#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/41/2234133.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_2234133
loop_
_publ_author_name
'Ouzidan, Younes'
'Kandri Rodi, Youssef'
'Zouihri, Hafid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one
;
_journal_coeditor_code           BT5859
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1240
_journal_paper_doi               10.1107/S1600536812013177
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H7 N3 O3'
_chemical_formula_moiety         'C10 H7 N3 O3'
_chemical_formula_sum            'C10 H7 N3 O3'
_chemical_formula_weight         217.19
_chemical_name_systematic
;
5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.9780(10)
_cell_angle_beta                 92.0470(10)
_cell_angle_gamma                109.0430(10)
_cell_formula_units_Z            4
_cell_length_a                   7.2541(2)
_cell_length_b                   10.0362(2)
_cell_length_c                   14.6793(3)
_cell_measurement_reflns_used    5674
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.042
_cell_measurement_theta_min      2.198
_cell_volume                     986.20(4)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20686
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0746P)²+0.2589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                2855
_reflns_number_total             4506
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5859.cif
_cod_data_source_block           I
_cod_database_code               2234133
_cod_database_fobs_code          2234133
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_symmetry_multiplicity
O O1 0.4863(2) 0.28214(16) 0.32061(10) 0.0583(4) Uani d . 1 1
O O2 0.2729(3) 0.70175(19) -0.06407(12) 0.0780(5) Uani d . 1 1
O O3 0.4106(3) 0.84006(18) 0.06741(13) 0.0826(6) Uani d . 1 1
O O4 0.7053(2) 0.67457(15) 0.41638(10) 0.0556(4) Uani d . 1 1
O O5 1.0136(4) 0.2778(2) 0.79280(13) 0.1056(8) Uani d . 1 1
O O6 0.8109(3) 0.13338(17) 0.67890(13) 0.0826(6) Uani d . 1 1
N N1 0.4993(2) 0.47954(18) 0.25677(11) 0.0459(4) Uani d . 1 1
N N2 0.3361(2) 0.26206(16) 0.17380(10) 0.0438(4) Uani d . 1 1
N N3 0.3367(2) 0.72031(19) 0.01736(13) 0.0535(4) Uani d . 1 1
N N4 0.7143(2) 0.48027(17) 0.47997(11) 0.0416(4) Uani d . 1 1
N N5 0.8738(2) 0.70106(16) 0.55973(10) 0.0429(4) Uani d . 1 1
N N6 0.9101(3) 0.25456(19) 0.72058(13) 0.0583(5) Uani d . 1 1
C C1 0.4468(3) 0.3367(2) 0.25799(13) 0.0447(4) Uani d . 1 1
C C2 0.2539(3) 0.1058(2) 0.14690(15) 0.0555(5) Uani d . 1 1
H H2A 0.3007 0.0644 0.1936 0.067 Uiso calc R 1 1
H H2B 0.2988 0.0734 0.0880 0.067 Uiso calc R 1 1
C C3 0.0406(4) 0.0549(2) 0.13742(15) 0.0585(6) Uani d . 1 1
C C4 -0.1296(5) 0.0194(3) 0.1295(2) 0.0859(9) Uani d . 1 1
C C5 0.3154(3) 0.35855(19) 0.12192(12) 0.0391(4) Uani d . 1 1
