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_1569412
_publ_section_title
;
 A systematic study of the interplay between guest molecule structure and
 intermolecular interactions in crystalline sponges
;
_journal_coeditor_code           LT5059
_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, 1.01(C16 H18 O), 0.155(C6 H12)'
_chemical_formula_sum            'C53.14 H44.05 I6 N12 O1.01 Zn3'
_chemical_formula_weight         1824.46
_chemical_name_common
'Benzyl Biaryl Alcohol-9-Methyl (absorbed in crystalline sponge)'
_chemical_name_systematic
'(2',3',6'-trimethyl-[1,1'-biphenyl]-2-yl)methanol (absorbed in 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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.400(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.5224(6)
_cell_length_b                   14.9127(2)
_cell_length_c                   30.9220(5)
_cell_measurement_reflns_used    11664
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.3960
_cell_measurement_theta_min      2.9190
_cell_volume                     15998.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel array detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000HE'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_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   -163.00 -91.00   0.50    0.80    -- -103.00 -26.00-169.00  144
  2  \w   -172.00-132.00   0.50    0.80    -- -103.00 -61.00 -30.00   80
  3  \w    -61.00 -36.00   0.50    0.80    -- -103.00  61.00 -90.00   50
  4  \w    -69.00 -43.00   0.50    0.80    -- -103.00  61.00  90.00   52
  5  \w    -61.00 -35.00   0.50    0.80    -- -103.00  77.00-180.00   52
  6  \w   -103.00 -71.00   0.50    0.80    -- -103.00  77.00-180.00   64
  7  \w    -76.00 -45.00   0.50    0.80    -- -103.00  77.00  90.00   62
  8  \w   -126.00-100.00   0.50    0.80    -- -103.00 -61.00 -30.00   52
  9  \w     90.00 134.00   0.50    0.80    --  101.75  26.00  -6.00   88
 10  \w     30.00  71.00   0.50    0.80    --  101.75 -61.00  90.00   82
 11  \w     84.00 110.00   0.50    0.80    --  101.75-125.00-180.00   52
 12  \w     34.00  73.00   0.50    0.80    --  101.75 -61.00-180.00   78
 13  \w     30.00  71.00   0.50    0.80    --  101.75 -61.00   0.00   82
 14  \w     36.00  72.00   0.50    0.80    --  101.75 -61.00  60.00   72
 15  \w     32.00  73.00   0.50    0.80    --  101.75 -61.00-120.00   82
 16  \w     36.00  67.00   0.50    0.80    --  101.75-125.00-180.00   62
 17  \w     36.00  63.00   0.50    0.80    --  101.75 -61.00 -30.00   54
 18  \w     35.00  68.00   0.50    0.80    --  101.75 -61.00-150.00   66
 19  \w     30.00  66.00   0.50    0.80    --  101.75 -61.00  30.00   72
 20  \w     29.00  67.00   0.50    0.80    --  101.75 -61.00 -90.00   76
 21  \w    -74.00 -34.00   0.50    0.30    --  -46.47 -26.00-169.00   80
 22  \w   -115.00 -89.00   0.50    0.30    --  -46.47 -26.00-169.00   52
 23  \w     35.00 120.00   0.50    0.30    --   46.47  26.00  -6.00  170
 24  \w     -4.00  25.00   0.50    0.30    --   46.47 -26.00-169.00   58
 25  \w    -39.00  27.00   0.50    0.30    --  -46.47  37.00 120.00  132
 26  \w    -22.00  20.00   0.50    0.30    --  -46.47  19.00 -90.00   84
