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_1570881
_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                83.876(2)
_cell_angle_beta                 81.273(2)
_cell_angle_gamma                81.763(2)
_cell_formula_units_Z            4
_cell_length_a                   11.3790(2)
_cell_length_b                   18.1303(3)
_cell_length_c                   19.2624(4)
_cell_measurement_reflns_used    20313
_cell_measurement_temperature    291(1)
_cell_measurement_theta_max      75.0710
_cell_measurement_theta_min      2.3700
_cell_volume                     3872.71(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      291(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 0.992
_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     56.00  98.00   0.50    0.51    --   62.89  15.00 120.00   84
  2  \w     77.00 121.00   0.50    0.51    --   76.75  15.00 150.00   88
  3  \w     65.00 117.00   0.50    0.51    --   76.75  15.00  90.00  104
  4  \w     65.00 121.00   0.50    0.51    --   76.75  15.00  30.00  112
  5  \w     26.00  51.00   0.50    0.51    --   62.89-125.00-180.00   50
  6  \w     23.00  57.00   0.50    0.51    --   62.89-125.00-150.00   68
  7  \w     42.00  98.00   0.50    0.51    --   76.75-125.00 -30.00  112
  8  \w     41.00  97.00   0.50    0.51    --   76.75-125.00 -90.00  112
  9  \w     45.00  80.00   0.50    0.51    --   76.75-125.00  30.00   70
 10  \w     28.00  57.00   0.50    0.51    --   62.89-125.00 150.00   58
 11  \w     31.00  86.00   0.50    0.51    --   72.93-125.00 120.00  110
 12  \w     35.00  96.00   0.50    0.51    --   76.75-125.00  60.00  122
 13  \w     35.00  98.00   0.50    0.51    --   76.75-125.00-150.00  126
 14  \w   -111.00 -72.00   0.50    0.51    --  -81.49 -15.00-120.00   78
 15  \w    -97.00 -71.00   0.50    0.51    --  -63.72 -15.00-180.00   52
 16  \w    -97.00 -56.00   0.50    0.51    --  -63.72 -15.00-150.00   82
 17  \w   -105.00 -71.00   0.50    0.51    --  -76.43 -15.00-150.00   68
 18  \w   -101.00 -68.00   0.50    0.51    --  -63.72 -15.00 -90.00   66
 19  \w   -120.00 -80.00   0.50    0.51    --  -81.49 -15.00-180.00   80
 20  \w   -116.00 -69.00   0.50    0.51    --  -76.43 -15.00 -90.00   94
 21  \w    -94.00 -69.00   0.50    0.51    --  -63.72 -15.00 -60.00   50
 22  \w   -124.00 -72.00   0.50    0.51    --  -81.49 -15.00 120.00  104
 23  \w   -103.00 -70.00   0.50    0.51    --  -63.72 -15.00 150.00   66
 24  \w    -65.00 -25.00   0.50    0.51    --  -63.72 125.00 -30.00   80
 25  \w    -53.00 -25.00   0.50    0.51    --  -63.72 125.00 -90.00   56
 26  \w   -102.00 -76.00   0.50    0.51    --  -81.49 125.00-180.00   52
 27  \w   -102.00 -76.00   0.50    0.51    --  -81.49 125.00 -60.00   52
 28  \w   -102.00 -46.00   0.50    0.51    --  -81.49 125.00 -90.00  112
 29  \w   -102.00 -75.00   0.50    0.51    --  -81.49 125.00 -30.00   54
 30  \w   -101.00 -52.00   0.50    0.51    --  -81.49 125.00   0.00   98
 31  \w   -102.00 -48.00   0.50    0.51    --  -81.49 125.00  30.00  108
 32  \w   -102.00 -52.00   0.50    0.51    --  -81.49 125.00  60.00  100
 33  \w   -102.00 -60.00   0.50    0.51    --  -81.49 125.00  90.00   84
 34  \w   -100.00 -50.00   0.50    0.51    --  -81.49 125.00 150.00  100
 35  \w    -52.00 -27.00   0.50    0.51    --  -63.72 125.00 150.00   50
 36  \w    -73.00 -34.00   0.50    0.51    --  -76.43 125.00  90.00   78
 37  \w   -102.00 -42.00   0.50    0.51    --  -81.49 125.00-150.00  120
;
_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      -0.0008712000
_diffrn_orient_matrix_UB_12      0.0765668000
_diffrn_orient_matrix_UB_13      0.0280419000
_diffrn_orient_matrix_UB_21      0.0232327000
_diffrn_orient_matrix_UB_22      -0.0393472000
_diffrn_orient_matrix_UB_23      0.0724778000
_diffrn_orient_matrix_UB_31      0.1361611000
_diffrn_orient_matrix_UB_32      -0.0041017000
_diffrn_orient_matrix_UB_33      -0.0236121000
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_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            49955
_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         2.329
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84632
_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    1.157
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1077
_refine_ls_number_reflns         13584
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0851P)^2^+0.5967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10143
_reflns_number_total             13584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05533g4.cif
_cod_data_source_block           20221124-ch3cn_auto
_cod_depositor_comments
'Adding full bibliography for 1570870--1570891.cif.'
