Guest-Binding-Induced Interhetero Hosts Charge Transfer Crystallization: Selective Coloration of Commonly Used Organic Solvents.
Mi, Yan; Ma, Jingyu; Liang, Wenting; Xiao, Chao; Wu, Wanhua; Zhou, Dayang; Yao, Jiabin; Sun, Wenjia; Sun, Junliang; Gao, Guowei; Chen, Xiaochuan; Chruma, Jason J.; Yang, Cheng; Journal of the American Chemical Society 143 (2021) 1553–1561; doi:10.1021/jacs.0c11833

data_4135617
_publ_section_title
;
 Guest-Binding-Induced Interhetero Hosts Charge Transfer Crystallization:
 Selective Coloration of Commonly Used Organic Solvents.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1553
_journal_page_last               1561
_journal_paper_doi               10.1021/jacs.0c11833
_journal_volume                  143
_journal_year                    2021
_chemical_formula_moiety
'C45 H50 O10, C35 H20 O10, 3(C2 H3 O2), 2(C2 H4 O2)'
_chemical_formula_sum            'C91 H0.5 O29'
_chemical_formula_weight         1557.41
_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             2020-06-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                83.590(2)
_cell_angle_beta                 75.478(2)
_cell_angle_gamma                70.196(2)
_cell_formula_units_Z            2
_cell_length_a                   12.0109(3)
_cell_length_b                   16.9861(4)
_cell_length_c                   21.9656(4)
_cell_measurement_reflns_used    19464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4260
_cell_measurement_theta_min      2.7590
_cell_volume                     4079.88(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_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    -74.00  -3.00   0.50    0.61    --  -35.00 -38.00-120.00  142
  2  \w    -78.00  39.00   0.50    0.61    --  -35.00  82.00  30.00  234
  3  \w    -39.00   8.00   0.50    0.61    --  -35.00 -82.00 -60.00   94
  4  \w    -33.00   8.00   0.50    0.61    --  -35.00 -82.00-180.00   82
  5  \w    -78.00  53.00   0.50    0.61    --  -35.00  38.00 -60.00  262
  6  \w     79.00 121.00   0.50    0.61    --   43.40  77.00  60.00   84
  7  \w     25.00  77.00   0.50    0.61    --   43.40 -57.00  60.00  104
  8  \w    -42.00  13.00   0.50    0.61    --   43.40 -57.00  60.00  110
  9  \w      2.00  49.00   0.50    0.61    --   43.40  77.00 -30.00   94
 10  \w     82.00 127.00   0.50    0.61    --   43.40  82.00 -30.00   90
 11  \w     82.00 133.00   0.50    0.61    --   43.40  82.00  30.00  102
 12  \w     14.00  40.00   0.50    0.61    --   58.00  81.00  85.56   52
 13  \w     14.00  39.00   0.50    0.61    --   58.00  81.00 -78.62   50
 14  \w     14.00  39.00   0.50    0.61    --   58.00  81.00  -7.96   50
 15  \w     15.00  40.00   0.50    0.61    --   58.00  80.00 112.19   50
 16  \w     26.00  54.00   0.50    0.61    --   66.00  75.00 172.63   56
 17  \w     30.00  55.00   0.50    0.61    --   70.00  75.00 136.90   50
 18  \w     30.00  55.00   0.50    0.61    --   70.00  75.00 -42.73   50
 19  \w     30.00  55.00   0.50    0.61    --   70.00  75.00   0.49   50
 20  \w     30.00  55.00   0.50    0.61    --   70.00  75.00  18.74   50
 21  \w     30.00  55.00   0.50    0.61    --   70.00  75.00-162.36   50
 22  \w     30.00  56.00   0.50    0.61    --   70.00  75.00-126.65   52
 23  \w     35.00  60.00   0.50    0.61    --   74.00  74.00-110.12   50
 24  \w     35.00  60.00   0.50    0.61    --   74.00  74.00  92.41   50
 25  \w     40.00  67.00   0.50    2.42    --   78.00  73.00  35.65   54
 26  \w    116.00 142.00   0.50    2.42    --   82.00  73.00 -89.33   52
 27  \w    143.00 170.00   0.50    2.42    --   82.00  71.00 140.54   54
 28  \w     46.00  92.00   0.50    2.42    --   82.00  71.00 140.54   92
 29  \w     43.00  71.00   0.50    2.42    --   82.00  73.00 -89.33   56
 30  \w     45.00  77.00   0.50    2.42    --   82.00  71.00  89.13   64
 31  \w     47.00  90.00   0.50    2.42    --   86.00  73.00 -11.23   86
 32  \w     49.00  81.00   0.50    2.42    --   86.00  71.00-162.22   64
 33  \w     51.00  96.00   0.50    2.42    --   90.00  73.00 159.24   90
 34  \w    119.00 182.00   0.50    2.42    --   94.00  72.00 -58.07  126
 35  \w     56.00  92.00   0.50    2.42    --   94.00  72.00 -58.07   72
 36  \w     57.00  88.00   0.50    2.42    --   94.00  70.00-126.35   62
 37  \w     62.00 111.00   0.50    2.42    --   98.00  69.00 -40.79   98
 38  \w     66.00 157.00   0.50    2.42    --   98.00  67.00 -80.42  182
 39  \w    122.00 166.00   0.50    2.42    --   98.00  71.00 108.67   88
