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#$Date: 2025-08-21 01:27:06 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301840 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/84/4348424.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_4348424
loop_
_publ_author_name
'Macdonald, Charles L. B.'
'Binder, Justin F.'
'Swidan, Ala'aeddeen'
'Nguyen, Jennifer H.'
'Kosnik, Stephanie C.'
'Ellis, Bobby D.'
_publ_section_title
;
 Convenient Preparation and Detailed Analysis of a Series of
 NHC-Stabilized Phosphorus(I) Dyes and Their Derivatives.
;
_journal_issue                   14
_journal_name_full               'Inorganic chemistry'
_journal_page_first              7152
_journal_page_last               7166
_journal_paper_doi               10.1021/acs.inorgchem.6b01163
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C18 H20 N4 P, bR'
_chemical_formula_sum            'C18 H20 Br N4 P'
_chemical_formula_weight         403.26
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_Hall           'I 4bw -2c'
_space_group_name_H-M_alt        'I 41 c d'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   20.0956(7)
_cell_length_b                   20.0956(7)
_cell_length_c                   18.3456(7)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.87
_cell_volume                     7408.6(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0687
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            49192
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.156
_diffrn_reflns_theta_min         3.007
_exptl_absorpt_coefficient_mu    2.313
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2014'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             3296
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0172P)²+3.5015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0535
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3614
_reflns_number_total             4097
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b01163_si_006.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        7408.6(6)
_cod_database_code               4348424
_shelx_shelxl_version_number     2014/7
_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   0.594
_shelx_estimated_absorpt_t_max   0.736
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'-y, -x+1/2, z+3/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1'
'-x+1, y+1, z+1/2'
'-y+1/2, -x+1, z+5/4'
'y+1, x+1/2, z+3/4'
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
P P 0.40502(5) 0.04465(4) 0.05986(6) 0.0271(2) Uani 1 1 d . .
C11 C 0.41678(15) 0.13273(16) 0.06996(18) 0.0211(7) Uani 1 1 d . .
N12 N 0.47260(12) 0.16413(13) 0.04610(14) 0.0224(6) Uani 1 1 d . .
N15 N 0.38046(13) 0.17810(13) 0.10706(15) 0.0214(6) Uani 1 1 d . .
C13 C 0.47162(15) 0.22986(16) 0.06800(18) 0.0217(7) Uani 1 1 d . .
C14 C 0.41272(16) 0.23920(16) 0.10624(18) 0.0207(7) Uani 1 1 d . .
C16 C 0.51762(17) 0.28103(16) 0.0586(2) 0.0286(8) Uani 1 1 d . .
H16 H 0.5578 0.2745 0.0323 0.034 Uiso 1 1 calc R U
C17 C 0.50184(18) 0.34154(17) 0.0893(2) 0.0310(8) Uani 1 1 d . .
H17 H 0.5317 0.3779 0.0838 0.037 Uiso 1 1 calc R U
C18 C 0.44297(18) 0.35062(17) 0.1285(2) 0.0302(8) Uani 1 1 d . .
H18 H 0.4343 0.3929 0.1497 0.036 Uiso 1 1 calc R U
C19 C 0.39680(18) 0.30018(17) 0.1376(2) 0.0275(8) Uani 1 1 d . .
H19 H 0.3565 0.3068 0.1637 0.033 Uiso 1 1 calc R U
C21 C 0.31839(15) 0.04379(15) 0.03795(17) 0.0217(7) Uani 1 1 d . .
N22 N 0.27791(12) -0.00721(13) 0.05815(16) 0.0213(6) Uani 1 1 d . .
N25 N 0.28248(13) 0.08561(13) -0.00462(15) 0.0214(6) Uani 1 1 d . .
C23 C 0.21598(13) 0.00108(17) 0.0266(2) 0.0211(6) Uani 1 1 d . .
C24 C 0.21765(16) 0.06071(16) -0.01173(18) 0.0211(7) Uani 1 1 d . .
C26 C 0.15920(16) -0.03842(16) 0.0290(2) 0.0291(7) Uani 1 1 d . .
H26 H 0.1581 -0.0794 0.0549 0.035 Uiso 1 1 calc R U
C27 C 0.10438(18) -0.01475(18) -0.0084(2) 0.0316(8) Uani 1 1 d . .
H27 H 0.0645 -0.0402 -0.0084 0.038 Uiso 1 1 calc R U
C28 C 0.10602(18) 0.04579(19) -0.0463(2) 0.0340(9) Uani 1 1 d . .
H28 H 0.0671 0.0606 -0.0708 0.041 Uiso 1 1 calc R U
C29 C 0.16295(17) 0.08448(18) -0.0490(2) 0.0301(8) Uani 1 1 d . .
