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_1570871
_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         'C51 H46 O, C3 H7 Br'
_chemical_formula_sum            'C54 H53 Br O'
_chemical_formula_weight         797.87
_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                94.104(2)
_cell_angle_beta                 114.041(3)
_cell_angle_gamma                108.338(2)
_cell_formula_units_Z            2
_cell_length_a                   12.8327(4)
_cell_length_b                   13.0654(3)
_cell_length_c                   15.2440(5)
_cell_measurement_reflns_used    12435
_cell_measurement_temperature    283(1)
_cell_measurement_theta_max      75.7200
_cell_measurement_theta_min      3.2230
_cell_volume                     2156.01(13)
_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      283(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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     52.00  95.00   0.50    0.30    --   62.89  15.00 -90.00   86
  2  \w     60.00 106.00   0.50    0.30    --   62.89  15.00-150.00   92
  3  \w     62.00 113.00   0.50    0.30    --   72.93  15.00-180.00  102
  4  \w    -71.00 -29.00   0.50    0.30    --  -71.74 125.00 -30.00   84
  5  \w    -97.00 -37.00   0.50    0.30    --  -76.43 125.00 -60.00  120
  6  \w   -102.00 -77.00   0.50    0.30    --  -81.49 125.00 -60.00   50
  7  \w    -56.00 -30.00   0.50    0.30    --  -71.74 125.00   0.00   52
  8  \w    -72.00 -30.00   0.50    0.30    --  -71.74 125.00  30.00   84
  9  \w   -102.00 -76.00   0.50    0.30    --  -81.49 125.00  60.00   52
 10  \w   -101.00 -75.00   0.50    0.30    --  -81.49 125.00 120.00   52
 11  \w   -101.00 -52.00   0.50    0.30    --  -81.49 125.00 150.00   98
 12  \w    -65.00 -30.00   0.50    0.30    --  -63.72 125.00 150.00   70
 13  \w   -102.00 -47.00   0.50    0.30    --  -81.49 125.00  90.00  110
 14  \w   -100.00 -74.00   0.50    0.30    --  -81.49 125.00  30.00   52
 15  \w   -102.00 -40.00   0.50    0.30    --  -81.49 125.00   0.00  124
 16  \w   -102.00 -75.00   0.50    0.30    --  -81.49 125.00 -30.00   54
 17  \w   -102.00 -61.00   0.50    0.30    --  -81.49 125.00 -90.00   82
 18  \w   -102.00 -49.00   0.50    0.30    --  -81.49 125.00-150.00  106
 19  \w   -107.00 -54.00   0.50    0.30    --  -63.72 -15.00-120.00  106
 20  \w   -103.00 -54.00   0.50    0.30    --  -63.72 -15.00-180.00   98
 21  \w   -101.00 -73.00   0.50    0.30    --  -71.74 -15.00-150.00   56
 22  \w   -112.00 -74.00   0.50    0.30    --  -81.49 -15.00 -90.00   76
 23  \w   -104.00 -65.00   0.50    0.30    --  -63.72 -15.00 -60.00   78
 24  \w   -124.00 -81.00   0.50    0.30    --  -81.49 -15.00 -30.00   86
 25  \w   -116.00 -67.00   0.50    0.30    --  -76.43 -15.00   0.00   98
 26  \w   -124.00 -72.00   0.50    0.30    --  -81.49 -15.00  60.00  104
 27  \w   -106.00 -81.00   0.50    0.30    --  -63.72 -15.00  90.00   50
 28  \w   -120.00 -94.00   0.50    0.30    --  -76.43 -15.00 120.00   52
 29  \w     33.00  74.00   0.50    0.30    --   62.89-125.00 150.00   82
 30  \w     34.00  74.00   0.50    0.30    --   62.89-125.00   0.00   80
 31  \w     40.00  98.00   0.50    0.30    --   76.75-125.00 -30.00  116
 32  \w     31.00  58.00   0.50    0.30    --   72.93-125.00 -60.00   54
 33  \w     37.00  96.00   0.50    0.30    --   76.75-125.00 -90.00  118
 34  \w     40.00  98.00   0.50    0.30    --   76.75-125.00-150.00  116
 35  \w     69.00  98.00   0.50    0.30    --   76.75-125.00  90.00   58
 36  \w     69.00  98.00   0.50    0.30    --   76.75-125.00 120.00   58
;
_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      0.1345623000
_diffrn_orient_matrix_UB_12      0.0528908000
_diffrn_orient_matrix_UB_13      0.0178131000
_diffrn_orient_matrix_UB_21      -0.0392335000
_diffrn_orient_matrix_UB_22      0.0629415000
_diffrn_orient_matrix_UB_23      -0.0815878000
_diffrn_orient_matrix_UB_31      0.0224344000
_diffrn_orient_matrix_UB_32      0.0976550000
_diffrn_orient_matrix_UB_33      0.0771888000
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25029
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         3.262
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61679
_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    1.229
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.031
_refine_diff_density_min         -1.594
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       0.0037(14)
_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   1.831
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         7518
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.899
_refine_ls_R_factor_all          0.1686
_refine_ls_R_factor_gt           0.1461
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4206
_refine_ls_wR_factor_ref         0.4423
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5406
_reflns_number_total             7518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05533g4.cif
_cod_data_source_block           20221124-3cbr_auto
_cod_depositor_comments
'Adding full bibliography for 1570870--1570891.cif.'
_cod_original_cell_volume        2156.01(12)
_cod_database_code               1570871
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOBr
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.798
_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
 C15-C1 = C54-C15
 1.54 with sigma of 0.01
 Br1-C54
 1.94 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(Br1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C54(H54A,H54B)
4.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C4(H4), C12(H12), C26(H26), C40(H40), C23(H23), C37(H37),
 C29(H29), C18(H18), C43(H43), C32(H32), C28(H28), C27(H27), C21(H21), C41(H41),
  C42(H42), C35(H35), C19(H19), C33(H33), C20(H20), C34(H34)
4.c Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C52(H52A,H52B,H52C), C45(H45A,H45B,H45C), C49(H49A,H49B,
 H49C), C50(H50A,H50B,H50C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C51(H51A,
 H51B,H51C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              89829
_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 4.417
_oxdiff_exptl_absorpt_empirical_full_min 0.131