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#$Date: 2021-10-29 01:28:10 +0300 (Fri, 29 Oct 2021) $
#$Revision: 270106 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/50/1565050.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_1565050
loop_
_publ_author_name
'Beucher, Helene'
'Schoergenhumer, Johannes'
'Merino, Estíbaliz'
'Nevado, Cristina'
_publ_section_title
;
 Chelation-Assisted C-C Bond Activation of Biphenylene by Gold(I) Halides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03814A
_journal_year                    2021
_chemical_formula_moiety         'C18 H12 Au Cl I N'
_chemical_formula_sum            'C18 H12 Au Cl I N'
_chemical_formula_weight         601.60
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-25 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                97.8087(16)
_cell_angle_beta                 104.2790(15)
_cell_angle_gamma                107.5011(15)
_cell_formula_units_Z            2
_cell_length_a                   7.30740(10)
_cell_length_b                   10.1541(2)
_cell_length_c                   11.6688(2)
_cell_measurement_reflns_used    19330
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      33.1990
_cell_measurement_theta_min      2.1780
_cell_volume                     779.30(3)
_computing_cell_refinement
'CrysAlisPro, Version 1.171.40.68a (Rigaku Oxford Diffraction, 2019)'
_computing_data_collection
'CrysAlisPro, Version 1.171.40.68a (Rigaku Oxford Diffraction, 2019)'
_computing_data_reduction
'CrysAlisPro, Version 1.171.40.68a (Rigaku Oxford Diffraction, 2019)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'hybrid pixel area detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type
'Pilatus 200K hybrid pixel area detector on \k goniostat'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction XtaLAB Synergy, dual radiation diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25807
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.036
_diffrn_reflns_theta_min         2.160
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray source'
_exptl_absorpt_coefficient_mu    11.585
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.158
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model 
plus an empirical absorption correction using spherical harmonics, 
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.564
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.929
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.00144(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018 (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         5319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0179
_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/[σ²(Fo²)+(0.0167P)²+0.8729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0404
_refine_ls_wR_factor_ref         0.0409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4978
_reflns_number_total             5319
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc03814a2.cif
_cod_data_source_block           NV2009
_cod_original_cell_volume        779.30(2)
_cod_database_code               1565050
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.807
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_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
Au1 Au 0.22686(2) 0.45287(2) 0.62080(2) 0.01915(3) Uani 1 1 d . . . . .
I1 I 0.07687(3) 0.23892(2) 0.71788(2) 0.03180(5) Uani 1 1 d . . . . .
Cl1 Cl 0.71058(14) 1.02388(8) 0.84184(8) 0.0475(2) Uani 1 1 d . . . . .
N1 N 0.1177(3) 0.3444(2) 0.43495(19) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.0011(4) 0.2079(3) 0.3932(3) 0.0292(5) Uani 1 1 d . . . . .
H1 H -0.036307 0.153399 0.449192 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0661(5) 0.1441(3) 0.2718(3) 0.0358(6) Uani 1 1 d . . . . .
H2 H -0.148362 0.046804 0.243687 0.043 Uiso 1 1 calc R U . . .
C3 C -0.0114(4) 0.2247(3) 0.1917(3) 0.0343(6) Uani 1 1 d . . . . .
H3 H -0.056736 0.181974 0.107379 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1099(4) 0.3684(3) 0.2319(2) 0.0267(5) Uani 1 1 d . . . . .
C5 C 0.1768(4) 0.4273(3) 0.3571(2) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.1551(5) 0.4491(3) 0.1376(3) 0.0349(6) Uani 1 1 d . . . . .
H61 H 0.116265 0.533288 0.147691 0.052 Uiso 1 1 calc R U . . .
H62 H 0.078858 0.388370 0.056521 0.052 Uiso 1 1 calc R U . . .
H63 H 0.299535 0.478199 0.147016 0.052 Uiso 1 1 calc R U . . .
C7 C 0.3085(3) 0.5748(3) 0.4212(2) 0.0211(4) Uani 1 1 d . . . . .
C8 C 0.3448(3) 0.6080(2) 0.5467(2) 0.0195(4) Uani 1 1 d . . . . .
C9 C 0.4640(4) 0.7401(2) 0.6238(2) 0.0214(4) Uani 1 1 d . . . . .
C10 C 0.5546(4) 0.8468(3) 0.5695(2) 0.0256(5) Uani 1 1 d . . . . .
H10 H 0.636541 0.938917 0.617472 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5233(4) 0.8161(3) 0.4449(2) 0.0270(5) Uani 1 1 d . . . . .
H11 H 0.586069 0.888750 0.409190 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4042(4) 0.6839(3) 0.3707(2) 0.0254(5) Uani 1 1 d . . . . .
H12 H 0.387287 0.667051 0.285975 0.030 Uiso 1 1 calc R U . . .
C13 C 0.4743(4) 0.7423(3) 0.7518(2) 0.0226(4) Uani 1 1 d . . . . .
C14 C 0.3673(4) 0.6100(3) 0.7731(2) 0.0223(4) Uani 1 1 d . . . . .
C15 C 0.3648(4) 0.5961(3) 0.8899(2) 0.0287(5) Uani 1 1 d . . . . .
H15 H 0.292840 0.507236 0.902647 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4667(5) 0.7113(3) 0.9874(3) 0.0362(6) Uani 1 1 d . . . . .
H16 H 0.464899 0.701363 1.066986 0.043 Uiso 1 1 calc R U . . .
C17 C 0.5704(5) 0.8399(3) 0.9692(3) 0.0372(6) Uani 1 1 d . . . . .
H17 H 0.640478 0.918762 1.036329 0.045 Uiso 1 1 calc R U . . .
