#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/07/7210747.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_7210747
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_moiety         'C11 H8 F1 N3 O1'
_chemical_formula_sum            'C11 H8 F N3 O'
_chemical_formula_weight         217.20
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
_cell_angle_beta                 109.455(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8921(1)
_cell_length_b                   27.1491(4)
_cell_length_c                   6.4010(2)
_cell_measurement_reflns_used    3399
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.48
_cell_volume                     965.47(4)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.1012
_diffrn_reflns_av_sigmaI/netI    0.1020
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3399
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            Colorles
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.012
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0710
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                2202
_reflns_number_total             2302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40093j.txt
_cod_data_source_block           d:\determination\solution\khc28-2\3f-
_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/c
_cod_original_formula_sum        'C11 H8 F1 N3 O1'
_cod_database_code               7210747
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.82005(9) 0.44552(2) 1.23400(9) 0.02753(15) Uani 1 1 d .
H1 H 0.9849 0.4483 1.3006 0.033 Uiso 1 1 calc R
C2 C 0.67127(11) 0.46604(2) 1.33870(11) 0.02817(18) Uani 1 1 d .
H2 H 0.7407 0.4811 1.4730 0.034 Uiso 1 1 calc R
C3 C 0.34568(12) 0.44095(2) 1.05564(10) 0.02685(15) Uani 1 1 d .
H3 H 0.1808 0.4390 0.9873 0.032 Uiso 1 1 calc R
C4 C 0.49435(13) 0.41936(2) 0.95311(10) 0.02299(13) Uani 1 1 d .
C5 C 0.38266(13) 0.39272(2) 0.73703(9) 0.02361(14) Uani 1 1 d .
C6 C 0.49298(12) 0.34348(2) 0.45782(9) 0.02229(13) Uani 1 1 d .
C7 C 0.26384(11) 0.339560(19) 0.30044(9) 0.02438(14) Uani 1 1 d .
H7 H 0.1323 0.3544 0.3205 0.029 Uiso 1 1 calc R
C8 C 0.23957(10) 0.31239(2) 0.11077(8) 0.02505(14) Uani 1 1 d .
C9 C 0.42583(12) 0.28880(2) 0.06858(9) 0.02661(15) Uani 1 1 d .
H9 H 0.4014 0.2713 -0.0590 0.032 Uiso 1 1 calc R
C10 C 0.65292(10) 0.29280(2) 0.22931(9) 0.02686(16) Uani 1 1 d .
H10 H 0.7828 0.2773 0.2093 0.032 Uiso 1 1 calc R
C11 C 0.68717(11) 0.320023(19) 0.42093(8) 0.02541(14) Uani 1 1 d .
H11 H 0.8396 0.3225 0.5242 0.030 Uiso 1 1 calc R
N1 N 0.73408(9) 0.421860(17) 1.03989(8) 0.02547(14) Uani 1 1 d .
N2 N 0.43247(9) 0.46447(2) 1.25012(8) 0.02920(13) Uani 1 1 d .
N3 N 0.54231(8) 0.371139(19) 0.65540(7) 0.02460(13) Uani 1 1 d .
H3A H 0.6910 0.3746 0.7321 0.030 Uiso 1 1 calc R
O1 O 0.16385(8) 0.391508(16) 0.65059(7) 0.03261(12) Uani 1 1 d .
