#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/01/2210124.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_2210124
loop_
_publ_author_name
'Kruszynski, Rafal'
'Trzesowska, Agata'
'Czestkowski, Wojciech'
'Bartczak, Tadeusz J.'
'Mikiciuk-Olasik, Elżbieta'
_publ_section_title
;
 4-(2-Benzylaminoacetyl)-1,2,3,4-tetrahydroquinoxalin-2-one
;
_journal_coeditor_code           BT2171
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3974
_journal_page_last               o3976
_journal_paper_doi               10.1107/S1600536806032661
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H17 N3 O2'
_chemical_formula_moiety         'C17 H17 N3 O2'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.34
_chemical_name_systematic
;
4-(2-Benzylaminoacetyl)-1,2,3,4-tetrahydroquinoxalin-2-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.77(3)
_cell_angle_beta                 93.16(3)
_cell_angle_gamma                96.04(3)
_cell_formula_units_Z            2
_cell_length_a                   4.7010(10)
_cell_length_b                   12.415(2)
_cell_length_c                   14.083(3)
_cell_measurement_reflns_used    99
_cell_measurement_temperature    291.0(3)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      4
_cell_volume                     760.5(3)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma, 1993)'
_computing_data_reduction        'DATAPROC (Gałdecki et al.,  1998)'
_computing_molecular_graphics
;
XP in SHELXTL/PC (Sheldrick, 1990b)
ORTEP-3 (Version 1.062; Farrugia, 1997) and
MERCURY (Version 1.4; Macrae et al.,  2006)
;
_computing_publication_material
;
SHELXL97 and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      291.0(3)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3332
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         80.71
_diffrn_reflns_theta_min         3.37
_diffrn_standards_decay_%        11.2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.077P)²+0.1995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1554
_reflns_number_gt                2835
_reflns_number_total             3191
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2171.cif
_cod_data_source_block           II
_cod_database_code               2210124
_cod_database_fobs_code          2210124
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4465(3) 0.46485(11) 0.26107(9) 0.0411(3) Uani d . 1 . .
O O1 0.0468(3) 0.60225(11) 0.12859(9) 0.0595(4) Uani d . 1 . .
O O11 0.2272(3) 0.53381(10) 0.40433(9) 0.0605(4) Uani d . 1 . .
N N2 0.2493(3) 0.43696(11) 0.06757(10) 0.0469(3) Uani d . 1 . .
H H2N 0.1514 0.4216 0.0080 0.056 Uiso d R 1 . .
N N3 0.1126(3) 0.32776(11) 0.42530(9) 0.0444(3) Uani d . 1 . .
H H3N 0.0938 0.3986 0.4713 0.053 Uiso d R 1 . .
C C1 0.5428(3) 0.37455(13) 0.17962(11) 0.0392(3) Uani d . 1 . .
C C2 0.7312(4) 0.30156(15) 0.19305(12) 0.0472(4) Uani d . 1 . .
H H2 0.8084 0.3115 0.2583 0.057 Uiso calc R 1 . .
C C3 0.8046(4) 0.21369(17) 0.10903(14) 0.0566(4) Uani d . 1 . .
H H3 0.9268 0.1632 0.1183 0.068 Uiso calc R 1 . .
C C4 0.6979(4) 0.20048(17) 0.01168(14) 0.0592(5) Uani d . 1 . .
H H4 0.7476 0.1411 -0.0444 0.071 Uiso calc R 1 . .
C C5 0.5179(4) 0.27530(15) -0.00244(12) 0.0517(4) Uani d . 1 . .
H H5 0.4490 0.2672 -0.0681 0.062 Uiso calc R 1 . .
C C6 0.4390(3) 0.36271(13) 0.08095(11) 0.0420(3) Uani d . 1 . .
C C7 0.2157(4) 0.53793(13) 0.14071(12) 0.0456(4) Uani d . 1 . .
C C8 0.4070(4) 0.56881(13) 0.23882(12) 0.0485(4) Uani d . 1 . .
H H8A 0.5924 0.6071 0.2330 0.058 Uiso calc R 1 . .
