#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/32/2213256.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_2213256
loop_
_publ_author_name
'Huan-Mei Guo'
'Fang-Fang Jian'
'Pu-Su Zhao'
'Xiao-Zheng Sun'
'Cui-Hua Lin'
_publ_section_title
;
 1-Acetyl-5-(4-methylphenyl)-3-(4-nitrophenyl)-2-pyrazoline
;
_journal_coeditor_code           CV2195
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2618
_journal_page_last               o2619
_journal_paper_doi               10.1107/S1600536807007520
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H17 N3 O3'
_chemical_formula_moiety         'C18 H17 N3 O3'
_chemical_formula_sum            'C18 H17 N3 O3'
_chemical_formula_weight         323.35
_chemical_name_systematic
;
1-Acetyl-5-(4-methylphenyl)-3-(4-nitrophenyl)-2-pyrazoline
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.072(5)
_cell_length_b                   11.905(2)
_cell_length_c                   11.759(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_cell_volume                     3260.3(11)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL-PC (Sheldrick, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω
_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  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7239
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.184
_refine_ls_extinction_coef       0.0110(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0647P)²+1.7743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1559
_reflns_number_gt                2473
_reflns_number_total             3545
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2195.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2213256
_cod_database_fobs_code          2213256
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
O O1 0.03391(13) 0.5988(2) -0.3818(2) 0.1322(11) Uani d . 1
O O2 0.08314(11) 0.71195(17) -0.25086(19) 0.0974(7) Uani d . 1
O O3 0.25580(7) 0.02692(15) 0.28221(13) 0.0661(5) Uani d . 1
N N1 0.07003(11) 0.6177(2) -0.2897(2) 0.0774(7) Uani d . 1
N N2 0.19433(6) 0.24609(14) 0.09101(12) 0.0382(4) Uani d . 1
N N3 0.21343(6) 0.14006(14) 0.13298(13) 0.0400(4) Uani d . 1
C C1 0.15193(9) 0.44364(17) -0.03989(16) 0.0455(5) Uani d . 1
H H1A 0.1711 0.4528 0.0388 0.055 Uiso calc R 1
C C2 0.12740(10) 0.53559(19) -0.10484(19) 0.0532(5) Uani d . 1
H H2B 0.1304 0.6067 -0.0711 0.064 Uiso calc R 1
C C3 0.09803(9) 0.51989(18) -0.22177(18) 0.0511(5) Uani d . 1
C C4 0.09414(9) 0.41633(19) -0.27530(17) 0.0523(6) Uani d . 1
H H4A 0.0747 0.4081 -0.3539 0.063 Uiso calc R 1
C C5 0.11970(8) 0.32453(17) -0.21019(15) 0.0440(5) Uani d . 1
H H5A 0.1179 0.2544 -0.2458 0.053 Uiso calc R 1
C C6 0.14832(7) 0.33655(16) -0.09085(14) 0.0352(4) Uani d . 1
C C7 0.17311(7) 0.23763(16) -0.02183(14) 0.0339(4) Uani d . 1
C C8 0.17864(8) 0.12170(15) -0.06924(15) 0.0372(4) Uani d . 1
H H8A 0.2089 0.1187 -0.1103 0.045 Uiso calc R 1
H H8B 0.1428 0.0970 -0.1217 0.045 Uiso calc R 1
C C9 0.19404(7) 0.05070(16) 0.04449(15) 0.0364(4) Uani d . 1
H H9A 0.2255 -0.0013 0.0437 0.044 Uiso calc R 1
C C10 0.24136(8) 0.1222(2) 0.24872(17) 0.0487(5) Uani d . 1
