Controlling optoelectronic properties and aggregation of planar dipoles through symmetry-preserving modifications
García-Calvo, José; Modino-Montes, María; Romero-Muñiz, Ignacio; Torres, Tomás; Chemical Science  (2025) –; doi:10.1039/D5SC06682D

data_1576317
_publ_section_title
;
 Controlling optoelectronic properties and aggregation of planar dipoles
 through symmetry-preserving modifications
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC06682D
_journal_year                    2025
_chemical_formula_moiety         'C64.5 H51.75 F12 N O6'
_chemical_formula_sum            'C64.5 H51.75 F12 N O6'
_chemical_formula_weight         1164.82
_chemical_name_systematic        'JG162 150K / 4b 150K'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-07-09
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-08-30 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.319(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5665(16)
_cell_length_b                   21.8949(10)
_cell_length_c                   17.2854(15)
_cell_measurement_reflns_used    7758
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      67.6640
_cell_measurement_theta_min      2.6730
_cell_volume                     6273.9(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.144a (release 23-01-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -24.00  28.00   0.50    0.84    --   50.52 -10.00 -61.00  104
  2  \w    -16.00 126.00   0.50    0.84    --   50.52  10.00 111.00  284
  3  \w   -127.00  15.00   0.50    0.84    --  -51.77 -10.00 -61.00  284
  4  \w   -162.00 -21.00   0.50   11.15    --  -87.38 -10.00 -61.00  282
  5  \w     36.00 177.00   0.50   11.15    --  102.49  10.00 111.00  282
  6  \w     19.00 103.00   0.50    0.84    --   50.52-125.00-180.00  168
  7  \w    -45.00 -13.00   0.50   11.15    --  -87.38  45.00  90.00   64
  8  \w    -43.00 -12.00   0.50   11.15    --  -87.38  45.00-120.00   62
  9  \w    -68.00 -24.00   0.50   11.15    --  -87.38  61.00-150.00   88
 10  \w    -46.00 -12.00   0.50   11.15    --  -87.38  45.00 120.00   68
 11  \w    -66.00 -25.00   0.50   11.15    --  -87.38  77.00 -60.00   82
 12  \w   -101.00 -69.00   0.50   11.15    --  -87.38  77.00 -60.00   64
 13  \w     77.00 105.00   0.50   11.15    --  102.49 -95.00-150.00   56
 14  \w     36.00  62.00   0.50   11.15    --  102.49 -95.00-150.00   52
 15  \w     28.00  53.00   0.50   11.15    --  102.49 -45.00-120.00   50
 16  \w     34.00  59.00   0.50   11.15    --  102.49-125.00  30.00   50
 17  \w     26.00  51.00   0.50   11.15    --  102.49 -45.00-180.00   50
 18  \w     69.00 111.00   0.50   11.15    --  102.49-125.00-120.00   84
 19  \w     71.00  99.00   0.50   11.15    --  102.49-125.00-150.00   56
 20  \w     29.00  74.00   0.50   11.15    --  102.49 -61.00 -60.00   90
 21  \w     29.00  57.00   0.50   11.15    --  102.49 -61.00-120.00   56
 22  \w     35.00  62.00   0.50   11.15    --  102.49 -61.00-150.00   54
 23  \w     40.00  88.00   0.50   11.15    --  102.49 -95.00 -60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53205
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         2.665
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   intense
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       plate
_exptl_crystal_F_000             2407
_exptl_crystal_recrystallization_method 'obtained from methanol'
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     874
_refine_ls_number_reflns         11042
_refine_ls_number_restraints     966
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1691
_refine_ls_R_factor_gt           0.1196
_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^)+(0.2300P)^2^+1.9900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3437
_refine_ls_wR_factor_ref         0.3921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5797
_reflns_number_total             11042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06682d2.cif
_cod_data_source_block           04423c
_cod_original_formula_sum        'C64.50 H51.75 F12 N O6'
_cod_database_code               1576317
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.885
