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#$Date: 2020-12-19 04:23:18 +0100 (Sat 19 de Dec de 2020) $
#$Revision: 259993 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/61/7706109.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_7706109
loop_
_publ_author_name
'Cicač-Hudi, Mario'
'Feil, Christoph M.'
'Birchall, Nicholas'
'Nieger, Martin'
'Gudat, Dietrich'
_publ_section_title
;
 Proton transfer vs. oligophosphine formation by P-C/P-H σ-bond
 metathesis: decoding the competing Brønsted and Lewis type reactivities
 of imidazolio-phosphines.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17401
_journal_page_last               17413
_journal_paper_doi               10.1039/d0dt03633a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C9 H18 N2 P, I'
_chemical_formula_sum            'C9 H18 I N2 P'
_chemical_formula_weight         312.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-23 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.069(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2450(5)
_cell_length_b                   7.4965(4)
_cell_length_c                   10.4442(6)
_cell_measurement_reflns_used    2559
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      33.265
_cell_measurement_theta_min      2.153
_cell_volume                     655.65(6)
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17628
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.265
_diffrn_reflns_theta_min         2.153
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.530
_exptl_absorpt_correction_T_max  0.3096
_exptl_absorpt_correction_T_min  0.1110
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'BLESSING 1995'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.635
_exptl_crystal_size_mid          0.512
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0374(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0194
_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)+(0.0235P)²+0.2339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2559
_reflns_number_total             2681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03633a2.cif
_cod_data_source_block           g477_mn
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7706109
_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   0.296
_shelx_estimated_absorpt_t_max   0.538
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
P1 P 1.03094(5) 0.7500 0.82083(5) 0.02286(9) Uani 1 2 d S T P . .
H1 H 1.031(2) 0.619(3) 0.902(2) 0.034 Uiso 1 1 d . U . . .
C1 C 0.81547(19) 0.7500 0.71390(16) 0.0174(2) Uani 1 2 d S T P . .
N1 N 0.74580(16) 0.7500 0.57149(14) 0.0181(2) Uani 1 2 d S T P . .
N2 N 0.69774(16) 0.7500 0.75722(14) 0.0196(2) Uani 1 2 d S T P . .
C2 C 0.58273(19) 0.7500 0.52487(17) 0.0222(3) Uani 1 2 d S T P . .
H2 H 0.5057 0.7500 0.4292 0.027 Uiso 1 2 calc R U P . .
C3 C 0.5523(2) 0.7500 0.64072(18) 0.0234(3) Uani 1 2 d S T P . .
H3 H 0.4500 0.7500 0.6416 0.028 Uiso 1 2 calc R U P . .
C4 C 0.8286(2) 0.7500 0.47709(16) 0.0202(3) Uani 1 2 d S T P . .
H4 H 0.9463 0.7500 0.5375 0.024 Uiso 1 2 calc R U P . .
C5 C 0.78715(19) 0.5812(2) 0.38849(15) 0.0299(3) Uani 1 1 d . . . . .
H5A H 0.8421 0.5817 0.3263 0.045 Uiso 1 1 calc R U . . .
H5B H 0.8211 0.4769 0.4508 0.045 Uiso 1 1 calc R U . . .
H5C H 0.6715 0.5760 0.3312 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7183(2) 0.7500 0.90543(18) 0.0255(3) Uani 1 2 d S T P . .
H6 H 0.8353 0.7500 0.9682 0.031 Uiso 1 2 calc R U P . .
C7 C 0.6467(2) 0.5809(3) 0.93479(16) 0.0371(3) Uani 1 1 d . . . . .
H7A H 0.6606 0.5814 1.0332 0.056 Uiso 1 1 calc R U . . .
H7B H 0.5327 0.5756 0.8714 0.056 Uiso 1 1 calc R U . . .
H7C H 0.7009 0.4766 0.9187 0.056 Uiso 1 1 calc R U . . .
I1 I 0.86010(2) 0.2500 0.73553(2) 0.02437(5) Uani 1 2 d S T P . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 H1 95.7(9) . . ?
N2 C1 N1 107.16(14) . . ?
N2 C1 P1 128.59(12) . . ?
N1 C1 P1 124.25(12) . . ?
C1 N1 C2 109.31(13) . . ?
C1 N1 C4 126.45(13) . . ?
C2 N1 C4 124.24(13) . . ?
C1 N2 C3 109.20(14) . . ?
C1 N2 C6 126.14(14) . . ?
C3 N2 C6 124.67(14) . . ?
C3 C2 N1 107.20(14) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 107.14(14) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
N1 C4 C5 109.71(9) . 4_575 ?
N1 C4 C5 109.71(9) . . ?
C5 C4 C5 112.96(15) 4_575 . ?
N1 C4 H4 108.1 . . ?
C5 C4 H4 108.1 4_575 . ?
C5 C4 H4 108.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 109.73(10) . 4_575 ?
N2 C6 C7 109.73(10) . . ?
C7 C6 C7 113.04(17) 4_575 . ?
N2 C6 H6 108.1 . . ?
C7 C6 H6 108.1 4_575 . ?
C7 C6 H6 108.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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
P1 C1 1.8249(16) . ?
P1 H1 1.30(2) . ?
C1 N2 1.344(2) . ?
C1 N1 1.347(2) . ?
N1 C2 1.374(2) . ?
N1 C4 1.482(2) . ?
N2 C3 1.379(2) . ?
N2 C6 1.478(2) . ?
C2 C3 1.353(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.5179(16) 4_575 ?
C4 C5 1.5179(16) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.5199(19) 4_575 ?
C6 C7 1.5199(19) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
P1 H1 I1 1.30(2) 3.30(2) 4.0181(2) 114.8(11) .
C2 H2 I1 0.95 3.08 3.8369(16) 138.1 3_666
C5 H5B I1 0.98 3.31 4.2053(15) 152.7 .
C6 H6 I1 1.00 3.18 4.1073(18) 154.7 3_767
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C2 0.000(1) . . . . ?
P1 C1 N1 C2 180.000(1) . . . . ?
N2 C1 N1 C4 180.000(1) . . . . ?
P1 C1 N1 C4 0.000(1) . . . . ?
N1 C1 N2 C3 0.000(1) . . . . ?
P1 C1 N2 C3 180.000(1) . . . . ?
N1 C1 N2 C6 180.000(1) . . . . ?
P1 C1 N2 C6 0.000(1) . . . . ?
C1 N1 C2 C3 0.000(1) . . . . ?
C4 N1 C2 C3 180.000(0) . . . . ?
N1 C2 C3 N2 0.000(1) . . . . ?
C1 N2 C3 C2 0.000(1) . . . . ?
C6 N2 C3 C2 180.000(1) . . . . ?
C1 N1 C4 C5 -117.68(10) . . . 4_575 ?
C2 N1 C4 C5 62.32(10) . . . 4_575 ?
C1 N1 C4 C5 117.68(10) . . . . ?
C2 N1 C4 C5 -62.32(10) . . . . ?
C1 N2 C6 C7 117.61(11) . . . 4_575 ?
C3 N2 C6 C7 -62.39(11) . . . 4_575 ?
C1 N2 C6 C7 -117.61(11) . . . . ?
C3 N2 C6 C7 62.39(11) . . . . ?
