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_1569418
_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, 0.837(C16 H18 O4), 0.833(C6 H12)'
_chemical_formula_sum            'C54.39 H49.06 I6 N12 O3.35 Zn3'
_chemical_formula_weight         1881.81
_chemical_name_common
'Benzyl Biaryl Alcohol-8,10,12-Methoxy (absorbed in crystalline sponge)'
_chemical_name_systematic
'(2',4',6'-trimethoxy-[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                 101.400(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.533(3)
_cell_length_b                   15.0103(9)
_cell_length_c                   30.9081(14)
_cell_measurement_reflns_used    7534
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9770
_cell_measurement_theta_min      3.4140
_cell_volume                     15705.2(18)
_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 10.0000
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000HE'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.937
_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   -105.00 -54.00   0.50    1.20    -- -103.00 102.00 -37.00  102
  2  \w   -160.00 -88.00   0.50    1.20    -- -103.00-102.00-140.00  144
  3  \w    -57.00 -31.00   0.50    1.20    -- -103.00  61.00-180.00   52
  4  \w   -157.00 -90.00   0.50    1.20    -- -103.00 -61.00 150.00  134
  5  \w   -115.00 -89.00   0.50    1.20    -- -103.00 -61.00 -90.00   52
  6  \w    -69.00 -43.00   0.50    1.20    -- -103.00  61.00 -90.00   52
  7  \w   -170.00-131.00   0.50    1.20    -- -103.00 -61.00 -90.00   78
  8  \w     32.00 105.00   0.50    1.20    --  101.75-102.00-140.00  146
  9  \w    110.00 137.00   0.50    1.20    --  101.75 102.00 -37.00   54
 10  \w     90.00 138.00   0.50    1.20    --  101.75 125.00  30.00   96
 11  \w     86.00 112.00   0.50    1.20    --  101.75  61.00 -60.00   52
 12  \w     29.00  54.00   0.50    1.20    --  101.75 -61.00 -60.00   50
 13  \w     31.00  72.00   0.50    1.20    --  101.75 -61.00-120.00   82
 14  \w     34.00  68.00   0.50    1.20    --  101.75 -61.00   0.00   68
 15  \w     31.00  72.00   0.50    1.20    --  101.75 -61.00 -90.00   82
 16  \w    145.00 175.00   0.50    1.20    --  101.75  61.00 -60.00   60
 17  \w     29.00  72.00   0.50    1.20    --  101.75 -61.00  60.00   86
 18  \w    146.00 171.00   0.50    1.20    --  101.75 125.00  30.00   50
 19  \w    -80.00   3.00   0.50    0.30    --  -46.01 102.00 -37.00  166
 20  \w     40.00  65.00   0.50    0.30    --   46.01-102.00-140.00   50
 21  \w   -116.00 -31.00   0.50    0.30    --  -46.01 -57.00-150.00  170
 22  \w   -112.00 -32.00   0.50    0.30    --  -46.01 -57.00 120.00  160
;
_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      -0.0397736000
_diffrn_orient_matrix_UB_12      -0.0017292000
_diffrn_orient_matrix_UB_13      -0.0330060000
_diffrn_orient_matrix_UB_21      -0.0069504000
_diffrn_orient_matrix_UB_22      0.0983690000
_diffrn_orient_matrix_UB_23      0.0104373000
_diffrn_orient_matrix_UB_31      0.0210124000
