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_1576316
_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         'C49 H37 F12 N O2'
_chemical_formula_sum            'C49 H37 F12 N O2'
_chemical_formula_weight         899.79
_chemical_name_systematic        'JG-10c 200K / 2a 200K'
_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             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                 94.970(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.0976(3)
_cell_length_b                   36.4931(14)
_cell_length_c                   28.4083(8)
_cell_measurement_reflns_used    10383
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      68.0600
_cell_measurement_theta_min      1.9940
_cell_volume                     8363.3(5)
_computing_cell_refinement       'CrysAlisPro 1.171.44.116a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 43.144a (release 23-01-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.116a (Rigaku OD, 2025)'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_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  42.00   0.50   20.00    --   52.46 -33.00 176.00  132
  2  \w     37.00 122.00   0.50   20.00    --   52.46  33.00 -25.00  170
  3  \w   -108.00 -83.00   0.50   20.00    --  -53.71 -33.00 176.00   50
  4  \w    -29.00  15.00   0.50   20.00    --  -53.71  33.00 -25.00   88
  5  \w   -137.00 -72.00   0.50   50.00    --  -86.93 -33.00 176.00  130
  6  \w    103.00 151.00   0.50   50.00    --  102.30  33.00 -25.00   96
  7  \w    -22.00  22.00   0.50   20.00    --  -53.71  19.00-120.00   88
  8  \w   -122.00 -84.00   0.50   20.00    --  -53.71-125.00 -60.00   76
  9  \w    -40.00 -12.00   0.50   50.00    --  -86.93  38.00  60.00   56
 10  \w    -37.00 -10.00   0.50   50.00    --  -86.93  38.00 -60.00   54
 11  \w   -101.00 -26.00   0.50   50.00    --  -86.93  77.00  60.00  150
 12  \w    -40.00 -12.00   0.50   50.00    --  -86.93  38.00 150.00   56
 13  \w    -61.00 -16.00   0.50   50.00    --  -86.93  57.00 120.00   90
 14  \w    -37.00 -11.00   0.50   50.00    --  -86.93  38.00 -90.00   52
 15  \w    -39.00 -11.00   0.50   50.00    --  -86.93  38.00  30.00   56
 16  \w     33.00  67.00   0.50   50.00    --  102.30 -57.00 150.00   68
 17  \w     33.00  65.00   0.50   50.00    --  102.30 -57.00  90.00   64
 18  \w     29.00  55.00   0.50   50.00    --  102.30 -57.00 -30.00   52
 19  \w     29.00  54.00   0.50   50.00    --  102.30 -57.00 -90.00   50
 20  \w     43.00  69.00   0.50   50.00    --  102.30 -99.00  30.00   52
 21  \w     91.00 123.00   0.50   50.00    --  102.30  57.00  90.00   64
 22  \w     79.00 106.00   0.50   50.00    --  102.30 -99.00  30.00   54
 23  \w    127.00 160.00   0.50   50.00    --  102.30  57.00  90.00   66
 24  \w     33.00  69.00   0.50   50.00    --  102.30 -57.00  30.00   72
 25  \w     77.00 103.00   0.50   50.00    --  102.30 -77.00  60.00   52
 26  \w     36.00 108.00   0.50   50.00    --  102.30 -77.00-150.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0449009000
_diffrn_orient_matrix_UB_12      -0.0044631000
_diffrn_orient_matrix_UB_13      0.0534987000
_diffrn_orient_matrix_UB_21      -0.1703741000
_diffrn_orient_matrix_UB_22      -0.0176693000
_diffrn_orient_matrix_UB_23      0.0050920000
_diffrn_orient_matrix_UB_31      0.0736197000
_diffrn_orient_matrix_UB_32      -0.0381000000
_diffrn_orient_matrix_UB_33      -0.0085612000
_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  0.0991
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            63448
