75 -94.00  60.00   50
 33  \w     39.00  68.00   0.50    0.80    --  101.75 -61.00 -60.00   58
 34  \w   -111.00 -66.00   0.50    0.20    --  -46.49 153.00 -71.00   90
 35  \w   -104.00 -58.00   0.50    0.20    --  -46.49-153.00-112.00   92
 36  \w    -90.00 -51.00   0.50    0.20    --  -46.49 120.00 129.00   78
 37  \w     64.00  92.00   0.50    0.20    --   46.49 153.00 -71.00   56
 38  \w     32.00  58.00   0.50    0.20    --   46.49-120.00  46.00   52
 39  \w    -38.00  27.00   0.50    0.20    --  -46.49  37.00-120.00  130
 40  \w     -8.00  19.00   0.50    0.20    --  -46.49  19.00 -60.00   54
 41  \w    -12.00  26.00   0.50    0.20    --  -46.49  19.00 -30.00   76
 42  \w    -19.00  28.00   0.50    0.20    --  -46.49  19.00-180.00   94
 43  \w   -110.00 -82.00   0.50    0.20    --  -46.49 -77.00   0.00   56
 44  \w    -71.00 -24.00   0.50    0.20    --  -46.49 -77.00   0.00   94
 45  \w     35.00 116.00   0.50    0.20    --   46.49  57.00-120.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details
'Rigaku Oxford Difffraction, UG2 \k goniometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0062939000
_diffrn_orient_matrix_UB_12      0.0041883000
_diffrn_orient_matrix_UB_13      0.0513797000
_diffrn_orient_matrix_UB_21      -0.0051790000
_diffrn_orient_matrix_UB_22      0.1026399000
_diffrn_orient_matrix_UB_23      -0.0024692000
_diffrn_orient_matrix_UB_31      -0.0434146000
_diffrn_orient_matrix_UB_32      -0.0115811000
_diffrn_orient_matrix_UB_33      -0.0032255000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            89714
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         2.534
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    19.669
_exptl_absorpt_correction_T_max  0.421
_exptl_absorpt_correction_T_min  0.062
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       block
_exptl_crystal_F_000             7067
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.873
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     950
_refine_ls_number_reflns         14520
_refine_ls_number_restraints     320
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0890
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+522.7365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2098
_refine_ls_wR_factor_ref         0.2106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13891
_reflns_number_total             14520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5059.cif
_cod_data_source_block           BBA_CrystallineSponge
_cod_original_cell_volume        15887.3(5)
_cod_database_code               1569413
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         '(Zn3 I6 N12 H24 C36) (C14 H15 O)2 (C6 H12)3'
_chemical_oxdiff_usercomment     'Extended Biaryl'
_shelx_estimated_absorpt_t_max   0.380
_shelx_estimated_absorpt_t_min   0.057
_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, All O(H) groups
2. Restrained distances
 O1B-C14B
 1.43 with sigma of 0.02
 C14A-C5A = C15A-C12A = C8B-C13B = C15B-C12B
 1.54 with sigma of 0.02
 C15C-C12C
 1.54 with sigma of 0.02
 C14B-C5B
 1.54 with sigma of 0.02
 O1A-C14A
 1.43 with sigma of 0.02
 C14C-C5C
 1.54 with sigma of 0.02
 O1C-C14C
 1.43 with sigma of 0.02
 C7C-C4C
 1.54 with sigma of 0.02
 C7C-C13C
 2.5 with sigma of 0.04
 C9C-C13C
 2.5 with sigma of 0.04
 O1B-C5B
 2.4 with sigma of 0.04
 O1A-C5A
 2.4 with sigma of 0.04
 C6B-C14B
 2.5 with sigma of 0.04
 C4B-C14B
 2.5 with sigma of 0.04
 C3C-C7C \\sim C7C-C5C
 with sigma of 0.04
 C12C-C4C \\sim C4C-C8C
 with sigma of 0.04
3. Restrained planarity
 C9C, C8C, C7C, C13C
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C7A \\sim C12A \\sim C4A \\sim C8A \\sim C15A \\sim C11A \\sim C5A \\sim C3A