_diffrn_orient_matrix_UB_32      0.0291492000
_diffrn_orient_matrix_UB_33      -0.0372498000
_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  0.0541
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            46392
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.985
_diffrn_reflns_theta_min         2.611
_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 007 HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    19.921
_exptl_absorpt_correction_T_max  0.485
_exptl_absorpt_correction_T_min  0.071
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.592
_exptl_crystal_description       block
_exptl_crystal_F_000             7153
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.011
_refine_diff_density_min         -1.517
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1010
_refine_ls_number_reflns         15173
_refine_ls_number_restraints     521
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.1172
_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^)+(0.0469P)^2^+983.2523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2681
_refine_ls_wR_factor_ref         0.2736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12409
_reflns_number_total             15173
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5059.cif
_cod_data_source_block           BBA-8_10_12-Methoxy_CrystallineSponge
_cod_original_cell_volume        15705.3(17)
_cod_database_code               1569418
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         '(Zn3 I6 N12 H24 C36) (C16 H17 O3)2 (C6 H12)2'
_chemical_oxdiff_usercomment     9444-86
_shelx_estimated_absorpt_t_max   0.336
_shelx_estimated_absorpt_t_min   0.061
_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
 C7B-C4B
 1.54 with sigma of 0.02
 C812-C811 = C812-C807 = C811-C810 = C810-C809 = C809-C808 = C808-C807
 1.54 with sigma of 0.02
 O1B-C13B
 1.43 with sigma of 0.02
 C13B-C5B
 1.54 with sigma of 0.02
 C7A-C4A
 1.54 with sigma of 0.02
 O4B-C10B
 1.43 with sigma of 0.02
 O2B-C8B
 1.43 with sigma of 0.02
 O3B-C12B
 1.43 with sigma of 0.02
 C5A-C13A
 1.54 with sigma of 0.02
 O4B-C16B
 1.43 with sigma of 0.02
 O2B-C14B
 1.43 with sigma of 0.02
 O3A-C15A
 1.54 with sigma of 0.02
 O4A-C16A
 1.54 with sigma of 0.02
 C806-C801 = C806-C805 = C801-C802 = C802-C803 = C803-C804 = C804-C805
 1.54 with sigma of 0.02
 C812-C810 = C812-C808 = C811-C809 = C810-C808 = C809-C807
 2.54 with sigma of 0.04
 C7A-O2A
 2.4 with sigma of 0.04
 C9A-O4A
 2.4 with sigma of 0.04
 C9A-O2A
 2.4 with sigma of 0.04
 C11A-O4A
 2.4 with sigma of 0.04
 C10B-C16B
 2.4 with sigma of 0.04
 C806-C802 = C806-C804 = C801-C803 = C802-C804 = C803-C805
 2.54 with sigma of 0.04
 C8A-C4A \\sim C4A-C12A
 with sigma of 0.04
 C812-C808 \\sim C810-C808 \\sim C811-C807 \\sim C811-C809 \\sim C809-C807
\\sim C812-C810
 with sigma of 0.04
 C812-C811 \\sim C811-C810 \\sim C810-C809 \\sim C809-C808 \\sim C808-C807
\\sim C807-C812
 with sigma of 0.02
 C3A-C7A \\sim C7A-C5A
