#------------------------------------------------------------------------------
#$Date: 2017-07-25 13:39:36 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199302 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/67/1546706.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_1546706
loop_
_publ_author_name
'Boulhaoua, Mohammed'
'Benchidmi, Mohammed'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 2-(3-Bromo-5-nitro-1H-indazol-1-yl)-1-phenylethanone
;
_journal_coeditor_code           ZP4013
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x170559
_journal_paper_doi               10.1107/S2414314617005594
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C15 H10 Br N3 O3'
_chemical_formula_moiety         'C15 H10 Br N3 O3'
_chemical_formula_sum            'C15 H10 Br N3 O3'
_chemical_formula_weight         360.17
_chemical_melting_point          415
_chemical_name_systematic
;
2-(3-Bromo-5-nitro-1H-indazol-1-yl)-1-phenylethanone
;
_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   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.029(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2690(6)
_cell_length_b                   15.6721(7)
_cell_length_c                   7.2136(3)
_cell_measurement_reflns_used    3823
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.695
_cell_measurement_theta_min      2.599
_cell_volume                     1481.50(11)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXTL2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'φ and ω 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  0.0429
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            36498
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_min         2.599
_exptl_absorpt_coefficient_mu    2.790
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       Block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.411
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0378
_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)+(0.0497P)²+0.5228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2760
_reflns_number_total             3823
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zp4013sup1.cif
_cod_data_source_block           I
_cod_database_code               1546706
_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.
;
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
C C1 0.58530(16) 0.58951(14) 0.7404(3) 0.0394(5) Uani d 1
C C2 0.60236(15) 0.67859(13) 0.7387(3) 0.0344(4) Uani d 1
C C3 0.68138(15) 0.73149(14) 0.7045(3) 0.0372(4) Uani d 1
H H3 0.7425 0.7099 0.6763 0.045 Uiso calc 1
C C4 0.66406(15) 0.81759(15) 0.7149(3) 0.0393(5) Uani d 1
C C5 0.57322(17) 0.85329(14) 0.7571(3) 0.0407(5) Uani d 1
H H5 0.5660 0.9123 0.7613 0.049 Uiso calc 1
C C6 0.49523(16) 0.80152(14) 0.7922(3) 0.0383(5) Uani d 1
H H6 0.4346 0.8238 0.8212 0.046 Uiso calc 1
C C7 0.51122(14) 0.71293(14) 0.7824(3) 0.0339(4) Uani d 1
C C8 0.34793(17) 0.64587(16) 0.8557(3) 0.0457(5) Uani d 1
H H8A 0.3415 0.6932 0.9396 0.055 Uiso calc 1
