#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/33/7023345.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_7023345
loop_
_publ_author_name
'Luo, Jingwei'
'Oliver, Allen G.'
'McIndoe, J. Scott'
_publ_section_title
;
 A detailed kinetic analysis of rhodium-catalyzed alkyne hydrogenation.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11312
_journal_page_last               11318
_journal_paper_doi               10.1039/c3dt51212f
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C24 H24 I P'
_chemical_formula_weight         470.30
_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'
_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     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 96.207(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0516(10)
_cell_length_b                   12.5831(10)
_cell_length_c                   13.2499(10)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.25
_cell_volume                     2163.3(3)
_computing_cell_refinement       'Bruker SAINT v8.18C'
_computing_data_collection       'Bruker APEX-II v2012-10.0'
_computing_data_reduction        'Bruker SAINT v8.18C'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXT-2012/2 (Sheldrick, 2012)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_min         2.081
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.559
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_correction_T_min  0.8813
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       rod
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0236
_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)+(0.0268P)²+1.2216P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0559
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4546
_reflns_number_total             5405
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c3dt51212f.txt
_cod_data_source_block           uvic1304
_cod_database_code               7023345
#BEGIN Tags that were not found in dictionaries:
_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   0.800
_shelx_estimated_absorpt_t_max   0.911
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
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
P1 P 0.59437(4) 0.35145(4) 0.77633(4) 0.01489(10) Uani 1 1 d . .
C1 C 0.58625(15) 0.34134(15) 0.91035(15) 0.0193(4) Uani 1 1 d . .
H1A H 0.6124 0.4076 0.9442 0.023 Uiso 1 1 calc R U
H1B H 0.5133 0.3323 0.9229 0.023 Uiso 1 1 calc R U
C2 C 0.65005(16) 0.24609(16) 0.95519(15) 0.0224(4) Uani 1 1 d . .
H2A H 0.6249 0.1803 0.9197 0.027 Uiso 1 1 calc R U
H2B H 0.7231 0.2561 0.9436 0.027 Uiso 1 1 calc R U
C3 C 0.64279(18) 0.23386(18) 1.06805(16) 0.0282(5) Uani 1 1 d . .
H3A H 0.5708 0.2165 1.0789 0.034 Uiso 1 1 calc R U
H3B H 0.6607 0.3024 1.1023 0.034 Uiso 1 1 calc R U
C4 C 0.71426(18) 0.14714(18) 1.11623(17) 0.0311(5) Uani 1 1 d . .
H4A H 0.7865 0.1666 1.1084 0.037 Uiso 1 1 calc R U
H4B H 0.7072 0.1437 1.1898 0.037 Uiso 1 1 calc R U
C5 C 0.69245(18) 0.0405(2) 1.07102(18) 0.0351(5) Uani 1 1 d . .
C6 C 0.67377(19) -0.0383(2) 1.03465(18) 0.0353(5) Uani 1 1 d . .
H6 H 0.6579 -0.1053 1.0037 0.042 Uiso 1 1 calc R U
C7 C 0.72855(14) 0.35328(14) 0.75839(14) 0.0159(4) Uani 1 1 d . .
C8 C 0.78310(15) 0.44387(16) 0.79383(16) 0.0229(4) Uani 1 1 d . .
H8 H 0.7488 0.5003 0.8239 0.027 Uiso 1 1 calc R U
C9 C 0.88741(16) 0.45062(17) 0.78475(17) 0.0277(5) Uani 1 1 d . .
H9 H 0.9247 0.5123 0.8081 0.033 Uiso 1 1 calc R U
C10 C 0.93784(16) 0.36803(18) 0.74190(17) 0.0282(5) Uani 1 1 d . .
H10 H 1.0095 0.3734 0.7357 0.034 Uiso 1 1 calc R U
C11 C 0.88443(16) 0.27791(17) 0.70810(17) 0.0257(4) Uani 1 1 d . .
H11 H 0.9195 0.2212 0.6793 0.031 Uiso 1 1 calc R U
C12 C 0.77930(15) 0.27011(15) 0.71609(15) 0.0202(4) Uani 1 1 d . .
H12 H 0.7424 0.2082 0.6927 0.024 Uiso 1 1 calc R U
C13 C 0.53804(14) 0.47189(14) 0.72400(14) 0.0166(4) Uani 1 1 d . .
C14 C 0.44746(14) 0.51100(15) 0.75743(15) 0.0203(4) Uani 1 1 d . .
