#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:12:22 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180416 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/85/7208591.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_7208591
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                91.9362(7)
_cell_angle_beta                 116.6690(7)
_cell_angle_gamma                113.9804(7)
_cell_formula_units_Z            2
_cell_length_a                   8.62156(16)
_cell_length_b                   9.11162(16)
_cell_length_c                   9.19374(17)
_cell_measurement_reflns_used    15908
_cell_measurement_temperature    130(1)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     568.635(19)
_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      130(1)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0083
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16863
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.729
_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          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0227
_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)+(0.0361P)²+0.1944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                3186
_reflns_number_total             3310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cp41241a_2.txt
_cod_data_source_block           130K
_cod_database_code               7208591
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 0.76414(3) 0.16907(2) 0.70515(3) 0.01479(6) Uani 1 1 d .
Cl2 Cl -0.00132(3) 0.11689(3) 0.18041(3) 0.01720(6) Uani 1 1 d .
O1 O 1.17765(10) 0.32535(8) 0.98029(8) 0.01434(13) Uani 1 1 d .
O2 O 0.61776(9) 0.40893(8) 0.76701(8) 0.01414(12) Uani 1 1 d D
H2 H 0.545(3) 0.318(2) 0.696(3) 0.021 Uiso 0.62(3) 1 d PD
O3 O -0.34194(10) -0.07807(9) 0.22421(9) 0.01713(13) Uani 1 1 d .
O4 O 0.34777(9) 0.18437(8) 0.50803(8) 0.01400(12) Uani 1 1 d D
H4 H 0.429(5) 0.239(4) 0.609(3) 0.021 Uiso 0.38(3) 1 d PD
O5 O 0.82721(10) 0.41732(9) 0.26541(9) 0.01756(14) Uani 1 1 d .
N1 N 0.48559(11) 0.31986(10) 0.29285(10) 0.01453(14) Uani 1 1 d .
C1 C 1.09081(12) 0.40203(10) 0.98589(10) 0.01081(15) Uani 1 1 d .
C2 C 0.88690(12) 0.34916(10) 0.86477(10) 0.01113(15) Uani 1 1 d .
C3 C 0.79695(12) 0.43991(10) 0.87169(10) 0.01100(15) Uani 1 1 d .
C4 C -0.18280(12) -0.04161(10) 0.34776(11) 0.01154(15) Uani 1 1 d .
C5 C 0.00312(12) 0.05469(11) 0.35666(10) 0.01196(15) Uani 1 1 d .
C6 C 0.17939(12) 0.09817(10) 0.49733(11) 0.01155(15) Uani 1 1 d .
C7 C 0.50763(14) 0.19835(12) 0.19902(12) 0.01662(17) Uani 1 1 d .
H7A H 0.3770 0.1160 0.1040 0.020 Uiso 1 1 calc R
H7B H 0.5647 0.1376 0.2755 0.020 Uiso 1 1 calc R
C8 C 0.64057(14) 0.29160(12) 0.13261(12) 0.01759(17) Uani 1 1 d .
H8A H 0.6600 0.2123 0.0753 0.021 Uiso 1 1 calc R
H8B H 0.5770 0.3437 0.0485 0.021 Uiso 1 1 calc R
C9 C 0.80333(14) 0.53700(12) 0.34580(12) 0.01678(17) Uani 1 1 d .
H9A H 0.7378 0.5879 0.2615 0.020 Uiso 1 1 calc R
H9B H 0.9343 0.6266 0.4335 0.020 Uiso 1 1 calc R
C10 C 0.68150(13) 0.45635(12) 0.42599(11) 0.01539(16) Uani 1 1 d .
H10A H 0.7497 0.4104 0.5148 0.018 Uiso 1 1 calc R
H10B H 0.6638 0.5402 0.4789 0.018 Uiso 1 1 calc R
H1A H 0.415(2) 0.2662(19) 0.342(2) 0.027(4) Uiso 1 1 d .
H1B H 0.419(2) 0.3645(18) 0.2192(19) 0.023(3) 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 117.0(17) .
C6 O4 H4 107(3) .
C8 O5 C9 110.33(7) .
C10 N1 C7 111.31(7) .
C10 N1 H1A 109.1(10) .