C C6 0.2169(3) 0.3381(2) 0.03563(13) 0.0450(4) Uani d . 1 1
H H6 0.1471 0.2461 0.0011 0.054 Uiso calc R 1 1
C C7 0.2259(3) 0.4598(2) 0.00241(13) 0.0454(4) Uani d . 1 1
H H7 0.1628 0.4505 -0.0559 0.054 Uiso calc R 1 1
C C8 0.3287(3) 0.5950(2) 0.05579(13) 0.0418(4) Uani d . 1 1
C C9 0.4281(3) 0.6184(2) 0.14315(13) 0.0428(4) Uani d . 1 1
H H9 0.4961 0.7107 0.1778 0.051 Uiso calc R 1 1
C C10 0.4197(2) 0.49734(19) 0.17501(12) 0.0391(4) Uani d . 1 1
C C11 0.7577(3) 0.6231(2) 0.47796(13) 0.0432(4) Uani d . 1 1
C C12 0.9419(3) 0.8575(2) 0.58554(15) 0.0552(5) Uani d . 1 1
H H12A 0.8899 0.8870 0.6430 0.066 Uiso calc R 1 1
H H12B 0.8916 0.8943 0.5372 0.066 Uiso calc R 1 1
C C13 1.1548(4) 0.9205(2) 0.59851(15) 0.0621(6) Uani d . 1 1
C C14 1.3251(5) 0.9698(3) 0.6118(2) 0.0942(10) Uani d . 1 1
C C15 0.9034(3) 0.60770(18) 0.61264(12) 0.0381(4) Uani d . 1 1
C C16 1.0082(3) 0.6333(2) 0.69790(13) 0.0452(4) Uani d . 1 1
H H16 1.0756 0.7267 0.7310 0.054 Uiso calc R 1 1
C C17 1.0092(3) 0.5145(2) 0.73252(13) 0.0463(5) Uani d . 1 1
H H17 1.0786 0.5271 0.7898 0.056 Uiso calc R 1 1
C C18 0.9065(3) 0.3768(2) 0.68142(13) 0.0432(4) Uani d . 1 1
C C19 0.7999(3) 0.34865(19) 0.59536(12) 0.0404(4) Uani d . 1 1
H H19 0.7318 0.2552 0.5625 0.048 Uiso calc R 1 1
C C20 0.8012(2) 0.46764(19) 0.56177(12) 0.0371(4) Uani d . 1 1
H H1 0.574(3) 0.554(3) 0.3093(17) 0.073(7) Uiso d . 1 1
H H4 0.645(3) 0.409(2) 0.4297(16) 0.060(6) Uiso d . 1 1
H H41 -0.263(6) -0.002(4) 0.122(3) 0.138(14) Uiso d . 1 1
H H141 1.454(5) 1.011(3) 0.621(2) 0.118(12) Uiso d . 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C10 110.23(16)
C1 N1 H1 121.9(14)
C10 N1 H1 127.7(14)
C5 N2 C1 109.67(15)
C5 N2 C2 126.40(16)
C1 N2 C2 123.92(16)
O3 N3 O2 122.50(18)
O3 N3 C8 118.46(18)
O2 N3 C8 119.03(18)
C11 N4 C20 109.80(15)
C11 N4 H4 120.7(13)
C20 N4 H4 129.3(14)
C11 N5 C15 109.80(15)
C11 N5 C12 123.13(16)
C15 N5 C12 126.98(16)
O5 N6 O6 122.84(18)
O5 N6 C18 118.59(18)
O6 N6 C18 118.57(17)
O1 C1 N1 127.84(18)
O1 C1 N2 125.59(18)
N1 C1 N2 106.57(16)
N2 C2 C3 111.72(17)
N2 C2 H2A 109.3
C3 C2 H2A 109.3
N2 C2 H2B 109.3
C3 C2 H2B 109.3
H2A C2 H2B 107.9
C4 C3 C2 177.4(3)
C3 C4 H41 176(2)
C6 C5 N2 131.73(17)
C6 C5 C10 121.69(17)
N2 C5 C10 106.58(15)
C5 C6 C7 117.37(17)
C5 C6 H6 121.3
C7 C6 H6 121.3
C8 C7 C6 119.97(17)
C8 C7 H7 120.0
C6 C7 H7 120.0
C7 C8 C9 123.72(17)
C7 C8 N3 118.08(17)
C9 C8 N3 118.18(17)
C10 C9 C8 115.85(17)
C10 C9 H9 122.1
C8 C9 H9 122.1
C9 C10 N1 131.69(17)
C9 C10 C5 121.39(16)
N1 C10 C5 106.92(16)
O4 C11 N4 127.80(18)
O4 C11 N5 125.54(18)
N4 C11 N5 106.66(16)
N5 C12 C13 112.49(17)
N5 C12 H12A 109.1
C13 C12 H12A 109.1
N5 C12 H12B 109.1
C13 C12 H12B 109.1
H12A C12 H12B 107.8
C14 C13 C12 177.7(3)
C13 C14 H141 177(2)
C16 C15 N5 131.48(17)
C16 C15 C20 122.06(16)
N5 C15 C20 106.46(15)
C15 C16 C17 117.40(17)
C15 C16 H16 121.3