 40  \w     61.00 101.00   0.50    2.42    --   98.00  71.00 108.67   80
 41  \w    154.00 186.00   0.50    2.42    --   98.00  73.00  19.27   64
 42  \w    110.00 144.00   0.50    2.42    --   98.00  73.00  19.27   68
 43  \w     59.00  91.00   0.50    2.42    --   98.00  73.00  19.27   64
 44  \w    156.00 187.00   0.50    2.42    --   98.00  69.00 -40.79   62
 45  \w    116.00 152.00   0.50    2.42    --   98.00  69.00 -40.79   72
 46  \w     63.00 167.00   0.50    2.42    --  102.00  73.00  33.75  208
 47  \w     66.00 186.00   0.50    2.42    --  102.00  68.00-163.35  240
 48  \w     77.00 161.00   0.50    2.42    --  109.30  61.00 150.00  168
 49  \w    144.00 197.00   0.50    2.42    --  109.30  74.00 156.01  106
 50  \w     51.00 136.00   0.50    2.42    --  109.30 -82.00 150.00  170
 51  \w     70.00  99.00   0.50    2.42    --  109.30  74.00 156.01   58
 52  \w     23.00  48.00   0.50    2.42    --  109.30 -82.00 150.00   50
 53  \w     73.00 199.00   0.50    2.42    --  109.30  75.00 -14.44  252
 54  \w     22.00 137.00   0.50    2.42    --  109.30 -82.00   0.00  230
 55  \w     75.00 189.00   0.50    2.42    --  109.30  63.00-102.93  228
 56  \w     70.00 188.00   0.50    2.42    --  109.30  73.00  53.49  236
 57  \w    117.00 199.00   0.50    2.42    --  109.30  67.00  72.34  164
 58  \w     75.00 112.00   0.50    2.42    --  109.30  67.00  72.34   74
 59  \w    159.00 195.00   0.50    2.42    --  109.30  58.00 137.21   72
 60  \w     76.00 152.00   0.50    2.42    --  109.30  58.00 137.21  152
 61  \w     65.00 117.00   0.50    2.42    --  109.30 -82.00 -60.00  104
 62  \w     70.00 139.00   0.50    2.42    --  109.30 -82.00-150.00  138
 63  \w     76.00 186.00   0.50    2.42    --  109.30  77.00 -30.00  220
 64  \w     77.00 195.00   0.50    2.42    --  109.30  77.00-150.00  236
 65  \w     65.00 134.00   0.50    2.42    --  109.30 -82.00  60.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0566677000
_diffrn_orient_matrix_UB_12      -0.0087425000
_diffrn_orient_matrix_UB_13      -0.0534737000
_diffrn_orient_matrix_UB_21      0.0940397000
_diffrn_orient_matrix_UB_22      0.0319964000
_diffrn_orient_matrix_UB_23      -0.0479915000
_diffrn_orient_matrix_UB_31      0.0868728000
_diffrn_orient_matrix_UB_32      -0.0905546000
_diffrn_orient_matrix_UB_33      -0.0095337000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            87677
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.819
_diffrn_reflns_theta_min         2.766
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brown'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       plate
_exptl_crystal_F_000             1557
_refine_diff_density_max         1.233
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1098
_refine_ls_number_reflns         16423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.1160
_refine_ls_shift/su_max          4.449
_refine_ls_shift/su_mean         0.091
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1713P)^2^+13.5541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3463
_refine_ls_wR_factor_ref         0.3547
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13844
_reflns_number_total             16423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11833_si_003.cif
_cod_data_source_block           200626ct-hoac
_cod_original_cell_volume        4079.89(17)
_cod_original_formula_sum        'C91 H0.50 O29'
_cod_database_code               4135617
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C80 H70 O20'
_chemical_oxdiff_usercomment     -170C
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C80(H80A,H80B), C28(H28A,H28B), C71(H71A,H71B), C7(H7A,H7B),
 C53(H53A,H53B), C35(H35A,H35B), C44(H44A,H44B), C62(H62A,H62B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C40(H40), C73(H73), C46(H46), C23(H23), C37(H37), C16(H16),
 C67(H67), C49(H49), C26(H26), C5(H5), C9(H9), C76(H76), C64(H64), C30(H30),
 C55(H55), C58(H58), C2(H2), C12(H12), C33(H33)
2.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C51(H51A,H51B,H51C), C78(H78A,H78B,H78C), C52(H52A,H52B,
 H52C), C60(H60A,H60B,H60C), C84(H84A,H84B,H84C), C79(H79A,H79B,H79C), C69(H69A,
 H69B,H69C), C61(H61A,H61B,H61C), C42(H42A,H42B,H42C), C82(H82A,H82B,H82C),
 C70(H70A,H70B,H70C), C25(H25A,H25B,H25C), C88(H88A,H88B,H88C), C90(H90A,H90B,
 H90C)
2.d Idealised tetrahedral OH refined as rotating group:
 O28(H28), O30(H30A)
;
_shelx_res_checksum              77242
_shelx_hkl_checksum              25443
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.613