H29 H 0.1643 0.1253 -0.0752 0.036 Uiso 1 1 calc R U
C121 C 0.52461(18) 0.13436(18) 0.0011(2) 0.0336(9) Uani 1 1 d . .
H12A H 0.5338 0.0891 0.0183 0.050 Uiso 1 1 calc R U
H12B H 0.5652 0.1612 0.0046 0.050 Uiso 1 1 calc R U
H12C H 0.5097 0.1327 -0.0497 0.050 Uiso 1 1 calc R U
C151 C 0.31926(17) 0.16517(19) 0.1484(2) 0.0289(8) Uani 1 1 d . .
H15A H 0.2806 0.1718 0.1167 0.043 Uiso 1 1 calc R U
H15B H 0.3167 0.1958 0.1899 0.043 Uiso 1 1 calc R U
H15C H 0.3196 0.1192 0.1663 0.043 Uiso 1 1 calc R U
C221 C 0.2967(2) -0.06326(18) 0.1050(2) 0.0338(9) Uani 1 1 d . .
H22A H 0.3158 -0.0989 0.0751 0.051 Uiso 1 1 calc R U
H22B H 0.2573 -0.0799 0.1305 0.051 Uiso 1 1 calc R U
H22C H 0.3298 -0.0484 0.1408 0.051 Uiso 1 1 calc R U
C251 C 0.30777(17) 0.14197(17) -0.0461(2) 0.0267(8) Uani 1 1 d . .
H25A H 0.3041 0.1825 -0.0167 0.040 Uiso 1 1 calc R U
H25B H 0.2817 0.1471 -0.0909 0.040 Uiso 1 1 calc R U
H25C H 0.3545 0.1342 -0.0586 0.040 Uiso 1 1 calc R U
Br Br 0.30931(2) 0.23514(2) 0.52466(2) 0.03296(10) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C21 P C11 99.27(14)
N15 C11 N12 107.1(3)
N15 C11 P 130.2(3)
N12 C11 P 122.2(2)
C11 N12 C13 109.8(3)
C11 N12 C121 125.6(3)
C13 N12 C121 124.5(3)
C11 N15 C14 109.8(3)
C11 N15 C151 126.4(3)
C14 N15 C151 123.6(3)
N12 C13 C14 106.8(3)
N12 C13 C16 131.3(3)
C14 C13 C16 121.9(3)
C13 C14 N15 106.5(3)
C13 C14 C19 121.6(3)
N15 C14 C19 131.8(3)
C17 C16 C13 116.6(3)
C17 C16 H16 121.7
C13 C16 H16 121.7
C16 C17 C18 121.4(3)
C16 C17 H17 119.3
C18 C17 H17 119.3
C19 C18 C17 122.3(3)
C19 C18 H18 118.9
C17 C18 H18 118.9
C18 C19 C14 116.2(3)
C18 C19 H19 121.9
C14 C19 H19 121.9
N25 C21 N22 107.8(3)
N25 C21 P 130.0(2)
N22 C21 P 121.9(2)
C21 N22 C23 109.5(3)
C21 N22 C221 125.7(3)
C23 N22 C221 124.7(3)
C21 N25 C24 109.1(3)
C21 N25 C251 126.7(3)
C24 N25 C251 123.6(3)
N22 C23 C24 107.1(3)
N22 C23 C26 131.1(3)
C24 C23 C26 121.8(3)
C29 C24 C23 122.0(3)
C29 C24 N25 131.5(3)
C23 C24 N25 106.4(3)
C27 C26 C23 116.2(3)
C27 C26 H26 121.9
C23 C26 H26 121.9
C26 C27 C28 121.8(3)
C26 C27 H27 119.1
C28 C27 H27 119.1
C29 C28 C27 121.6(3)
C29 C28 H28 119.2
C27 C28 H28 119.2
C24 C29 C28 116.5(3)
C24 C29 H29 121.8
C28 C29 H29 121.8
N12 C121 H12A 109.5
N12 C121 H12B 109.5
H12A C121 H12B 109.5
N12 C121 H12C 109.5
H12A C121 H12C 109.5
H12B C121 H12C 109.5
N15 C151 H15A 109.5
N15 C151 H15B 109.5
H15A C151 H15B 109.5
N15 C151 H15C 109.5
H15A C151 H15C 109.5
H15B C151 H15C 109.5
N22 C221 H22A 109.5
N22 C221 H22B 109.5
H22A C221 H22B 109.5
N22 C221 H22C 109.5
H22A C221 H22C 109.5
H22B C221 H22C 109.5
N25 C251 H25A 109.5
N25 C251 H25B 109.5
H25A C251 H25B 109.5
N25 C251 H25C 109.5
H25A C251 H25C 109.5
H25B C251 H25C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P C21 1.787(3)
