#------------------------------------------------------------------------------
#$Date: 2015-07-10 22:50:17 +0200 (vie 10 de jul de 2015) $
#$Revision: 143412 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/96/1519674.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_1519674
loop_
_publ_author_name
'Kratzer, Philipp'
'Ramming, Bastian'
'Römisch, Steven'
'Maas, Gerhard'
_publ_section_title
;
 The iodine--oxygen halogen bond: solid-state structures of
 3-iodopropiolamides
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4486
_journal_paper_doi               10.1039/C5CE00365B
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C5 H5 I N2 O'
_chemical_formula_weight         236.01
_chemical_melting_point          423
_chemical_name_systematic        '3-Iodopropiolamide acetonitrile complex'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-01-20 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.202(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8120(4)
_cell_length_b                   8.1725(2)
_cell_length_c                   9.2790(3)
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.8540
_cell_measurement_theta_min      3.3540
_cell_volume                     801.38(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2000-2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3655
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.151
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.956
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0242
_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)+(0.0168P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1409
_reflns_number_total             1641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce00365b2.cif
_cod_data_source_block           PK286_2
_cod_depositor_comments
'Adding full bibliography for 1519670--1519675.cif.'
_cod_database_code               1519674
_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.
;
_shelxl_version_number           2014/6
_shelx_res_file
;
TITL PK286_2 C3H2NOIxCH3CN P2(1)/c OD Oct14
REM P2(1)/c (#14 in standard setting)
CELL 0.71073  10.812005   8.172459   9.279050  90.0000 102.2019  90.0000
ZERR    4.00   0.000378   0.000212   0.000349   0.0000   0.0037   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2
SFAC C H N O I
UNIT 20.00 20.00 8.00 4.00 4.00
MORE 0
TEMP -123
LIST 6
L.S. 4
BOND
FMAP 2
PLAN -10
SHEL 11. 0.80
ACTA
WGHT    0.016800
FVAR       4.10290
MOLE   1
I1    5    0.234083   -0.233807    0.313516    11.00000    0.02805    0.02324 =
         0.03887   -0.00432    0.00639   -0.00657
O     4    0.423505    0.329722    0.569455    11.00000    0.03954    0.02378 =
         0.01917   -0.00147    0.00788   -0.00666
N1    3    0.455920    0.356064    0.337826    11.00000    0.03725    0.02379 =
         0.01839   -0.00607    0.00826   -0.00765
C1    1    0.416267    0.276369    0.442289    11.00000    0.02066    0.02003 =
         0.02344    0.00181    0.00456    0.00197
C2    1    0.359558    0.115456    0.401749    11.00000    0.02812    0.02628 =
         0.01988    0.00079    0.00664   -0.00275
C3    1    0.312826   -0.015804    0.373056    11.00000    0.02744    0.02833 =
         0.02627    0.00249    0.00639   -0.00094
H1    2    0.486968    0.452441    0.354000    11.00000    0.03711
H2    2    0.448514    0.306859    0.257413    11.00000    0.02315

MOLE 2
C4    1    0.105535   -0.654005    0.142619    11.00000    0.03514    0.03851 =
         0.03993   -0.00163    0.00909   -0.01392
C5    1    0.096108   -0.806729    0.060071    11.00000    0.04540    0.04511 =
         0.05484   -0.01229    0.01179   -0.00108
AFIX 137
H5A   2    0.057358   -0.785632   -0.043608    11.00000   -1.50000
H5B   2    0.043758   -0.884496    0.101108    11.00000   -1.50000
H5C   2    0.180867   -0.852804    0.067178    11.00000   -1.50000
AFIX   0
N2    3    0.111218   -0.537874    0.207505    11.00000    0.06519    0.04396 =
         0.07434   -0.01420    0.01436   -0.02566

MOLE   2
HKLF 4

REM  PK286_2 C3H2NOIxCH3CN P2(1)/c OD Oct14
REM R1 =  0.0242 for    1409 Fo > 4sig(Fo)  and  0.0314 for all    1641 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0157      0.0000

