#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/07/7210742.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_7210742
loop_
_publ_author_name
'Khavasi, Hamid Reza'
'Tehrani, Alireza Azhdari'
_publ_section_title
;
 Effect of halogen bonding interaction on supramolecular assembly of
 halogen-substituted phenylpyrazinamides
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              3222
_journal_paper_doi               10.1039/c3ce40093j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C11 H8 I N3 O'
_chemical_formula_weight         325.10
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.258(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.3086(3)
_cell_length_b                   12.7522(6)
_cell_length_c                   19.6521(11)
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.62
_cell_volume                     1078.93(11)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6556
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_T_max  0.8111
_exptl_absorpt_correction_T_min  0.7226
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.012
_refine_diff_density_min         -1.135
_refine_diff_density_rms         0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0743P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                2109
_reflns_number_total             2596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40093j.txt
_cod_data_source_block           d:\determination\solution\c41\khc41
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_original_formula_sum        'C11 H8 I1 N3 O'
_cod_database_code               7210742
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.7793(13) 0.4988(5) -0.2411(3) 0.0274(11) Uani 1 1 d .
H1 H 1.8436 0.5629 -0.2229 0.033 Uiso 1 1 calc R
C2 C 1.8749(12) 0.4693(5) -0.3046(3) 0.0263(11) Uani 1 1 d .
H2 H 2.0039 0.5145 -0.3276 0.032 Uiso 1 1 calc R
C3 C 1.6098(12) 0.3186(5) -0.2981(3) 0.0264(11) Uani 1 1 d .
H3 H 1.5449 0.2547 -0.3166 0.032 Uiso 1 1 calc R
C4 C 1.5139(10) 0.3460(4) -0.2343(3) 0.0181(10) Uani 1 1 d .
C5 C 1.3125(10) 0.2721(4) -0.1956(3) 0.0201(10) Uani 1 1 d .
C6 C 1.0297(10) 0.2666(4) -0.0874(3) 0.0195(10) Uani 1 1 d .
C7 C 0.9210(11) 0.3337(4) -0.0372(3) 0.0183(9) Uani 1 1 d .
H7 H 0.9682 0.4048 -0.0381 0.022 Uiso 1 1 calc R
C8 C 0.7419(11) 0.2931(4) 0.0138(3) 0.0207(10) Uani 1 1 d .
C9 C 0.6658(12) 0.1871(5) 0.0151(3) 0.0252(11) Uani 1 1 d .
H9 H 0.5462 0.1600 0.0494 0.030 Uiso 1 1 calc R
C10 C 0.7715(14) 0.1233(4) -0.0354(3) 0.0264(12) Uani 1 1 d .
H10 H 0.7216 0.0524 -0.0349 0.032 Uiso 1 1 calc R
C11 C 0.9510(12) 0.1617(5) -0.0873(3) 0.0258(11) Uani 1 1 d .
H11 H 1.0168 0.1173 -0.1214 0.031 Uiso 1 1 calc R
N1 N 1.5973(10) 0.4373(4) -0.2055(2) 0.0236(9) Uani 1 1 d .
N2 N 1.7919(12) 0.3800(4) -0.3343(3) 0.0318(11) Uani 1 1 d .
N3 N 1.2178(9) 0.3126(4) -0.1363(2) 0.0201(8) Uani 1 1 d .
H3B H 1.2811 0.3752 -0.1271 0.024 Uiso 1 1 calc R
O1 O 1.2437(10) 0.1857(4) -0.2179(2) 0.0328(9) Uani 1 1 d .
