#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011616.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_2011616
loop_
_publ_author_name
'Quiroga, Jairo'
'Insuasty, Braulio'
'Abonia, Rodrigo'
'Mejía, Diana'
'Cobo, Justo'
'Nogueras, Manuel'
'Sanchez, Adolfo'
'Low, John Nicolson'
_publ_section_title
;
 5,5-Dimethyl-3-(5-methyl-1H-pyrazol-3-ylamino)cyclohex-3-en-1-one
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1457
_journal_page_last               1459
_journal_paper_doi               10.1107/S0108270100012300
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C12 H17 N3 O'
_chemical_formula_sum            'C12 H17 N3 O'
_chemical_formula_weight         219.29
_chemical_name_systematic
;
5,5-dimethyl-3-(5-methyl-1H-pyrazol-3-ylamino)cyclohex-3-en-1-one
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5130(3)
_cell_length_b                   9.4275(3)
_cell_length_c                   10.6441(3)
_cell_measurement_reflns_used    1515
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      3.25
_cell_volume                     1255.65(6)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full .997
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_device_type  'Nonius KAPPA CCD'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .042
_diffrn_reflns_av_sigmaI/netI    .031
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13142
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    .076
_exptl_absorpt_correction_T_max  .996
_exptl_absorpt_correction_T_min  .981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .05
_refine_diff_density_max         .31
_refine_diff_density_min         -.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1515
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          .057
_refine_ls_R_factor_gt           .048
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0676P)²+0.3673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .122
_reflns_number_gt                1360
_reflns_number_total             1515
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gs1111.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'Pna 21'
_cod_database_code               2011616
_cod_database_fobs_code          2011616
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 1.10964(16) .6399(2) .4368(2) .0290(5) Uani d . 1 . . N
C2 1.1109(2) .6181(3) .5613(2) .0301(6) Uani d . 1 . . C
C21 1.2104(2) .6322(4) .6382(3) .0458(8) Uani d . 1 . . C
C3 1.0084(2) .5815(3) .5951(2) .0279(5) Uani d . 1 . . C
C4 .95073(18) .5843(2) .4815(2) .0240(5) Uani d . 1 . . C
N5 1.01159(17) .6207(2) .3848(2) .0292(5) Uani d . 1 . . N
N6 .84220(15) .5633(2) .45551(19) .0260(4) Uani d . 1 A . N
C7 .77125(18) .4823(2) .5174(2) .0262(5) Uani d D 1 . . C
C8 .79550(19) .4000(3) .6198(2) .0271(5) Uani d . 1 A . C
C9 .7170(2) .3153(3) .6787(2) .0307(6) Uani d . 1 . . C
O91 .74012(15) .2407(2) .77250(19) .0410(5) Uani d . 1 A . O
C10 .6014(3) .3270(4) .6379(4) .0314(6) Uani d PD .760(5) A 1 C
C11 .5903(3) .3668(4) .4991(4) .0314(6) Uani d PD .760(5) A 1 C
C12 .6578(3) .5002(4) .4748(4) .0314(6) Uani d PD .760(5) A 1 C
C13 .4732(4) .4009(5) .4714(5) .0482(8) Uani d PD .760(5) A 1 C
