#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/80/2228084.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228084
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Loh, Wan-Sin'
'Nayak, Suresh P.'
_publ_section_title
;
 4-Methoxybenzaldehyde (5-bromopyrimidin-2-yl)hydrazone monohydrate
;
_journal_coeditor_code           WN2404
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2467
_journal_paper_doi               10.1107/S1600536810033283
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H11 Br N4 O, H2 O'
_chemical_formula_moiety         'C12 H11 Br N4 O, H2 O'
_chemical_formula_sum            'C12 H13 Br N4 O2'
_chemical_formula_weight         325.17
_chemical_name_systematic
;
4-Methoxybenzaldehyde (5-bromopyrimidin-2-yl)hydrazone monohydrate
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   13.0606(3)
_cell_length_b                   60.5887(10)
_cell_length_c                   6.56180(10)
_cell_measurement_reflns_used    5163
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.23
_cell_measurement_theta_min      3.72
_cell_volume                     5192.51(17)
_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      100.00(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       91
_diffrn_reflns_limit_k_min       -92
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12616
_diffrn_reflns_theta_full        32.75
_diffrn_reflns_theta_max         32.75
_diffrn_reflns_theta_min         2.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.171
_exptl_absorpt_correction_T_max  0.5584
_exptl_absorpt_correction_T_min  0.3651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.397
_refine_ls_abs_structure_details 'Flack (1983), 2037 Friedel pairs'
_refine_ls_abs_structure_Flack   0.012(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4593
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0258
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0521
_reflns_number_gt                4107
_reflns_number_total             4593
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2404.cif
_cod_data_source_block           I
_cod_original_cell_volume        5192.52(17)
_cod_database_code               2228084
_cod_database_fobs_code          2228084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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 0.088547(13) 0.026408(2) 0.69853(3) 0.02305(5) Uani d . 1 . .
O O1 0.08828(10) 0.235769(16) 0.7073(2) 0.0206(2) Uani d . 1 . .
N N1 0.04426(12) 0.07710(2) 1.1084(2) 0.0181(3) Uani d . 1 . .
N N2 0.05839(12) 0.09353(2) 0.7759(2) 0.0168(3) Uani d . 1 . .
N N3 0.03392(13) 0.11442(2) 1.0691(2) 0.0175(3) Uani d . 1 . .
N N4 0.04759(10) 0.133332(18) 0.9574(2) 0.0156(2) Uani d . 1 . .
C C1 0.05708(15) 0.05747(3) 1.0215(3) 0.0194(3) Uani d . 1 . .
C C2 0.07009(14) 0.05472(3) 0.8133(3) 0.0182(3) Uani d . 1 . .
C C3 0.06893(12) 0.07344(2) 0.6943(3) 0.0176(3) Uani d . 1 . .
C C4 0.04600(12) 0.09446(2) 0.9789(2) 0.0149(3) Uani d . 1 . .
C C5 0.03372(14) 0.15154(3) 1.0534(3) 0.0165(3) Uani d . 1 . .
C C6 0.04819(11) 0.17289(2) 0.9545(3) 0.0147(3) Uani d . 1 . .
C C7 0.03424(14) 0.19218(3) 1.0688(2) 0.0183(3) Uani d . 1 . .
C C8 0.04797(14) 0.21285(2) 0.9828(2) 0.0186(3) Uani d . 1 . .
C C9 0.07649(14) 0.21461(3) 0.7790(2) 0.0167(3) Uani d . 1 . .
C C10 0.09188(14) 0.19569(3) 0.6627(2) 0.0167(3) Uani d . 1 . .
C C11 0.07730(14) 0.17500(3) 0.7492(2) 0.0167(3) Uani d . 1 . .
C C12 0.11941(17) 0.23826(3) 0.5009(3) 0.0242(4) Uani d . 1 . .
O O1W 0.24687(11) 0.12558(2) 0.72556(19) 0.0203(3) Uani d . 1 . .
