#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230510.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_2230510
loop_
_publ_author_name
'Seidler, Tomasz'
'Gryl, Marlena'
'Trzewik, Bartosz'
'Stadnicka, Katarzyna'
_publ_section_title
;
 N-(5-Nitropyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide
;
_journal_coeditor_code           VM2095
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1507
_journal_paper_doi               10.1107/S1600536811018629
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H13 N5 O3'
_chemical_formula_moiety         'C19 H13 N5 O3'
_chemical_formula_sum            'C19 H13 N5 O3'
_chemical_formula_weight         359.34
_chemical_melting_point_gt       477
_chemical_melting_point_lt       478
_chemical_name_systematic
;N-(5-Nitropyridin-2-yl)-5H-
dibenzo[d,f][1,3]diazepine-6-carboxamide
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000
_cell_angle_beta                 100.6920(10)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   12.9702(2)
_cell_length_b                   9.21040(10)
_cell_length_c                   13.4145(2)
_cell_measurement_reflns_used    34515
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      44.4706
_cell_measurement_theta_min      2.9802
_cell_volume                     1574.68(4)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
'Mercury (Macrae et al., 2006) and ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), PARST (Nardelli, 1995) and
WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova Dual Cu at zero Atlas'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source
'Oxford Diffraction SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            127481
_diffrn_reflns_reduction_process
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.210
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4577
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0361
_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)+(0.0729P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                3784
_reflns_number_total             4577
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2095.cif
_cod_data_source_block           I
_cod_original_cell_volume        1574.68(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230510
_cod_database_fobs_code          2230510
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N2 0.15616(7) 0.02467(9) 0.92909(6) 0.01621(17) Uani d D 1 1 . .
H H2 0.1014(9) -0.0115(14) 0.9524(9) 0.019 Uiso d D 1 1 . .
C C3 0.14265(7) 0.16642(10) 0.90162(7) 0.01300(18) Uani d . 1 1 . .
N N3 0.20711(6) 0.25840(9) 0.87513(6) 0.01359(16) Uani d . 1 1 . .
C C4 0.03385(7) 0.22423(10) 0.90872(7) 0.01420(18) Uani d . 1 1 . .
O O4 -0.03207(5) 0.14658(8) 0.93589(6) 0.02028(17) Uani d . 1 1 . .
N N5 0.02224(6) 0.36682(9) 0.88352(6) 0.01523(17) Uani d D 1 1 . .
H H5 0.0796(9) 0.4033(13) 0.8674(9) 0.018 Uiso d D 1 1 . .
C C21 0.31624(7) 0.23319(10) 0.88312(7) 0.01323(18) Uani d . 1 1 . .
C C22 0.37511(8) 0.36134(11) 0.89410(7) 0.0173(2) Uani d . 1 1 . .
H H22 0.3397 0.4520 0.8913 0.021 Uiso calc R 1 1 . .
C C23 0.48377(8) 0.35967(12) 0.90890(8) 0.0207(2) Uani d . 1 1 . .
H H23 0.5223 0.4479 0.9161 0.025 Uiso calc R 1 1 . .
C C24 0.53540(8) 0.22716(12) 0.91305(8) 0.0202(2) Uani d . 1 1 . .
H H24 0.6099 0.2239 0.9260 0.024 Uiso calc R 1 1 . .
C C25 0.47790(7) 0.09954(11) 0.89823(7) 0.0172(2) Uani d . 1 1 . .
H H25 0.5143 0.0098 0.8995 0.021 Uiso calc R 1 1 . .
C C26 0.36771(7) 0.09835(10) 0.88136(7) 0.01375(18) Uani d . 1 1 . .
C C31 0.21410(7) -0.07550(10) 0.88061(7) 0.01417(18) Uani d . 1 1 . .
C C32 0.16781(8) -0.21063(11) 0.85663(8) 0.0187(2) Uani d . 1 1 . .
H H32 0.1011 -0.2310 0.8730 0.022 Uiso calc R 1 1 . .
C C33 0.21824(9) -0.31577(11) 0.80897(8) 0.0219(2) Uani d . 1 1 . .
H H33 0.1863 -0.4078 0.7930 0.026 Uiso calc R 1 1 . .
C C34 0.31554(9) -0.28566(11) 0.78484(8) 0.0218(2) Uani d . 1 1 . .
H H34 0.3509 -0.3571 0.7527 0.026 Uiso calc R 1 1 . .
C C35 0.36072(8) -0.15065(11) 0.80807(8) 0.0181(2) Uani d . 1 1 . .
H H35 0.4267 -0.1305 0.7900 0.022 Uiso calc R 1 1 . .
C C36 0.31255(7) -0.04244(10) 0.85732(7) 0.01404(18) Uani d . 1 1 . .
N N51 -0.04575(6) 0.59431(9) 0.85591(6) 0.01663(18) Uani d . 1 1 . .
C C52 -0.12294(8) 0.69109(11) 0.85240(7) 0.01701(19) Uani d . 1 1 . .
H H52 -0.1109 0.7889 0.8352 0.020 Uiso calc R 1 1 . .
