#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/07/2200715.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_2200715
loop_
_publ_author_name
'John M. Rowland'
'Gerardo J. Ibanez'
'Marilyn M. Olmstead'
'Michael Ruf'
'Pradip K. Mascharak'
_publ_section_title
;
 Nitrilotriacetanilide
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1001
_journal_page_last               o1003
_journal_paper_doi               10.1107/S1600536801015781
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C24 H24 N4 O3'
_chemical_formula_moiety         'C24 H24 N4 O3'
_chemical_formula_sum            'C24 H24 N4 O3'
_chemical_formula_weight         416.47
_chemical_name_common            Nitrilotrisacetanilide
_chemical_name_systematic
;
Nitrilotriacetanilide
;
_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                84.684(6)
_cell_angle_beta                 82.425(6)
_cell_angle_gamma                68.439(6)
_cell_formula_units_Z            2
_cell_length_a                   8.411(2)
_cell_length_b                   8.819(2)
_cell_length_c                   14.886(4)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    91(2)
_cell_measurement_theta_max      31.1
_cell_measurement_theta_min      2.5
_cell_volume                     1016.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      91(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full .97
_diffrn_measured_fraction_theta_max .822
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .060
_diffrn_reflns_av_sigmaI/netI    .060
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7955,7827
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .28
_exptl_crystal_size_min          .04
_refine_diff_density_max         .594
_refine_diff_density_min         -.471
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         8879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          .087
_refine_ls_R_factor_gt           .067
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0619P)²+3.3081P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .239
_reflns_number_gt                6786
_reflns_number_total             8879
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6075.cif
_cod_data_source_block           I
_cod_original_cell_volume        1016.7(4)
_cod_database_code               2200715
_cod_database_fobs_code          2200715
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .9631(3) .8152(3) .36205(19) .0216(6) Uani d . 1 . . O
O2 .4162(3) .7777(3) .55058(18) .0183(6) Uani d . 1 . . O
O3 .5423(4) .6546(3) .20056(19) .0210(6) Uani d . 1 . . O
N1 .8131(4) .7963(4) .2485(2) .0166(7) Uani d . 1 . . N
H1 .7138 .7918 .2391 .020 Uiso calc R 1 . . H
N2 .1558(4) .8082(4) .5056(2) .0166(6) Uani d . 1 . . N
H2 .0931 .8385 .4597 .020 Uiso calc R 1 . . H
N3 .5089(4) .4272(4) .2757(2) .0154(6) Uani d . 1 . . N
H3 .5055 .3799 .3303 .018 Uiso calc R 1 . . H
N4 .5471(4) .7814(3) .3632(2) .0149(6) Uani d . 1 . . N
C1 .6751(5) .8216(5) .4029(2) .0165(7) Uani d . 1 . . C
H1A .7121 .7464 .4562 .020 Uiso calc R 1 . . H
H1B .6224 .9340 .4244 .020 Uiso calc R 1 . . H
C2 .8330(5) .8093(4) .3353(3) .0162(7) Uani d . 1 . . C
