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_1569422
_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, 1.45(C13 H10 O I2)'
_chemical_formula_sum            'C22.86 H16.22 I3.75 N6 O0.37 Zn1.5'
_chemical_formula_weight         954.52
_chemical_name_common
'Phenyl Biaryl Alcohol-2,6-Iodine (absorbed in crystalline sponge)'
_chemical_name_systematic
'3,5-diiodo-2'-methyl-[1,1'-biphenyl]-2-ol (absorbed in crystalline sponge)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                98.227(2)
_cell_angle_beta                 91.736(2)
_cell_angle_gamma                113.055(3)
_cell_formula_units_Z            8
_cell_length_a                   14.7780(5)
_cell_length_b                   18.2345(5)
_cell_length_c                   30.7970(5)
_cell_measurement_reflns_used    19346
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.6810
_cell_measurement_theta_min      2.7980
_cell_volume                     7523.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.990
_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   -149.00-124.00   0.50    1.50    -- -103.00-125.00 -40.00   50
  2  \w   -108.00 -31.00   0.50    1.50    -- -103.00 125.00  37.00  154
  3  \w   -116.00 -85.00   0.50    1.50    -- -103.00-145.00 151.00   62
  4  \w   -173.00-105.00   0.50    1.50    -- -103.00 -45.00-150.00  136
  5  \w    -68.00 -30.00   0.50    1.50    -- -103.00  61.00 -60.00   76
  6  \w    -55.00 -30.00   0.50    1.50    -- -103.00 125.00 150.00   50
  7  \w   -111.00 -85.00   0.50    1.50    -- -103.00 125.00 150.00   52
  8  \w    -93.00 -31.00   0.50    1.50    -- -103.00 125.00 -60.00  124
  9  \w   -115.00 -90.00   0.50    1.50    -- -103.00 -45.00  30.00   50
 10  \w   -174.00 -90.00   0.50    1.50    -- -103.00 -15.00-120.00  168
 11  \w    -69.00 -31.00   0.50    1.50    -- -103.00  61.00 -30.00   76
 12  \w    -60.00 -31.00   0.50    1.50    -- -103.00  61.00  60.00   58
 13  \w    -68.00 -31.00   0.50    1.50    -- -103.00  61.00 -90.00   74
 14  \w    -73.00 -47.00   0.50    1.50    -- -103.00  77.00-120.00   52
 15  \w   -172.00 -76.00   0.50    1.50    -- -103.00-125.00   0.00  192
 16  \w    -71.00 -45.00   0.50    1.50    -- -103.00  77.00  30.00   52
 17  \w   -100.00 -75.00   0.50    1.50    -- -103.00  77.00  30.00   50
 18  \w    -68.00 -42.00   0.50    1.50    -- -103.00  61.00  30.00   52
 19  \w   -147.00-120.00   0.50    1.50    -- -103.00 -45.00  30.00   54
 20  \w   -125.00 -76.00   0.50    1.50    -- -103.00 145.00-155.00   98
 21  \w     34.00  92.00   0.50    1.50    --  101.75-145.00 151.00  116
 22  \w     88.00 129.00   0.50    1.50    --  101.75 125.00  37.00   82
 23  \w     75.00 112.00   0.50    1.50    --  101.75-125.00 -40.00   74
 24  \w     95.00 120.00   0.50    1.50    --  101.75 145.00-155.00   50
 25  \w     96.00 126.00   0.50    1.50    --  101.75-145.00 151.00   60
 26  \w    138.00 172.00   0.50    1.50    --  101.75  30.00 150.00   68
 27  \w     37.00 104.00   0.50    1.50    --  101.75-125.00-150.00  134
 28  \w     75.00 108.00   0.50    1.50    --  101.75 -77.00 -30.00   66
 29  \w    126.00 173.00   0.50    1.50    --  101.75  45.00-150.00   94
 30  \w     30.00  70.00   0.50    1.50    --  101.75 -61.00-180.00   80
 31  \w     89.00 127.00   0.50    1.50    --  101.75  30.00 150.00   76
 32  \w     63.00 102.00   0.50    1.50    --  101.75 -94.00 -30.00   78
 33  \w     86.00 173.00   0.50    1.50    --  101.75 125.00 -90.00  174
 34  \w     48.00 111.00   0.50    1.50    --  101.75-125.00 -90.00  126
