#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/01/2220165.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_2220165
loop_
_publ_author_name
'Yang, Feng-Ling'
'Li, Gong-Chun'
'Yao, Chang-Sheng'
_publ_section_title
;Ethyl
 4-(4-nitrophenyl)-2-(trifluoromethyl)pyrimido[1,2-a]benzimidazole-3-carboxylate
;
_journal_coeditor_code           FJ2169
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2469
_journal_paper_doi               10.1107/S160053680803941X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C20 H13 F3 N4 O4'
_chemical_formula_moiety         'C20 H13 F3 N4 O4'
_chemical_formula_sum            'C20 H13 F3 N4 O4'
_chemical_formula_weight         430.34
_chemical_name_systematic
;Ethyl
 4-(4-nitrophenyl)-2-(trifluoromethyl)pyrimido[1,2-a]benzimidazole-
3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 111.027(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4075(5)
_cell_length_b                   26.6904(14)
_cell_length_c                   9.0559(5)
_cell_measurement_reflns_used    4213
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.3
_cell_volume                     1896.82(19)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2002)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2002)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18499
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.9606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2002)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.224
_refine_ls_extinction_coef       0.0129(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0565P)²+0.3435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                3911
_reflns_number_total             4492
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2169.cif
_cod_data_source_block           I
_cod_original_cell_volume        1896.82(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220165
_cod_database_fobs_code          2220165
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
F F1 0.84705(13) 0.60521(4) 0.95949(11) 0.0426(3) Uani d . 1
F F2 0.69893(13) 0.67273(4) 0.89880(11) 0.0385(3) Uani d . 1
F F3 0.89019(12) 0.65773(4) 0.79846(11) 0.0409(3) Uani d . 1
O O1 0.62940(15) 0.71967(4) 0.55129(14) 0.0356(3) Uani d . 1
O O2 0.75651(13) 0.66746(4) 0.43224(12) 0.0274(2) Uani d . 1
O O3 0.21549(16) 0.71512(4) -0.24329(13) 0.0346(3) Uani d . 1
O O4 0.26759(14) 0.64080(4) -0.30905(12) 0.0308(3) Uani d . 1
N N1 0.57725(14) 0.56861(4) 0.74106(13) 0.0219(3) Uani d . 1
N N2 0.37814(14) 0.56650(4) 0.47093(13) 0.0189(2) Uani d . 1
N N3 0.37200(15) 0.50437(4) 0.64198(13) 0.0229(3) Uani d . 1
N N4 0.26160(15) 0.67171(4) -0.21060(14) 0.0223(3) Uani d . 1
C C1 0.44825(17) 0.54571(5) 0.62568(15) 0.0202(3) Uani d . 1
C C2 0.45006(17) 0.60793(5) 0.43043(15) 0.0191(3) Uani d . 1
C C3 0.57796(17) 0.63165(5) 0.54926(16) 0.0209(3) Uani d . 1
C C4 0.63487(17) 0.61029(5) 0.70372(15) 0.0215(3) Uani d . 1
C C5 0.24130(17) 0.53536(5) 0.38824(16) 0.0204(3) Uani d . 1
