#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/44/2224466.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_2224466
loop_
_publ_author_name
'Goh, Jia Hao'
'Fun, Hoong-Kun'
'Adhikari, Adithya'
'Kalluraya, B.'
_publ_section_title
5-Bromo-2-[5-(4-nitrophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]pyrimidine
_journal_coeditor_code           TK2577
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3134
_journal_page_last               o3135
_journal_paper_doi               10.1107/S1600536809048600
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H14 Br N5 O2'
_chemical_formula_moiety         'C19 H14 Br N5 O2'
_chemical_formula_sum            'C19 H14 Br N5 O2'
_chemical_formula_weight         424.26
_chemical_name_systematic
;
5-Bromo-2-[5-(4-nitrophenyl)-3-phenyl-4,5-dihydro-1H-
pyrazol-1-yl]pyrimidine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.9690(10)
_cell_angle_beta                 103.3030(10)
_cell_angle_gamma                91.5600(10)
_cell_formula_units_Z            2
_cell_length_a                   6.97090(10)
_cell_length_b                   11.6500(2)
_cell_length_c                   12.4365(2)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      33.9
_cell_measurement_theta_min      3.0
_cell_volume                     882.12(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      100.00(10)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_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  0.026
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28197
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  0.760
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.029
_refine_ls_R_factor_gt           0.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0288P)²+0.5594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.058
_refine_ls_wR_factor_ref         0.060
_reflns_number_gt                3431
_reflns_number_total             3804
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2577.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        882.12(2)
_cod_database_code               2224466
_cod_database_fobs_code          2224466
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.32778(3) 0.891599(17) 1.068122(15) 0.02770(7) Uani d . 1 . .
O O1 -0.3115(2) 0.02211(12) 0.64236(12) 0.0274(3) Uani d . 1 . .
O O2 -0.0404(2) -0.01117(12) 0.74511(11) 0.0258(3) Uani d . 1 . .
N N1 0.2287(2) 0.49488(13) 0.46957(12) 0.0175(3) Uani d . 1 . .
N N2 0.2681(2) 0.47661(13) 0.57546(12) 0.0177(3) Uani d . 1 . .
N N3 0.3203(2) 0.54232(13) 0.78176(13) 0.0191(3) Uani d . 1 . .
N N4 0.2364(2) 0.68890(13) 0.69321(13) 0.0182(3) Uani d . 1 . .
N N5 -0.1294(2) 0.03714(13) 0.68034(13) 0.0205(3) Uani d . 1 . .
C C1 0.1859(3) 0.48220(17) 0.22862(16) 0.0224(4) Uani d . 1 . .
C C2 0.1604(3) 0.4683(2) 0.10980(17) 0.0282(4) Uani d . 1 . .
C C3 0.1682(3) 0.3501(2) 0.01564(17) 0.0300(4) Uani d . 1 . .
C C4 0.2012(3) 0.24641(19) 0.04084(17) 0.0275(4) Uani d . 1 . .
C C5 0.2323(3) 0.26060(18) 0.16071(16) 0.0236(4) Uani d . 1 . .
C C6 0.2252(2) 0.37903(16) 0.25600(15) 0.0201(3) Uani d . 1 . .
C C7 0.2607(2) 0.39338(15) 0.38231(15) 0.0176(3) Uani d . 1 . .
C C8 0.3349(3) 0.29328(16) 0.42148(17) 0.0228(4) Uani d . 1 . .
C C9 0.3406(3) 0.35347(16) 0.55889(15) 0.0191(3) Uani d . 1 . .
C C10 0.2129(3) 0.27153(15) 0.59130(14) 0.0175(3) Uani d . 1 . .
C C11 0.0070(3) 0.24832(16) 0.54497(15) 0.0188(3) Uani d . 1 . .
C C12 -0.1072(3) 0.17094(16) 0.57339(15) 0.0191(3) Uani d . 1 . .
C C13 -0.0101(3) 0.11782(15) 0.64817(15) 0.0178(3) Uani d . 1 . .
