#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:06:39 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230377 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/70/7057097.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_7057097
loop_
_publ_author_name
'Szell, Patrick M. J.'
'Siiskonen, Antti'
'Catalano, Luca'
'Cavallo, Gabriella'
'Terraneo, Giancarlo'
'Priimagi, Arri'
'Bryce, David L.'
'Metrangolo, Pierangelo'
_publ_section_title
;
 Halogen-bond driven self-assembly of triangular macrocycles
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10467
_journal_paper_doi               10.1039/C8NJ00759D
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         '3(C7 H4 I1 N1)'
_chemical_formula_sum            'C21 H12 I3 N3'
_chemical_formula_weight         687.04
_chemical_melting_point          399
_chemical_name_systematic        2-iodoethynylpyridine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-01-22 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0353(7)
_cell_length_b                   14.2760(9)
_cell_length_c                   14.2688(9)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.33
_cell_volume                     2247.9(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.971
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26238
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.248
_diffrn_reflns_theta_min         2.333
_exptl_absorpt_coefficient_mu    4.181
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.377
_exptl_crystal_size_min          0.188
_refine_diff_density_max         1.716
_refine_diff_density_min         -2.507
_refine_diff_density_rms         0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     366
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.1183
_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)+(0.0676P)²+92.2532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2951
_refine_ls_wR_factor_ref         0.2970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2655
_reflns_number_total             2968
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00759d2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7057094--7057097.cif.'
_cod_database_code               7057097
_shelx_shelxl_version_number     2016/6
_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   0.261
_shelx_estimated_absorpt_t_max   0.507
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.4536(3) 0.87021(18) 0.80471(14) 0.0522(6) Uani 0.5 1 d D . P A -1
N1 N 0.693(3) 0.7971(16) 0.4880(16) 0.048(4) Uani 0.5 1 d D . P A -1
C1 C 0.761(2) 0.7946(15) 0.4073(15) 0.042(4) Uani 0.5 1 d D . P A -1
H1 H 0.796620 0.738071 0.385892 0.050 Uiso 0.5 1 calc R U P A -1
C2 C 0.774(2) 0.8776(14) 0.3579(15) 0.046(4) Uani 0.5 1 d D . P A -1
H2 H 0.817724 0.877056 0.300317 0.055 Uiso 0.5 1 calc R U P A -1
C3 C 0.727(3) 0.9605(14) 0.3900(16) 0.052(5) Uani 0.5 1 d D . P A -1
H3 H 0.741010 1.016587 0.355884 0.062 Uiso 0.5 1 calc R U P A -1
C4 C 0.659(3) 0.9633(16) 0.4713(17) 0.048(4) Uani 0.5 1 d D . P A -1
H4 H 0.624842 1.020036 0.493463 0.058 Uiso 0.5 1 calc R U P A -1
C5 C 0.644(3) 0.8796(15) 0.5192(18) 0.054(4) Uani 0.5 1 d D . P A -1
C6 C 0.586(3) 0.8812(18) 0.6019(15) 0.050(6) Uani 0.5 1 d D . P A -1
C7 C 0.539(4) 0.881(4) 0.668(2) 0.0522(6) Uani 0.5 1 d D . P A -1
I2 I 0.4104(4) 0.5037(2) 0.8700(3) 0.0479(5) Uani 0.5 1 d D . P B -1
N2 N 0.356(3) 0.8587(13) 0.9927(19) 0.054(4) Uani 0.5 1 d D . P B -1
