#------------------------------------------------------------------------------
#$Date: 2015-06-06 05:29:13 +0300 (Sat, 06 Jun 2015) $
#$Revision: 138434 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240802.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_2240802
loop_
_publ_author_name
'Mague, Joel T.'
'Mohamed, Shaaban K.'
'Akkurt, Mehmet'
'Ahmed, Eman A.'
'Khodairy, Ahmed'
_publ_section_title
;
 Crystal structure of
 (4Z)-4-[(dimethylamino)methylidene]-3,5-dioxo-2-phenylpyrazolidine-1-carbaldehyde
;
_journal_coeditor_code           HB7425
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o440
_journal_page_last               o441
_journal_paper_doi               10.1107/S2056989015010038
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H13 N3 O3'
_chemical_formula_moiety         'C13 H13 N3 O3'
_chemical_formula_sum            'C13 H13 N3 O3'
_chemical_formula_weight         259.26
_chemical_name_systematic
(4Z)-4-[(Dimethylamino)methylidene]-3,5-dioxo-2-phenylpyrazolidine-1-carbaldehyde
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 113.2720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.4235(9)
_cell_length_b                   6.1033(2)
_cell_length_c                   16.8611(6)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.33
_cell_measurement_theta_min      3.64
_cell_volume                     2497.96(15)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT  (Bruker, 2014)
;
_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 1.000
_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  0.021
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26486
_diffrn_reflns_theta_full        72.250
_diffrn_reflns_theta_max         72.318
_diffrn_reflns_theta_min         3.642
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Sheldrick, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         4565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0577P)²+0.7347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                3979
_reflns_number_total             4565
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7425sup1.cif
_cod_data_source_block           I
_cod_database_code               2240802
_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   0.823
_shelx_estimated_absorpt_t_max   0.960
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O O1 0.43175(4) 0.79022(16) 0.28697(7) 0.0296(2) Uani d 1
O O2 0.52891(4) 0.15926(16) 0.42906(7) 0.0324(3) Uani d 1
O O3 0.37052(4) 0.10698(18) 0.39957(6) 0.0316(3) Uani d 1
N N1 0.40831(4) 0.46179(18) 0.33205(7) 0.0236(3) Uani d 1
N N2 0.43832(4) 0.26978(18) 0.36829(7) 0.0239(3) Uani d 1
N N3 0.59876(5) 0.64368(19) 0.42207(8) 0.0265(3) Uani d 1
C C1 0.44610(5) 0.6170(2) 0.32599(8) 0.0233(3) Uani d 1
C C2 0.50109(5) 0.5284(2) 0.37179(8) 0.0235(3) Uani d 1
C C3 0.49589(5) 0.3060(2) 0.39467(8) 0.0242(3) Uani d 1
C C4 0.54556(5) 0.6654(2) 0.38045(9) 0.0249(3) Uani d 1
H H4 0.5349 0.8001 0.3502 0.030 Uiso calc 1
C C5 0.63539(6) 0.8195(3) 0.41755(10) 0.0344(3) Uani d 1
H H5A 0.6133 0.9445 0.3861 0.052 Uiso calc 1
H H5B 0.6580 0.7661 0.3874 0.052 Uiso calc 1
H H5C 0.6594 0.8652 0.4761 0.052 Uiso calc 1
C C6 0.62712(6) 0.4598(3) 0.47712(10) 0.0344(3) Uani d 1
H H6A 0.6002 0.3471 0.4750 0.052 Uiso calc 1
H H6B 0.6462 0.5109 0.5367 0.052 Uiso calc 1
H H6C 0.6540 0.3978 0.4566 0.052 Uiso calc 1
