#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/68/2226868.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_2226868
loop_
_publ_author_name
'Hussain, Abid'
'Shafiq, Zahid'
'Tahir, M. Nawaz'
'Yaqub, Muhammad'
_publ_section_title
;
 N'-[(E)-(1-Methyl-1H-pyrrol-2-yl)methylidene]benzohydrazide
;
_journal_coeditor_code           GK2289
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1888
_journal_paper_doi               10.1107/S1600536810025390
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H13 N3 O'
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_chemical_name_systematic
;
N'-[(E)-(1-Methyl-1H-pyrrol-2-yl)methylidene]benzohydrazide
benzohydrazide
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 110.241(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1170(8)
_cell_length_b                   11.6329(9)
_cell_length_c                   9.6735(6)
_cell_measurement_reflns_used    1770
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.62
_cell_volume                     1173.75(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.50
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11164
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.165
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0555P)²+0.1600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1388
_reflns_number_gt                1770
_reflns_number_total             2930
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2289.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226868
_cod_database_fobs_code          2226868
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.71496(14) 0.18682(11) 0.12223(13) 0.0554(5) Uani . . 1.000
N N1 0.75685(15) 0.26311(12) 0.34764(15) 0.0431(5) Uani . . 1.000
N N2 0.80816(15) 0.36186(12) 0.30879(16) 0.0442(5) Uani . . 1.000
N N3 0.93230(15) 0.58927(13) 0.29335(16) 0.0457(5) Uani . . 1.000
C C1 0.66632(16) 0.07206(14) 0.29906(18) 0.0394(5) Uani . . 1.000
C C2 0.67749(19) 0.05014(16) 0.4433(2) 0.0492(7) Uani . . 1.000
C C3 0.6323(2) -0.05186(18) 0.4795(2) 0.0602(8) Uani . . 1.000
C C4 0.5752(2) -0.13174(18) 0.3738(3) 0.0639(8) Uani . . 1.000
C C5 0.5635(2) -0.11093(19) 0.2302(3) 0.0695(9) Uani . . 1.000
C C6 0.6095(2) -0.01047(18) 0.1927(2) 0.0565(7) Uani . . 1.000
C C7 0.71456(16) 0.17851(14) 0.24946(19) 0.0389(6) Uani . . 1.000
C C8 0.80671(18) 0.44929(15) 0.38773(19) 0.0454(6) Uani . . 1.000
C C9 0.85533(18) 0.56059(15) 0.37314(19) 0.0445(6) Uani . . 1.000
C C10 0.8295(2) 0.66046(17) 0.4330(2) 0.0592(8) Uani . . 1.000
C C11 0.8898(2) 0.75049(18) 0.3880(3) 0.0657(9) Uani . . 1.000
C C12 0.9521(2) 0.70430(16) 0.3038(2) 0.0563(7) Uani . . 1.000
