#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/45/2214562.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_2214562
loop_
_publ_author_name
'Huan-Mei Guo'
_publ_section_title
;
 N'-(4-Bromobenzylidene)propanohydrazide
;
_journal_coeditor_code           BX2094
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3461
_journal_page_last               o3461
_journal_paper_doi               10.1107/S1600536807032989
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H11 Br N2 O'
_chemical_formula_moiety         'C10 H11 Br N2 O'
_chemical_formula_sum            'C10 H11 Br N2 O'
_chemical_formula_weight         255.12
_chemical_name_systematic
;
N'-(4-Bromobenzylidene)propanohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.514(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7749(10)
_cell_length_b                   10.253(2)
_cell_length_c                   22.183(4)
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      1.84
_cell_volume                     1081.0(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5443
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    3.772
_exptl_absorpt_correction_T_max  0.6203
_exptl_absorpt_correction_T_min  0.4181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.343
_refine_ls_extinction_coef       0.0194(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1906
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0323
_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)+(0.0412P)²+0.4567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                1363
_reflns_number_total             1906
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bx2094.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214562
_cod_database_fobs_code          2214562
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br Br1 0.77061(8) 0.21453(4) 0.196101(18) 0.0605(2) Uani d . 1
N N1 -0.0531(6) 0.1549(3) 0.43391(13) 0.0441(7) Uani d . 1
O O1 -0.4993(5) 0.1484(3) 0.54910(11) 0.0573(7) Uani d . 1
N N2 -0.2420(6) 0.1110(3) 0.47212(13) 0.0471(8) Uani d . 1
H H2 -0.3080 0.0331 0.4679 0.057 Uiso calc R 1
C C1 0.3146(7) 0.2337(3) 0.34522(16) 0.0465(9) Uani d . 1
H H1 0.2713 0.2969 0.3729 0.056 Uiso calc R 1
C C2 0.4859(8) 0.2653(4) 0.30103(17) 0.0477(9) Uani d . 1
H H2A 0.5590 0.3491 0.2989 0.057 Uiso calc R 1
C C3 0.5480(7) 0.1711(4) 0.25989(15) 0.0429(9) Uani d . 1
C C4 0.4499(7) 0.0465(4) 0.26351(17) 0.0500(9) Uani d . 1
H H4 0.4975 -0.0166 0.2362 0.060 Uiso calc R 1
C C5 0.2792(7) 0.0152(4) 0.30818(16) 0.0501(10) Uani d . 1
H H5 0.2130 -0.0697 0.3109 0.060 Uiso calc R 1
C C6 0.2049(7) 0.1087(3) 0.34909(14) 0.0396(8) Uani d . 1
C C7 0.0139(7) 0.0733(3) 0.39412(15) 0.0427(8) Uani d . 1
H H7 -0.0606 -0.0105 0.3938 0.051 Uiso calc R 1
C C8 -0.3254(7) 0.1882(3) 0.51608(16) 0.0446(9) Uani d . 1
C C9 -0.1936(9) 0.3205(4) 0.5226(2) 0.0647(12) Uani d . 1
H H9A -0.2210 0.3649 0.4839 0.078 Uiso calc R 1