 27  \w    -29.00  12.00   0.50    0.30    --  -46.47  26.00  -6.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details
'Rigaku Oxford Difffraction, UG2 \k goniometer'
_diffrn_measurement_device_type
'Rigaku 007HF equipped with Varimax confocal mirrors and a UG2 goniometer and HyPix 6000HE detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0184117000
_diffrn_orient_matrix_UB_12      0.0014176000
_diffrn_orient_matrix_UB_13      0.0498716000
_diffrn_orient_matrix_UB_21      -0.0378675000
_diffrn_orient_matrix_UB_22      -0.0353475000
_diffrn_orient_matrix_UB_23      0.0102906000
_diffrn_orient_matrix_UB_31      0.0140850000
_diffrn_orient_matrix_UB_32      -0.0970648000
_diffrn_orient_matrix_UB_33      -0.0030245000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            52459
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         2.926
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    19.515
_exptl_absorpt_correction_T_max  0.392
_exptl_absorpt_correction_T_min  0.104
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       block
_exptl_crystal_F_000             6904
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1054
_refine_ls_number_reflns         14531
_refine_ls_number_restraints     322
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0604P)^2^+80.9999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13103
_reflns_number_total             14531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5059.cif
_cod_data_source_block           BBA-9-Methyl_CrystallineSponge
_cod_database_code               1569412
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         '(Zn3 I6 N12 H24 C36) (C16 H18 O)'
_chemical_oxdiff_usercomment     JP-9300-64
_shelx_estimated_absorpt_t_max   0.387
_shelx_estimated_absorpt_t_min   0.094
_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
 O2A-C16A
 1.43 with sigma of 0.02
 C7C-C4C
 1.54 with sigma of 0.02
 O1C-C14C
 1.43 with sigma of 0.02
 C7B-C4B
 1.54 with sigma of 0.02
 C14B-C5B
 1.54 with sigma of 0.02
 C16C-C12C
 1.54 with sigma of 0.02
 C16B-C12B = C15B-C9B
 1.54 with sigma of 0.02
 O1B-C14B
 1.43 with sigma of 0.02
 C13B-C8B
 1.54 with sigma of 0.02
 C13C-C8C
 1.54 with sigma of 0.02
 C5C-C14C
 1.54 with sigma of 0.02
 C801-C802 = C801-C806 = C802-C803 = C803-C804 = C804-C805 = C805-C806
 1.54 with sigma of 0.02
 C5C-O1C
 2.4 with sigma of 0.04
 C8C-C15C
 2.5 with sigma of 0.04
 C10C-C15C
 2.5 with sigma of 0.04
 C11B-C16B
 2.5 with sigma of 0.04
 C7B-C16B
 2.5 with sigma of 0.04
 C8B-C15B
 2.5 with sigma of 0.04
 C10B-C15B
 2.5 with sigma of 0.04
 C7C-C13C
 2.5 with sigma of 0.04
 C9B-C13B
 2.5 with sigma of 0.04
 C9C-C13C
 2.5 with sigma of 0.04
 C7B-C13B
 2.5 with sigma of 0.04
 O1C-C5C
 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
 C801-C803 = C801-C805 = C802-C804 = C803-C805 = C804-C806
 2.54 with sigma of 0.04
 C8B-C4B \\sim C4B-C12B
 with sigma of 0.04
 C3B-C7B \\sim C7B-C5B
 with sigma of 0.04
 C8C-C4C \\sim C4C-C12C
 with sigma of 0.04
 C5C-C7C \\sim C7C-C3C
 with sigma of 0.04
 C4C-C14C \\sim C14C-C6C
 with sigma of 0.02
 C11C-C16C \\sim C16C-C7C
 with sigma of 0.02
 I305-Zn33 \\sim I405-Zn43
