#------------------------------------------------------------------------------
#$Date: 2020-10-06 09:59:02 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558255.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_1558255
loop_
_publ_author_name
'Wang, Danfeng'
'Malmberg, Robert'
'Pernik, Indrek'
'Prasad, Shyamal K. K.'
'Roemer, Max'
'Venkatesan, Koushik'
'Schmidt, Timothy W.'
'Keaveney, Sinead T.'
'Messerle, Barbara A.'
_publ_section_title
;
 Development of tethered dual catalysts: synergy between photo- and
 transition metal catalysts for enhanced catalysis.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6256
_journal_page_last               6267
_journal_paper_doi               10.1039/d0sc02703k
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C26 H25 B F2 N6'
_chemical_formula_sum            'C26 H25 B F2 N6'
_chemical_formula_weight         470.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-23 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.783(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.308(6)
_cell_length_b                   7.8235(16)
_cell_length_c                   24.123(5)
_cell_measurement_reflns_used    5981
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.73
_cell_volume                     4577.6(18)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.06
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1807
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            58055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.736
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1592 before and 0.1001 after correction. The Ratio of minimum to maximum transmission is 0.7792. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'orangish red'
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       plate
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0577
_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/[σ²(Fo²)+(0.0564P)²+5.8945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2753
_reflns_number_total             4032
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02703k2.cif
_cod_data_source_block           indrek_dryxtal_reprocess1_a
_cod_depositor_comments
;Adding full bibliography for 1558253--1558256.cif.

 Adding full bibliography for 1558253--1558256.cif.
;
_cod_original_cell_volume        4577.6(17)
_cod_database_code               1558255
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
B1 B 0.49064(13) 0.3295(5) 0.63467(15) 0.0256(8) Uani 1 1 d . . . . .
C1 C 0.41617(12) 0.0966(4) 0.61667(14) 0.0264(7) Uani 1 1 d . . . . .
F1 F 0.53234(7) 0.2380(2) 0.62579(9) 0.0439(5) Uani 1 1 d . . . . .
N1 N 0.43470(9) 0.2423(3) 0.60034(10) 0.0230(6) Uani 1 1 d . . . . .
C2 C 0.36462(12) 0.0560(4) 0.57160(14) 0.0281(7) Uani 1 1 d . . . . .
H2 H 0.342539 -0.039578 0.572165 0.034 Uiso 1 1 calc R . . . .
F2 F 0.50156(8) 0.3396(3) 0.69454(8) 0.0463(6) Uani 1 1 d . . . . .
N2 N 0.48669(9) 0.5099(3) 0.60741(10) 0.0223(6) Uani 1 1 d . . . . .
C3 C 0.35125(12) 0.1760(4) 0.52669(13) 0.0258(7) Uani 1 1 d . . . . .
N3 N 0.18917(10) 0.6356(3) 0.20479(11) 0.0263(6) Uani 1 1 d . . . . .
C4 C 0.39562(11) 0.2973(4) 0.54511(13) 0.0207(6) Uani 1 1 d . . . . .
N4 N 0.20210(9) 0.6074(3) 0.26434(11) 0.0210(5) Uani 1 1 d . . . . .
C5 C 0.40240(11) 0.4543(4) 0.52134(12) 0.0212(6) Uani 1 1 d . . . . .
N5 N 0.15610(9) 0.7855(3) 0.33829(11) 0.0240(6) Uani 1 1 d . . . . .
C6 C 0.44717(11) 0.5607(4) 0.55148(13) 0.0223(7) Uani 1 1 d . . . . .
N6 N 0.19499(9) 0.8515(3) 0.32017(10) 0.0199(5) Uani 1 1 d . . . . .
C7 C 0.46042(11) 0.7316(4) 0.54009(13) 0.0255(7) Uani 1 1 d . . . . .
C8 C 0.50627(12) 0.7773(4) 0.58939(14) 0.0312(7) Uani 1 1 d . . . . .
H8 H 0.524783 0.884084 0.594822 0.037 Uiso 1 1 calc R . . . .
C9 C 0.52135(12) 0.6416(4) 0.63033(14) 0.0281(7) Uani 1 1 d . . . . .
C10 C 0.44647(13) 0.0094(4) 0.67468(14) 0.0340(8) Uani 1 1 d . . . . .
H10A H 0.484242 -0.014773 0.678526 0.051 Uiso 1 1 calc GR . . . .
