#------------------------------------------------------------------------------
#$Date: 2019-11-17 05:12:00 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/18/7121868.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_7121868
loop_
_publ_author_name
'Cicač-Hudi, M'
'Schlindwein, S. H.'
'Feil, C. M.'
'Nieger, M.'
'Gudat, D.'
_publ_section_title
;
 Isolable N-heterocyclic carbene adducts of the elusive diiodophosphine.
;
_journal_issue                   55
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7645
_journal_page_last               7648
_journal_paper_doi               10.1039/c8cc03972k
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C5 H9 I N2 P, I'
_chemical_formula_sum            'C5 H9 I2 N2 P'
_chemical_formula_weight         381.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/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
;
2018-05-11 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.365(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4578(10)
_cell_length_b                   8.6203(7)
_cell_length_c                   9.8671(7)
_cell_measurement_reflns_used    1546
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.9
_cell_volume                     1025.62(14)
_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 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12371
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_min         2.905
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    6.229
_exptl_absorpt_correction_T_max  0.6678
_exptl_absorpt_correction_T_min  0.2924
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.473
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.00106(7)
_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   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         1666
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0170
_refine_ls_R_factor_gt           0.0142
_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)+(0.0044P)²+1.5883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0274
_refine_ls_wR_factor_ref         0.0282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1545
_reflns_number_total             1666
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc03972k2.cif
_cod_data_source_block           g370_mn_d
_cod_depositor_comments
'Adding full bibliography for 7121868--7121873.cif.'
_cod_database_code               7121868
_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   0.216
_shelx_estimated_absorpt_t_max   0.558
_shelx_res_file
;

    g370_mn_d.res created by SHELXL-2014/7


TITL gud370 in C2/m
CELL 0.71073  13.4578   8.6203   9.8671  90.000 116.365  90.000
ZERR    4.00   0.0010   0.0007   0.0007   0.000   0.003   0.000
LATT 7
SYMM -X, Y, -Z
SFAC C H N P I
UNIT 20 36 8 4 8

OMIT     1   1   2
OMIT     0   2   0

OMIT    -4   4   4

TEMP -143.140
SIZE 0.106 0.156 0.355
REM Tmax: 0.6678 Tmin: 0.2924 (numerical)
REM prism, yellow

L.S. 12
BOND
BOND $H
ACTA
CONF 3.2

FMAP 2
PLAN 20

BIND P1 I2

HTAB

EQIV $1 -x+1/2, -y+1/2, -z+1
HTAB P1 I1_$1
EQIV $2 -x+1/2, -y+1/2, -z+2
HTAB C2 I2_$2
HTAB C3 I2_$2
EQIV $3 x+1/2, y-1/2, z
HTAB C3 I2_$3

WGHT    0.004400    1.588300
EXTI    0.001064
FVAR       0.08609
I2    5    0.037965    0.500000    0.739409    10.50000    0.01542    0.02568 =
         0.01570    0.00000    0.00387    0.00000
I1    5    0.366498    0.500000    0.537865    10.50000    0.02167    0.03919 =
         0.01585    0.00000    0.00809    0.00000
DFIX 1.25 P1 H1
PART -1
P1    4    0.204513    0.478022    0.614371    10.50000    0.01686    0.02450 =
         0.01196    0.00009    0.00217   -0.00009
H1    2    0.171657    0.348988    0.575738    10.50000   -1.50000
PART 0
C1    1    0.300154    0.500000    0.815607    10.50000    0.01237    0.01827 =
         0.01236    0.00000    0.00326    0.00000
N1    3    0.339031    0.374792    0.905594    11.00000    0.01431    0.01803 =
         0.01407    0.00054    0.00436    0.00119
C2    1    0.401043    0.421511    1.052913    11.00000    0.01430    0.02691 =
         0.01251    0.00177    0.00407    0.00106
AFIX  43
H2    2    0.437028    0.355971    1.138406    11.00000   -1.20000
AFIX   0
C3    1    0.317331    0.214107    0.853195    11.00000    0.02844    0.01737 =
         0.02293    0.00001    0.00831    0.00178
AFIX 137
H3A   2    0.237111    0.197307    0.798363    11.00000   -1.50000
H3B   2    0.348730    0.144008    0.940343    11.00000   -1.50000
H3C   2    0.351603    0.193288    0.785752    11.00000   -1.50000

AFIX   0
HKLF 4

REM  gud370 in C2/m
REM R1 =  0.0142 for    1545 Fo > 4sig(Fo)  and  0.0170 for all    1666 data
REM     60 parameters refined using      1 restraints

END

WGHT      0.0044      1.5883

REM Instructions for potential hydrogen bonds
HTAB P1 I1_$1
HTAB C2 I2_$2
HTAB C3 I2_$2
HTAB C3 I2_$3