 with sigma of 0.04
 C5B-C7B \\sim C7B-C3B
 with sigma of 0.04
 C12B-C4B \\sim C4B-C8B
 with sigma of 0.04
 I305-Zn33 \\sim I405-Zn43
 with sigma of 0.02
 I306-Zn33 \\sim I406-Zn43
 with sigma of 0.02
 I306-N307 \\sim I406-N307
 with sigma of 0.04
 Zn33-N306 \\sim Zn43-N306
 with sigma of 0.02
 Zn33-N307 \\sim Zn43-N307
 with sigma of 0.02
 I306-N306 \\sim I406-N306
 with sigma of 0.04
 I305-I306 \\sim I405-I406
 with sigma of 0.04
 I305-N306 \\sim I405-N306
 with sigma of 0.04
 I305-N307 \\sim I405-N307
 with sigma of 0.04
 I304-N305 \\sim I404-N305
 with sigma of 0.04
 I303-I304 \\sim I403-I404
 with sigma of 0.04
 I303-Zn32 \\sim I403-Zn42
 with sigma of 0.02
 I303-N305 \\sim I403-N305
 with sigma of 0.04
 I304-Zn32 \\sim I404-Zn42
 with sigma of 0.02
 Zn32-N305 \\sim Zn42-N305
 with sigma of 0.02
 I401-N301 \\sim I301-N301
 with sigma of 0.04
 I402-N301 \\sim I302-N301
 with sigma of 0.04
 I401-I402 \\sim I301-I302
 with sigma of 0.04
 I401-Zn41 \\sim I301-Zn31
 with sigma of 0.02
 I402-Zn41 \\sim I302-Zn31
 with sigma of 0.02
 Zn41-N301 \\sim Zn31-N301
 with sigma of 0.02
 C806-C801 \\sim C801-C802 \\sim C802-C803 \\sim C803-C804 \\sim C804-C805
\\sim C805-C806
 with sigma of 0.02
 C806-C804 \\sim C802-C804 \\sim C801-C805 \\sim C801-C803 \\sim C803-C805
\\sim C806-C802
 with sigma of 0.04
3. Restrained planarity
 C4B, C5B, C6B, C13B
 with sigma of 0.05
4. Uiso/Uaniso restraints and constraints
C812 \\sim C811 \\sim C810 \\sim C809 \\sim C808 \\sim C807: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
C5B \\sim O4B \\sim C16B \\sim C10B \\sim C11B \\sim C9B \\sim C12B \\sim C8B
\\sim C7B \\sim O3B \\sim O2B \\sim C4B \\sim C15B \\sim C14B \\sim C3B \\sim
C6B \\sim C13B \\sim C2B \\sim C1B \\sim O1B: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
C9A \\sim C4A \\sim C5A \\sim C3A \\sim C7A \\sim C6A \\sim C13A \\sim C2A
\\sim C12A \\sim C8A \\sim C1A \\sim O1A \\sim O3A \\sim C11A \\sim O2A \\sim
C15A \\sim C10A \\sim C14A \\sim O4A \\sim C16A: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
C809 \\sim C812 \\sim C811 \\sim C807 \\sim C810 \\sim C808: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C806 \\sim C801 \\sim C802 \\sim C803 \\sim C804 \\sim C805: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C801 \\sim C806 \\sim C805 \\sim C802 \\sim C804 \\sim C803: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(Zn31) = Uanis(Zn41)
5. Rigid body (RIGU) restrains
 C812, C811, C810, C809, C808, C807
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C806, C801, C802, C803, C804, C805
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(I404)=Sof(Zn42)=Sof(I403)=1-FVAR(1)
 Sof(I303)=Sof(I304)=Sof(Zn32)=FVAR(1)
 Fixed Sof: I401(0.24329) I402(0.24329) I305(0.58072) I306(0.58072)
 Zn41(0.24329) Zn33(0.58072) I405(0.41928) Zn43(0.41928) I406(0.41928)
 I302(0.75671) Zn31(0.75671) I301(0.75671) C4A(0.42293) C5A(0.42293)
 C6A(0.42293) H6A(0.42293) C1A(0.42293) H1A(0.42293) C2A(0.42293) H2A(0.42293)