C3 .9313(5) .7890(4) .1700(3) .0166(8) Uani d . 1 . . C
C4 1.0639(5) .8493(5) .1653(3) .0194(8) Uani d . 1 . . C
H4 1.0831 .8931 .2171 .023 Uiso calc R 1 . . H
C5 1.1674(5) .8448(5) .0844(3) .0229(9) Uani d . 1 . . C
H5 1.2585 .8850 .0813 .027 Uiso calc R 1 . . H
C6 1.1408(5) .7826(5) .0078(3) .0232(9) Uani d . 1 . . C
H6 1.2114 .7822 -.0475 .028 Uiso calc R 1 . . H
C7 1.0093(5) .7208(5) .0132(3) .0240(9) Uani d . 1 . . C
H7 .9911 .6756 -.0383 .029 Uiso calc R 1 . . H
C8 .9049(5) .7255(5) .0939(3) .0208(8) Uani d . 1 . . C
H8 .8141 .6847 .0972 .025 Uiso calc R 1 . . H
C9 .3682(5) .8678(4) .3951(3) .0168(7) Uani d . 1 . . C
H9A .2947 .8503 .3534 .020 Uiso calc R 1 . . H
H9B .3466 .9861 .3930 .020 Uiso calc R 1 . . H
C10 .3155(5) .8141(4) .4920(3) .0158(7) Uani d . 1 . . C
C11 .0814(4) .7566(4) .5885(3) .0161(7) Uani d . 1 . . C
C12 -.0152(5) .6591(5) .5836(3) .0188(8) Uani d . 1 . . C
H12 -.0329 .6326 .5263 .023 Uiso calc R 1 . . H
C13 -.0855(5) .6006(5) .6629(3) .0247(9) Uani d . 1 . . C
H13 -.1515 .5343 .6597 .030 Uiso calc R 1 . . H
C14 -.0596(5) .6388(5) .7459(3) .0240(9) Uani d . 1 . . C
H14 -.1056 .5966 .7999 .029 Uiso calc R 1 . . H
C15 .0328(5) .7379(5) .7512(3) .0248(9) Uani d . 1 . . C
H15 .0485 .7651 .8088 .030 Uiso calc R 1 . . H
C16 .1030(5) .7984(5) .6726(3) .0192(8) Uani d . 1 . . C
H16 .1653 .8678 .6764 .023 Uiso calc R 1 . . H
C17 .5886(5) .6060(4) .3583(3) .0158(7) Uani d . 1 . . C
H17A .5252 .5669 .4103 .019 Uiso calc R 1 . . H
H17B .7131 .5477 .3622 .019 Uiso calc R 1 . . H
C18 .5407(5) .5682(4) .2698(3) .0158(7) Uani d . 1 . . C
C19 .4806(4) .3471(4) .2044(3) .0151(7) Uani d . 1 . . C
C20 .4276(5) .4260(5) .1226(3) .0184(8) Uani d . 1 . . C
H20 .4136 .5377 .1112 .022 Uiso calc R 1 . . H
C21 .3950(5) .3413(5) .0574(3) .0191(8) Uani d . 1 . . C
H21 .3608 .3951 .0010 .023 Uiso calc R 1 . . H
C22 .4121(5) .1786(5) .0739(3) .0221(8) Uani d . 1 . . C
H22 .3878 .1219 .0295 .027 Uiso calc R 1 . . H
C23 .4649(5) .0997(5) .1558(3) .0224(9) Uani d . 1 . . C
H23 .4780 -.0118 .1672 .027 Uiso calc R 1 . . H
C24 .4984(5) .1831(5) .2207(3) .0197(8) Uani d . 1 . . C
H24 .5337 .1287 .2768 .024 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_publ_flag
C2 N1 C3 128.5(3) no
C2 N1 H1 115.7 ?
C3 N1 H1 115.7 ?
C10 N2 C11 124.9(3) no
C10 N2 H2 117.5 ?
C11 N2 H2 117.5 ?
C18 N3 C19 127.7(3) no
C18 N3 H3 116.2 ?
C19 N3 H3 116.2 ?
C9 N4 C1 116.9(3) no
C9 N4 C17 112.8(3) no
C1 N4 C17 113.6(3) no
N4 C1 C2 112.3(3) ?
N4 C1 H1A 109.1 ?
C2 C1 H1A 109.1 ?
N4 C1 H1B 109.1 ?
C2 C1 H1B 109.1 ?
H1A C1 H1B 107.9 ?
O1 C2 N1 125.3(4) no
O1 C2 C1 120.0(4) no
N1 C2 C1 114.7(3) ?
C8 C3 C4 119.7(4) ?
C8 C3 N1 117.0(3) ?
C4 C3 N1 123.2(4) ?
C5 C4 C3 119.2(4) ?
C5 C4 H4 120.4 ?
C3 C4 H4 120.4 ?
C4 C5 C6 121.3(4) ?
C4 C5 H5 119.3 ?
C6 C5 H5 119.3 ?
C5 C6 C7 119.1(4) ?
C5 C6 H6 120.4 ?
C7 C6 H6 120.4 ?
C8 C7 C6 119.8(4) ?
C8 C7 H7 120.1 ?
C6 C7 H7 120.1 ?
C3 C8 C7 120.8(4) ?
C3 C8 H8 119.6 ?
C7 C8 H8 119.6 ?
N4 C9 C10 113.8(3) ?
N4 C9 H9A 108.8 ?
C10 C9 H9A 108.8 ?
N4 C9 H9B 108.8 ?
C10 C9 H9B 108.8 ?
H9A C9 H9B 107.7 ?
O2 C10 N2 124.5(4) no
O2 C10 C9 120.7(3) no
N2 C10 C9 114.8(3) ?