C C14 0.1942(3) 0.13677(16) 0.69325(16) 0.0211(3) Uani d . 1 . .
C C15 0.3060(3) 0.21486(16) 0.66433(16) 0.0213(3) Uani d . 1 . .
C C16 0.2747(2) 0.57397(15) 0.68747(15) 0.0165(3) Uani d . 1 . .
C C17 0.3326(3) 0.63670(17) 0.89244(16) 0.0207(3) Uani d . 1 . .
C C18 0.2999(3) 0.75881(16) 0.90934(15) 0.0204(3) Uani d . 1 . .
C C19 0.2496(3) 0.78065(16) 0.80562(16) 0.0201(3) Uani d . 1 . .
H H1A 0.177(3) 0.563(2) 0.2909(19) 0.025(5) Uiso d . 1 . .
H H2A 0.138(4) 0.540(2) 0.092(2) 0.038(6) Uiso d . 1 . .
H H3A 0.154(3) 0.340(2) -0.066(2) 0.037(6) Uiso d . 1 . .
H H4A 0.206(3) 0.169(2) -0.020(2) 0.024(5) Uiso d . 1 . .
H H5A 0.257(3) 0.190(2) 0.178(2) 0.028(5) Uiso d . 1 . .
H H8A 0.467(3) 0.2771(19) 0.4110(19) 0.024(5) Uiso d . 1 . .
H H8B 0.250(3) 0.214(2) 0.378(2) 0.031(6) Uiso d . 1 . .
H H9A 0.478(3) 0.3691(17) 0.6123(17) 0.013(4) Uiso d . 1 . .
H H11A -0.055(3) 0.2853(18) 0.4970(18) 0.019(5) Uiso d . 1 . .
H H12A -0.245(3) 0.1549(19) 0.5429(19) 0.024(5) Uiso d . 1 . .
H H14A 0.258(3) 0.0991(19) 0.7416(19) 0.025(5) Uiso d . 1 . .
H H15A 0.446(3) 0.2291(19) 0.6952(19) 0.025(5) Uiso d . 1 . .
H H17A 0.372(3) 0.6149(19) 0.9598(19) 0.022(5) Uiso d . 1 . .
H H19A 0.224(3) 0.8658(19) 0.8141(18) 0.019(5) Uiso 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 N2 . . 107.71(14) ?
C16 N2 N1 . . 121.50(13) ?
C16 N2 C9 . . 123.73(14) ?
N1 N2 C9 . . 113.65(13) ?
C17 N3 C16 . . 115.56(15) ?
C19 N4 C16 . . 115.45(14) ?
O1 N5 O2 . . 123.49(14) ?
O1 N5 C13 . . 118.57(14) ?
O2 N5 C13 . . 117.94(15) ?
C2 C1 C6 . . 120.44(17) ?
C2 C1 H1A . . 118.6(12) ?
C6 C1 H1A . . 121.0(12) ?
C1 C2 C3 . . 120.15(19) ?
C1 C2 H2A . . 120.0(14) ?
C3 C2 H2A . . 119.8(14) ?
C4 C3 C2 . . 119.95(17) ?
C4 C3 H3A . . 119.4(14) ?
C2 C3 H3A . . 120.6(14) ?
C3 C4 C5 . . 120.16(17) ?
C3 C4 H4A . . 120.9(13) ?
C5 C4 H4A . . 118.9(13) ?
C4 C5 C6 . . 120.28(18) ?
C4 C5 H5A . . 120.2(13) ?
C6 C5 H5A . . 119.5(13) ?
C1 C6 C5 . . 118.96(16) ?
C1 C6 C7 . . 121.19(15) ?
C5 C6 C7 . . 119.85(16) ?
N1 C7 C6 . . 121.79(16) ?
N1 C7 C8 . . 114.40(15) ?
C6 C7 C8 . . 123.81(15) ?
C7 C8 C9 . . 102.87(13) ?
