#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:06:28 +0100 (dom 17 de nov de 2019) $
#$Revision: 230376 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/71/7057163.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_7057163
loop_
_publ_author_name
'Szell, Patrick M. J.'
'Dragon, Julien'
'Zablotny, Scott'
'Harrigan, Stephen R.'
'Gabidullin, Bulat'
'Bryce, David L.'
_publ_section_title
;
 Mechanochemistry and cocrystallization of 3-iodoethynylbenzoic acid with
 nitrogen-containing heterocycles: concurrent halogen and hydrogen bonding
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10493
_journal_paper_doi               10.1039/C8NJ00437D
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C9 H5 I O2'
_chemical_formula_sum            'C9 H5 I O2'
_chemical_formula_weight         272.03
_chemical_melting_point          455
_chemical_name_common            '3-iodoethynylbenzoic acid'
_chemical_name_systematic        '3-(iodoethynyl)benzoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-16 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.119(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7508(4)
_cell_length_b                   28.730(2)
_cell_length_c                   6.5630(5)
_cell_measurement_reflns_used    3758
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      2.84
_cell_volume                     895.17(12)
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14806
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.399
_diffrn_reflns_theta_min         1.418
_exptl_absorpt_coefficient_mu    3.531
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.018
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.457
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0330
_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)+(0.0368P)²+1.0995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1751
_reflns_number_total             2244
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00437d2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7057163--7057168.cif.'
_cod_database_code               7057163
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.438
_shelx_estimated_absorpt_t_max   0.966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I -0.28562(6) 0.26575(2) 0.78104(4) 0.05119(12) Uani 1 1 d . .
C1 C -0.1034(8) 0.31057(13) 0.5942(6) 0.0408(9) Uani 1 1 d . .
C2 C 0.0132(8) 0.33658(12) 0.4847(6) 0.0375(8) Uani 1 1 d . .
C3 C 0.1487(7) 0.36828(12) 0.3496(6) 0.0347(7) Uani 1 1 d . .
C4 C 0.0698(8) 0.37089(14) 0.1440(6) 0.0423(9) Uani 1 1 d . .
H4 H -0.0742 0.3510 0.0901 0.051 Uiso 1 1 calc R U
C5 C 0.1982(9) 0.40215(15) 0.0169(6) 0.0468(10) Uani 1 1 d . .
H5 H 0.1423 0.4034 -0.1234 0.056 Uiso 1 1 calc R U
C6 C 0.4070(8) 0.43155(14) 0.0922(6) 0.0422(9) Uani 1 1 d . .
H6 H 0.4945 0.4530 0.0043 0.051 Uiso 1 1 calc R U
C7 C 0.4882(7) 0.42949(12) 0.2980(6) 0.0344(8) Uani 1 1 d . .
C8 C 0.3615(7) 0.39794(12) 0.4263(6) 0.0342(8) Uani 1 1 d . .
H8 H 0.4193 0.3965 0.5663 0.041 Uiso 1 1 calc R U
C9 C 0.7091(7) 0.46078(12) 0.3863(6) 0.0353(8) Uani 1 1 d . .
O1 O 0.7729(6) 0.45942(10) 0.5722(4) 0.0448(6) Uani 1 1 d . .
O2 O 0.8255(7) 0.48849(11) 0.2600(5) 0.0464(7) Uani 1 1 d . .
H2 H 0.938(12) 0.502(2) 0.309(9) 0.069(19) Uiso 1 1 d . .
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'
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
C2 C1 I1 177.9(4)
C1 C2 C3 178.7(4)
C4 C3 C8 118.8(4)
C4 C3 C2 121.5(3)
C8 C3 C2 119.8(3)
C5 C4 C3 120.8(4)
C5 C4 H4 119.6
C3 C4 H4 119.6
C6 C5 C4 120.6(4)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 119.4(4)
C5 C6 H6 120.3
C7 C6 H6 120.3
C8 C7 C6 120.3(3)
C8 C7 C9 118.3(3)
C6 C7 C9 121.3(3)
C7 C8 C3 120.1(3)
C7 C8 H8 119.9
C3 C8 H8 119.9
O1 C9 O2 123.7(4)
O1 C9 C7 120.4(3)
O2 C9 C7 115.9(3)
C9 O2 H2 111(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 1.998(4)
C1 C2 1.188(5)
C2 C3 1.439(5)
C3 C4 1.389(5)
C3 C8 1.402(5)
C4 C5 1.383(6)
C4 H4 0.9500
C5 C6 1.380(6)
C5 H5 0.9500
C6 C7 1.392(5)
C6 H6 0.9500
C7 C8 1.389(5)
C7 C9 1.484(5)
C8 H8 0.9500
C9 O1 1.247(5)
C9 O2 1.288(5)
O2 H2 0.72(6)
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
C8 C3 C4 C5 0.0(6)
C2 C3 C4 C5 178.8(4)
C3 C4 C5 C6 -0.3(6)
C4 C5 C6 C7 0.1(6)
C5 C6 C7 C8 0.4(6)
C5 C6 C7 C9 -179.3(4)
C6 C7 C8 C3 -0.7(5)
C9 C7 C8 C3 179.0(3)
C4 C3 C8 C7 0.5(5)
C2 C3 C8 C7 -178.3(3)
C8 C7 C9 O1 -1.9(5)
C6 C7 C9 O1 177.8(4)
C8 C7 C9 O2 178.1(3)
C6 C7 C9 O2 -2.2(5)
