#------------------------------------------------------------------------------
#$Date: 2016-06-17 03:46:08 +0200 (vie 17 de jun de 2016) $
#$Revision: 183621 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/34/1543456.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_1543456
loop_
_publ_author_name
'Karrouchi, Khalid'
'Ramli, Youssef'
'Taoufik, Jamal'
'Radi, Smaail'
'Ansar, Mhammed'
'Mague, Joel T.'
_publ_section_title
;
 N'-[(1E)-4-Bromobenzylidene]-5-phenyl-1H-pyrazole-3-carbohydrazide
;
_journal_coeditor_code           HB4044
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x160830
_journal_paper_doi               10.1107/S2414314616008300
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C17 H13 Br N4 O'
_chemical_formula_moiety         'C17 H13 Br N4 O'
_chemical_formula_sum            'C17 H13 Br N4 O'
_chemical_formula_weight         369.22
_chemical_name_systematic
N'-[(1E)-4-Bromobenzylidene]-5-phenyl-1H-pyrazole-3-carbohydrazide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.0720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5151(3)
_cell_length_b                   7.17520(10)
_cell_length_c                   14.4593(3)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.0829
_cell_measurement_theta_min      3.0325
_cell_volume                     1511.90(5)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT  (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19026
_diffrn_reflns_theta_full        72.000
_diffrn_reflns_theta_max         72.077
_diffrn_reflns_theta_min         3.032
_exptl_absorpt_coefficient_mu    3.792
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.419
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0406P)²+1.1336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                2704
_reflns_number_total             2958
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4044sup1.cif
_cod_data_source_block           I
_cod_database_code               1543456
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.518
_shelx_estimated_absorpt_t_max   0.928
loop_
_space_group_symop_operation_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_occupancy
Br Br1 0.08242(2) 1.44181(3) 0.40787(2) 0.03152(10) Uani d 1
O O1 0.55572(10) 0.7240(2) 0.39651(12) 0.0274(3) Uani d 1
N N1 0.56205(12) 0.1066(2) 0.36792(13) 0.0209(3) Uani d 1
H H1A 0.548(2) -0.014(4) 0.372(2) 0.037(7) Uiso d 1
N N2 0.50212(11) 0.2396(2) 0.37161(12) 0.0207(3) Uani d 1
N N3 0.41822(12) 0.5828(2) 0.37237(13) 0.0208(3) Uani d 1
H H3A 0.3856(19) 0.477(4) 0.3598(19) 0.029(7) Uiso d 1
N N4 0.37729(12) 0.7495(2) 0.37822(12) 0.0216(3) Uani d 1
C C1 0.72343(14) 0.0664(3) 0.36873(14) 0.0201(4) Uani d 1
C C2 0.81039(14) 0.1483(3) 0.40431(15) 0.0248(4) Uani d 1
H H2 0.8169 0.2714 0.4300 0.030 Uiso calc 1
C C3 0.88713(15) 0.0518(3) 0.40256(17) 0.0300(5) Uani d 1
H H3 0.9459 0.1090 0.4271 0.036 Uiso calc 1
C C4 0.87849(15) -0.1286(3) 0.36503(16) 0.0289(5) Uani d 1
H H4 0.9311 -0.1948 0.3637 0.035 Uiso calc 1
C C5 0.79246(15) -0.2107(3) 0.32966(15) 0.0254(4) Uani d 1
H H5 0.7863 -0.3337 0.3039 0.030 Uiso calc 1
C C6 0.71507(14) -0.1153(3) 0.33133(15) 0.0219(4) Uani d 1
H H6 0.6565 -0.1733 0.3071 0.026 Uiso calc 1
C C7 0.64455(13) 0.1770(3) 0.37096(14) 0.0196(4) Uani d 1
C C8 0.63687(14) 0.3686(3) 0.37568(15) 0.0208(4) Uani d 1
H H8 0.6821 0.4596 0.3781 0.025 Uiso calc 1
C C9 0.54810(14) 0.3990(3) 0.37609(15) 0.0194(4) Uani d 1
C C10 0.50863(14) 0.5828(3) 0.38258(14) 0.0198(4) Uani d 1
C C11 0.28977(14) 0.7463(3) 0.35493(15) 0.0218(4) Uani d 1
H H11 0.2566 0.6344 0.3322 0.026 Uiso calc 1