H H1W1 0.184(2) 0.1255(4) 0.749(4) 0.037(7) Uiso d . 1 . .
H H2W1 0.2655(18) 0.1332(4) 0.826(4) 0.027(6) Uiso d . 1 . .
H H1N3 0.0212(17) 0.1149(3) 1.189(5) 0.030(6) Uiso d . 1 . .
H H1A 0.0590(17) 0.0449(4) 1.110(3) 0.023(5) Uiso d . 1 . .
H H3A 0.0769(19) 0.0728(4) 0.546(4) 0.035(7) Uiso d . 1 . .
H H5A 0.0120(15) 0.1507(3) 1.198(4) 0.022(5) Uiso d . 1 . .
H H7A 0.0149(15) 0.1910(3) 1.218(4) 0.020(5) Uiso d . 1 . .
H H8A 0.041(2) 0.2255(4) 1.052(4) 0.036(7) Uiso d . 1 . .
H H10A 0.1133(19) 0.1960(4) 0.522(4) 0.036(6) Uiso d . 1 . .
H H11A 0.0919(16) 0.1621(3) 0.667(4) 0.023(5) Uiso d . 1 . .
H H12A 0.1909(19) 0.2312(3) 0.491(4) 0.033(6) Uiso d . 1 . .
H H12B 0.1262(15) 0.2538(3) 0.476(4) 0.023(5) Uiso d . 1 . .
H H12C 0.0727(17) 0.2324(4) 0.415(4) 0.031(6) 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
C9 O1 C12 . . 117.21(13) ?
C1 N1 C4 . . 115.10(14) ?
C3 N2 C4 . . 116.63(14) ?
C4 N3 N4 . . 119.77(14) ?
C4 N3 H1N3 . . 118.9(14) ?
N4 N3 H1N3 . . 121.3(14) ?
C5 N4 N3 . . 115.91(15) ?
N1 C1 C2 . . 123.06(16) ?
N1 C1 H1A . . 117.1(13) ?
C2 C1 H1A . . 119.8(13) ?
C3 C2 C1 . . 117.26(16) ?
C3 C2 Br1 . . 121.57(14) ?
C1 C2 Br1 . . 121.17(14) ?
N2 C3 C2 . . 121.59(19) ?
N2 C3 H3A . . 116.5(15) ?
C2 C3 H3A . . 121.9(15) ?
N2 C4 N1 . . 126.34(14) ?
N2 C4 N3 . . 118.98(13) ?
N1 C4 N3 . . 114.68(14) ?
N4 C5 C6 . . 121.68(15) ?
N4 C5 H5A . . 117.8(10) ?
C6 C5 H5A . . 120.5(10) ?
C7 C6 C11 . . 118.19(14) ?
C7 C6 C5 . . 118.99(16) ?
C11 C6 C5 . . 122.81(14) ?
C8 C7 C6 . . 121.30(15) ?
C8 C7 H7A . . 119.3(9) ?
C6 C7 H7A . . 119.4(9) ?
C7 C8 C9 . . 119.66(14) ?
C7 C8 H8A . . 123.6(17) ?
C9 C8 H8A . . 116.8(17) ?
O1 C9 C10 . . 124.35(15) ?
O1 C9 C8 . . 115.47(14) ?
C10 C9 C8 . . 120.17(14) ?
C11 C10 C9 . . 119.95(14) ?
C11 C10 H10A . . 116.7(14) ?
C9 C10 H10A . . 123.3(14) ?
C10 C11 C6 . . 120.72(14) ?
C10 C11 H11A . . 118.3(13) ?
C6 C11 H11A . . 120.9(13) ?
O1 C12 H12A . . 105.9(13) ?
O1 C12 H12B . . 106.9(14) ?
H12A C12 H12B . . 108.1(17) ?
O1 C12 H12C . . 111.1(15) ?
H12A C12 H12C . . 114(2) ?