I1 I 0.58677(7) 0.39413(3) 0.089043(17) 0.02308(14) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.032(2) 0.026(3) 0.025(3) -0.003(2) 0.010(2) -0.004(2)
C2 0.026(2) 0.030(3) 0.024(3) 0.005(2) 0.008(2) 0.003(2)
C3 0.030(2) 0.030(3) 0.020(3) -0.001(2) 0.009(2) 0.000(2)
C4 0.0149(19) 0.022(3) 0.017(2) 0.000(2) 0.0040(17) 0.0046(17)
C5 0.016(2) 0.027(3) 0.017(3) -0.001(2) 0.0044(17) 0.0016(18)
C6 0.0147(18) 0.029(3) 0.016(2) 0.003(2) 0.0030(16) -0.0020(18)
C7 0.021(2) 0.017(2) 0.017(2) 0.0004(19) 0.0036(17) -0.0006(17)
C8 0.020(2) 0.027(3) 0.016(2) -0.003(2) 0.0052(17) 0.0039(19)
C9 0.027(2) 0.026(3) 0.023(3) 0.003(2) 0.007(2) -0.005(2)
C10 0.033(3) 0.021(3) 0.026(3) -0.002(2) 0.009(2) -0.007(2)
C11 0.027(2) 0.027(3) 0.023(3) -0.006(2) 0.010(2) -0.003(2)
N1 0.023(2) 0.025(2) 0.023(2) 0.0000(19) 0.0049(17) -0.0005(17)
N2 0.035(2) 0.038(3) 0.024(3) -0.003(2) 0.012(2) 0.001(2)
N3 0.0229(18) 0.020(2) 0.018(2) -0.0021(18) 0.0094(15) -0.0032(16)
O1 0.042(2) 0.030(2) 0.028(2) -0.0065(19) 0.0144(18) -0.0084(18)
I1 0.02269(18) 0.0286(2) 0.0185(2) -0.00310(15) 0.00891(12) -0.00016(13)
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
N1 C1 C2 121.2(5)
N1 C1 H1 119.4
C2 C1 H1 119.4
N2 C2 C1 123.2(5)
N2 C2 H2 118.4
C1 C2 H2 118.4
N2 C3 C4 122.6(6)
N2 C3 H3 118.7
C4 C3 H3 118.7
N1 C4 C3 121.4(5)
N1 C4 C5 118.8(5)
C3 C4 C5 119.9(5)
O1 C5 N3 125.3(5)
O1 C5 C4 121.4(5)
N3 C5 C4 113.2(5)
C11 C6 C7 120.2(5)
C11 C6 N3 123.5(5)
C7 C6 N3 116.3(5)
C8 C7 C6 119.4(5)
C8 C7 H7 120.3
C6 C7 H7 120.3
C7 C8 C9 120.9(5)
C7 C8 I1 118.9(4)
C9 C8 I1 120.3(4)
C10 C9 C8 118.4(5)
C10 C9 H9 120.8
C8 C9 H9 120.8
C9 C10 C11 122.1(5)
C9 C10 H10 119.0
C11 C10 H10 119.0
C6 C11 C10 119.0(5)
C6 C11 H11 120.5
C10 C11 H11 120.5
C1 N1 C4 116.4(5)
C2 N2 C3 115.2(5)
C5 N3 C6 129.0(5)
C5 N3 H3B 115.5
C6 N3 H3B 115.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.328(7)
C1 C2 1.382(8)
C1 H1 0.9300
C2 N2 1.322(8)
C2 H2 0.9300
C3 N2 1.334(8)
C3 C4 1.381(7)
C3 H3 0.9300
C4 N1 1.337(7)
C4 C5 1.507(7)
C5 O1 1.218(7)
C5 N3 1.354(7)
C6 C11 1.380(8)
C6 C7 1.400(7)
C6 N3 1.409(6)
C7 C8 1.390(7)
C7 H7 0.9300
C8 C9 1.392(8)
C8 I1 2.090(5)
C9 C10 1.374(8)
C9 H9 0.9300
C10 C11 1.393(8)
C10 H10 0.9300
C11 H11 0.9300
N3 H3B 0.8600
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
N1 C1 C2 N2 0.6(9)
N2 C3 C4 N1 0.7(8)
N2 C3 C4 C5 -179.0(5)
N1 C4 C5 O1 -176.0(5)
C3 C4 C5 O1 3.6(7)
N1 C4 C5 N3 5.0(6)
C3 C4 C5 N3 -175.3(5)
C11 C6 C7 C8 2.1(7)
N3 C6 C7 C8 -178.1(4)
C6 C7 C8 C9 -1.0(7)
C6 C7 C8 I1 179.2(3)
C7 C8 C9 C10 -0.1(8)
I1 C8 C9 C10 179.8(4)
C8 C9 C10 C11 0.0(9)
C7 C6 C11 C10 -2.2(8)
N3 C6 C11 C10 178.0(5)
C9 C10 C11 C6 1.1(9)
C2 C1 N1 C4 0.2(8)
C3 C4 N1 C1 -0.8(7)
C5 C4 N1 C1 178.8(5)
C1 C2 N2 C3 -0.7(9)
C4 C3 N2 C2 0.1(8)
O1 C5 N3 C6 1.2(9)
C4 C5 N3 C6 -179.9(5)
C11 C6 N3 C5 11.5(8)
C7 C6 N3 C5 -168.3(5)
