#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/22/2232282.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_2232282
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chia, Tze Shyang'
'Malladi, Shridhar'
'Isloor, Arun M.'
'Shivananda, Kammasandra N.'
_publ_section_title
;
 (2E)-2-(4-Fluorobenzylidene)hydrazinecarboxamide
;
_journal_coeditor_code           HB6436
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2885
_journal_page_last               o2886
_journal_paper_doi               10.1107/S1600536811040797
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H8 F N3 O'
_chemical_formula_moiety         'C8 H8 F N3 O'
_chemical_formula_sum            'C8 H8 F N3 O'
_chemical_formula_weight         181.17
_chemical_name_systematic
;
(2E)-2-(4-Fluorobenzylidene)hydrazinecarboxamide
;
_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                90.00
_cell_angle_beta                 103.478(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.522(2)
_cell_length_b                   4.4381(6)
_cell_length_c                   11.9457(15)
_cell_measurement_reflns_used    2666
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.39
_cell_measurement_theta_min      2.54
_cell_volume                     851.81(19)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX DUO CCD'
_diffrn_measurement_method       'φ and 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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8746
_diffrn_reflns_theta_full        29.89
_diffrn_reflns_theta_max         29.89
_diffrn_reflns_theta_min         1.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0532
_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)+(0.1446P)²+0.0418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.2085
_reflns_number_gt                1657
_reflns_number_total             2418
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6436.cif
_cod_data_source_block           I
_cod_original_cell_volume        851.80(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232282
_cod_database_fobs_code          2232282
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
F F1 0.51936(9) 1.2636(4) 1.15848(18) 0.1170(6) Uani d . 1 1
O O1 1.01013(7) 0.7059(3) 0.87156(9) 0.0508(3) Uani d . 1 1
N N1 0.83497(7) 0.8821(3) 0.97516(10) 0.0448(3) Uani d . 1 1
N N2 0.90494(8) 0.7354(3) 0.96093(11) 0.0470(3) Uani d . 1 1
N N3 0.91237(8) 1.0690(3) 0.81619(11) 0.0493(4) Uani d . 1 1
C C1 0.71134(11) 0.8578(5) 1.18840(15) 0.0637(5) Uani d . 1 1
H H1A 0.7461 0.7333 1.2413 0.076 Uiso calc R 1 1
C C2 0.63885(11) 0.9701(6) 1.21288(16) 0.0705(5) Uani d . 1 1
H H2A 0.6244 0.9217 1.2814 0.085 Uiso calc R 1 1
C C3 0.58977(12) 1.1518(5) 1.1342(2) 0.0740(6) Uani d . 1 1
C C4 0.60851(13) 1.2285(6) 1.0325(2) 0.0855(7) Uani d . 1 1
H H4A 0.5735 1.3543 0.9805 0.103 Uiso calc R 1 1
C C5 0.68021(11) 1.1161(5) 1.00849(17) 0.0669(5) Uani d . 1 1
H H5A 0.6937 1.1662 0.9394 0.080 Uiso calc R 1 1
C C6 0.73235(9) 0.9300(4) 1.08559(13) 0.0493(4) Uani d . 1 1
