#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/76/2227682.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227682
loop_
_publ_author_name
'Shahani, Tara'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 5-Cyclohexyl-4-methyl-1H-pyrazol-3(2H)-one monohydrate
;
_journal_coeditor_code           IS2608
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2760
_journal_page_last               o2761
_journal_paper_doi               10.1107/S1600536810039164
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H16 N2 O, H2 O'
_chemical_formula_moiety         'C10 H16 N2 O, H2 O'
_chemical_formula_sum            'C10 H18 N2 O2'
_chemical_formula_weight         198.26
_chemical_name_systematic
;
5-Cyclohexyl-4-methyl-1H-pyrazol-3(2H)-one monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 112.7820(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4959(3)
_cell_length_b                   6.24970(10)
_cell_length_c                   13.9268(3)
_cell_measurement_reflns_used    9296
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.70
_cell_measurement_theta_min      2.95
_cell_volume                     1083.02(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26403
_diffrn_reflns_theta_full        34.98
_diffrn_reflns_theta_max         34.98
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0623P)²+0.2027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                3863
_reflns_number_total             4715
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2608.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227682
_cod_database_fobs_code          2227682
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.47692(5) 0.58283(9) 0.36443(4) 0.01649(11) Uani d . 1 . .
N N1 0.35298(5) 0.86770(11) 0.49923(5) 0.01570(12) Uani d . 1 . .
N N2 0.43455(5) 0.74179(11) 0.49437(5) 0.01560(12) Uani d . 1 . .
C C1 0.22589(7) 1.31323(13) 0.36124(7) 0.02077(15) Uani d . 1 . .
C C2 0.12483(7) 1.45257(14) 0.33028(7) 0.02375(16) Uani d . 1 . .
C C3 0.07738(7) 1.44773(14) 0.41354(7) 0.02298(16) Uani d . 1 . .
C C4 0.05310(7) 1.21880(14) 0.43594(7) 0.02146(16) Uani d . 1 . .
C C5 0.15219(7) 1.07543(13) 0.46434(7) 0.01902(14) Uani d . 1 . .
C C6 0.19853(6) 1.08190(12) 0.37959(6) 0.01492(13) Uani d . 1 . .
C C7 0.29215(6) 0.93410(11) 0.40136(5) 0.01425(13) Uani d . 1 . .
C C8 0.41832(6) 0.71084(12) 0.39255(5) 0.01420(13) Uani d . 1 . .
C C9 0.32907(6) 0.83939(12) 0.33169(5) 0.01507(13) Uani d . 1 . .
C C10 0.28323(7) 0.85575(15) 0.21552(6) 0.02220(16) Uani d . 1 . .
O O1W 0.39076(5) 0.38748(10) 0.17409(5) 0.02017(12) Uani d . 1 . .
H H1A 0.2820(10) 1.3696(19) 0.4284(10) 0.026(3) Uiso d . 1 . .
H H1B 0.2551(10) 1.319(2) 0.3063(11) 0.030(3) Uiso d . 1 . .
H H2A 0.0700(11) 1.398(2) 0.2637(11) 0.029(3) Uiso d . 1 . .
H H2B 0.1410(11) 1.602(2) 0.3181(11) 0.033(3) Uiso d . 1 . .
H H3A 0.1301(11) 1.516(2) 0.4797(10) 0.028(3) Uiso d . 1 . .
H H3B 0.0083(10) 1.536(2) 0.3909(10) 0.027(3) Uiso d . 1 . .
H H4A -0.0056(10) 1.161(2) 0.3741(11) 0.029(3) Uiso d . 1 . .
H H4B 0.0270(10) 1.214(2) 0.4932(10) 0.028(3) Uiso d . 1 . .
H H5A 0.2079(11) 1.124(2) 0.5307(11) 0.032(3) Uiso d . 1 . .
H H5B 0.1334(10) 0.922(2) 0.4749(10) 0.025(3) Uiso d . 1 . .
H H6 0.1416(10) 1.028(2) 0.3127(9) 0.020(3) Uiso d . 1 . .
H H10A 0.2285(15) 0.956(3) 0.1918(15) 0.066(5) Uiso d . 1 . .
H H10B 0.3351(14) 0.891(3) 0.1877(13) 0.053(5) Uiso d . 1 . .
H H10C 0.2553(13) 0.719(3) 0.1795(14) 0.060(5) Uiso d . 1 . .
H H1N1 0.3647(11) 0.938(2) 0.5581(11) 0.033(3) Uiso d . 1 . .
H H1N2 0.4682(11) 0.646(2) 0.5476(11) 0.034(3) Uiso d . 1 . .
H H1W1 0.4222(13) 0.442(3) 0.2377(13) 0.046(4) Uiso d . 1 . .
H H1W2 0.4323(13) 0.284(3) 0.1729(13) 0.052(5) Uiso d . 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
C7 N1 N2 . . 108.07(6) ?
C7 N1 H1N1 . . 126.7(9) ?
N2 N1 H1N1 . . 118.0(9) ?
C8 N2 N1 . . 108.86(6) ?
C8 N2 H1N2 . . 125.1(9) ?
N1 N2 H1N2 . . 119.0(8) ?
C2 C1 C6 . . 109.64(7) ?
C2 C1 H1A . . 109.2(7) ?
C6 C1 H1A . . 108.4(7) ?
C2 C1 H1B . . 110.0(8) ?
C6 C1 H1B . . 110.7(8) ?
H1A C1 H1B . . 108.9(10) ?
C3 C2 C1 . . 111.37(7) ?
C3 C2 H2A . . 108.8(8) ?
C1 C2 H2A . . 109.1(8) ?
C3 C2 H2B . . 109.6(8) ?
C1 C2 H2B . . 110.7(8) ?