H10B H 0.427833 -0.098002 0.676046 0.051 Uiso 1 1 calc GR . . . .
H10C H 0.447386 0.083381 0.707843 0.051 Uiso 1 1 calc GR . . . .
C11 C 0.30048(12) 0.1741(4) 0.46993(14) 0.0327(8) Uani 1 1 d . . . . .
H11A H 0.280689 0.282516 0.465936 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.276568 0.079535 0.471287 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.310947 0.159159 0.435414 0.049 Uiso 1 1 calc GR . . . .
C12 C 0.43178(13) 0.8430(4) 0.48670(14) 0.0332(8) Uani 1 1 d . . . . .
H12A H 0.432033 0.787168 0.450448 0.050 Uiso 1 1 calc GR . . . .
H12B H 0.450925 0.953076 0.492265 0.050 Uiso 1 1 calc GR . . . .
H12C H 0.393601 0.861935 0.482381 0.050 Uiso 1 1 calc GR . . . .
C13 C 0.56698(13) 0.6365(4) 0.69103(15) 0.0380(8) Uani 1 1 d . . . . .
H13A H 0.551556 0.620659 0.721704 0.057 Uiso 1 1 calc GR . . . .
H13B H 0.587573 0.744198 0.698388 0.057 Uiso 1 1 calc GR . . . .
H13C H 0.591800 0.541314 0.692858 0.057 Uiso 1 1 calc GR . . . .
C14 C 0.35801(11) 0.5193(3) 0.46594(13) 0.0210(6) Uani 1 1 d . . . . .
C15 C 0.35602(12) 0.4814(4) 0.40909(13) 0.0275(7) Uani 1 1 d . . . . .
H15 H 0.383200 0.408846 0.404773 0.033 Uiso 1 1 calc R . . . .
C16 C 0.31489(12) 0.5482(4) 0.35861(14) 0.0271(7) Uani 1 1 d . . . . .
H16 H 0.313860 0.520529 0.319838 0.033 Uiso 1 1 calc R . . . .
C17 C 0.27475(11) 0.6562(3) 0.36409(13) 0.0205(6) Uani 1 1 d . . . . .
C18 C 0.27640(11) 0.6929(4) 0.42055(13) 0.0231(7) Uani 1 1 d . . . . .
H18 H 0.249214 0.765629 0.424806 0.028 Uiso 1 1 calc R . . . .
C19 C 0.31741(11) 0.6248(4) 0.47128(13) 0.0236(7) Uani 1 1 d . . . . .
H19 H 0.317846 0.650219 0.509970 0.028 Uiso 1 1 calc R . . . .
C20 C 0.23262(11) 0.7355(3) 0.30767(12) 0.0205(6) Uani 1 1 d . . . . .
H20 H 0.253451 0.804878 0.288656 0.025 Uiso 1 1 calc R . . . .
C21 C 0.17589(12) 0.4693(4) 0.27431(14) 0.0273(7) Uani 1 1 d . . . . .
H21 H 0.178461 0.427489 0.312276 0.033 Uiso 1 1 calc R . . . .
C22 C 0.14513(12) 0.4018(4) 0.21955(15) 0.0310(8) Uani 1 1 d . . . . .
H22 H 0.122180 0.303500 0.211199 0.037 Uiso 1 1 calc R . . . .
C23 C 0.15471(12) 0.5087(4) 0.17842(14) 0.0312(8) Uani 1 1 d . . . . .
H23 H 0.138378 0.492609 0.136112 0.037 Uiso 1 1 calc R . . . .
C24 C 0.19616(12) 1.0235(4) 0.32189(13) 0.0255(7) Uani 1 1 d . . . . .
H24 H 0.220142 1.096076 0.311612 0.031 Uiso 1 1 calc R . . . .
C25 C 0.15600(13) 1.0733(4) 0.34136(15) 0.0311(8) Uani 1 1 d . . . . .
H25 H 0.146274 1.186669 0.347400 0.037 Uiso 1 1 calc R . . . .
C26 C 0.13254(11) 0.9223(4) 0.35037(13) 0.0246(7) Uani 1 1 d . . . . .
H26 H 0.102984 0.917623 0.363681 0.030 Uiso 1 1 calc R . . . .
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 0.0000 0.0000 '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'
F F 0.0171 0.0103 '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'
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
F1 B1 N1 109.6(3) . . ?
F1 B1 N2 109.3(2) . . ?
N1 B1 N2 106.4(2) . . ?