C14 .6256(3) .2456(5) .4150(4) .0482(8) Uani d PD .760(5) A 1 C
C10' .6147(9) .2726(14) .6074(12) .0314(6) Uani d PD .240(5) A 2 C
C12' .6653(7) .4544(14) .4457(11) .0314(6) Uani d PD .240(5) A 2 C
C11' .5716(10) .3953(12) .5242(12) .0314(6) Uani d PD .240(5) A 2 C
C13' .4790(12) .3483(19) .4385(15) .0482(8) Uani d PD .240(5) A 2 C
C14' .5378(10) .5157(14) .6122(12) .0482(8) Uani d PD .240(5) A 2 C
H1 1.1665 .6642 .3932 .035 Uiso calc R 1 . . H
H21A 1.2644 .6846 .5902 .069 Uiso calc R 1 . . H
H21B 1.2379 .5377 .6589 .069 Uiso calc R 1 . . H
H21C 1.1942 .6837 .7159 .069 Uiso calc R 1 . . H
H3 .9824 .5594 .6767 .033 Uiso calc R 1 . . H
H6 .8171 .6093 .3899 .031 Uiso calc R 1 . . H
H8 .8664 .4000 .6516 .033 Uiso calc R 1 . . H
H10A .5652 .3998 .6897 .038 Uiso calc PR .760(5) A 1 H
H10B .5652 .2352 .6528 .038 Uiso calc PR .760(5) A 1 H
H12A .6570 .5218 .3838 .038 Uiso calc PR .760(5) A 1 H
H12B .6254 .5816 .5195 .038 Uiso calc PR .760(5) A 1 H
H13A .4653 .4261 .3825 .072 Uiso calc PR .760(5) A 1 H
H13B .4502 .4809 .5237 .072 Uiso calc PR .760(5) A 1 H
H13C .4290 .3178 .4902 .072 Uiso calc PR .760(5) A 1 H
H14A .5785 .1638 .4282 .072 Uiso calc PR .760(5) A 1 H
H14B .6993 .2191 .4356 .072 Uiso calc PR .760(5) A 1 H
H14C .6217 .2755 .3270 .072 Uiso calc PR .760(5) A 1 H
H10C .5590 .2447 .6686 .038 Uiso calc PR .240(5) A 2 H
H10D .6302 .1894 .5536 .038 Uiso calc PR .240(5) A 2 H
H12C .6419 .5446 .4067 .038 Uiso calc PR .240(5) A 2 H
H12D .6802 .3868 .3767 .038 Uiso calc PR .240(5) A 2 H
H13D .4162 .3264 .4900 .072 Uiso calc PR .240(5) A 2 H
H13E .5003 .2637 .3913 .072 Uiso calc PR .240(5) A 2 H
H13F .4615 .4250 .3798 .072 Uiso calc PR .240(5) A 2 H
H14D .5083 .5940 .5626 .072 Uiso calc PR .240(5) A 2 H
H14E .6001 .5491 .6595 .072 Uiso calc PR .240(5) A 2 H
H14F .4834 .4809 .6708 .072 Uiso calc PR .240(5) A 2 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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 N1 N5 113.1(2) no
C2 N1 H1 123.4 no
N5 N1 H1 123.4 no
N1 C2 C3 106.6(2) no
N1 C2 C21 122.5(3) no
C3 C2 C21 130.9(3) no
C2 C21 H21A 109.5 no
C2 C21 H21B 109.5 no
H21A C21 H21B 109.5 no
C2 C21 H21C 109.5 no
H21A C21 H21C 109.5 no
H21B C21 H21C 109.5 no
C2 C3 C4 104.4(2) no
C2 C3 H3 127.8 no
C4 C3 H3 127.8 no
N5 C4 N6 116.1(2) no
N5 C4 C3 112.1(2) no
N6 C4 C3 131.6(2) no
C4 N5 N1 103.7(2) no
C7 N6 C4 128.6(2) no
C7 N6 H6 115.7 no
C4 N6 H6 115.7 no
N6 C7 C8 124.4(2) no
N6 C7 C12 114.4(2) no
C8 C7 C12 120.9(2) no
N6 C7 C12' 114.8(5) no
C8 C7 C12' 118.9(5) no
C12 C7 C12' 20.3(5) no
C7 C8 C9 121.2(2) no
C7 C8 H8 119.4 no
C9 C8 H8 119.4 no
O91 C9 C8 120.7(2) no
O91 C9 C10 119.3(2) no
C8 C9 C10 119.7(2) no
O91 C9 C10' 115.9(5) no
C8 C9 C10' 120.4(5) no
C10 C9 C10' 23.8(5) no
C9 C10 C11 112.4(3) no
C9 C10 H10A 109.1 no
C11 C10 H10A 109.1 no
C9 C10 H10B 109.1 no
C11 C10 H10B 109.1 no
H10A C10 H10B 107.9 no
C14 C11 C10 111.0(3) no
C14 C11 C13 108.9(4) no
C10 C11 C13 108.9(4) no
C14 C11 C12 110.9(3) no
C10 C11 C12 108.3(4) no
C13 C11 C12 108.7(3) no
C7 C12 C11 112.1(3) no
C7 C12 H12A 109.2 no
C11 C12 H12A 109.2 no
C7 C12 H12B 109.2 no
C11 C12 H12B 109.2 no
H12A C12 H12B 107.9 no
C9 C10' C11' 112.0(9) no
