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#$Date: 2024-11-08 17:48:22 +0200 (Fri, 08 Nov 2024) $
#$Revision: 295835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/79/4517963.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_4517963
loop_
_publ_author_name
'Mansour, Waseem'
'Suleiman, Rami'
'Fettouhi, Mohammed'
'El Ali, Bassam'
_publ_section_title
;
 Soft Heteroleptic N-Heterocyclic Carbene Palladium(II) Species for
 Efficient Catalytic Routes to Alkynones via Carbonylative Sonogashira
 Coupling
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c02413
_journal_year                    2020
_chemical_formula_moiety         'C17 H20 N2'
_chemical_formula_sum            'C17 H20 N2'
_chemical_formula_weight         252.35
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                95.726(6)
_cell_angle_beta                 103.104(5)
_cell_angle_gamma                101.050(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0473(11)
_cell_length_b                   9.0925(16)
_cell_length_c                   10.9446(19)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.717
_cell_measurement_theta_min      2.309
_cell_volume                     662.8(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 Quest diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            50526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.858
_diffrn_reflns_theta_min         2.308
_diffrn_source                   'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS. Ver. 2014/5. (Krause et al., 2015)'
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0576
_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)+(0.0782P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2407
_reflns_number_total             3470
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c02413_si_001.cif
_cod_data_source_block           W1000_0m
_cod_original_cell_volume        662.81(19)
_cod_database_code               4517963
_shelx_shelxl_version_number     2016/6
_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_min   0.983
_shelx_estimated_absorpt_t_max   0.989
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
N1 N 0.6852(2) 0.68408(17) 0.62185(15) 0.0449(4) Uani 1 1 d . . . . .
N2 N 0.39589(18) 0.72071(14) 0.50440(12) 0.0296(3) Uani 1 1 d . . . . .
C1 C 0.5758(2) 0.68300(19) 0.50829(17) 0.0380(4) Uani 1 1 d . . . . .
H1 H 0.616931 0.658442 0.435380 0.046 Uiso 1 1 calc R U . . .
C2 C 0.3893(2) 0.74871(17) 0.63032(14) 0.0303(3) Uani 1 1 d . . . . .
C3 C 0.2496(3) 0.7921(2) 0.68978(16) 0.0398(4) Uani 1 1 d . . . . .
H3 H 0.129580 0.808350 0.643181 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2963(3) 0.8102(2) 0.82049(18) 0.0520(5) Uani 1 1 d . . . . .
H4 H 0.205729 0.839656 0.862556 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4754(3) 0.7855(2) 0.89139(18) 0.0570(6) Uani 1 1 d . . . . .
H5 H 0.501561 0.798429 0.979433 0.068 Uiso 1 1 calc R U . . .
C6 C 0.6127(3) 0.7426(2) 0.83366(18) 0.0503(5) Uani 1 1 d . . . . .
H6 H 0.731676 0.725812 0.881309 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5706(2) 0.72453(18) 0.70125(17) 0.0371(4) Uani 1 1 d . . . . .
C8 C 0.2462(2) 0.73408(16) 0.38888(13) 0.0258(3) Uani 1 1 d . . . . .
C9 C 0.3134(2) 0.68554(18) 0.27022(15) 0.0342(4) Uani 1 1 d . . . . .
H9A H 0.441663 0.749527 0.272679 0.041 Uiso 1 1 calc R U . . .
H9B H 0.328760 0.581659 0.268393 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1590(3) 0.69859(19) 0.15086(15) 0.0395(4) Uani 1 1 d . . . . .
H10 H 0.202793 0.666505 0.075611 0.047 Uiso 1 1 calc R U . . .
C11 C -0.0429(3) 0.5966(2) 0.14699(16) 0.0427(4) Uani 1 1 d . . . . .
H11A H -0.141077 0.603717 0.071048 0.051 Uiso 1 1 calc R U . . .
H11B H -0.030662 0.492007 0.144859 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1398(3) 0.8631(2) 0.15298(16) 0.0429(4) Uani 1 1 d . . . . .
H12A H 0.267302 0.927337 0.154239 0.052 Uiso 1 1 calc R U . . .
H12B H 0.042751 0.872541 0.077289 0.052 Uiso 1 1 calc R U . . .