C7 N1 H1A 110.1(10) .
C10 N1 H1B 109.1(9) .
C7 N1 H1B 109.1(9) .
H1A N1 H1B 108.1(13) .
O1 C1 C2 123.13(8) .
O1 C1 C3 118.59(7) 2_767
C2 C1 C3 118.27(7) 2_767
C3 C2 C1 121.58(8) .
C3 C2 Cl1 121.39(6) .
C1 C2 Cl1 116.98(6) .
O2 C3 C2 127.30(8) .
O2 C3 C1 112.60(7) 2_767
C2 C3 C1 120.10(7) 2_767
O3 C4 C5 123.68(8) .
O3 C4 C6 118.35(8) 2_556
C5 C4 C6 117.96(7) 2_556
C6 C5 C4 122.83(8) .
C6 C5 Cl2 119.32(6) .
C4 C5 Cl2 117.85(6) .
O4 C6 C5 123.85(8) .
O4 C6 C4 116.94(7) 2_556
C5 C6 C4 119.20(7) 2_556
N1 C7 C8 109.34(7) .
N1 C7 H7A 109.8 .
C8 C7 H7A 109.8 .
N1 C7 H7B 109.8 .
C8 C7 H7B 109.8 .
H7A C7 H7B 108.3 .
O5 C8 C7 111.35(7) .
O5 C8 H8A 109.4 .
C7 C8 H8A 109.4 .
O5 C8 H8B 109.4 .
C7 C8 H8B 109.4 .
H8A C8 H8B 108.0 .
O5 C9 C10 110.89(8) .
O5 C9 H9A 109.5 .
C10 C9 H9A 109.5 .
O5 C9 H9B 109.5 .
C10 C9 H9B 109.5 .
H9A C9 H9B 108.0 .
N1 C10 C9 108.91(7) .
N1 C10 H10A 109.9 .
C9 C10 H10A 109.9 .
N1 C10 H10B 109.9 .
C9 C10 H10B 109.9 .
H10A C10 H10B 108.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7314(8) .
Cl2 C5 1.7241(8) .
O1 C1 1.2283(10) .
O2 C3 1.2981(10) .
O2 H2 0.823(16) .
O3 C4 1.2199(10) .
O4 C6 1.2937(10) .
O4 H4 0.838(19) .
O5 C8 1.4268(11) .
O5 C9 1.4292(11) .
N1 C10 1.4939(12) .
N1 C7 1.5032(12) .
N1 H1A 0.912(16) .
N1 H1B 0.902(15) .
C1 C2 1.4425(11) .
C1 C3 1.5256(12) 2_767
C2 C3 1.3606(11) .
C3 C1 1.5256(12) 2_767
C4 C5 1.4423(12) .
C4 C6 1.5229(12) 2_556
C5 C6 1.3604(11) .
C6 C4 1.5229(12) 2_556
C7 C8 1.5101(13) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.5136(13) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
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 -177.92(8) . .
C3 C1 C2 C3 2.54(13) 2_767 .
O1 C1 C2 Cl1 -0.35(11) . .
C3 C1 C2 Cl1 -179.89(6) 2_767 .
C1 C2 C3 O2 177.17(8) . .
Cl1 C2 C3 O2 -0.29(13) . .
C1 C2 C3 C1 -2.59(13) . 2_767
Cl1 C2 C3 C1 179.95(6) . 2_767
O3 C4 C5 C6 178.07(9) . .
C6 C4 C5 C6 -0.85(14) 2_556 .
O3 C4 C5 Cl2 -1.66(12) . .
C6 C4 C5 Cl2 179.41(6) 2_556 .
C4 C5 C6 O4 179.98(8) . .
Cl2 C5 C6 O4 -0.29(12) . .
C4 C5 C6 C4 0.86(14) . 2_556
Cl2 C5 C6 C4 -179.41(6) . 2_556
C10 N1 C7 C8 -53.56(10) . .
C9 O5 C8 C7 -61.27(10) . .
N1 C7 C8 O5 56.48(10) . .
C8 O5 C9 C10 62.11(10) . .
C7 N1 C10 C9 54.34(9) . .
O5 C9 C10 N1 -58.29(10) . .
