#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227401.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_2227401
loop_
_publ_author_name
'Ranganathan, Sathishkumar'
'Mahapatra, Sudarshan'
'Thakur, Tejender S.'
'Desiraju, Gautam R.'
_publ_section_title
;
 Quinoxaline: Z' = 1 form
;
_journal_coeditor_code           DS2061
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2789
_journal_paper_doi               10.1107/S1600536810039905
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H6 N2'
_chemical_formula_moiety         'C8 H6 N2'
_chemical_formula_sum            'C8 H6 N2'
_chemical_formula_weight         130.15
_chemical_melting_point_gt       301
_chemical_melting_point_lt       305
_chemical_name_common            Quinoxaline
_chemical_name_systematic
;
Quinoxaline
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0212(13)
_cell_length_b                   7.187(2)
_cell_length_c                   23.095(7)
_cell_measurement_reflns_used    734
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.8
_cell_volume                     667.5(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      270
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7556
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Pink
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0652P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                494
_reflns_number_total             956
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2061.cif
_cod_data_source_block           I
_cod_database_code               2227401
_cod_database_fobs_code          2227401
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.175(2) 0.0880(13) 0.1265(15) 0.0079(13) -0.0063(15) -0.0159(10)
N2 0.1395(18) 0.1161(14) 0.0837(11) -0.0085(13) -0.0069(11) -0.0063(9)
C3 0.156(3) 0.0884(14) 0.1418(19) 0.0102(16) 0.003(2) 0.0182(15)
C4 0.134(2) 0.1240(18) 0.1012(14) 0.002(2) -0.0040(16) 0.0271(14)
C5 0.131(2) 0.0819(13) 0.1025(14) 0.0005(13) 0.0090(14) -0.0123(10)
C6 0.1148(19) 0.0976(14) 0.1238(17) 0.0038(14) 0.0150(17) 0.0233(14)
C7 0.120(2) 0.154(2) 0.0862(13) -0.0023(19) -0.0026(14) 0.0241(16)
C8 0.160(2) 0.1223(17) 0.0806(13) 0.0018(19) -0.0101(16) -0.0157(12)
C9 0.1152(17) 0.0750(10) 0.0797(11) -0.0063(12) 0.0067(12) -0.0083(8)
C10 0.1008(16) 0.0802(10) 0.0717(10) -0.0131(12) 0.0090(10) -0.0034(8)
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.2099(7) 0.1700(3) 0.11405(9) 0.1298(9) Uani . . 1.000
N N2 0.2375(6) 0.4337(3) 0.20264(7) 0.1131(8) Uani . . 1.000
C C3 0.3379(8) 0.1356(3) 0.16499(13) 0.1287(13) Uani . . 1.000
C C4 0.3497(7) 0.2654(4) 0.20858(9) 0.1197(10) Uani . . 1.000
C C5 -0.0218(7) 0.6547(3) 0.13897(10) 0.1051(9) Uani . . 1.000
C C6 -0.1499(7) 0.6977(3) 0.08739(11) 0.1121(10) Uani . . 1.000
C C7 -0.1662(7) 0.5672(4) 0.04429(10) 0.1201(10) Uani . . 1.000
C C8 -0.0500(9) 0.3930(4) 0.05303(8) 0.1210(10) Uani . . 1.000
C C9 0.0873(6) 0.3450(2) 0.10587(8) 0.0900(8) Uani . . 1.000
C C10 0.1023(6) 0.4767(3) 0.14993(7) 0.0842(7) Uani . . 1.000
H H3 0.42490 0.01780 0.17200 0.1550 Uiso calc R 1.000
H H4 0.44230 0.23130 0.24390 0.1440 Uiso calc R 1.000
H H5 -0.01510 0.74440 0.16800 0.1260 Uiso calc R 1.000
H H6 -0.22890 0.81740 0.08070 0.1340 Uiso calc R 1.000
H H7 -0.25820 0.59880 0.00870 0.1440 Uiso calc R 1.000
H H8 -0.06220 0.30540 0.02350 0.1450 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C9 . . . 116.2(2) yes
C4 N2 C10 . . . 116.26(19) yes
N1 C3 C4 . . . 123.0(2) yes
N2 C4 C3 . . . 122.9(2) yes
C6 C5 C10 . . . 120.8(2) no
C5 C6 C7 . . . 120.6(2) no
C6 C7 C8 . . . 120.6(2) no
C7 C8 C9 . . . 120.1(2) no
N1 C9 C8 . . . 119.77(19) yes
N1 C9 C10 . . . 120.69(19) yes
C8 C9 C10 . . . 119.54(18) no
N2 C10 C5 . . . 120.67(19) yes
N2 C10 C9 . . . 121.0(2) yes
C5 C10 C9 . . . 118.38(18) no
N1 C3 H3 . . . 118.00 no
C4 C3 H3 . . . 119.00 no
N2 C4 H4 . . . 119.00 no
C3 C4 H4 . . . 119.00 no
C6 C5 H5 . . . 120.00 no
C10 C5 H5 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C7 C6 H6 . . . 120.00 no
C6 C7 H7 . . . 120.00 no
C8 C7 H7 . . . 120.00 no
C7 C8 H8 . . . 120.00 no
C9 C8 H8 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 . . 1.308(4) yes
N1 C9 . . 1.364(3) yes
N2 C4 . . 1.298(4) yes
N2 C10 . . 1.369(3) yes
C3 C4 . . 1.373(4) no
C5 C6 . . 1.334(4) no
C5 C10 . . 1.396(3) no
C6 C7 . . 1.369(4) no
C7 C8 . . 1.352(4) no
C8 C9 . . 1.383(3) no
C9 C10 . . 1.391(3) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 H7 . . 0.9300 no
C8 H8 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N1 N2 2.791(3) . . no
N2 N1 2.791(3) . . no
N2 H4 2.7900 . 4_655 no
C6 H7 3.0900 . 3_565 no
C8 H8 3.0700 . 3_455 no
C8 H8 3.0000 . 3_555 no
H4 N2 2.7900 . 4_645 no
H7 C6 3.0900 . 3_465 no
H8 C8 3.0000 . 3_455 no
H8 C8 3.0700 . 3_555 no
H8 H8 2.4200 . 3_455 no
H8 H8 2.4200 . 3_555 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C3 C4 . . . . 0.3(4) no
C3 N1 C9 C10 . . . . 0.3(4) no
C3 N1 C9 C8 . . . . 179.5(3) no
C10 N2 C4 C3 . . . . 0.3(4) no
C4 N2 C10 C5 . . . . -179.3(2) no
C4 N2 C10 C9 . . . . 0.3(4) no
N1 C3 C4 N2 . . . . -0.7(5) no
C6 C5 C10 C9 . . . . -0.4(4) no
C6 C5 C10 N2 . . . . 179.2(3) no
C10 C5 C6 C7 . . . . 0.8(4) no
C5 C6 C7 C8 . . . . -0.6(4) no
C6 C7 C8 C9 . . . . -0.1(5) no
C7 C8 C9 C10 . . . . 0.5(4) no
C7 C8 C9 N1 . . . . -178.8(3) no
N1 C9 C10 N2 . . . . -0.6(4) no
C8 C9 C10 C5 . . . . -0.3(4) no
N1 C9 C10 C5 . . . . 179.0(2) no
C8 C9 C10 N2 . . . . -179.8(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21106470
