#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/32/4513241.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_4513241
loop_
_publ_author_name
'Makhotkina, Olena'
'Lieffrig, Julien'
'Jeannin, Olivier'
'Fourmigué, Marc'
'Aubert, Emmanuel'
'Espinosa, Enrique'
_publ_section_title
;
 Cocrystal or Salt: Solid State-Controlled Iodine Shift in Crystalline
 Halogen-Bonded Systems
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3464
_journal_paper_doi               10.1021/acs.cgd.5b00535
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C10 H11 I N2 O2, C4 H4 I N O2, C6 H7 N'
_chemical_formula_sum            'C10 H11 I N2 O2'
_chemical_formula_weight         318.11
_chemical_name_common            N-iodo-succinimide/4-picoline
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ya'
_symmetry_space_group_name_H-M   'P 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.296(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7617(4)
_cell_length_b                   14.5317(8)
_cell_length_c                   10.6247(6)
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1137.79(11)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18036
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.94
_exptl_absorpt_coefficient_mu    2.797
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0182P)²+0.9371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0634
_reflns_number_gt                1777
_reflns_number_total             2619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00535_si_002.cif
_cod_data_source_block           NIS-Pic
_cod_depositor_comments
'Adding full bibliography for 4513240--4513246.cif.'
_cod_original_sg_symbol_H-M      P2/a
_cod_database_code               4513241
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'-x, -y, -z'
'x-1/2, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3560(6) 1.1708(3) 0.6020(5) 0.0485(11) Uani 1 1 d .
H1 H 0.4315 1.1387 0.6739 0.058 Uiso 1 1 calc R
C2 C 0.3586(6) 1.2655(3) 0.6053(5) 0.0495(11) Uani 1 1 d .
H2 H 0.4342 1.2958 0.6792 0.059 Uiso 1 1 calc R
C3 C 0.2500 1.3162(4) 0.5000 0.0424(16) Uani 1 2 d S
C4 C 0.2500 1.4191(4) 0.5000 0.0602(19) Uani 1 2 d S
H4A H 0.3341 1.4411 0.5814 0.090 Uiso 0.50 1 calc PR
H4B H 0.1304 1.4411 0.4920 0.090 Uiso 0.50 1 calc PR
H4C H 0.2855 1.4411 0.4266 0.090 Uiso 0.50 1 calc PR
C5 C 0.1534(6) 0.7545(3) 0.3945(5) 0.0471(11) Uani 1 1 d .
C6 C 0.1920(6) 0.6553(3) 0.4274(5) 0.0552(13) Uani 1 1 d .
H6A H 0.2572 0.6281 0.3723 0.066 Uiso 1 1 calc R
H6B H 0.0804 0.6213 0.4151 0.066 Uiso 1 1 calc R
C7 C 0.8237(6) 0.4948(3) 0.1129(5) 0.0488(11) Uani 1 1 d .
C8 C 0.7908(7) 0.5945(3) 0.0741(5) 0.0562(13) Uani 1 1 d .
H8A H 0.7081 0.6220 0.1154 0.067 Uiso 1 1 calc R
H8B H 0.9038 0.6287 0.1010 0.067 Uiso 1 1 calc R
C9 C 0.7500 -0.1671(4) 0.0000 0.062(2) Uani 1 2 d S
H9A H 0.7564 -0.1892 -0.0836 0.093 Uiso 0.50 1 calc PR
H9B H 0.6406 -0.1892 0.0136 0.093 Uiso 0.50 1 calc PR
H9C H 0.8530 -0.1892 0.0700 0.093 Uiso 0.50 1 calc PR
C10 C 0.7500 -0.0648(4) 0.0000 0.0440(17) Uani 1 2 d S
C11 C 0.7579(6) -0.0138(3) -0.1077(4) 0.0499(10) Uani 1 1 d .
H11 H 0.7626 -0.0442 -0.1836 0.060 Uiso 1 1 calc R
C12 C 0.7590(6) 0.0800(3) -0.1056(5) 0.0508(11) Uani 1 1 d .
H12 H 0.7661 0.1119 -0.1797 0.061 Uiso 1 1 calc R
N4 N 0.7500 0.1276(3) 0.0000 0.0431(13) Uani 1 2 d S
N1 N 0.2500 1.1236(3) 0.5000 0.0475(14) Uani 1 2 d S
N2 N 0.2500 0.8071(3) 0.5000 0.0408(13) Uani 1 2 d S
N3 N 0.7500 0.4421(3) 0.0000 0.0452(14) Uani 1 2 d S
O1 O 0.0558(5) 0.7853(2) 0.2904(3) 0.0758(10) Uani 1 1 d .
O2 O 0.8988(5) 0.4639(2) 0.2221(4) 0.0757(10) Uani 1 1 d .
I01 I 0.2500 0.95272(2) 0.5000 0.04166(13) Uani 1 2 d S
I02 I 0.7500 0.29468(3) 0.0000 0.04588(13) Uani 1 2 d S
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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 122.5(4) . .
