#------------------------------------------------------------------------------
#$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/36/2003639.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_2003639
loop_
_publ_author_name
'Akama, Y.'
'Shiro, M.'
'Ueda, T.'
'Kajitani, M.'
_publ_section_title
;
 Keto and Enol Tautomers of
 4-Benzoyl-3-methyl-1-phenyl-5(2<i>H</i>)-pyrazolone
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1310
_journal_page_last               1314
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.31
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 91.54(1)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   14.298(3)
_cell_length_b                   14.400(3)
_cell_length_c                   27.187(3)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      20.77
_cell_measurement_theta_min      20.05
_cell_volume                     5595.5(18)
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.012
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            3875
_diffrn_reflns_theta_max         55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       Prismatic
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.18
_refine_ls_extinction_coef       4.9E-07
_refine_ls_extinction_method     secondary
_refine_ls_goodness_of_fit_obs   1.21
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     380
_refine_ls_number_reflns         2541
_refine_ls_R_factor_obs          0.038
_refine_ls_shift/esd_max         0.01
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      w=1/[\s^2^(F~o~)]
_refine_ls_wR_factor_obs         0.056
_reflns_number_observed          2541
_reflns_number_total             3693
_reflns_observed_criterion       I>3\s(I)
_[local]_cod_data_source_file    bk0003.cif
_[local]_cod_data_source_block   enol
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_database_code               2003639
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
O(1a) .1304(1) 1.0063(1) .05686(6) 4.47(5)
O(2a) .1225(2) 1.0446(1) -.03899(6) 5.07(5)
N(1a) .1276(2) .8460(1) .06650(7) 3.67(5)
N(2a) .1234(2) .7662(2) .03790(8) 3.92(6)
C(5a) .1306(2) .9219(2) .03759(9) 3.49(6)
C(4a) .1306(2) .8932(2) -.01120(8) 3.24(6)
C(3a) .1254(2) .7940(2) -.00805(9) 3.45(6)
C(6a) .1216(2) .7211(2) -.04703(10) 4.41(7)
C(7a) .1282(2) .9608(2) -.05000(9) 3.51(6)
C(1"a) .1308(2) .9372(2) -.10319(9) 3.26(6)
C(2"a) .0716(2) .9852(2) -.13553(10) 4.30(7)
C(3"a) .0733(2) .9676(2) -.1852(1) 5.17(8)
C(4"a) .1348(2) .9036(2) -.2033(1) 5.26(8)
C(5"a) .1949(2) .8568(2) -.1719(1) 4.95(8)
C(6"a) .1929(2) .8731(2) -.12176(9) 3.97(7)
C(1'a) .1234(2) .8394(2) .11851(9) 3.40(6)
C(2'a) .1690(2) .9024(2) .14874(10) 4.25(7)
C(3'a) .1620(2) .8944(2) .1988(1) 4.85(8)
C(4'a) .1113(2) .8238(2) .2192(1) 4.91(8)
C(5'a) .0675(2) .7605(2) .1889(1) 4.96(8)
C(6'a) .0727(2) .7677(2) .13845(10) 4.23(7)
O(1b) .1352(1) .7524(1) .43821(6) 4.28(5)
O(2b) .1229(2) .8024(1) .53052(7) 5.30(5)
N(1b) .1332(2) .5904(1) .43356(7) 3.70(5)
N(2b) .1270(2) .5148(1) .46503(8) 3.96(6)
C(5b) .1346(2) .6701(2) .45983(9) 3.49(6)
C(4b) .1320(2) .6477(2) .50948(9) 3.41(6)
C(3b) .1260(2) .5484(2) .50974(9) 3.54(6)
C(6b) .1141(2) .4817(2) .55076(10) 4.37(7)
C(7b) .1308(2) .7210(2) .54530(9) 3.60(6)
C(1"b) .1374(2) .7047(2) .59947(9) 3.43(6)
C(2"b) .0849(2) .7589(2) .6301(1) 4.54(7)
C(3"b) .0902(2) .7463(2) .6805(1) 5.31(8)
C(4"b) .1509(2) .6814(2) .7005(1) 5.36(8)
C(5"b) .2063(2) .6299(2) .6703(1) 4.78(7)
C(6"b) .1996(2) .6412(2) .61999(9) 3.96(7)
C(1'b) .1306(2) .5754(2) .38176(9) 3.69(6)
C(2'b) .1711(2) .6380(2) .35056(10) 4.39(7)
C(3'b) .1669(2) .6214(2) .3003(1) 5.04(8)
C(4'b) .1231(2) .5440(2) .2816(1) 5.28(8)
C(5'b) .0837(2) .4815(2) .3132(1) 5.65(9)
C(6'b) .0875(2) .4967(2) .3635(1) 4.74(8)
H(1a) .1269 1.0494 .0242 ?
