#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/21/8102158.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_8102158
loop_
_publ_author_name
'Li, Jie'
'Xue, Dong'
'Zhang, Zun-Ting'
_publ_section_title
;
Crystal structure of 3-amino-5-(furan-2-yl)-2-nitrobiphenyl-4-carbonitrile, 
C₁₇H₁₁N₃O₃
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              297
_journal_page_last               298
_journal_volume                  222
_journal_year                    2007
_chemical_formula_moiety         'C17 H11 N3 O3'
_chemical_formula_sum            'C17 H11 N3 O3'
_chemical_formula_weight         305.29
_chemical_melting_point          435
_chemical_name_systematic
; 
3-amino-5-(furan-2-yl)-2-nitrobiphenyl-4-carbonitrile 
;
_space_group_IT_number           148
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   36.6123(16)
_cell_length_b                   36.6123(16)
_cell_length_c                   5.5797(3)
_cell_measurement_reflns_used    2568
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      1.93
_cell_volume                     6477.3(5)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       phi/omega
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11180
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs (Bruker,1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2844
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00064(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0416
_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)+(0.0650P)²+2.9499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                1626
_reflns_number_total             2568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2053.cff
_cod_data_source_block           xb0960
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               8102158
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C17 C 0.30307(7) 0.19711(7) -0.1338(4) 0.0568(6) Uani 1 18 f d . . .
N2 N 0.28665(7) 0.12224(7) 0.0589(4) 0.0588(5) Uani 1 18 f d . . .
N3 N 0.22808(5) 0.08323(6) 0.4411(4) 0.0568(5) Uani 1 18 f d . . .
O1 O 0.27713(6) 0.25575(6) -0.1539(3) 0.0676(5) Uani 1 18 f d . . .
O2 O 0.23102(6) 0.05680(5) 0.3212(3) 0.0809(6) Uani 1 18 f d . . .
O3 O 0.22089(6) 0.07901(6) 0.6565(3) 0.0787(5) Uani 1 18 f d . . .
C1 C 0.27922(8) 0.29408(7) -0.1796(5) 0.0708(7) Uani 1 18 f d . . .
H1 H 0.2902 0.3115 -0.3128 0.085 Uiso 1 18 f calc R . .
C2 C 0.26365(7) 0.30260(7) 0.0098(5) 0.0694(7) Uani 1 18 f d . . .
H2 H 0.2618 0.3267 0.0352 0.083 Uiso 1 18 f calc R . .
C3 C 0.25016(7) 0.26810(7) 0.1681(4) 0.0553(6) Uani 1 18 f d . . .
H3 H 0.2377 0.2652 0.3173 0.066 Uiso 1 18 f calc R . .
C4 C 0.25874(5) 0.24044(5) 0.0627(3) 0.0472(5) Uani 1 18 f d . . .
C5 C 0.25150(6) 0.19968(6) 0.1459(3) 0.0437(5) Uani 1 18 f d . . .
C6 C 0.22045(6) 0.17907(6) 0.3214(3) 0.0464(5) Uani 1 18 f d . . .
H6 H 0.2061 0.1921 0.3808 0.056 Uiso 1 18 f calc R . .
C7 C 0.21069(6) 0.13992(6) 0.4083(3) 0.0453(5) Uani 1 18 f d . . .
C8 C 0.23387(6) 0.12134(6) 0.3256(3) 0.0462(5) Uani 1 18 f d . . .
C9 C 0.26415(6) 0.13967(6) 0.1425(3) 0.0461(5) Uani 1 18 f d . . .
C10 C 0.27240(6) 0.17950(6) 0.0550(3) 0.0453(5) Uani 1 18 f d . . .
C11 C 0.17325(6) 0.11774(6) 0.5687(3) 0.0461(5) Uani 1 18 f d . . .
C12 C 0.16806(7) 0.13845(7) 0.7613(3) 0.0524(5) Uani 1 18 f d . . .
H12 H 0.1885 0.1662 0.7942 0.063 Uiso 1 18 f calc R . .
C13 C 0.13270(8) 0.11827(8) 0.9055(4) 0.0632(6) Uani 1 18 f d . . .
H13 H 0.1297 0.1323 1.0361 0.076 Uiso 1 18 f calc R . .
C14 C 0.10229(8) 0.07787(8) 0.8564(4) 0.0666(7) Uani 1 18 f d . . .
H14 H 0.0786 0.0644 0.9537 0.080 Uiso 1 18 f calc R . .
C15 C 0.10655(7) 0.05698(7) 0.6639(4) 0.0631(6) Uani 1 18 f d . . .
H15 H 0.0856 0.0295 0.6307 0.076 Uiso 1 18 f calc R . .
C16 C 0.14186(7) 0.07668(7) 0.5189(4) 0.0530(6) Uani 1 18 f d . . .
H16 H 0.1446 0.0624 0.3883 0.064 Uiso 1 18 f calc R . .
N1 N 0.32697(8) 0.20786(7) -0.2847(4) 0.0835(7) Uani 1 18 f d . . .
H2A H 0.3020(7) 0.1329(7) -0.072(4) 0.066(7) Uiso 1 18 f d . . .
