#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/65/1506533.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_1506533
loop_
_publ_author_name
'Goroff, Nancy S.'
'Curtis, Sean M.'
'Webb, Jeffrey A.'
'Fowler, Frank W.'
'Lauher, Joseph W.'
_publ_section_title
;
 Designed cocrystals based on the pyridine-iodoalkyne halogen bond.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              1891
_journal_page_last               1893
_journal_paper_doi               10.1021/ol050184s
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C18 H14 I2 N4 O2'
_chemical_formula_weight         572.13
_chemical_name_common            4mepyox-ICCCCI
_chemical_name_systematic
; 
1-4 Co-crystal 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.708(4)
_cell_angle_beta                 96.629(5)
_cell_angle_gamma                90.382(4)
_cell_formula_units_Z            2
_cell_length_a                   5.0225(14)
_cell_length_b                   13.367(4)
_cell_length_c                   16.614(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1027.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_sigmaI/netI    0.1475
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4648
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    3.078
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ABSCOR
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .1
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                3459
_reflns_number_total             4475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol050184ssi20050128_053614.cif
_cod_data_source_block           4mepyox-icccci
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506533
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
I1 I 0.2607(2) 0.36231(8) 0.47275(6) 0.0751(5) Uani 1 1 d .
I2 I 0.7598(3) 0.19105(10) 0.01758(6) 0.0926(5) Uani 1 1 d .
N1 N 0.337(2) 0.9568(9) 0.5714(7) 0.057(3) Uani 1 1 d .
H1 H 0.1806 0.9711 0.5530 0.069 Uiso 1 1 calc R
O1 O 0.778(2) 0.9598(8) 0.5534(6) 0.068(3) Uani 1 1 d .
C9 C 0.242(3) 1.0769(12) 0.7534(10) 0.081(5) Uani 1 1 d .
H9 H 0.3385 1.1158 0.7290 0.097 Uiso 1 1 calc R
N4 N 0.649(2) 0.4270(9) 0.9030(6) 0.058(3) Uani 1 1 d .
H4 H 0.8063 0.4582 0.9205 0.069 Uiso 1 1 calc R
C5 C 0.542(3) 0.9774(11) 0.5368(8) 0.047(4) Uani 1 1 d .
C15 C 0.756(3) 0.3576(12) 0.7558(8) 0.052(4) Uani 1 1 d .
C13 C 0.453(3) 0.4575(11) 0.9538(8) 0.049(4) Uani 1 1 d .
C18 C 0.998(4) 0.4598(12) 0.6926(10) 0.081(5) Uani 1 1 d .
H18 H 1.0598 0.5268 0.6950 0.097 Uiso 1 1 calc R
C16 C 0.825(3) 0.2663(12) 0.6862(8) 0.071(5) Uani 1 1 d .
H16 H 0.7725 0.1975 0.6821 0.085 Uiso 1 1 calc R
C19 C 0.853(3) 0.4593(13) 0.7569(8) 0.067(5) Uani 1 1 d .
H19 H 0.8179 0.5235 0.8006 0.081 Uiso 1 1 calc R
C7 C 0.358(3) 0.9104(10) 0.6405(8) 0.053(4) Uani 1 1 d .
H7A H 0.2821 0.8368 0.6145 0.064 Uiso 1 1 calc R
H7B H 0.5462 0.9074 0.6596 0.064 Uiso 1 1 calc R
C1 C 0.392(4) 0.3340(12) 0.3529(10) 0.075(5) Uani 1 1 d .
C10 C 0.225(3) 0.9677(12) 0.7179(8) 0.053(4) Uani 1 1 d .
C14 C 0.593(3) 0.3433(12) 0.8209(9) 0.077(5) Uani 1 1 d .
H14A H 0.4040 0.3409 0.7999 0.092 Uiso 1 1 calc R
H14B H 0.6310 0.2750 0.8268 0.092 Uiso 1 1 calc R
C12 C -0.045(3) 0.9814(16) 0.8292(9) 0.079(5) Uani 1 1 d .
H12 H -0.1476 0.9441 0.8531 0.095 Uiso 1 1 calc R
N3 N 1.059(3) 0.3740(12) 0.6268(8) 0.077(4) Uani 1 1 d .
C8 C 0.115(4) 1.1314(12) 0.8275(9) 0.078(5) Uani 1 1 d .
H8 H 0.1355 1.2062 0.8512 0.093 Uiso 1 1 calc R
C3 C 0.538(4) 0.2826(13) 0.1972(11) 0.085(6) Uani 1 1 d .
C11 C 0.077(3) 0.9216(12) 0.7588(9) 0.064(4) Uani 1 1 d .
H11 H 0.0574 0.8468 0.7385 0.077 Uiso 1 1 calc R
C2 C 0.458(4) 0.3099(12) 0.2792(11) 0.087(6) Uani 1 1 d .
N2 N -0.030(3) 1.0849(12) 0.8653(9) 0.080(4) Uani 1 1 d .
C4 C 0.617(4) 0.2526(15) 0.1284(10) 0.101(7) Uani 1 1 d .
C17 C 0.969(3) 0.2782(15) 0.6247(11) 0.079(5) Uani 1 1 d .
H17 H 1.0065 0.2164 0.5790 0.095 Uiso 1 1 calc R
O2 O 0.214(2) 0.4269(8) 0.9337(6) 0.068(3) Uani 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'
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_3
C5 N1 C7 124.5(12) .
C10 C9 C8 119.8(15) .
C13 N4 C14 119.1(11) .
O1 C5 N1 126.7(13) .
O1 C5 C5 120.1(16) 2_676
N1 C5 C5 113.1(16) 2_676
C16 C15 C19 115.0(13) .
C16 C15 C14 119.9(14) .
C19 C15 C14 125.2(13) .
O2 C13 N4 126.9(12) .
O2 C13 C13 119.2(16) 2_667
N4 C13 C13 113.9(16) 2_667
N3 C18 C19 126.2(15) .
C17 C16 C15 120.6(15) .
C18 C19 C15 118.6(14) .
C10 C7 N1 116.4(11) .
C2 C1 I1 175.1(15) .
C11 C10 C9 114.1(14) .
C11 C10 C7 125.9(14) .
C9 C10 C7 120.0(14) .
N4 C14 C15 111.9(11) .
N2 C12 C11 125.7(16) .
C18 N3 C17 116.0(14) .
N2 C8 C9 125.0(15) .
C4 C3 C2 175(2) .
C10 C11 C12 121.9(15) .
C1 C2 C3 179(2) .
C12 N2 C8 113.5(15) .
C3 C4 I2 174.4(17) .
N3 C17 C16 123.7(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.072(15) .
I2 C4 1.943(16) .
N1 C5 1.307(16) .
N1 C7 1.488(15) .
O1 C5 1.229(15) .
C9 C10 1.355(17) .
C9 C8 1.407(19) .
N4 C13 1.337(16) .
N4 C14 1.403(15) .
C5 C5 1.57(3) 2_676
C15 C16 1.416(18) .
C15 C19 1.433(19) .
C15 C14 1.494(18) .
C13 O2 1.232(14) .
C13 C13 1.55(3) 2_667
C18 N3 1.327(17) .
C18 C19 1.364(19) .
C16 C17 1.37(2) .
C7 C10 1.470(16) .
C1 C2 1.230(19) .
C10 C11 1.347(18) .
C12 N2 1.286(18) .
C12 C11 1.364(18) .
N3 C17 1.342(18) .
C8 N2 1.303(18) .
C3 C4 1.18(2) .
C3 C2 1.38(2) .
