#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/07/2200758.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_2200758
loop_
_publ_author_name
'David W Jeffery'
'Rolf H Prager'
'Max R Taylor'
_publ_section_title
;
 Ethyl 6-nitro-2-phenylaminoimidazo[1,2-a]pyridine-3-carboxylate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o980
_journal_page_last               o982
_journal_paper_doi               10.1107/S1600536801015574
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C16 H14 N4 O4'
_chemical_formula_moiety         'C16 H14 N4 O4'
_chemical_formula_sum            'C16 H14 N4 O4'
_chemical_formula_weight         326.31
_chemical_melting_point          201.0(10)
_chemical_name_systematic
;
Ethyl 6-nitro-2-phenylaminoimidazo[1,2-a]pyridine-3-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                104.380(10)
_cell_angle_beta                 92.300(10)
_cell_angle_gamma                110.070(10)
_cell_formula_units_Z            2
_cell_length_a                   7.868(4)
_cell_length_b                   8.489(4)
_cell_length_c                   12.281(6)
_cell_measurement_reflns_used    2508
_cell_measurement_temperature    168(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.7
_cell_volume                     739.2(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'Xtal3.7 ADDREF SORTRF (Hall et al., 2000)'
_computing_molecular_graphics    Xtal3.7
_computing_publication_material  'Xtal3.7 BONDLA CIFIO'
_computing_structure_refinement  'Xtal3.7 CRYLSQ'
_computing_structure_solution    'SIR97 (Altomare et al., 1994)'
_diffrn_ambient_temperature      168(2)
_diffrn_measured_fraction_theta_full .99
_diffrn_measured_fraction_theta_max .99
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .03
_diffrn_reflns_av_sigmaI/netI    .054
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9625
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          .57
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          .035
_refine_diff_density_max         .35
_refine_diff_density_min         -.43
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.01
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .086
_refine_ls_R_factor_gt           .052
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fₒ²) + (0.04Fₒ²)²]^1/2^'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .095
_refine_ls_wR_factor_ref         .088
_reflns_number_gt                2173
_reflns_number_total             2989
_reflns_threshold_expression     Fsqd>σ(Fsqd)
_cod_data_source_file            tk6038.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '200-202' was changed to '201.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '200-202' was changed to '201.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     -P_1
_cod_database_code               2200758
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,-y,-z
loop_
_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_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 -.2799(2) .2258(2) .41191(14) .0495(8) Uani ? ? 1.00000 ? ?
O2 -.1648(2) .5073(2) .44612(13) .0386(8) Uani ? ? 1.00000 ? ?
O3 .3638(2) .87524(19) .11382(12) .0347(7) Uani ? ? 1.00000 ? ?
O4 .1937(2) .83149(18) .25432(12) .0325(7) Uani ? ? 1.00000 ? ?
N1 .1324(2) .3158(2) -.00132(14) .0276(8) Uani ? ? 1.00000 ? ?
N2 -.1906(2) .3598(3) .38705(16) .0328(9) Uani ? ? 1.00000 ? ?
N3 .3374(2) .5649(2) -.05142(15) .0287(8) Uani ? ? 1.00000 ? ?
N4 .0750(2) .4668(2) .16308(14) .0247(8) Uani ? ? 1.00000 ? ?
C2 .2267(3) .4901(3) .01771(18) .0261(9) Uani ? ? 1.00000 ? ?
C3 .1960(3) .5902(3) .11813(17) .0250(9) Uani ? ? 1.00000 ? ?
C5 .0016(3) .4851(3) .26123(18) .0261(9) Uani ? ? 1.00000 ? ?
C6 -.1143(3) .3379(3) .28145(18) .0269(10) Uani ? ? 1.00000 ? ?
C7 -.1617(3) .1717(3) .20586(19) .0321(10) Uani ? ? 1.00000 ? ?
C8 -.0836(3) .1543(3) .1095(2) .0314(10) Uani ? ? 1.00000 ? ?
C9 .0402(3) .3024(3) .08636(18) .0261(9) Uani ? ? 1.00000 ? ?
C10 .2604(3) .7766(3) .15997(19) .0285(10) Uani ? ? 1.00000 ? ?
C11 .2431(3) 1.0191(3) .2992(2) .0374(11) Uani ? ? 1.00000 ? ?
C12 .1466(3) 1.0451(3) .4000(2) .0456(12) Uani ? ? 1.00000 ? ?
C13 .3876(3) .4878(3) -.15353(17) .0257(9) Uani ? ? 1.00000 ? ?
C14 .5070(3) .6015(3) -.20474(19) .0295(10) Uani ? ? 1.00000 ? ?
C15 .5639(3) .5360(3) -.3044(2) .0330(10) Uani ? ? 1.00000 ? ?
C16 .5046(3) .3576(3) -.35488(19) .0337(11) Uani ? ? 1.00000 ? ?
C17 .3852(3) .2461(3) -.30422(19) .0338(10) Uani ? ? 1.00000 ? ?
C18 .3249(3) .3085(3) -.20435(18) .0303(10) Uani ? ? 1.00000 ? ?
H3 .38760 .68500 -.02772 .03600 Uiso ? ? 1.00000 ? ?
H5 .03002 .59664 .31390 .03300 Uiso ? ? 1.00000 ? ?
H7 -.24704 .07252 .22192 .04000 Uiso ? ? 1.00000 ? ?
