#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/64/2236498.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_2236498
loop_
_publ_author_name
'Guedem, Alphonsine N.'
'Sandjo, Louis P.'
'Opatz, Till'
'Schollmeyer, Dieter'
'Ngadjui, Bonaventure T.'
_publ_section_title
;
 (2E,4R,5R,6S)-2-(4,5,6-Trihydroxycyclohex-2-en-1-ylidene)acetonitrile
;
_journal_coeditor_code           NC2287
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2737
_journal_paper_doi               10.1107/S1600536812035313
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H9 N O3'
_chemical_formula_moiety         'C8 H9 N O3'
_chemical_formula_sum            'C8 H9 N O3'
_chemical_formula_weight         167.16
_chemical_name_systematic
;
(2E,4R,5R,6S)-2-(4,5,6-Trihydroxycyclohex-2-en-1-
ylidene)acetonitrile
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 102.842(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8159(5)
_cell_length_b                   10.2482(5)
_cell_length_c                   8.3573(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      46
_cell_measurement_theta_min      35
_cell_volume                     402.15(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CORINC (Dräger & Gattow, 1971)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2174
_diffrn_reflns_theta_full        69.95
_diffrn_reflns_theta_max         69.95
_diffrn_reflns_theta_min         5.43
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.119
_refine_ls_abs_structure_details 'Flack, (1983)'
_refine_ls_abs_structure_Flack   -0.04(16)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1514
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0255
_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)+(0.0474P)²+0.0306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0708
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                1501
_reflns_number_total             1514
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2287.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2236498
_cod_database_fobs_code          2236498
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_occupancy
_atom_site_symmetry_multiplicity
C C1 0.4167(3) 0.60278(13) 0.16499(15) 0.0204(3) Uani d 1 1
C C2 0.6543(3) 0.54538(12) 0.29376(15) 0.0193(3) Uani d 1 1
H H2 0.822(3) 0.5471(15) 0.2490(18) 0.014(3) Uiso d 1 1
C C3 0.7220(3) 0.63193(13) 0.44623(15) 0.0195(3) Uani d 1 1
H H3 0.881(4) 0.5923(17) 0.525(2) 0.023(4) Uiso d 1 1
C C4 0.8147(3) 0.76563(13) 0.39626(17) 0.0244(3) Uani d 1 1
H H4 0.992(4) 0.7516(17) 0.364(2) 0.023(4) Uiso d 1 1
C C5 0.6001(3) 0.81945(14) 0.2530(2) 0.0291(3) Uani d 1 1
H H5 0.591(4) 0.911(2) 0.238(2) 0.041(5) Uiso d 1 1
C C6 0.4214(3) 0.74407(14) 0.14727(17) 0.0277(3) Uani d 1 1
H H6 0.289(4) 0.7814(18) 0.059(2) 0.023(4) Uiso d 1 1
O O7 0.5884(2) 0.41531(9) 0.32843(12) 0.0246(2) Uani d 1 1
H H7 0.730(5) 0.381(2) 0.375(2) 0.038(5) Uiso d 1 1
O O8 0.47685(18) 0.64281(10) 0.51340(11) 0.0221(2) Uani d 1 1
H H8 0.530(4) 0.644(2) 0.607(3) 0.031(5) Uiso d 1 1
O O9 0.8700(2) 0.85292(10) 0.53125(14) 0.0320(3) Uani d 1 1
H H9 0.730(5) 0.870(2) 0.559(3) 0.045(6) Uiso d 1 1
C C10 0.2197(3) 0.52459(15) 0.07211(16) 0.0252(3) Uani d 1 1
H H10 0.220(4) 0.431(2) 0.0850(19) 0.024(4) Uiso d 1 1
C C11 -0.0065(3) 0.57476(17) -0.05275(17) 0.0316(3) Uani d 1 1
N N12 -0.1938(3) 0.61195(18) -0.15135(17) 0.0451(4) Uani d 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 C1 C6 123.87(12)
C10 C1 C2 120.34(12)
C6 C1 C2 115.77(11)
O7 C2 C1 110.18(11)
O7 C2 C3 113.10(10)
C1 C2 C3 110.92(10)
O7 C2 H2 110.0(10)
C1 C2 H2 106.6(9)
C3 C2 H2 105.8(9)
O8 C3 C2 109.47(10)
O8 C3 C4 110.90(11)
C2 C3 C4 108.30(10)
O8 C3 H3 111.0(10)
C2 C3 H3 108.2(10)
C4 C3 H3 108.9(10)
O9 C4 C5 112.14(12)
O9 C4 C3 111.28(11)
C5 C4 C3 110.86(10)
O9 C4 H4 107.3(10)
C5 C4 H4 109.1(10)
C3 C4 H4 105.9(10)
C6 C5 C4 122.94(13)
C6 C5 H5 119.0(12)
C4 C5 H5 118.1(12)
C5 C6 C1 122.05(12)
C5 C6 H6 120.6(11)
C1 C6 H6 117.4(11)
C2 O7 H7 108.3(16)
C3 O8 H8 106.5(14)
C4 O9 H9 111.1(17)
C1 C10 C11 122.16(14)
C1 C10 H10 123.0(10)
C11 C10 H10 114.9(10)
N12 C11 C10 177.70(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C10 1.3479(19)
C1 C6 1.4563(19)
C1 C2 1.5054(16)
C2 O7 1.4151(15)
C2 C3 1.5272(17)
C2 H2 0.962(16)
C3 O8 1.4200(16)
C3 C4 1.5277(18)
C3 H3 0.981(17)
C4 O9 1.4178(17)
C4 C5 1.5019(19)
C4 H4 0.963(18)
C5 C6 1.334(2)
C5 H5 0.94(2)
C6 H6 0.943(18)
O7 H7 0.79(2)
O8 H8 0.77(2)
O9 H9 0.78(3)
C10 C11 1.426(2)
C10 H10 0.96(2)
C11 N12 1.144(2)
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
O7 H7 O9 2_746 0.79(2) 1.93(2) 2.6885(14) 160(2)
O8 H8 N12 1_656 0.77(2) 2.18(2) 2.9138(16) 160(2)
O9 H9 O7 2_656 0.78(3) 2.02(2) 2.7944(15) 170(2)
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
C10 C1 C2 O7 -16.29(16)
C6 C1 C2 O7 165.07(11)
C10 C1 C2 C3 -142.30(13)
C6 C1 C2 C3 39.06(15)
O7 C2 C3 O8 -63.88(13)
C1 C2 C3 O8 60.49(13)
O7 C2 C3 C4 175.09(9)
C1 C2 C3 C4 -60.54(13)
O8 C3 C4 O9 57.48(13)
C2 C3 C4 O9 177.62(10)
O8 C3 C4 C5 -68.05(13)
C2 C3 C4 C5 52.09(14)
O9 C4 C5 C6 -149.07(14)
C3 C4 C5 C6 -24.01(19)
C4 C5 C6 C1 1.4(2)
C10 C1 C6 C5 172.38(14)
C2 C1 C6 C5 -9.0(2)
C6 C1 C10 C11 -0.6(2)
C2 C1 C10 C11 -179.10(12)
C1 C10 C11 N12 -141(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658131
