#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:31:33 +0200 (Fri 05 de May de 2023) $
#$Revision: 283497 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/65/7246564.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246564
loop_
_publ_author_name
'Castellanos-Soriano, Jorge'
'Zähringer, Till J B'
'Herrera-Luna, Jorge C'
'Jiménez, M Consuelo'
'Kerzig, Christoph'
'Pérez-Ruiz, Raúl'
_publ_section_title
;
 A new green-to-blue upconversion system with efficient photoredox
 catalytic properties.
;
_journal_issue                   17
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              12041
_journal_page_last               12049
_journal_paper_doi               10.1039/d3cp00811h
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C19 H18 B F3 N2 S'
_chemical_formula_sum            'C19 H18 B F3 N2 S'
_chemical_formula_weight         374.22
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2022-09-29T09:29:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                80.5679(15)
_cell_angle_beta                 82.5851(15)
_cell_angle_gamma                86.1805(15)
_cell_formula_units_Z            2
_cell_length_a                   7.3747(4)
_cell_length_b                   8.7258(4)
_cell_length_c                   13.7648(7)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.60
_cell_measurement_wavelength     0.71073
_cell_volume                     865.55(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'APPEX3v2022.1-1 (BRUKER AXS, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      250(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_radiation_monochromator  'Incoatec multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29732
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.788
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.9257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS-2016/2'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0471P)²+0.3408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.104
_reflns_Friedel_coverage         0
_reflns_number_gt                3265
_reflns_number_total             3806
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp00811h2.cif
_cod_data_source_block           JCSBDS2
_cod_depositor_comments
'Adding full bibliography for 7246564--7246565.cif.'
_cod_database_code               7246564
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.985
_shelx_shelxl_version_number     2019/1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9066(2) 0.62225(18) 0.23098(11) 0.0364(3) Uani 1 1 d . . . . .
C2 C 0.86103(19) 0.70000(17) 0.31279(11) 0.0344(3) Uani 1 1 d . . . . .
C3 C 0.81040(19) 0.58460(16) 0.39373(11) 0.0315(3) Uani 1 1 d . . . . .
C4 C 0.75874(19) 0.59440(16) 0.49341(11) 0.0321(3) Uani 1 1 d . . . . .
H4 H 0.752295 0.692288 0.514087 0.038 Uiso 1 1 calc R U . . .
C5 C 0.71674(19) 0.46518(16) 0.56277(11) 0.0317(3) Uani 1 1 d . . . . .
C6 C 0.6610(2) 0.45004(18) 0.66665(11) 0.0353(3) Uani 1 1 d . . . . .
C7 C 0.6323(2) 0.29441(19) 0.69845(12) 0.0399(3) Uani 1 1 d . . . . .
H7 H 0.593111 0.248861 0.763891 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6716(2) 0.21517(17) 0.61640(12) 0.0362(3) Uani 1 1 d . . . . .
N1 N 0.72301(16) 0.31789(13) 0.53472(9) 0.0318(3) Uani 1 1 d . . . . .
B1 B 0.7889(2) 0.28200(19) 0.42913(13) 0.0337(3) Uani 1 1 d . . . . .
F1 F 0.65673(14) 0.20439(11) 0.39587(7) 0.0473(2) Uani 1 1 d . . . . .
F2 F 0.95075(14) 0.19039(11) 0.42955(8) 0.0478(3) Uani 1 1 d . . . . .
N2 N 0.82362(16) 0.44007(13) 0.36124(9) 0.0320(3) Uani 1 1 d . . . . .
C9 C 0.8821(2) 0.46284(17) 0.26328(11) 0.0354(3) Uani 1 1 d . . . . .
C10 C 0.8651(2) 0.87038(18) 0.31411(14) 0.0466(4) Uani 1 1 d . . . . .
H10A H 0.864009 0.888492 0.381858 0.07 Uiso 1 1 calc R U . . .
H10B H 0.758555 0.92303 0.286821 0.07 Uiso 1 1 calc R U . . .
H10C H 0.97532 0.91037 0.274509 0.07 Uiso 1 1 calc R U . . .
C11 C 0.6406(2) 0.5796(2) 0.72655(12) 0.0440(4) Uani 1 1 d . . . . .
H11A H 0.675002 0.541242 0.792175 0.066 Uiso 1 1 calc R U . . .
H11B H 0.514283 0.619234 0.732257 0.066 Uiso 1 1 calc R U . . .
H11C H 0.719303 0.662327 0.694136 0.066 Uiso 1 1 calc R U . . .
C12 C 0.6632(3) 0.04570(19) 0.61426(14) 0.0472(4) Uani 1 1 d . . . . .
H12A H 0.619607 -0.006823 0.679994 0.071 Uiso 1 1 calc R U . . .
H12B H 0.784395 0.003463 0.593478 0.071 Uiso 1 1 calc R U . . .
