#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:31:39 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158181.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_7158181
loop_
_publ_author_name
'Abeysekera, Amila M.'
'Averkiev, Boris B.'
'Le Magueres, Pierre'
'Aakeröy, Christer B'
_publ_section_title
;
 Intermolecular binding preferences of haloethynyl halogen-bond donors as
 a function of molecular electrostatic potentials in a family of
 N-(pyridin-2-yl)amides.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6671
_journal_page_last               6681
_journal_paper_doi               10.1039/d1ob01133b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C14 H9 I N2 O'
_chemical_formula_sum            'C14 H9 I N2 O'
_chemical_formula_weight         348.13
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-04-26
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.244(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.25520(10)
_cell_length_b                   15.3923(3)
_cell_length_c                   16.4781(3)
_cell_measurement_reflns_used    16617
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      33.5650
_cell_measurement_theta_min      2.4790
_cell_volume                     1319.13(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  84.00   0.50   60.00    --   12.42  57.00 -60.00  100
  2  ω     -2.00  60.00   0.50   60.00    --   12.42  57.00 -90.00  124
  3  ω     -3.00  26.00   0.50   60.00    --   12.42  77.00  60.00   58
  4  ω     -2.00  79.00   0.50   60.00    --   12.42  57.00 150.00  162
  5  ω     15.00  52.00   0.50   60.00    --   12.42-112.00 123.00   74
  6  ω    -57.00  -7.00   0.50   60.00    --   12.42 -19.00 -30.00  100
  7  ω    -62.00   5.00   0.50   60.00    --   12.42 -19.00-150.00  134
  8  ω    -84.00   1.00   0.50   60.00    --  -12.58 -57.00 -60.00  170
  9  ω     50.00  75.00   0.50   60.00    --   12.42-178.00  30.00   50
 10  ω     40.00  83.00   0.50   60.00    --   12.42-178.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062624000
_diffrn_orient_matrix_UB_12      0.0112230000
_diffrn_orient_matrix_UB_13      -0.0419856000
_diffrn_orient_matrix_UB_21      0.1268740000
_diffrn_orient_matrix_UB_22      0.0168026000
_diffrn_orient_matrix_UB_23      0.0078779000
_diffrn_orient_matrix_UB_31      0.0496875000
_diffrn_orient_matrix_UB_32      -0.0414094000
_diffrn_orient_matrix_UB_33      -0.0081962000
_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  0.0239
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.573
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.024
_refine_diff_density_max         1.385
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0377P)²+0.5979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4037
_reflns_number_total             4674
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           Bz-act-I-Form-2
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158181
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H10N4O4I1
_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_max   0.944
_shelx_estimated_absorpt_t_min   0.554
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C3(H3), C5(H5), C6(H6), C14(H14), C18(H18), C15(H15), C16(H16),
 C17(H17)
;
_olex2_date_sample_data_collection 2021-04-22
_olex2_date_sample_submission    2021-01-12
_olex2_exptl_crystal_mounting_method 'mounted on a MiTegen loop'
_olex2_submission_original_sample_id 'Bz-act_1 (Form II)'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.713
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I9 I 0.34356(3) 0.26065(2) 0.81958(2) 0.03943(6) Uani 1 1 d . . . . .
O12 O 0.9591(2) 0.70864(9) 0.47106(8) 0.0341(3) Uani 1 1 d . . . . .
N2 N 0.3918(2) 0.62013(9) 0.60208(8) 0.0260(2) Uani 1 1 d . . . . .
N10 N 0.5526(2) 0.69784(9) 0.50316(8) 0.0269(3) Uani 1 1 d . . . . .
H10 H 0.399075 0.721690 0.493589 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5542(3) 0.48079(10) 0.65078(9) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.5743(3) 0.62417(9) 0.55349(9) 0.0223(2) Uani 1 1 d . . . . .
C3 C 0.3837(3) 0.55020(11) 0.64900(9) 0.0272(3) Uani 1 1 d . . . . .
H3 H 0.253537 0.547433 0.683428 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4631(4) 0.35256(13) 0.74702(12) 0.0383(4) Uani 1 1 d . . . . .
C5 C 0.7486(3) 0.48741(10) 0.60153(10) 0.0272(3) Uani 1 1 d . . . . .
H5 H 0.871774 0.442247 0.601525 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7610(3) 0.55997(10) 0.55278(10) 0.0256(3) Uani 1 1 d . . . . .
