#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:34:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178485 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/06/4030653.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_4030653
loop_
_publ_author_name
'Iaroshenko, Viktor O.'
'Gevorgyan, Ashot'
'Mkrtchyan, Satenik'
'Arakelyan, Knar'
'Grigoryan, Tatevik'
'Yedoyan, Julietta'
'Villinger, Alexander'
'Langer, Peter'
_publ_section_title
;
 Transition-metal-catalyzed arylation of nitroimidazoles and further
 transformations of manipulable nitro group.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2103
_journal_page_last               2119
_journal_paper_doi               10.1021/jo5025927
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C18 H14 N4 O2'
_chemical_formula_sum            'C18 H14 N4 O2'
_chemical_formula_weight         318.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                90.00
_cell_angle_beta                 100.198(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4755(4)
_cell_length_b                   14.1633(6)
_cell_length_c                   10.9706(4)
_cell_measurement_reflns_used    3680
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      60.308
_cell_measurement_theta_min      4.887
_cell_volume                     1601.97(11)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10868
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0363
_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)+(0.0445P)²+0.3668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                3114
_reflns_number_total             3671
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            7a-is_sm652_1.cif
_cod_data_source_block           is_sm652_1
_cod_depositor_comments
'Adding full bibliography for 4030648--4030655.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4030653
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
N1 N 0.29990(11) 0.11385(9) 0.84198(13) 0.0222(3) Uani 1 1 d .
N2 N 0.28663(12) 0.26620(9) 0.79022(13) 0.0236(3) Uani 1 1 d .
N3 N 0.50831(12) 0.31523(9) 0.86218(13) 0.0250(3) Uani 1 1 d .
N4 N 0.93893(17) -0.12656(14) 1.12431(18) 0.0492(5) Uani 1 1 d .
O1 O 0.47694(12) 0.39474(8) 0.82344(13) 0.0352(3) Uani 1 1 d .
O2 O 0.61883(11) 0.29329(8) 0.91174(14) 0.0370(3) Uani 1 1 d .
C1 C 0.42273(13) 0.15036(10) 0.88272(14) 0.0190(3) Uani 1 1 d .
C2 C 0.40929(13) 0.24400(10) 0.84842(15) 0.0203(3) Uani 1 1 d .
C3 C 0.22348(14) 0.18644(11) 0.78909(15) 0.0250(3) Uani 1 1 d .
H3 H 0.1340 0.1797 0.7551 0.030 Uiso 1 1 calc R
C4 C 0.24773(15) 0.02346(10) 0.87821(17) 0.0283(3) Uani 1 1 d .
H4A H 0.3112 -0.0275 0.8729 0.034 Uiso 1 1 calc R
H4B H 0.1669 0.0081 0.8201 0.034 Uiso 1 1 calc R
C5 C 0.21949(18) 0.02835(12) 1.01016(19) 0.0348(4) Uani 1 1 d .
H5A H 0.1767 -0.0310 1.0287 0.042 Uiso 1 1 calc R
H5B H 0.3025 0.0336 1.0691 0.042 Uiso 1 1 calc R
C6 C 0.13361(19) 0.11104(13) 1.02911(19) 0.0358(4) Uani 1 1 d .
C7 C 0.1818(2) 0.18598(15) 1.1050(2) 0.0477(5) Uani 1 1 d .
H7 H 0.2683 0.1842 1.1493 0.057 Uiso 1 1 calc R
C8 C 0.1032(3) 0.26416(16) 1.1163(3) 0.0629(8) Uani 1 1 d .
H8 H 0.1365 0.3152 1.1686 0.075 Uiso 1 1 calc R
C9 C -0.0223(3) 0.26754(18) 1.0519(3) 0.0656(8) Uani 1 1 d .
H9 H -0.0753 0.3208 1.0599 0.079 Uiso 1 1 calc R
C10 C -0.0706(2) 0.19367(17) 0.9760(3) 0.0588(7) Uani 1 1 d .
H10 H -0.1569 0.1960 0.9311 0.071 Uiso 1 1 calc R
C11 C 0.0071(2) 0.11566(15) 0.9653(2) 0.0448(5) Uani 1 1 d .
H11 H -0.0271 0.0646 0.9134 0.054 Uiso 1 1 calc R
C12 C 0.53288(13) 0.09080(10) 0.93760(14) 0.0193(3) Uani 1 1 d .
C13 C 0.60786(14) 0.11249(10) 1.05183(15) 0.0234(3) Uani 1 1 d .
H13 H 0.5864 0.1657 1.0969 0.028 Uiso 1 1 calc R
C14 C 0.71380(14) 0.05697(12) 1.10060(15) 0.0260(3) Uani 1 1 d .
H14 H 0.7656 0.0723 1.1782 0.031 Uiso 1 1 calc R
C15 C 0.74301(13) -0.02136(11) 1.03445(15) 0.0241(3) Uani 1 1 d .
C16 C 0.66858(15) -0.04482(11) 0.91999(15) 0.0269(3) Uani 1 1 d .
H16 H 0.6891 -0.0989 0.8759 0.032 Uiso 1 1 calc R
C17 C 0.56421(15) 0.01216(10) 0.87173(16) 0.0250(3) Uani 1 1 d .