H2A C2 H2B . . 107.2(11) ?
C2 C3 C4 . . 111.10(7) ?
C2 C3 H3A . . 109.2(7) ?
C4 C3 H3A . . 109.7(8) ?
C2 C3 H3B . . 110.8(7) ?
C4 C3 H3B . . 109.0(8) ?
H3A C3 H3B . . 106.9(11) ?
C3 C4 C5 . . 111.51(7) ?
C3 C4 H4A . . 109.1(8) ?
C5 C4 H4A . . 109.8(8) ?
C3 C4 H4B . . 111.4(8) ?
C5 C4 H4B . . 108.8(8) ?
H4A C4 H4B . . 106.1(11) ?
C4 C5 C6 . . 111.20(7) ?
C4 C5 H5A . . 109.6(8) ?
C6 C5 H5A . . 108.8(8) ?
C4 C5 H5B . . 110.4(7) ?
C6 C5 H5B . . 109.5(7) ?
H5A C5 H5B . . 107.3(11) ?
C7 C6 C5 . . 113.01(6) ?
C7 C6 C1 . . 112.05(6) ?
C5 C6 C1 . . 110.36(6) ?
C7 C6 H6 . . 105.2(7) ?
C5 C6 H6 . . 108.0(7) ?
C1 C6 H6 . . 107.9(7) ?
N1 C7 C9 . . 109.38(6) ?
N1 C7 C6 . . 121.81(6) ?
C9 C7 C6 . . 128.78(7) ?
O1 C8 N2 . . 122.31(7) ?
O1 C8 C9 . . 130.36(6) ?
N2 C8 C9 . . 107.32(6) ?
C7 C9 C8 . . 105.99(6) ?
C7 C9 C10 . . 128.25(7) ?
C8 C9 C10 . . 125.68(7) ?
C9 C10 H10A . . 111.8(12) ?
C9 C10 H10B . . 113.4(10) ?
H10A C10 H10B . . 108.0(15) ?
C9 C10 H10C . . 114.0(11) ?
H10A C10 H10C . . 108.0(15) ?
H10B C10 H10C . . 101.0(14) ?
H1W1 O1W H1W2 . . 104.0(14) ?
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
O1 C8 . 1.2880(9) ?
N1 C7 . 1.3555(9) ?
N1 N2 . 1.3760(9) ?
N1 H1N1 . 0.889(14) ?
N2 C8 . 1.3622(9) ?
N2 H1N2 . 0.923(14) ?
C1 C2 . 1.5326(12) ?
C1 C6 . 1.5378(11) ?
C1 H1A . 1.012(13) ?
C1 H1B . 0.987(13) ?
C2 C3 . 1.5267(13) ?
C2 H2A . 0.995(14) ?
C2 H2B . 0.986(14) ?
C3 C4 . 1.5267(13) ?
C3 H3A . 1.013(14) ?
C3 H3B . 1.022(13) ?
C4 C5 . 1.5290(11) ?
C4 H4A . 0.985(14) ?
C4 H4B . 0.989(13) ?
C5 C6 . 1.5354(10) ?
C5 H5A . 0.986(14) ?
C5 H5B . 1.020(13) ?
C6 C7 . 1.4982(10) ?
C6 H6 . 1.009(12) ?
C7 C9 . 1.3836(10) ?
C8 C9 . 1.4226(10) ?
C9 C10 . 1.4953(11) ?
C10 H10A . 0.93(2) ?
C10 H10B . 0.948(17) ?
C10 H10C . 0.987(19) ?
O1W H1W1 . 0.888(17) ?
O1W H1W2 . 0.858(18) ?
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 H1N1 O1W 4_576 0.889(14) 1.866(14) 2.7513(9) 173.7(12) yes
N2 H1N2 O1 3_666 0.924(14) 1.842(13) 2.7552(9) 169.5(13) yes
O1W H1W1 O1 . 0.889(17) 1.851(17) 2.7354(8) 173.2(18) yes
O1W H1W2 O1 2_645 0.860(19) 1.961(19) 2.8007(9) 165.0(16) yes
C5 H5A O1W 4_576 0.987(14) 2.503(15) 3.4161(12) 153.7(11) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C8 . . . . -6.34(8) ?
C6 C1 C2 C3 . . . . 57.93(10) ?
C1 C2 C3 C4 . . . . -56.21(10) ?
C2 C3 C4 C5 . . . . 54.34(10) ?
C3 C4 C5 C6 . . . . -54.98(9) ?
C4 C5 C6 C7 . . . . -176.77(7) ?
C4 C5 C6 C1 . . . . 56.89(9) ?
C2 C1 C6 C7 . . . . 175.19(7) ?
C2 C1 C6 C5 . . . . -57.94(9) ?
N2 N1 C7 C9 . . . . 4.32(9) ?
N2 N1 C7 C6 . . . . -177.56(6) ?
C5 C6 C7 N1 . . . . -23.26(10) ?
C1 C6 C7 N1 . . . . 102.18(8) ?
C5 C6 C7 C9 . . . . 154.47(8) ?
C1 C6 C7 C9 . . . . -80.10(10) ?
N1 N2 C8 O1 . . . . -173.49(7) ?
N1 N2 C8 C9 . . . . 5.81(8) ?
N1 C7 C9 C8 . . . . -0.75(9) ?
C6 C7 C9 C8 . . . . -178.70(7) ?
N1 C7 C9 C10 . . . . 176.30(8) ?
C6 C7 C9 C10 . . . . -1.65(14) ?
O1 C8 C9 C7 . . . . 176.10(8) ?
N2 C8 C9 C7 . . . . -3.12(8) ?
O1 C8 C9 C10 . . . . -1.05(14) ?
N2 C8 C9 C10 . . . . 179.74(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656264
