#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229035.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_2229035
loop_
_publ_author_name
'Dong, Bao-Li'
'Wang, Ming-Liang'
'Li, Yong-Hua'
_publ_section_title
;
 1-[5-(Anthracen-9-yl)-3-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one
;
_journal_coeditor_code           FB2230
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o386
_journal_paper_doi               10.1107/S1600536810053365
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C25 H19 N3 O3'
_chemical_formula_moiety         'C25 H19 N3 O3'
_chemical_formula_sum            'C25 H19 N3 O3'
_chemical_formula_weight         409.43
_chemical_name_systematic
;
1-[5-(Anthracen-9-yl)-3-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-
1-yl]ethan-1-one
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   difmap
_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            4
_cell_length_a                   22.888(5)
_cell_length_b                   9.4031(19)
_cell_length_c                   8.9688(18)
_cell_measurement_reflns_used    3824
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      2.6143
_cell_volume                     1930.2(7)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       'φ and 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  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19272
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.26
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.178
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0389
_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)+(0.0488P)²+0.2241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                2131
_reflns_number_total             2352
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fb2230.cif
_cod_data_source_block           I
_cod_original_cell_volume        1930.3(7)
_cod_database_code               2229035
_cod_database_fobs_code          2229035
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.09343(7) 0.5404(2) 0.2678(2) 0.0364(4) Uani d . 1 . .
C C5 -0.06548(9) 0.5860(2) 0.2243(2) 0.0319(5) Uani d . 1 . .
C C6 -0.00794(9) 0.6399(2) 0.2175(2) 0.0316(4) Uani d . 1 . .
N N2 0.14083(8) 0.6030(2) 0.3366(2) 0.0360(4) Uani d . 1 . .
C C13 -0.09433(10) 0.7481(2) 0.0248(3) 0.0410(5) Uani d . 1 . .
H H13A -0.1228 0.7832 -0.0394 0.049 Uiso calc R 1 . .
C C8 0.06219(10) 0.8147(2) 0.1055(3) 0.0390(5) Uani d . 1 . .
H H8A 0.0915 0.7868 0.1711 0.047 Uiso calc R 1 . .
C C17 0.12204(9) 0.6934(2) 0.4330(3) 0.0335(5) Uani d . 1 . .
C C15 0.03652(9) 0.5881(2) 0.3311(3) 0.0337(5) Uani d . 1 . .
H H15A 0.0208(10) 0.506(3) 0.387(3) 0.040 Uiso d . 1 . .
C C7 0.00641(9) 0.7476(2) 0.1140(2) 0.0326(5) Uani d . 1 . .
C C25 0.22213(9) 0.7571(3) 0.5197(3) 0.0416(5) Uani d . 1 . .
H H25A 0.2374 0.6845 0.4611 0.050 Uiso calc R 1 . .
C C12 -0.03748(10) 0.7977(2) 0.0123(3) 0.0355(5) Uani d . 1 . .
C C23 0.23569(10) 0.9475(2) 0.6891(3) 0.0405(5) Uani d . 1 . .
C C20 0.16176(9) 0.7811(2) 0.5216(3) 0.0344(5) Uani d . 1 . .
C C1 -0.16961(10) 0.6046(3) 0.1484(3) 0.0454(6) Uani d . 1 . .
H H1A -0.1985 0.6480 0.0915 0.054 Uiso calc R 1 . .
O O3 0.25365(12) 1.1255(2) 0.8605(3) 0.0729(7) Uani d . 1 . .
C C14 -0.10970(9) 0.6478(2) 0.1304(3) 0.0368(5) Uani d . 1 . .
O O1 0.05499(8) 0.3576(2) 0.1437(3) 0.0563(5) Uani d . 1 . .
C C22 0.17679(11) 0.9742(3) 0.6936(3) 0.0453(6) Uani d . 1 . .
H H22A 0.1620 1.0473 0.7523 0.054 Uiso calc R 1 . .
C C4 -0.08379(10) 0.4732(3) 0.3199(3) 0.0400(5) Uani d . 1 . .
H H4A -0.0558(12) 0.417(3) 0.377(3) 0.048 Uiso d . 1 . .
C C9 0.07371(11) 0.9182(3) 0.0041(3) 0.0467(6) Uani d . 1 . .
H H9A 0.1101 0.9621 0.0041 0.056 Uiso calc R 1 . .
C C21 0.13977(10) 0.8900(3) 0.6090(3) 0.0421(6) Uani d . 1 . .