N1 C1 H1 118.7 . .
C2 C1 H1 118.7 . .
C1 C2 C3 120.8(5) . .
C1 C2 H2 119.6 . .
C3 C2 H2 119.6 . .
C2 C3 C2 115.7(6) 2_556 .
C2 C3 C4 122.2(3) 2_556 .
C2 C3 C4 122.2(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O1 C5 N2 124.4(4) . .
O1 C5 C6 126.3(4) . .
N2 C5 C6 109.2(4) . .
C5 C6 C6 104.4(3) . 2_556
C5 C6 H6A 110.9 . .
C6 C6 H6A 110.9 2_556 .
C5 C6 H6B 110.9 . .
C6 C6 H6B 110.9 2_556 .
H6A C6 H6B 108.9 . .
O2 C7 N3 124.7(4) . .
O2 C7 C8 127.5(4) . .
N3 C7 C8 107.8(4) . .
C8 C8 C7 105.4(3) 2_655 .
C8 C8 H8A 110.7 2_655 .
C7 C8 H8A 110.7 . .
C8 C8 H8B 110.7 2_655 .
C7 C8 H8B 110.7 . .
H8A C8 H8B 108.8 . .
C10 C9 H9A 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C10 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 C11 115.0(6) . 2_655
C11 C10 C9 122.5(3) . .
C11 C10 C9 122.5(3) 2_655 .
C12 C11 C10 121.7(4) . .
C12 C11 H11 119.2 . .
C10 C11 H11 119.2 . .
N4 C12 C11 121.9(4) . .
N4 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C12 N4 C12 117.8(5) . 2_655
C12 N4 I02 121.1(3) . .
C12 N4 I02 121.1(3) 2_655 .
C1 N1 C1 117.8(5) . 2_556
C1 N1 I01 121.1(3) . .
C1 N1 I01 121.1(3) 2_556 .
C5 N2 C5 112.2(5) . 2_556
C5 N2 I01 123.9(2) . .
C5 N2 I01 123.9(2) 2_556 .
C7 N3 C7 112.9(5) . 2_655
C7 N3 I02 123.5(3) . .
C7 N3 I02 123.5(3) 2_655 .
N2 I01 N1 180.000(1) . .
N3 I02 N4 180.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.327(5) .
C1 C2 1.377(6) .
C1 H1 0.9300 .
C2 C3 1.383(5) .
C2 H2 0.9300 .
C3 C2 1.383(5) 2_556
C3 C4 1.495(8) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 O1 1.213(5) .
C5 N2 1.369(5) .
C5 C6 1.492(6) .
C6 C6 1.522(10) 2_556
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 O2 1.209(5) .
C7 N3 1.387(5) .
C7 C8 1.506(6) .
C8 C8 1.502(10) 2_655
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.488(8) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C11 1.381(5) .
C10 C11 1.381(5) 2_655
C11 C12 1.363(6) .
C11 H11 0.9300 .
C12 N4 1.338(5) .
C12 H12 0.9300 .
N4 C12 1.338(5) 2_655
N4 I02 2.428(5) .
N1 C1 1.327(5) 2_556
N1 I01 2.484(5) .
N2 C5 1.369(5) 2_556
N2 I01 2.116(5) .
N3 C7 1.387(5) 2_655
N3 I02 2.142(5) .
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_4
N1 C1 C2 C3 -0.6(7) . .
C1 C2 C3 C2 0.3(3) . 2_556
C1 C2 C3 C4 -179.7(3) . .
O1 C5 C6 C6 -175.4(5) . 2_556
N2 C5 C6 C6 6.2(6) . 2_556
O2 C7 C8 C8 174.7(5) . 2_655
N3 C7 C8 C8 -5.9(6) . 2_655
C11 C10 C11 C12 0.4(3) 2_655 .
C9 C10 C11 C12 -179.6(3) . .
C10 C11 C12 N4 -0.9(7) . .
C11 C12 N4 C12 0.4(3) . 2_655
C11 C12 N4 I02 -179.6(3) . .
C2 C1 N1 C1 0.3(3) . 2_556
C2 C1 N1 I01 -179.7(3) . .
O1 C5 N2 C5 179.1(6) . 2_556
C6 C5 N2 C5 -2.5(2) . 2_556
O1 C5 N2 I01 -0.9(6) . .
C6 C5 N2 I01 177.5(2) . .
O2 C7 N3 C7 -178.3(6) . 2_655
C8 C7 N3 C7 2.3(2) . 2_655
O2 C7 N3 I02 1.7(6) . .
C8 C7 N3 I02 -177.7(2) . .
C5 N2 I01 N1 -111(19) . .
C5 N2 I01 N1 69(20) 2_556 .
C1 N1 I01 N2 -65(21) . .
C1 N1 I01 N2 115(20) 2_556 .
C7 N3 I02 N4 -80(19) . .
C7 N3 I02 N4 100(19) 2_655 .
C12 N4 I02 N3 -68(19) . .
C12 N4 I02 N3 112(19) 2_655 .