C C53 -0.21986(8) 0.65325(11) 0.87304(7) 0.01609(19) Uani d . 1 1 . .
C C54 -0.23889(8) 0.51174(11) 0.90003(8) 0.0181(2) Uani d . 1 1 . .
H H54 -0.3054 0.4849 0.9143 0.022 Uiso calc R 1 1 . .
C C55 -0.15953(7) 0.41067(11) 0.90574(8) 0.01687(19) Uani d . 1 1 . .
H H55 -0.1691 0.3131 0.9251 0.020 Uiso calc R 1 1 . .
C C56 -0.06433(7) 0.45741(10) 0.88190(7) 0.01390(18) Uani d . 1 1 . .
N N57 -0.30275(7) 0.76288(10) 0.86450(7) 0.02042(19) Uani d . 1 1 . .
O O58 -0.39181(6) 0.72147(10) 0.86834(7) 0.0296(2) Uani d . 1 1 . .
O O59 -0.27849(7) 0.89005(9) 0.85351(7) 0.02897(19) Uani 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N2 C31 . . 123.51(8) ?
C3 N2 H2 . . 112.5(8) ?
C31 N2 H2 . . 116.2(8) ?
N3 C3 N2 . . 130.55(9) ?
N3 C3 C4 . . 116.30(8) ?
N2 C3 C4 . . 113.09(8) ?
C3 N3 C21 . . 124.20(8) ?
O4 C4 N5 . . 126.12(9) ?
O4 C4 C3 . . 121.37(8) ?
N5 C4 C3 . . 112.50(8) ?
C4 N5 C56 . . 129.34(8) ?
C4 N5 H5 . . 111.8(8) ?
C56 N5 H5 . . 118.9(8) ?
C22 C21 C26 . . 119.56(8) ?
C22 C21 N3 . . 112.79(8) ?
C26 C21 N3 . . 127.65(8) ?
C23 C22 C21 . . 121.75(9) ?
C23 C22 H22 . . 119.1 ?
C21 C22 H22 . . 119.1 ?
C22 C23 C24 . . 119.05(9) ?
C22 C23 H23 . . 120.5 ?
C24 C23 H23 . . 120.5 ?
C25 C24 C23 . . 119.80(9) ?
C25 C24 H24 . . 120.1 ?
C23 C24 H24 . . 120.1 ?
C24 C25 C26 . . 122.26(9) ?
C24 C25 H25 . . 118.9 ?
C26 C25 H25 . . 118.9 ?
C25 C26 C21 . . 117.41(9) ?
C25 C26 C36 . . 118.41(8) ?
C21 C26 C36 . . 124.09(8) ?
C32 C31 C36 . . 120.89(9) ?
C32 C31 N2 . . 116.34(8) ?
C36 C31 N2 . . 122.77(9) ?
C33 C32 C31 . . 120.63(9) ?
C33 C32 H32 . . 119.7 ?
C31 C32 H32 . . 119.7 ?
C34 C33 C32 . . 119.62(10) ?
C34 C33 H33 . . 120.2 ?
C32 C33 H33 . . 120.2 ?
C35 C34 C33 . . 119.47(9) ?
C35 C34 H34 . . 120.3 ?
C33 C34 H34 . . 120.3 ?
C34 C35 C36 . . 122.42(9) ?
C34 C35 H35 . . 118.8 ?
C36 C35 H35 . . 118.8 ?
C31 C36 C35 . . 116.95(9) ?
C31 C36 C26 . . 124.20(8) ?
C35 C36 C26 . . 118.85(8) ?
C52 N51 C56 . . 117.84(8) ?
N51 C52 C53 . . 121.94(9) ?
N51 C52 H52 . . 119.0 ?
C53 C52 H52 . . 119.0 ?
C52 C53 C54 . . 120.14(9) ?
C52 C53 N57 . . 119.53(9) ?
C54 C53 N57 . . 120.33(9) ?
C55 C54 C53 . . 118.79(9) ?
C55 C54 H54 . . 120.6 ?
C53 C54 H54 . . 120.6 ?
C54 C55 C56 . . 117.43(9) ?
C54 C55 H55 . . 121.3 ?
C56 C55 H55 . . 121.3 ?
N51 C56 N5 . . 112.52(8) ?
N51 C56 C55 . . 123.85(9) ?
N5 C56 C55 . . 123.63(9) ?
O58 N57 O59 . . 124.44(9) ?
O58 N57 C53 . . 117.77(9) ?
O59 N57 C53 . . 117.79(9) ?
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
N2 C3 . 1.3591(12) ?
N2 C31 . 1.4213(12) ?
N2 H2 . 0.892(11) ?
C3 N3 . 1.2858(12) ?
C3 C4 . 1.5276(13) ?
N3 C21 . 1.4186(12) ?
C4 O4 . 1.2211(11) ?
C4 N5 . 1.3575(12) ?
N5 C56 . 1.3958(12) ?
N5 H5 . 0.879(11) ?
C21 C22 . 1.3987(13) ?
C21 C26 . 1.4122(13) ?