C18 C 0.5736(4) 0.8553(3) 0.8533(3) 0.0302(5) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 5 2 0.0617
-5 0 2 0.0791
0 -1 0 0.0570
0 1 0 0.0742
5 -4 -2 0.0667
0 0 1 0.0124
0 0 -1 0.0124
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
C8 Au1 C14 81.23(10) . . ?
C8 Au1 N1 79.81(9) . . ?
C14 Au1 N1 161.02(9) . . ?
C8 Au1 I1 177.80(6) . . ?
C14 Au1 I1 99.74(7) . . ?
N1 Au1 I1 99.24(6) . . ?
C1 N1 C5 121.1(2) . . ?
C1 N1 Au1 124.64(18) . . ?
C5 N1 Au1 114.29(16) . . ?
N1 C1 C2 121.9(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 117.7(3) . . ?
C5 C4 C6 124.7(3) . . ?
C3 C4 C6 117.6(2) . . ?
N1 C5 C4 119.5(2) . . ?
N1 C5 C7 112.9(2) . . ?
C4 C5 C7 127.6(2) . . ?
C4 C6 H61 109.5 . . ?
C4 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
C4 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
C8 C7 C12 116.3(2) . . ?
C8 C7 C5 116.0(2) . . ?
C12 C7 C5 127.7(2) . . ?
C7 C8 C9 125.2(2) . . ?
C7 C8 Au1 116.97(18) . . ?
C9 C8 Au1 117.80(17) . . ?
C8 C9 C10 116.7(2) . . ?
C8 C9 C13 112.6(2) . . ?
C10 C9 C13 130.7(2) . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 122.7(2) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C7 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C18 C13 C14 116.6(2) . . ?
C18 C13 C9 128.9(2) . . ?
C14 C13 C9 114.5(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 Au1 125.33(19) . . ?
C13 C14 Au1 113.81(17) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 122.0(3) . . ?
C17 C18 Cl1 116.1(2) . . ?
C13 C18 Cl1 121.9(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
Au1 C8 1.973(2) . ?
Au1 C14 2.025(3) . ?
Au1 N1 2.126(2) . ?
Au1 I1 2.65578(19) . ?
Cl1 C18 1.746(3) . ?
N1 C1 1.336(3) . ?
N1 C5 1.379(3) . ?
C1 C2 1.373(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(4) . ?
C4 C6 1.501(4) . ?
C5 C7 1.484(3) . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 C8 1.396(3) . ?
C7 C12 1.407(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.405(3) . ?
C9 C13 1.474(3) . ?
C10 C11 1.391(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.396(4) . ?
C13 C14 1.426(3) . ?
C14 C15 1.394(4) . ?
C15 C16 1.383(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
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
C5 N1 C1 C2 -0.4(4) . . . . ?
Au1 N1 C1 C2 179.4(2) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C2 C3 C4 C6 -177.7(3) . . . . ?
C1 N1 C5 C4 1.5(3) . . . . ?
Au1 N1 C5 C4 -178.39(17) . . . . ?
C1 N1 C5 C7 -179.0(2) . . . . ?
Au1 N1 C5 C7 1.2(2) . . . . ?
C3 C4 C5 N1 -1.7(3) . . . . ?
C6 C4 C5 N1 176.9(2) . . . . ?
C3 C4 C5 C7 178.7(2) . . . . ?
C6 C4 C5 C7 -2.7(4) . . . . ?
N1 C5 C7 C8 -2.5(3) . . . . ?
C4 C5 C7 C8 177.1(2) . . . . ?
N1 C5 C7 C12 176.0(2) . . . . ?
C4 C5 C7 C12 -4.4(4) . . . . ?
C12 C7 C8 C9 1.3(3) . . . . ?
C5 C7 C8 C9 180.0(2) . . . . ?
C12 C7 C8 Au1 -176.00(16) . . . . ?
C5 C7 C8 Au1 2.7(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
Au1 C8 C9 C10 176.82(17) . . . . ?
C7 C8 C9 C13 -179.8(2) . . . . ?
Au1 C8 C9 C13 -2.5(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C13 C9 C10 C11 178.7(2) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C8 C7 C12 C11 -1.2(3) . . . . ?
C5 C7 C12 C11 -179.8(2) . . . . ?
C8 C9 C13 C18 -178.2(2) . . . . ?
C10 C9 C13 C18 2.6(4) . . . . ?
C8 C9 C13 C14 1.8(3) . . . . ?
C10 C9 C13 C14 -177.4(2) . . . . ?
C18 C13 C14 C15 -0.4(4) . . . . ?
C9 C13 C14 C15 179.6(2) . . . . ?
C18 C13 C14 Au1 179.66(19) . . . . ?
C9 C13 C14 Au1 -0.3(3) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
Au1 C14 C15 C16 180.0(2) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C13 -0.5(5) . . . . ?
C16 C17 C18 Cl1 180.0(2) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C9 C13 C18 C17 -179.4(3) . . . . ?
C14 C13 C18 Cl1 -179.90(19) . . . . ?
C9 C13 C18 Cl1 0.1(4) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.0014 5.0061 1.9896 0.2169 -0.1028 0.3998
-5.0002 0.0005 2.0025 -0.1529 0.0924 0.4777
0.0002 -1.0010 0.0025 -0.0688 0.0303 -0.0032
-0.0002 1.0010 -0.0025 0.0688 -0.0303 0.0032
5.0011 -4.0044 -1.9924 -0.1223 0.0287 -0.4906
-0.0004 0.0020 1.0007 -0.0120 -0.0632 0.0039
0.0004 -0.0020 -1.0007 0.0120 0.0632 -0.0039