REM Highest difference peak  0.454,  deepest hole -0.634,  1-sigma level  0.106
Q1    1   0.1276 -0.2310  0.2504  11.00000  0.05    0.45
Q2    1   0.2153  0.2824  0.3011  11.00000  0.05    0.35
Q3    1   0.3773 -0.2736  0.1504  11.00000  0.05    0.35
Q4    1   0.5663  0.1820  0.3968  11.00000  0.05    0.33
Q5    1   0.2703  0.1814  0.5019  11.00000  0.05    0.33
Q6    1   0.4945  0.0289  0.3531  11.00000  0.05    0.32
Q7    1   0.1596 -0.3086  0.2215  11.00000  0.05    0.32
Q8    1   0.1768 -0.2218  0.3942  11.00000  0.05    0.32
Q9    1   0.3099  0.0983  0.4124  11.00000  0.05    0.32
Q10   1   0.0557 -0.2979  0.2940  11.00000  0.05    0.31
;
_shelx_res_checksum              78256
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
I1 I 0.23408(2) -0.23381(2) 0.31352(2) 0.03016(10) Uani 1 1 d . .
O O 0.4235(2) 0.3297(2) 0.5695(2) 0.0272(5) Uani 1 1 d . .
N1 N 0.4559(3) 0.3561(3) 0.3378(3) 0.0261(6) Uani 1 1 d . .
C1 C 0.4163(3) 0.2764(3) 0.4423(3) 0.0214(7) Uani 1 1 d . .
C2 C 0.3596(3) 0.1155(4) 0.4017(3) 0.0245(7) Uani 1 1 d . .
C3 C 0.3128(3) -0.0158(4) 0.3731(3) 0.0272(7) Uani 1 1 d . .
H1 H 0.487(3) 0.452(4) 0.354(4) 0.037(10) Uiso 1 1 d . .
H2 H 0.449(3) 0.307(4) 0.257(4) 0.023(9) Uiso 1 1 d . .
C4 C 0.1055(3) -0.6540(5) 0.1426(4) 0.0377(9) Uani 1 1 d . .
C5 C 0.0961(4) -0.8067(5) 0.0601(5) 0.0483(10) Uani 1 1 d . .
H5A H 0.0574 -0.7856 -0.0436 0.072 Uiso 1 1 calc R U
H5B H 0.0438 -0.8845 0.1011 0.072 Uiso 1 1 calc R U
H5C H 0.1809 -0.8528 0.0672 0.072 Uiso 1 1 calc R U
N2 N 0.1112(3) -0.5379(4) 0.2075(4) 0.0612(10) Uani 1 1 d . .
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
I1 0.02805(15) 0.02324(13) 0.03887(16) -0.00432(9) 0.00639(11) -0.00657(8)
O 0.0395(14) 0.0238(11) 0.0192(11) -0.0015(9) 0.0079(10) -0.0067(10)
N1 0.0373(17) 0.0238(15) 0.0184(15) -0.0061(13) 0.0083(13) -0.0076(13)
C1 0.0207(16) 0.0200(14) 0.0234(17) 0.0018(13) 0.0046(14) 0.0020(12)
C2 0.0281(18) 0.0263(16) 0.0199(16) 0.0008(13) 0.0066(14) -0.0027(14)
C3 0.0274(18) 0.0283(17) 0.0263(17) 0.0025(14) 0.0064(15) -0.0009(14)
C4 0.035(2) 0.039(2) 0.040(2) -0.0016(18) 0.0091(17) -0.0139(17)
C5 0.045(2) 0.045(2) 0.055(3) -0.012(2) 0.012(2) -0.0011(19)
N2 0.065(2) 0.044(2) 0.074(3) -0.0142(19) 0.014(2) -0.0257(18)
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'
O O 0.0106 0.0060 '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
O C1 N1 124.1(3)
O C1 C2 119.8(3)
N1 C1 C2 116.1(3)
C3 C2 C1 178.0(3)
C2 C3 I1 176.9(3)
N2 C4 C5 178.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C3 2.001(3)
O C1 1.245(4)
N1 C1 1.313(4)
C1 C2 1.466(4)
C2 C3 1.192(4)
C4 N2 1.119(5)
C4 C5 1.457(5)