C17 C16 H16 121.3
C16 C17 C18 119.75(17)
C16 C17 H17 120.1
C18 C17 H17 120.1
C19 C18 C17 123.75(17)
C19 C18 N6 118.16(17)
C17 C18 N6 118.09(17)
C20 C19 C18 115.76(16)
C20 C19 H19 122.1
C18 C19 H19 122.1
C19 C20 N4 131.45(16)
C19 C20 C15 121.28(16)
N4 C20 C15 107.28(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.226(2)
O2 N3 1.224(2)
O3 N3 1.219(2)
O4 C11 1.229(2)
O5 N6 1.215(2)
O6 N6 1.219(2)
N1 C1 1.362(2)
N1 C10 1.380(2)
N1 H1 0.96(2)
N2 C5 1.381(2)
N2 C1 1.385(2)
N2 C2 1.452(2)
N3 C8 1.459(2)
N4 C11 1.370(2)
N4 C20 1.383(2)
N4 H4 0.92(2)
N5 C11 1.379(2)
N5 C15 1.387(2)
N5 C12 1.452(2)
N6 C18 1.457(2)
C2 C3 1.455(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.162(4)
C4 H41 0.92(4)
C5 C6 1.377(2)
C5 C10 1.406(2)
C6 C7 1.382(3)
C6 H6 0.9300
C7 C8 1.380(3)
C7 H7 0.9300
C8 C9 1.389(3)
C9 C10 1.367(3)
C9 H9 0.9300
C12 C13 1.455(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.164(4)
C14 H141 0.88(3)
C15 C16 1.375(2)
C15 C20 1.401(2)
C16 C17 1.384(3)
C16 H16 0.9300
C17 C18 1.387(3)
C17 H17 0.9300
C18 C19 1.388(3)
C19 C20 1.373(2)
C19 H19 0.9300
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
N1 H1 O4 . 0.96(2) 1.81(3) 2.766(2) 173(2)
N4 H4 O1 . 0.92(2) 1.91(2) 2.823(2) 172(2)
C4 H41 O3 1_445 0.92(4) 2.39(4) 3.231(4) 153(3)
C14 H141 O6 1_665 0.88(3) 2.51(3) 3.383(4) 169(3)
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
C10 N1 C1 O1 -177.65(19)
C10 N1 C1 N2 1.7(2)
C5 N2 C1 O1 177.68(18)
C2 N2 C1 O1 -1.5(3)
C5 N2 C1 N1 -1.7(2)
C2 N2 C1 N1 179.04(16)
C5 N2 C2 C3 -64.0(2)
C1 N2 C2 C3 115.0(2)
C1 N2 C5 C6 -178.67(19)
C2 N2 C5 C6 0.5(3)
C1 N2 C5 C10 1.1(2)
C2 N2 C5 C10 -179.73(17)
N2 C5 C6 C7 -179.67(18)
C10 C5 C6 C7 0.6(3)
C5 C6 C7 C8 -0.8(3)
C6 C7 C8 C9 0.4(3)
C6 C7 C8 N3 179.11(16)
O3 N3 C8 C7 172.97(18)
O2 N3 C8 C7 -8.4(3)
O3 N3 C8 C9 -8.3(3)
O2 N3 C8 C9 170.30(18)
C7 C8 C9 C10 0.1(3)
N3 C8 C9 C10 -178.55(15)
C8 C9 C10 N1 179.90(18)
C8 C9 C10 C5 -0.3(2)
C1 N1 C10 C9 178.72(19)
C1 N1 C10 C5 -1.1(2)
C6 C5 C10 C9 -0.1(3)
N2 C5 C10 C9 -179.84(15)
C6 C5 C10 N1 179.78(16)
N2 C5 C10 N1 0.01(19)
C20 N4 C11 O4 -179.86(18)
C20 N4 C11 N5 0.1(2)
C15 N5 C11 O4 -179.94(18)
C12 N5 C11 O4 3.2(3)
C15 N5 C11 N4 0.1(2)
C12 N5 C11 N4 -176.74(17)
C11 N5 C12 C13 -120.6(2)
C15 N5 C12 C13 63.0(3)
C11 N5 C15 C16 179.53(19)
C12 N5 C15 C16 -3.7(3)
C11 N5 C15 C20 -0.27(19)
C12 N5 C15 C20 176.45(17)
N5 C15 C16 C17 -179.89(18)
C20 C15 C16 C17 -0.1(3)
C15 C16 C17 C18 -0.2(3)
C16 C17 C18 C19 0.1(3)
C16 C17 C18 N6 -179.55(17)
O5 N6 C18 C19 175.1(2)
O6 N6 C18 C19 -4.0(3)
O5 N6 C18 C17 -5.2(3)
O6 N6 C18 C17 175.7(2)
C17 C18 C19 C20 0.2(3)
N6 C18 C19 C20 179.91(16)
C18 C19 C20 N4 179.50(18)
C18 C19 C20 C15 -0.5(2)
C11 N4 C20 C19 179.75(18)
C11 N4 C20 C15 -0.23(19)
C16 C15 C20 C19 0.5(3)
N5 C15 C20 C19 -179.68(15)
C16 C15 C20 N4 -179.52(16)
N5 C15 C20 N4 0.30(18)