C C7 0.80796(9) 0.8014(4) 1.06141(13) 0.0504(4) Uani d . 1 1
H H7A 0.8371 0.6560 1.1109 0.060 Uiso calc R 1 1
C C8 0.94581(8) 0.8362(3) 0.88136(11) 0.0405(3) Uani d . 1 1
H H1N3 0.9423(12) 1.145(5) 0.7725(18) 0.064(5) Uiso d . 1 1
H H1N2 0.9306(12) 0.599(5) 1.0133(16) 0.061(5) Uiso d . 1 1
H H2N3 0.8717(14) 1.181(5) 0.8357(19) 0.074(6) Uiso d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 0.0854(10) 0.1393(14) 0.1524(15) 0.0374(9) 0.0807(10) 0.0080(10)
O1 0.0544(6) 0.0586(7) 0.0499(6) 0.0023(4) 0.0334(5) -0.0022(4)
N1 0.0447(6) 0.0544(7) 0.0417(6) 0.0019(5) 0.0228(5) -0.0006(5)
N2 0.0490(7) 0.0566(7) 0.0446(7) 0.0073(5) 0.0296(5) 0.0048(5)
N3 0.0569(7) 0.0541(7) 0.0457(7) -0.0004(5) 0.0299(6) 0.0032(5)
C1 0.0563(9) 0.0936(13) 0.0502(9) 0.0081(8) 0.0304(7) 0.0076(8)
C2 0.0662(10) 0.0974(15) 0.0620(10) -0.0021(9) 0.0438(9) -0.0068(10)
C3 0.0558(10) 0.0863(14) 0.0938(15) 0.0098(8) 0.0457(10) -0.0057(11)
C4 0.0695(12) 0.1019(16) 0.0965(17) 0.0321(11) 0.0423(12) 0.0232(13)
C5 0.0631(10) 0.0820(12) 0.0656(11) 0.0196(8) 0.0353(8) 0.0179(9)
C6 0.0457(7) 0.0643(9) 0.0448(7) 0.0019(6) 0.0244(6) -0.0001(6)
C7 0.0482(8) 0.0673(9) 0.0425(8) 0.0090(6) 0.0245(6) 0.0085(6)
C8 0.0461(7) 0.0452(7) 0.0361(6) -0.0067(5) 0.0215(5) -0.0085(5)
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'
F F 0.0171 0.0103 '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
C7 N1 N2 115.71(12)
C8 N2 N1 119.96(12)
C8 N2 H1N2 118.4(12)
N1 N2 H1N2 120.3(12)
C8 N3 H1N3 115.9(13)
C8 N3 H2N3 120.3(14)
H1N3 N3 H2N3 120(2)
C2 C1 C6 120.56(17)
C2 C1 H1A 119.7
C6 C1 H1A 119.7
C3 C2 C1 118.24(16)
C3 C2 H2A 120.9
C1 C2 H2A 120.9
F1 C3 C2 118.27(19)
F1 C3 C4 118.9(2)
C2 C3 C4 122.86(16)
C3 C4 C5 118.7(2)
C3 C4 H4A 120.6
C5 C4 H4A 120.6
C4 C5 C6 120.79(17)
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C5 C6 C1 118.85(14)
C5 C6 C7 122.08(14)
C1 C6 C7 119.06(15)
N1 C7 C6 121.99(14)
N1 C7 H7A 119.0
C6 C7 H7A 119.0
O1 C8 N3 123.66(12)
O1 C8 N2 119.18(13)
N3 C8 N2 117.15(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C3 1.3568(19)
O1 C8 1.2393(16)
N1 C7 1.2661(18)
N1 N2 1.3714(16)
N2 C8 1.3634(17)
N2 H1N2 0.90(2)
N3 C8 1.3333(18)
N3 H1N3 0.87(2)
N3 H2N3 0.91(2)
C1 C2 1.390(2)
C1 C6 1.389(2)
C1 H1A 0.9300
C2 C3 1.355(3)
C2 H2A 0.9300
C3 C4 1.365(3)
C4 C5 1.376(2)
C4 H4A 0.9300
C5 C6 1.379(2)
C5 H5A 0.9300
C6 C7 1.4621(19)
C7 H7A 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
_geom_hbond_publ_flag
N3 H1N3 O1 2_756 0.88(2) 2.07(2) 2.8954(19) 158(2) yes
N2 H1N2 O1 3_767 0.92(2) 2.00(2) 2.9155(19) 179(2) 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
C7 N1 N2 C8 -170.19(13)
C6 C1 C2 C3 -0.3(3)
C1 C2 C3 F1 -179.4(2)
C1 C2 C3 C4 0.0(4)
F1 C3 C4 C5 179.6(2)
C2 C3 C4 C5 0.2(4)
C3 C4 C5 C6 -0.1(4)
C4 C5 C6 C1 -0.1(3)
C4 C5 C6 C7 178.57(19)
C2 C1 C6 C5 0.3(3)
C2 C1 C6 C7 -178.40(17)
N2 N1 C7 C6 -177.87(13)
C5 C6 C7 N1 8.7(3)
C1 C6 C7 N1 -172.65(16)
N1 N2 C8 O1 178.19(12)
N1 N2 C8 N3 -3.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7919084