 35  \w     37.00  73.00   0.50    1.50    --  101.75 -61.00 -90.00   72
 36  \w     89.00 117.00   0.50    1.50    --  101.75  45.00-150.00   56
 37  \w   -118.00 -63.00   0.50    0.26    --  -46.36-145.00 151.00  110
 38  \w    -94.00 -68.00   0.50    0.26    --  -46.36 145.00-155.00   52
 39  \w    -80.00 -55.00   0.50    0.26    --  -46.36 125.00  37.00   50
 40  \w     72.00 101.00   0.50    0.26    --   46.36 145.00-155.00   58
 41  \w     23.00  93.00   0.50    0.26    --   46.36-125.00 -40.00  140
 42  \w     53.00 106.00   0.50    0.26    --   46.36-145.00 151.00  106
 43  \w   -117.00 -34.00   0.50    0.26    --  -46.36 -57.00  90.00  166
 44  \w     -8.00  26.00   0.50    0.26    --  -46.36  19.00 120.00   68
 45  \w   -111.00 -26.00   0.50    0.26    --  -46.36 -77.00-180.00  170
 46  \w    -27.00  28.00   0.50    0.26    --   46.36 -19.00 -60.00  110
 47  \w    -27.00  27.00   0.50    0.26    --   46.36 -19.00  30.00  108
;
_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      -0.0014453000
_diffrn_orient_matrix_UB_12      0.0177552000
_diffrn_orient_matrix_UB_13      0.0503481000
_diffrn_orient_matrix_UB_21      0.0396758000
_diffrn_orient_matrix_UB_22      0.0912498000
_diffrn_orient_matrix_UB_23      -0.0014878000
_diffrn_orient_matrix_UB_31      -0.1066616000
_diffrn_orient_matrix_UB_32      -0.0061002000
_diffrn_orient_matrix_UB_33      -0.0063767000
_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_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            50232
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.267
_diffrn_reflns_theta_min         2.672
_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    25.534
_exptl_absorpt_correction_T_max  0.222
_exptl_absorpt_correction_T_min  0.021
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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    1.685
_exptl_crystal_description       block
_exptl_crystal_F_000             3536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         5.020
_refine_diff_density_min         -2.638
_refine_diff_density_rms         0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1455
_refine_ls_number_reflns         50232
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.356
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0922
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2964
_refine_ls_wR_factor_ref         0.3070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                42687
_reflns_number_total             50232
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9820\% 
around [0.89 -0.45 -0.00] (reciprocal) or [1.00 -0.01 0.01] (direct)
;
_cod_data_source_file            lt5059.cif
_cod_data_source_block           PBA-2_6-Iodine_CrystallineSponge
_cod_original_formula_sum        'C22.86 H16.22 I3.75 N6 O0.37 Zn1.50'
_cod_database_code               1569422
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula
'(Zn3 I6 N12 H24 C36) (C13 H10 I2 O)2 (C6 H12)2'
_chemical_oxdiff_usercomment     'Diiodo Biaryl'
_shelx_estimated_absorpt_t_max   0.268
_shelx_estimated_absorpt_t_min   0.053
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5040(11)
 0.4960(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C13B-C8B
 1.54 with sigma of 0.02
 O1B-C5B
 1.38 with sigma of 0.02
 I509-Zn55 \\sim I409-Zn45
 with sigma of 0.02
 I510-I509 \\sim I410-I309
 with sigma of 0.02
 I401-N324 \\sim I301-N324
 with sigma of 0.04
 Zn55-N312 \\sim Zn35-N312 \\sim Zn45-N312
 with sigma of 0.02
