#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/75/2237581.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237581
loop_
_publ_author_name
'Qu, Bao-Hua'
'Jia, Xiao-Chuan'
'Li, Jing'
'He, Ming-Yang'
_publ_section_title
;
 6,7-Difluoro-1,2,3,4-tetrahydroquinoxaline-5,8-dicarbonitrile
;
_journal_coeditor_code           YK2078
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o376
_journal_paper_doi               10.1107/S1600536813003206
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C10 H6 F2 N4'
_chemical_formula_sum            'C10 H6 F2 N4'
_chemical_formula_weight         220.19
_chemical_name_systematic
;
6,7-Difluoro-1,2,3,4-tetrahydroquinoxaline-5,8-dicarbonitrile
;
_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                75.545(2)
_cell_angle_beta                 81.854(2)
_cell_angle_gamma                76.427(2)
_cell_formula_units_Z            2
_cell_length_a                   5.2173(9)
_cell_length_b                   8.7011(15)
_cell_length_c                   11.1453(19)
_cell_measurement_reflns_used    2503
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.47
_cell_volume                     474.39(14)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4155
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0432
_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)+(0.0825P)²+0.0701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                1816
_reflns_number_total             2141
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yk2078.cif
_cod_data_source_block           I
_cod_original_cell_volume        474.40(14)
_cod_database_code               2237581
_cod_database_fobs_code          2237581
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.5584(3) 0.24423(15) 0.57193(12) 0.0414(3) Uani d . 1 1
C C2 -0.1573(3) -0.09578(15) 0.89446(12) 0.0403(3) Uani d . 1 1
C C3 0.3758(2) 0.16100(14) 0.65684(11) 0.0359(3) Uani d . 1 1
C C4 0.4178(2) -0.00938(14) 0.67660(11) 0.0382(3) Uani d . 1 1
C C5 0.2446(3) -0.09029(14) 0.75315(12) 0.0389(3) Uani d . 1 1
C C6 0.0223(2) -0.00551(14) 0.81451(11) 0.0359(3) Uani d . 1 1
C C7 -0.0247(2) 0.16328(14) 0.79859(11) 0.0348(3) Uani d . 1 1
C C8 0.1573(2) 0.24965(14) 0.71567(11) 0.0355(3) Uani d . 1 1
C C9 -0.2521(3) 0.41626(17) 0.85819(15) 0.0548(4) Uani d . 1 1
H H9A -0.1510 0.4206 0.9235 0.066 Uiso calc R 1 1
H H9B -0.4347 0.4681 0.8760 0.066 Uiso calc R 1 1
C C10 -0.1447(3) 0.50503(16) 0.73570(16) 0.0539(4) Uani d . 1 1
H H10A -0.2651 0.5195 0.6731 0.065 Uiso calc R 1 1
H H10B -0.1288 0.6115 0.7421 0.065 Uiso calc R 1 1
F F1 0.63601(16) -0.08862(10) 0.61981(8) 0.0525(3) Uani d . 1 1
F F2 0.28294(18) -0.25305(9) 0.77522(9) 0.0548(3) Uani d . 1 1
N N1 0.6992(3) 0.31503(17) 0.50478(13) 0.0574(4) Uani d . 1 1
N N2 -0.3029(3) -0.16595(16) 0.95803(12) 0.0560(3) Uani d . 1 1
N N3 0.1134(2) 0.41386(13) 0.69902(12) 0.0481(3) Uani d . 1 1
H H3 0.2066 0.4607 0.6368 0.058 Uiso d R 1 1
N N4 -0.2375(2) 0.24862(13) 0.85611(11) 0.0463(3) Uani d . 1 1
H H4 -0.3500 0.2005 0.9065 0.056 Uiso d R 1 1
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C3 177.89(14)
N2 C2 C6 179.11(14)
C8 C3 C4 121.41(11)
C8 C3 C1 119.68(11)
C4 C3 C1 118.89(11)
F1 C4 C5 121.20(11)
F1 C4 C3 118.67(11)
C5 C4 C3 120.12(11)
F2 C5 C4 121.21(11)
F2 C5 C6 118.54(11)
C4 C5 C6 120.23(11)
C7 C6 C5 121.40(11)
C7 C6 C2 120.11(11)
C5 C6 C2 118.48(11)
N4 C7 C6 122.84(11)
N4 C7 C8 118.78(11)
C6 C7 C8 118.36(11)
N3 C8 C3 122.59(11)
N3 C8 C7 118.94(11)
C3 C8 C7 118.45(11)
N4 C9 C10 110.40(12)
N4 C9 H9A 109.6
C10 C9 H9A 109.6
N4 C9 H9B 109.6
C10 C9 H9B 109.6
H9A C9 H9B 108.1
N3 C10 C9 109.85(12)
N3 C10 H10A 109.7
C9 C10 H10A 109.7
N3 C10 H10B 109.7
C9 C10 H10B 109.7
H10A C10 H10B 108.2
C8 N3 C10 120.46(11)
C8 N3 H3 114.4
C10 N3 H3 118.1
C7 N4 C9 121.10(11)
C7 N4 H4 121.1
C9 N4 H4 116.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.1425(17)
C1 C3 1.4330(17)
C2 N2 1.1408(17)
C2 C6 1.4310(17)
C3 C8 1.3973(17)
C3 C4 1.4116(17)
C4 F1 1.3481(14)
C4 C5 1.3492(18)
C5 F2 1.3465(14)
C5 C6 1.4081(18)
C6 C7 1.4007(16)
C7 N4 1.3580(16)
C7 C8 1.4354(16)
C8 N3 1.3618(16)
C9 N4 1.4485(18)
C9 C10 1.495(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 N3 1.4537(18)
C10 H10A 0.9700
C10 H10B 0.9700
N3 H3 0.8600
N4 H4 0.8599
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 N1 2_666 0.86 2.29 3.075(2) 152 yes
N4 H4 N2 2_457 0.86 2.21 3.0358(19) 160 yes
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
C8 C3 C4 F1 -178.24(11)
C1 C3 C4 F1 3.43(18)
C1 C3 C4 C5 -177.99(11)
F1 C4 C5 F2 -0.2(2)
C3 C4 C5 F2 -178.78(11)
F1 C4 C5 C6 178.02(11)
C3 C4 C5 C6 -0.5(2)
F2 C5 C6 C7 178.04(11)
C4 C5 C6 C7 -0.3(2)
F2 C5 C6 C2 -1.96(18)
C4 C5 C6 C2 179.72(11)
C5 C6 C7 N4 179.80(11)
C2 C6 C7 N4 -0.20(19)
C5 C6 C7 C8 1.22(19)
C2 C6 C7 C8 -178.78(10)
C4 C3 C8 N3 179.46(12)
C1 C3 C8 N3 -2.24(19)
C4 C3 C8 C7 0.62(19)
C1 C3 C8 C7 178.93(10)
N4 C7 C8 N3 1.12(19)
C6 C7 C8 N3 179.76(11)
N4 C7 C8 C3 180.00(11)
C6 C7 C8 C3 -1.37(18)
N4 C9 C10 N3 -50.23(18)
C3 C8 N3 C10 164.48(13)
C7 C8 N3 C10 -16.7(2)
C9 C10 N3 C8 41.7(2)
C6 C7 N4 C9 167.19(13)
C8 C7 N4 C9 -14.2(2)
C10 C9 N4 C7 39.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658366
