##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-05-25
_journal_date_accepted     2012-07-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      8
_journal_page_first     o2483
_journal_page_last     o2483
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812031674
_journal_coeditor_code     JJ2141
_publ_contact_author_name     'Lei Wang'
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering
Linyi University
Linyi 276005
People's Republic of China
;
_publ_contact_author_email     linyiwangcao@163.com
_publ_contact_author_fax     '086 539 8766600'
_publ_contact_author_phone     '086 539 8766300'
_publ_section_title
;
6-Oxo-1,6-dihydropyridazine-3-carbaldehyde monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Lei Wang'
;
School of Chemistry and Chemical Engineering
Linyi University
Linyi 276005
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
6-Oxo-1,6-dihydropyridazine-3-carbaldehyde monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H4 N2 O2, H2 O'
_chemical_formula_sum     'C5 H6 N2 O3'
_chemical_formula_iupac     'C5 H4 N2 O2, H2 O'
_chemical_formula_weight     142.12
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.978(2)
_cell_length_b     6.4150(16)
_cell_length_c     11.354(3)
_cell_angle_alpha     90.00
_cell_angle_beta     101.696(3)
_cell_angle_gamma     90.00
_cell_volume     640.4(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1099
_cell_measurement_theta_min     3.66
_cell_measurement_theta_max     25.58
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.474
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     296
_exptl_absorpt_coefficient_mu     0.124
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9757
_exptl_absorpt_correction_T_max     0.9865
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3981
_diffrn_reflns_av_R_equivalents     0.0244
_diffrn_reflns_av_sigmaI/netI     0.0233
_diffrn_reflns_theta_min     2.32
_diffrn_reflns_theta_max     25.49
_diffrn_reflns_theta_full     25.49
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² > σ(F²)
is used only for calculating R-factors(gt) etc. and is not
relevant to the choice of reflections for refinement. R-factors based on
F² are statistically about twice as large as those based on F,
and R-factors based on ALL data will be even larger.
;
_reflns_number_total     1190
_reflns_number_gt     862
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0711
_refine_ls_R_factor_gt     0.0509
_refine_ls_wR_factor_gt     0.1409
_refine_ls_wR_factor_ref     0.1591
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_restrained_S_all     1.055
_refine_ls_number_reflns     1190
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0736P)²+0.3841P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.300
_refine_diff_density_min     -0.211
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.009(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'SMART (Bruker, 2004)'
_computing_cell_refinement     'SMART (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.2572(2) 1.0090(3) 0.98272(18) 0.0477(6) Uani d . 1 1 . .
    N N2 0.1866(2) 0.9050(3) 1.05760(18) 0.0452(6) Uani d . 1 1 . .
    H H1 0.1462 0.9788 1.1061 0.054 Uiso calc R 1 1 . .
    O O1 0.4654(3) 0.9374(4) 0.7609(2) 0.0853(8) Uani d . 1 1 . .
    O O2 0.0999(2) 0.6205(3) 1.13746(18) 0.0611(6) Uani d . 1 1 . .
    O O3 0.0862(3) 0.2000(3) 0.19846(18) 0.0672(7) Uani d . 1 1 . .
    H H1W 0.0911 0.3173 0.1755 0.101 Uiso d R 1 1 . .
    H H2W 0.0389 0.1858 0.2485 0.101 Uiso d R 1 1 . .
    C C1 0.3210(3) 0.8957(4) 0.9111(2) 0.0456(7) Uani d . 1 1 . .
    C C2 0.3184(3) 0.6758(4) 0.9111(2) 0.0524(7) Uani d . 1 1 . .
    H H2 0.3661 0.6012 0.8590 0.063 Uiso calc R 1 1 . .
    C C3 0.2468(3) 0.5760(4) 0.9866(2) 0.0528(7) Uani d . 1 1 . .
    H H3 0.2453 0.4311 0.9885 0.063 Uiso calc R 1 1 . .