F2 B1 F1 109.7(3) . . ?
F2 B1 N1 111.2(2) . . ?
F2 B1 N2 110.5(3) . . ?
N1 C1 C2 108.2(3) . . ?
N1 C1 C10 122.6(3) . . ?
C2 C1 C10 129.1(3) . . ?
C1 N1 B1 126.3(2) . . ?
C1 N1 C4 108.7(2) . . ?
C4 N1 B1 125.0(2) . . ?
C3 C2 C1 109.3(3) . . ?
C6 N2 B1 124.8(2) . . ?
C9 N2 B1 127.0(2) . . ?
C9 N2 C6 108.1(2) . . ?
C2 C3 C4 106.2(3) . . ?
C2 C3 C11 125.5(3) . . ?
C4 C3 C11 128.3(3) . . ?
C23 N3 N4 103.3(2) . . ?
N1 C4 C3 107.5(2) . . ?
C5 C4 N1 119.9(2) . . ?
C5 C4 C3 132.3(3) . . ?
N3 N4 C20 119.5(2) . . ?
C21 N4 N3 112.4(2) . . ?
C21 N4 C20 127.1(2) . . ?
C4 C5 C14 119.4(2) . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 C14 118.4(2) . . ?
C26 N5 N6 103.8(2) . . ?
N2 C6 C7 107.6(2) . . ?
C5 C6 N2 119.6(3) . . ?
C5 C6 C7 132.5(3) . . ?
N5 N6 C20 119.1(2) . . ?
C24 N6 N5 112.4(2) . . ?
C24 N6 C20 128.3(2) . . ?
C6 C7 C12 129.0(3) . . ?
C8 C7 C6 105.9(3) . . ?
C8 C7 C12 125.1(3) . . ?
C7 C8 C9 109.1(3) . . ?
N2 C9 C8 109.2(3) . . ?
N2 C9 C13 122.9(3) . . ?
C8 C9 C13 127.8(3) . . ?
C15 C14 C5 122.2(2) . . ?
C15 C14 C19 118.8(3) . . ?
C19 C14 C5 118.9(2) . . ?
C16 C15 C14 120.6(3) . . ?
C15 C16 C17 120.5(3) . . ?
C16 C17 C20 118.6(2) . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 C20 122.3(2) . . ?
C17 C18 C19 120.6(3) . . ?
C18 C19 C14 120.5(3) . . ?
N4 C20 N6 110.5(2) . . ?
N4 C20 C17 111.9(2) . . ?
N6 C20 C17 112.8(2) . . ?
N4 C21 C22 106.9(3) . . ?
C21 C22 C23 104.8(3) . . ?
N3 C23 C22 112.7(3) . . ?
N6 C24 C25 106.5(3) . . ?
C24 C25 C26 105.1(3) . . ?
N5 C26 C25 112.3(2) . . ?
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
B1 F1 1.394(4) . ?
B1 N1 1.540(4) . ?
B1 F2 1.361(4) . ?
B1 N2 1.544(4) . ?
C1 N1 1.357(4) . ?
C1 C2 1.407(4) . ?
C1 C10 1.481(4) . ?
N1 C4 1.399(4) . ?
C2 C3 1.372(4) . ?
N2 C6 1.404(4) . ?
N2 C9 1.344(4) . ?
C3 C4 1.435(4) . ?
C3 C11 1.498(4) . ?
N3 N4 1.360(3) . ?
N3 C23 1.329(4) . ?
C4 C5 1.396(4) . ?
N4 C20 1.446(4) . ?
N4 C21 1.352(4) . ?
C5 C6 1.395(4) . ?
C5 C14 1.483(4) . ?
N5 N6 1.360(3) . ?
N5 C26 1.324(4) . ?
C6 C7 1.435(4) . ?
N6 C20 1.458(3) . ?
N6 C24 1.346(4) . ?
C7 C8 1.373(4) . ?
C7 C12 1.495(4) . ?
C8 C9 1.399(4) . ?
C9 C13 1.492(4) . ?
C14 C15 1.384(4) . ?
C14 C19 1.395(4) . ?
C15 C16 1.381(4) . ?
C16 C17 1.398(4) . ?
C17 C18 1.376(4) . ?
C17 C20 1.516(4) . ?
C18 C19 1.387(4) . ?
C21 C22 1.361(4) . ?
C22 C23 1.393(5) . ?
C24 C25 1.368(4) . ?
C25 C26 1.388(4) . ?