H14 H 0.4195 0.4789 0.8133 0.024 Uiso 1 1 calc R U
C15 C 0.39882(15) 0.59753(16) 0.70789(15) 0.0220(4) Uani 1 1 d . .
H15 H 0.3372 0.6247 0.7301 0.026 Uiso 1 1 calc R U
C16 C 0.43910(16) 0.64432(16) 0.62686(16) 0.0234(4) Uani 1 1 d . .
H16 H 0.4050 0.7033 0.5935 0.028 Uiso 1 1 calc R U
C17 C 0.52931(16) 0.60550(16) 0.59386(16) 0.0248(4) Uani 1 1 d . .
H17 H 0.5571 0.6385 0.5383 0.030 Uiso 1 1 calc R U
C18 C 0.57886(15) 0.51915(16) 0.64136(15) 0.0217(4) Uani 1 1 d . .
H18 H 0.6401 0.4920 0.6182 0.026 Uiso 1 1 calc R U
C19 C 0.52645(14) 0.24431(14) 0.70879(14) 0.0173(4) Uani 1 1 d . .
C20 C 0.54421(15) 0.22521(15) 0.60839(15) 0.0213(4) Uani 1 1 d . .
H20 H 0.5981 0.2615 0.5800 0.026 Uiso 1 1 calc R U
C21 C 0.48296(18) 0.15309(16) 0.55023(17) 0.0265(5) Uani 1 1 d . .
H21 H 0.4947 0.1407 0.4817 0.032 Uiso 1 1 calc R U
C22 C 0.40499(15) 0.09917(16) 0.59120(17) 0.0263(4) Uani 1 1 d . .
H22 H 0.3632 0.0501 0.5508 0.032 Uiso 1 1 calc R U
C23 C 0.38776(15) 0.11668(16) 0.69143(18) 0.0266(5) Uani 1 1 d . .
H23 H 0.3346 0.0789 0.7196 0.032 Uiso 1 1 calc R U
C24 C 0.44817(14) 0.18958(16) 0.75110(16) 0.0224(4) Uani 1 1 d . .
H24 H 0.4362 0.2018 0.8196 0.027 Uiso 1 1 calc R U
I1 I 0.78749(2) 0.13419(2) 0.45604(2) 0.02227(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'
P P 0.1023 0.0942 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 P1 C7 107.69(9)
C13 P1 C1 112.16(9)
C7 P1 C1 107.16(9)
C13 P1 C19 106.39(9)
C7 P1 C19 112.32(9)
C1 P1 C19 111.14(9)
C2 C1 P1 110.44(13)
C2 C1 H1A 109.6
P1 C1 H1A 109.6
C2 C1 H1B 109.6
P1 C1 H1B 109.6
H1A C1 H1B 108.1
C3 C2 C1 111.73(17)
C3 C2 H2A 109.3
C1 C2 H2A 109.3
C3 C2 H2B 109.3
C1 C2 H2B 109.3
H2A C2 H2B 107.9
C2 C3 C4 112.57(18)
C2 C3 H3A 109.1
C4 C3 H3A 109.1
C2 C3 H3B 109.1
C4 C3 H3B 109.1
H3A C3 H3B 107.8
C5 C4 C3 113.24(19)
C5 C4 H4A 108.9
C3 C4 H4A 108.9
C5 C4 H4B 108.9
C3 C4 H4B 108.9
H4A C4 H4B 107.7
C6 C5 C4 177.7(3)
C5 C6 H6 180.0
C12 C7 C8 120.15(17)
C12 C7 P1 124.00(14)
C8 C7 P1 115.80(14)
C9 C8 C7 119.44(18)
C9 C8 H8 120.3
C7 C8 H8 120.3
C8 C9 C10 120.39(19)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C9 120.27(19)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 120.07(19)
C10 C11 H11 120.0
C12 C11 H11 120.0
C7 C12 C11 119.67(18)
C7 C12 H12 120.2
C11 C12 H12 120.2
C14 C13 C18 120.33(17)
C14 C13 P1 120.11(14)
C18 C13 P1 119.13(14)
C15 C14 C13 119.06(18)
C15 C14 H14 120.5
C13 C14 H14 120.5
C16 C15 C14 120.66(18)
C16 C15 H15 119.7
C14 C15 H15 119.7
C15 C16 C17 120.21(18)
C15 C16 H16 119.9
C17 C16 H16 119.9
C18 C17 C16 120.31(19)
C18 C17 H17 119.8
C16 C17 H17 119.8