C C11 0.25167(11) 0.2239(2) 0.32705(17) 0.0653(7) Uani d . 1
H H11A 0.2709 0.2017 0.4057 0.098 Uiso calc R 1
H H11B 0.2156 0.2582 0.3270 0.098 Uiso calc R 1
H H11C 0.2751 0.2766 0.2986 0.098 Uiso calc R 1
C C12 0.14194(7) -0.01266(15) 0.06316(14) 0.0337(4) Uani d . 1
C C13 0.11059(8) 0.02378(16) 0.14034(15) 0.0388(4) Uani d . 1
H H13A 0.1234 0.0853 0.1886 0.047 Uiso calc R 1
C C14 0.06035(8) -0.03024(17) 0.14645(15) 0.0412(5) Uani d . 1
H H14A 0.0399 -0.0035 0.1982 0.049 Uiso calc R 1
C C15 0.03977(7) -0.12352(16) 0.07714(15) 0.0380(4) Uani d . 1
C C16 0.07169(8) -0.16014(17) -0.00005(16) 0.0435(5) Uani d . 1
H H16A 0.0590 -0.2219 -0.0480 0.052 Uiso calc R 1
C C17 0.12169(8) -0.10632(17) -0.00646(16) 0.0418(5) Uani d . 1
H H17A 0.1422 -0.1330 -0.0581 0.050 Uiso calc R 1
C C18 -0.01491(8) -0.1824(2) 0.08309(18) 0.0522(6) Uani d . 1
H H18A -0.0311 -0.1456 0.1398 0.078 Uiso calc R 1
H H18B -0.0066 -0.2593 0.1059 0.078 Uiso calc R 1
H H18C -0.0418 -0.1799 0.0073 0.078 Uiso calc R 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 N1 O1 123.8(2)
O2 N1 C3 118.8(2)
O1 N1 C3 117.3(2)
C7 N2 N3 107.54(15)
C10 N3 N2 121.81(16)
C10 N3 C9 125.04(17)
N2 N3 C9 112.72(13)
C2 C1 C6 120.89(17)
C2 C1 H1A 119.6
C6 C1 H1A 119.6
C1 C2 C3 118.7(2)
C1 C2 H2B 120.6
C3 C2 H2B 120.6
C4 C3 C2 122.09(19)
C4 C3 N1 119.34(19)
C2 C3 N1 118.6(2)
C3 C4 C5 118.96(17)
C3 C4 H4A 120.5
C5 C4 H4A 120.5
C4 C5 C6 120.55(19)
C4 C5 H5A 119.7
C6 C5 H5A 119.7
C1 C6 C5 118.76(17)
C1 C6 C7 121.35(15)
C5 C6 C7 119.88(17)
N2 C7 C6 120.13(16)
N2 C7 C8 113.58(16)
C6 C7 C8 126.26(14)
C7 C8 C9 101.83(14)
C7 C8 H8A 111.4
C9 C8 H8A 111.4
C7 C8 H8B 111.4
C9 C8 H8B 111.4
H8A C8 H8B 109.3
N3 C9 C12 112.27(15)
N3 C9 C8 100.33(14)
C12 C9 C8 111.64(13)
N3 C9 H9A 110.7
C12 C9 H9A 110.7
C8 C9 H9A 110.7
O3 C10 N3 119.4(2)
O3 C10 C11 124.10(18)
N3 C10 C11 116.50(19)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C17 117.77(16)
C13 C12 C9 122.80(16)
C17 C12 C9 119.22(16)
C14 C13 C12 120.93(17)
C14 C13 H13A 119.5
C12 C13 H13A 119.5
C13 C14 C15 121.67(17)
C13 C14 H14A 119.2
C15 C14 H14A 119.2
C14 C15 C16 117.12(17)
C14 C15 C18 121.94(17)
C16 C15 C18 120.93(18)
C17 C16 C15 121.31(18)
C17 C16 H16A 119.3
C15 C16 H16A 119.3
C16 C17 C12 121.19(17)
C16 C17 H17A 119.4
C12 C17 H17A 119.4
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.225(3)
O2 N1 1.223(3)
O3 C10 1.222(3)
N1 C3 1.475(3)
N2 C7 1.300(2)
N2 N3 1.390(2)
N3 C10 1.374(2)
N3 C9 1.479(2)
C1 C2 1.379(3)
C1 C6 1.402(3)
C1 H1A 0.9300
C2 C3 1.390(3)
C2 H2B 0.9300
C3 C4 1.377(3)
C4 C5 1.386(3)
C4 H4A 0.9300
C5 C6 1.405(2)
C5 H5A 0.9300
C6 C7 1.469(2)
C7 C8 1.507(3)
C8 C9 1.546(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C12 1.526(2)
C9 H9A 0.9800
C10 C11 1.503(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.389(3)
C12 C17 1.396(3)
C13 C14 1.388(3)
C13 H13A 0.9300
C14 C15 1.392(3)
C14 H14A 0.9300
C15 C16 1.399(3)
C15 C18 1.509(3)
C16 C17 1.382(3)
C16 H16A 0.9300
C17 H17A 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
C1 H1A O3 4_555 0.93 2.54 3.419(5) 159 yes
C8 H8A O3 6_555 0.97 2.57 3.357(3) 138 yes