    C C4 0.1722(3) 0.6946(4) 1.0650(2) 0.0461(7) Uani d . 1 1 . .
    C C5 0.4022(3) 1.0224(4) 0.8288(2) 0.0410(6) Uani d . 1 1 . .
    H H5 0.4017 1.1673 0.8323 0.049 Uiso calc R 1 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
    N1 0.0609(14) 0.0400(12) 0.0494(12) -0.0020(10) 0.0286(11) 0.0013(9)
    N2 0.0585(13) 0.0379(12) 0.0486(12) -0.0005(10) 0.0332(10) -0.0021(9)
    O1 0.1000(18) 0.0802(17) 0.0927(16) -0.0064(14) 0.0598(15) 0.0048(14)
    O2 0.0840(14) 0.0454(11) 0.0703(13) -0.0035(10) 0.0541(11) 0.0018(9)
    O3 0.1018(17) 0.0420(11) 0.0768(14) 0.0021(10) 0.0626(13) -0.0010(9)
    C1 0.0521(15) 0.0438(15) 0.0459(14) -0.0015(12) 0.0218(12) 0.0003(11)
    C2 0.0645(17) 0.0477(16) 0.0545(16) 0.0049(13) 0.0342(14) -0.0041(12)
    C3 0.0706(18) 0.0361(14) 0.0623(16) 0.0006(13) 0.0383(14) -0.0041(12)
    C4 0.0567(16) 0.0379(15) 0.0508(14) 0.0009(12) 0.0276(12) 0.0012(11)
    C5 0.0474(13) 0.0441(14) 0.0389(12) -0.0028(11) 0.0260(11) 0.0014(10)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    N1 C1 . 1.306(3) ?
    N1 N2 . 1.337(3) ?
    N2 C4 . 1.360(3) ?
    N2 H1 . 0.8600 ?
    O1 C5 . 1.179(3) ?
    O2 C4 . 1.241(3) ?
    O3 H1W . 0.8002 ?
    O3 H2W . 0.7808 ?
    C1 C2 . 1.410(4) ?
    C1 C5 . 1.531(3) ?
    C2 C3 . 1.335(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.435(3) ?
    C3 H3 . 0.9300 ?
    C5 H5 . 0.9300 ?
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
    C1 N1 N2 . . 116.3(2) ?
    N1 N2 C4 . . 126.68(19) ?
    N1 N2 H1 . . 116.7 ?
    C4 N2 H1 . . 116.7 ?
    H1W O3 H2W . . 114.8 ?
    N1 C1 C2 . . 123.2(2) ?
    N1 C1 C5 . . 114.1(2) ?
    C2 C1 C5 . . 122.8(2) ?
    C3 C2 C1 . . 119.3(2) ?
    C3 C2 H2 . . 120.3 ?
    C1 C2 H2 . . 120.3 ?
    C2 C3 C4 . . 119.3(2) ?
    C2 C3 H3 . . 120.3 ?
    C4 C3 H3 . . 120.3 ?
    O2 C4 N2 . . 119.3(2) ?
    O2 C4 C3 . . 125.5(2) ?
    N2 C4 C3 . . 115.2(2) ?
    O1 C5 C1 . . 120.3(3) ?
    O1 C5 H5 . . 119.8 ?
    C1 C5 H5 . . 119.8 ?
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
    C1 N1 N2 C4 . . . . -1.4(4) ?
    N2 N1 C1 C2 . . . . -0.4(4) ?
    N2 N1 C1 C5 . . . . -179.1(2) ?
    N1 C1 C2 C3 . . . . 0.5(5) ?
    C5 C1 C2 C3 . . . . 179.1(2) ?
    C1 C2 C3 C4 . . . . 0.9(4) ?
    N1 N2 C4 O2 . . . . -178.3(2) ?
    N1 N2 C4 C3 . . . . 2.7(4) ?
    C2 C3 C4 O2 . . . . 178.7(3) ?
    C2 C3 C4 N2 . . . . -2.3(4) ?
    N1 C1 C5 O1 . . . . 179.3(3) ?