H H9B 0.0074 0.3101 0.5327 0.078 Uiso calc R 1
C C10 -0.3091(10) 0.4053(4) 0.5702(2) 0.0781(14) Uani d U 1
H H10A -0.2727 0.3648 0.6092 0.117 Uiso calc R 1
H H10B -0.5083 0.4158 0.5608 0.117 Uiso calc R 1
H H10C -0.2195 0.4892 0.5708 0.117 Uiso calc R 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
Br1 0.0552(3) 0.0728(4) 0.0571(3) -0.0027(2) 0.02439(19) 0.0049(2)
N1 0.0437(16) 0.0492(18) 0.0415(17) -0.0020(14) 0.0153(14) 0.0055(14)
O1 0.0602(16) 0.0590(17) 0.0574(16) -0.0039(14) 0.0288(14) 0.0030(13)
N2 0.0523(17) 0.0448(19) 0.0473(17) -0.0056(14) 0.0199(15) 0.0033(14)
C1 0.052(2) 0.042(2) 0.046(2) 0.0005(17) 0.0097(17) -0.0070(17)
C2 0.053(2) 0.039(2) 0.053(2) -0.0070(17) 0.0108(18) -0.0007(17)
C3 0.0373(18) 0.051(2) 0.041(2) 0.0030(16) 0.0108(16) 0.0058(16)
C4 0.056(2) 0.041(2) 0.056(2) 0.0054(18) 0.0200(18) -0.0042(18)
C5 0.053(2) 0.038(2) 0.062(2) -0.0045(17) 0.0194(19) -0.0004(18)
C6 0.0382(18) 0.042(2) 0.0391(19) 0.0023(16) 0.0053(15) 0.0014(16)
C7 0.0431(19) 0.041(2) 0.045(2) -0.0002(16) 0.0081(16) 0.0037(16)
C8 0.045(2) 0.047(2) 0.043(2) 0.0059(16) 0.0118(17) 0.0063(17)
C9 0.074(3) 0.053(3) 0.072(3) -0.006(2) 0.033(2) -0.007(2)
C10 0.083(3) 0.069(3) 0.087(3) -0.006(2) 0.030(3) -0.019(2)
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'
Br Br -0.2901 2.4595 '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 115.8(3)
C8 N2 N1 120.8(3)
C8 N2 H2 119.6
N1 N2 H2 119.6
C2 C1 C6 121.0(3)
C2 C1 H1 119.5
C6 C1 H1 119.5
C1 C2 C3 119.1(3)
C1 C2 H2A 120.4
C3 C2 H2A 120.4
C4 C3 C2 121.3(3)
C4 C3 Br1 118.8(3)
C2 C3 Br1 119.9(3)
C3 C4 C5 119.3(3)
C3 C4 H4 120.4
C5 C4 H4 120.4
C4 C5 C6 121.0(3)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 118.3(3)
C5 C6 C7 119.4(3)
C1 C6 C7 122.3(3)
N1 C7 C6 121.6(3)
N1 C7 H7 119.2
C6 C7 H7 119.2
O1 C8 N2 120.1(3)
O1 C8 C9 123.0(3)
N2 C8 C9 116.9(3)
C8 C9 C10 114.3(3)
C8 C9 H9A 108.7
C10 C9 H9A 108.7
C8 C9 H9B 108.7
C10 C9 H9B 108.7
H9A C9 H9B 107.6
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.903(3)
N1 C7 1.279(4)
N1 N2 1.372(3)
O1 C8 1.228(4)
N2 C8 1.346(4)
N2 H2 0.8600
C1 C2 1.374(5)
C1 C6 1.391(5)
C1 H1 0.9300
C2 C3 1.381(5)
C2 H2A 0.9300
C3 C4 1.366(5)
C4 C5 1.380(4)
C4 H4 0.9300
C5 C6 1.389(5)
C5 H5 0.9300
C6 C7 1.462(4)
C7 H7 0.9300
C8 C9 1.497(5)
C9 C10 1.513(5)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
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 O1 3_456 0.86 2.09 2.951(4) 174.0 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
C7 N1 N2 C8 179.4(3)
C6 C1 C2 C3 0.3(5)
C1 C2 C3 C4 -2.1(5)
C1 C2 C3 Br1 177.2(3)
C2 C3 C4 C5 1.8(6)
Br1 C3 C4 C5 -177.5(3)
C3 C4 C5 C6 0.4(5)
C4 C5 C6 C1 -2.1(5)
C4 C5 C6 C7 177.4(3)
C2 C1 C6 C5 1.8(5)
C2 C1 C6 C7 -177.7(3)
N2 N1 C7 C6 177.7(3)
C5 C6 C7 N1 177.7(3)
C1 C6 C7 N1 -2.8(5)
N1 N2 C8 O1 178.4(3)
N1 N2 C8 C9 -2.5(5)
O1 C8 C9 C10 -4.5(6)
N2 C8 C9 C10 176.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655288
2 PubChem 139072638
