The iodine–oxygen halogen bond: solid-state structures of 3-iodopropiolamides
Kratzer, Philipp; Ramming, Bastian; Römisch, Steven; Maas, Gerhard; CrystEngComm 17 (2015) 4486–; doi:10.1039/C5CE00365B

data_1519671
_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 H8 I N O'
_chemical_formula_weight         249.04
_chemical_melting_point          425
_chemical_name_systematic        3-Iodo-1-(pyrrolidin-1-yl)prop-2-yn-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_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                 95.996(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.3440(3)
_cell_length_b                   15.8341(5)
_cell_length_c                   10.4832(4)
_cell_measurement_reflns_used    1615
_cell_measurement_temperature    179.95(10)
_cell_measurement_theta_max      25.6900
_cell_measurement_theta_min      3.9110
_cell_volume                     1707.63(10)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      179.95(10)
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4166
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.930
_exptl_absorpt_coefficient_mu    3.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_description       'prismatic, cut from larger crystal'
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1855
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0203P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1416
_reflns_number_total             1855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce00365b2.cif
_cod_data_source_block           pk248
_cod_depositor_comments
'Adding full bibliography for 1519670--1519675.cif.'
_cod_database_code               1519671
_shelxl_version_number           2014/6
_shelx_res_checksum              17569