C17 C18 C13 119.42(18)
C17 C18 H18 120.3
C13 C18 H18 120.3
C20 C19 C24 120.07(17)
C20 C19 P1 118.67(14)
C24 C19 P1 120.80(15)
C21 C20 C19 119.81(19)
C21 C20 H20 120.1
C19 C20 H20 120.1
C22 C21 C20 120.5(2)
C22 C21 H21 119.7
C20 C21 H21 119.7
C21 C22 C23 120.01(19)
C21 C22 H22 120.0
C23 C22 H22 120.0
C22 C23 C24 120.36(19)
C22 C23 H23 119.8
C24 C23 H23 119.8
C23 C24 C19 119.23(19)
C23 C24 H24 120.4
C19 C24 H24 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C13 1.7911(19)
P1 C7 1.7927(19)
P1 C1 1.795(2)
P1 C19 1.7979(19)
C1 C2 1.541(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.516(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.530(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.484(4)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.118(3)
C6 H6 0.9500
C7 C12 1.389(3)
C7 C8 1.398(3)
C8 C9 1.382(3)
C8 H8 0.9500
C9 C10 1.384(3)
C9 H9 0.9500
C10 C11 1.380(3)
C10 H10 0.9500
C11 C12 1.391(3)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.396(3)
C13 C18 1.401(3)
C14 C15 1.389(3)
C14 H14 0.9500
C15 C16 1.378(3)
C15 H15 0.9500
C16 C17 1.388(3)
C16 H16 0.9500
C17 C18 1.381(3)
C17 H17 0.9500
C18 H18 0.9500
C19 C20 1.396(3)
C19 C24 1.399(3)
C20 C21 1.387(3)
C20 H20 0.9500
C21 C22 1.382(3)
C21 H21 0.9500
C22 C23 1.388(3)
C22 H22 0.9500
C23 C24 1.398(3)
C23 H23 0.9500
C24 H24 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
C13 P1 C1 C2 -171.15(13)
C7 P1 C1 C2 -53.16(16)
C19 P1 C1 C2 69.90(16)
P1 C1 C2 C3 -178.70(15)
C1 C2 C3 C4 -174.04(18)
C2 C3 C4 C5 -59.7(3)
C13 P1 C7 C12 -129.77(17)
C1 P1 C7 C12 109.37(17)
C19 P1 C7 C12 -13.0(2)
C13 P1 C7 C8 52.73(17)
C1 P1 C7 C8 -68.13(17)
C19 P1 C7 C8 169.55(15)
C12 C7 C8 C9 1.1(3)
P1 C7 C8 C9 178.72(16)
C7 C8 C9 C10 -0.7(3)
C8 C9 C10 C11 -0.2(3)
C9 C10 C11 C12 0.6(3)
C8 C7 C12 C11 -0.7(3)
P1 C7 C12 C11 -178.12(16)
C10 C11 C12 C7 -0.1(3)
C7 P1 C13 C14 -156.87(15)
C1 P1 C13 C14 -39.20(18)
C19 P1 C13 C14 82.51(17)
C7 P1 C13 C18 30.58(18)
C1 P1 C13 C18 148.25(15)
C19 P1 C13 C18 -90.04(17)
C18 C13 C14 C15 -0.3(3)
P1 C13 C14 C15 -172.73(15)
C13 C14 C15 C16 0.0(3)
C14 C15 C16 C17 -0.2(3)
C15 C16 C17 C18 0.6(3)
C16 C17 C18 C13 -0.8(3)
C14 C13 C18 C17 0.7(3)
P1 C13 C18 C17 173.20(16)
C13 P1 C19 C20 72.36(17)
C7 P1 C19 C20 -45.23(18)
C1 P1 C19 C20 -165.27(15)
C13 P1 C19 C24 -99.80(16)
C7 P1 C19 C24 142.61(15)
C1 P1 C19 C24 22.56(18)
C24 C19 C20 C21 1.0(3)
P1 C19 C20 C21 -171.19(15)
C19 C20 C21 C22 -0.6(3)
C20 C21 C22 C23 -0.3(3)
C21 C22 C23 C24 0.7(3)
C22 C23 C24 C19 -0.3(3)
C20 C19 C24 C23 -0.6(3)
P1 C19 C24 C23 171.46(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 122553580