F1 F 0.01634(6) 0.309256(13) -0.04428(5) 0.03304(10) 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 0.0262(4) 0.0262(3) 0.0258(3) -0.0049(3) 0.0032(3) 0.0005(3)
C2 0.0328(5) 0.0261(4) 0.0249(4) -0.0054(3) 0.0089(3) -0.0015(3)
C3 0.0271(4) 0.0283(5) 0.0255(3) -0.0018(3) 0.0093(3) -0.0021(3)
C4 0.0271(3) 0.0211(3) 0.0210(3) 0.0015(2) 0.0086(3) -0.0006(3)
C5 0.0259(3) 0.0256(3) 0.0195(4) 0.0008(2) 0.0079(3) -0.0016(3)
C6 0.0269(3) 0.0210(3) 0.0180(3) 0.0002(3) 0.0064(3) -0.0021(3)
C7 0.0259(4) 0.0241(3) 0.0229(3) 0.0024(3) 0.0081(3) 0.0008(3)
C8 0.0253(4) 0.0272(4) 0.0185(3) 0.0029(3) 0.0034(3) -0.0041(3)
C9 0.0338(4) 0.0257(4) 0.0220(3) -0.0036(3) 0.0117(3) -0.0045(3)
C10 0.0271(4) 0.0291(4) 0.0273(3) -0.0012(3) 0.0131(3) 0.0000(3)
C11 0.0236(3) 0.0297(4) 0.0229(3) -0.0003(3) 0.0078(3) -0.0035(3)
N1 0.0269(3) 0.0259(3) 0.0240(3) -0.0033(2) 0.0062(3) 0.0005(2)
N2 0.0309(4) 0.0293(3) 0.0293(3) -0.0056(3) 0.0127(3) -0.0031(3)
N3 0.0229(3) 0.0282(3) 0.0206(3) -0.0033(2) 0.0046(2) -0.0006(2)
O1 0.0251(3) 0.0444(3) 0.0281(3) -0.0008(2) 0.0060(2) -0.0009(2)
F1 0.0266(2) 0.0448(2) 0.02214(17) -0.00635(18) 0.00112(17) -0.00209(17)
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'
F F 0.0171 0.0103 '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 122.47(5)
N1 C1 H1 118.5
C2 C1 H1 118.5
N2 C2 C1 122.04(6)
N2 C2 H2 119.1
C1 C2 H2 118.1
N2 C3 C4 122.36(6)
N2 C3 H3 118.5
C4 C3 H3 118.5
N1 C4 C3 121.90(6)
N1 C4 C5 119.00(6)
C3 C4 C5 119.10(7)
O1 C5 N3 125.31(5)
O1 C5 C4 120.11(6)
N3 C5 C4 114.58(6)
C7 C6 C11 119.60(5)
C7 C6 N3 123.21(6)
C11 C6 N3 117.20(5)
C6 C7 C8 117.77(6)
C6 C7 H7 121.1
C8 C7 H7 121.1
F1 C8 C9 117.97(5)
F1 C8 C7 117.68(5)
C9 C8 C7 124.35(5)
C8 C9 C10 116.88(5)
C8 C9 H9 121.8
C10 C9 H9 121.8
C9 C10 C11 121.04(6)
C9 C10 H10 119.5
C11 C10 H10 119.5
C10 C11 C6 120.40(5)
C10 C11 H11 119.5
C6 C11 H11 119.5
C4 N1 C1 115.52(5)
C2 N2 C3 115.68(6)
C5 N3 C6 127.80(5)
C5 N3 H3A 115.8
C6 N3 H3A 115.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3393(7)
C1 C2 1.3847(9)
C1 H1 0.9300
C2 N2 1.3310(9)
C2 H2 0.9300
C3 N2 1.3397(8)
C3 C4 1.3873(10)
C3 H3 0.9300
C4 N1 1.3363(9)
C4 C5 1.5043(8)
C5 O1 1.2224(9)
C5 N3 1.3523(9)
C6 C7 1.3939(9)
C6 C11 1.3966(9)
C6 N3 1.4153(7)
C7 C8 1.3867(7)
C7 H7 0.9300
C8 F1 1.3611(7)
C8 C9 1.3729(9)
C9 C10 1.3941(9)
C9 H9 0.9100
C10 C11 1.3880(7)
C10 H10 0.9300
C11 H11 0.9300
N3 H3A 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 -1.57(9)
N2 C3 C4 N1 -1.76(10)
N2 C3 C4 C5 178.74(5)
N1 C4 C5 O1 -177.33(6)
C3 C4 C5 O1 2.18(9)
N1 C4 C5 N3 3.26(8)
C3 C4 C5 N3 -177.23(6)
C11 C6 C7 C8 -0.49(9)
N3 C6 C7 C8 178.38(6)
C6 C7 C8 F1 -178.98(5)
C6 C7 C8 C9 0.54(9)
F1 C8 C9 C10 179.64(5)
C7 C8 C9 C10 0.12(10)
C8 C9 C10 C11 -0.84(10)
C9 C10 C11 C6 0.90(10)
C7 C6 C11 C10 -0.20(10)
N3 C6 C11 C10 -179.13(5)
C3 C4 N1 C1 1.46(8)
C5 C4 N1 C1 -179.04(6)
C2 C1 N1 C4 0.10(8)
C1 C2 N2 C3 1.28(8)
C4 C3 N2 C2 0.29(9)
O1 C5 N3 C6 0.30(11)
C4 C5 N3 C6 179.67(5)
C7 C6 N3 C5 8.36(10)
C11 C6 N3 C5 -172.84(5)
