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_1570880
_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'
_chemical_formula_sum            'C51 H46 O'
_chemical_formula_weight         674.88
_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                83.916(2)
_cell_angle_beta                 81.263(2)
_cell_angle_gamma                81.850(2)
_cell_formula_units_Z            4
_cell_length_a                   11.3923(2)
_cell_length_b                   18.1449(5)
_cell_length_c                   19.2809(5)
_cell_measurement_reflns_used    31418
_cell_measurement_temperature    285.7(8)
_cell_measurement_theta_max      75.9390
_cell_measurement_theta_min      2.3410
_cell_volume                     3885.01(16)
_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      285.7(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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     78.00 117.00   0.50    0.15    --   73.14  15.00 120.00   78
  2  \w     70.00 114.00   0.50    0.15    --   76.87  15.00  90.00   88
  3  \w     58.00  98.00   0.50    0.15    --   62.79  15.00  60.00   80
  4  \w     66.00 108.00   0.50    0.15    --   76.87  15.00   0.00   84
  5  \w     72.00 116.00   0.50    0.15    --   76.87  15.00-120.00   88
  6  \w     66.00  99.00   0.50    0.15    --   76.87  15.00-150.00   66
  7  \w     64.00  96.00   0.50    0.15    --   62.79  15.00-180.00   64
  8  \w     29.00  54.00   0.50    0.15    --   62.79-129.00  65.00   50
  9  \w     31.00  72.00   0.50    0.15    --   73.14-129.00  65.00   82
 10  \w     31.00  88.00   0.50    0.15    --   73.14-125.00 150.00  114
 11  \w     55.00 100.00   0.50    0.15    --   76.87-129.00  65.00   90
 12  \w     25.00  76.00   0.50    0.15    --   62.79-125.00   0.00  102
 13  \w     31.00  94.00   0.50    0.15    --   73.14-125.00-150.00  126
 14  \w     38.00  97.00   0.50    0.15    --   76.87-125.00 -90.00  118
 15  \w     47.00  98.00   0.50    0.15    --   76.87-125.00  90.00  102
 16  \w    -75.00 -47.00   0.50    0.15    --  -81.55 125.00  90.00   56
 17  \w    -91.00 -66.00   0.50    0.15    --  -76.57 129.00 138.00   50
 18  \w    -86.00 -61.00   0.50    0.15    --  -71.67 129.00 138.00   50
 19  \w    -75.00 -50.00   0.50    0.15    --  -81.55 129.00 138.00   50
 20  \w    -65.00 -40.00   0.50    0.15    --  -63.59 129.00 138.00   50
 21  \w    -83.00 -57.00   0.50    0.15    --  -76.57 125.00  30.00   52
 22  \w    -61.00 -26.00   0.50    0.15    --  -63.59 125.00   0.00   70
 23  \w   -102.00 -45.00   0.50    0.15    --  -81.55 125.00  60.00  114
 24  \w   -102.00 -47.00   0.50    0.15    --  -81.55 125.00  30.00  110
 25  \w   -102.00 -52.00   0.50    0.15    --  -81.55 125.00 150.00  100
 26  \w    -88.00 -30.00   0.50    0.15    --  -71.67 125.00 -90.00  116
 27  \w    -74.00 -48.00   0.50    0.15    --  -76.57 125.00-120.00   52
 28  \w   -102.00 -74.00   0.50    0.15    --  -81.55 125.00-120.00   56
 29  \w    -91.00 -29.00   0.50    0.15    --  -71.67 125.00-150.00  124
 30  \w   -102.00 -44.00   0.50    0.15    --  -81.55 125.00-180.00  116
 31  \w   -102.00 -48.00   0.50    0.15    --  -81.55 125.00-150.00  108
 32  \w   -102.00 -76.00   0.50    0.15    --  -81.55 125.00 -90.00   52
 33  \w   -102.00 -44.00   0.50    0.15    --  -81.55 125.00 -60.00  116
 34  \w   -101.00 -75.00   0.50    0.15    --  -81.55 125.00 -30.00   52
 35  \w   -102.00 -77.00   0.50    0.15    --  -81.55 125.00   0.00   50
 36  \w   -102.00 -69.00   0.50    0.15    --  -81.55 125.00 120.00   66
 37  \w   -124.00 -75.00   0.50    0.15    --  -81.55 -15.00 150.00   98
 38  \w   -101.00 -63.00   0.50    0.15    --  -63.59 -15.00  90.00   76
 39  \w   -118.00 -70.00   0.50    0.15    --  -76.57 -15.00  60.00   96
 40  \w    -98.00 -73.00   0.50    0.15    --  -81.55 -15.00   0.00   50
 41  \w    -79.00 -54.00   0.50    0.15    --  -63.59 -15.00 -90.00   50
 42  \w   -124.00 -99.00   0.50    0.15    --  -81.55 -15.00 -60.00   50
 43  \w   -116.00 -77.00   0.50    0.15    --  -81.55 -15.00-120.00   78
 44  \w    -82.00 -54.00   0.50    0.15    --  -63.59 -15.00-150.00   56
 45  \w   -105.00 -55.00   0.50    0.15    --  -63.59 -15.00-180.00  100
;
_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      0.0379589000
_diffrn_orient_matrix_UB_12      -0.0841653000
_diffrn_orient_matrix_UB_13      0.0166515000
_diffrn_orient_matrix_UB_21      0.0334464000
_diffrn_orient_matrix_UB_22      -0.0093579000
_diffrn_orient_matrix_UB_23      -0.0793321000
_diffrn_orient_matrix_UB_31      0.1283364000
_diffrn_orient_matrix_UB_32      0.0155007000
_diffrn_orient_matrix_UB_33      0.0036219000
_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  0.0265
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            58580
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         2.327
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85731
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00120(12)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1047
_refine_ls_number_reflns         13643
_refine_ls_number_restraints     143
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.5459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11486
_reflns_number_total             13643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05533g4.cif
_cod_data_source_block           20221124-4cbr_auto
_cod_depositor_comments
'Adding full bibliography for 1570870--1570891.cif.'