    C2 C1 C5 O1 . . . . 0.5(4) ?
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
    N2 H1 O3 1_566 0.86 1.91 2.745(3) 164.8
    O3 H1W O2 1_554 0.80 2.00 2.794(3) 173.3
    O3 H2W O2 2_546 0.78 2.01 2.790(2) 172.2
_iucr_refine_instructions_details
;
TITL B in P2(1)/c
CELL 0.71073   8.9782   6.4150  11.3542  90.000 101.696  90.000
ZERR    4.00   0.0022   0.0016   0.0028   0.000   0.003   0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C  H  N  O
UNIT 20  24  8  12
OMIT -3 51
L.S. 10
EXTI 0.009399
ACTA
BOND $H
FMAP 2
PLAN 5
CONF
HTAB O3 O2_$3
HTAB O3 O2_$2
HTAB N2 O3_$1
EQIV $3 -x, y-1/2, -z+3/2
EQIV $2 x, y, z-1
EQIV $1 x, y+1, z+1
HTAB
SIZE 0.20 0.18 0.11
WGHT   0.073600   0.000000
FVAR 0.597790
TEMP 23.000
N1     3   0.257219   1.008978   0.982721  11.000000   0.060910 =
           0.040030   0.049400   0.001250   0.028610  -0.002020
N2     3   0.186625   0.905036   1.057601  11.000000   0.058530 =
           0.037930   0.048550  -0.002060   0.033160  -0.000540
AFIX 43
H1     2   0.146188   0.978782   1.106078  11.000000  -1.200000
AFIX 0
O1     4   0.465374   0.937418   0.760914  11.000000   0.100010 =
           0.080180   0.092730   0.004760   0.059850  -0.006430
O2     4   0.099939   0.620520   1.137456  11.000000   0.083950 =
           0.045350   0.070310   0.001820   0.054130  -0.003470
O3     4   0.086210   0.199975   0.198464  11.000000   0.101760 =
           0.041980   0.076790  -0.000950   0.062610   0.002120
AFIX 3
H1W    2   0.091053   0.317265   0.175550  11.000000  -1.500000
H2W    2   0.038924   0.185787   0.248534  11.000000  -1.500000
AFIX 0
C1     1   0.321019   0.895670   0.911091  11.000000   0.052080 =
           0.043850   0.045920   0.000260   0.021780  -0.001540
C2     1   0.318399   0.675844   0.911084  11.000000   0.064490 =
           0.047680   0.054490  -0.004130   0.034190   0.004850
AFIX 43
H2     2   0.366055   0.601185   0.858990  11.000000  -1.200000
AFIX 0
C3     1   0.246803   0.576034   0.986626  11.000000   0.070590 =
           0.036090   0.062300  -0.004060   0.038300   0.000620
AFIX 43
H3     2   0.245285   0.431123   0.988464  11.000000  -1.200000
AFIX 0
C4     1   0.172198   0.694592   1.064975  11.000000   0.056730 =
           0.037930   0.050780   0.001210   0.027590   0.000850
C5     1   0.402209   1.022429   0.828766  11.000000   0.047440 =
           0.044100   0.038860   0.001360   0.025970  -0.002850
AFIX 43
H5     2   0.401708   1.167260   0.832291  11.000000  -1.200000
AFIX
HKLF 4
END
Q1     1   0.357900   0.996900   0.866900  11.000000   0.050000 0.300000
Q2     1   0.389100   1.092100   0.833200  11.000000   0.050000 0.270000
Q3     1   0.284400   1.130900   0.992800  11.000000   0.050000 0.150000
Q4     1   0.381300   1.208300   0.899000  11.000000   0.050000 0.130000
Q5     1   0.463500   1.230300   0.755100  11.000000   0.050000 0.130000
HKLF 4
REM  B in P2(1)/c
REM R1=  0.0509 for    862 Fo > 4sig(Fo)  and  0.0711 for all   1190 data
REM     92 parameters refined using      0 restraints
;
