#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206119.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_2206119
loop_
_publ_author_name
'Shi, Hong'
'Zhu, Hong-Jun'
'Yin, Peng-Wei'
'Wang, Jin-Tang'
'Shi, Xiao-Lan'
_publ_section_title
;
 5-(4-Methoxyphenyl)-1-phenylpyrazolidin-3-one
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2246
_journal_page_last               o2247
_journal_paper_doi               10.1107/S1600536805019227
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H16 N2 O2'
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_name_systematic
;
5-(4-Methoxyphenyl)-1-phenylpyrazolidin-3-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.53(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.151(3)
_cell_length_b                   7.1660(14)
_cell_length_c                   14.700(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1373.4(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Entaf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2792
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.193
_refine_ls_extinction_coef       0.091(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0480
_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)+(0.1P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1621
_reflns_number_gt                1884
_reflns_number_total             2675
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bd6003.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206119
_cod_database_fobs_code          2206119
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_type_symbol
O1 -0.42726(12) -0.1472(2) 0.19555(10) 0.0532(5) Uani d . 1 O
O2 0.02326(10) 0.2540(2) 0.54039(11) 0.0469(4) Uani d . 1 O
N1 -0.23060(12) 0.4101(2) 0.51635(11) 0.0348(4) Uani d . 1 N
N2 -0.12304(13) 0.4277(2) 0.51878(13) 0.0412(5) Uani d . 1 N
C1 -0.4476(2) -0.3424(4) 0.19620(17) 0.0600(7) Uani d . 1 C
H1A -0.4755 -0.3820 0.1357 0.090 Uiso calc R 1 H
H1B -0.4960 -0.3681 0.2382 0.090 Uiso calc R 1 H
H1C -0.3850 -0.4087 0.2152 0.090 Uiso calc R 1 H
C2 -0.38687(15) -0.0664(3) 0.27700(14) 0.0415(5) Uani d . 1 C
C3 -0.34966(16) 0.1142(3) 0.27207(14) 0.0431(5) Uani d . 1 C
H3A -0.3535 0.1743 0.2156 0.052 Uiso calc R 1 H
C4 -0.30681(15) 0.2052(3) 0.35118(14) 0.0401(5) Uani d . 1 C
H4A -0.2821 0.3262 0.3472 0.048 Uiso calc R 1 H
C5 -0.30028(14) 0.1190(3) 0.43571(13) 0.0357(5) Uani d . 1 C
C6 -0.3398(2) -0.0591(3) 0.43935(16) 0.0602(7) Uani d . 1 C
H6A -0.3378 -0.1177 0.4960 0.072 Uiso calc R 1 H
C7 -0.3824(2) -0.1534(3) 0.36084(17) 0.0637(8) Uani d . 1 C
H7A -0.4075 -0.2739 0.3650 0.076 Uiso calc R 1 H
C8 -0.25044(14) 0.2052(3) 0.52459(13) 0.0345(5) Uani d . 1 C
H8A -0.2956 0.1863 0.5718 0.041 Uiso calc R 1 H
C9 -0.14450(15) 0.1220(3) 0.55899(14) 0.0395(5) Uani d . 1 C
H9A -0.1383 0.0951 0.6241 0.047 Uiso calc R 1 H
H9B -0.1329 0.0081 0.5262 0.047 Uiso calc R 1 H
C10 -0.07017(15) 0.2715(3) 0.53951(13) 0.0361(5) Uani d . 1 C
C11 -0.27256(14) 0.5280(2) 0.58005(13) 0.0324(4) Uani d . 1 C
C12 -0.37790(15) 0.5230(3) 0.58120(14) 0.0423(5) Uani d . 1 C
H12A -0.4178 0.4380 0.5444 0.051 Uiso calc R 1 H
C13 -0.42353(17) 0.6437(3) 0.63674(17) 0.0507(6) Uani d . 1 C
H13A -0.4942 0.6399 0.6366 0.061 Uiso calc R 1 H
C14 -0.36558(19) 0.7702(3) 0.69259(16) 0.0535(6) Uani d . 1 C
H14A -0.3968 0.8514 0.7298 0.064 Uiso calc R 1 H
C15 -0.26149(19) 0.7741(3) 0.69224(15) 0.0489(6) Uani d . 1 C
H15A -0.2220 0.8586 0.7297 0.059 Uiso calc R 1 H
C16 -0.21375(16) 0.6534(3) 0.63662(13) 0.0387(5) Uani d . 1 C
H16A -0.1429 0.6568 0.6374 0.046 Uiso calc R 1 H
H2A -0.0975(18) 0.528(4) 0.4929(16) 0.055(7) Uiso d . 1 H
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
_geom_angle_publ_flag
C2 O1 C1 117.39(17) yes
N2 N1 C11 113.72(15) yes
N2 N1 C8 105.61(14) yes
C11 N1 C8 116.17(15) yes
C10 N2 N1 114.88(16) yes
C10 N2 H2A 123.8(16) yes
N1 N2 H2A 119.2(15) yes
O1 C1 H1A 109.5 ?
O1 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O1 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O1 C2 C7 123.8(2) ?
O1 C2 C3 116.51(19) ?
C7 C2 C3 119.7(2) ?
C4 C3 C2 120.10(19) ?
C4 C3 H3A 119.9 ?
C2 C3 H3A 119.9 ?
C5 C4 C3 120.99(19) ?
C5 C4 H4A 119.5 ?
