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_1570886
_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         'C2 H4 Cl2, C51 H46 O'
_chemical_formula_sum            'C53 H50 Cl2 O'
_chemical_formula_weight         773.83
_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             2022-05-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-06-20 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                93.893(2)
_cell_angle_beta                 114.337(2)
_cell_angle_gamma                108.437(2)
_cell_formula_units_Z            2
_cell_length_a                   12.8331(3)
_cell_length_b                   13.0210(3)
_cell_length_c                   15.1558(3)
_cell_measurement_reflns_used    15198
_cell_measurement_temperature    303.00(10)
_cell_measurement_theta_max      66.5380
_cell_measurement_theta_min      3.2560
_cell_volume                     2130.70(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      303.00(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 0.990
_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     59.00 107.00   0.50    0.30    --   62.89  15.00-180.00   96
  2  \w     78.00 115.00   0.50    0.30    --   76.75  15.00   0.00   74
  3  \w     62.00 116.00   0.50    0.30    --   72.93  15.00 120.00  108
  4  \w     59.00  96.00   0.50    0.30    --   62.89  15.00-120.00   74
  5  \w    -68.00 -25.00   0.50    0.30    --  -63.72 125.00-180.00   86
  6  \w    -97.00 -50.00   0.50    0.30    --  -76.43 125.00-180.00   94
  7  \w   -102.00 -42.00   0.50    0.30    --  -81.49 125.00 -90.00  120
  8  \w    -54.00 -29.00   0.50    0.30    --  -71.74 125.00 -30.00   50
  9  \w    -67.00 -39.00   0.50    0.30    --  -76.43 125.00  30.00   56
 10  \w   -102.00 -48.00   0.50    0.30    --  -81.49 125.00  30.00  108
 11  \w   -102.00 -41.00   0.50    0.30    --  -81.49 125.00  60.00  122
 12  \w    -72.00 -40.00   0.50    0.30    --  -81.49 125.00 120.00   64
 13  \w   -102.00 -76.00   0.50    0.30    --  -81.49 125.00 150.00   52
 14  \w   -101.00 -75.00   0.50    0.30    --  -81.49 125.00  90.00   52
 15  \w    -69.00 -39.00   0.50    0.30    --  -81.49 125.00 -30.00   60
 16  \w   -102.00 -77.00   0.50    0.30    --  -81.49 125.00 -60.00   50
 17  \w   -102.00 -55.00   0.50    0.30    --  -81.49 125.00-120.00   94
 18  \w   -102.00 -76.00   0.50    0.30    --  -81.49 125.00-180.00   52
 19  \w   -102.00 -76.00   0.50    0.30    --  -81.49 125.00-150.00   52
 20  \w   -102.00 -77.00   0.50    0.30    --  -81.49 125.00   0.00   50
 21  \w   -105.00 -55.00   0.50    0.30    --  -63.72 -15.00  30.00  100
 22  \w   -114.00 -62.00   0.50    0.30    --  -71.74 -15.00  90.00  104
 23  \w   -105.00 -72.00   0.50    0.30    --  -63.72 -15.00 -60.00   66
 24  \w   -125.00 -72.00   0.50    0.30    --  -81.49 -15.00   0.00  106
 25  \w   -110.00 -75.00   0.50    0.30    --  -81.49 -15.00 -90.00   70
 26  \w   -121.00 -83.00   0.50    0.30    --  -81.49 -15.00 150.00   76
 27  \w   -117.00 -79.00   0.50    0.30    --  -76.43 -15.00-120.00   76
 28  \w   -109.00 -74.00   0.50    0.30    --  -71.74 -15.00-150.00   70
 29  \w   -115.00 -75.00   0.50    0.30    --  -71.74 -15.00-180.00   80
 30  \w     47.00  98.00   0.50    0.30    --   76.75-125.00-180.00  102
 31  \w     25.00  75.00   0.50    0.30    --   62.89-125.00 -30.00  100
 32  \w     35.00  98.00   0.50    0.30    --   76.75-125.00  30.00  126
 33  \w     35.00  98.00   0.50    0.30    --   76.75-125.00  90.00  126
 34  \w     41.00  98.00   0.50    0.30    --   76.75-125.00 -60.00  114
 35  \w     45.00  98.00   0.50    0.30    --   76.75-125.00-120.00  106
;
_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      0.0561387000
_diffrn_orient_matrix_UB_12      0.0681269000
_diffrn_orient_matrix_UB_13      -0.0598753000
_diffrn_orient_matrix_UB_21      0.0835825000
_diffrn_orient_matrix_UB_22      -0.0664317000
_diffrn_orient_matrix_UB_23      0.0130143000
_diffrn_orient_matrix_UB_31      -0.1006365000
_diffrn_orient_matrix_UB_32      -0.0858072000
_diffrn_orient_matrix_UB_33      -0.0968645000
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0254
_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       -18
_diffrn_reflns_number            24534
_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         3.288
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (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    1.206
_exptl_crystal_description       prism
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7455
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0587
_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^)+(0.1083P)^2^+0.4227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1835
_refine_ls_wR_factor_ref         0.1943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6215
_reflns_number_total             7455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05533g4.cif
_cod_data_source_block           20220506-lqy303k
_cod_depositor_comments
'Adding full bibliography for 1570870--1570891.cif.'
_cod_original_cell_volume        2130.70(9)
_cod_database_code               1570886
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.852
_shelx_estimated_absorpt_t_min   0.790
_reflns_odcompleteness_completeness 97.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
 C52-C53
 1.54 with sigma of 0.02
 C53-Cl2
 1.78 with sigma of 0.02
 C52-Cl1
 1.78 with sigma of 0.02
 C52A-Cl1A
 1.78 with sigma of 0.02
 C53A-Cl2A
 1.78 with sigma of 0.02
 C52A-C53A
 1.54 with sigma of 0.02
3. Others
 Sof(Cl2A)=Sof(C53A)=Sof(H53C)=Sof(H53D)=Sof(C52A)=Sof(H52C)=Sof(H52D)=
 Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=Sof(H53B)=
 FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C52(H52A,H52B), C53(H53A,H53B), C53A(H53C,H53D), C52A(H52C,H52D)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C5(H5), C10(H10), C20(H20), C39(H39), C34(H34), C15(H15),
 C36(H36), C25(H25), C29(H29), C18(H18), C38(H38), C37(H37), C32(H32), C17(H17),
  C22(H22), C16(H16), C24(H24), C31(H31), C30(H30), C23(H23)
4.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C47(H47A,H47B,H47C), C51(H51A,H51B,
 H51C), C49(H49A,H49B,H49C), C46(H46A,H46B,H46C), C45(H45A,H45B,H45C), C50(H50A,
 H50B,H50C)
;
_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 4.623
_oxdiff_exptl_absorpt_empirical_full_min 0.381