#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/27/7022720.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_7022720
loop_
_publ_author_name
'Gardiner, Michael G.'
'Ho, Curtis C.'
'Mackay, Felicity M.'
'McGuinness, David S.'
'Tucker, Matthew'
_publ_section_title
;
 Selective and adaptable access to N,N'-asymmetrically substituted
 imidazol-2-ylidene bis-NHC ligands: Pd(II) complexes featuring wide
 variation in N-alkyl and aryl steric bulk.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7447
_journal_page_last               7457
_journal_paper_doi               10.1039/c3dt32895c
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C15 H21 Cl N2'
_chemical_formula_weight         264.79
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5500(18)
_cell_length_b                   16.6320(13)
_cell_length_c                   10.9560(9)
_cell_measurement_reflns_used    23956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.83
_cell_measurement_theta_min      3.26
_cell_volume                     1541.5(4)
_computing_cell_refinement       XDS
_computing_data_collection       BLU-ICE
_computing_data_reduction        XDS
_computing_molecular_graphics
;
'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)'
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 'ADSC Q210'
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  '3-BM1 Australian Synchrotron'
_diffrn_measurement_method       Rotation
_diffrn_radiation_monochromator  Si<111>
_diffrn_radiation_source         'synchrotron BM'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71090
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24625
_diffrn_reflns_theta_full        28.83
_diffrn_reflns_theta_max         28.83
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.9059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                3685
_reflns_number_total             3788
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt32895c.txt
_cod_data_source_block           d:\as28ch27
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7022720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.41195(4) 0.091500(19) 0.79260(3) 0.02760(12) Uani 1 1 d .
N1 N 0.80427(13) 0.14378(7) 1.18808(10) 0.0232(2) Uani 1 1 d .
N2 N 0.64136(14) 0.13335(7) 1.01916(11) 0.0269(3) Uani 1 1 d .
C1 C 0.70677(16) 0.09375(8) 1.11883(13) 0.0255(3) Uani 1 1 d .
H1 H 0.6875 0.0392 1.1376 0.031 Uiso 1 1 calc R
C2 C 0.79929(17) 0.21825(8) 1.13093(14) 0.0279(3) Uani 1 1 d .
H2 H 0.8560 0.2651 1.1604 0.033 Uiso 1 1 calc R
C3 C 0.69753(18) 0.21087(9) 1.02476(14) 0.0296(3) Uani 1 1 d .
H3 H 0.6700 0.2518 0.9650 0.036 Uiso 1 1 calc R
H1N H 0.566(3) 0.1125(15) 0.953(2) 0.055 Uiso 1 1 d .
C4 C 0.89964(16) 0.12421(8) 1.30491(12) 0.0249(3) Uani 1 1 d .
C5 C 1.04791(17) 0.08904(9) 1.30300(13) 0.0281(3) Uani 1 1 d .
C6 C 1.13856(19) 0.07350(10) 1.41725(15) 0.0337(3) Uani 1 1 d .
H6 H 1.2395 0.0492 1.4201 0.040 Uiso 1 1 calc R
C7 C 1.0836(2) 0.09303(10) 1.52677(15) 0.0375(4) Uani 1 1 d .
H7 H 1.1478 0.0830 1.6036 0.045 Uiso 1 1 calc R
C8 C 0.9364(2) 0.12679(10) 1.52406(14) 0.0358(3) Uani 1 1 d .
H8 H 0.9003 0.1397 1.5997 0.043 Uiso 1 1 calc R
C9 C 0.83861(18) 0.14263(9) 1.41345(13) 0.0293(3) Uani 1 1 d .
C10 C 1.10618(18) 0.06474(10) 1.18371(14) 0.0330(3) Uani 1 1 d .
H10 H 1.0447 0.0961 1.1150 0.040 Uiso 1 1 calc R
C11 C 1.0731(2) -0.02510(11) 1.15831(16) 0.0421(4) Uani 1 1 d .
H11A H 1.1106 -0.0404 1.0812 0.063 Uiso 1 1 calc R
H11B H 0.9592 -0.0351 1.1512 0.063 Uiso 1 1 calc R
H11C H 1.1284 -0.0571 1.2264 0.063 Uiso 1 1 calc R
C12 C 1.2811(2) 0.08226(14) 1.1833(2) 0.0501(5) Uani 1 1 d .
H12A H 1.3114 0.0655 1.1043 0.075 Uiso 1 1 calc R
H12B H 1.3440 0.0525 1.2505 0.075 Uiso 1 1 calc R
H12C H 1.3003 0.1400 1.1950 0.075 Uiso 1 1 calc R
C13 C 0.6732(2) 0.17582(10) 1.41264(15) 0.0363(3) Uani 1 1 d .
H13 H 0.6225 0.1809 1.3248 0.044 Uiso 1 1 calc R
C14 C 0.5737(2) 0.11813(13) 1.4777(2) 0.0470(4) Uani 1 1 d .
H14A H 0.4673 0.1403 1.4761 0.070 Uiso 1 1 calc R
H14B H 0.6231 0.1109 1.5635 0.070 Uiso 1 1 calc R
H14C H 0.5670 0.0661 1.4354 0.070 Uiso 1 1 calc R
C15 C 0.6767(3) 0.25935(13) 1.4717(3) 0.0684(8) Uani 1 1 d .
H15A H 0.5683 0.2791 1.4695 0.103 Uiso 1 1 calc R
H15B H 0.7358 0.2964 1.4259 0.103 Uiso 1 1 calc R
H15C H 0.7281 0.2561 1.5575 0.103 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 108.96(12)
C1 N1 C4 125.91(12)
C2 N1 C4 125.13(12)
C1 N2 C3 109.02(12)
N2 C1 N1 108.20(12)
C3 C2 N1 106.33(12)
C2 C3 N2 107.49(13)
C5 C4 C9 123.66(13)
C5 C4 N1 118.36(12)
C9 C4 N1 117.97(12)
C6 C5 C4 116.74(14)
C6 C5 C10 120.86(14)
C4 C5 C10 122.34(13)
C7 C6 C5 121.16(15)
C8 C7 C6 120.01(15)
C7 C8 C9 121.87(15)
C8 C9 C4 116.51(14)
C8 C9 C13 121.01(14)
C4 C9 C13 122.46(14)
C5 C10 C12 113.31(15)
C5 C10 C11 109.83(13)
C12 C10 C11 109.87(15)
C9 C13 C14 110.53(15)
C9 C13 C15 111.50(16)
C14 C13 C15 110.57(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3341(18)
N1 C2 1.3857(18)
N1 C4 1.4515(17)
N2 C1 1.3275(19)
N2 C3 1.3741(19)
C2 C3 1.353(2)
C4 C5 1.399(2)
C4 C9 1.4000(19)
C5 C6 1.398(2)
C5 C10 1.519(2)
C6 C7 1.389(3)
C7 C8 1.374(3)
C8 C9 1.394(2)
C9 C13 1.517(2)
C10 C12 1.524(2)
C10 C11 1.539(3)
C13 C14 1.525(2)
C13 C15 1.531(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 67173520
