#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/83/2018316.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_2018316
loop_
_publ_author_name
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
_publ_section_title
;
 Hydrogen-bonded structures of the 1:1 and 1:2 compounds of chloranilic
 acid with pyrrolidin-2-one and piperidin-2-one
;
_journal_coeditor_code           FG3233
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o500
_journal_page_last               o504
_journal_paper_doi               10.1107/S0108270111048165
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H2 Cl2 O4 , C5 H9 N O'
_chemical_formula_moiety         'C6 H2 Cl2 O4, C5 H9 N O'
_chemical_formula_sum            'C11 H11 Cl2 N O5'
_chemical_formula_weight         308.12
_chemical_name_common
;
chloranilic acid--piperidin-2-one (1/1)
;
_chemical_name_systematic
;
2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione--piperidin-2-one (1/1)
;
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.1397(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.41079(17)
_cell_length_b                   8.0690(4)
_cell_length_c                   18.1026(3)
_cell_measurement_reflns_used    20671
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     1244.42(7)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22572
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1999)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632.00
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0504P)²+0.3081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                3461
_reflns_number_total             3626
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3233.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C11 H11 Cl2 N O5 '
_cod_database_code               2018316
_cod_database_fobs_code          2018316
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +x,+y,+z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 +x,1/2-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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 -0.30305(3) -0.02569(4) 0.031690(16) 0.03449(9) Uani d . 1 1
Cl Cl2 0.80710(3) 0.06618(3) 0.475761(15) 0.02900(8) Uani d . 1 1
O O1 -0.24763(9) -0.16354(12) -0.10548(5) 0.03547(19) Uani d . 1 1
O O2 -0.00427(9) 0.14039(10) 0.13842(4) 0.02759(16) Uani d . 1 1
O O3 0.77697(8) -0.06244(10) 0.62203(4) 0.02892(16) Uani d . 1 1
O O4 0.48019(8) 0.14740(9) 0.35802(4) 0.02517(15) Uani d . 1 1
O O5 0.23199(8) 0.29476(9) 0.25294(4) 0.02459(14) Uani d . 1 1
N N1 0.11471(9) 0.53820(10) 0.20403(5) 0.02419(16) Uani d . 1 1
C C1 -0.13645(10) -0.08690(11) -0.05607(5) 0.02177(17) Uani d . 1 1
C C2 -0.13551(10) -0.00962(12) 0.01693(6) 0.02176(17) Uani d . 1 1
C C3 -0.00826(10) 0.07172(11) 0.07132(5) 0.02066(17) Uani d . 1 1
C C4 0.65172(10) -0.03715(11) 0.56359(5) 0.01989(16) Uani d . 1 1
C C5 0.63718(10) 0.03365(11) 0.48650(6) 0.01996(16) Uani d . 1 1
C C6 0.49578(10) 0.07663(11) 0.42678(5) 0.01946(16) Uani d . 1 1
C C7 0.24018(10) 0.45058(11) 0.24947(5) 0.01901(16) Uani d . 1 1
C C8 0.39309(10) 0.53859(12) 0.29494(6) 0.02279(17) Uani d . 1 1
H H8A 0.4586 0.5255 0.2646 0.027 Uiso calc R 1 1
H H8B 0.4493 0.4855 0.3490 0.027 Uiso calc R 1 1
C C9 0.37450(12) 0.72260(12) 0.30730(6) 0.0292(2) Uani d . 1 1
H H9A 0.4780 0.7781 0.3277 0.035 Uiso calc R 1 1