C C13 0.9916(2) 0.51144(17) 0.2185(2) 0.0562(8) Uani . . 1.000
H H1 0.75240 0.25659 0.43429 0.0517 Uiso . . 1.000
H H2 0.71552 0.10422 0.51611 0.0591 Uiso . . 1.000
H H3 0.64097 -0.06633 0.57704 0.0723 Uiso . . 1.000
H H4 0.54425 -0.19993 0.39907 0.0767 Uiso . . 1.000
H H5 0.52429 -0.16507 0.15793 0.0833 Uiso . . 1.000
H H6 0.60254 0.00238 0.09532 0.0679 Uiso . . 1.000
H H8 0.77103 0.43980 0.46091 0.0545 Uiso . . 1.000
H H10 0.78019 0.66688 0.49312 0.0711 Uiso . . 1.000
H H11 0.88753 0.82779 0.41155 0.0788 Uiso . . 1.000
H H12 1.00108 0.74519 0.25975 0.0676 Uiso . . 1.000
H H13A 1.05186 0.55310 0.18654 0.0843 Uiso . . 1.000
H H13B 0.92678 0.47841 0.13455 0.0843 Uiso . . 1.000
H H13C 1.03550 0.45137 0.28485 0.0843 Uiso . . 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C7 . . . 119.54(14) no
N1 N2 C8 . . . 113.93(16) no
C9 N3 C12 . . . 108.30(16) no
C9 N3 C13 . . . 127.28(16) no
C12 N3 C13 . . . 124.28(17) no
N2 N1 H1 . . . 120.00 no
C7 N1 H1 . . . 120.00 no
C6 C1 C7 . . . 117.20(15) no
C2 C1 C6 . . . 118.66(17) no
C2 C1 C7 . . . 124.13(16) no
C1 C2 C3 . . . 120.11(17) no
C2 C3 C4 . . . 120.73(19) no
C3 C4 C5 . . . 119.7(2) no
C4 C5 C6 . . . 120.3(2) no
C1 C6 C5 . . . 120.52(19) no
N1 C7 C1 . . . 117.39(15) no
O1 C7 N1 . . . 121.93(16) no
O1 C7 C1 . . . 120.68(15) no
N2 C8 C9 . . . 125.45(18) no
N3 C9 C10 . . . 107.02(16) no
C8 C9 C10 . . . 125.74(19) no
N3 C9 C8 . . . 127.20(17) no
C9 C10 C11 . . . 108.14(19) no
C10 C11 C12 . . . 107.00(19) no
N3 C12 C11 . . . 109.53(19) no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
N2 C8 H8 . . . 117.00 no
C9 C8 H8 . . . 117.00 no
C9 C10 H10 . . . 126.00 no
C11 C10 H10 . . . 126.00 no
C10 C11 H11 . . . 126.00 no
C12 C11 H11 . . . 127.00 no
N3 C12 H12 . . . 125.00 no
C11 C12 H12 . . . 125.00 no
N3 C13 H13A . . . 109.00 no
N3 C13 H13B . . . 110.00 no
N3 C13 H13C . . . 110.00 no
H13A C13 H13B . . . 109.00 no
H13A C13 H13C . . . 109.00 no
H13B C13 H13C . . . 109.00 no
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 C7 . . 1.236(2) no
N1 N2 . . 1.391(2) no
N1 C7 . . 1.335(2) no
N2 C8 . . 1.275(2) no
N3 C9 . . 1.377(3) no
N3 C12 . . 1.354(2) no
N3 C13 . . 1.452(3) no
N1 H1 . . 0.8600 no
C1 C2 . . 1.381(2) no
C1 C7 . . 1.493(2) no
C1 C6 . . 1.389(3) no
C2 C3 . . 1.380(3) no
C3 C4 . . 1.365(3) no
C4 C5 . . 1.371(4) no
C5 C6 . . 1.374(3) no
C8 C9 . . 1.429(3) no
C9 C10 . . 1.372(3) no
C10 C11 . . 1.392(3) no
C11 C12 . . 1.350(3) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C8 H8 . . 0.9300 no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13A . . 0.9600 no
C13 H13B . . 0.9600 no
C13 H13C . . 0.9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N2 2.6801(19) . . no
O1 N1 2.910(2) . 4_554 no