H(6a) .0999 .6609 -.0343 ?
H(6'a) .1836 .7122 -.0623 ?
H(6"a) .0893 .7411 -.0784 ?
H(2"a) .0265 1.0304 -.1223 ?
H(3"a) .0285 .9988 -.2082 ?
H(4"a) .1371 .8925 -.2383 ?
H(5"a) .2413 .8129 -.1851 ?
H(6a") .2372 .8402 -.0994 ?
H(2'a) .2089 .9512 .1346 ?
H(3'a) .1958 .9387 .2204 ?
H(4'a) .1068 .8188 .2544 ?
H(5'a) .0290 .7105 .2032 ?
H(6a') .0388 .7232 .1170 ?
H(1b) .1267 .8028 .4698 ?
H(6b) .1082 .4211 .5393 ?
H(6'b) .1571 .4849 .5769 ?
H(6"b) .0664 .4999 .5774 ?
H(2"b) .0417 .8056 .6156 ?
H(3"b) .0487 .7821 .7023 ?
H(4"b) .1560 .6741 .7356 ?
H(5"b) .2517 .5857 .6852 ?
H(6b") .2420 .6056 .5986 ?
H(2'b) .2058 .6919 .3634 ?
H(3'b) .1970 .6646 .2778 ?
H(4'b) .1187 .5345 .2461 ?
H(5'b) .0505 .4268 .2998 ?
H(6b') .0589 .4523 .3857 ?
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
N(2a) N(1a) C(5a) 110.3(2) yes
N(2a) N(1a) C(1'a) 120.0(2) yes
C(5a) N(1a) C(1'a) 129.6(2) yes
N(1a) C(5a) C(4a) 108.4(2) yes
N(1a) N(2a) C(3a) 106.2(2) yes
O(1a) C(5a) N(1a) 120.9(2) yes
C(5a) C(4a) C(3a) 103.8(2) yes
C(5a) C(4a) C(7a) 119.9(2) yes
N(2a) C(3a) C(4a) 111.3(2) yes
N(2a) C(3a) C(6a) 117.4(2) yes
O(2a) C(7a) C(4a) 118.7(2) yes
C(4a) C(7a) C(1"a) 124.0(2) yes
C(5a) O(1a) H(1a) 101.7 yes
N(2b) N(1b) C(5b) 109.9(2) yes
N(2b) N(1b) C(1'b) 119.3(2) yes
C(5b) N(1b) C(1'b) 130.6(2) yes
N(1b) C(5b) C(4b) 108.4(2) yes
N(1b) N(2b) C(3b) 106.5(2) yes
O(1b) C(5b) N(1b) 121.7(2) yes
C(5b) C(4b) C(3b) 103.9(2) yes
C(5b) C(4b) C(7b) 119.3(2) yes
N(2b) C(3b) C(4b) 111.3(2) yes
N(2b) C(3b) C(6b) 117.5(2) yes
O(2b) C(7b) C(4b) 118.4(2) yes
C(4b) C(7b) C(1"b) 123.5(2) yes
C(5b) O(1b) H(1b) 103.6 yes
C(4a) C(3a) C(6a) 131.2(3) no
O(2a) C(7a) C(1"a) 117.2(2) no
C(2"a) C(1"a) C(7a) 118.1(3) no
N(1a) C(1'a) C(6'a) 118.8(3) no
C(2"a) C(1"a) C(6"a) 119.0(3) no
C(4"a) C(5"a) C(6"a) 120.3(3) no
C(2"a) C(3"a) C(4"a) 120.3(3) no
N(1a) C(1'a) C(2'a) 121.0(3) no
C(1"a) C(2"a) C(3"a) 120.1(3) no