C C6 0.24395(18) 0.49711(5) 0.49625(17) 0.0220(3) Uani d . 1
C C7 0.12231(19) 0.45881(5) 0.45180(18) 0.0266(3) Uani d . 1
H H7 0.1244 0.4322 0.5222 0.032 Uiso calc R 1
C C8 -0.00046(19) 0.46102(6) 0.30259(18) 0.0293(3) Uani d . 1
H H8 -0.0837 0.4353 0.2694 0.035 Uiso calc R 1
C C9 -0.0057(2) 0.50043(6) 0.19808(18) 0.0293(3) Uani d . 1
H H9 -0.0946 0.5011 0.0973 0.035 Uiso calc R 1
C C10 0.11445(18) 0.53821(6) 0.23755(16) 0.0255(3) Uani d . 1
H H10 0.1112 0.5647 0.1664 0.031 Uiso calc R 1
C C11 0.39418(17) 0.62415(5) 0.26248(15) 0.0200(3) Uani d . 1
C C12 0.41635(18) 0.59172(5) 0.15022(16) 0.0223(3) Uani d . 1
H H12 0.4605 0.5590 0.1804 0.027 Uiso calc R 1
C C13 0.37390(18) 0.60735(5) -0.00523(16) 0.0218(3) Uani d . 1
H H13 0.3883 0.5857 -0.0828 0.026 Uiso calc R 1
C C14 0.30986(17) 0.65537(5) -0.04460(15) 0.0204(3) Uani d . 1
C C15 0.28857(18) 0.68848(5) 0.06432(16) 0.0235(3) Uani d . 1
H H15 0.2457 0.7213 0.0337 0.028 Uiso calc R 1
C C16 0.33160(18) 0.67247(5) 0.21975(16) 0.0226(3) Uani d . 1
H H16 0.3184 0.6945 0.2970 0.027 Uiso calc R 1
C C17 0.65622(18) 0.67848(5) 0.51235(16) 0.0246(3) Uani d . 1
C C18 0.8334(2) 0.71015(6) 0.3818(2) 0.0351(4) Uani d . 1
H H18A 0.8954 0.7317 0.4735 0.042 Uiso calc R 1
H H18B 0.7445 0.7305 0.3032 0.042 Uiso calc R 1
C C19 0.9537(2) 0.68897(7) 0.3101(2) 0.0422(4) Uani d . 1
H H19A 1.0469 0.6716 0.3918 0.063 Uiso calc R 1
H H19B 1.0003 0.7162 0.2652 0.063 Uiso calc R 1
H H19C 0.8928 0.6653 0.2263 0.063 Uiso calc R 1
C C20 0.76917(19) 0.63640(6) 0.84092(17) 0.0284(3) Uani d . 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'
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'
F F 0.0171 0.0103 '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
C17 O2 C18 115.89(12)
C4 N1 C1 117.02(12)
C2 N2 C5 133.83(11)
C2 N2 C1 120.72(11)
C5 N2 C1 105.42(11)
C1 N3 C6 104.76(11)
O3 N4 O4 123.49(12)
O3 N4 C14 118.27(11)
O4 N4 C14 118.23(11)
N3 C1 N1 125.63(12)
N3 C1 N2 113.11(12)
N1 C1 N2 121.23(12)
N2 C2 C3 117.29(12)
N2 C2 C11 120.05(12)
C3 C2 C11 122.61(12)
C2 C3 C4 118.54(13)
C2 C3 C17 119.40(12)
C4 C3 C17 122.05(12)
N1 C4 C3 124.75(13)
N1 C4 C20 114.58(12)
C3 C4 C20 120.66(13)
N2 C5 C10 132.99(13)
N2 C5 C6 104.70(12)
C10 C5 C6 122.20(13)
N3 C6 C7 127.89(13)
N3 C6 C5 111.94(12)
C7 C6 C5 120.13(13)
C8 C7 C6 117.67(13)
C8 C7 H7 121.2
C6 C7 H7 121.2
C7 C8 C9 121.65(14)
C7 C8 H8 119.2
C9 C8 H8 119.2
C10 C9 C8 121.95(14)
C10 C9 H9 119.0
C8 C9 H9 119.0
C9 C10 C5 116.31(13)
C9 C10 H10 121.8
C5 C10 H10 121.8
C16 C11 C12 120.43(12)
C16 C11 C2 120.19(12)
C12 C11 C2 119.22(12)
C13 C12 C11 119.95(13)
C13 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C12 118.30(12)
C14 C13 H13 120.9
C12 C13 H13 120.9
C15 C14 C13 123.03(12)
C15 C14 N4 118.63(12)
C13 C14 N4 118.34(12)
C14 C15 C16 118.21(13)
C14 C15 H15 120.9
C16 C15 H15 120.9
C15 C16 C11 120.07(13)
C15 C16 H16 120.0
C11 C16 H16 120.0
O1 C17 O2 125.91(14)
O1 C17 C3 123.53(13)
O2 C17 C3 110.57(12)
O2 C18 C19 106.55(13)
O2 C18 H18A 110.4