 C3A(0.42293) H3A(0.42293) O2A(0.42293) O4A(0.42293) O3A(0.42293) C10A(0.42293)
 C11A(0.42293) H11A(0.42293) C12A(0.42293) C7A(0.42293) C8A(0.42293)
 C9A(0.42293) H9A(0.42293) C14A(0.42293) H14A(0.42293) H14B(0.42293)
 H14C(0.42293) C16A(0.42293) H16A(0.42293) H16B(0.42293) H16C(0.42293)
 C15A(0.42293) H15A(0.42293) H15B(0.42293) H15C(0.42293) O4B(0.41393)
 O2B(0.41393) C16B(0.41393) H16D(0.41393) H16E(0.41393) H16F(0.41393)
 C14B(0.41393) H14D(0.41393) H14E(0.41393) H14F(0.41393) C7B(0.41393)
 C12B(0.41393) C11B(0.41393) H11B(0.41393) C10B(0.41393) C9B(0.41393)
 H9B(0.41393) C8B(0.41393) O3B(0.41393) C4B(0.41393) C5B(0.41393) C6B(0.41393)
 H6B(0.41393) C1B(0.41393) H1B(0.41393) C2B(0.41393) H2B(0.41393) C3B(0.41393)
 H3B(0.41393) C15B(0.41393) H15D(0.41393) H15E(0.41393) H15F(0.41393)
 O1B(0.41393) H1BA(0.41393) C13B(0.41393) H13C(0.41393) H13D(0.41393)
 C13A(0.42293) H13A(0.42293) H13B(0.42293) O1A(0.42293) H1AA(0.42293)
 C806(0.53341) H80A(0.53341) H80B(0.53341) C801(0.53341) H80C(0.53341)
 H80D(0.53341) C802(0.53341) H80E(0.53341) H80F(0.53341) C803(0.53341)
 H80G(0.53341) H80H(0.53341) C804(0.53341) H80I(0.53341) H80J(0.53341)
 C805(0.53341) H80K(0.53341) H80L(0.53341) C812(0.29927) H81A(0.29927)
 H81B(0.29927) C811(0.29927) H81C(0.29927) H81D(0.29927) C810(0.29927)
 H81E(0.29927) H81F(0.29927) C809(0.29927) H80M(0.29927) H80N(0.29927)
 C808(0.29927) H80O(0.29927) H80P(0.29927) C807(0.29927) H80Q(0.29927)
 H80R(0.29927)
7.a Secondary CH2 refined with riding coordinates:
 C13B(H13C,H13D), C13A(H13A,H13B), C806(H80A,H80B), C801(H80C,H80D), C802(H80E,
 H80F), C803(H80G,H80H), C804(H80I,H80J), C805(H80K,H80L), C812(H81A,H81B),
 C811(H81C,H81D), C810(H81E,H81F), C809(H80M,H80N), C808(H80O,H80P), C807(H80Q,
 H80R)
7.b Aromatic/amide H refined with riding coordinates:
 C304(H304), C320(H320), C329(H329), C319(H319), C322(H322), C328(H328),
 C318(H318), C302(H302), C317(H317), C335(H335), C301(H301), C305(H305),
 C336(H336), C315(H315), C314(H314), C333(H333), C323(H323), C310(H310),
 C311(H311), C331(H331), C312(H312), C330(H330), C332(H332), C313(H313),
 C6A(H6A), C1A(H1A), C2A(H2A), C3A(H3A), C11A(H11A), C9A(H9A), C11B(H11B),
 C9B(H9B), C6B(H6B), C1B(H1B), C2B(H2B), C3B(H3B)
7.c Fitted hexagon refined as free rotating group:
 C4A(C5A,C6A,C1A,C2A,C3A), C10A(C11A,C12A,C7A,C8A,C9A), C7B(C12B,C11B,C10B,C9B,
 C8B), C4B(C5B,C6B,C1B,C2B,C3B)
7.d Tetrahedral OH refined with everything fixed:
 O1B(H1BA), O1A(H1AA)
7.e Idealised Me refined with everything fixed:
 C14A(H14A,H14B,H14C), C16A(H16A,H16B,H16C), C15A(H15A,H15B,H15C), C16B(H16D,
 H16E,H16F), C14B(H14D,H14E,H14F), C15B(H15D,H15E,H15F)
;
_shelx_res_checksum              99972
_shelx_hkl_checksum              95086
_olex2_date_sample_data_collection 2023-01-16
_olex2_date_sample_submission    2023-01-16
_olex2_submission_original_sample_id 'Benzyl Biaryl Alcohol-8,10,12-Methoxy'
_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 2.461
_oxdiff_exptl_absorpt_empirical_full_min 0.383