 with sigma of 0.02
 I306-Zn33 \\sim I406-Zn43
 with sigma of 0.02
 Zn33-N312 \\sim Zn43-N312
 with sigma of 0.02
 I306-N312 \\sim I406-N312
 with sigma of 0.04
 I305-I306 \\sim I405-I406
 with sigma of 0.04
 I305-N312 \\sim I405-N312
 with sigma of 0.04
 I304-N307 \\sim I404-N307
 with sigma of 0.04
 I303-N307 \\sim I403-N307
 with sigma of 0.04
 I303-Zn32 \\sim I403-Zn42
 with sigma of 0.02
 I303-I304 \\sim I403-I404
 with sigma of 0.04
 I303-N306 \\sim I403-N306
 with sigma of 0.04
 I304-Zn32 \\sim I404-Zn42
 with sigma of 0.02
 I304-N306 \\sim I404-N306
 with sigma of 0.04
 Zn32-N307 \\sim Zn42-N307
 with sigma of 0.02
 Zn32-N306 \\sim Zn42-N306
 with sigma of 0.02
 I302-I301 \\sim I402-I401
 with sigma of 0.04
 I302-Zn31 \\sim I402-Zn41
 with sigma of 0.02
 I302-N301 \\sim I402-N301
 with sigma of 0.04
 I301-Zn31 \\sim I401-Zn41
 with sigma of 0.02
 I301-N301 \\sim I401-N301
 with sigma of 0.04
 Zn31-N301 \\sim Zn41-N301
 with sigma of 0.02
 I405-Zn43 \\sim I505-Zn53
 with sigma of 0.02
 I406-Zn43 \\sim I506-Zn53
 with sigma of 0.02
 C801-C805 \\sim C803-C805 \\sim C802-C806 \\sim C802-C804 \\sim C804-C806
\\sim C801-C803
 with sigma of 0.04
 C801-C802 \\sim C802-C803 \\sim C803-C804 \\sim C804-C805 \\sim C805-C806
\\sim C806-C801
 with sigma of 0.02
3. Restrained planarity
 C8B, C7B, C12B, C4B
 with sigma of 0.05
 C4B, C5B, C6B, C14B
 with sigma of 0.05
4. Uiso/Uaniso restraints and constraints
C12C \\sim C7C \\sim C8C \\sim C4C \\sim C11C \\sim C16C \\sim C9C \\sim C13C
\\sim C5C \\sim C3C \\sim C10C \\sim C15C \\sim C14C \\sim C6C \\sim C2C \\sim
O1C \\sim C1C: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
C4B \\sim C5B \\sim C3B \\sim C7B \\sim C6B \\sim C14B \\sim C2B \\sim C8B
\\sim C12B \\sim C1B \\sim O1B \\sim C9B \\sim C13B \\sim C11B \\sim C16B \\sim
C10B \\sim C15B: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
C801 \\sim C802 \\sim C803 \\sim C804 \\sim C805 \\sim C806: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C801, C802, C803, C804, C805, C806
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: I303(0.6268) I305(0.52802) I304(0.6268) I302(0.57096)
 I301(0.57096) I306(0.52802) Zn32(0.6268) Zn33(0.52802) Zn31(0.57096)
 C7A(0.53538) C12A(0.53538) C11A(0.53538) H11A(0.53538) C10A(0.53538)
 H10A(0.53538) C9A(0.53538) H9A(0.21415) C8A(0.53538) H8A(0.21415)
 C16A(0.53538) H16A(0.32123) H16B(0.32123) H16C(0.32123) H16D(0.21415)
 H16E(0.21415) C4A(0.53538) C5A(0.53538) C6A(0.53538) H6A(0.53538) C1A(0.53538)
 H1A(0.53538) C2A(0.53538) H2A(0.32123) C3A(0.53538) H3A(0.32123) I405(0.44717)
 Zn43(0.44717) I406(0.44717) I403(0.319) Zn42(0.319) I404(0.319) I503(0.05421)
 I504(0.05421) Zn52(0.05421) I505(0.02479) I506(0.02479) Zn53(0.02479)
 C15A(0.32123) H15A(0.32123) H15B(0.32123) H15C(0.32123) C13A(0.32123)
 H13A(0.32123) H13B(0.32123) H13C(0.32123) O2A(0.21415) H2AA(0.21415)
 C14A(0.53538) H14C(0.21415) H14D(0.21415) H14E(0.27877) H14A(0.32123)
 H14B(0.21415) C4B(0.28669) C5B(0.28669) C6B(0.28669) H6B(0.28669) C1B(0.28669)
 H1B(0.28669) C2B(0.28669) H2B(0.28669) C3B(0.28669) H3B(0.28669) C7B(0.28669)
 C8B(0.28669) C9B(0.28669) C10B(0.28669) H10B(0.28669) C11B(0.28669)