_cod_database_code               1570881
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.928
_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
 C95-C97 \\sim C95-C97A
 with sigma of 0.02
 C95-C98 \\sim C95-C98A
 with sigma of 0.02
 C47-C49 \\sim C47-C49A
 with sigma of 0.02
 C95-C96 \\sim C95-C96A
 with sigma of 0.02
 C47-C50 \\sim C47-C50A
 with sigma of 0.02
 C47-C48 \\sim C47-C48A
 with sigma of 0.02
 C99-C101 \\sim C99-C3
 with sigma of 0.02
 C99-C102 \\sim C99-C1B
 with sigma of 0.02
 C99-C100 \\sim C99-C1A
 with sigma of 0.02
 C43-C46 \\sim C43-C46A
 with sigma of 0.02
 C43-C44 \\sim C43-C44A
 with sigma of 0.02
 C43-C45 \\sim C43-C45A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C101)
\\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C96A) \\sim Ueq,
Uanis(C98) \\sim Ueq, Uanis(C98A) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C97A)
\\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(C48A) \\sim Ueq, Uanis(C48) \\sim Ueq,
Uanis(C49A) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50A) \\sim Ueq, Uanis(C50)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C30) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C31)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C43) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C45)
\\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C35) \\sim Ueq,
Uanis(C34) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C46A) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C44A)
\\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C45A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C45) \\sim Ueq, Uanis(C44A) \\sim Ueq, Uanis(C45A) \\sim Ueq, Uanis(C46A)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C46) \\sim Ueq: with sigma of 0.001 and
sigma for terminal atoms of 0.002
Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Others
 Sof(C98A)=Sof(H98D)=Sof(H98E)=Sof(H98F)=Sof(C96A)=Sof(H96D)=Sof(H96E)=
 Sof(H96F)=Sof(C97A)=Sof(H97D)=Sof(H97E)=Sof(H97F)=1-FVAR(1)
 Sof(C97)=Sof(H97A)=Sof(H97B)=Sof(H97C)=Sof(C98)=Sof(H98A)=Sof(H98B)=Sof(H98C)=
 Sof(C96)=Sof(H96A)=Sof(H96B)=Sof(H96C)=FVAR(1)
 Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=Sof(C49A)=Sof(H49D)=Sof(H49E)=
 Sof(H49F)=Sof(C48A)=Sof(H48D)=Sof(H48E)=Sof(H48F)=1-FVAR(2)
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=
 Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=FVAR(2)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=1-FVAR(3)
 Sof(C100)=Sof(H10G)=Sof(H10H)=Sof(H10I)=Sof(C101)=Sof(H10J)=Sof(H10K)=
 Sof(H10L)=Sof(C102)=Sof(H10M)=Sof(H10N)=Sof(H10O)=FVAR(3)
 Sof(C46A)=Sof(H46D)=Sof(H46E)=Sof(H46F)=Sof(C44A)=Sof(H44D)=Sof(H44E)=
 Sof(H44F)=Sof(C45A)=Sof(H45D)=Sof(H45E)=Sof(H45F)=1-FVAR(4)
 Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=
 Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(4)
5.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C57(H57), C55(H55), C91(H91), C17(H17), C6(H6), C8(H8),
 C22(H22), C28(H28), C63(H63), C74(H74), C94(H94), C61(H61), C82(H82), C87(H87),
  C77(H77), C92(H92), C20(H20), C18(H18), C27(H27), C25(H25), C72(H72),
 C35(H35), C93(H93), C86(H86), C39(H39), C19(H19), C69(H69), C84(H84), C26(H26),
  C85(H85), C71(H71), C80(H80), C30(H30), C78(H78), C70(H70), C42(H42),
 C40(H40), C41(H41), C79(H79), C34(H34), C32(H32), C33(H33)
5.b Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C51(H51A,H51B,H51C), C104(H10A,H10B,H10C), C46(H46A,H46B,
 H46C), C103(H10D,H10E,H10F), C100(H10G,H10H,H10I), C101(H10J,H10K,H10L),
 C102(H10M,H10N,H10O), C97(H97A,H97B,H97C), C48(H48A,H48B,H48C), C49(H49A,H49B,
 H49C), C98(H98A,H98B,H98C), C50(H50A,H50B,H50C), C45(H45A,H45B,H45C), C44(H44A,
 H44B,H44C), C96(H96A,H96B,H96C), C98A(H98D,H98E,H98F), C96A(H96D,H96E,H96F),
 C97A(H97D,H97E,H97F), C50A(H50D,H50E,H50F), C49A(H49D,H49E,H49F), C48A(H48D,
 H48E,H48F), C3(H3A,H3B,H3C), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC),
 C46A(H46D,H46E,H46F), C44A(H44D,H44E,H44F), C45A(H45D,H45E,H45F)
;
_shelx_res_checksum              64006
_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 4.287
_oxdiff_exptl_absorpt_empirical_full_min 0.374