#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:12:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180416 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/85/7208596.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_7208596
loop_
_publ_author_name
'Tobu, Yasuhiro'
'Ikeda, Ryuichi'
'Nihei, Taka-Aki'
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
'Asaji, Tetsuo'
_publ_section_title
;
 Temperature dependence of one-dimensional hydrogen bonding in
 morpholinium hydrogen chloranilate studied by (35)Cl nuclear quadrupole
 resonance and multi-temperature X-ray diffraction.
;
_journal_issue                   35
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              12347
_journal_page_last               12354
_journal_paper_doi               10.1039/c2cp41241a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C10 H11 Cl2 N O5'
_chemical_formula_weight         296.10
_chemical_name_common            'morpholinium hydrogen chloranilete'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.6113(7)
_cell_angle_beta                 116.6498(7)
_cell_angle_gamma                113.4563(7)
_cell_formula_units_Z            2
_cell_length_a                   8.66982(18)
_cell_length_b                   9.21282(19)
_cell_length_c                   9.26605(19)
_cell_measurement_reflns_used    15246
_cell_measurement_temperature    338(1)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.0
_cell_volume                     583.72(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      338(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17198
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_preparation
;
Single crystals suitable for X-ray diffraction were prepared
by slow evaporation from an acetonitrile solution of chloranilic acid
with morpholine (molar ration 1:1).
;
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0364
_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)+(0.0576P)²+0.1179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                3131
_reflns_number_total             3389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cp41241a_2.txt
_cod_data_source_block           338K
_cod_database_code               7208596
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.76731(4) 0.17347(4) 0.70884(4) 0.03902(10) Uani 1 1 d .
Cl2 Cl -0.00488(5) 0.11616(5) 0.18356(4) 0.04441(11) Uani 1 1 d .
O1 O 1.17689(13) 0.32611(11) 0.98439(12) 0.03566(19) Uani 1 1 d .
O2 O 0.62227(12) 0.41032(11) 0.76674(11) 0.03496(19) Uani 1 1 d D
H2 H 0.550(5) 0.318(3) 0.705(5) 0.052 Uiso 0.50 1 d PD
O3 O -0.34065(13) -0.07931(14) 0.22928(12) 0.0438(2) Uani 1 1 d .
O4 O 0.34317(12) 0.18506(12) 0.50649(11) 0.03509(19) Uani 1 1 d D
H4 H 0.425(5) 0.223(5) 0.607(3) 0.053 Uiso 0.50 1 d PD
O5 O 0.82061(15) 0.41472(14) 0.26307(14) 0.0457(2) Uani 1 1 d .
N1 N 0.48338(16) 0.32093(15) 0.29181(15) 0.0361(2) Uani 1 1 d .
C1 C 1.09027(15) 0.40226(13) 0.98789(13) 0.02513(19) Uani 1 1 d .
C2 C 0.88910(15) 0.35118(13) 0.86671(13) 0.0265(2) Uani 1 1 d .
C3 C 0.79900(14) 0.44124(13) 0.87150(13) 0.0256(2) Uani 1 1 d .
C4 C -0.18193(16) -0.04190(13) 0.35038(13) 0.0280(2) Uani 1 1 d .
C5 C 0.00150(16) 0.05459(14) 0.35800(13) 0.0281(2) Uani 1 1 d .
C6 C 0.17662(15) 0.09834(13) 0.49649(13) 0.0273(2) Uani 1 1 d .
C7 C 0.5042(2) 0.20122(18) 0.19762(19) 0.0420(3) Uani 1 1 d .
H7A H 0.3769 0.1222 0.1046 0.050 Uiso 1 1 calc R
H7B H 0.5591 0.1417 0.2710 0.050 Uiso 1 1 calc R
C8 C 0.6361(2) 0.2918(2) 0.13225(19) 0.0451(3) Uani 1 1 d .
H8A H 0.6542 0.2140 0.0757 0.054 Uiso 1 1 calc R
H8B H 0.5744 0.3424 0.0508 0.054 Uiso 1 1 calc R
C9 C 0.7976(2) 0.53234(18) 0.3432(2) 0.0426(3) Uani 1 1 d .
H9A H 0.7341 0.5819 0.2617 0.051 Uiso 1 1 calc R
H9B H 0.9251 0.6187 0.4291 0.051 Uiso 1 1 calc R
C10 C 0.6769(2) 0.45415(18) 0.42252(17) 0.0387(3) Uani 1 1 d .
H10A H 0.7433 0.4097 0.5086 0.046 Uiso 1 1 calc R
H10B H 0.6607 0.5364 0.4748 0.046 Uiso 1 1 calc R
H1A H 0.414(3) 0.262(3) 0.341(3) 0.061(6) Uiso 1 1 d .
