Understanding Self-Assembly across Scales in BODIPY Derivatives: from Supramolecular Aggregation in Solution to Optical-Waveguiding Crystalline Materials
González Sánchez, Marina; Garcia, Ana M.; Valera, Jorge Santos; Rodríguez, Ana María; Cabanillas, Juan; Prieto, Pilar; Gonzalez Rodriguez, David; Chemical Science  (2025) –; doi:10.1039/D5SC07776A

data_1576347
_publ_section_title
;
 Understanding Self-Assembly across Scales in BODIPY Derivatives: from
 Supramolecular Aggregation in Solution to Optical-Waveguiding Crystalline
 Materials
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC07776A
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C38 H41 B F2 N2'
_chemical_formula_sum            'C38 H41 B F2 N2'
_chemical_formula_weight         574.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-07-29
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_audit_update_record
;
2025-07-29 deposited with the CCDC.	2025-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.637(5)
_cell_length_b                   11.267(3)
_cell_length_c                   28.605(6)
_cell_measurement_reflns_used    1509
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      14.4297
_cell_measurement_theta_min      2.179
_cell_volume                     6651(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  APEXII
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1360
_diffrn_reflns_av_unetI/netI     0.2101
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            31106
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.301
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1330 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.8281.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       prism
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   0.745
_exptl_transmission_factor_min   0.617
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     787
_refine_ls_number_reflns         11641
_refine_ls_number_restraints     732
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.2653
_refine_ls_R_factor_gt           0.0826
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0946P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.2509
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3737
_reflns_number_total             11641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07776a2.cif
_cod_data_source_block           S_1
_cod_database_code               1576347
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1(3)
 0(3)
2. 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
3. Restrained distances
 C35A-C36A
 1.5 with sigma of 0.02
 C36A-C38A
 1.5 with sigma of 0.02
 C36A-C37A
 1.5 with sigma of 0.02
4. Rigid bond restraints
 C36A, C37A, C38A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C36A, C37A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C35A) \\sim Ueq, Uanis(C36A) \\sim Ueq, Uanis(C37A) \\sim Ueq,
Uanis(C38A) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
6. 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
7. Same fragment restrains
{C35, C36, C37, C38} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C35A, C36A, C37A, C38A}
8.a Ternary CH refined with riding coordinates:
 C31(H31), C36(H36), C31A(H31A), C36A(H36A)
8.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C30A(H30C,
 H30D), C33A(H33C,H33D), C34A(H34C,H34D), C35A(H35C,H35D)
8.c Me refined with everything fixed:
 C37A(H37D,H37E,H37F)
8.d Me refined with riding coordinates:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C38A(H38D,H38E,H38F)
8.e Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A),
 C14A(H14A), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A), C29A(H29A)
8.f Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C),
 C32(H32A,H32B,H32C), C5A(H5AA,H5AB,H5AC), C6A(H6AA,H6AB,H6AC), C20A(H20D,H20E,
 H20F), C21A(H21D,H21E,H21F), C32A(H32D,H32E,H32F)
;
_shelx_res_checksum              50788
_olex2_submission_special_instructions 'No special instructions were received'