#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:12:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180416 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/85/7208590.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_7208590
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                91.9171(7)
_cell_angle_beta                 116.6737(7)
_cell_angle_gamma                114.0287(7)
_cell_formula_units_Z            2
_cell_length_a                   8.62043(16)
_cell_length_b                   9.10670(16)
_cell_length_c                   9.19145(17)
_cell_measurement_reflns_used    15975
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     567.849(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      120(2)
_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            16851
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.732
_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         0.531
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0226
_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)+(0.0341P)²+0.2012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0618
_reflns_number_gt                3205
_reflns_number_total             3305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cp41241a_2.txt
_cod_data_source_block           120K
_cod_database_code               7208590
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 0.76399(3) 0.16891(2) 0.70492(3) 0.01386(6) Uani 1 1 d .
Cl2 Cl -0.00113(3) 0.11692(3) 0.18032(3) 0.01611(6) Uani 1 1 d .
O1 O 1.17757(10) 0.32538(8) 0.98016(8) 0.01352(12) Uani 1 1 d .
O2 O 0.61751(9) 0.40887(8) 0.76693(8) 0.01330(12) Uani 1 1 d D
H2 H 0.544(3) 0.318(2) 0.696(3) 0.020 Uiso 0.63(2) 1 d PD
O3 O -0.34212(10) -0.07796(9) 0.22402(8) 0.01604(13) Uani 1 1 d .
O4 O 0.34808(9) 0.18433(8) 0.50809(8) 0.01320(12) Uani 1 1 d D
H4 H 0.430(5) 0.239(4) 0.609(3) 0.020 Uiso 0.37(2) 1 d PD
O5 O 0.82758(10) 0.41761(9) 0.26549(9) 0.01646(13) Uani 1 1 d .
N1 N 0.48571(11) 0.31969(10) 0.29306(10) 0.01357(14) Uani 1 1 d .
C1 C 1.09083(12) 0.40206(10) 0.98583(10) 0.01026(14) Uani 1 1 d .
C2 C 0.88678(12) 0.34902(10) 0.86463(10) 0.01058(15) Uani 1 1 d .
C3 C 0.79679(12) 0.43982(10) 0.87168(10) 0.01050(15) Uani 1 1 d .
C4 C -0.18300(12) -0.04155(10) 0.34760(11) 0.01094(15) Uani 1 1 d .
C5 C 0.00317(12) 0.05466(10) 0.35661(10) 0.01134(15) Uani 1 1 d .
C6 C 0.17960(12) 0.09814(10) 0.49729(11) 0.01094(15) Uani 1 1 d .
C7 C 0.50787(14) 0.19819(11) 0.19926(12) 0.01556(16) Uani 1 1 d .
H7A H 0.3771 0.1157 0.1043 0.019 Uiso 1 1 calc R
H7B H 0.5651 0.1375 0.2759 0.019 Uiso 1 1 calc R
C8 C 0.64077(14) 0.29152(12) 0.13268(12) 0.01653(17) Uani 1 1 d .
H8A H 0.6602 0.2121 0.0754 0.020 Uiso 1 1 calc R
H8B H 0.5771 0.3435 0.0484 0.020 Uiso 1 1 calc R
C9 C 0.80365(14) 0.53738(12) 0.34584(12) 0.01573(16) Uani 1 1 d .
H9A H 0.7380 0.5882 0.2614 0.019 Uiso 1 1 calc R
H9B H 0.9347 0.6271 0.4335 0.019 Uiso 1 1 calc R
C10 C 0.68179(13) 0.45648(12) 0.42614(11) 0.01451(16) Uani 1 1 d .
H10A H 0.7502 0.4106 0.5150 0.017 Uiso 1 1 calc R
H10B H 0.6641 0.5404 0.4790 0.017 Uiso 1 1 calc R
H1A H 0.415(2) 0.2658(19) 0.3422(19) 0.026(4) Uiso 1 1 d .
H1B H 0.420(2) 0.3639(18) 0.2200(19) 0.022(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 117.4(16) .