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.860
_diffrn_reflns_theta_min         1.975
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.116a (Rigaku Oxford Diffraction, 2025)
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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       needle
_exptl_crystal_F_000             3696
_exptl_crystal_recrystallization_method 'obtained from methanol'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1456
_refine_ls_number_reflns         15281
_refine_ls_number_restraints     1484
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0831
_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^)+(0.1553P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2212
_refine_ls_wR_factor_ref         0.2763
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7098
_reflns_number_total             15281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06682d2.cif
_cod_data_source_block           04471
_cod_database_code               1576316
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C49H37NO2F12 '
_chemical_oxdiff_usercomment     'JG-10c 200K'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.807
_diffrn_oxdiff_digest_hkl
;
43ecff8e359e89990953a8e3295b88071abd6d
;
_diffrn_oxdiff_digest_od_ed
;

;
_diffrn_oxdiff_measurement_exp_name 04471_rep.par
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H28D,H28E,H28F} of C28B, All C(H,H) groups
 At 1.5 times of:
  {H28A,H28B,H28C} of C28A, {H33A,H33B,H33C} of C33A, {H77A,H77B,H77C} of
  C77A, {H82A,H82B,H82C} of C82A, {H33D,H33E,H33F} of C33B, {H77D,H77E,H77F} of
  C77B, {H82D,H82E,H82F} of C82B
2. Restrained distances
 C36-C40 = C38-C41 = C44-C48 = C46-C49
 1.45 with sigma of 0.02
 C85-C89 = C87-C90 = C93-C97 = C95-C98
 1.45 with sigma of 0.02
 C40-F1 = C40-F2 = C40-F3
 1.33 with sigma of 0.02
 C41-F4 = C41-F5 = C41-F6
 1.33 with sigma of 0.02
 C97-F19 = C97-F20 = C97-F21
 1.33 with sigma of 0.02
 C98-F22 = C98-F23 = C98-F24
 1.33 with sigma of 0.02
 C48-F7A = C48-F8A = C48-F9A
 1.33 with sigma of 0.02
 C48-F7B = C48-F8B = C48-F9B
 1.33 with sigma of 0.02
 C49-F10A = C49-F11A = C49-F12A
 1.33 with sigma of 0.02
 C49-F10B = C49-F11B = C49-F12B
 1.33 with sigma of 0.02
 C89-F13A = C89-F14A = C89-F15A
 1.33 with sigma of 0.02
 C89-F13B = C89-F14B = C89-F15B
 1.33 with sigma of 0.02
 C90-F16A = C90-F17A = C90-F18A
 1.33 with sigma of 0.02
 C90-F16B = C90-F17B = C90-F18B
 1.33 with sigma of 0.02
 C23-C24A = C24A-C25A = C25A-C26A = C26A-C27A = C27A-C28A
 1.55 with sigma of 0.02
 C23-C24B = C24B-C25B = C25B-C26B = C26B-C27B = C27B-C28B
 1.55 with sigma of 0.02
 C23-C29A = C29A-C30A = C30A-C31A = C31A-C32A = C32A-C33A
 1.55 with sigma of 0.02
 C23-C29B = C29B-C30B = C30B-C31B = C31B-C32B = C32B-C33B
 1.55 with sigma of 0.02
 C72-C73A = C73A-C74A = C74A-C75A = C75A-C76A = C76A-C77A
 1.55 with sigma of 0.02
 C72-C78A = C78A-C79A = C79A-C80A = C80A-C81A = C81A-C82A
 1.55 with sigma of 0.02
 C72-C73B = C73B-C74B = C74B-C75B = C75B-C76B = C76B-C77B
 1.55 with sigma of 0.02
 C72-C78B = C78B-C79B = C79B-C80B = C80B-C81B = C81B-C82B
 1.55 with sigma of 0.02
 F1-F2 = F1-F3 = F2-F3
 2.03 with sigma of 0.04
 F4-F5 = F4-F6 = F5-F6
 2.03 with sigma of 0.04
 F19-F20 = F19-F21 = F20-F21
 2.03 with sigma of 0.04
 F22-F23 = F22-F24 = F23-F24
 2.03 with sigma of 0.04
 F7A-F8A = F7A-F9A = F8A-F9A
 2.03 with sigma of 0.04
 F7B-F8B = F7B-F9B = F8B-F9B
 2.03 with sigma of 0.04
 F10A-F11A = F10A-F12A = F11A-F12A
 2.03 with sigma of 0.04
 F10B-F11B = F10B-F12B = F11B-F12B
 2.03 with sigma of 0.04
 F13A-F14A = F13A-F15A = F14A-F15A