H8 -.11255 .04201 .05760 .03900 Uiso ? ? 1.00000 ? ?
H14 .54904 .72409 -.17082 .03700 Uiso ? ? 1.00000 ? ?
H15 .64531 .61410 -.33914 .04100 Uiso ? ? 1.00000 ? ?
H16 .54558 .31297 -.42348 .04200 Uiso ? ? 1.00000 ? ?
H17 .34349 .12360 -.33866 .04200 Uiso ? ? 1.00000 ? ?
H18 .24138 .23001 -.17079 .03800 Uiso ? ? 1.00000 ? ?
H11a .37155 1.07461 .32075 .04700 Uiso ? ? 1.00000 ? ?
H11b .20506 1.06541 .24390 .04700 Uiso ? ? 1.00000 ? ?
H12a .17466 1.16653 .43268 .06800 Uiso ? ? 1.00000 ? ?
H12b .18506 .99741 .45431 .06800 Uiso ? ? 1.00000 ? ?
H12c .01857 .98822 .37748 .06800 Uiso ? ? 1.00000 ? ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
N .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O .008 .006 'Int Tables Vol IV Tables 2.2B and 2.3.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 O4 C11 116.71(18)
C9 N1 C2 105.10(17)
O2 N2 O1 123.6(2)
O2 N2 C6 119.27(19)
O1 N2 C6 117.08(18)
H3 N3 C2 114.99
H3 N3 C13 115.01
C2 N3 C13 130.00(17)
C5 N4 C3 131.19(17)
C5 N4 C9 122.07(18)
C3 N4 C9 106.71(17)
N3 C2 N1 125.7(2)
N3 C2 C3 121.48(19)
N1 C2 C3 112.8(2)
C2 C3 N4 103.88(17)
C2 C3 C10 127.9(2)
N4 C3 C10 128.0(2)
H5 C5 N4 121.3
H5 C5 C6 121.3
N4 C5 C6 117.41(18)
C5 C6 C7 123.2(2)
C5 C6 N2 116.66(18)
C7 C6 N2 120.1(2)
H7 C7 C8 120.6
H7 C7 C6 120.6
C8 C7 C6 118.9(2)
H8 C8 C7 120.1
H8 C8 C9 120.1
C7 C8 C9 119.83(19)
N1 C9 C8 130.00(19)
N1 C9 N4 111.50(18)
C8 C9 N4 118.5(2)
O3 C10 O4 123.4(2)
O3 C10 C3 123.7(2)
O4 C10 C3 112.9(2)
H11b C11 H11a 109.5
H11b C11 O4 110.27
H11b C11 C12 110.3
H11a C11 O4 110.3
H11a C11 C12 110.3
O4 C11 C12 106.15(18)
H12b C12 H12c 109.5
H12b C12 H12a 109.5
H12b C12 C11 109.5
H12c C12 H12a 109.5
H12c C12 C11 109.5
H12a C12 C11 109.4
C18 C13 C14 119.8(2)
C18 C13 N3 123.9(2)
C14 C13 N3 116.26(18)
H14 C14 C15 120.1
H14 C14 C13 120.1
C15 C14 C13 119.8(2)
H15 C15 C14 119.5
H15 C15 C16 119.6
C14 C15 C16 120.9(2)
H16 C16 C17 120.5
H16 C16 C15 120.5
C17 C16 C15 118.9(2)
H17 C17 C16 119.3
H17 C17 C18 119.3
C16 C17 C18 121.3(2)
H18 C18 C17 120.4
H18 C18 C13 120.4
C17 C18 C13 119.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N2 . . 1.233(3) y
O2 N2 . . 1.224(3) y
O3 C10 . . 1.220(3) ?
O4 C10 . . 1.336(3) ?
O4 C11 . . 1.454(3) ?
N1 C9 . . 1.329(3) y
N1 C2 . . 1.362(3) y
N2 C6 . . 1.448(3) y
N3 H3 . . .920 ?
N3 C2 . . 1.353(3) y
N3 C13 . . 1.402(3) y
N4 C5 . . 1.355(3) y
N4 C3 . . 1.398(3) y
N4 C9 . . 1.405(3) y
C2 C3 . . 1.395(3) y
C3 C10 . . 1.431(3) y
C5 H5 . . .951 ?
C5 C6 . . 1.358(3) y
C6 C7 . . 1.397(3) y
C7 H7 . . .951 ?
C7 C8 . . 1.355(3) y
C8 H8 . . .951 ?
C8 C9 . . 1.403(3) y
C11 H11b . . .950 ?
C11 H11a . . .950 ?
C11 C12 . . 1.488(4) ?
C12 H12b . . .950 ?
C12 H12c . . .950 ?
C12 H12a . . .950 ?
C13 C18 . . 1.392(3) ?
C13 C14 . . 1.392(3) ?
C14 H14 . . .951 ?
C14 C15 . . 1.373(3) ?
C15 H15 . . .950 ?
C15 C16 . . 1.386(3) ?
C16 H16 . . .951 ?
C16 C17 . . 1.376(3) ?
C17 H17 . . .951 ?
C17 C18 . . 1.381(3) ?
C18 H18 . . .950 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 O3 .92 2.12 2.835(2) 133 yes
C5 H5 O4 .95 2.28 2.832(3) 116 yes
C18 H18 N1 .95 2.33 2.967(3) 124 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132691