C8 C 0.329(3) 0.9386(15) 1.0417(17) 0.048(4) Uani 0.5 1 d D . P B -1
H8 H 0.359928 0.997683 1.022575 0.058 Uiso 0.5 1 calc R U P B -1
C9 C 0.255(2) 0.9311(15) 1.1192(15) 0.052(5) Uani 0.5 1 d D . P B -1
H9 H 0.233724 0.986261 1.152517 0.062 Uiso 0.5 1 calc R U P B -1
C10 C 0.211(2) 0.8461(13) 1.1498(16) 0.046(4) Uani 0.5 1 d D . P B -1
H10 H 0.155488 0.843782 1.200534 0.055 Uiso 0.5 1 calc R U P B -1
C11 C 0.249(2) 0.7638(14) 1.1066(16) 0.042(4) Uani 0.5 1 d D . P B -1
H11 H 0.229337 0.703990 1.131719 0.050 Uiso 0.5 1 calc R U P B -1
C12 C 0.316(3) 0.7734(14) 1.0246(18) 0.048(4) Uani 0.5 1 d D . P B -1
C13 C 0.348(3) 0.6955(17) 0.9771(19) 0.059(8) Uani 0.5 1 d D . P B -1
C14 C 0.379(5) 0.642(3) 0.928(4) 0.0499(6) Uani 0.5 1 d D . P B -1
I3 I 0.6308(3) 0.62395(16) 0.5738(2) 0.0499(6) Uani 0.5 1 d D . P C -1
N3 N 0.472(4) 0.3335(16) 0.780(3) 0.056(5) Uani 0.5 1 d D . P C -1
C15 C 0.441(4) 0.2484(15) 0.818(3) 0.059(6) Uani 0.5 1 d D . P C -1
H15 H 0.391632 0.246325 0.873009 0.071 Uiso 0.5 1 calc R U P C -1
C16 C 0.479(5) 0.1657(15) 0.778(3) 0.054(6) Uani 0.5 1 d D . P C -1
H16 H 0.458739 0.107106 0.804976 0.065 Uiso 0.5 1 calc R U P C -1
C17 C 0.548(5) 0.1692(14) 0.697(3) 0.054(6) Uani 0.5 1 d D . P C -1
H17 H 0.572841 0.112796 0.667335 0.065 Uiso 0.5 1 calc R U P C -1
C18 C 0.580(5) 0.2550(14) 0.659(3) 0.059(6) Uani 0.5 1 d D . P C -1
H18 H 0.631677 0.257897 0.605587 0.071 Uiso 0.5 1 calc R U P C -1
C19 C 0.536(5) 0.3365(14) 0.699(3) 0.056(5) Uani 0.5 1 d D . P C -1
C20 C 0.569(3) 0.4198(16) 0.661(2) 0.057(7) Uani 0.5 1 d D . P C -1
C21 C 0.583(7) 0.489(4) 0.631(6) 0.0479(5) Uani 0.5 1 d D . P C -1
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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 121(2)
N1 C1 C2 117.7(18)
N1 C1 H1 121.2
C2 C1 H1 121.2
C3 C2 C1 121.7(17)
C3 C2 H2 119.2
C1 C2 H2 119.2
C2 C3 C4 120.8(15)
C2 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C5 117.0(16)
C3 C4 H4 121.5
C5 C4 H4 121.5
C6 C5 N1 119.3(19)
C6 C5 C4 118.4(17)
N1 C5 C4 122.2(18)
C7 C6 C5 179(4)
C6 C7 I1 175(4)
C8 N2 C12 120(2)
N2 C8 C9 118.3(18)
N2 C8 H8 120.8
C9 C8 H8 120.8
C10 C9 C8 122.1(17)
C10 C9 H9 118.9
C8 C9 H9 118.9
C9 C10 C11 119.9(15)
C9 C10 H10 120.0
C11 C10 H10 120.0
C10 C11 C12 116.6(15)
C10 C11 H11 121.7
C12 C11 H11 121.7
C13 C12 N2 118.6(18)
C13 C12 C11 118.6(17)
N2 C12 C11 122.7(18)
C14 C13 C12 169(4)
C13 C14 I2 158(5)
C19 N3 C15 120(2)
N3 C15 C16 120.9(19)
N3 C15 H15 119.6
C16 C15 H15 119.6
C17 C16 C15 119.2(18)
C17 C16 H16 120.4
C15 C16 H16 120.4
C16 C17 C18 120.0(16)
C16 C17 H17 120.0
C18 C17 H17 120.0
C19 C18 C17 119.3(17)
C19 C18 H18 120.3
C17 C18 H18 120.3
C20 C19 N3 120(2)
C20 C19 C18 118.7(18)
N3 C19 C18 120.6(19)
C21 C20 C19 173(6)
C20 C21 I3 174(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C7 2.16(4)
N1 C1 1.370(16)
N1 C5 1.370(16)
C1 C2 1.386(15)
C1 H1 0.9500
C2 C3 1.372(15)
C2 H2 0.9500
C3 C4 1.380(15)
C3 H3 0.9500
C4 C5 1.387(16)
C4 H4 0.9500
C5 C6 1.34(3)
C6 C7 1.08(4)
I2 C14 2.17(4)
N2 C8 1.372(16)
N2 C12 1.374(16)
C8 C9 1.378(15)
C8 H8 0.9500
C9 C10 1.377(15)
C9 H9 0.9500
C10 C11 1.390(15)
C10 H10 0.9500
C11 C12 1.392(16)
C11 H11 0.9500
C12 C13 1.35(3)
C13 C14 1.09(4)
I3 C21 2.17(4)
N3 C19 1.363(16)
N3 C15 1.373(16)
C15 C16 1.383(15)
C15 H15 0.9500
C16 C17 1.379(15)
C16 H16 0.9500
C17 C18 1.387(15)
C17 H17 0.9500
C18 C19 1.384(16)
C18 H18 0.9500
C19 C20 1.35(3)
C20 C21 1.08(4)