\\sim C9A \\sim C10A \\sim C6A \\sim C14A \\sim C2A \\sim C1A \\sim O1A: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C3B \\sim C7B \\sim C12B \\sim C8B \\sim C4B \\sim C11B \\sim C15B \\sim C9B
\\sim C13B \\sim C5B \\sim C10B \\sim C6B \\sim C14B \\sim C2B \\sim C1B \\sim
O1B: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within
1.7A
C13C \\sim C4C \\sim C5C \\sim C3C \\sim C7C \\sim C6C \\sim C14C \\sim C2C
\\sim C8C \\sim C12C \\sim C1C \\sim O1C \\sim C9C \\sim C15C \\sim C11C \\sim
C10C: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 1.7A
5. Others
 Sof(I405)=Sof(Zn43)=Sof(I406)=1-FVAR(1)
 Sof(I305)=Sof(I306)=Sof(Zn33)=FVAR(1)
 Sof(I402)=Sof(Zn41)=Sof(I401)=1-FVAR(2)
 Sof(I302)=Sof(Zn31)=Sof(I301)=FVAR(2)
 Fixed Sof: I303(0.6) I304(0.6) Zn32(0.6) C7A(0.56985) C12A(0.56985)
 C11A(0.56985) H11A(0.56985) C10A(0.56985) H10A(0.56985) C9A(0.56985)
 H9A(0.56985) C8A(0.56985) C5A(0.56985) C6A(0.56985) H6A(0.56985) C1A(0.56985)
 H1A(0.56985) C2A(0.56985) H2A(0.56985) C3A(0.56985) H3A(0.56985) C4A(0.56985)
 C15A(0.56985) H15A(0.56985) H15B(0.56985) H15C(0.56985) C7B(0.38685)
 C12B(0.38685) C11B(0.38685) H11B(0.38685) C10B(0.38685) H10B(0.38685)
 C9B(0.38685) H9B(0.38685) C8B(0.38685) O1A(0.56985) H1AA(0.56985)
 C14A(0.56985) H14A(0.56985) H14B(0.56985) C15B(0.38685) H15D(0.38685)
 H15E(0.38685) H15F(0.38685) C4B(0.38685) C5B(0.38685) C6B(0.38685)
 H6B(0.38685) C1B(0.38685) H1B(0.38685) C2B(0.38685) H2B(0.38685) C3B(0.38685)
 H3B(0.38685) O1B(0.38685) H1BA(0.38685) C14B(0.38685) H14C(0.38685)
 H14D(0.38685) I404(0.37) Zn42(0.37) I403(0.37) I504(0.03) I503(0.03)
 C13B(0.38685) H13D(0.38685) H13E(0.38685) H13F(0.38685) C13A(0.56985)
 H13A(0.56985) H13B(0.56985) H13C(0.56985) C4C(0.37162) C5C(0.37162)
 C6C(0.37162) H6C(0.37162) C1C(0.37162) H1C(0.37162) C2C(0.37162) H2C(0.37162)
 C3C(0.37162) H3C(0.37162) O1C(0.37162) H1CA(0.37162) C15C(0.37162)
 H15G(0.37162) H15H(0.37162) H15I(0.37162) C7C(0.37162) C8C(0.37162)
 C9C(0.37162) H9C(0.37162) C10C(0.37162) H10C(0.37162) C11C(0.37162)
 H11C(0.37162) C12C(0.37162) C13C(0.37162) H13G(0.37162) H13H(0.37162)
 H13I(0.37162) C14C(0.37162) H14E(0.37162) H14F(0.37162) Zn52(0.03)
 Fixed Uiso: I402(0.08) Zn41(0.08) I401(0.08) I504(0.08) I503(0.08) Zn52(0.08)
6.a Secondary CH2 refined with riding coordinates:
 C14A(H14A,H14B), C14B(H14C,H14D), C14C(H14E,H14F)
6.b Aromatic/amide H refined with riding coordinates:
 C335(H335), C333(H333), C329(H329), C322(H322), C336(H336), C312(H312),
 C323(H323), C319(H319), C310(H310), C313(H313), C320(H320), C318(H318),
 C301(H301), C332(H332), C317(H317), C328(H328), C304(H304), C315(H315),
 C331(H331), C302(H302), C305(H305), C314(H314), C330(H330), C311(H311),
 C11A(H11A), C10A(H10A), C9A(H9A), C6A(H6A), C1A(H1A), C2A(H2A), C3A(H3A),
 C11B(H11B), C10B(H10B), C9B(H9B), C6B(H6B), C1B(H1B), C2B(H2B), C3B(H3B),
 C6C(H6C), C1C(H1C), C2C(H2C), C3C(H3C), C9C(H9C), C10C(H10C), C11C(H11C)
6.c Fitted hexagon refined as free rotating group:
 C7A(C12A,C11A,C10A,C9A,C8A), C5A(C6A,C1A,C2A,C3A,C4A), C7B(C12B,C11B,C10B,C9B,
 C8B), C4B(C5B,C6B,C1B,C2B,C3B), C4C(C5C,C6C,C1C,C2C,C3C), C7C(C8C,C9C,C10C,
 C11C,C12C)
6.d Tetrahedral OH refined with riding coordinates:
 O1A(H1AA), O1B(H1BA), O1C(H1CA)
6.e Idealised Me refined with everything fixed:
 C15B(H15D,H15E,H15F), C13B(H13D,H13E,H13F), C15C(H15G,H15H,H15I), C13C(H13G,
 H13H,H13I)
6.f Idealised Me refined as rotating group:
 C15A(H15A,H15B,H15C), C13A(H13A,H13B,H13C)
;
_shelx_res_checksum              86547
_shelx_hkl_checksum              26064
_olex2_date_sample_data_collection 2021-11-18
_olex2_date_sample_submission    2021-11-18
_olex2_submission_original_sample_id 'Benzyl Biaryl Alcohol'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.427
_oxdiff_exptl_absorpt_empirical_full_min 0.482