#------------------------------------------------------------------------------
#$Date: 2025-11-29 22:01:11 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303812 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/94/7719478.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_7719478
loop_
_publ_author_name
'Karataş, Mert Olgun'
'Hinojosa, Diego R.'
'Passarelli, Vincenzo'
'Oro, Luis A.'
'Pérez-Torrente, Jesús J'
'Castarlenas, Ricardo'
_publ_section_title
;
 Rhodium(I) complexes with proton-responsive anionic tethered
 N-heterocyclic carbene ligands: synthesis and application in alkyne
 dimerization.
;
_journal_issue                   40
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15306
_journal_page_last               15319
_journal_paper_doi               10.1039/d5dt01516b
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C20 H24 N3 O, C H Cl3, Br'
_chemical_formula_sum            'C21 H25 Br Cl3 N3 O'
_chemical_formula_weight         521.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-06-13 deposited with the CCDC.	2025-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.042(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9779(6)
_cell_length_b                   14.1815(7)
_cell_length_c                   14.4172(9)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.632
_cell_measurement_theta_min      2.430
_cell_volume                     2411.5(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2016) in APEX4'
_computing_data_collection       'SAINT V8.40B (Bruker AXS, 2016) in APEX4'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2016) in APEX4'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and π scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            64512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.030
_diffrn_source                   'Mo microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.054
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
 --------------------------------------------------------------------------

 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.953
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5318
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0481
_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/[σ²(Fo²)+(0.0497P)²+5.1084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4627
_reflns_number_total             5318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01516b2.cif
_cod_data_source_block           cmpd_1_VPX281V_MERT
_cod_depositor_comments
'Adding full bibliography for 7719477--7719479.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7719478
_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.
;
loop_
_space_group_symop_operation_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_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
C25A C 0.0260(6) 0.1576(5) 0.5048(6) 0.068(2) Uani 0.667(3) 1 d D . P A 1
H25A H 0.0020 0.1461 0.4358 0.082 Uiso 0.667(3) 1 calc R U P A 1
Cl1A Cl -0.0125(3) 0.0594(2) 0.5657(2) 0.1174(12) Uani 0.667(3) 1 d D . P A 1
Cl2A Cl 0.1741(2) 0.17072(18) 0.52828(18) 0.0680(6) Uiso 0.667(3) 1 d D . P A 1
Cl3A Cl -0.0443(2) 0.25596(18) 0.53493(18) 0.0907(8) Uani 0.667(3) 1 d D . P A 1
C25B C 0.0143(9) 0.2075(9) 0.4856(9) 0.059(4) Uani 0.333(3) 1 d D . P A 2
H25B H -0.0048 0.1668 0.4284 0.071 Uiso 0.333(3) 1 calc R U P A 2
Cl1B Cl 0.0192(3) 0.3242(3) 0.4511(3) 0.0723(12) Uani 0.333(3) 1 d D . P A 2
Cl2B Cl -0.0848(4) 0.1893(5) 0.5578(3) 0.106(2) Uani 0.333(3) 1 d D . P A 2
Cl3B Cl 0.1482(5) 0.1802(4) 0.5431(4) 0.0785(16) Uiso 0.333(3) 1 d D . P A 2
C1 C 0.3969(2) 0.3720(2) 0.2876(2) 0.0296(6) Uani 1 1 d . . . . .
H1 H 0.4193 0.4347 0.2766 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4008(2) 0.2180(2) 0.3123(2) 0.0317(6) Uani 1 1 d . . . . .
H3 H 0.4274 0.1550 0.3216 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2934(2) 0.2482(2) 0.3113(2) 0.0322(6) Uani 1 1 d . . . . .
H4 H 0.2304 0.2104 0.3195 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5837(2) 0.2949(2) 0.2923(2) 0.0277(6) Uani 1 1 d . . . . .
C8 C 0.7371(3) 0.2018(2) 0.2937(2) 0.0331(7) Uani 1 1 d . . . . .
C9 C 0.8037(3) 0.2798(2) 0.2794(3) 0.0368(7) Uani 1 1 d . . . . .