H H21A 0.0997 0.9068 0.6110 0.051 Uiso calc R 1 . .
C C16 0.05649(9) 0.7025(3) 0.4436(3) 0.0371(5) Uani d . 1 . .
H H16A 0.0425 0.7960 0.4152 0.045 Uiso calc R 1 . .
H H16B 0.0430 0.6808 0.5435 0.045 Uiso calc R 1 . .
C C3 -0.14067(10) 0.4332(3) 0.3298(3) 0.0463(6) Uani d . 1 . .
H H3A -0.1510 0.3589 0.3929 0.056 Uiso calc R 1 . .
C C11 -0.02261(12) 0.9016(3) -0.0966(3) 0.0474(6) Uani d . 1 . .
H H11A -0.0506 0.9297 -0.1659 0.057 Uiso calc R 1 . .
N N3 0.27495(10) 1.0378(2) 0.7773(3) 0.0515(6) Uani d . 1 . .
C C24 0.25901(10) 0.8402(3) 0.6037(3) 0.0449(6) Uani d . 1 . .
H H24A 0.2991 0.8241 0.6027 0.054 Uiso calc R 1 . .
O O2 0.32753(9) 1.0208(2) 0.7630(3) 0.0698(7) Uani d . 1 . .
C C18 0.09882(10) 0.4194(2) 0.1846(3) 0.0397(5) Uani d . 1 . .
C C2 -0.18442(10) 0.5023(3) 0.2462(4) 0.0497(6) Uani d . 1 . .
H H29A -0.2234 0.4772 0.2587 0.060 Uiso calc R 1 . .
C C19 0.15940(11) 0.3706(3) 0.1485(4) 0.0528(7) Uani d . 1 . .
H H19A 0.1576 0.2937 0.0783 0.079 Uiso calc R 1 . .
H H19B 0.1784 0.3389 0.2380 0.079 Uiso calc R 1 . .
H H19C 0.1811 0.4480 0.1061 0.079 Uiso calc R 1 . .
C C10 0.03117(11) 0.9604(3) -0.1016(3) 0.0515(7) Uani d . 1 . .
H H10A 0.0402 1.0280 -0.1737 0.062 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C18 N1 N2 . . 121.89(18) ?
C18 N1 C15 . . 122.51(18) ?
N2 N1 C15 . . 112.89(18) ?
C6 C5 C4 . . 124.50(19) ?
C6 C5 C14 . . 119.1(2) ?
C4 C5 C14 . . 116.45(19) ?
C5 C6 C7 . . 120.14(18) ?
C5 C6 C15 . . 118.71(19) ?
C7 C6 C15 . . 120.98(18) ?
C17 N2 N1 . . 108.61(17) ?
C14 C13 C12 . . 121.6(2) ?
C14 C13 H13A . . 119.2 ?
C12 C13 H13A . . 119.2 ?
C9 C8 C7 . . 121.8(2) ?
C9 C8 H8A . . 119.1 ?
C7 C8 H8A . . 119.1 ?
N2 C17 C20 . . 122.01(19) ?
N2 C17 C16 . . 114.39(19) ?
C20 C17 C16 . . 123.6(2) ?
N1 C15 C6 . . 115.24(19) ?
N1 C15 C16 . . 101.51(16) ?
C6 C15 C16 . . 114.36(18) ?
N1 C15 H15A . . 106.1(14) ?
C6 C15 H15A . . 110.3(15) ?
C16 C15 H15A . . 108.6(16) ?
C6 C7 C8 . . 124.09(19) ?
C6 C7 C12 . . 119.35(19) ?
C8 C7 C12 . . 116.5(2) ?
C24 C25 C20 . . 120.5(2) ?
C24 C25 H25A . . 119.7 ?
C20 C25 H25A . . 119.7 ?
C13 C12 C11 . . 120.7(2) ?
C13 C12 C7 . . 119.6(2) ?
C11 C12 C7 . . 119.6(2) ?
C22 C23 C24 . . 122.2(2) ?
C22 C23 N3 . . 118.7(2) ?
C24 C23 N3 . . 119.2(2) ?
C21 C20 C25 . . 119.0(2) ?
C21 C20 C17 . . 119.93(19) ?
C25 C20 C17 . . 121.1(2) ?
C2 C1 C14 . . 121.0(2) ?
C2 C1 H1A . . 119.5 ?
C14 C1 H1A . . 119.5 ?
C13 C14 C1 . . 120.8(2) ?