C19 C18 H18A 110.4
O2 C18 H18B 110.4
C19 C18 H18B 110.4
H18A C18 H18B 108.6
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
F1 C20 F2 107.24(12)
F1 C20 F3 107.08(12)
F2 C20 F3 107.02(12)
F1 C20 C4 112.34(12)
F2 C20 C4 110.55(12)
F3 C20 C4 112.33(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C20 1.3304(17)
F2 C20 1.3365(17)
F3 C20 1.3372(18)
O1 C17 1.2004(18)
O2 C17 1.3277(17)
O2 C18 1.4617(17)
O3 N4 1.2239(15)
O4 N4 1.2289(15)
N1 C4 1.3056(18)
N1 C1 1.3522(18)
N2 C2 1.3719(17)
N2 C5 1.3989(17)
N2 C1 1.4235(16)
N3 C1 1.3108(18)
N3 C6 1.3851(19)
N4 C14 1.4755(16)
C2 C3 1.3729(19)
C2 C11 1.4861(18)
C3 C4 1.4248(18)
C3 C17 1.5049(19)
C4 C20 1.516(2)
C5 C10 1.4004(19)
C5 C6 1.4084(19)
C6 C7 1.399(2)
C7 C8 1.376(2)
C7 H7 0.9500
C8 C9 1.405(2)
C8 H8 0.9500
C9 C10 1.381(2)
C9 H9 0.9500
C10 H10 0.9500
C11 C16 1.3941(19)
C11 C12 1.3978(18)
C12 C13 1.3865(18)
C12 H12 0.9500
C13 C14 1.3864(19)
C13 H13 0.9500
C14 C15 1.3830(19)
C15 C16 1.3890(19)
C15 H15 0.9500
C16 H16 0.9500
C18 C19 1.495(2)
C18 H18A 0.9900
C18 H18B 0.9900
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
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
C12 H12 N3 3_666 0.95 2.41 3.2987(18) 156
C16 H16 O3 4_576 0.95 2.55 3.2096(18) 127
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
C6 N3 C1 N1 176.80(12)
C6 N3 C1 N2 -1.36(15)
C4 N1 C1 N3 -178.44(13)
C4 N1 C1 N2 -0.42(18)
C2 N2 C1 N3 -175.64(11)
C5 N2 C1 N3 2.61(15)
C2 N2 C1 N1 6.11(18)
C5 N2 C1 N1 -175.64(11)
C5 N2 C2 C3 174.80(13)
C1 N2 C2 C3 -7.54(18)
C5 N2 C2 C11 -7.8(2)
C1 N2 C2 C11 169.83(11)
N2 C2 C3 C4 3.79(18)
C11 C2 C3 C4 -173.52(12)
N2 C2 C3 C17 -177.54(11)
C11 C2 C3 C17 5.16(19)
C1 N1 C4 C3 -3.5(2)
C1 N1 C4 C20 175.22(12)
C2 C3 C4 N1 1.9(2)
C17 C3 C4 N1 -176.76(13)
C2 C3 C4 C20 -176.79(12)
C17 C3 C4 C20 4.6(2)
C2 N2 C5 C10 -8.5(2)
C1 N2 C5 C10 173.60(14)
C2 N2 C5 C6 175.31(13)
C1 N2 C5 C6 -2.60(13)
C1 N3 C6 C7 -178.26(13)
C1 N3 C6 C5 -0.43(15)
N2 C5 C6 N3 1.99(14)
C10 C5 C6 N3 -174.73(12)
N2 C5 C6 C7 -179.99(12)
C10 C5 C6 C7 3.3(2)
N3 C6 C7 C8 175.79(13)
C5 C6 C7 C8 -1.88(19)
C6 C7 C8 C9 -0.6(2)
C7 C8 C9 C10 1.9(2)
C8 C9 C10 C5 -0.5(2)
N2 C5 C10 C9 -177.67(14)
C6 C5 C10 C9 -2.0(2)
N2 C2 C11 C16 123.17(14)
C3 C2 C11 C16 -59.60(18)
N2 C2 C11 C12 -61.32(17)
C3 C2 C11 C12 115.92(15)
C16 C11 C12 C13 -0.8(2)
C2 C11 C12 C13 -176.33(12)
C11 C12 C13 C14 0.0(2)
C12 C13 C14 C15 0.9(2)
C12 C13 C14 N4 -178.87(12)
O3 N4 C14 C15 4.90(19)
O4 N4 C14 C15 -174.11(13)
O3 N4 C14 C13 -175.37(13)
O4 N4 C14 C13 5.63(18)
C13 C14 C15 C16 -0.8(2)
N4 C14 C15 C16 178.91(12)
C14 C15 C16 C11 -0.1(2)
C12 C11 C16 C15 0.9(2)
C2 C11 C16 C15 176.33(13)
C18 O2 C17 O1 -3.0(2)
C18 O2 C17 C3 176.91(12)
C2 C3 C17 O1 106.37(17)
C4 C3 C17 O1 -75.00(19)
C2 C3 C17 O2 -73.58(16)
C4 C3 C17 O2 105.05(14)
C17 O2 C18 C19 174.18(13)
N1 C4 C20 F1 22.08(18)
C3 C4 C20 F1 -159.12(13)
N1 C4 C20 F2 -97.67(14)
C3 C4 C20 F2 81.13(16)
N1 C4 C20 F3 142.87(13)
C3 C4 C20 F3 -38.33(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741263