 2.03 with sigma of 0.04
 F13B-F14B = F13B-F15B = F14B-F15B
 2.03 with sigma of 0.04
 F16A-F17A = F16A-F18A = F17A-F18A
 2.03 with sigma of 0.04
 F16B-F17B = F16B-F18B = F17B-F18B
 2.03 with sigma of 0.04
 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 = C30A-C32A = C29A-C31A = C31A-C33A
 2.5 with sigma of 0.04
 C23-C30B = C30B-C32B = C29B-C31B = C31B-C33B
 2.5 with sigma of 0.04
 C72-C74A = C74A-C76A = C73A-C75A = C75A-C77A
 2.5 with sigma of 0.04
 C72-C79A = C79A-C81A = C78A-C80A = C80A-C82A
 2.5 with sigma of 0.04
 C72-C74B = C74B-C76B = C73B-C75B = C75B-C77B
 2.5 with sigma of 0.04
 C72-C79B = C79B-C81B = C78B-C80B = C80B-C82B
 2.5 with sigma of 0.04
3. 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
4. Others
 Sof(F7B)=Sof(F8B)=Sof(F9B)=1-FVAR(1)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(1)
 Sof(F10B)=Sof(F11B)=Sof(F12B)=1-FVAR(2)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=FVAR(2)
 Sof(F13B)=Sof(F14B)=Sof(F15B)=1-FVAR(3)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=FVAR(3)
 Sof(F16B)=Sof(F17B)=Sof(F18B)=1-FVAR(4)
 Sof(F16A)=Sof(F17A)=Sof(F18A)=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)=Sof(C32B)=Sof(H32C)=
 Sof(H32D)=Sof(C33B)=Sof(H33D)=Sof(H33E)=Sof(H33F)=1-FVAR(5)
 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)=Sof(C32A)=Sof(H32A)=
 Sof(H32B)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(5)
 Sof(C73B)=Sof(H73C)=Sof(H73D)=Sof(C74B)=Sof(H74C)=Sof(H74D)=Sof(C75B)=
 Sof(H75C)=Sof(H75D)=Sof(C76B)=Sof(H76C)=Sof(H76D)=Sof(C77B)=Sof(H77D)=
 Sof(H77E)=Sof(H77F)=Sof(C78B)=Sof(H78C)=Sof(H78D)=Sof(C79B)=Sof(H79C)=
 Sof(H79D)=Sof(C80B)=Sof(H80C)=Sof(H80D)=Sof(C81B)=Sof(H81C)=Sof(H81D)=
 Sof(C82B)=Sof(H82D)=Sof(H82E)=Sof(H82F)=1-FVAR(6)
 Sof(C73A)=Sof(H73A)=Sof(H73B)=Sof(C74A)=Sof(H74A)=Sof(H74B)=Sof(C75A)=
 Sof(H75A)=Sof(H75B)=Sof(C76A)=Sof(H76A)=Sof(H76B)=Sof(C77A)=Sof(H77A)=
 Sof(H77B)=Sof(H77C)=Sof(C78A)=Sof(H78A)=Sof(H78B)=Sof(C79A)=Sof(H79A)=
 Sof(H79B)=Sof(C80A)=Sof(H80A)=Sof(H80B)=Sof(C81A)=Sof(H81A)=Sof(H81B)=
 Sof(C82A)=Sof(H82A)=Sof(H82B)=Sof(H82C)=FVAR(6)
 Sof(H72B)=1-FVAR(7)
 Sof(H72A)=FVAR(7)
5.a Ternary CH refined with riding coordinates:
 C23(H23A), C23(H23B), C72(H72A), C72(H72B)
5.b Secondary CH2 refined with riding coordinates:
 C24A(H24A,H24B), C25A(H25A,H25B), C26A(H26A,H26B), C27A(H27A,H27B), C29A(H29A,
 H29B), C30A(H30A,H30B), C31A(H31A,H31B), C32A(H32A,H32B), C73A(H73A,H73B),
 C74A(H74A,H74B), C75A(H75A,H75B), C76A(H76A,H76B), C78A(H78A,H78B), C79A(H79A,
 H79B), C80A(H80A,H80B), C81A(H81A,H81B), C24B(H24C,H24D), C25B(H25C,H25D),
 C26B(H26C,H26D), C27B(H27C,H27D), C29B(H29C,H29D), C30B(H30C,H30D), C31B(H31C,
 H31D), C32B(H32C,H32D), C73B(H73C,H73D), C74B(H74C,H74D), C75B(H75C,H75D),
 C76B(H76C,H76D), C78B(H78C,H78D), C79B(H79C,H79D), C80B(H80C,H80D), C81B(H81C,
 H81D)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
 C35(H35), C37(H37), C39(H39), C43(H43), C45(H45), C47(H47), C56(H56), C60(H60),
  C63(H63), C64(H64), C65(H65), C67(H67), C68(H68), C69(H69), C84(H84),
 C86(H86), C88(H88), C92(H92), C94(H94), C96(H96)
5.d Idealised Me refined as rotating group:
 C28A(H28A,H28B,H28C), C33A(H33A,H33B,H33C), C77A(H77A,H77B,H77C), C82A(H82A,
 H82B,H82C), C28B(H28D,H28E,H28F), C33B(H33D,H33E,H33F), C77B(H77D,H77E,H77F),
 C82B(H82D,H82E,H82F)
;
_shelx_res_checksum              88143
_olex2_exptl_crystal_mounting_method 'placed on a MiTeGen micromount'
_olex2_submission_original_sample_id 'JG-10 200K'
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.912
_oxdiff_exptl_absorpt_empirical_full_min 0.567