C7 C8 H8A . . 112.2(12) ?
C9 C8 H8A . . 110.4(12) ?
C7 C8 H8B . . 112.8(13) ?
C9 C8 H8B . . 111.1(13) ?
H8A C8 H8B . . 107.5(18) ?
N2 C9 C10 . . 113.23(14) ?
N2 C9 C8 . . 101.32(13) ?
C10 C9 C8 . . 113.11(14) ?
N2 C9 H9A . . 110.2(10) ?
C10 C9 H9A . . 107.2(10) ?
C8 C9 H9A . . 111.9(10) ?
C11 C10 C15 . . 119.99(15) ?
C11 C10 C9 . . 121.01(15) ?
C15 C10 C9 . . 118.95(15) ?
C12 C11 C10 . . 120.27(16) ?
C12 C11 H11A . . 119.2(12) ?
C10 C11 H11A . . 120.5(12) ?
C13 C12 C11 . . 118.28(16) ?
C13 C12 H12A . . 120.8(12) ?
C11 C12 H12A . . 121.0(12) ?
C14 C13 C12 . . 122.77(15) ?
C14 C13 N5 . . 118.41(15) ?
C12 C13 N5 . . 118.82(15) ?
C13 C14 C15 . . 118.17(16) ?
C13 C14 H14A . . 122.0(13) ?
C15 C14 H14A . . 119.8(13) ?
C14 C15 C10 . . 120.49(17) ?
C14 C15 H15A . . 119.0(12) ?
C10 C15 H15A . . 120.5(12) ?
N3 C16 N4 . . 127.09(15) ?
N3 C16 N2 . . 114.49(14) ?
N4 C16 N2 . . 118.43(14) ?
N3 C17 C18 . . 122.24(16) ?
N3 C17 H17A . . 115.3(12) ?
C18 C17 H17A . . 122.4(12) ?
C17 C18 C19 . . 117.58(15) ?
C17 C18 Br1 . . 121.08(13) ?
C19 C18 Br1 . . 121.33(13) ?
N4 C19 C18 . . 122.05(16) ?
N4 C19 H19A . . 118.1(11) ?
C18 C19 H19A . . 119.8(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C18 . 1.8863(16) ?
O1 N5 . 1.228(2) ?
O2 N5 . 1.2337(19) ?
N1 C7 . 1.292(2) ?
N1 N2 . 1.3886(19) ?
N2 C16 . 1.365(2) ?
N2 C9 . 1.481(2) ?
N3 C17 . 1.332(2) ?
N3 C16 . 1.346(2) ?
N4 C19 . 1.334(2) ?
N4 C16 . 1.348(2) ?
N5 C13 . 1.471(2) ?
C1 C2 . 1.384(3) ?
C1 C6 . 1.399(3) ?
C1 H1A . 0.95(2) ?
C2 C3 . 1.394(3) ?
C2 H2A . 0.96(2) ?
C3 C4 . 1.383(3) ?
C3 H3A . 0.95(2) ?
C4 C5 . 1.392(3) ?
C4 H4A . 0.91(2) ?
C5 C6 . 1.400(2) ?
C5 H5A . 0.94(2) ?
C6 C7 . 1.468(2) ?
C7 C8 . 1.504(2) ?
C8 C9 . 1.539(2) ?
C8 H8A . 0.97(2) ?
C8 H8B . 0.95(2) ?
C9 C10 . 1.519(2) ?
C9 H9A . 0.995(19) ?
C10 C11 . 1.391(2) ?
C10 C15 . 1.393(2) ?
C11 C12 . 1.389(2) ?
C11 H11A . 0.91(2) ?
C12 C13 . 1.387(2) ?
C12 H12A . 0.93(2) ?
C13 C14 . 1.379(3) ?
C14 C15 . 1.390(2) ?
C14 H14A . 0.93(2) ?
C15 H15A . 0.94(2) ?
C17 C18 . 1.381(3) ?
C17 H17A . 0.96(2) ?