H1B H 0.414(3) 0.364(2) 0.215(3) 0.053(5) Uiso 1 1 d .
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
_geom_angle_site_symmetry_3
C3 O2 H2 116(3) .
C6 O4 H4 106(3) .
C9 O5 C8 110.04(11) .
C10 N1 C7 111.00(10) .
C10 N1 H1A 110.3(14) .
C7 N1 H1A 107.0(13) .
C10 N1 H1B 110.4(13) .
C7 N1 H1B 107.2(12) .
H1A N1 H1B 110.9(18) .
O1 C1 C2 123.61(10) .
O1 C1 C3 118.18(9) 2_767
C2 C1 C3 118.20(9) 2_767
C3 C2 C1 122.07(10) .
C3 C2 Cl1 120.69(8) .
C1 C2 Cl1 117.19(8) .
O2 C3 C2 127.34(10) .
O2 C3 C1 112.98(9) 2_767
C2 C3 C1 119.68(9) 2_767
O3 C4 C5 123.86(11) .
O3 C4 C6 117.77(10) 2_556
C5 C4 C6 118.36(9) 2_556
C6 C5 C4 122.58(10) .
C6 C5 Cl2 119.12(8) .
C4 C5 Cl2 118.30(8) .
O4 C6 C5 123.73(10) .
O4 C6 C4 117.22(9) 2_556
C5 C6 C4 119.04(9) 2_556
N1 C7 C8 109.62(12) .
N1 C7 H7A 109.7 .
C8 C7 H7A 109.7 .
N1 C7 H7B 109.7 .
C8 C7 H7B 109.7 .
H7A C7 H7B 108.2 .
O5 C8 C7 111.73(12) .
O5 C8 H8A 109.3 .
C7 C8 H8A 109.3 .
O5 C8 H8B 109.3 .
C7 C8 H8B 109.3 .
H8A C8 H8B 107.9 .
O5 C9 C10 111.10(12) .
O5 C9 H9A 109.4 .
C10 C9 H9A 109.4 .
O5 C9 H9B 109.4 .
C10 C9 H9B 109.4 .
H9A C9 H9B 108.0 .
N1 C10 C9 109.38(11) .
N1 C10 H10A 109.8 .
C9 C10 H10A 109.8 .
N1 C10 H10B 109.8 .
C9 C10 H10B 109.8 .
H10A C10 H10B 108.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7191(11) .
Cl2 C5 1.7222(11) .
O1 C1 1.2233(13) .
O2 C3 1.2901(12) .
O2 H2 0.807(19) .
O3 C4 1.2138(14) .
O4 C6 1.2988(13) .
O4 H4 0.823(19) .
O5 C9 1.4131(18) .
O5 C8 1.4154(18) .
N1 C10 1.4801(19) .
N1 C7 1.4908(19) .
N1 H1A 0.93(2) .
N1 H1B 0.92(2) .
C1 C2 1.4372(14) .
C1 C3 1.5175(15) 2_767
C2 C3 1.3580(15) .
C3 C1 1.5175(15) 2_767
C4 C5 1.4465(15) .
C4 C6 1.5211(15) 2_556
C5 C6 1.3536(14) .
C6 C4 1.5211(15) 2_556
C7 C8 1.510(2) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.5138(19) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
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_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -178.03(11) . .
C3 C1 C2 C3 2.33(17) 2_767 .
O1 C1 C2 Cl1 -0.36(15) . .
C3 C1 C2 Cl1 180.00(7) 2_767 .
C1 C2 C3 O2 177.49(11) . .
Cl1 C2 C3 O2 -0.10(17) . .
C1 C2 C3 C1 -2.36(17) . 2_767
Cl1 C2 C3 C1 -179.95(7) . 2_767
O3 C4 C5 C6 178.12(12) . .
C6 C4 C5 C6 -1.05(18) 2_556 .
O3 C4 C5 Cl2 -1.65(17) . .
C6 C4 C5 Cl2 179.19(8) 2_556 .
C4 C5 C6 O4 -179.89(11) . .
Cl2 C5 C6 O4 -0.13(16) . .
C4 C5 C6 C4 1.05(18) . 2_556
Cl2 C5 C6 C4 -179.18(8) . 2_556
C10 N1 C7 C8 -52.90(15) . .
C9 O5 C8 C7 -60.94(17) . .
N1 C7 C8 O5 56.26(17) . .
C8 O5 C9 C10 61.75(16) . .
C7 N1 C10 C9 53.85(15) . .
O5 C9 C10 N1 -58.33(15) . .