H12C H 0.580195 0.030107 0.567906 0.071 Uiso 1 1 calc R U . . .
C13 C 0.9136(3) 0.3342(2) 0.20345(13) 0.0483(4) Uani 1 1 d . . . . .
H13A H 0.971219 0.373713 0.137501 0.073 Uiso 1 1 calc R U . . .
H13B H 0.797391 0.291776 0.198632 0.073 Uiso 1 1 calc R U . . .
H13C H 0.992737 0.253176 0.235196 0.073 Uiso 1 1 calc R U . . .
S1 S 1.00484(6) 0.70458(5) 0.11278(3) 0.04729(14) Uani 1 1 d . . . . .
C14 C 0.8168(2) 0.75416(18) 0.04304(11) 0.0387(3) Uani 1 1 d . . . . .
C15 C 0.8402(3) 0.8724(2) -0.03756(12) 0.0474(4) Uani 1 1 d . . . . .
H15 H 0.951196 0.923161 -0.052182 0.057 Uiso 1 1 calc R U . . .
C16 C 0.7020(3) 0.9160(2) -0.09639(14) 0.0561(5) Uani 1 1 d . . . . .
H16 H 0.71751 0.996101 -0.151028 0.067 Uiso 1 1 calc R U . . .
C17 C 0.5417(3) 0.8403(2) -0.07367(14) 0.0563(5) Uani 1 1 d . . . . .
C18 C 0.5144(3) 0.7217(3) 0.00442(15) 0.0591(5) Uani 1 1 d . . . . .
H18 H 0.403517 0.67077 0.017917 0.071 Uiso 1 1 calc R U . . .
C19 C 0.6541(2) 0.6786(2) 0.06310(14) 0.0518(4) Uani 1 1 d . . . . .
H19 H 0.638171 0.597279 0.116991 0.062 Uiso 1 1 calc R U . . .
F3 F 0.4034(2) 0.88442(19) -0.13051(11) 0.0862(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 108.11(13) . . ?
C2 C1 S1 126.02(12) . . ?
C9 C1 S1 125.40(12) . . ?
C1 C2 C3 105.88(13) . . ?
C1 C2 C10 127.30(15) . . ?
C3 C2 C10 126.82(14) . . ?
C4 C3 N2 120.12(13) . . ?
C4 C3 C2 130.85(13) . . ?
N2 C3 C2 109.00(13) . . ?
C5 C4 C3 122.06(13) . . ?
C5 C4 H4 119 . . ?
C3 C4 H4 119 . . ?
C4 C5 N1 120.64(13) . . ?
C4 C5 C6 130.88(14) . . ?
N1 C5 C6 108.48(13) . . ?
C7 C6 C5 106.03(13) . . ?
C7 C6 C11 128.36(15) . . ?
C5 C6 C11 125.61(14) . . ?
C6 C7 C8 108.49(14) . . ?
C6 C7 H7 125.8 . . ?
C8 C7 H7 125.8 . . ?
N1 C8 C7 109.20(13) . . ?
N1 C8 C12 122.59(14) . . ?
C7 C8 C12 128.20(15) . . ?
C8 N1 C5 107.80(12) . . ?
C8 N1 B1 127.22(12) . . ?
C5 N1 B1 124.89(12) . . ?
F1 B1 F2 109.33(12) . . ?
F1 B1 N1 110.22(13) . . ?
F2 B1 N1 110.03(12) . . ?
F1 B1 N2 110.54(12) . . ?
F2 B1 N2 109.67(13) . . ?
N1 B1 N2 107.03(11) . . ?
C9 N2 C3 107.96(12) . . ?
C9 N2 B1 126.93(12) . . ?
C3 N2 B1 124.99(12) . . ?
N2 C9 C1 109.04(13) . . ?
N2 C9 C13 123.05(14) . . ?
C1 C9 C13 127.91(15) . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 S1 C14 104.79(7) . . ?
C19 C14 C15 119.33(16) . . ?
C19 C14 S1 123.67(13) . . ?
C15 C14 S1 116.96(13) . . ?
C16 C15 C14 120.52(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 118.68(17) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
F3 C17 C16 119.01(19) . . ?
F3 C17 C18 118.5(2) . . ?
C16 C17 C18 122.47(18) . . ?
C17 C18 C19 118.46(19) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C14 C19 C18 120.52(17) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.401(2) . ?
C1 C9 1.405(2) . ?
C1 S1 1.7522(16) . ?
C2 C3 1.403(2) . ?
C2 C10 1.492(2) . ?
C3 C4 1.391(2) . ?
C3 N2 1.3990(17) . ?
C4 C5 1.377(2) . ?
C4 H4 0.94 . ?
C5 N1 1.3975(18) . ?
C5 C6 1.423(2) . ?
C6 C7 1.378(2) . ?
C6 C11 1.494(2) . ?
C7 C8 1.408(2) . ?
C7 H7 0.94 . ?
