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_1570885
_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, C2 H5 Br1'
_chemical_formula_sum            'C53 H51 Br O'
_chemical_formula_weight         783.84
_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                93.704(3)
_cell_angle_beta                 113.887(4)
_cell_angle_gamma                108.240(4)
_cell_formula_units_Z            2
_cell_length_a                   12.8123(5)
_cell_length_b                   13.0931(5)
_cell_length_c                   14.9329(5)
_cell_measurement_reflns_used    8465
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.3650
_cell_measurement_theta_min      3.2950
_cell_volume                     2121.92(17)
_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      273(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.990
_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     57.00  89.00   0.50    0.50    --   62.87  15.00 -90.00   64
  2  \w     76.00 116.00   0.50    0.50    --   72.70  15.00-150.00   80
  3  \w     67.00 111.00   0.50    0.50    --   76.90  15.00 -90.00   88
  4  \w     79.00 121.00   0.50    0.50    --   76.90  15.00 -60.00   84
  5  \w     61.00 101.00   0.50    0.50    --   72.70  15.00   0.00   80
  6  \w   -105.00 -54.00   0.50    0.50    --  -63.75 -15.00  30.00  102
  7  \w   -103.00 -58.00   0.50    0.50    --  -63.75 -15.00 -30.00   90
  8  \w   -103.00 -59.00   0.50    0.50    --  -63.75 -15.00 -90.00   88
  9  \w   -119.00 -88.00   0.50    0.50    --  -76.53 -15.00 -30.00   62
 10  \w   -114.00 -74.00   0.50    0.50    --  -81.41 -15.00   0.00   80
 11  \w    -96.00 -70.00   0.50    0.50    --  -76.53 -15.00  30.00   52
 12  \w   -125.00 -86.00   0.50    0.50    --  -81.41 -15.00  90.00   78
 13  \w   -113.00 -77.00   0.50    0.50    --  -81.41 -15.00 120.00   72
 14  \w    -82.00 -32.00   0.50    0.50    --  -63.75 125.00  30.00  100
 15  \w    -70.00 -29.00   0.50    0.50    --  -63.75 125.00 150.00   82
 16  \w    -97.00 -38.00   0.50    0.50    --  -76.53 125.00 120.00  118
 17  \w   -102.00 -76.00   0.50    0.50    --  -81.41 125.00 120.00   52
 18  \w    -97.00 -34.00   0.50    0.50    --  -76.53 125.00  60.00  126
 19  \w   -102.00 -48.00   0.50    0.50    --  -81.41 125.00   0.00  108
 20  \w   -102.00 -74.00   0.50    0.50    --  -81.41 125.00  30.00   56
 21  \w   -102.00 -54.00   0.50    0.50    --  -81.41 125.00  90.00   96
 22  \w    -99.00 -42.00   0.50    0.50    --  -81.41 125.00 -60.00  114
 23  \w   -102.00 -76.00   0.50    0.50    --  -81.41 125.00 -30.00   52
 24  \w   -102.00 -45.00   0.50    0.50    --  -81.41 125.00 -90.00  114
 25  \w    -68.00 -43.00   0.50    0.50    --  -81.41 125.00  30.00   50
 26  \w   -102.00 -76.00   0.50    0.50    --  -81.41 125.00-120.00   52
 27  \w    -64.00 -22.00   0.50    0.50    --  -63.75 125.00-150.00   84
 28  \w    -82.00 -39.00   0.50    0.50    --  -81.41 125.00-150.00   86
 29  \w   -102.00 -50.00   0.50    0.50    --  -81.41 125.00-180.00  104
 30  \w     37.00  98.00   0.50    0.50    --   76.90-125.00 -30.00  122
 31  \w     31.00  68.00   0.50    0.50    --   72.70-125.00  30.00   74
 32  \w     47.00  98.00   0.50    0.50    --   76.90-125.00  60.00  102
 33  \w     55.00  97.00   0.50    0.50    --   76.90-125.00-120.00   84
 34  \w     22.00  63.00   0.50    0.50    --   62.87-125.00-180.00   82
;
_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      0.0326678000
_diffrn_orient_matrix_UB_12      0.1000385000
_diffrn_orient_matrix_UB_13      -0.0461702000
_diffrn_orient_matrix_UB_21      0.0575698000
_diffrn_orient_matrix_UB_22      -0.0570716000
_diffrn_orient_matrix_UB_23      -0.0498136000
_diffrn_orient_matrix_UB_31      -0.1252371000
_diffrn_orient_matrix_UB_32      -0.0535378000
_diffrn_orient_matrix_UB_33      -0.0936327000
_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  0.0310
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_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            24328
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78674
_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    1.227
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         7420
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0998
_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^)+(0.1470P)^2^+2.1766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2730
_refine_ls_wR_factor_ref         0.2954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5231
_reflns_number_total             7420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05533g4.cif
_cod_data_source_block           20221124-etbr_auto
_cod_depositor_comments
'Adding full bibliography for 1570870--1570891.cif.'
_cod_original_cell_volume        2121.91(16)
_cod_database_code               1570885
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOBr
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.796
_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
 1.54 with sigma of 0.01
 C1-Br1
 1.94 with sigma of 0.01
 C1A-C15A
 1.54 with sigma of 0.01
 Br1A-C1A
 1.94 with sigma of 0.01
 Br1-C15 \\sim Br1A-C15A
 with sigma of 0.04
 Br1-C1 \\sim Br1A-C1A
 with sigma of 0.02
 C15-C1 \\sim C15A-C1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(Br1A) \\sim Ueq, Uanis(Br1) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C1)=Sof(H1A)=Sof(H1B)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1A(H1AA,H1AB)
5.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C6(H6), C4(H4), C18(H18), C40(H40), C23(H23), C43(H43),
 C26(H26), C37(H37), C32(H32), C21(H21), C19(H19), C20(H20), C41(H41), C42(H42),
  C29(H29), C35(H35), C28(H28), C27(H27), C34(H34), C33(H33)
5.c Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C52(H52A,H52B,H52C), C45(H45A,H45B,H45C), C49(H49A,H49B,
 H49C), C46(H46A,H46B,H46C), C50(H50A,H50B,H50C), C47(H47A,H47B,H47C), C51(H51A,
 H51B,H51C), C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
;
_shelx_res_checksum              74971
_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 2.723
_oxdiff_exptl_absorpt_empirical_full_min 0.506