REM Highest difference peak  0.473,  deepest hole -0.521,  1-sigma level  0.077
Q1    1   0.3830  0.5000  1.0606  10.50000  0.05    0.47
Q2    1  -0.0135  0.5000  0.8455  10.50000  0.05    0.39
Q3    1   0.2609  0.5000  0.7194  10.50000  0.05    0.38
Q4    1   0.3074  0.5000  0.5444  10.50000  0.05    0.38
Q5    1   0.0482  0.5000  0.8047  10.50000  0.05    0.38
Q6    1   0.3233  0.3050  0.8778  11.00000  0.05    0.33
Q7    1   0.3547  0.3898  0.9806  11.00000  0.05    0.32
Q8    1   0.2460  0.0618  0.9420  11.00000  0.05    0.29
Q9    1   0.0989  0.5000  0.5686  10.50000  0.05    0.28
Q10   1   0.4321  0.4610  0.5384  11.00000  0.05    0.28
Q11   1  -0.0171  0.5000  0.7409  10.50000  0.05    0.28
Q12   1   0.4448  0.4035  1.0925  11.00000  0.05    0.27
Q13   1  -0.0777  0.5000  0.7701  10.50000  0.05    0.27
Q14   1   0.3351  0.4280  0.8623  11.00000  0.05    0.26
Q15   1   0.1411  0.5000  0.8557  10.50000  0.05    0.25
Q16   1   0.2982  0.4225  0.8740  11.00000  0.05    0.24
Q17   1   0.4893  0.5000  1.0226  10.50000  0.05    0.24
Q18   1   0.3205  0.4189  0.5392  11.00000  0.05    0.24
Q19   1   0.4661  0.4413  0.4776  11.00000  0.05    0.24
Q20   1   0.0763  0.3276  0.5899  11.00000  0.05    0.23
;
_shelx_res_checksum              14206
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
I2 I 0.03797(2) 0.5000 0.73941(2) 0.02005(5) Uani 1 2 d S T P . .
I1 I 0.36650(2) 0.5000 0.53787(2) 0.02566(5) Uani 1 2 d S T P . .
P1 P 0.20451(6) 0.4780(3) 0.61437(8) 0.0193(5) Uani 0.5 1 d D . P A -1
H1 H 0.172(3) 0.349(3) 0.576(5) 0.029 Uiso 0.5 1 d D U P B -1
C1 C 0.30015(17) 0.5000 0.8156(2) 0.0152(4) Uani 1 2 d S T P . .
N1 N 0.33903(11) 0.37479(15) 0.90559(14) 0.0162(2) Uani 1 1 d . . . . .
C2 C 0.40104(13) 0.42151(19) 1.05291(17) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.4370 0.3560 1.1384 0.022 Uiso 1 1 calc R U . . .
C3 C 0.31733(15) 0.21411(19) 0.8532(2) 0.0241(3) Uani 1 1 d . . . . .
H3A H 0.2371 0.1973 0.7984 0.036 Uiso 1 1 calc R U . . .
H3B H 0.3487 0.1440 0.9403 0.036 Uiso 1 1 calc R U . . .
H3C H 0.3516 0.1933 0.7858 0.036 Uiso 1 1 calc R U . . .
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
I2 0.01542(8) 0.02568(8) 0.01570(7) 0.000 0.00387(5) 0.000
I1 0.02167(9) 0.03919(10) 0.01585(7) 0.000 0.00809(6) 0.000
P1 0.0169(3) 0.0245(15) 0.0120(3) 0.0001(3) 0.0022(2) -0.0001(4)
C1 0.0124(9) 0.0183(10) 0.0124(8) 0.000 0.0033(8) 0.000
N1 0.0143(6) 0.0180(6) 0.0141(6) 0.0005(5) 0.0044(5) 0.0012(5)
C2 0.0143(7) 0.0269(8) 0.0125(6) 0.0018(6) 0.0041(5) 0.0011(6)
C3 0.0284(9) 0.0174(7) 0.0229(8) 0.0000(6) 0.0083(7) 0.0018(6)
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
C1 P1 I1 91.77(7) .
C1 P1 I2 80.90(7) .
I1 P1 I2 169.83(8) .
C1 P1 H1 115(2) .
I1 P1 H1 102.3(19) .
I2 P1 H1 87.2(19) .
N1 C1 N1 106.50(18) 6_565
N1 C1 P1 132.58(12) 6_565
N1 C1 P1 120.74(11) .
C1 N1 C2 109.73(14) .
C1 N1 C3 124.61(13) .
C2 N1 C3 125.66(13) .
C2 C2 N1 107.01(9) 6_565
C2 C2 H2 126.5 6_565
N1 C2 H2 126.5 .
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
I2 P1 3.0063(9) .
I1 P1 2.6114(9) .
P1 C1 1.834(2) .
P1 H1 1.195(19) .
C1 N1 1.3470(18) 6_565
C1 N1 1.3470(18) .
N1 C2 1.3763(19) .
N1 C3 1.462(2) .
C2 C2 1.353(3) 6_565
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 H1 I1 1.195(19) 3.17(2) 4.345(2) 167(3) 7_556
C2 H2 I2 0.95 3.26 4.0721(17) 144.7 7_557
C3 H3B I2 0.98 3.09 4.0503(17) 165.6 7_557
C3 H3C I2 0.98 3.21 4.0552(18) 145.6 3_545
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_4
I1 P1 C1 N1 88.6(2) . 6_565
I2 P1 C1 N1 -84.3(2) . 6_565
I1 P1 C1 N1 -96.90(17) . .
I2 P1 C1 N1 90.20(17) . .
N1 C1 N1 C2 1.0(2) 6_565 .
P1 C1 N1 C2 -174.84(13) . .
N1 C1 N1 C3 -179.40(11) 6_565 .
P1 C1 N1 C3 4.8(3) . .
C1 N1 C2 C2 -0.60(14) . 6_565
C3 N1 C2 C2 179.77(13) . 6_565
