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_1570877
_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 H3 Cl3'
_chemical_formula_sum            'C53 H49 Cl3 O'
_chemical_formula_weight         808.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-13
_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                90
_cell_angle_beta                 110.663(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.7443(6)
_cell_length_b                   10.4995(3)
_cell_length_c                   24.1927(8)
_cell_measurement_reflns_used    13022
_cell_measurement_temperature    302.33(10)
_cell_measurement_theta_max      75.7010
_cell_measurement_theta_min      2.5150
_cell_volume                     4455.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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      302.33(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     54.00 102.00   0.50    0.30    --   62.89  15.00 150.00   96
  2  \w     55.00 104.00   0.50    0.30    --   62.89  15.00  90.00   98
  3  \w     82.00 108.00   0.50    0.30    --   72.93  15.00 -60.00   52
  4  \w     66.00 120.00   0.50    0.30    --   76.75  15.00   0.00  108
  5  \w     62.00 113.00   0.50    0.30    --   72.93  15.00-120.00  102
  6  \w     62.00  87.00   0.50    0.30    --   72.93  15.00-180.00   50
  7  \w   -122.00 -72.00   0.50    0.30    --  -81.49 -15.00  90.00  100
  8  \w   -103.00 -66.00   0.50    0.30    --  -63.72 -15.00 120.00   74
  9  \w   -100.00 -72.00   0.50    0.30    --  -63.72 -15.00-120.00   56
 10  \w    -98.00 -67.00   0.50    0.30    --  -63.72 -15.00-180.00   62
 11  \w   -115.00 -69.00   0.50    0.30    --  -76.43 -15.00-150.00   92
 12  \w   -123.00 -84.00   0.50    0.30    --  -81.49 -15.00-180.00   78
 13  \w   -115.00 -66.00   0.50    0.30    --  -76.43 -15.00 -30.00   98
 14  \w   -125.00 -81.00   0.50    0.30    --  -81.49 -15.00  30.00   88
 15  \w    -95.00 -36.00   0.50    0.30    --  -76.43 125.00 -60.00  118
 16  \w   -101.00 -44.00   0.50    0.30    --  -81.49 125.00   0.00  114
 17  \w     39.00  68.00   0.50    0.30    --   72.93-125.00-180.00   58
 18  \w     67.00  93.00   0.50    0.30    --   76.75-125.00-180.00   52
 19  \w     35.00  81.00   0.50    0.30    --   76.75-125.00 120.00   92
;
_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      -0.0792509000
_diffrn_orient_matrix_UB_12      -0.0295315000
_diffrn_orient_matrix_UB_13      -0.0459095000
_diffrn_orient_matrix_UB_21      0.0377823000
_diffrn_orient_matrix_UB_22      -0.0585924000
_diffrn_orient_matrix_UB_23      -0.0412381000
_diffrn_orient_matrix_UB_31      0.0010325000
_diffrn_orient_matrix_UB_32      -0.1312673000
_diffrn_orient_matrix_UB_33      0.0287424000
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28798
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         2.586
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         7860
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0832
_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^)+(0.1736P)^2^+1.7364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2708
_refine_ls_wR_factor_ref         0.2840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6149
_reflns_number_total             7860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05533g4.cif
_cod_data_source_block           20221209-lqy-2
_cod_depositor_comments
'Adding full bibliography for 1570870--1570891.cif.'
_cod_database_code               1570877
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOCl
_shelx_estimated_absorpt_t_max   0.882
_shelx_estimated_absorpt_t_min   0.279
_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
 C4-C2
 1.54 with sigma of 0.01
 Cl3-C2 = Cl2-C4 = Cl1-C4
 1.78 with sigma of 0.01
 Cl1-C4 \\sim Cl1A-C4A
 with sigma of 0.02
 Cl2-C2 \\sim Cl2A-C2A
 with sigma of 0.04
 Cl3-C4 \\sim Cl3A-C4A
 with sigma of 0.04
 Cl3-C2 \\sim Cl3A-C2A
 with sigma of 0.02
 Cl2-C4 \\sim Cl2A-C4A
 with sigma of 0.02
 C4-C2 \\sim C4A-C2A
 with sigma of 0.02
 Cl1-Cl2 \\sim Cl1A-Cl2A
 with sigma of 0.04
 Cl1-C2 \\sim Cl1A-C2A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(Cl1)
\\sim Ueq, Uanis(Cl3) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(Cl3A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(Cl2A)
\\sim Ueq, Uanis(Cl1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(C4A)=Sof(H4A)=Sof(Cl2A)=Sof(Cl1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(Cl3A)=
 1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C4)=Sof(H4)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C4A(H4A)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2A(H2AA,H2AB)
5.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00J(H00J), C00K(H00K), C00M(H00M), C00O(H00O),
 C00Q(H00Q), C00U(H00U), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C017(H017),
 C01A(H01G), C01B(H01H), C01C(H01I), C01D(H01J)
5.d Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C), C018(H01D,H01E,H01F), C01E(H01K,H01L,H01M), C01F(H01N,
 H01O,H01P), C01G(H01Q,H01R,H01S), C01H(H01T,H01U,H01V), C01I(H01W,H01X,H01Y),
 C01J(H01Z,H,HA)
;
_shelx_res_checksum              69545
_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 2.538
_oxdiff_exptl_absorpt_empirical_full_min 0.353