C3 C4 H4A 119.5 ?
C4 C5 C6 117.98(19) ?
C4 C5 C8 124.26(18) ?
C6 C5 C8 117.75(18) ?
C5 C6 C7 122.0(2) ?
C5 C6 H6A 119.0 ?
C7 C6 H6A 119.0 ?
C2 C7 C6 119.3(2) ?
C2 C7 H7A 120.4 ?
C6 C7 H7A 120.4 ?
N1 C8 C5 112.95(16) ?
N1 C8 C9 104.26(15) ?
C5 C8 C9 113.36(16) ?
N1 C8 H8A 108.7 ?
C5 C8 H8A 108.7 ?
C9 C8 H8A 108.7 ?
C10 C9 C8 104.17(15) ?
C10 C9 H9A 110.9 ?
C8 C9 H9A 110.9 ?
C10 C9 H9B 110.9 ?
C8 C9 H9B 110.9 ?
H9A C9 H9B 108.9 ?
O2 C10 N2 125.27(18) ?
O2 C10 C9 126.67(18) ?
N2 C10 C9 108.05(16) ?
C12 C11 C16 119.20(18) ?
C12 C11 N1 117.75(17) ?
C16 C11 N1 122.94(17) ?
C13 C12 C11 120.2(2) ?
C13 C12 H12A 119.9 ?
C11 C12 H12A 119.9 ?
C12 C13 C14 120.9(2) ?
C12 C13 H13A 119.5 ?
C14 C13 H13A 119.5 ?
C15 C14 C13 119.0(2) ?
C15 C14 H14A 120.5 ?
C13 C14 H14A 120.5 ?
C14 C15 C16 121.1(2) ?
C14 C15 H15A 119.5 ?
C16 C15 H15A 119.5 ?
C11 C16 C15 119.6(2) ?
C11 C16 H16A 120.2 ?
C15 C16 H16A 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.373(2) yes
O1 C1 1.424(3) yes
O2 C10 1.233(2) yes
N1 N2 1.416(2) yes
N1 C11 1.425(2) yes
N1 C8 1.500(2) yes
N2 C10 1.332(3) yes
N2 H2A 0.90(2) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C7 1.375(3) ?
C2 C3 1.389(3) ?
C3 C4 1.387(3) ?
C3 H3A 0.9300 ?
C4 C5 1.380(3) ?
C4 H4A 0.9300 ?
C5 C6 1.382(3) ?
C5 C8 1.514(3) ?
C6 C7 1.390(3) ?
C6 H6A 0.9300 ?
C7 H7A 0.9300 ?
C8 C9 1.539(3) ?
C8 H8A 0.9800 ?
C9 C10 1.503(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C11 C12 1.388(3) ?
C11 C16 1.389(3) ?
C12 C13 1.379(3) ?
C12 H12A 0.9300 ?
C13 C14 1.383(3) ?
C13 H13A 0.9300 ?
C14 C15 1.370(3) ?
C14 H14A 0.9300 ?
C15 C16 1.395(3) ?
C15 H15A 0.9300 ?
C16 H16A 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
_geom_hbond_publ_flag
N2 H2A O2 3_566 0.90(3) 1.94(3) 2.825(2) 169(2) yes
C4 H4A N1 . 0.93 2.56 2.901(3) 102 yes
C16 H16A N2 . 0.93 2.43 2.753(3) 100 yes
C6 H6A Cg3 1_545 0.93 2.65 3.558(3) 167 yes
C15 H15A Cg3 2_456 0.93 2.86 3.737(2) 157 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
C11 N1 N2 C10 119.90(18)
C8 N1 N2 C10 -8.6(2)
C1 O1 C2 C7 -12.2(3)
C1 O1 C2 C3 168.2(2)
O1 C2 C3 C4 -179.45(19)
C7 C2 C3 C4 0.9(3)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 -1.4(3)
C3 C4 C5 C8 177.15(18)
C4 C5 C6 C7 1.9(4)
C8 C5 C6 C7 -176.8(2)
O1 C2 C7 C6 179.9(2)
C3 C2 C7 C6 -0.5(4)
C5 C6 C7 C2 -0.9(4)
N2 N1 C8 C5 -107.80(17)
C11 N1 C8 C5 125.14(18)
N2 N1 C8 C9 15.69(19)
C11 N1 C8 C9 -111.37(18)
C4 C5 C8 N1 13.6(3)
C6 C5 C8 N1 -167.87(19)
C4 C5 C8 C9 -104.7(2)
C6 C5 C8 C9 73.8(2)
N1 C8 C9 C10 -17.04(19)
C5 C8 C9 C10 106.18(18)
N1 N2 C10 O2 175.85(18)
N1 N2 C10 C9 -2.8(2)
C8 C9 C10 O2 -166.00(19)
C8 C9 C10 N2 12.6(2)
N2 N1 C11 C12 178.69(16)
C8 N1 C11 C12 -58.4(2)
N2 N1 C11 C16 2.3(3)
C8 N1 C11 C16 125.25(19)
C16 C11 C12 C13 1.2(3)
N1 C11 C12 C13 -175.33(19)
C11 C12 C13 C14 -0.5(3)
C12 C13 C14 C15 -0.1(4)
C13 C14 C15 C16 0.1(3)
C12 C11 C16 C15 -1.2(3)
N1 C11 C16 C15 175.15(18)
C14 C15 C16 C11 0.5(3)