H H8B 0.3214 0.6225 0.2945 0.058 Uiso calc R 1 . .
C C11 0.3340(3) 0.45355(13) 0.34560(10) 0.0411(3) Uani d . 1 . .
C C12 0.3461(3) 0.34270(13) 0.36611(11) 0.0422(3) Uani d . 1 . .
H H12A 0.3291 0.2771 0.3021 0.051 Uiso calc R 1 . .
H H12B 0.5289 0.3465 0.4035 0.051 Uiso calc R 1 . .
C C13 0.1512(5) 0.24340(15) 0.47346(12) 0.0554(4) Uani d . 1 . .
H H13A 0.0177 0.2518 0.5249 0.067 Uiso calc R 1 . .
H H13B 0.3445 0.2603 0.5076 0.067 Uiso calc R 1 . .
C C14 0.1048(4) 0.11929(15) 0.39918(13) 0.0503(4) Uani d . 1 . .
C C17 0.0146(7) -0.1107(2) 0.2654(2) 0.0886(8) Uani d . 1 . .
H H17 -0.0175 -0.1874 0.2201 0.106 Uiso calc R 1 A 1
C C15' -0.041(2) 0.0839(7) 0.3020(6) 0.0552(16) Uani d P 0.480(17) B 2
H H15' -0.1176 0.1395 0.2818 0.066 Uiso calc PR 0.480(17) B 2
C C16' -0.078(2) -0.0291(7) 0.2348(7) 0.072(2) Uani d P 0.480(17) B 2
H H16' -0.1655 -0.0486 0.1690 0.086 Uiso calc PR 0.480(17) B 2
C C18' 0.143(3) -0.0844(7) 0.3605(9) 0.085(2) Uani d P 0.480(17) B 2
H H18' 0.2015 -0.1430 0.3805 0.103 Uiso calc PR 0.480(17) B 2
C C19' 0.187(2) 0.0299(5) 0.4283(6) 0.0656(19) Uani d P 0.480(17) B 2
H H19' 0.2726 0.0471 0.4941 0.079 Uiso calc PR 0.480(17) B 2
C C15 -0.125(2) 0.0841(7) 0.3299(9) 0.070(2) Uani d P 0.520(17) B 1
H H15 -0.2481 0.1365 0.3260 0.085 Uiso calc PR 0.520(17) B 1
C C16 -0.177(3) -0.0309(8) 0.2637(9) 0.092(3) Uani d P 0.520(17) B 1
H H16 -0.3414 -0.0559 0.2175 0.110 Uiso calc PR 0.520(17) B 1
C C18 0.249(2) -0.0711(8) 0.3364(9) 0.093(2) Uani d P 0.520(17) B 1
H H18 0.3755 -0.1223 0.3410 0.111 Uiso calc PR 0.520(17) B 1
C C19 0.302(2) 0.0446(5) 0.4016(7) 0.0728(18) Uani d P 0.520(17) B 1
H H19 0.4686 0.0717 0.4466 0.087 Uiso calc PR 0.520(17) B 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C11 N1 C1 125.98(12) n
C11 N1 C8 118.09(13) n
C1 N1 C8 114.39(12) n
C7 N2 C6 123.31(14) n
C7 N2 H2N 115.6 n
C6 N2 H2N 121.0 n
C12 N3 C13 113.15(13) n
C12 N3 H3N 107.7 n
C13 N3 H3N 112.2 n
C2 C1 C6 119.70(14) n
C2 C1 N1 124.13(13) n
C6 C1 N1 116.17(13) n
C1 C2 C3 119.80(15) n
C1 C2 H2 120.1 n
C3 C2 H2 120.1 n
C4 C3 C2 120.51(16) n
C4 C3 H3 119.7 n
C2 C3 H3 119.7 n
C5 C4 C3 119.98(16) n
C5 C4 H4 120.0 n
C3 C4 H4 120.0 n
C4 C5 C6 120.24(16) n
C4 C5 H5 119.9 n
C6 C5 H5 119.9 n
C5 C6 C1 119.70(15) n