C(2'a) C(3'a) C(4'a) 121.4(3) no
C(4'a) C(5'a) C(6'a) 120.8(3) no
O(1a) C(5a) C(4a) 130.4(3) no
C(3a) C(4a) C(7a) 136.2(3) no
C(6"a) C(1"a) C(7a) 122.8(3) no
C(1"a) C(6"a) C(5"a) 120.1(3) no
C(3"a) C(4"a) C(5"a) 120.2(3) no
C(2'a) C(1'a) C(6'a) 120.1(3) no
C(1'a) C(2'a) C(3'a) 119.1(3) no
C(3'a) C(4'a) C(5'a) 119.3(3) no
C(1'a) C(6'a) C(5'a) 119.3(3) no
C(4b) C(3b) C(6b) 131.4(3) no
O(1b) C(5b) C(4b) 129.5(3) no
C(3b) C(4b) C(7b) 136.4(3) no
O(2b) C(7b) C(1"b) 118.1(3) no
C(1'b) C(6'b) C(5'b) 119.0(3) no
C(2"b) C(1"b) C(6"b) 119.3(3) no
C(2"b) C(3"b) C(4"b) 120.1(3) no
C(4"b) C(5"b) C(6"b) 120.6(3) no
N(1b) C(1'b) C(2'b) 120.7(3) no
C(2'b) C(1'b) C(6'b) 120.5(3) no
C(2'b) C(3'b) C(4'b) 121.0(3) no
C(4'b) C(5'b) C(6'b) 121.0(3) no
C(6"b) C(1"b) C(7b) 121.6(3) no
C(1"b) C(2"b) C(3"b) 120.4(3) no
C(3"b) C(4"b) C(5"b) 119.6(3) no
C(1"b) C(6"b) C(5"b) 119.9(3) no
C(1'b) C(2'b) C(3'b) 119.3(3) no
C(3'b) C(4'b) C(5'b) 119.2(3) no
C(2"b) C(1"b) C(7b) 119.0(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1a) O(2a) 2.663(2) yes
O(1a) C(5a) 1.323(3) yes
O(2a) C(7a) 1.247(3) yes
N(1a) N(2a) 1.387(3) yes
N(1a) C(5a) 1.348(3) yes
N(1a) C(1'a) 1.420(3) yes
N(2a) C(3a) 1.313(3) yes
C(5a) C(4a) 1.390(3) yes
C(4a) C(3a) 1.433(3) yes
C(4a) C(7a) 1.436(3) yes
C(3a) C(6a) 1.491(4) yes
C(7a) C(1"a) 1.487(3) yes
C(1"a) C(6"a) 1.384(4) no
C(3"a) C(4"a) 1.365(5) no
C(5"a) C(6"a) 1.378(4) no
C(1'a) C(6'a) 1.381(4) no
C(3'a) C(4'a) 1.367(5) no
C(5'a) C(6'a) 1.382(4) no
C(1"a) C(2"a) 1.390(4) no
C(2"a) C(3"a) 1.376(4) no
C(4"a) C(5"a) 1.370(5) no
C(1'a) C(2'a) 1.383(4) no
C(2'a) C(3'a) 1.373(4) no
C(4'a) C(5'a) 1.369(5) no
O(1b) O(2b) 2.621(3) yes
O(1b) C(5b) 1.323(3) yes
O(2b) C(7b) 1.244(3) yes
N(1b) N(2b) 1.390(3) yes
N(1b) C(5b) 1.351(3) yes
N(1b) C(1'b) 1.424(3) yes
N(2b) C(3b) 1.309(3) yes
C(4b) C(5b) 1.389(3) yes
C(3b) C(4b) 1.432(3) yes
C(4b) C(7b) 1.436(4) yes
C(3b) C(6b) 1.485(4) yes