P C11 1.795(3)
C11 N15 1.352(4)
C11 N12 1.359(4)
N12 C13 1.381(4)
N12 C121 1.460(4)
N15 C14 1.389(4)
N15 C151 1.468(4)
C13 C14 1.389(5)
C13 C16 1.394(4)
C14 C19 1.391(5)
C16 C17 1.378(5)
C16 H16 0.9500
C17 C18 1.396(5)
C17 H17 0.9500
C18 C19 1.384(5)
C18 H18 0.9500
C19 H19 0.9500
C21 N25 1.355(4)
C21 N22 1.360(4)
N22 C23 1.382(4)
N22 C221 1.466(4)
N25 C24 1.402(4)
N25 C251 1.456(4)
C23 C24 1.390(5)
C23 C26 1.391(4)
C24 C29 1.380(5)
C26 C27 1.383(5)
C26 H26 0.9500
C27 C28 1.402(5)
C27 H27 0.9500
C28 C29 1.384(5)
C28 H28 0.9500
C29 H29 0.9500
C121 H12A 0.9800
C121 H12B 0.9800
C121 H12C 0.9800
C151 H15A 0.9800
C151 H15B 0.9800
C151 H15C 0.9800
C221 H22A 0.9800
C221 H22B 0.9800
C221 H22C 0.9800
C251 H25A 0.9800
C251 H25B 0.9800
C251 H25C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 Br 0.95 2.79 3.651(3) 151.5 14_544
C19 H19 Br 0.95 2.75 3.659(4) 161.5 11_544
C121 H12B Br 0.98 2.95 3.928(4) 175.4 14_544
C151 H15A Br 0.98 3.10 3.980(4) 150.2 2_554
C151 H15B Br 0.98 2.95 3.867(4) 156.0 11_544
C221 H22A Br 0.98 2.89 3.764(4) 148.6 5_554
C251 H25A Br 0.98 2.92 3.650(4) 132.3 2_554
C251 H25B Br 0.98 2.78 3.728(4) 163.2 12_453
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
C21 P C11 N15 47.4(3)
C21 P C11 N12 -141.1(3)
N15 C11 N12 C13 -0.2(4)
P C11 N12 C13 -173.4(2)
N15 C11 N12 C121 -177.5(3)
P C11 N12 C121 9.3(5)
N12 C11 N15 C14 0.8(4)
P C11 N15 C14 173.2(3)
N12 C11 N15 C151 -173.9(3)
P C11 N15 C151 -1.4(5)
C11 N12 C13 C14 -0.5(4)
C121 N12 C13 C14 176.9(3)
C11 N12 C13 C16 178.3(4)
C121 N12 C13 C16 -4.4(6)
N12 C13 C14 N15 0.9(4)
C16 C13 C14 N15 -178.0(3)
N12 C13 C14 C19 178.4(3)
C16 C13 C14 C19 -0.4(5)
C11 N15 C14 C13 -1.0(4)
C151 N15 C14 C13 173.8(3)
C11 N15 C14 C19 -178.2(3)
C151 N15 C14 C19 -3.4(6)
N12 C13 C16 C17 -178.4(3)
C14 C13 C16 C17 0.2(5)
C13 C16 C17 C18 0.6(5)
C16 C17 C18 C19 -1.2(6)
C17 C18 C19 C14 0.9(5)
C13 C14 C19 C18 -0.1(5)
N15 C14 C19 C18 176.8(3)
C11 P C21 N25 39.3(3)
C11 P C21 N22 -147.8(3)
N25 C21 N22 C23 1.6(4)
P C21 N22 C23 -172.7(2)
N25 C21 N22 C221 -179.4(3)
P C21 N22 C221 6.3(5)
N22 C21 N25 C24 0.0(4)
P C21 N25 C24 173.7(2)
N22 C21 N25 C251 -171.3(3)
P C21 N25 C251 2.4(5)
C21 N22 C23 C24 -2.5(4)
C221 N22 C23 C24 178.4(3)
C21 N22 C23 C26 177.8(4)
C221 N22 C23 C26 -1.3(6)
N22 C23 C24 C29 -179.1(3)
C26 C23 C24 C29 0.7(6)
N22 C23 C24 N25 2.5(4)
C26 C23 C24 N25 -177.8(3)
C21 N25 C24 C29 -179.8(4)
C251 N25 C24 C29 -8.2(6)
C21 N25 C24 C23 -1.5(4)
C251 N25 C24 C23 170.1(3)
N22 C23 C26 C27 179.1(4)
C24 C23 C26 C27 -0.5(6)
C23 C26 C27 C28 -0.2(6)
C26 C27 C28 C29 0.9(6)
C23 C24 C29 C28 0.0(5)
N25 C24 C29 C28 178.1(4)
C27 C28 C29 C24 -0.8(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168344565