C C7 0.41757(5) 0.1104(2) 0.40511(8) 0.0255(3) Uani d 1
H H7 0.4416 -0.0034 0.4367 0.031 Uiso calc 1
C C8 0.35475(5) 0.4373(2) 0.26388(8) 0.0235(3) Uani d 1
C C9 0.34078(5) 0.2502(2) 0.21315(9) 0.0275(3) Uani d 1
H H9 0.3667 0.1349 0.2227 0.033 Uiso calc 1
C C10 0.28831(6) 0.2336(3) 0.14813(9) 0.0311(3) Uani d 1
H H10 0.2783 0.1062 0.1129 0.037 Uiso calc 1
C C11 0.25040(6) 0.4019(3) 0.13433(9) 0.0311(3) Uani d 1
H H11 0.2146 0.3899 0.0897 0.037 Uiso calc 1
C C12 0.26490(6) 0.5880(2) 0.18593(10) 0.0308(3) Uani d 1
H H12 0.2390 0.7031 0.1765 0.037 Uiso calc 1
C C13 0.31717(5) 0.6066(2) 0.25127(9) 0.0271(3) Uani d 1
H H13 0.3271 0.7333 0.2868 0.033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 N2 107.25(10)
C1 N1 C8 120.96(11)
N2 N1 C8 117.89(10)
C7 N2 N1 121.70(11)
C7 N2 C3 122.33(11)
N1 N2 C3 110.76(10)
C4 N3 C6 126.32(12)
C4 N3 C5 119.34(12)
C6 N3 C5 114.31(12)
O1 C1 N1 122.81(12)
O1 C1 C2 129.76(12)
N1 C1 C2 107.42(11)
C4 C2 C3 134.64(12)
C4 C2 C1 117.00(12)
C3 C2 C1 108.28(11)
O2 C3 N2 120.52(12)
O2 C3 C2 133.97(12)
N2 C3 C2 105.51(11)
N3 C4 C2 132.47(13)
N3 C4 H4 113.8
C2 C4 H4 113.8
N3 C5 H5A 109.5
N3 C5 H5B 109.5
H5A C5 H5B 109.5
N3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N3 C6 H6A 109.5
N3 C6 H6B 109.5
H6A C6 H6B 109.5
N3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
O3 C7 N2 123.82(13)
O3 C7 H7 118.1
N2 C7 H7 118.1
C9 C8 C13 121.19(12)
C9 C8 N1 121.16(11)
C13 C8 N1 117.64(12)
C8 C9 C10 119.07(13)
C8 C9 H9 120.5
C10 C9 H9 120.5
C11 C10 C9 120.43(14)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 119.85(13)
C10 C11 H11 120.1
C12 C11 H11 120.1
C11 C12 C13 120.33(13)
C11 C12 H12 119.8
C13 C12 H12 119.8
C8 C13 C12 119.12(13)
C8 C13 H13 120.4
C12 C13 H13 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2234(17)
O2 C3 1.2247(17)
O3 C7 1.2096(17)
N1 C1 1.4094(17)
N1 N2 1.4116(15)
N1 C8 1.4356(16)
N2 C7 1.3789(17)
N2 C3 1.4236(16)
N3 C4 1.3064(17)
N3 C6 1.4607(19)
N3 C5 1.4669(18)
C1 C2 1.4538(17)
C2 C4 1.4019(18)
C2 C3 1.4324(19)
C4 H4 0.9500
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 H7 0.9500
C8 C9 1.387(2)
C8 C13 1.3898(18)
C9 C10 1.3903(19)
C9 H9 0.9500
C10 C11 1.389(2)
C10 H10 0.9500
C11 C12 1.389(2)
C11 H11 0.9500
C12 C13 1.390(2)
C12 H12 0.9500
C13 H13 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
C6 H6A O2 . 0.98 2.08 3.016(2) 160
C5 H5C O3 5_666 0.98 2.52 3.1803(19) 124
C7 H7 O2 5_656 0.95 2.29 3.0663(16) 139
C5 H5B Cg1 2_655 0.98 2.98 3.8823(18) 153
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
C1 N1 N2 C7 161.44(12)
C8 N1 N2 C7 -57.85(16)
C1 N1 N2 C3 6.44(14)
C8 N1 N2 C3 147.14(11)
N2 N1 C1 O1 170.26(12)
C8 N1 C1 O1 31.01(19)
N2 N1 C1 C2 -8.87(14)
C8 N1 C1 C2 -148.12(11)
O1 C1 C2 C4 6.4(2)
N1 C1 C2 C4 -174.52(11)
O1 C1 C2 C3 -170.80(13)
N1 C1 C2 C3 8.25(14)
C7 N2 C3 O2 24.0(2)
N1 N2 C3 O2 178.78(12)
C7 N2 C3 C2 -156.09(12)
N1 N2 C3 C2 -1.27(14)
C4 C2 C3 O2 -0.8(3)
C1 C2 C3 O2 175.68(15)
C4 C2 C3 N2 179.21(14)
C1 C2 C3 N2 -4.26(14)
C6 N3 C4 C2 -2.8(2)
C5 N3 C4 C2 179.28(14)
C3 C2 C4 N3 -9.4(3)
C1 C2 C4 N3 174.34(14)
N1 N2 C7 O3 10.0(2)
C3 N2 C7 O3 162.12(13)
C1 N1 C8 C9 111.30(15)
N2 N1 C8 C9 -23.84(17)
C1 N1 C8 C13 -69.53(16)
N2 N1 C8 C13 155.33(12)
C13 C8 C9 C10 0.6(2)
N1 C8 C9 C10 179.72(13)
C8 C9 C10 C11 -0.2(2)
C9 C10 C11 C12 -0.2(2)
C10 C11 C12 C13 0.0(2)
C9 C8 C13 C12 -0.7(2)
N1 C8 C13 C12 -179.87(12)
C11 C12 C13 C8 0.4(2)

_cod_database_fobs_code 2240802