 I510-Zn55 \\sim I410-Zn45
 with sigma of 0.02
 Zn55-N313 \\sim Zn45-N313
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C13B \\sim I2B \\sim C6B \\sim C5B \\sim C1B \\sim C4B \\sim O1B \\sim C2B
\\sim C7B \\sim C3B \\sim I1B \\sim C8B \\sim C12B \\sim C9B \\sim C11B \\sim
C10B: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 1.7A
Uanis(Zn36) = Uanis(Zn46)
5. Others
 1*[Sof(I304)+Sof(I303)+Sof(I311)+Sof(I312)+Sof(Zn32)+Sof(Zn36)+Sof(Zn42)+
 Sof(I403)+Sof(I404)]+1*[Sof(Zn46)+Sof(I411)+Sof(I412)]+1*[Sof(H350)+Sof(H354)+
 Sof(I512)+Sof(I511)+Sof(Zn56)]=1 with esd of 0.00001
 Sof(Zn42)=Sof(I403)=Sof(I404)=1-FVAR(1)
 Sof(I304)=Sof(I303)=Sof(I311)=Sof(I312)=Sof(Zn32)=Sof(Zn36)=FVAR(1)
 Sof(Zn46)=Sof(I411)=Sof(I412)=FVAR(2)
 Sof(H350)=Sof(H354)=1-FVAR(3)
 Sof(I512)=Sof(I511)=Sof(Zn56)=FVAR(3)
 Sof(Zn44)=Sof(I407)=Sof(I408)=1-FVAR(4)
 Sof(I307)=Sof(I308)=Sof(Zn34)=FVAR(4)
 Fixed Sof: I401(0.34602) I410(0.46338) I2A(0.87453) I402(0.34602)
 I405(0.33937) I406(0.33937) I409(0.46338) I1A(0.87453) Zn41(0.34602)
 Zn43(0.33937) Zn45(0.46338) I2B(0.62) I1B(0.62) O1A(0.87453) H1A(0.87453)
 C1A(0.87453) H1AA(0.87453) C6A(0.87453) C5A(0.87453) C4A(0.87453) C3A(0.87453)
 H3A(0.87453) C2A(0.87453) C13A(0.87453) H13A(0.87453) H13B(0.87453)
 H13C(0.87453) C7A(0.87453) C12A(0.87453) H12A(0.87453) C11A(0.87453)
 H11A(0.87453) C10A(0.87453) H10A(0.87453) C9A(0.87453) H9A(0.87453)
 C8A(0.87453) C7B(0.62) C8B(0.62) C9B(0.62) H9B(0.62) C10B(0.62) H10B(0.62)
 C11B(0.62) H11B(0.62) C12B(0.62) H12B(0.62) C2B(0.62) C1B(0.62) H1B(0.62)
 C6B(0.62) C5B(0.62) C4B(0.62) C3B(0.62) H3B(0.62) O1B(0.62) H1BA(0.62)
 I306(0.59391) Zn33(0.59391) I305(0.59391) I301(0.65398) Zn31(0.65398)
 I302(0.65398) I506(0.06673) I505(0.06673) Zn53(0.06673) C13B(0.62) H13D(0.62)
 H13E(0.62) H13F(0.62) Zn35(0.52026) I310(0.52026) I309(0.52026) I510(0.01635)
 I509(0.01635) Zn55(0.01635)
 Fixed Uiso: I506(0.08) I505(0.08) Zn53(0.08) I512(0.08) I511(0.08) Zn56(0.08)
 I510(0.08) I509(0.08) Zn55(0.08)
6.a Aromatic/amide H refined with riding coordinates:
 N321(H321), N320(H320), C336(H336), C341(H341), C323(H323), C359(H359),
 C320(H32A), C302(H302), C368(H368), C305(H305), C337(H337), C351(H351),
 C322(H322), C329(H329), C350(H350), C319(H319), C365(H365), C346(H346),
 C1A(H1AA), C3A(H3A), C335(H335), C347(H347), C358(H358), C355(H355),
 C349(H349), C301(H301), C356(H356), C333(H333), C340(H340), C369(H369),
 C310(H310), C353(H353), C372(H372), C312(H312), C318(H318), C354(H354),
 C328(H328), C313(H313), C311(H311), C304(H304), C12A(H12A), C11A(H11A),
 C10A(H10A), C9A(H9A), C332(H332), C371(H371), C364(H364), C330(H330),
 C348(H348), C315(H315), C338(H338), C317(H317), C331(H331), C366(H366),
 C314(H314), C367(H367), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B), C1B(H1B),
  C3B(H3B)
6.b Fitted hexagon refined as free rotating group:
 C1A(C6A,C5A,C4A,C3A,C2A), C7A(C12A,C11A,C10A,C9A,C8A), C7B(C8B,C9B,C10B,C11B,
 C12B), C2B(C1B,C6B,C5B,C4B,C3B)
6.c Tetrahedral OH refined with everything fixed:
 O1A(H1A), O1B(H1BA)
6.d Idealised Me refined with everything fixed:
 C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F)
;
_shelx_res_checksum              55695
_shelx_hkl_checksum              39662
_olex2_date_sample_data_collection 2022-05-06
_olex2_date_sample_submission    2022-05-06
_olex2_submission_original_sample_id 'Phenyl Biaryl Alcohol-2,6-Iodine'
_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 3.516
_oxdiff_exptl_absorpt_empirical_full_min 0.387
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2