#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029603.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_4029603
loop_
_publ_author_name
'Li, Chao'
'Zhang, Wen-Ting'
'Wang, Xiang-Shan'
_publ_section_title
;
 CuI-Catalyzed C-N Bond Formation and Cleavage for the Synthesis of
 Benzimidazo[1,2-a]quinazoline Derivatives.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5847
_journal_page_last               5851
_journal_paper_doi               10.1021/jo5007398
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C14 H9 N3'
_chemical_formula_weight         219.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                90.00
_cell_formula_units_Z            16
_cell_length_a                   10.7584(3)
_cell_length_b                   41.2284(11)
_cell_length_c                   9.1427(2)
_cell_measurement_reflns_used    5563
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.56
_cell_measurement_theta_min      2.97
_cell_volume                     4055.26(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11670
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1822
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0273
_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)+(0.0377P)²+1.1567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                1683
_reflns_number_total             1822
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5007398_si_002.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029603.cif.
;
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               4029603
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'
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 0.28666(13) 0.07557(3) 0.09274(15) 0.0386(3) Uani 1 1 d .
C2 C 0.36722(13) 0.06773(3) -0.02117(16) 0.0437(3) Uani 1 1 d .
H2A H 0.4094 0.0837 -0.0732 0.052 Uiso 1 1 calc R
C3 C 0.38163(15) 0.03540(3) -0.05323(17) 0.0512(4) Uani 1 1 d .
H3A H 0.4351 0.0294 -0.1284 0.061 Uiso 1 1 calc R
C4 C 0.31819(16) 0.01119(4) 0.02395(19) 0.0576(4) Uani 1 1 d .
H4A H 0.3278 -0.0104 -0.0031 0.069 Uiso 1 1 calc R
C5 C 0.24242(15) 0.01892(4) 0.13840(19) 0.0577(4) Uani 1 1 d .
H5A H 0.2019 0.0027 0.1908 0.069 Uiso 1 1 calc R
C6 C 0.22660(13) 0.05146(4) 0.17557(16) 0.0466(4) Uani 1 1 d .
C7 C 0.17553(14) 0.09632(4) 0.27590(16) 0.0469(3) Uani 1 1 d .
C8 C 0.15014(15) 0.14900(4) 0.33686(17) 0.0570(4) Uani 1 1 d .
H8A H 0.1188 0.1647 0.4001 0.068 Uiso 1 1 calc R
C9 C 0.22043(12) 0.16011(4) 0.21450(16) 0.0459(3) Uani 1 1 d .
C10 C 0.23729(15) 0.19331(4) 0.18310(19) 0.0559(4) Uani 1 1 d .
H10A H 0.2046 0.2089 0.2459 0.067 Uiso 1 1 calc R
C11 C 0.30116(15) 0.20282(4) 0.0615(2) 0.0571(4) Uani 1 1 d .
H11A H 0.3130 0.2247 0.0420 0.069 Uiso 1 1 calc R
C12 C 0.34816(14) 0.17957(4) -0.0326(2) 0.0535(4) Uani 1 1 d .
H12A H 0.3894 0.1862 -0.1169 0.064 Uiso 1 1 calc R
C13 C 0.33557(12) 0.14704(3) -0.00515(16) 0.0449(3) Uani 1 1 d .
H13A H 0.3691 0.1318 -0.0690 0.054 Uiso 1 1 calc R
C14 C 0.27200(11) 0.13712(3) 0.11952(15) 0.0376(3) Uani 1 1 d .
N1 N 0.12626(12) 0.11915(4) 0.36751(16) 0.0572(4) Uani 1 1 d .
N2 N 0.15853(12) 0.06484(3) 0.28884(15) 0.0542(3) Uani 1 1 d .