C8 N1 1.3475(19) . ?
C8 C12 1.489(2) . ?
N1 B1 1.547(2) . ?
B1 F1 1.3866(19) . ?
B1 F2 1.3918(19) . ?
B1 N2 1.551(2) . ?
N2 C9 1.3481(19) . ?
C9 C13 1.487(2) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C10 H10C 0.97 . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C11 H11C 0.97 . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C12 H12C 0.97 . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C13 H13C 0.97 . ?
S1 C14 1.7775(17) . ?
C14 C19 1.382(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.378(3) . ?
C15 H15 0.94 . ?
C16 C17 1.368(3) . ?
C16 H16 0.94 . ?
C17 F3 1.362(2) . ?
C17 C18 1.369(3) . ?
C18 C19 1.385(3) . ?
C18 H18 0.94 . ?
C19 H19 0.94 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12B F2 0.97 2.52 3.449(2) 160.2 2_756 yes
C13 H13A S1 0.97 2.87 3.3476(19) 111 . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 0.29(16) . . . . ?
S1 C1 C2 C3 -172.17(11) . . . . ?
C9 C1 C2 C10 -179.66(15) . . . . ?
S1 C1 C2 C10 7.9(2) . . . . ?
C1 C2 C3 C4 177.53(15) . . . . ?
C10 C2 C3 C4 -2.5(3) . . . . ?
C1 C2 C3 N2 -0.49(16) . . . . ?
C10 C2 C3 N2 179.47(14) . . . . ?
N2 C3 C4 C5 -0.9(2) . . . . ?
C2 C3 C4 C5 -178.75(14) . . . . ?
C3 C4 C5 N1 -0.6(2) . . . . ?
C3 C4 C5 C6 -179.69(14) . . . . ?
C4 C5 C6 C7 178.27(15) . . . . ?
N1 C5 C6 C7 -0.88(16) . . . . ?
C4 C5 C6 C11 -2.1(2) . . . . ?
N1 C5 C6 C11 178.71(13) . . . . ?
C5 C6 C7 C8 0.70(17) . . . . ?
C11 C6 C7 C8 -178.88(15) . . . . ?
C6 C7 C8 N1 -0.27(17) . . . . ?
C6 C7 C8 C12 179.08(15) . . . . ?
C7 C8 N1 C5 -0.29(16) . . . . ?
C12 C8 N1 C5 -179.68(14) . . . . ?
C7 C8 N1 B1 176.38(13) . . . . ?
C12 C8 N1 B1 -3.0(2) . . . . ?
C4 C5 N1 C8 -178.52(13) . . . . ?
C6 C5 N1 C8 0.72(15) . . . . ?
C4 C5 N1 B1 4.7(2) . . . . ?
C6 C5 N1 B1 -176.04(12) . . . . ?
C8 N1 B1 F1 57.46(19) . . . . ?
C5 N1 B1 F1 -126.41(14) . . . . ?
C8 N1 B1 F2 -63.18(19) . . . . ?
C5 N1 B1 F2 112.95(14) . . . . ?
C8 N1 B1 N2 177.72(13) . . . . ?
C5 N1 B1 N2 -6.15(18) . . . . ?
C4 C3 N2 C9 -177.76(13) . . . . ?
C2 C3 N2 C9 0.50(16) . . . . ?
C4 C3 N2 B1 -1.5(2) . . . . ?
C2 C3 N2 B1 176.74(13) . . . . ?
F1 B1 N2 C9 -59.85(19) . . . . ?
F2 B1 N2 C9 60.76(18) . . . . ?
N1 B1 N2 C9 -179.90(13) . . . . ?
F1 B1 N2 C3 124.62(14) . . . . ?
F2 B1 N2 C3 -114.76(15) . . . . ?
N1 B1 N2 C3 4.57(18) . . . . ?
C3 N2 C9 C1 -0.32(16) . . . . ?
B1 N2 C9 C1 -176.46(13) . . . . ?
C3 N2 C9 C13 179.49(14) . . . . ?
B1 N2 C9 C13 3.3(2) . . . . ?
C2 C1 C9 N2 0.01(17) . . . . ?
S1 C1 C9 N2 172.53(11) . . . . ?
C2 C1 C9 C13 -179.78(15) . . . . ?
S1 C1 C9 C13 -7.3(2) . . . . ?
C2 C1 S1 C14 -96.10(14) . . . . ?
C9 C1 S1 C14 92.70(14) . . . . ?
C1 S1 C14 C19 -26.87(17) . . . . ?
C1 S1 C14 C15 155.26(13) . . . . ?
C19 C14 C15 C16 1.0(3) . . . . ?
S1 C14 C15 C16 178.92(14) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 F3 178.96(17) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
F3 C17 C18 C19 -179.01(18) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C15 C14 C19 C18 -1.0(3) . . . . ?
S1 C14 C19 C18 -178.83(15) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