C(7b) C(1"b) 1.492(4) yes
C(1"b) C(2"b) 1.381(4) no
C(2"b) C(3"b) 1.379(5) no
C(4"b) C(5"b) 1.373(5) no
C(1'b) C(2'b) 1.372(4) no
C(2'b) C(3'b) 1.384(4) no
C(4'b) C(5'b) 1.372(5) no
C(1"b) C(6"b) 1.382(4) no
C(3"b) C(4"b) 1.378(5) no
C(5"b) C(6"b) 1.379(4) no
C(1'b) C(6'b) 1.380(4) no
C(3'b) C(4'b) 1.367(5) no
C(5'b) C(6'b) 1.385(5) no
O(1a) H(1a) 1.09 no
C(2"a) H(2"a) 0.99 no
C(2'a) H(2'a) 0.99 no
C(3"a) H(3"a) 0.99 no
C(3'a) H(3'a) 0.99 no
C(4"b) H(4"b) 0.96 no
C(4'a) H(4'a) 0.96 no
C(5"b) H(5"b) 0.99 no
C(5"a) H(5"a) 1.00 no
C(6a) H(6'a) 1.00 no
C(6a) H(6a) 0.99 no
C(6b) H(6'b) 0.93 no
C(6b) H(6b) 0.93 no
C(6"b) H(6b") 0.99 no
O(1b) H(1b) 1.13 no
C(2"b) H(2"b) 0.99 no
C(2'b) H(2'b) 0.98 no
C(3"b) H(3"b) 0.99 no
C(3'b) H(3'b) 0.97 no
C(4"a) H(4"a) 0.97 no
C(4'b) H(4'b) 0.98 no
C(5'a) H(5'a) 0.99 no
C(5'b) H(5'b) 0.99 no
C(6a) H(6"a) 1.00 no
C(6'a) H(6a') 0.98 no
C(6b) H(6"b) 1.05 no
C(6"a) H(6a") 0.99 no
C(6'b) H(6b') 0.97 no
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
_geom_torsion_publ_flag
O(1a) C(5a) N(1a) N(2a) 176.8(2) yes
O(2a) C(7a) C(4a) C(5a) -2.8(4) yes
O(2a) C(7a) C(1"a) C(2"a) -41.3(4) yes
N(1a) N(2a) C(3a) C(4a) -0.2(3) yes
N(1a) N(2a) C(3a) C(6a) -180.0(2) yes
N(1a) C(5a) C(4a) C(3a) 1.2(3) yes
N(1a) C(5a) C(4a) C(7a) 176.6(2) yes
N(2a) N(1a) C(5a) C(4a) -1.4(3) yes
N(2a) C(3a) C(4a) C(5a) -0.6(3) yes
C(5a) N(1a) N(2a) C(3a) 1.0(3) yes
C(5a) N(1a) C(1'a) C(2'a) -35.2(4) yes
C(4a) C(5a) N(1a) C(1'a) -177.7(2) yes
O(1b) C(5b) N(1b) N(2b) -176.3(3) yes
O(2b) C(7b) C(4b) C(5b) 7.0(4) yes
O(2b) C(7b) C(1"b) C(2"b) 37.2(4) yes
N(1b) N(2b) C(3b) C(4b) -0.2(3) yes
N(1b) N(2b) C(3b) C(6b) 176.6(2) yes
N(1b) C(5b) C(4b) C(3b) -1.8(3) yes
N(1b) C(5b) C(4b) C(7b) -178.7(2) yes
N(2b) N(1b) C(5b) C(4b) 1.8(3) yes
N(2b) C(3b) C(4b) C(5b) 1.3(3) yes
C(5b) N(1b) N(2b) C(3b) -1.0(3) yes
C(5b) N(1b) C(1'b) C(2'b) 30.6(4) yes
C(4b) C(5b) N(1b) C(1'b) 176.8(2) yes