C C12 0.24174(14) 0.9165(3) 0.36375(14) 0.0207(4) Uani d 1
C C13 0.14574(14) 0.9207(3) 0.32523(15) 0.0226(4) Uani d 1
H H13 0.1129 0.8155 0.2910 0.027 Uiso calc 1
C C14 0.09828(14) 1.0785(3) 0.33688(15) 0.0234(4) Uani d 1
H H14 0.0332 1.0824 0.3103 0.028 Uiso calc 1
C C15 0.14737(14) 1.2290(3) 0.38761(15) 0.0223(4) Uani d 1
C C16 0.24238(14) 1.2301(3) 0.42531(15) 0.0234(4) Uani d 1
H H16 0.2746 1.3359 0.4596 0.028 Uiso calc 1
C C17 0.28952(14) 1.0742(3) 0.41216(15) 0.0223(4) Uani d 1
H H17 0.3547 1.0742 0.4361 0.027 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
N2 N1 C7 112.98(16)
N2 N1 H1A 119.1(19)
C7 N1 H1A 127.4(19)
C9 N2 N1 104.11(15)
C10 N3 N4 118.45(16)
C10 N3 H3A 120.8(17)
N4 N3 H3A 120.7(17)
C11 N4 N3 116.10(17)
C2 C1 C6 118.90(18)
C2 C1 C7 118.12(18)
C6 C1 C7 122.97(19)
C3 C2 C1 120.7(2)
C3 C2 H2 119.6
C1 C2 H2 119.7
C2 C3 C4 120.2(2)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 119.4(2)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 120.8(2)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 119.9(2)
C5 C6 H6 120.0
C1 C6 H6 120.0
N1 C7 C8 105.89(17)
N1 C7 C1 125.45(18)
C8 C7 C1 128.65(19)
C7 C8 C9 104.91(17)
C7 C8 H8 127.5
C9 C8 H8 127.5
N2 C9 C8 112.11(17)
N2 C9 C10 122.89(18)
C8 C9 C10 125.00(18)
O1 C10 N3 123.57(18)
O1 C10 C9 120.95(18)
N3 C10 C9 115.48(17)
N4 C11 C12 119.27(19)
N4 C11 H11 120.4
C12 C11 H11 120.4
C13 C12 C17 119.30(18)
C13 C12 C11 119.27(18)
C17 C12 C11 121.41(18)
C14 C13 C12 120.29(19)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 118.87(19)
C15 C14 H14 120.6
C13 C14 H14 120.6
C14 C15 C16 122.17(19)
C14 C15 Br1 118.98(15)
C16 C15 Br1 118.84(16)
C17 C16 C15 118.86(19)
C17 C16 H16 120.6
C15 C16 H16 120.6
C16 C17 C12 120.46(19)
C16 C17 H17 119.8
C12 C17 H17 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.907(2)
O1 C10 1.225(2)
N1 N2 1.346(2)
N1 C7 1.362(3)
N1 H1A 0.90(3)
N2 C9 1.338(3)
N3 C10 1.359(3)
N3 N4 1.370(2)
N3 H3A 0.90(3)
N4 C11 1.282(3)
C1 C2 1.398(3)
C1 C6 1.400(3)
C1 C7 1.468(3)
C2 C3 1.385(3)
C2 H2 0.9500
C3 C4 1.392(3)
C3 H3 0.9500
C4 C5 1.386(3)
C4 H4 0.9500
C5 C6 1.389(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.384(3)
C8 C9 1.397(3)
C8 H8 0.9500
C9 C10 1.470(3)
C11 C12 1.459(3)
C11 H11 0.9500
C12 C13 1.400(3)
C12 C17 1.401(3)
C13 C14 1.392(3)
C13 H13 0.9500
C14 C15 1.379(3)
C14 H14 0.9500
C15 C16 1.385(3)
C16 C17 1.385(3)
C16 H16 0.9500
C17 H17 0.9500
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
N3 H3A N2 . 0.90(3) 2.45(3) 2.787(2) 103(2)
N1 H1A O1 1_545 0.90(3) 1.91(3) 2.783(2) 163(3)
C6 H6 O1 1_545 0.95 2.46 3.151(3) 130
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 C9 0.6(2)
C10 N3 N4 C11 170.82(18)
C6 C1 C2 C3 0.1(3)
C7 C1 C2 C3 -178.9(2)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -0.1(3)
C3 C4 C5 C6 -0.1(3)
C4 C5 C6 C1 0.3(3)
C2 C1 C6 C5 -0.3(3)
C7 C1 C6 C5 178.70(18)
N2 N1 C7 C8 -0.8(2)
N2 N1 C7 C1 179.63(18)
C2 C1 C7 N1 -159.20(19)
C6 C1 C7 N1 21.8(3)
C2 C1 C7 C8 21.3(3)
C6 C1 C7 C8 -157.7(2)
N1 C7 C8 C9 0.6(2)
C1 C7 C8 C9 -179.86(19)
N1 N2 C9 C8 -0.2(2)
N1 N2 C9 C10 -179.13(18)
C7 C8 C9 N2 -0.2(2)
C7 C8 C9 C10 178.65(19)
N4 N3 C10 O1 -0.2(3)
N4 N3 C10 C9 179.64(17)
N2 C9 C10 O1 172.58(19)
C8 C9 C10 O1 -6.2(3)
N2 C9 C10 N3 -7.3(3)
C8 C9 C10 N3 173.97(19)
N3 N4 C11 C12 177.16(17)
N4 C11 C12 C13 170.84(19)
N4 C11 C12 C17 -10.8(3)
C17 C12 C13 C14 -1.4(3)
C11 C12 C13 C14 176.94(18)
C12 C13 C14 C15 -0.6(3)
C13 C14 C15 C16 1.6(3)
C13 C14 C15 Br1 -177.73(15)
C14 C15 C16 C17 -0.5(3)
Br1 C15 C16 C17 178.84(15)
C15 C16 C17 C12 -1.6(3)
C13 C12 C17 C16 2.6(3)
C11 C12 C17 C16 -175.78(18)

_cod_database_fobs_code 1543456