H2B H 0.2772(8) 0.0951(9) 0.092(4) 0.077(8) Uiso 1 18 f 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C17 C10 174.4(2) . . ?
C9 N2 H2A 118.7(15) . . ?
C9 N2 H2B 117.8(16) . . ?
H2A N2 H2B 118(2) . . ?
O3 N3 O2 122.36(19) . . ?
O3 N3 C8 118.41(18) . . ?
O2 N3 C8 119.23(19) . . ?
C4 O1 C1 106.06(18) . . ?
C2 C1 O1 110.5(2) . . ?
C2 C1 H1 124.7 . . ?
O1 C1 H1 124.7 . . ?
C1 C2 C3 106.9(2) . . ?
C1 C2 H2 126.6 . . ?
C3 C2 H2 126.6 . . ?
C4 C3 C2 107.0(2) . . ?
C4 C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
C3 C4 O1 109.51(19) . . ?
C3 C4 C5 130.18(19) . . ?
O1 C4 C5 120.31(18) . . ?
C10 C5 C6 118.70(18) . . ?
C10 C5 C4 124.01(18) . . ?
C6 C5 C4 117.25(18) . . ?
C7 C6 C5 121.58(18) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 118.83(18) . . ?
C6 C7 C11 117.80(18) . . ?
C8 C7 C11 123.12(17) . . ?
C7 C8 C9 122.02(18) . . ?
C7 C8 N3 119.08(17) . . ?
C9 C8 N3 118.82(18) . . ?
N2 C9 C8 123.1(2) . . ?
N2 C9 C10 119.95(19) . . ?
C8 C9 C10 116.86(17) . . ?
C5 C10 C9 121.78(17) . . ?
C5 C10 C17 122.72(19) . . ?
C9 C10 C17 115.49(18) . . ?
C12 C11 C16 118.86(19) . . ?
C12 C11 C7 120.58(18) . . ?
C16 C11 C7 120.46(17) . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.9(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C17 N1 1.134(3) . ?
C17 C10 1.436(3) . ?
N2 C9 1.352(3) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.89(3) . ?
N3 O3 1.223(2) . ?
N3 O2 1.225(2) . ?
N3 C8 1.453(3) . ?
O1 C4 1.360(3) . ?
O1 C1 1.374(3) . ?
C1 C2 1.310(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.413(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.337(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.455(3) . ?
C5 C10 1.398(3) . ?
C5 C6 1.401(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.405(3) . ?
C7 C11 1.492(3) . ?
C8 C9 1.407(3) . ?
C9 C10 1.420(3) . ?
C11 C12 1.382(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 C2 0.8(3) . . . . ?
O1 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 O1 0.2(2) . . . . ?
C2 C3 C4 C5 179.9(2) . . . . ?
C1 O1 C4 C3 -0.6(2) . . . . ?
C1 O1 C4 C5 179.67(18) . . . . ?
C3 C4 C5 C10 -160.5(2) . . . . ?
O1 C4 C5 C10 19.2(3) . . . . ?
C3 C4 C5 C6 22.1(3) . . . . ?
O1 C4 C5 C6 -158.26(18) . . . . ?
C10 C5 C6 C7 1.1(3) . . . . ?
C4 C5 C6 C7 178.69(18) . . . . ?
C5 C6 C7 C8 2.9(3) . . . . ?
C5 C6 C7 C11 -171.57(17) . . . . ?
C6 C7 C8 C9 -5.6(3) . . . . ?
C11 C7 C8 C9 168.52(18) . . . . ?
C6 C7 C8 N3 171.07(17) . . . . ?
C11 C7 C8 N3 -14.8(3) . . . . ?
O3 N3 C8 C7 -34.1(3) . . . . ?
O2 N3 C8 C7 146.7(2) . . . . ?
O3 N3 C8 C9 142.7(2) . . . . ?
O2 N3 C8 C9 -36.5(3) . . . . ?
C7 C8 C9 N2 -179.53(19) . . . . ?
N3 C8 C9 N2 3.8(3) . . . . ?
C7 C8 C9 C10 4.1(3) . . . . ?
N3 C8 C9 C10 -172.54(17) . . . . ?
C6 C5 C10 C9 -2.5(3) . . . . ?
C4 C5 C10 C9 -179.96(18) . . . . ?
C6 C5 C10 C17 176.65(18) . . . . ?
C4 C5 C10 C17 -0.8(3) . . . . ?
N2 C9 C10 C5 -176.47(19) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
N2 C9 C10 C17 4.3(3) . . . . ?
C8 C9 C10 C17 -179.26(18) . . . . ?
N1 C17 C10 C5 -166(3) . . . . ?
N1 C17 C10 C9 14(3) . . . . ?
C6 C7 C11 C12 -49.1(3) . . . . ?
C8 C7 C11 C12 136.7(2) . . . . ?
C6 C7 C11 C16 127.3(2) . . . . ?
C8 C7 C11 C16 -46.9(3) . . . . ?
C16 C11 C12 C13 1.6(3) . . . . ?
C7 C11 C12 C13 178.0(2) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
C7 C11 C16 C15 -177.61(19) . . . . ?