 H11B(0.28669) C12B(0.28669) O1B(0.28669) H1BA(0.28669) C7C(0.19118)
 C12C(0.19118) C11C(0.19118) H11C(0.19118) C10C(0.19118) H10C(0.19118)
 C9C(0.19118) C8C(0.19118) C15C(0.19118) H15G(0.19118) H15H(0.19118)
 H15I(0.19118) O1A(0.32123) H1AA(0.32123) C17A(0.21415) H17A(0.21415)
 H17B(0.21415) H17C(0.21415) C18A(0.21415) H18A(0.21415) H18B(0.21415)
 H18C(0.21415) I402(0.40378) Zn41(0.40378) I401(0.40378) I501(0.02525)
 I502(0.02525) Zn51(0.02525) C16C(0.19118) H16I(0.19118) H16J(0.19118)
 H16K(0.19118) C14C(0.19118) H14H(0.19118) H14I(0.19118) C13C(0.19118)
 H13G(0.19118) H13H(0.19118) H13I(0.19118) C4C(0.19118) C5C(0.19118)
 C6C(0.19118) H6C(0.19118) C1C(0.19118) H1C(0.19118) C2C(0.19118) H2C(0.19118)
 C3C(0.19118) H3C(0.19118) O1C(0.19118) H1CA(0.19118) C16B(0.28669)
 H16F(0.28669) H16G(0.28669) H16H(0.28669) C13B(0.28669) H13D(0.28669)
 H13E(0.28669) H13F(0.28669) C15B(0.28669) H15D(0.28669) H15E(0.28669)
 H15F(0.28669) C14B(0.28669) H14F(0.28669) H14G(0.28669) C801(0.15458)
 H80A(0.15458) H80B(0.15458) C802(0.15458) H80C(0.15458) H80D(0.15458)
 C803(0.15458) H80E(0.15458) H80F(0.15458) C804(0.15458) H80G(0.15458)
 H80H(0.15458) C805(0.15458) H80I(0.15458) H80J(0.15458) C806(0.15458)
 H80K(0.15458) H80L(0.15458)
 Fixed Uiso: I503(0.08) I504(0.08) Zn52(0.08) I505(0.08) I506(0.08) Zn53(0.08)
 I501(0.08) I502(0.08) Zn51(0.08) C801(0.08) C802(0.08) C803(0.08) C804(0.08)
 C805(0.08) C806(0.08)
7.a Secondary CH2 refined with riding coordinates:
 C16A(H16D,H16E), C14A(H14A,H14B), C14C(H14H,H14I), C14B(H14F,H14G), C801(H80A,
 H80B), C802(H80C,H80D), C803(H80E,H80F), C804(H80G,H80H), C805(H80I,H80J),
 C806(H80K,H80L)
7.b Aromatic/amide H refined with riding coordinates:
 C333(H333), C322(H322), C323(H323), C332(H332), C312(H312), C319(H319),
 C313(H313), C320(H320), C330(H330), C301(H301), C317(H317), C318(H318),
 C329(H329), C310(H310), C328(H328), C335(H335), C331(H331), C311(H311),
 C302(H302), C314(H314), C336(H336), C315(H315), C305(H305), C304(H304),
 C11A(H11A), C10A(H10A), C9A(H9A), C8A(H8A), C6A(H6A), C1A(H1A), C2A(H2A),
 C3A(H3A), C6B(H6B), C1B(H1B), C2B(H2B), C3B(H3B), C10B(H10B), C11B(H11B),
 C11C(H11C), C10C(H10C), C6C(H6C), C1C(H1C), C2C(H2C), C3C(H3C)
7.c Fitted hexagon refined as free rotating group:
 C7A(C12A,C11A,C10A,C9A,C8A), C4A(C5A,C6A,C1A,C2A,C3A), C4B(C5B,C6B,C1B,C2B,
 C3B), C7B(C8B,C9B,C10B,C11B,C12B), C7C(C12C,C11C,C10C,C9C,C8C), C4C(C5C,C6C,
 C1C,C2C,C3C)
7.d Tetrahedral OH refined with everything fixed:
 O2A(H2AA), O1B(H1BA), O1A(H1AA), O1C(H1CA)
7.e Idealised Me refined with everything fixed:
 C16A(H16A,H16B,H16C), C15A(H15A,H15B,H15C), C13A(H13A,H13B,H13C), C14A(H14C,
 H14D,H14E), C15C(H15G,H15H,H15I), C17A(H17A,H17B,H17C), C18A(H18A,H18B,H18C),
 C16C(H16I,H16J,H16K), C13C(H13G,H13H,H13I), C16B(H16F,H16G,H16H), C13B(H13D,
 H13E,H13F), C15B(H15D,H15E,H15F)
;
_shelx_res_checksum              98742
_shelx_hkl_checksum              30144
_olex2_date_sample_data_collection 2022-10-12
_olex2_date_sample_submission    2022-10-12
_olex2_submission_original_sample_id 'Benzyl Biaryl Alcohol-3-Methyl'
_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 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.709