Symmetry of Three-Center, Four-Electron Bonds
Reiersolmoen, Ann Chrisitn; Battaglia, Stefano; Øien-Ødegaard, Sigurd; Gupta, Arvind Kumar Kumar; Fiksdahl, Anne; Lindh, Roland; Erdelyi, Mate; Chemical Science  (2020) –; doi:10.1039/D0SC02076A

data_1558455
_publ_section_title
;
 Symmetry of Three-Center, Four-Electron Bonds
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02076A
_journal_year                    2020
_chemical_formula_moiety         '2(C20 H12 I1 N2), 1.5(C H2 Cl2), 2(B F4)'
_chemical_formula_sum            'C41.5 H27 B2 Cl3 F8 I2 N4'
_chemical_formula_weight         1115.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-04 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                86.9030(10)
_cell_angle_beta                 87.8040(10)
_cell_angle_gamma                77.8980(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0108(4)
_cell_length_b                   14.2732(8)
_cell_length_c                   21.1647(12)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.272
_cell_measurement_theta_min      2.474
_cell_volume                     2067.0(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      99.97
_diffrn_detector                 'Bruker Photon100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'long tubular collimator'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37838
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         2.473
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1349 before and 0.0496 after correction. 
The Ratio of minimum to maximum transmission is 0.8155. 
The \l/2 correction factor is Not present.'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_description       prism
_exptl_crystal_F_000             1086
_exptl_crystal_size_max          0.632
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.101
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.8155
_refine_diff_density_max         1.029
_refine_diff_density_min         -1.316
_refine_diff_density_rms         0.098
_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_parameters     620
_refine_ls_number_reflns         10247
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+5.4447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8677
_reflns_number_total             10247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02076a2.cif
_cod_data_source_block           acr-i-clamp
_cod_original_formula_sum        'C41.50 H27 B2 Cl3 F8 I2 N4'
_cod_database_code               1558455
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.840
_shelx_estimated_absorpt_t_min   0.398
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C35-C8 \\sim C16-C2 \\sim C46-C21 \\sim C36-C12 \\sim N4-C44 \\sim N3-C45
 with sigma of 0.02
 C44-C45 \\sim C35-C2 \\sim C46-C36
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C46) = Uanis(I5) = Uanis(C36) = Uanis(I2) = Uanis(C44) = Uanis(C45)
Uanis(C35) = Uanis(I6) = Uanis(C2)
Uanis(C39) = Uanis(I4) = Uanis(C38)
4. Others
 1*[Sof(I3)+Sof(C37)+Sof(C42)]+1*[Sof(I1)+Sof(C40)+Sof(C41)]+1*[Sof(I4)+
 Sof(C38)+Sof(C39)]=1 with esd of 0.0001
 1*[Sof(I2)+Sof(C44)+Sof(C45)]+1*[Sof(I5)+Sof(C36)+Sof(C46)]+1*[Sof(C2)+
 Sof(C35)+Sof(I6)]=1 with esd of 0.0001
 Sof(C44)=Sof(C45)=1-FVAR(1)
 Sof(I2)=FVAR(1)
 Sof(C37)=Sof(C42)=1-FVAR(2)
 Sof(I3)=FVAR(2)
 Sof(C40)=Sof(C41)=1-FVAR(3)
 Sof(I1)=FVAR(3)
 Sof(C38)=Sof(C39)=1-FVAR(4)
 Sof(I4)=FVAR(4)
 Sof(C36)=Sof(C46)=1-FVAR(5)
 Sof(I5)=FVAR(5)
 Sof(C2)=Sof(C35)=1-FVAR(6)
 Sof(I6)=FVAR(6)
 Sof(F8)=Sof(F12)=1-FVAR(7)
 Sof(F11)=Sof(F10)=FVAR(7)
 Fixed Sof: F3(0.5) F6(0.5) F5(0.5) F4(0.5) Cl2(0.5) Cl1(0.5) C0AA(0.5)
 H0AA(0.5) H0AB(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C0AA(H0AA,H0AB)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34)
;
_shelx_res_checksum              68176
_olex2_submission_special_instructions 'No special instructions were received'