C22 C23 . 1.3864(14) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.3883(15) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.3864(14) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.4050(13) ?
C25 H25 . 0.9500 ?
C26 C36 . 1.4872(13) ?
C31 C32 . 1.3933(13) ?
C31 C36 . 1.4031(13) ?
C32 C33 . 1.3891(14) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.3878(15) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.3853(15) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.4048(13) ?
C35 H35 . 0.9500 ?
N51 C52 . 1.3348(13) ?
N51 C56 . 1.3419(12) ?
C52 C53 . 1.3812(14) ?
C52 H52 . 0.9500 ?
C53 C54 . 1.3870(14) ?
C53 N57 . 1.4639(13) ?
C54 C55 . 1.3794(13) ?
C54 H54 . 0.9500 ?
C55 C56 . 1.3996(13) ?
C55 H55 . 0.9500 ?
N57 O58 . 1.2265(12) ?
N57 O59 . 1.2288(13) ?
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
_geom_hbond_publ_flag
N2 H2 O4 . 0.890(10) 2.240(10) 2.7041(11) 112.0(10) y
N2 H2 O4 3_557 0.890(10) 2.260(10) 3.0725(11) 152.0(10) y
N5 H5 N3 . 0.880(10) 2.110(10) 2.6191(11) 116.0(10) y
C55 H55 O4 . 0.95 2.33 2.9266(12) 120 y
C32 H32 N51 1_545 0.95 2.47 3.3000(13) 146 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C31 N2 C3 N3 . . . . -40.22(16) ?
C31 N2 C3 C4 . . . . 142.83(9) ?
N2 C3 N3 C21 . . . . -9.51(16) ?
C4 C3 N3 C21 . . . . 167.36(8) ?
N3 C3 C4 O4 . . . . -177.99(9) ?
N2 C3 C4 O4 . . . . -0.58(13) ?
N3 C3 C4 N5 . . . . 1.05(12) ?
N2 C3 C4 N5 . . . . 178.47(8) ?
O4 C4 N5 C56 . . . . -0.22(17) ?
C3 C4 N5 C56 . . . . -179.21(9) ?
C3 N3 C21 C22 . . . . -153.01(9) ?
C3 N3 C21 C26 . . . . 26.82(15) ?
C26 C21 C22 C23 . . . . -3.56(15) ?
N3 C21 C22 C23 . . . . 176.28(9) ?
C21 C22 C23 C24 . . . . -0.09(15) ?
C22 C23 C24 C25 . . . . 2.66(15) ?
C23 C24 C25 C26 . . . . -1.61(15) ?
C24 C25 C26 C21 . . . . -1.98(14) ?
C24 C25 C26 C36 . . . . 174.74(9) ?
C22 C21 C26 C25 . . . . 4.48(13) ?
N3 C21 C26 C25 . . . . -175.34(9) ?
C22 C21 C26 C36 . . . . -172.04(9) ?
N3 C21 C26 C36 . . . . 8.14(15) ?
C3 N2 C31 C32 . . . . -134.33(10) ?
C3 N2 C31 C36 . . . . 45.58(14) ?
C36 C31 C32 C33 . . . . -0.04(15) ?
N2 C31 C32 C33 . . . . 179.87(10) ?
C31 C32 C33 C34 . . . . -0.14(16) ?
C32 C33 C34 C35 . . . . -0.43(16) ?
C33 C34 C35 C36 . . . . 1.23(16) ?
C32 C31 C36 C35 . . . . 0.77(14) ?
N2 C31 C36 C35 . . . . -179.14(9) ?
C32 C31 C36 C26 . . . . -179.29(9) ?
N2 C31 C36 C26 . . . . 0.80(14) ?
C34 C35 C36 C31 . . . . -1.38(14) ?
C34 C35 C36 C26 . . . . 178.68(9) ?
C25 C26 C36 C31 . . . . 151.43(9) ?
C21 C26 C36 C31 . . . . -32.08(14) ?
C25 C26 C36 C35 . . . . -28.63(13) ?
C21 C26 C36 C35 . . . . 147.86(9) ?
C56 N51 C52 C53 . . . . -0.98(14) ?
N51 C52 C53 C54 . . . . 1.09(15) ?
N51 C52 C53 N57 . . . . -177.84(9) ?
C52 C53 C54 C55 . . . . 0.01(15) ?
N57 C53 C54 C55 . . . . 178.94(9) ?
C53 C54 C55 C56 . . . . -1.11(14) ?
C52 N51 C56 N5 . . . . -179.63(8) ?
C52 N51 C56 C55 . . . . -0.22(15) ?
C4 N5 C56 N51 . . . . 177.97(9) ?
C4 N5 C56 C55 . . . . -1.44(16) ?
C54 C55 C56 N51 . . . . 1.27(15) ?
C54 C55 C56 N5 . . . . -179.39(9) ?
C52 C53 N57 O58 . . . . 169.30(9) ?
C54 C53 N57 O58 . . . . -9.64(14) ?
C52 C53 N57 O59 . . . . -10.38(14) ?
C54 C53 N57 O59 . . . . 170.68(9) ?