C5 C6 N2 120.69(14) n
C1 C6 N2 119.58(14) n
O1 C7 N2 122.90(15) n
O1 C7 C8 122.08(15) n
N2 C7 C8 115.00(14) n
N1 C8 C7 110.73(13) n
N1 C8 H8A 109.5 n
C7 C8 H8A 109.5 n
N1 C8 H8B 109.5 n
C7 C8 H8B 109.5 n
H8A C8 H8B 108.1 n
O11 C11 N1 119.82(14) n
O11 C11 C12 120.36(14) n
N1 C11 C12 119.81(13) n
N3 C12 C11 109.11(12) n
N3 C12 H12A 109.9 n
C11 C12 H12A 109.9 n
N3 C12 H12B 109.9 n
C11 C12 H12B 109.9 n
H12A C12 H12B 108.3 n
N3 C13 C14 113.35(13) n
N3 C13 H13A 108.9 n
C14 C13 H13A 108.9 n
N3 C13 H13B 108.9 n
C14 C13 H13B 108.9 n
H13A C13 H13B 107.7 n
C15 C14 C19 121.0(5) n
C15' C14 C19' 115.3(4) n
C15 C14 C13 118.9(4) n
C19 C14 C13 120.0(3) n
C15' C14 C13 123.8(4) n
C19' C14 C13 120.7(3) n
C16' C17 C18' 121.5(5) n
C18 C17 C16 117.6(5) n
C16' C17 H17 118.1 n
C18' C17 H17 120.4 n
C18 C17 H17 121.2 n
C16 C17 H17 121.2 n
C16' C15' C14 123.0(8) n
C16' C15' H15' 118.5 n
C14 C15' H15' 118.5 n
C17 C16' C15' 118.9(8) n
C17 C16' H16' 120.6 n
C15' C16' H16' 120.6 n
C17 C18' C19' 120.2(6) n
C17 C18' H18' 119.9 n
C19' C18' H18' 119.9 n
C18' C19' C14 120.8(6) n
C18' C19' H19' 119.6 n
C14 C19' H19' 119.6 n
C14 C15 C16 119.7(8) n
C14 C15 H15 120.1 n
C16 C15 H15 120.1 n
C15 C16 C17 120.9(8) n
C15 C16 H16 119.5 n
C17 C16 H16 119.5 n
C17 C18 C19 121.0(7) n
C17 C18 H18 119.5 n
C19 C18 H18 119.5 n
C14 C19 C18 119.5(6) n
C14 C19 H19 120.3 n
C18 C19 H19 120.3 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C11 1.3743(19) n
N1 C1 1.4247(18) n
N1 C8 1.4593(19) n
O1 C7 1.230(2) n
O11 C11 1.2230(19) n
N2 C7 1.342(2) n
N2 C6 1.399(2) n
N2 H2N 0.8824 n
N3 C12 1.450(2) n
N3 C13 1.456(2) n
N3 H3N 0.9049 n
C1 C2 1.383(2) n
C1 C6 1.399(2) n
C2 C3 1.385(2) n
C2 H2 0.9300 n
C3 C4 1.380(3) n
C3 H3 0.9300 n
C4 C5 1.377(3) n
C4 H4 0.9300 n
C5 C6 1.387(2) n
C5 H5 0.9300 n
C7 C8 1.510(2) n
C8 H8A 0.9700 n
C8 H8B 0.9700 n
C11 C12 1.509(2) n
C12 H12A 0.9700 n
C12 H12B 0.9700 n
C13 C14 1.509(2) n
C13 H13A 0.9700 n
C13 H13B 0.9700 n
C14 C15 1.337(10) n
C14 C19 1.387(6) n
C14 C15' 1.394(9) n
C14 C19' 1.395(5) n
C17 C16' 1.335(10) n
C17 C18' 1.349(11) n
C17 C18 1.369(11) n
C17 C16 1.414(11) n
C17 H17 0.9300 n
C15' C16' 1.373(11) n
C15' H15' 0.9300 n
C16' H16' 0.9300 n
C18' C19' 1.387(11) n
C18' H18' 0.9300 n
C19' H19' 0.9300 n
C15 C16 1.388(12) n