C16 C11 C12 119.7(4) ?
C16 C11 N2 122.6(3) ?
C12 C11 N2 117.7(3) ?
C13 C12 C11 119.9(4) ?
C13 C12 H12 120.0 ?
C11 C12 H12 120.0 ?
C14 C13 C12 120.0(4) ?
C14 C13 H13 120.0 ?
C12 C13 H13 120.0 ?
C13 C14 C15 120.4(4) ?
C13 C14 H14 119.8 ?
C15 C14 H14 119.8 ?
C14 C15 C16 120.4(4) ?
C14 C15 H15 119.8 ?
C16 C15 H15 119.8 ?
C11 C16 C15 119.6(4) ?
C11 C16 H16 120.2 ?
C15 C16 H16 120.2 ?
N4 C17 C18 110.8(3) ?
N4 C17 H17A 109.5 ?
C18 C17 H17A 109.5 ?
N4 C17 H17B 109.5 ?
C18 C17 H17B 109.5 ?
H17A C17 H17B 108.1 ?
O3 C18 N3 125.3(4) no
O3 C18 C17 121.4(3) no
N3 C18 C17 113.1(3) ?
C20 C19 C24 119.4(4) ?
C20 C19 N3 123.1(3) ?
C24 C19 N3 117.4(3) ?
C19 C20 C21 119.9(4) ?
C19 C20 H20 120.1 ?
C21 C20 H20 120.1 ?
C22 C21 C20 120.6(4) ?
C22 C21 H21 119.7 ?
C20 C21 H21 119.7 ?
C23 C22 C21 119.5(4) ?
C23 C22 H22 120.2 ?
C21 C22 H22 120.2 ?
C24 C23 C22 120.1(4) ?
C24 C23 H23 120.0 ?
C22 C23 H23 120.0 ?
C23 C24 C19 120.5(4) ?
C23 C24 H24 119.7 ?
C19 C24 H24 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.233(4) y
O2 C10 . 1.234(4) y
O3 C18 . 1.225(4) y
N1 C2 . 1.345(5) y
N1 C3 . 1.421(5) y
N1 H1 . .8800 ?
N2 C10 . 1.351(5) y
N2 C11 . 1.422(5) y
N2 H2 . .8800 ?
N3 C18 . 1.357(5) y
N3 C19 . 1.419(5) y
N3 H3 . .8800 ?
N4 C9 . 1.451(5) y
N4 C1 . 1.457(4) y
N4 C17 . 1.462(4) y
C1 C2 . 1.533(5) ?
C1 H1A . .9900 ?
C1 H1B . .9900 ?
C3 C8 . 1.385(5) ?
C3 C4 . 1.393(5) ?
C4 C5 . 1.385(6) ?
C4 H4 . .9500 ?
C5 C6 . 1.386(6) ?
C5 H5 . .9500 ?
C6 C7 . 1.393(6) ?
C6 H6 . .9500 ?
C7 C8 . 1.386(6) ?
C7 H7 . .9500 ?
C8 H8 . .9500 ?
C9 C10 . 1.536(5) ?
C9 H9A . .9900 ?
C9 H9B . .9900 ?
C11 C16 . 1.389(5) ?
C11 C12 . 1.395(5) ?
C12 C13 . 1.391(6) ?
C12 H12 . .9500 ?
C13 C14 . 1.373(6) ?
C13 H13 . .9500 ?
C14 C15 . 1.380(6) ?
C14 H14 . .9500 ?
C15 C16 . 1.391(6) ?
C15 H15 . .9500 ?
C16 H16 . .9500 ?
C17 C18 . 1.526(5) ?
C17 H17A . .9900 ?
C17 H17B . .9900 ?
C19 C20 . 1.387(5) ?
C19 C24 . 1.400(5) ?
C20 C21 . 1.389(5) ?
C20 H20 . .9500 ?
C21 C22 . 1.390(6) ?
C21 H21 . .9500 ?
C22 C23 . 1.388(6) ?
C22 H22 . .9500 ?
C23 C24 . 1.382(5) ?
C23 H23 . .9500 ?
C24 H24 . .9500 ?
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
N3 H3 O2 2_666 .88 2.17 3.012(4) 161.4
N2 H2 O1 1_455 .88 2.00 2.830(4) 157.5
N1 H1 O3 . .88 2.35 3.153(4) 152.6
N1 H1 N4 . .88 2.18 2.665(5) 114.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4401232