C6 O4 H4 108(3) .
C8 O5 C9 110.34(7) .
C10 N1 C7 111.27(7) .
C10 N1 H1A 109.2(10) .
C7 N1 H1A 110.1(10) .
C10 N1 H1B 109.0(10) .
C7 N1 H1B 108.9(9) .
H1A N1 H1B 108.3(13) .
O1 C1 C2 123.10(8) .
O1 C1 C3 118.59(7) 2_767
C2 C1 C3 118.30(7) 2_767
C3 C2 C1 121.56(8) .
C3 C2 Cl1 121.42(6) .
C1 C2 Cl1 116.98(6) .
O2 C3 C2 127.31(8) .
O2 C3 C1 112.59(7) 2_767
C2 C3 C1 120.09(7) 2_767
O3 C4 C5 123.71(8) .
O3 C4 C6 118.38(8) 2_556
C5 C4 C6 117.90(7) 2_556
C6 C5 C4 122.91(7) .
C6 C5 Cl2 119.28(6) .
C4 C5 Cl2 117.81(6) .
O4 C6 C5 123.91(8) .
O4 C6 C4 116.90(7) 2_556
C5 C6 C4 119.19(7) 2_556
N1 C7 C8 109.39(7) .
N1 C7 H7A 109.8 .
C8 C7 H7A 109.8 .
N1 C7 H7B 109.8 .
C8 C7 H7B 109.8 .
H7A C7 H7B 108.2 .
O5 C8 C7 111.33(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 110.86(7) .
O5 C9 H9A 109.5 .
C10 C9 H9A 109.5 .
O5 C9 H9B 109.5 .
C10 C9 H9B 109.5 .
H9A C9 H9B 108.1 .
N1 C10 C9 108.94(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 1.7308(8) .
Cl2 C5 1.7243(8) .
O1 C1 1.2277(10) .
O2 C3 1.2984(10) .
O2 H2 0.822(16) .
O3 C4 1.2195(10) .
O4 C6 1.2932(10) .
O4 H4 0.838(19) .
O5 C8 1.4273(11) .
O5 C9 1.4295(11) .
N1 C10 1.4940(12) .
N1 C7 1.5034(12) .
N1 H1A 0.914(16) .
N1 H1B 0.891(15) .
C1 C2 1.4426(11) .
C1 C3 1.5251(12) 2_767
C2 C3 1.3615(11) .
C3 C1 1.5251(12) 2_767
C4 C5 1.4425(11) .
C4 C6 1.5241(12) 2_556
C5 C6 1.3607(11) .
C6 C4 1.5241(12) 2_556
C7 C8 1.5102(13) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.5143(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 -177.96(8) . .
C3 C1 C2 C3 2.51(13) 2_767 .
O1 C1 C2 Cl1 -0.39(11) . .
C3 C1 C2 Cl1 -179.92(6) 2_767 .
C1 C2 C3 O2 177.12(8) . .
Cl1 C2 C3 O2 -0.34(13) . .
C1 C2 C3 C1 -2.56(13) . 2_767
Cl1 C2 C3 C1 179.98(6) . 2_767
O3 C4 C5 C6 178.09(9) . .
C6 C4 C5 C6 -0.88(14) 2_556 .
O3 C4 C5 Cl2 -1.61(12) . .
C6 C4 C5 Cl2 179.42(6) 2_556 .
C4 C5 C6 O4 -179.97(8) . .
Cl2 C5 C6 O4 -0.27(12) . .
C4 C5 C6 C4 0.89(14) . 2_556
Cl2 C5 C6 C4 -179.41(6) . 2_556
C10 N1 C7 C8 -53.55(10) . .
C9 O5 C8 C7 -61.25(10) . .
N1 C7 C8 O5 56.47(10) . .
C8 O5 C9 C10 62.11(9) . .
C7 N1 C10 C9 54.34(9) . .
O5 C9 C10 N1 -58.31(10) . .