H12B C12 H12C . . 110(2) ?
H1W1 O1W H2W1 . . 98(2) ?
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 C2 . 1.8886(17) ?
O1 C9 . 1.3745(19) ?
O1 C12 . 1.422(2) ?
N1 C1 . 1.329(2) ?
N1 C4 . 1.352(2) ?
N2 C3 . 1.337(2) ?
N2 C4 . 1.343(2) ?
N3 C4 . 1.356(2) ?
N3 N4 . 1.3719(18) ?
N3 H1N3 . 0.81(3) ?
N4 C5 . 1.284(2) ?
C1 C2 . 1.387(3) ?
C1 H1A . 0.95(2) ?
C2 C3 . 1.377(2) ?
C3 H3A . 0.98(3) ?
C5 C6 . 1.459(2) ?
C5 H5A . 0.99(2) ?
C6 C7 . 1.401(2) ?
C6 C11 . 1.406(2) ?
C7 C8 . 1.386(2) ?
C7 H7A . 1.01(2) ?
C8 C9 . 1.392(2) ?
C8 H8A . 0.89(2) ?
C9 C10 . 1.392(2) ?
C10 C11 . 1.389(2) ?
C10 H10A . 0.96(2) ?
C11 H11A . 0.97(2) ?
C12 H12A . 1.03(2) ?
C12 H12B . 0.957(19) ?
C12 H12C . 0.90(3) ?
O1W H1W1 . 0.83(3) ?
O1W H2W1 . 0.84(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
_geom_hbond_publ_flag
O1W H1W1 N2 . 0.84(3) 2.55(3) 3.153(2) 131(2) yes
O1W H1W1 N4 . 0.84(3) 2.30(3) 3.0511(19) 151(2) yes
O1W H2W1 N2 3 0.84(3) 2.01(3) 2.8341(19) 169(2) yes
N3 H1N3 O1W 11_455 0.81(3) 1.99(3) 2.7773(19) 165.1(19) yes
C5 H5A O1W 11_455 0.99(2) 2.43(2) 3.257(2) 140.7(13) 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
C4 N3 N4 C5 . . . . 179.31(15) ?
C4 N1 C1 C2 . . . . -0.8(3) ?
N1 C1 C2 C3 . . . . -0.3(3) ?
N1 C1 C2 Br1 . . . . 179.74(14) ?
C4 N2 C3 C2 . . . . -1.9(2) ?
C1 C2 C3 N2 . . . . 1.7(3) ?
Br1 C2 C3 N2 . . . . -178.33(12) ?
C3 N2 C4 N1 . . . . 0.8(3) ?
C3 N2 C4 N3 . . . . -179.34(15) ?
C1 N1 C4 N2 . . . . 0.6(3) ?
C1 N1 C4 N3 . . . . -179.35(16) ?
N4 N3 C4 N2 . . . . -8.4(2) ?
N4 N3 C4 N1 . . . . 171.56(15) ?
N3 N4 C5 C6 . . . . 178.45(14) ?
N4 C5 C6 C7 . . . . -178.50(16) ?
N4 C5 C6 C11 . . . . 0.4(3) ?
C11 C6 C7 C8 . . . . 0.4(3) ?
C5 C6 C7 C8 . . . . 179.38(16) ?
C6 C7 C8 C9 . . . . -0.2(3) ?
C12 O1 C9 C10 . . . . -0.7(2) ?
C12 O1 C9 C8 . . . . 178.75(17) ?
C7 C8 C9 O1 . . . . 180.00(15) ?
C7 C8 C9 C10 . . . . -0.5(3) ?
O1 C9 C10 C11 . . . . -179.58(15) ?
C8 C9 C10 C11 . . . . 0.9(3) ?
C9 C10 C11 C6 . . . . -0.7(3) ?
C7 C6 C11 C10 . . . . 0.1(2) ?
C5 C6 C11 C10 . . . . -178.87(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656313