H9 H 0.8813 0.2725 0.2746 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7538(3) 0.3671(3) 0.2726(3) 0.0416(8) Uani 1 1 d . . . . .
H10 H 0.7971 0.4213 0.2635 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6392(3) 0.3764(2) 0.2792(3) 0.0379(7) Uani 1 1 d . . . . .
H11 H 0.6023 0.4360 0.2747 0.046 Uiso 1 1 calc R U . . .
C13 C 0.1958(3) 0.4058(2) 0.2948(3) 0.0349(7) Uani 1 1 d . . . . .
C14 C 0.1865(3) 0.4535(3) 0.3782(3) 0.0504(9) Uani 1 1 d . . . . .
C15 C 0.0893(4) 0.5085(3) 0.3755(3) 0.0576(11) Uani 1 1 d . . . . .
H15 H 0.0792 0.5428 0.4301 0.069 Uiso 1 1 calc R U . . .
C16 C 0.0088(3) 0.5143(3) 0.2967(3) 0.0498(10) Uani 1 1 d . . . . .
H16 H -0.0563 0.5524 0.2972 0.060 Uiso 1 1 calc R U . . .
C17 C 0.0199(3) 0.4660(3) 0.2162(3) 0.0457(9) Uani 1 1 d . . . . .
H17 H -0.0379 0.4709 0.1622 0.055 Uiso 1 1 calc R U . . .
C18 C 0.1152(3) 0.4097(2) 0.2124(3) 0.0384(7) Uani 1 1 d . . . . .
C19 C 0.2770(4) 0.4497(4) 0.4666(3) 0.0699(14) Uani 1 1 d . . . . .
H19 H 0.3296 0.3965 0.4598 0.084 Uiso 1 1 calc R U . . .
C20 C 0.3446(4) 0.5412(6) 0.4744(4) 0.095(2) Uani 1 1 d . . . . .
H20A H 0.3864 0.5455 0.4218 0.143 Uiso 1 1 calc R U . . .
H20B H 0.3983 0.5420 0.5341 0.143 Uiso 1 1 calc R U . . .
H20C H 0.2928 0.5949 0.4722 0.143 Uiso 1 1 calc R U . . .
C21 C 0.2281(6) 0.4339(4) 0.5565(4) 0.0821(16) Uani 1 1 d . . . . .
H21A H 0.2901 0.4233 0.6095 0.123 Uiso 1 1 calc R U . . .
H21B H 0.1782 0.3786 0.5484 0.123 Uiso 1 1 calc R U . . .
H21C H 0.1846 0.4896 0.5691 0.123 Uiso 1 1 calc R U . . .
C22 C 0.1322(3) 0.3637(3) 0.1218(3) 0.0533(10) Uani 1 1 d . . . . .
H22 H 0.1957 0.3175 0.1373 0.064 Uiso 1 1 calc R U . . .
C23 C 0.1686(4) 0.4383(4) 0.0562(4) 0.0749(15) Uani 1 1 d . . . . .
H23A H 0.1077 0.4846 0.0396 0.112 Uiso 1 1 calc R U . . .
H23B H 0.1841 0.4077 -0.0013 0.112 Uiso 1 1 calc R U . . .
H23C H 0.2373 0.4701 0.0881 0.112 Uiso 1 1 calc R U . . .
C24 C 0.0277(4) 0.3097(4) 0.0724(3) 0.0680(13) Uani 1 1 d . . . . .
H24A H 0.0040 0.2642 0.1163 0.102 Uiso 1 1 calc R U . . .
H24B H 0.0464 0.2761 0.0177 0.102 Uiso 1 1 calc R U . . .
H24C H -0.0342 0.3542 0.0516 0.102 Uiso 1 1 calc R U . . .
N2 N 0.46436(19) 0.29614(17) 0.29745(18) 0.0266(5) Uani 1 1 d . . . . .
N5 N 0.2930(2) 0.34438(18) 0.29582(18) 0.0286(5) Uani 1 1 d . . . . .
