Isomorphous crystal structures of chlorodiacetylene and iododiacetylene derivatives: simultaneous hydrogen and halogen bonds on carbonyl
Baillargeon, Pierre; Rahem, Tarik; Caron-Duval, Édouard; Tremblay, Jacob; Fortin, Cloé; Blais, Étienne; Fan, Victor; Fortin, Daniel; Dory, Yves L.; Acta Crystallographica Section E 73 (2017) 1175–1179; doi:10.1107/S2056989017010155

data_2242117
_publ_section_title
;
 Isomorphous crystal structures of chlorodiacetylene and iododiacetylene
 derivatives: simultaneous hydrogen and halogen bonds on carbonyl
;
_journal_coeditor_code           MW2133
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1175
_journal_page_last               1179
_journal_paper_doi               10.1107/S2056989017010155
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C10 H12 I1 N1 O2'
_chemical_formula_moiety         'C10 H12 I1 N1 O2'
_chemical_formula_sum            'C10 H12 I N O2'
_chemical_formula_weight         305.11
_chemical_name_systematic
;
<i>tert</i>-Butyl (5-iodopenta-2,4-diyn-1-yl)carbamate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.731(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1587(16)
_cell_length_b                   9.0288(13)
_cell_length_c                   12.9899(18)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.26
_cell_volume                     1239.4(3)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2006)
;
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;
WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.02
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17970
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         2.099
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.562
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.322
_refine_diff_density_min         -0.693
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0219
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0203P)^2^+1.7447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.053
_refine_ls_wR_factor_ref         0.0542
_reflns_number_gt                2342
_reflns_number_total             2532
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2242117
_cod_database_fobs_code          2242117
_shelx_hkl_checksum              3505
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