C13 C14 C5 . . 119.8(2) ?
C1 C14 C5 . . 119.3(2) ?
C23 C22 C21 . . 118.7(2) ?
C23 C22 H22A . . 120.6 ?
C21 C22 H22A . . 120.6 ?
C3 C4 C5 . . 121.8(2) ?
C3 C4 H4A . . 116.5(16) ?
C5 C4 H4A . . 121.6(16) ?
C8 C9 C10 . . 121.0(2) ?
C8 C9 H9A . . 119.5 ?
C10 C9 H9A . . 119.5 ?
C20 C21 C22 . . 120.7(2) ?
C20 C21 H21A . . 119.7 ?
C22 C21 H21A . . 119.7 ?
C17 C16 C15 . . 102.38(18) ?
C17 C16 H16A . . 111.3 ?
C15 C16 H16A . . 111.3 ?
C17 C16 H16B . . 111.3 ?
C15 C16 H16B . . 111.3 ?
H16A C16 H16B . . 109.2 ?
C4 C3 C2 . . 121.3(3) ?
C4 C3 H3A . . 119.4 ?
C2 C3 H3A . . 119.4 ?
C10 C11 C12 . . 121.4(2) ?
C10 C11 H11A . . 119.3 ?
C12 C11 H11A . . 119.3 ?
O3 N3 O2 . . 123.3(2) ?
O3 N3 C23 . . 118.6(2) ?
O2 N3 C23 . . 118.1(2) ?
C23 C24 C25 . . 118.9(2) ?
C23 C24 H24A . . 120.5 ?
C25 C24 H24A . . 120.5 ?
O1 C18 N1 . . 119.2(2) ?
O1 C18 C19 . . 123.6(2) ?
N1 C18 C19 . . 117.2(2) ?
C1 C2 C3 . . 119.8(2) ?
C1 C2 H29A . . 120.1 ?
C3 C2 H29A . . 120.1 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C11 C10 C9 . . 119.4(2) ?
C11 C10 H10A . . 120.3 ?
C9 C10 H10A . . 120.3 ?
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 C18 . 1.367(3) ?
N1 N2 . 1.380(3) ?
N1 C15 . 1.490(3) ?
C5 C6 . 1.412(3) ?
C5 C4 . 1.427(3) ?
C5 C14 . 1.440(3) ?
C6 C7 . 1.413(3) ?
C6 C15 . 1.520(3) ?
N2 C17 . 1.287(3) ?
C13 C14 . 1.382(4) ?
C13 C12 . 1.387(3) ?
C13 H13A . 0.9300 ?
C8 C9 . 1.358(3) ?
C8 C7 . 1.426(3) ?
C8 H8A . 0.9300 ?
C17 C20 . 1.462(3) ?
C17 C16 . 1.506(3) ?
C15 C16 . 1.544(3) ?
C15 H15A . 0.99(3) ?
C7 C12 . 1.436(3) ?
C25 C24 . 1.375(3) ?
C25 C20 . 1.400(3) ?
C25 H25A . 0.9300 ?
C12 C11 . 1.423(4) ?
C23 C22 . 1.372(3) ?
C23 C24 . 1.374(4) ?
C23 N3 . 1.468(3) ?
C20 C21 . 1.384(3) ?
C1 C2 . 1.345(4) ?
C1 C14 . 1.439(3) ?
C1 H1A . 0.9300 ?
O3 N3 . 1.214(3) ?
O1 C18 . 1.216(3) ?
C22 C21 . 1.386(3) ?
C22 H22A . 0.9300 ?
C4 C3 . 1.358(3) ?
C4 H4A . 0.97(3) ?
C9 C10 . 1.416(4) ?
C9 H9A . 0.9300 ?
C21 H21A . 0.9300 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C3 C2 . 1.409(4) ?
C3 H3A . 0.9300 ?
C11 C10 . 1.350(4) ?
C11 H11A . 0.9300 ?
N3 O2 . 1.221(3) ?
C24 H24A . 0.9300 ?
C18 C19 . 1.496(3) ?
C2 H29A . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C10 H10A . 0.9300 ?
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
C8 H8A N1 . 0.93 2.47 3.047(3) 120.0
C8 H8A N2 . 0.93 2.54 3.391(3) 151.8
C8 H8A Cg1 . 0.93 2.29 2.979(3) 142
C15 H15A Cg2 2_565 0.99 2.90(3) 3.731(3) 142
C4 H4A Cg3 2_565 0.976 2.95 3.824(3) 150