N7 N 0.6281(2) 0.20907(18) 0.30062(19) 0.0311(6) Uani 1 1 d . . . . .
Br Br 1.03294(2) 0.10630(2) 0.26233(2) 0.03379(11) Uani 1 1 d . . . . .
O12 O 0.77766(19) 0.11356(16) 0.3024(2) 0.0433(6) Uani 1 1 d . . . . .
H12 H 0.8453 0.1133 0.2939 0.065 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
Cl3A C25A Cl1A 109.5(5) . . ?
Cl3A C25A Cl2A 112.8(4) . . ?
Cl1A C25A Cl2A 109.4(4) . . ?
Cl3B C25B Cl2B 111.0(7) . . ?
Cl3B C25B Cl1B 106.2(7) . . ?
Cl2B C25B Cl1B 112.1(7) . . ?
N5 C1 N2 108.1(3) . . ?
C4 C3 N2 107.1(3) . . ?
C3 C4 N5 106.9(3) . . ?
N7 C6 C11 126.5(3) . . ?
N7 C6 N2 113.0(3) . . ?
C11 C6 N2 120.5(3) . . ?
N7 C8 O12 114.2(3) . . ?
N7 C8 C9 122.8(3) . . ?
O12 C8 C9 123.0(3) . . ?
C10 C9 C8 118.1(3) . . ?
C9 C10 C11 120.2(3) . . ?
C6 C11 C10 115.9(3) . . ?
C18 C13 C14 124.4(3) . . ?
C18 C13 N5 117.9(3) . . ?
C14 C13 N5 117.7(3) . . ?
C15 C14 C13 115.9(4) . . ?
C15 C14 C19 120.7(4) . . ?
C13 C14 C19 123.4(3) . . ?
C16 C15 C14 121.6(4) . . ?
C15 C16 C17 121.2(3) . . ?
C16 C17 C18 121.1(4) . . ?
C13 C18 C17 115.9(3) . . ?
C13 C18 C22 122.9(3) . . ?
C17 C18 C22 121.0(3) . . ?
C20 C19 C14 108.9(5) . . ?
C20 C19 C21 109.9(4) . . ?
C14 C19 C21 113.1(4) . . ?
C18 C22 C23 109.5(4) . . ?
C18 C22 C24 113.4(4) . . ?
C23 C22 C24 110.8(4) . . ?
C1 N2 C3 108.8(2) . . ?
C1 N2 C6 126.1(3) . . ?
C3 N2 C6 125.1(2) . . ?
C1 N5 C4 109.2(2) . . ?
C1 N5 C13 125.7(3) . . ?
C4 N5 C13 125.0(2) . . ?
C6 N7 C8 116.6(3) . . ?
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
C25A Cl3A 1.724(8) . ?
C25A Cl1A 1.751(7) . ?
C25A Cl2A 1.756(8) . ?
C25B Cl3B 1.716(11) . ?
C25B Cl2B 1.729(10) . ?
C25B Cl1B 1.732(11) . ?
C1 N5 1.329(4) . ?
C1 N2 1.338(4) . ?
C3 C4 1.352(4) . ?
C3 N2 1.382(4) . ?
C4 N5 1.383(4) . ?
C6 N7 1.325(4) . ?
C6 C11 1.363(4) . ?
C6 N2 1.445(3) . ?
C8 N7 1.331(4) . ?
C8 O12 1.341(4) . ?
C8 C9 1.400(5) . ?
C9 C10 1.370(5) . ?
C10 C11 1.398(4) . ?
C13 C18 1.394(5) . ?
C13 C14 1.402(5) . ?
C13 N5 1.452(4) . ?
C14 C15 1.396(5) . ?
C14 C19 1.523(6) . ?
C15 C16 1.359(6) . ?
C16 C17 1.373(6) . ?
C17 C18 1.402(5) . ?
C18 C22 1.505(6) . ?
C19 C20 1.523(9) . ?
C19 C21 1.528(7) . ?
C22 C23 1.532(7) . ?
C22 C24 1.534(6) . ?
