Controllable π-π coupling of intramolecular dimer models in aggregated states.
Liao, Qiuyan; Li, Aisen; Huang, Arui; Wang, Jiaqiang; Chang, Kai; Li, Hehua; Yao, Pengfei; Zhong, Cheng; Xie, Peidong; Wang, Jinfeng; Li, Zhen; Li, Qianqian; Chemical science 15 (2024) 4364–4373; doi:10.1039/d3sc05533g

data_1570875
_publ_section_title
;
 Controllable &#x3c0;-&#x3c0; coupling of intramolecular dimer models in
 aggregated states.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              4364
_journal_page_last               4373
_journal_paper_doi               10.1039/d3sc05533g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C2 H5 I1, C51 H46 O'
_chemical_formula_sum            'C53 H51 I O'
_chemical_formula_weight         830.84
_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             2023-11-15
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-11-15 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                93.947(2)
_cell_angle_beta                 113.886(2)
_cell_angle_gamma                108.270(2)
_cell_formula_units_Z            2
_cell_length_a                   12.8029(2)
_cell_length_b                   13.1018(2)
_cell_length_c                   15.0559(3)
_cell_measurement_reflns_used    13256
_cell_measurement_temperature    302.47(10)
_cell_measurement_theta_max      75.1660
_cell_measurement_theta_min      3.2650
_cell_volume                     2136.32(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.47(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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     35.00  61.00   0.50    0.20    --   76.75-125.00  30.00   52
  2  \w     71.00  97.00   0.50    0.20    --   76.75-125.00  30.00   52
  3  \w     41.00  96.00   0.50    0.20    --   77.87-120.00  -8.23  110
  4  \w     49.00  75.00   0.50    0.20    --   76.75-125.00 -30.00   52
  5  \w     28.00  65.00   0.50    0.20    --   62.89-125.00 -30.00   74
  6  \w     47.00  96.00   0.50    0.20    --   76.75-125.00 -90.00   98
  7  \w     52.00  98.00   0.50    0.20    --   76.75-125.00-150.00   92
  8  \w     52.00 102.00   0.50    0.20    --   62.89  15.00-180.00  100
  9  \w     63.00 110.00   0.50    0.20    --   72.93  15.00 120.00   94
 10  \w   -106.00 -61.00   0.50    0.20    --  -63.72 -15.00 -90.00   90
 11  \w    -88.00 -63.00   0.50    0.20    --  -71.74 -15.00-120.00   50
 12  \w    -99.00 -57.00   0.50    0.20    --  -63.72 -15.00 -30.00   84
 13  \w    -98.00 -72.00   0.50    0.20    --  -76.43 -15.00-150.00   52
 14  \w    -91.00 -54.00   0.50    0.20    --  -63.72 -15.00   0.00   74
 15  \w   -114.00 -64.00   0.50    0.20    --  -71.74 -15.00  60.00  100
 16  \w   -119.00 -83.00   0.50    0.20    --  -76.43 -15.00 120.00   72
 17  \w    -85.00 -59.00   0.50    0.20    --  -63.72 -15.00 120.00   52
 18  \w   -125.00 -79.00   0.50    0.20    --  -81.49 -15.00 150.00   92
 19  \w   -124.00 -74.00   0.50    0.20    --  -81.49 -15.00 -60.00  100
 20  \w   -125.00 -77.00   0.50    0.20    --  -81.49 -15.00-120.00   96
 21  \w   -118.00 -66.00   0.50    0.20    --  -76.43 -15.00-180.00  104
 22  \w   -102.00 -43.00   0.50    0.20    --  -81.49 125.00-150.00  118
 23  \w    -53.00 -26.00   0.50    0.20    --  -63.72 125.00-180.00   54
 24  \w    -72.00 -29.00   0.50    0.20    --  -71.74 125.00 -30.00   86
 25  \w    -94.00 -52.00   0.50    0.20    --  -76.43 125.00   0.00   84
 26  \w   -102.00 -41.00   0.50    0.20    --  -81.49 125.00  60.00  122
 27  \w    -97.00 -34.00   0.50    0.20    --  -76.43 125.00  90.00  126
 28  \w   -101.00 -75.00   0.50    0.20    --  -81.49 125.00 120.00   52
 29  \w    -68.00 -40.00   0.50    0.20    --  -81.49 125.00 120.00   56
 30  \w   -102.00 -47.00   0.50    0.20    --  -81.49 125.00 150.00  110
 31  \w   -100.00 -74.00   0.50    0.20    --  -81.49 125.00  90.00   52
 32  \w   -102.00 -40.00   0.50    0.20    --  -81.49 125.00  30.00  124
 33  \w    -68.00 -42.00   0.50    0.20    --  -81.49 125.00   0.00   52
 34  \w   -102.00 -77.00   0.50    0.20    --  -81.49 125.00   0.00   50
 35  \w   -101.00 -43.00   0.50    0.20    --  -81.49 125.00 -60.00  116
 36  \w   -102.00 -77.00   0.50    0.20    --  -81.49 125.00 -90.00   50
 37  \w   -102.00 -76.00   0.50    0.20    --  -81.49 125.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0399536000
_diffrn_orient_matrix_UB_12      -0.0015498000
_diffrn_orient_matrix_UB_13      0.0837946000
_diffrn_orient_matrix_UB_21      -0.0819452000
_diffrn_orient_matrix_UB_22      -0.1231714000
_diffrn_orient_matrix_UB_23      -0.0442770000
_diffrn_orient_matrix_UB_31      0.1087549000
_diffrn_orient_matrix_UB_32      -0.0313132000
_diffrn_orient_matrix_UB_33      0.0648990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26596
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.295
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       plate
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.279
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         7478
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0890
_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          0.2625
_refine_ls_wR_factor_ref         0.2771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5762
_reflns_number_total             7478
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05533g4.cif
_cod_data_source_block           20221209-lqy-1_auto
_cod_depositor_comments
'Adding full bibliography for 1570870--1570891.cif.'
_cod_original_cell_volume        2136.31(7)
_cod_database_code               1570875
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOI
_shelx_estimated_absorpt_t_max   0.578
_shelx_estimated_absorpt_t_min   0.458
_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
2. Restrained distances
 C52-C53
 1.54 with sigma of 0.02
 C52-I1'
 2.13 with sigma of 0.02
 C52'-I1
 2.13 with sigma of 0.02
 C52'-C53'
 1.54 with sigma of 0.02
 C53'-C52'
 1.54 with sigma of 0.01
 I1'-C52 \\sim I1-C52'
 with sigma of 0.02
 I1'-C53 \\sim I1-C53'
 with sigma of 0.04
 C53-C52 \\sim C53'-C52'
 with sigma of 0.02
3. Others
 Sof(I1)=Sof(C52')=Sof(H52A)=Sof(H52B)=Sof(C53')=Sof(H53A)=Sof(H53B)=Sof(H53C)=
 1-FVAR(1)
 Sof(I1')=Sof(C52)=Sof(H52C)=Sof(H52D)=Sof(C53)=Sof(H53D)=Sof(H53E)=Sof(H53F)=
 FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C52(H52C,H52D), C52'(H52A,H52B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31),
  C32(H32), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39)
4.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C46(H46A,H46B,
 H46C), C47(H47A,H47B,H47C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C51(H51A,
 H51B,H51C), C53(H53D,H53E,H53F), C53'(H53A,H53B,H53C)
;
_shelx_res_checksum              55073
_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 3.606
_oxdiff_exptl_absorpt_empirical_full_min 0.336