H17 H 0.5136 -0.0023 0.7933 0.030 Uiso 1 1 calc R
C18 C 0.85272(16) -0.08027(13) 1.08506(18) 0.0322(4) 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'
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
C3 N1 C1 107.27(12)
C3 N1 C4 123.38(12)
C1 N1 C4 127.21(13)
C3 N2 C2 103.75(11)
O1 N3 O2 123.97(13)
O1 N3 C2 117.65(12)
O2 N3 C2 118.39(12)
C2 C1 N1 103.11(12)
C2 C1 C12 134.32(13)
N1 C1 C12 122.34(12)
N2 C2 C1 113.02(12)
N2 C2 N3 119.31(12)
C1 C2 N3 127.61(12)
N2 C3 N1 112.84(13)
N2 C3 H3 123.6
N1 C3 H3 123.6
N1 C4 C5 111.04(13)
N1 C4 H4A 109.4
C5 C4 H4A 109.4
N1 C4 H4B 109.4
C5 C4 H4B 109.4
H4A C4 H4B 108.0
C6 C5 C4 112.61(15)
C6 C5 H5A 109.1
C4 C5 H5A 109.1
C6 C5 H5B 109.1
C4 C5 H5B 109.1
H5A C5 H5B 107.8
C11 C6 C7 118.7(2)
C11 C6 C5 120.36(18)
C7 C6 C5 120.82(19)
C6 C7 C8 120.1(3)
C6 C7 H7 119.9
C8 C7 H7 119.9
C9 C8 C7 120.3(3)
C9 C8 H8 119.8
C7 C8 H8 119.8
C10 C9 C8 119.9(2)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 119.8(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
C6 C11 C10 121.1(2)
C6 C11 H11 119.4
C10 C11 H11 119.4
C13 C12 C17 119.67(13)
C13 C12 C1 121.32(13)
C17 C12 C1 118.99(13)
C14 C13 C12 120.53(14)
C14 C13 H13 119.7
C12 C13 H13 119.7
C13 C14 C15 119.09(14)
C13 C14 H14 120.5
C15 C14 H14 120.5
C14 C15 C16 121.36(13)
C14 C15 C18 119.53(15)
C16 C15 C18 119.11(15)
C17 C16 C15 118.83(14)
C17 C16 H16 120.6
C15 C16 H16 120.6
C16 C17 C12 120.52(15)
C16 C17 H17 119.7
C12 C17 H17 119.7
N4 C18 C15 179.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.3675(19)
N1 C1 1.3853(18)
N1 C4 1.4739(19)
N2 C3 1.3082(19)
N2 C2 1.3665(18)
N3 O1 1.2277(16)
N3 O2 1.2287(17)
N3 C2 1.4357(18)
N4 C18 1.137(2)
C1 C2 1.379(2)
C1 C12 1.4695(19)
C3 H3 0.9500
C4 C5 1.530(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.513(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C11 1.387(3)
C6 C7 1.388(3)
C7 C8 1.398(4)
C7 H7 0.9500
C8 C9 1.379(4)
C8 H8 0.9500
C9 C10 1.377(4)
C9 H9 0.9500
C10 C11 1.390(3)
C10 H10 0.9500
C11 H11 0.9500
C12 C13 1.390(2)
C12 C17 1.398(2)
C13 C14 1.388(2)
C13 H13 0.9500
C14 C15 1.389(2)
C14 H14 0.9500
C15 C16 1.396(2)
C15 C18 1.449(2)
C16 C17 1.386(2)
C16 H16 0.9500
C17 H17 0.9500
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
C3 N1 C1 C2 -0.72(17)
C4 N1 C1 C2 -164.36(15)
C3 N1 C1 C12 -176.02(14)
C4 N1 C1 C12 20.3(2)
C3 N2 C2 C1 0.43(19)
C3 N2 C2 N3 177.62(14)
N1 C1 C2 N2 0.19(18)
C12 C1 C2 N2 174.64(16)
N1 C1 C2 N3 -176.72(14)
C12 C1 C2 N3 -2.3(3)
O1 N3 C2 N2 2.0(2)
O2 N3 C2 N2 -178.04(15)
O1 N3 C2 C1 178.72(16)
O2 N3 C2 C1 -1.3(2)
C2 N2 C3 N1 -0.91(19)
C1 N1 C3 N2 1.08(19)
C4 N1 C3 N2 165.50(15)
C3 N1 C4 C5 -88.03(19)
C1 N1 C4 C5 73.2(2)
N1 C4 C5 C6 53.28(19)
C4 C5 C6 C11 64.6(2)
C4 C5 C6 C7 -111.8(2)
C11 C6 C7 C8 0.1(3)
C5 C6 C7 C8 176.55(19)
C6 C7 C8 C9 -0.2(3)
C7 C8 C9 C10 -0.1(4)
C8 C9 C10 C11 0.5(4)
C7 C6 C11 C10 0.3(3)
C5 C6 C11 C10 -176.15(19)
C9 C10 C11 C6 -0.6(3)
C2 C1 C12 C13 58.9(2)
N1 C1 C12 C13 -127.49(16)
C2 C1 C12 C17 -119.54(19)
N1 C1 C12 C17 54.1(2)
C17 C12 C13 C14 0.3(2)
C1 C12 C13 C14 -178.13(14)
C12 C13 C14 C15 -0.8(2)
C13 C14 C15 C16 0.4(2)
C13 C14 C15 C18 -179.45(15)
C14 C15 C16 C17 0.5(2)
C18 C15 C16 C17 -179.61(16)
C15 C16 C17 C12 -1.1(2)
C13 C12 C17 C16 0.6(2)
C1 C12 C17 C16 179.12(15)
C14 C15 C18 N4 -143(100)
C16 C15 C18 N4 37(46)