N3 N 0.25146(11) 0.10475(3) 0.15701(11) 0.0392(3) Uani 1 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 C1 C2 133.29(12)
N3 C1 C6 104.99(12)
C2 C1 C6 121.62(13)
C3 C2 C1 117.06(13)
C3 C2 H2A 121.5
C1 C2 H2A 121.5
C2 C3 C4 121.95(15)
C2 C3 H3A 119.0
C4 C3 H3A 119.0
C5 C4 C3 120.77(15)
C5 C4 H4A 119.6
C3 C4 H4A 119.6
C4 C5 C6 118.98(14)
C4 C5 H5A 120.5
C6 C5 H5A 120.5
N2 C6 C5 129.11(14)
N2 C6 C1 111.37(13)
C5 C6 C1 119.51(14)
N2 C7 N1 124.75(14)
N2 C7 N3 113.25(13)
N1 C7 N3 122.00(13)
N1 C8 C9 125.69(15)
N1 C8 H8A 117.2
C9 C8 H8A 117.2
C14 C9 C10 118.67(14)
C14 C9 C8 118.64(13)
C10 C9 C8 122.67(14)
C11 C10 C9 120.64(15)
C11 C10 H10A 119.7
C9 C10 H10A 119.7
C10 C11 C12 119.43(15)
C10 C11 H11A 120.3
C12 C11 H11A 120.3
C13 C12 C11 121.84(16)
C13 C12 H12A 119.1
C11 C12 H12A 119.1
C12 C13 C14 119.11(14)
C12 C13 H13A 120.4
C14 C13 H13A 120.4
C13 C14 N3 124.08(12)
C13 C14 C9 120.27(12)
N3 C14 C9 115.61(12)
C8 N1 C7 116.56(14)
C7 N2 C6 104.63(12)
C1 N3 C14 132.85(11)
C1 N3 C7 105.74(11)
C14 N3 C7 121.28(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.3915(17)
C1 C2 1.393(2)
C1 C6 1.407(2)
C2 C3 1.3736(19)
C2 H2A 0.9300
C3 C4 1.400(2)
C3 H3A 0.9300
C4 C5 1.364(2)
C4 H4A 0.9300
C5 C6 1.394(2)
C5 H5A 0.9300
C6 N2 1.383(2)
C7 N2 1.316(2)
C7 N1 1.367(2)
C7 N3 1.4034(18)
C8 N1 1.288(2)
C8 C9 1.426(2)
C8 H8A 0.9300
C9 C14 1.4001(19)
C9 C10 1.410(2)
C10 C11 1.365(2)
C10 H10A 0.9300
C11 C12 1.384(2)
C11 H11A 0.9300
C12 C13 1.3712(19)
C12 H12A 0.9300
C13 C14 1.3907(19)
C13 H13A 0.9300
C14 N3 1.3954(17)
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
N3 C1 C2 C3 178.40(14)
C6 C1 C2 C3 2.6(2)
C1 C2 C3 C4 0.3(2)
C2 C3 C4 C5 -2.4(2)
C3 C4 C5 C6 1.5(2)
C4 C5 C6 N2 -177.65(15)
C4 C5 C6 C1 1.4(2)
N3 C1 C6 N2 -1.15(16)
C2 C1 C6 N2 175.68(12)
N3 C1 C6 C5 179.68(13)
C2 C1 C6 C5 -3.5(2)
N1 C8 C9 C14 -1.8(2)
N1 C8 C9 C10 176.43(15)
C14 C9 C10 C11 0.9(2)
C8 C9 C10 C11 -177.37(14)
C9 C10 C11 C12 0.9(2)
C10 C11 C12 C13 -1.9(3)
C11 C12 C13 C14 1.1(2)
C12 C13 C14 N3 178.72(13)
C12 C13 C14 C9 0.74(19)
C10 C9 C14 C13 -1.70(19)
C8 C9 C14 C13 176.62(13)
C10 C9 C14 N3 -179.84(12)
C8 C9 C14 N3 -1.53(17)
C9 C8 N1 C7 1.6(2)
N2 C7 N1 C8 -178.51(15)
N3 C7 N1 C8 1.9(2)
N1 C7 N2 C6 -178.93(14)
N3 C7 N2 C6 0.68(16)
C5 C6 N2 C7 179.38(15)
C1 C6 N2 C7 0.31(16)
C2 C1 N3 C14 9.3(3)
C6 C1 N3 C14 -174.39(13)
C2 C1 N3 C7 -174.83(15)
C6 C1 N3 C7 1.46(14)
C13 C14 N3 C1 2.1(2)
C9 C14 N3 C1 -179.81(13)
C13 C14 N3 C7 -173.20(13)
C9 C14 N3 C7 4.86(17)
N2 C7 N3 C1 -1.41(16)
N1 C7 N3 C1 178.22(13)
N2 C7 N3 C14 175.03(12)
N1 C7 N3 C14 -5.3(2)