C18 C19 . 1.388(2) ?
C19 H19A . 0.98(2) ?
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
C8 H8B O2 2_556 0.95(2) 2.41(2) 3.352(2) 176.0(17) yes
C11 H11A N4 2_566 0.92(2) 2.56(2) 3.431(2) 160.5(18) yes
C19 H19A O2 1_565 0.98(2) 2.58(2) 3.412(3) 143.3(17) 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 C16 . . . . 170.72(14) ?
C7 N1 N2 C9 . . . . 2.42(18) ?
C6 C1 C2 C3 . . . . 1.8(3) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . -1.8(3) ?
C3 C4 C5 C6 . . . . 1.6(3) ?
C2 C1 C6 C5 . . . . -1.9(3) ?
C2 C1 C6 C7 . . . . 177.49(16) ?
C4 C5 C6 C1 . . . . 0.2(3) ?
C4 C5 C6 C7 . . . . -179.20(16) ?
N2 N1 C7 C6 . . . . 177.49(14) ?
N2 N1 C7 C8 . . . . -2.15(19) ?
C1 C6 C7 N1 . . . . 10.4(2) ?
C5 C6 C7 N1 . . . . -170.23(16) ?
C1 C6 C7 C8 . . . . -170.01(16) ?
C5 C6 C7 C8 . . . . 9.4(2) ?
N1 C7 C8 C9 . . . . 1.11(19) ?
C6 C7 C8 C9 . . . . -178.52(15) ?
C16 N2 C9 C10 . . . . 68.9(2) ?
N1 N2 C9 C10 . . . . -123.07(15) ?
C16 N2 C9 C8 . . . . -169.64(15) ?
N1 N2 C9 C8 . . . . -1.64(17) ?
C7 C8 C9 N2 . . . . 0.35(16) ?
C7 C8 C9 C10 . . . . 121.86(15) ?
N2 C9 C10 C11 . . . . 49.0(2) ?
C8 C9 C10 C11 . . . . -65.5(2) ?
N2 C9 C10 C15 . . . . -133.70(16) ?
C8 C9 C10 C15 . . . . 111.76(18) ?
C15 C10 C11 C12 . . . . 1.4(2) ?
C9 C10 C11 C12 . . . . 178.62(15) ?
C10 C11 C12 C13 . . . . -0.2(2) ?
C11 C12 C13 C14 . . . . -1.2(2) ?
C11 C12 C13 N5 . . . . 179.18(14) ?
O1 N5 C13 C14 . . . . 178.59(15) ?
O2 N5 C13 C14 . . . . -0.9(2) ?
O1 N5 C13 C12 . . . . -1.8(2) ?
O2 N5 C13 C12 . . . . 178.73(14) ?
C12 C13 C14 C15 . . . . 1.5(3) ?
N5 C13 C14 C15 . . . . -178.92(15) ?
C13 C14 C15 C10 . . . . -0.3(3) ?
C11 C10 C15 C14 . . . . -1.1(2) ?
C9 C10 C15 C14 . . . . -178.41(15) ?
C17 N3 C16 N4 . . . . -1.6(2) ?
C17 N3 C16 N2 . . . . 178.34(14) ?
C19 N4 C16 N3 . . . . 1.4(2) ?
C19 N4 C16 N2 . . . . -178.54(14) ?
N1 N2 C16 N3 . . . . -178.10(14) ?
C9 N2 C16 N3 . . . . -11.0(2) ?
N1 N2 C16 N4 . . . . 1.8(2) ?
C9 N2 C16 N4 . . . . 168.92(14) ?
C16 N3 C17 C18 . . . . 0.3(2) ?
N3 C17 C18 C19 . . . . 1.0(3) ?
N3 C17 C18 Br1 . . . . -177.75(12) ?
C16 N4 C19 C18 . . . . 0.1(2) ?
C17 C18 C19 N4 . . . . -1.2(3) ?
Br1 C18 C19 N4 . . . . 177.53(13) ?