H H8B 0.3376 0.5935 0.9220 0.055 Uiso calc 1
C C9 0.26590(16) 0.65326(14) 0.6852(3) 0.0424(5) Uani d 1
C C10 0.15864(17) 0.64096(17) 0.7165(4) 0.0569(7) Uani d 1
C C11 0.1326(2) 0.6316(3) 0.8921(5) 0.0850(10) Uani d 1
H H11 0.1833 0.6344 0.9967 0.102 Uiso calc 1
C C12 0.0327(3) 0.6182(3) 0.9170(8) 0.1154(16) Uani d 1
H H12 0.0160 0.6125 1.0369 0.138 Uiso calc 1
C C13 -0.0393(3) 0.6136(4) 0.7660(11) 0.139(2) Uani d 1
H H13 -0.1065 0.6035 0.7820 0.167 Uiso calc 1
C C14 -0.0177(3) 0.6229(5) 0.5930(11) 0.187(3) Uani d 1
H H14 -0.0698 0.6206 0.4905 0.225 Uiso calc 1
C C15 0.0850(3) 0.6367(4) 0.5643(7) 0.1321(19) Uani d 1
H H15 0.1010 0.6425 0.4439 0.158 Uiso calc 1
N N1 0.74533(16) 0.87569(14) 0.6780(3) 0.0524(5) Uani d 1
N N2 0.49530(14) 0.56952(12) 0.7801(3) 0.0442(4) Uani d 1
N N3 0.44972(13) 0.64583(12) 0.8077(3) 0.0406(4) Uani d 1
O O1 0.73418(17) 0.95111(13) 0.6986(4) 0.0893(7) Uani d 1
O O2 0.82021(17) 0.84566(15) 0.6268(4) 0.0855(7) Uani d 1
O O3 0.28825(13) 0.66909(13) 0.5328(3) 0.0609(5) Uani d 1
Br Br1 0.67373(2) 0.50413(2) 0.68364(4) 0.05714(12) Uani d 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'
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
N2 C1 C2 112.99(18)
N2 C1 Br1 120.19(16)
C2 C1 Br1 126.77(16)
C3 C2 C7 120.79(19)
C3 C2 C1 135.80(19)
C7 C2 C1 103.41(17)
C4 C3 C2 116.08(18)
C4 C3 H3 122.0
C2 C3 H3 122.0
C3 C4 C5 124.05(19)
C3 C4 N1 117.8(2)
C5 C4 N1 118.2(2)
C6 C5 C4 120.2(2)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 116.8(2)
C5 C6 H6 121.6
C7 C6 H6 121.6
N3 C7 C2 106.83(18)
N3 C7 C6 131.08(19)
C2 C7 C6 122.09(19)
N3 C8 C9 112.68(19)
N3 C8 H8A 109.1
C9 C8 H8A 109.1
N3 C8 H8B 109.1
C9 C8 H8B 109.1
H8A C8 H8B 107.8
O3 C9 C10 122.8(2)
O3 C9 C8 120.5(2)
C10 C9 C8 116.7(2)
C15 C10 C11 119.3(3)
C15 C10 C9 118.0(3)
C11 C10 C9 122.6(3)
C10 C11 C12 121.5(4)
C10 C11 H11 119.2
C12 C11 H11 119.2
C13 C12 C11 118.8(4)
C13 C12 H12 120.6
C11 C12 H12 120.6
C14 C13 C12 121.8(4)
C14 C13 H13 119.1
C12 C13 H13 119.1
C13 C14 C15 120.2(5)
C13 C14 H14 119.9
C15 C14 H14 119.9
C10 C15 C14 118.3(5)
C10 C15 H15 120.8
C14 C15 H15 120.8
O1 N1 O2 122.9(2)
O1 N1 C4 118.6(2)
O2 N1 C4 118.5(2)
C1 N2 N3 105.19(17)
C7 N3 N2 111.57(16)
C7 N3 C8 129.35(19)
N2 N3 C8 119.08(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.309(3)
C1 C2 1.415(3)
C1 Br1 1.867(2)
C2 C3 1.389(3)
C2 C7 1.404(3)
C3 C4 1.373(3)
C3 H3 0.9300
C4 C5 1.405(3)
C4 N1 1.467(3)
C5 C6 1.369(3)
C5 H5 0.9300
C6 C7 1.408(3)
C6 H6 0.9300
C7 N3 1.361(3)
C8 N3 1.446(3)
C8 C9 1.513(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 O3 1.209(3)
C9 C10 1.488(3)
C10 C15 1.352(5)
C10 C11 1.372(4)
C11 C12 1.381(4)
C11 H11 0.9300
C12 C13 1.333(7)
C12 H12 0.9300
C13 C14 1.332(8)
C13 H13 0.9300
C14 C15 1.427(7)
C14 H14 0.9300
C15 H15 0.9300
N1 O1 1.203(3)
N1 O2 1.208(3)
N2 N3 1.369(3)
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
C8 H8A O3 4_576 0.97 2.40 3.315(3) 157.1
C8 H8B O1 2_646 0.97 2.53 3.244(3) 130.7
C5 H5 N2 2_656 0.93 2.60 3.508(3) 166.1
C6 H6 O3 4_576 0.93 2.65 3.502(3) 151.8

_cod_database_fobs_code 1546706