C15 H15 0.9300 n
C16 H16 0.9300 n
C18 C19 1.391(11) n
C18 H18 0.9300 n
C19 H19 0.9300 n
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
N2 H2N O1 2_565 0.88 2.00 2.879(2) 175.0
N3 H3N O11 . 0.90 2.25 2.6804(18) 108.6
N3 H3N O11 2_566 0.90 2.36 3.056(2) 133.8
C2 H2 N3 1_655 0.93 2.62 3.535(2) 169.2
C8 H8B O11 . 0.97 2.23 2.682(2) 107.1
C17 H17 O1 1_545 0.93 2.53 3.422(3) 161.1
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
_geom_torsion_publ_flag
C11 N1 C1 C2 -50.3(2) n
C8 N1 C1 C2 144.16(16) n
C11 N1 C1 C6 130.61(16) n
C8 N1 C1 C6 -34.89(19) n
C6 C1 C2 C3 -3.2(2) n
N1 C1 C2 C3 177.82(15) n
C1 C2 C3 C4 1.9(3) n
C2 C3 C4 C5 0.3(3) n
C3 C4 C5 C6 -1.2(3) n
C4 C5 C6 C1 -0.1(3) n
C4 C5 C6 N2 -178.06(16) n
C2 C1 C6 C5 2.2(2) n
N1 C1 C6 C5 -178.66(14) n
C2 C1 C6 N2 -179.74(14) n
N1 C1 C6 N2 -0.7(2) n
C7 N2 C6 C5 -164.15(16) n
C7 N2 C6 C1 17.9(2) n
C6 N2 C7 O1 -179.41(15) n
C6 N2 C7 C8 2.1(2) n
C11 N1 C8 C7 -113.87(16) n
C1 N1 C8 C7 52.85(19) n
O1 C7 C8 N1 145.30(16) n
N2 C7 C8 N1 -36.2(2) n
C1 N1 C11 O11 -171.28(15) n
C8 N1 C11 O11 -6.3(2) n
C1 N1 C11 C12 9.4(2) n
C8 N1 C11 C12 174.44(13) n
C13 N3 C12 C11 -163.52(13) n
O11 C11 C12 N3 27.0(2) n
N1 C11 C12 N3 -153.67(14) n
C12 N3 C13 C14 -73.1(2) n
N3 C13 C14 C15 -45.8(7) n
N3 C13 C14 C19 132.5(6) n
N3 C13 C14 C15' -18.3(6) n
N3 C13 C14 C19' 167.4(6) n
C15 C14 C15' C16' -95.3(18) n
C19 C14 C15' C16' 25.8(8) n
C19' C14 C15' C16' -6.4(8) n
C13 C14 C15' C16' 179.0(5) n
C18' C17 C16' C15' -0.1(9) n
C18 C17 C16' C15' -30.8(8) n
C16 C17 C16' C15' 73.5(13) n
C14 C15' C16' C17 4.3(10) n
C16' C17 C18' C19' -1.4(10) n
C18 C17 C18' C19' 80.6(13) n
C16 C17 C18' C19' -29.0(9) n
C17 C18' C19' C14 -1.1(10) n
C15 C14 C19' C18' 30.8(8) n
C19 C14 C19' C18' -82.6(9) n
C15' C14 C19' C18' 4.7(8) n
C13 C14 C19' C18' 179.5(5) n
C19 C14 C15 C16 4.4(8) n
C15' C14 C15 C16 73.9(16) n
C19' C14 C15 C16 -28.0(8) n
C13 C14 C15 C16 -177.3(5) n
C14 C15 C16 C17 -2.7(11) n
C16' C17 C16 C15 -87.1(16) n
C18' C17 C16 C15 31.7(9) n
C18 C17 C16 C15 1.7(10) n
C16' C17 C18 C19 27.1(9) n
C18' C17 C18 C19 -85.5(13) n
C16 C17 C18 C19 -2.4(9) n
C15 C14 C19 C18 -5.1(8) n
C15' C14 C19 C18 -29.0(7) n
C19' C14 C19 C18 76.5(9) n
C13 C14 C19 C18 176.7(5) n
C17 C18 C19 C14 4.1(10) n