H H9B 0.3318 0.7378 0.3483 0.035 Uiso calc R 1 1
C C10 0.26314(11) 0.79935(12) 0.22612(6) 0.02631(19) Uani d . 1 1
H H10A 0.2539 0.9200 0.2331 0.032 Uiso calc R 1 1
H H10B 0.3055 0.7830 0.1851 0.032 Uiso calc R 1 1
C C11 0.10335(11) 0.71930(12) 0.19677(7) 0.0285(2) Uani d . 1 1
H H11A 0.0490 0.7620 0.2292 0.034 Uiso calc R 1 1
H H11B 0.0398 0.7497 0.1390 0.034 Uiso calc R 1 1
H H1 0.0264(19) 0.486(2) 0.1784(10) 0.045(4) Uiso d . 1 1
H H2 0.088(2) 0.189(2) 0.1716(11) 0.053(5) Uiso d . 1 1
H H4 0.391(2) 0.186(2) 0.3278(11) 0.046(4) Uiso 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 0.0033 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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_3
_geom_angle
C3 O2 H2 . 115.6(12)
C6 O4 H4 . 116.8(12)
C7 N1 C11 . 126.92(8)
C7 N1 H1 . 118.0(12)
C11 N1 H1 . 114.8(12)
O1 C1 C2 . 123.76(9)
O1 C1 C3 3 117.95(9)
C2 C1 C3 3 118.29(7)
C3 C2 C1 . 121.97(8)
C3 C2 Cl1 . 120.79(7)
C1 C2 Cl1 . 117.23(7)
O2 C3 C2 . 122.88(8)
O2 C3 C1 3 117.39(8)
C2 C3 C1 3 119.73(8)
O3 C4 C5 . 123.89(8)
O3 C4 C6 3_656 117.57(8)
C5 C4 C6 3_656 118.51(7)
C6 C5 C4 . 121.62(8)
C6 C5 Cl2 . 121.21(7)
C4 C5 Cl2 . 117.14(6)
O4 C6 C5 . 122.75(8)
O4 C6 C4 3_656 117.55(7)
C5 C6 C4 3_656 119.65(8)
O5 C7 N1 . 120.43(8)
O5 C7 C8 . 120.60(8)
N1 C7 C8 . 118.95(8)
C7 C8 C9 . 113.54(8)
C7 C8 H8A . 108.9
C9 C8 H8A . 108.9
C7 C8 H8B . 108.9
C9 C8 H8B . 108.9
H8A C8 H8B . 107.7
C8 C9 C10 . 109.19(8)
C8 C9 H9A . 109.8
C10 C9 H9A . 109.8
C8 C9 H9B . 109.8
C10 C9 H9B . 109.8
H9A C9 H9B . 108.3
C11 C10 C9 . 109.80(8)
C11 C10 H10A . 109.7
C9 C10 H10A . 109.7
C11 C10 H10B . 109.7
C9 C10 H10B . 109.7
H10A C10 H10B . 108.2
N1 C11 C10 . 111.75(8)
N1 C11 H11A . 109.3
C10 C11 H11A . 109.3
N1 C11 H11B . 109.3
C10 C11 H11B . 109.3
H11A C11 H11B . 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C2 . 1.7124(9)
Cl2 C5 . 1.7111(9)
O1 C1 . 1.2174(11)
O2 C3 . 1.3211(11)
O2 H2 . 0.913(19)
O3 C4 . 1.2209(11)
O4 C6 . 1.3197(11)
O4 H4 . 0.845(18)
O5 C7 . 1.2629(11)
N1 C7 . 1.3211(11)
N1 C11 . 1.4671(13)
N1 H1 . 0.870(17)
C1 C2 . 1.4578(13)
C1 C3 3 1.5051(12)
C2 C3 . 1.3537(12)
C4 C5 . 1.4596(13)
C4 C6 3_656 1.5047(12)
C5 C6 . 1.3556(12)
C7 C8 . 1.4987(12)
C8 C9 . 1.5226(13)
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 C10 . 1.5273(14)
C9 H9A . 0.9900
C9 H9B . 0.9900
C10 C11 . 1.5106(13)
C10 H10A . 0.9900
C10 H10B . 0.9900
C11 H11A . 0.9900
C11 H11B . 0.9900
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
N1 H1 O3 4_454 0.869(18) 2.213(19) 2.8871(12) 134.2(14)
O2 H2 O5 . 0.909(19) 1.743(18) 2.6223(11) 162.1(18)
O4 H4 O5 . 0.843(19) 1.767(18) 2.5909(10) 165.1(19)
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_4
_geom_torsion
O1 C1 C2 C3 . . 178.61(10)
C3 C1 C2 C3 3 . -1.23(14)
O1 C1 C2 Cl1 . . -1.33(13)
C3 C1 C2 Cl1 3 . 178.83(7)
C1 C2 C3 O2 . . -178.95(9)
Cl1 C2 C3 O2 . . 0.99(13)
C1 C2 C3 C1 . 3 1.25(15)
Cl1 C2 C3 C1 . 3 -178.82(7)
O3 C4 C5 C6 . . -172.46(9)
C6 C4 C5 C6 3_656 . 5.47(14)
O3 C4 C5 Cl2 . . 5.60(13)
C6 C4 C5 Cl2 3_656 . -176.48(6)
C4 C5 C6 O4 . . 176.99(8)
Cl2 C5 C6 O4 . . -0.99(13)
C4 C5 C6 C4 . 3_656 -5.53(14)
Cl2 C5 C6 C4 . 3_656 176.49(6)
C11 N1 C7 O5 . . 176.79(10)
C11 N1 C7 C8 . . -4.85(14)
O5 C7 C8 C9 . . -161.19(9)
N1 C7 C8 C9 . . 20.45(12)
C7 C8 C9 C10 . . -48.49(12)
C8 C9 C10 C11 . . 61.75(11)
C7 N1 C11 C10 . . 18.13(15)
C9 C10 C11 N1 . . -45.75(12)
