#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/96/1519675.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_1519675
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            'C4 H4 I N O'
_chemical_formula_weight         208.98
_chemical_melting_point          449
_chemical_name_systematic        3-Iodo-N-methyl-propiolamide
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-20 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1674(10)
_cell_length_b                   4.1334(3)
_cell_length_c                   9.0094(6)
_cell_measurement_reflns_used    1349
_cell_measurement_temperature    180.1(2)
_cell_measurement_theta_max      29.4840
_cell_measurement_theta_min      4.5280
_cell_volume                     602.07(7)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1756
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87902
_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    2.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         992
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0232
_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)+(0.0255P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0528
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                935
_reflns_number_total             992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00365b2.cif
_cod_data_source_block           added_by_encifer
_cod_depositor_comments
'Adding full bibliography for 1519670--1519675.cif.'
_cod_original_sg_symbol_H-M      'P c a 2(1)'
_cod_database_code               1519675
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014/6
_shelx_res_file
;
TITL PK281 C4H4NOI Pca2(1) OD SEPT14
REM Pca2(1) (#29, found as Pc2(1)b in cab setting)
CELL 0.71073  16.167416   4.133417   9.009375  90.0000  90.0000  90.0000
ZERR    4.00   0.001000   0.000265   0.000617   0.0000   0.0000   0.0000
LATT -1
SYMM -x,-y, z+1/2
SYMM  x+1/2,-y, z
SYMM -x+1/2, y, z+1/2
SFAC C H N O I
UNIT 16 16 4 4 4
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
MORE 0
SHEL 11. 0.80
L.S. 4
BOND
FMAP 2
PLAN -10
TEMP -93
CONF
ACTA
REM H.N   2    0.728555    0.459250    0.323041    11.00000    0.07750

WGHT    0.025500
FVAR       5.16539
I     5    1.023664   -0.109521    0.410151    11.00000    0.02106    0.02691 =
         0.02395    0.00696   -0.00405    0.00205
O     4    0.820020    0.347110    0.010464    11.00000    0.02401    0.05073 =
         0.01060   -0.00110    0.00194    0.00803
N     3    0.736864    0.446000    0.208493    11.00000    0.02044    0.03430 =
         0.01564    0.00067    0.00289    0.00694
AFIX  43
H0    2    0.730384    0.429027    0.305162    11.00000   -2.30000
AFIX   0
C1    1    0.805361    0.330600    0.146275    11.00000    0.01692    0.02642 =
         0.02212    0.00100   -0.00146   -0.00035
C2    1    0.865687    0.189954    0.245409    11.00000    0.02184    0.02919 =
         0.01765    0.00090    0.00294    0.00392
C3    1    0.923779    0.070057    0.310012    11.00000    0.02207    0.02806 =
         0.01627    0.00269   -0.00148    0.00040
C4    1    0.672742    0.598748    0.121174    11.00000    0.03022    0.04105 =
         0.02501   -0.00237   -0.00313    0.01153
AFIX 137
H4A   2    0.696417    0.779597    0.065113    11.00000   -1.50000
H4B   2    0.629214    0.679528    0.187184    11.00000   -1.50000
H4C   2    0.649151    0.440608    0.052065    11.00000   -1.50000

MOLE   2
AFIX   0
HKLF 4

REM  PK281 C4H4NOI Pca2(1) OD SEPT14
REM R1 =  0.0232 for     935 Fo > 4sig(Fo)  and  0.0253 for all     992 data
REM     65 parameters refined using      1 restraints

END

WGHT      0.0253      0.0000

REM Highest difference peak  0.471,  deepest hole -0.817,  1-sigma level  0.132
Q1    1   0.5549  0.4769  0.1462  11.00000  0.05    0.47
Q2    1   1.1202  0.0118  0.4136  11.00000  0.05    0.43
Q3    1   0.9465  0.4856  0.1738  11.00000  0.05    0.42
Q4    1   0.9372  0.3853  0.2160  11.00000  0.05    0.42
Q5    1   0.8933  0.5057  0.1248  11.00000  0.05    0.41
Q6    1   0.8136 -0.0074  0.4059  11.00000  0.05    0.39
Q7    1   0.8756  0.4011  0.4138  11.00000  0.05    0.35
Q8    1   0.6020  0.5222  0.1989  11.00000  0.05    0.35
Q9    1   1.1628  0.1677  0.3831  11.00000  0.05    0.33
Q10   1   1.0202 -0.1399  0.5840  11.00000  0.05    0.33
;
_shelx_res_checksum              12061
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
I I 1.02366(2) -0.10952(9) 0.41015(10) 0.02398(17) Uani 1 1 d . .
O O 0.8200(3) 0.3471(14) 0.0105(6) 0.0284(13) Uani 1 1 d . .
N N 0.7369(4) 0.4460(16) 0.2085(8) 0.0235(16) Uani 1 1 d . .
H0 H 0.7304 0.4290 0.3052 0.054 Uiso 1 1 calc R U
C1 C 0.8054(5) 0.3306(19) 0.1463(9) 0.0218(18) Uani 1 1 d . .
C2 C 0.8657(4) 0.1900(19) 0.2454(8) 0.0229(16) Uani 1 1 d . .
C3 C 0.9238(5) 0.0701(18) 0.3100(9) 0.0221(16) Uani 1 1 d . .
C4 C 0.6727(5) 0.5987(19) 0.1212(10) 0.032(2) Uani 1 1 d . .
H4A H 0.6964 0.7796 0.0651 0.048 Uiso 1 1 calc R U
H4B H 0.6292 0.6795 0.1872 0.048 Uiso 1 1 calc R U
H4C H 0.6492 0.4406 0.0521 0.048 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
I 0.0211(2) 0.0269(2) 0.0240(3) 0.0070(4) -0.0041(4) 0.00205(14)
O 0.024(3) 0.051(3) 0.011(3) -0.001(3) 0.002(2) 0.008(3)
N 0.020(4) 0.034(3) 0.016(4) 0.001(3) 0.003(3) 0.007(3)
C1 0.017(4) 0.026(4) 0.022(5) 0.001(4) -0.001(4) 0.000(3)
C2 0.022(4) 0.029(4) 0.018(4) 0.001(4) 0.003(3) 0.004(3)
C3 0.022(4) 0.028(4) 0.016(4) 0.003(3) -0.001(3) 0.000(3)
C4 0.030(5) 0.041(5) 0.025(4) -0.002(4) -0.003(4) 0.012(4)
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
C1 N C4 121.6(7)
O C1 N 123.5(8)
O C1 C2 120.0(7)
N C1 C2 116.5(7)
C3 C2 C1 170.2(8)
C2 C3 I 176.7(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I C3 1.993(8)
O C1 1.248(9)
N C1 1.330(11)
N C4 1.446(10)
C1 C2 1.445(11)
C2 C3 1.211(10)
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
C4 N C1 O 0.7(12)
C4 N C1 C2 178.7(7)
