#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227434.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_2227434
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Yeap, Chin Sing'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 4,5,6,7,8,9-Hexahydro-2H-cycloocta[c]pyrazol-1-ium-3-olate
;
_journal_coeditor_code           FJ2356
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3019
_journal_paper_doi               10.1107/S1600536810043904
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H14 N2 O'
_chemical_formula_moiety         'C9 H14 N2 O'
_chemical_formula_sum            'C9 H14 N2 O'
_chemical_formula_weight         166.22
_chemical_name_systematic
;
4,5,6,7,8,9-Hexahydro-2H-cycloocta[c]pyrazol-1-ium-3-olate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.6200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8078(2)
_cell_length_b                   6.77580(10)
_cell_length_c                   10.7096(2)
_cell_measurement_reflns_used    3802
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      3.46
_cell_volume                     864.03(3)
_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
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6990
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0470P)²+0.3516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                1474
_reflns_number_total             1680
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2356.cif
_cod_data_source_block           I
_cod_original_cell_volume        864.03(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227434
_cod_database_fobs_code          2227434
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 0.41579(8) 0.06094(13) 0.31883(8) 0.0190(2) Uani d . 1 . .
N N1 0.44456(9) 0.21181(16) 0.52370(10) 0.0160(3) Uani d . 1 . .
N N2 0.41423(9) 0.38447(16) 0.56789(11) 0.0154(3) Uani d . 1 . .
C C1 0.34257(10) 0.48051(18) 0.46046(12) 0.0149(3) Uani d . 1 . .
C C2 0.28502(11) 0.66563(19) 0.47482(13) 0.0177(3) Uani d . 1 . .
H H2A 0.2711 0.7476 0.3961 0.021 Uiso calc R 1 . .
H H2B 0.3335 0.7384 0.5525 0.021 Uiso calc R 1 . .
C C3 0.17257(11) 0.6209(2) 0.49123(12) 0.0189(3) Uani d . 1 . .
H H3A 0.1883 0.5734 0.5818 0.023 Uiso calc R 1 . .
H H3B 0.1306 0.7430 0.4807 0.023 Uiso calc R 1 . .
C C4 0.09909(11) 0.4691(2) 0.39200(12) 0.0185(3) Uani d . 1 . .
H H4A 0.0295 0.4555 0.4075 0.022 Uiso calc R 1 . .
H H4B 0.1371 0.3426 0.4113 0.022 Uiso calc R 1 . .
C C5 0.07002(11) 0.5164(2) 0.24164(12) 0.0191(3) Uani d . 1 . .
H H5A -0.0105 0.5025 0.1954 0.023 Uiso calc R 1 . .
H H5B 0.0888 0.6534 0.2339 0.023 Uiso calc R 1 . .
C C6 0.12881(11) 0.38840(19) 0.16907(12) 0.0189(3) Uani d . 1 . .
H H6A 0.0905 0.4065 0.0731 0.023 Uiso calc R 1 . .
H H6B 0.1202 0.2510 0.1889 0.023 Uiso calc R 1 . .
C C7 0.25452(11) 0.42986(19) 0.20469(12) 0.0177(3) Uani d . 1 . .
H H7A 0.2795 0.3581 0.1424 0.021 Uiso calc R 1 . .
H H7B 0.2640 0.5695 0.1918 0.021 Uiso calc R 1 . .
C C8 0.32877(10) 0.37496(19) 0.34518(12) 0.0153(3) Uani d . 1 . .
C C9 0.39626(10) 0.20329(18) 0.38724(12) 0.0150(3) Uani d . 1 . .
H H1N1 0.4969(14) 0.125(3) 0.5823(17) 0.030(4) Uiso d . 1 . .
H H1N2 0.4229(14) 0.397(3) 0.6572(19) 0.037(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
C9 N1 N2 . . 109.39(10) ?
C9 N1 H1N1 . . 128.4(10) ?
N2 N1 H1N1 . . 121.9(10) ?
C1 N2 N1 . . 107.96(10) ?
C1 N2 H1N2 . . 128.7(11) ?
N1 N2 H1N2 . . 119.5(11) ?
N2 C1 C8 . . 109.65(11) ?