_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
 C23-C24A = C24A-C25A = C25A-C26A = C26A-C27A = C27A-C28A
 1.5 with sigma of 0.02
 C23-C24B = C24B-C25B = C25B-C26B = C26B-C27B = C27B-C28B
 1.5 with sigma of 0.02
 C23-C29A = C29A-C30A = C30A-C31A = C31A-C32A = C32A-C33A
 1.5 with sigma of 0.02
 C23-C29B = C29B-C30B = C30B-C31B = C31B-C32B = C32B-C33B
 1.5 with sigma of 0.02
 C56-F1A = C56-F1B = C56-F2A = C56-F2B = C56-F3A = C56-F3B
 1.33 with sigma of 0.02
 C57-F4A = C57-F4B = C57-F5A = C57-F5B = C57-F6A = C57-F6B
 1.33 with sigma of 0.02
 C64-F7A = C64-F7B = C64-F8A = C64-F8B = C64-F9A = C64-F9B
 1.33 with sigma of 0.02
 C65-F10A = C65-F10B = C65-F11A = C65-F11B = C65-F12A = C65-F12B
 1.33 with sigma of 0.02
 C23-C25A = C24A-C26A = C25A-C27A = C26A-C28A
 2.5 with sigma of 0.04
 C23-C25B = C24B-C26B = C25B-C27B = C26B-C28B
 2.5 with sigma of 0.04
 C23-C30A = C29A-C31A = C30A-C32A = C31A-C33A
 2.5 with sigma of 0.04
 C23-C30B = C29B-C31B = C30B-C32B = C31B-C33B
 2.5 with sigma of 0.04
 F1A-F2A = F2A-F3A = F3A-F1A = F1B-F2B = F2B-F3B = F3B-F1B
 2.05 with sigma of 0.04
 F4A-F5A = F5A-F6A = F6A-F4A = F4B-F5B = F5B-F6B = F6B-F4B
 2.05 with sigma of 0.04
 F7A-F8A = F8A-F9A = F9A-F7A = F7B-F8B = F8B-F9B = F9B-F7B
 2.05 with sigma of 0.04
 F10A-F11A = F11A-F12A = F12A-F10A = F10B-F11B = F11B-F12B = F12B-F10B
 2.05 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(F1A) = Uanis(F2A) = Uanis(F3A) = Uanis(F1B) = Uanis(F2B) = Uanis(F3B)
Uanis(F4A) = Uanis(F5A) = Uanis(F6A) = Uanis(F4B) = Uanis(F5B) = Uanis(F6B)
Uanis(F9B) = Uanis(F7B) = Uanis(F8B) = Uanis(F9A) = Uanis(F7A) = Uanis(F8A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
 Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(2)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(2)
 Sof(F7B)=Sof(F8B)=Sof(F9B)=1-FVAR(3)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(3)
 Sof(F10B)=Sof(F11B)=Sof(F12B)=1-FVAR(4)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=FVAR(4)
 Sof(H23B)=Sof(C24B)=Sof(H24C)=Sof(H24D)=Sof(C25B)=Sof(H25C)=Sof(H25D)=
 Sof(C26B)=Sof(H26C)=Sof(H26D)=Sof(C27B)=Sof(H27C)=Sof(H27D)=Sof(C28B)=
 Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C29B)=Sof(H29C)=Sof(H29D)=Sof(C30B)=
 Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31C)=Sof(H31D)=1-FVAR(5)
 Sof(C32B)=Sof(H32C)=Sof(H32D)=Sof(C33B)=Sof(H33D)=Sof(H33E)=Sof(H33F)=0.75*(1-
 FVAR(6))
 Sof(C32A)=Sof(H32A)=Sof(H32B)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(H33C)=0.75*
 FVAR(6)
 Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(C25A)=Sof(H25A)=Sof(H25B)=
 Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(C27A)=Sof(H27A)=Sof(H27B)=Sof(C28A)=
 Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(C30A)=
 Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31A)=Sof(H31B)=FVAR(5)
6.a Ternary CH refined with riding coordinates:
 C23(H23A), C23(H23B)
6.b Secondary CH2 refined with riding coordinates:
 C24A(H24A,H24B), C24B(H24C,H24D), C25A(H25A,H25B), C25B(H25C,H25D), C26A(H26A,
 H26B), C26B(H26C,H26D), C27A(H27A,H27B), C27B(H27C,H27D), C29A(H29A,H29B),
 C29B(H29C,H29D), C30A(H30A,H30B), C30B(H30C,H30D), C31A(H31A,H31B), C31B(H31C,
 H31D), C32A(H32A,H32B), C32B(H32C,H32D)
6.c Me refined with riding coordinates:
 C28A(H28A,H28B,H28C), C28B(H28D,H28E,H28F), C33A(H33A,H33B,H33C), C33B(H33D,
 H33E,H33F)
6.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C14(H14), C16(H16), C18(H18), C20(H20), C35(H35), C37(H37),
 C39(H39), C43(H43), C45(H45), C47(H47), C51(H51), C53(H53), C55(H55), C59(H59),
  C61(H61), C63(H63)
6.e Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C48(H48A,H48B,H48C), C49(H49A,H49B,
 H49C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 294 electrons were 
found in a volume of 1014 A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
7.5[H2O] per Asymmetric Unit 
which account for 300 electrons 
per unit cell.
;
_shelx_res_checksum              25125
_shelx_fab_checksum              54420
_olex2_exptl_crystal_mounting_method 'placed on a MiTeGen micromount'
_olex2_submission_original_sample_id 04423c
_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
- Detector area scaling
;