#------------------------------------------------------------------------------
#$Date: 2020-12-19 04:23:18 +0100 (Sat 19 de Dec de 2020) $
#$Revision: 259993 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/61/7706108.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_7706108
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         'C5 H10 N2 P, I'
_chemical_formula_sum            'C5 H10 I N2 P'
_chemical_formula_weight         256.02
_space_group_crystal_system      orthorhombic
_space_group_IT_number           59
_space_group_name_Hall           '-P 2ab 2a'
_space_group_name_H-M_alt        'P m m n :2'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4133(14)
_cell_length_b                   7.1479(11)
_cell_length_c                   7.5050(11)
_cell_measurement_reflns_used    409
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      24.971
_cell_measurement_theta_min      2.714
_cell_volume                     451.33(12)
_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_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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  0.0645
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4551
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         2.714
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.653
_exptl_absorpt_correction_T_max  0.8917
_exptl_absorpt_correction_T_min  0.5327
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'BLESSING 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_description       prism
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.081
_refine_diff_density_max         2.867
_refine_diff_density_min         -2.254
_refine_diff_density_rms         0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.288
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     38
_refine_ls_number_reflns         447
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.276
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0290P)²+12.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                409
_reflns_number_total             447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03633a2.cif
_cod_data_source_block           g480_mn
_cod_original_sg_symbol_H-M      'P m m n'
_cod_database_code               7706108
_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   0.687
_shelx_estimated_absorpt_t_max   0.756
_shelx_res_file
;

    g480_mn.res created by SHELXL-2014/7


CELL  0.71073    8.4133    7.1479    7.5050    90.000    90.000    90.000
ZERR        2    0.0014    0.0011    0.0011     0.000     0.000     0.000
LATT   1
SYMM     0.50000 - X ,    0.50000 - Y ,              Z
SYMM     0.50000 + X ,            - Y ,            - Z
SYMM             - X ,    0.50000 + Y ,            - Z
SFAC  C H I  N  P
UNIT    10  20  2   4   2

TEMP -143.170
SIZE 0.081 0.097 0.111
REM Tmax: 0.8917 Tmin: 0.5327 (numerical)
REM prism, colourless

L.S. 16
BOND
BOND $H
ACTA
CONF

FMAP 2
PLAN 20

HTAB

EQIV $1 x, y+1, z
HTAB P1 I1_$1
EQIV $2 -x+2, -y+1, -z+1
HTAB C2 I1_$2
HTAB C3 I1_$2

ISOR 0.005 P1 I1 C2

RIGU

DFIX 1.25 0.01 P1 H1A P1 H1B
DFIX 2.10 0.02 H1A H1B

WGHT    0.029000   12.350000
FVAR       0.26829
P1    5    0.750000    0.750000    1.006781    10.25000    0.05267    0.07689 =
         0.00664    0.00000    0.00000    0.00000
PART -1
H1A   2    0.611588    0.686406    1.007941    10.25000   -1.50000
H1B   2    0.761479    0.914194    1.062654    10.25000   -1.50000
PART 0
N1    4    0.878265    0.750000    0.659559    10.50000    0.02996    0.02830 =
         0.01288    0.00000   -0.00121    0.00000
C1    1    0.750000    0.750000    0.763547    10.25000    0.02933    0.03518 =
         0.00955    0.00000    0.00000    0.00000
C2    1    0.829237    0.750000    0.485032    10.50000    0.02995    0.03119 =
         0.01504    0.00000   -0.00040    0.00000
AFIX  43
H2    2    0.896022    0.750000    0.382964    10.50000   -1.20000
AFIX   0
C3    1    1.042802    0.750000    0.720562    10.50000    0.03151    0.05755 =
         0.02517    0.00000   -0.00568    0.00000
AFIX 137
H3A   2    1.051841    0.826352    0.828545    10.50000   -1.50000
H3B   2    1.111218    0.802153    0.627280    10.50000   -1.50000
H3C   2    1.075939    0.621495    0.746863    10.50000   -1.50000
AFIX   0

I1    3    0.750000    0.250000    0.780265    10.25000    0.04258    0.03754 =
         0.01122    0.00000    0.00000    0.00000
HKLF 4 1  0.0000  0.0000  1.0000  1.0000  0.0000  0.0000  0.0000  1.0000  0.0000

REM
REM R1 =  0.0639 for     409 Fo > 4sig(Fo)  and  0.0735 for all     447 data
REM     38 parameters refined using     45 restraints

END

WGHT      0.0288     12.3462

REM Instructions for potential hydrogen bonds
HTAB P1 I1_$1
HTAB C2 I1_$2
HTAB C3 I1_$2