H6 H 0.893562 0.565908 0.519590 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7407(3) 0.73722(10) 0.46710(10) 0.0265(3) Uani 1 1 d . . . . .
C7 C 0.5184(3) 0.40818(11) 0.70213(10) 0.0316(3) Uani 1 1 d . . . . .
C13 C 0.6601(3) 0.82032(11) 0.42419(10) 0.0302(3) Uani 1 1 d . . . . .
C14 C 0.4235(4) 0.82998(14) 0.37596(12) 0.0410(4) Uani 1 1 d . . . . .
H14 H 0.304020 0.783311 0.369853 0.049 Uiso 1 1 calc R U . . .
C18 C 0.8325(4) 0.88901(14) 0.43213(15) 0.0468(5) Uani 1 1 d . . . . .
H18 H 0.996598 0.882211 0.464173 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3625(4) 0.90880(19) 0.33649(15) 0.0542(6) Uani 1 1 d . . . . .
H15 H 0.201637 0.915264 0.302511 0.065 Uiso 1 1 calc R U . . .
C16 C 0.5316(5) 0.97743(16) 0.34596(17) 0.0581(6) Uani 1 1 d . . . . .
H16 H 0.485881 1.031303 0.319716 0.070 Uiso 1 1 calc R U . . .
C17 C 0.7666(5) 0.96782(16) 0.39345(18) 0.0596(6) Uani 1 1 d . . . . .
H17 H 0.884348 1.014997 0.399908 0.072 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 C1 118.15(13) . . ?
C1 N10 H10 116.0 . . ?
C11 N10 H10 116.0 . . ?
C11 N10 C1 127.93(13) . . ?
C3 C4 C5 117.01(14) . . ?
C3 C4 C7 118.25(14) . . ?
C5 C4 C7 124.74(15) . . ?
N2 C1 N10 112.84(13) . . ?
N2 C1 C6 122.59(13) . . ?
C6 C1 N10 124.55(13) . . ?
N2 C3 C4 124.02(14) . . ?
N2 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
C7 C8 I9 175.91(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.72(14) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.44(14) . . ?
C5 C6 H6 120.8 . . ?
O12 C11 N10 123.33(15) . . ?
O12 C11 C13 122.29(15) . . ?
N10 C11 C13 114.36(14) . . ?
C8 C7 C4 172.2(2) . . ?
C14 C13 C11 122.30(17) . . ?
C14 C13 C18 119.56(17) . . ?
C18 C13 C11 118.13(16) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C18 H18 119.8 . . ?
C13 C18 C17 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I9 C8 2.0103(18) . ?
O12 C11 1.222(2) . ?
N2 C1 1.3363(19) . ?
N2 C3 1.330(2) . ?
N10 H10 0.8800 . ?
N10 C1 1.3997(19) . ?
N10 C11 1.366(2) . ?
C4 C3 1.392(2) . ?
C4 C5 1.397(2) . ?
C4 C7 1.430(2) . ?
C1 C6 1.394(2) . ?
C3 H3 0.9500 . ?
C8 C7 1.194(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C11 C13 1.493(2) . ?
C13 C14 1.384(3) . ?
C13 C18 1.386(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.391(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.372(4) . ?
C17 H17 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 C11 C13 C14 139.48(19) . . . . ?
O12 C11 C13 C18 -39.1(3) . . . . ?
N2 C1 C6 C5 3.1(2) . . . . ?
N10 C1 C6 C5 -175.31(15) . . . . ?
N10 C11 C13 C14 -42.3(2) . . . . ?
N10 C11 C13 C18 139.05(18) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C1 N2 C3 C4 0.1(2) . . . . ?
C1 N10 C11 O12 4.3(3) . . . . ?
C1 N10 C11 C13 -173.87(15) . . . . ?
C3 N2 C1 N10 175.94(14) . . . . ?
C3 N2 C1 C6 -2.7(2) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C5 C4 C3 N2 1.9(2) . . . . ?
C11 N10 C1 N2 157.00(16) . . . . ?
C11 N10 C1 C6 -24.4(3) . . . . ?
C11 C13 C14 C15 -178.86(19) . . . . ?
C11 C13 C18 C17 -179.9(2) . . . . ?
C7 C4 C3 N2 -177.93(15) . . . . ?
C7 C4 C5 C6 178.47(15) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C13 C18 C17 C16 -1.1(4) . . . . ?
C14 C13 C18 C17 1.4(3) . . . . ?
C14 C15 C16 C17 1.5(4) . . . . ?
C18 C13 C14 C15 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
