#------------------------------------------------------------------------------
#$Date: 2015-07-10 22:50:17 +0200 (vie 10 de jul de 2015) $
#$Revision: 143412 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/96/1519670.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_1519670
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            'C7 H6 I N O'
_chemical_formula_weight         247.03
_chemical_melting_point          441
_chemical_name_systematic
1-(2,5-Dihydro-1-1H-pyrrol-1-yl)-3-iodoprop-2-yn-1-one
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                 96.447(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5832(5)
_cell_length_b                   15.6631(6)
_cell_length_c                   9.8457(5)
_cell_measurement_reflns_used    1987
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.3610
_cell_measurement_theta_min      3.8700
_cell_volume                     1621.76(13)
_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_temperature      180(2)
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3819
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.880
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82549
_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    2.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin platelet'
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.032
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0383P)²+5.4810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                1270
_reflns_number_total             1542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00365b2.cif
_cod_data_source_block           pk276
_cod_depositor_comments
'Adding full bibliography for 1519670--1519675.cif.'
_cod_original_cell_volume        1621.77(13)
_cod_database_code               1519670
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I I 0.78585(3) 0.47051(2) 0.23780(4) 0.03855(16) Uani 1 1 d .
O O 0.7951(3) 0.8073(2) 0.1981(4) 0.0400(9) Uani 1 1 d .
N N 0.9445(4) 0.7769(3) 0.0584(4) 0.0312(10) Uani 1 1 d .
C1 C 0.8579(4) 0.7551(3) 0.1402(5) 0.0268(11) Uani 1 1 d .
C2 C 0.8409(4) 0.6640(3) 0.1625(5) 0.0311(11) Uani 1 1 d .
C3 C 0.8250(5) 0.5908(3) 0.1888(6) 0.0357(12) Uani 1 1 d .
C4 C 1.0205(5) 0.7184(4) -0.0167(6) 0.0418(13) Uani 1 1 d .
H4A H 0.9658 0.6825 -0.0820 0.063 Uiso 1 1 calc R
H4B H 1.0752 0.6811 0.0463 0.063 Uiso 1 1 calc R
C5 C 1.0975(5) 0.7794(5) -0.0890(6) 0.0490(16) Uani 1 1 d .
H5 H 1.1582 0.7624 -0.1479 0.059 Uiso 1 1 calc R
C6 C 1.0722(6) 0.8593(5) -0.0621(6) 0.0494(16) Uani 1 1 d .
H6 H 1.1124 0.9068 -0.0990 0.059 Uiso 1 1 calc R
C7 C 0.9725(5) 0.8666(3) 0.0332(6) 0.0368(13) Uani 1 1 d .
H7A H 1.0054 0.8962 0.1188 0.055 Uiso 1 1 calc R
H7B H 0.8964 0.8971 -0.0099 0.055 Uiso 1 1 calc R
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 0.0386(2) 0.0260(2) 0.0517(3) 0.00091(16) 0.00794(17) 0.00183(15)
O 0.042(2) 0.031(2) 0.050(2) -0.0051(18) 0.0191(18) -0.0014(17)
N 0.034(2) 0.029(2) 0.032(2) -0.0011(19) 0.0103(18) -0.0036(19)
C1 0.028(2) 0.025(3) 0.027(3) 0.000(2) 0.005(2) -0.003(2)
C2 0.027(2) 0.033(3) 0.034(3) -0.006(2) 0.006(2) 0.000(2)
C3 0.038(3) 0.018(2) 0.052(3) -0.002(2) 0.007(2) -0.001(2)
C4 0.042(3) 0.045(3) 0.040(3) -0.007(3) 0.014(3) 0.003(3)
C5 0.044(3) 0.072(5) 0.033(3) -0.007(3) 0.014(3) -0.009(3)
C6 0.048(3) 0.064(4) 0.037(3) 0.007(3) 0.008(3) -0.023(3)
C7 0.036(3) 0.033(3) 0.042(3) 0.009(2) 0.004(2) -0.009(2)
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 C7 121.0(4)
C1 N C4 126.7(4)
C7 N C4 112.3(4)
O C1 N 123.6(4)
O C1 C2 119.8(4)
N C1 C2 116.6(4)
C3 C2 C1 175.8(6)
C2 C3 I 175.7(5)
N C4 C5 101.5(4)
C6 C5 C4 112.4(5)
C5 C6 C7 112.0(5)
N C7 C6 101.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I C3 1.999(5)
O C1 1.233(6)
N C1 1.331(6)
N C7 1.463(6)
N C4 1.472(7)
C1 C2 1.458(7)
C2 C3 1.192(7)
C4 C5 1.488(8)
C5 C6 1.313(9)
C6 C7 1.493(8)
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
C7 N C1 O 1.1(8)
C4 N C1 O -178.3(5)
C7 N C1 C2 -177.7(4)
C4 N C1 C2 2.9(8)
C1 N C4 C5 179.7(5)
C7 N C4 C5 0.3(6)
N C4 C5 C6 0.0(7)
C4 C5 C6 C7 -0.2(8)
C1 N C7 C6 -179.8(5)
C4 N C7 C6 -0.4(6)
C5 C6 C7 N 0.4(7)