N2 C1 C2 . . 121.73(11) ?
C8 C1 C2 . . 128.51(11) ?
C1 C2 C3 . . 111.34(10) ?
C1 C2 H2A . . 109.4 ?
C3 C2 H2A . . 109.4 ?
C1 C2 H2B . . 109.4 ?
C3 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
C4 C3 C2 . . 114.47(10) ?
C4 C3 H3A . . 108.6 ?
C2 C3 H3A . . 108.6 ?
C4 C3 H3B . . 108.6 ?
C2 C3 H3B . . 108.6 ?
H3A C3 H3B . . 107.6 ?
C3 C4 C5 . . 115.79(11) ?
C3 C4 H4A . . 108.3 ?
C5 C4 H4A . . 108.3 ?
C3 C4 H4B . . 108.3 ?
C5 C4 H4B . . 108.3 ?
H4A C4 H4B . . 107.4 ?
C6 C5 C4 . . 115.83(11) ?
C6 C5 H5A . . 108.3 ?
C4 C5 H5A . . 108.3 ?
C6 C5 H5B . . 108.3 ?
C4 C5 H5B . . 108.3 ?
H5A C5 H5B . . 107.4 ?
C5 C6 C7 . . 115.82(11) ?
C5 C6 H6A . . 108.3 ?
C7 C6 H6A . . 108.3 ?
C5 C6 H6B . . 108.3 ?
C7 C6 H6B . . 108.3 ?
H6A C6 H6B . . 107.4 ?
C8 C7 C6 . . 114.98(10) ?
C8 C7 H7A . . 108.5 ?
C6 C7 H7A . . 108.5 ?
C8 C7 H7B . . 108.5 ?
C6 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
C1 C8 C9 . . 106.16(11) ?
C1 C8 C7 . . 126.38(11) ?
C9 C8 C7 . . 127.44(11) ?
O1 C9 N1 . . 122.31(11) ?
O1 C9 C8 . . 130.92(11) ?
N1 C9 C8 . . 106.76(11) ?
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 C9 . 1.2902(15) ?
N1 C9 . 1.3622(16) ?
N1 N2 . 1.3708(15) ?
N1 H1N1 . 0.939(18) ?
N2 C1 . 1.3459(16) ?
N2 H1N2 . 0.925(19) ?
C1 C8 . 1.3807(17) ?
C1 C2 . 1.4912(17) ?
C2 C3 . 1.5438(17) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.5283(18) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.5467(17) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.5343(17) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.5377(18) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.5007(17) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.4199(17) ?
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 O1 3_656 0.938(19) 1.757(19) 2.6900(14) 173.0(19) yes
N2 H1N2 O1 4_566 0.925(19) 1.789(19) 2.7056(14) 170.1(18) 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
C9 N1 N2 C1 . . . . 2.98(13) ?
N1 N2 C1 C8 . . . . -2.13(13) ?
N1 N2 C1 C2 . . . . 174.25(11) ?
N2 C1 C2 C3 . . . . -89.09(14) ?
C8 C1 C2 C3 . . . . 86.55(15) ?
C1 C2 C3 C4 . . . . -46.15(14) ?
C2 C3 C4 C5 . . . . -55.64(15) ?
C3 C4 C5 C6 . . . . 108.08(13) ?
C4 C5 C6 C7 . . . . -72.87(15) ?
C5 C6 C7 C8 . . . . 68.15(15) ?
N2 C1 C8 C9 . . . . 0.52(14) ?
C2 C1 C8 C9 . . . . -175.54(12) ?
N2 C1 C8 C7 . . . . 178.99(11) ?
C2 C1 C8 C7 . . . . 2.9(2) ?
C6 C7 C8 C1 . . . . -77.60(16) ?
C6 C7 C8 C9 . . . . 100.55(14) ?
N2 N1 C9 O1 . . . . 176.18(11) ?
N2 N1 C9 C8 . . . . -2.61(13) ?
C1 C8 C9 O1 . . . . -177.37(13) ?
C7 C8 C9 O1 . . . . 4.2(2) ?
C1 C8 C9 N1 . . . . 1.29(13) ?
C7 C8 C9 N1 . . . . -177.16(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656220