_cod_original_cell_volume        3885.01(17)
_cod_database_code               1570880
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOBr
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.923
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C71-C70
 1.39 with sigma of 0.01
 C98-C96
 1.54 with sigma of 0.01
 C46-C47 \\sim C46-C47A
 with sigma of 0.02
 C46-C102 \\sim C46-C103
 with sigma of 0.02
 C46-C101 \\sim C46-C1A
 with sigma of 0.02
 C92-C94 \\sim C92-C94A
 with sigma of 0.02
 C92-C93 \\sim C92-C93A
 with sigma of 0.02
 C92-C95 \\sim C92-C95A
 with sigma of 0.02
 C43-C45 \\sim C43-C45A
 with sigma of 0.02
 C43-C44 \\sim C43-C44A
 with sigma of 0.02
 C43-C3 \\sim C43-C3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C47) \\sim Ueq, Uanis(C47A) \\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C1A)
\\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C103) \\sim Ueq, Uanis(C45A) \\sim Ueq,
Uanis(C3) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C44A)
\\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C93A) \\sim Ueq, Uanis(C93) \\sim Ueq,
Uanis(C94A) \\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(C95A) \\sim Ueq, Uanis(C94)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C67) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C66)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C47A)=Sof(H47D)=Sof(H47E)=Sof(H47F)=Sof(C103)=Sof(H10G)=Sof(H10H)=
 Sof(H10I)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(1)
 Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(H47C)=Sof(C102)=Sof(H10A)=Sof(H10B)=
 Sof(H10C)=Sof(C101)=Sof(H10D)=Sof(H10E)=Sof(H10F)=FVAR(1)
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C44A)=Sof(H44D)=Sof(H44E)=
 Sof(H44F)=Sof(C45A)=Sof(H45D)=Sof(H45E)=Sof(H45F)=1-FVAR(2)
 Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(2)
 Sof(C95A)=Sof(H95D)=Sof(H95E)=Sof(H95F)=Sof(C93A)=Sof(H93D)=Sof(H93E)=
 Sof(H93F)=Sof(C94A)=Sof(H94D)=Sof(H94E)=Sof(H94F)=1-FVAR(3)
 Sof(C93)=Sof(H93A)=Sof(H93B)=Sof(H93C)=Sof(C94)=Sof(H94A)=Sof(H94B)=Sof(H94C)=
 Sof(C95)=Sof(H95A)=Sof(H95B)=Sof(H95C)=FVAR(3)
5.a Aromatic/amide H refined with riding coordinates:
 C59(H59), C61(H61), C53(H53), C84(H84), C12(H12), C14(H14), C8(H8), C6(H6),
 C79(H79), C39(H39), C91(H91), C42(H42), C55(H55), C35(H35), C22(H22), C30(H30),
  C25(H25), C40(H40), C83(H83), C81(H81), C90(H90), C17(H17), C77(H77),
 C88(H88), C20(H20), C41(H41), C82(H82), C34(H34), C89(H89), C66(H66), C32(H32),
  C19(H19), C33(H33), C18(H18), C28(H28), C26(H26), C76(H76), C71(H71),
 C27(H27), C75(H75), C74(H74), C69(H69), C67(H67), C68(H68)
5.b Idealised Me refined as rotating group:
 C99(H99A,H99B,H99C), C100(H10J,H10K,H10L), C49(H49A,H49B,H49C), C98(H98A,H98B,
 H98C), C48(H48A,H48B,H48C), C97(H97A,H97B,H97C), C93(H93A,H93B,H93C), C94(H94A,
 H94B,H94C), C47(H47A,H47B,H47C), C45(H45A,H45B,H45C), C95(H95A,H95B,H95C),
 C44(H44A,H44B,H44C), C50(H50A,H50B,H50C), C102(H10A,H10B,H10C), C3(H3A,H3B,
 H3C), C101(H10D,H10E,H10F), C47A(H47D,H47E,H47F), C103(H10G,H10H,H10I),
 C1A(H1AA,H1AB,H1AC), C3A(H3AA,H3AB,H3AC), C44A(H44D,H44E,H44F), C45A(H45D,H45E,
 H45F), C95A(H95D,H95E,H95F), C93A(H93D,H93E,H93F), C94A(H94D,H94E,H94F)
;
_shelx_res_checksum              9439
_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 3.817
_oxdiff_exptl_absorpt_empirical_full_min 0.464