O1 C8 3.209(2) . 4_554 no
O1 H6 2.4500 . . no
O1 H1 2.1100 . 4_554 no
O1 H2 2.6400 . 4_554 no
O1 H8 2.3800 . 4_554 no
N1 O1 2.910(2) . 4_555 no
N2 N3 3.011(2) . . no
N2 O1 2.6801(19) . . no
N2 C13 3.030(3) . . no
N3 N2 3.011(2) . . no
N1 H2 2.6100 . . no
N2 H13B 2.8200 . . no
N2 H12 2.7800 . 2_745 no
N2 H2 2.6900 . 4_554 no
N2 H13C 2.8200 . . no
C3 C3 3.328(3) . 3_656 no
C8 O1 3.209(2) . 4_555 no
C9 C9 3.591(3) . 3_766 no
C11 C13 3.599(3) . 2_755 no
C13 C11 3.599(3) . 2_745 no
C13 N2 3.030(3) . . no
C1 H13A 3.1000 . 2_745 no
C2 H13B 2.7700 . 4_555 no
C2 H1 2.5500 . . no
C6 H6 2.9600 . 3_655 no
C7 H13A 2.8500 . 2_745 no
C7 H4 3.0800 . 2_655 no
C8 H13C 3.0400 . . no
C9 H3 3.0300 . 4_554 no
C10 H13C 2.9300 . 3_766 no
C12 H13C 3.0200 . 2_755 no
C13 H11 3.0200 . 2_745 no
H1 C2 2.5500 . . no
H1 H2 2.0400 . . no
H1 H8 2.1500 . . no
H1 O1 2.1100 . 4_555 no
H2 N1 2.6100 . . no
H2 H1 2.0400 . . no
H2 O1 2.6400 . 4_555 no
H2 N2 2.6900 . 4_555 no
H2 H13B 2.4300 . 4_555 no
H3 C9 3.0300 . 4_555 no
H4 C7 3.0800 . 2_645 no
H6 O1 2.4500 . . no
H6 C6 2.9600 . 3_655 no
H6 H6 2.3900 . 3_655 no
H8 H1 2.1500 . . no
H8 O1 2.3800 . 4_555 no
H11 C13 3.0200 . 2_755 no
H12 H13A 2.4700 . . no
H12 N2 2.7800 . 2_755 no
H12 H13C 2.4500 . 2_755 no
H13A H12 2.4700 . . no
H13A C1 3.1000 . 2_755 no
H13A C7 2.8500 . 2_755 no
H13B N2 2.8200 . . no
H13B C2 2.7700 . 4_554 no
H13B H2 2.4300 . 4_554 no
H13C N2 2.8200 . . no
H13C C8 3.0400 . . no
H13C C12 3.0200 . 2_745 no
H13C H12 2.4500 . 2_745 no
H13C C10 2.9300 . 3_766 no
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
N1 H1 O1 4_555 0.86 2.11 2.910(2) 155 yes
C8 H8 O1 4_555 0.93 2.38 3.209(2) 148 yes
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
C7 N1 N2 C8 . . . . 158.43(18) no
N2 N1 C7 O1 . . . . -2.8(3) no
N2 N1 C7 C1 . . . . 177.08(16) no
N1 N2 C8 C9 . . . . 178.86(18) no
C12 N3 C9 C8 . . . . 177.51(19) no
C12 N3 C9 C10 . . . . -0.4(2) no
C13 N3 C9 C8 . . . . -6.7(3) no
C13 N3 C9 C10 . . . . 175.43(18) no
C9 N3 C12 C11 . . . . -0.1(2) no
C13 N3 C12 C11 . . . . -176.05(19) no
C6 C1 C2 C3 . . . . -0.2(3) no
C7 C1 C2 C3 . . . . -178.67(19) no
C2 C1 C6 C5 . . . . 1.1(3) no
C7 C1 C6 C5 . . . . 179.6(2) no
C2 C1 C7 O1 . . . . 171.48(19) no
C2 C1 C7 N1 . . . . -8.4(3) no
C6 C1 C7 O1 . . . . -7.0(3) no
C6 C1 C7 N1 . . . . 173.11(18) no
C1 C2 C3 C4 . . . . -0.6(3) no
C2 C3 C4 C5 . . . . 0.5(4) no
C3 C4 C5 C6 . . . . 0.3(4) no
C4 C5 C6 C1 . . . . -1.1(4) no
N2 C8 C9 N3 . . . . -13.0(3) no
N2 C8 C9 C10 . . . . 164.5(2) no
N3 C9 C10 C11 . . . . 0.7(2) no
C8 C9 C10 C11 . . . . -177.2(2) no
C9 C10 C11 C12 . . . . -0.7(3) no
C10 C11 C12 N3 . . . . 0.5(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7963727