REM Highest difference peak  2.867,  deepest hole -2.254,  1-sigma level  0.272
Q1    1   0.7500  0.1037  0.7833  10.50000  0.05    2.87
Q2    1   0.6536  0.2500  0.7818  10.50000  0.05    1.83
Q3    1   0.6346  0.0928  0.7984  11.00000  0.05    1.06
Q4    1   0.6624  0.1481  0.6745  11.00000  0.05    1.01
Q5    1   0.7500  0.7500  0.4272  10.25000  0.05    0.94
Q6    1   0.6761  0.7500  1.1470  10.50000  0.05    0.80
Q7    1   0.8303  0.6600  0.4960  11.00000  0.05    0.76
Q8    1   0.7500  0.8752  0.9772  10.50000  0.05    0.71
Q9    1   0.7500  0.9411  0.8160  10.50000  0.05    0.71
Q10   1   0.7500  0.8554  1.0415  10.50000  0.05    0.70
Q11   1   0.7500  0.7500  0.5771  10.25000  0.05    0.68
Q12   1   0.7500  1.0262  0.9405  10.50000  0.05    0.66
Q13   1   1.2500  0.7500  0.6569  10.25000  0.05    0.61
Q14   1   0.7500  0.0233  0.6498  10.50000  0.05    0.61
Q15   1   0.9389  0.7500  0.4150  10.50000  0.05    0.59
Q16   1   1.0560  0.7500  0.3448  10.50000  0.05    0.57
Q17   1   0.9602  0.4663  0.7069  11.00000  0.05    0.57
Q18   1   0.8313  0.6170  0.5989  11.00000  0.05    0.56
Q19   1   0.6524  0.7500  0.9787  10.50000  0.05    0.56
Q20   1   0.4819  0.7500  1.0163  10.50000  0.05    0.53
;
_shelx_res_checksum              79961
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, 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 0.7500 0.7500 1.0068(8) 0.0454(19) Uani 1 4 d DS TU P . .
H1A H 0.612(17) 0.69(5) 1.01(6) 0.068 Uiso 0.25 1 d D U P A -1
H1B H 0.76(5) 0.914(17) 1.06(4) 0.068 Uiso 0.25 1 d D U P B -1
N1 N 0.8783(15) 0.7500 0.6596(15) 0.024(3) Uani 1 2 d S TU P . .
C1 C 0.7500 0.7500 0.764(3) 0.025(4) Uani 1 4 d S TU P . .
C2 C 0.8292(18) 0.7500 0.4850(18) 0.025(3) Uani 1 2 d S TU P . .
H2 H 0.8960 0.7500 0.3830 0.030 Uiso 1 2 calc R U P . .
C3 C 1.0428(19) 0.7500 0.721(2) 0.038(4) Uani 1 2 d S TU P . .
H3A H 1.0518 0.8264 0.8285 0.057 Uiso 0.5 1 calc R U P . .
H3B H 1.1112 0.8022 0.6273 0.057 Uiso 0.5 1 calc R U P . .
H3C H 1.0759 0.6215 0.7469 0.057 Uiso 0.5 1 calc R U P . .
I1 I 0.7500 0.2500 0.78027(18) 0.0304(6) Uani 1 4 d S TU P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.053(4) 0.077(5) 0.007(2) 0.000 0.000 0.000
N1 0.030(5) 0.028(8) 0.013(4) 0.000 -0.001(3) 0.000
C1 0.029(7) 0.035(13) 0.010(5) 0.000 0.000 0.000
C2 0.030(5) 0.031(5) 0.015(4) 0.000 0.000(3) 0.000
C3 0.032(6) 0.058(12) 0.025(7) 0.000 -0.006(5) 0.000
I1 0.0426(10) 0.0375(10) 0.0112(7) 0.000 0.000 0.000
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'
I I -0.4742 1.8119 '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'
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 H1A 90(10) . . ?
C1 P1 H1B 110(10) . . ?
H1A P1 H1B 114(2) . . ?
C1 N1 C2 108.4(13) . . ?
C1 N1 C3 125.8(12) . . ?
C2 N1 C3 125.8(13) . . ?
N1 C1 N1 108.2(16) 2_665 . ?
N1 C1 P1 125.9(8) 2_665 . ?
N1 C1 P1 125.9(8) . . ?
C2 C2 N1 107.5(8) 2_665 . ?
C2 C2 H2 126.3 2_665 . ?
N1 C2 H2 126.3 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 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 1.83(2) . ?
P1 H1A 1.250(11) . ?
P1 H1B 1.250(11) . ?
N1 C1 1.332(16) . ?
N1 C2 1.373(17) . ?
N1 C3 1.46(2) . ?
C1 N1 1.332(16) 2_665 ?
C2 C2 1.33(3) 2_665 ?
C2 H2 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 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 H1B I1 1.250(11) 3.2(3) 3.958(3) 119(19) 1_565
C2 H2 I1 0.95 3.22 4.062(15) 148.6 5_766
C3 H3B I1 0.98 3.30 4.143(17) 145.9 5_766
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
C2 N1 C1 N1 0.000(3) . . . 2_665 ?
C3 N1 C1 N1 180.000(3) . . . 2_665 ?
C2 N1 C1 P1 180.000(1) . . . . ?
C3 N1 C1 P1 0.000(3) . . . . ?
C1 N1 C2 C2 0.000(3) . . . 2_665 ?
C3 N1 C2 C2 180.000(3) . . . 2_665 ?