C13 C -0.1102(2) 0.64646(19) 0.26410(15) 0.0361(4) Uani 1 1 d . . . . .
H13 H -0.240197 0.582154 0.261373 0.043 Uiso 1 1 calc R U . . .
C14 C -0.1283(2) 0.8120(2) 0.26775(17) 0.0394(4) Uani 1 1 d . . . . .
H14A H -0.227981 0.821878 0.193540 0.047 Uiso 1 1 calc R U . . .
H14B H -0.170819 0.843778 0.342583 0.047 Uiso 1 1 calc R U . . .
C15 C 0.0732(2) 0.91292(18) 0.27044(16) 0.0356(4) Uani 1 1 d . . . . .
H15 H 0.060415 1.018482 0.271937 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2270(2) 0.89925(17) 0.39012(15) 0.0305(3) Uani 1 1 d . . . . .
H16A H 0.185297 0.932617 0.464845 0.037 Uiso 1 1 calc R U . . .
H16B H 0.355479 0.963484 0.393345 0.037 Uiso 1 1 calc R U . . .
C17 C 0.0436(2) 0.63080(17) 0.38274(14) 0.0302(3) Uani 1 1 d . . . . .
H17A H 0.056647 0.526326 0.380212 0.036 Uiso 1 1 calc R U . . .
H17B H -0.000440 0.658751 0.457843 0.036 Uiso 1 1 calc R U . . .
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'
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
C1 N1 C7 104.03(14) . . ?
C1 N2 C2 105.31(13) . . ?
C1 N2 C8 126.31(13) . . ?
C2 N2 C8 128.33(12) . . ?
N1 C1 N2 114.99(16) . . ?
N2 C2 C3 133.80(14) . . ?
N2 C2 C7 105.15(14) . . ?
C3 C2 C7 121.05(15) . . ?
C4 C3 C2 117.38(17) . . ?
C3 C4 C5 121.8(2) . . ?
C6 C5 C4 121.06(18) . . ?
C5 C6 C7 118.48(18) . . ?
N1 C7 C6 129.28(17) . . ?
N1 C7 C2 110.52(15) . . ?
C6 C7 C2 120.19(18) . . ?
N2 C8 C9 109.89(12) . . ?
N2 C8 C16 109.76(11) . . ?
C9 C8 C16 108.32(12) . . ?
N2 C8 C17 109.97(12) . . ?
C9 C8 C17 108.53(12) . . ?
C16 C8 C17 110.36(12) . . ?
C10 C9 C8 110.06(13) . . ?
C12 C10 C9 109.26(13) . . ?
C12 C10 C11 109.92(15) . . ?
C9 C10 C11 109.45(14) . . ?
C13 C11 C10 109.29(13) . . ?
C15 C12 C10 109.27(13) . . ?
C11 C13 C17 109.11(14) . . ?
C11 C13 C14 109.77(14) . . ?
C17 C13 C14 109.54(13) . . ?
C15 C14 C13 109.81(13) . . ?
C12 C15 C14 109.68(14) . . ?
C12 C15 C16 109.91(14) . . ?
C14 C15 C16 108.91(13) . . ?
C15 C16 C8 109.66(12) . . ?
C13 C17 C8 109.61(12) . . ?
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
N1 C1 1.304(2) . ?
N1 C7 1.383(2) . ?
N2 C1 1.368(2) . ?
N2 C2 1.3891(19) . ?
N2 C8 1.4837(18) . ?
C2 C3 1.392(2) . ?
C2 C7 1.405(2) . ?
C3 C4 1.379(2) . ?
C4 C5 1.395(3) . ?
C5 C6 1.364(3) . ?
C6 C7 1.398(3) . ?
C8 C9 1.533(2) . ?
C8 C16 1.532(2) . ?
C8 C17 1.534(2) . ?
C9 C10 1.530(2) . ?
C10 C12 1.526(3) . ?
C10 C11 1.531(2) . ?
C11 C13 1.522(2) . ?
C12 C15 1.522(2) . ?
C13 C17 1.530(2) . ?
C13 C14 1.532(2) . ?
C14 C15 1.528(2) . ?
C15 C16 1.532(2) . ?