C9 C10' H10C 109.2 no
C11' C10' H10C 109.2 no
C9 C10' H10D 109.2 no
C11' C10' H10D 109.2 no
H10C C10' H10D 107.9 no
C11' C12' C7 116.3(9) no
C11' C12' H12C 108.2 no
C7 C12' H12C 108.2 no
C11' C12' H12D 108.2 no
C7 C12' H12D 108.2 no
H12C C12' H12D 107.4 no
C14' C11' C13' 111.6(11) no
C14' C11' C12' 105.9(10) no
C13' C11' C12' 110.8(11) no
C14' C11' C10' 107.4(11) no
C13' C11' C10' 112.6(12) no
C12' C11' C10' 108.3(10) no
C11' C13' H13D 109.5 no
C11' C13' H13E 109.5 no
H13D C13' H13E 109.5 no
C11' C13' H13F 109.5 no
H13D C13' H13F 109.5 no
H13E C13' H13F 109.5 no
C11' C14' H14D 109.5 no
C11' C14' H14E 109.5 no
H14D C14' H14E 109.5 no
C11' C14' H14F 109.5 no
H14D C14' H14F 109.5 no
H14E C14' H14F 109.5 no
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 C2 . 1.342(3) no
N1 N5 . 1.358(3) no
N1 H1 . .8800 no
C2 C3 . 1.376(4) no
C2 C21 . 1.497(4) no
C21 H21A . .9800 no
C21 H21B . .9800 no
C21 H21C . .9800 no
C3 C4 . 1.409(4) no
C3 H3 . .9500 no
C4 N5 . 1.326(3) no
C4 N6 . 1.400(3) yes
N6 C7 . 1.343(3) yes
N6 H6 . .8800 no
C7 C8 . 1.372(3) yes
C7 C12 . 1.500(4) no
C7 C12' . 1.553(8) no
C8 C9 . 1.413(3) yes
C8 H8 . .9500 no
C9 O91 . 1.255(3) yes
C9 C10 . 1.515(4) no
C9 C10' . 1.542(12) no
C10 C11 . 1.530(5) no
C10 H10A . .9900 no
C10 H10B . .9900 no
C11 C14 . 1.517(6) no
C11 C13 . 1.530(6) no
C11 C12 . 1.537(5) no
C12 H12A . .9900 no
C12 H12B . .9900 no
C13 H13A . .9800 no
C13 H13B . .9800 no
C13 H13C . .9800 no
C14 H14A . .9800 no
C14 H14B . .9800 no
C14 H14C . .9800 no
C10' C11' . 1.554(14) no
C10' H10C . .9900 no
C10' H10D . .9900 no
C12' C11' . 1.544(15) no
C12' H12C . .9900 no
C12' H12D . .9900 no
C11' C14' . 1.531(15) no
C11' C13' . 1.539(15) no
C13' H13D . .9800 no
C13' H13E . .9800 no
C13' H13F . .9800 no
C14' H14D . .9800 no
C14' H14E . .9800 no
C14' H14F . .9800 no
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
N1 H1 O91 2_764 .88 1.95 2.804(3) 162 y
N6 H6 O91 3_654 .88 1.90 2.766(3) 168 y
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
N5 N1 C2 C3 .3(3) no
N5 N1 C2 C21 179.6(2) no
N1 C2 C3 C4 .1(3) no
C21 C2 C3 C4 -179.0(3) no
C2 C3 C4 N5 -.5(3) no
C2 C3 C4 N6 -176.6(2) no
N6 C4 N5 N1 177.40(19) no
C3 C4 N5 N1 .7(3) no
C2 N1 N5 C4 -.6(3) no
N5 C4 N6 C7 154.4(2) no
C3 C4 N6 C7 -29.7(4) no
C4 N6 C7 C8 -1.7(4) no
C4 N6 C7 C12 171.8(3) no
C4 N6 C7 C12' -165.9(6) no
N6 C7 C8 C9 -178.8(2) yes
C12 C7 C8 C9 8.1(4) no
C12' C7 C8 C9 -15.2(7) no
C7 C8 C9 O91 -179.9(3) no
C7 C8 C9 C10 -6.8(4) no
C7 C8 C9 C10' 20.7(7) no
O91 C9 C10 C11 -156.5(3) no
C8 C9 C10 C11 30.3(5) no
C10' C9 C10 C11 -68.3(12) no
C9 C10 C11 C14 69.7(4) no
C9 C10 C11 C13 -170.5(3) no
C9 C10 C11 C12 -52.4(5) no
N6 C7 C12 C11 153.5(3) no
C8 C7 C12 C11 -32.7(5) no
C12' C7 C12 C11 57.8(13) no
C14 C11 C12 C7 -68.6(4) no
C10 C11 C12 C7 53.5(5) no
C13 C11 C12 C7 171.7(3) no
O91 C9 C10' C11' 160.7(8) no
C8 C9 C10' C11' -38.9(12) no
C10 C9 C10' C11' 56.4(10) no
N6 C7 C12' C11' -165.1(8) no
C8 C7 C12' C11' 29.8(13) no
C12 C7 C12' C11' -71.5(15) no
C7 C12' C11' C14' 68.8(13) no
C7 C12' C11' C13' -170.1(10) no
C7 C12' C11' C10' -46.1(15) no
C9 C10' C11' C14' -64.7(12) no
C9 C10' C11' C13' 172.1(10) no
C9 C10' C11' C12' 49.2(14) no
