#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:12:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180416 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/85/7208594.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_7208594
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_moiety
' C4 H10 N O, 0.5(C6 H1.18 Cl2 O4), 0.5(C6 H0.82 Cl2 O4)'
_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_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
_audit_update_record
;
2012-04-16 # Formatted by publCIF
;
_cell_angle_alpha                92.0264(7)
_cell_angle_beta                 116.6211(7)
_cell_angle_gamma                113.8289(7)
_cell_formula_units_Z            2
_cell_length_a                   8.62739(16)
_cell_length_b                   9.13846(17)
_cell_length_c                   9.20609(17)
_cell_measurement_reflns_used    15822
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     572.40(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      180(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0081
_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            16984
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.718
_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         0.440
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0234
_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)+(0.0362P)²+0.1931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0642
_reflns_number_gt                3167
_reflns_number_total             3342
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cp41241a_2.txt
_cod_data_source_block           180K
_cod_database_code               7208594
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 0.76485(3) 0.16995(3) 0.70614(3) 0.01968(6) Uani 1 1 d .
Cl2 Cl -0.00212(3) 0.11675(3) 0.18100(3) 0.02282(7) Uani 1 1 d .
O1 O 1.17767(10) 0.32533(9) 0.98097(9) 0.01862(13) Uani 1 1 d .
O2 O 0.61898(9) 0.40927(9) 0.76725(9) 0.01832(13) Uani 1 1 d D
H2 H 0.547(3) 0.319(2) 0.697(3) 0.027 Uiso 0.59(3) 1 d PD
O3 O -0.34138(10) -0.07839(9) 0.22511(9) 0.02245(15) Uani 1 1 d .
O4 O 0.34648(9) 0.18467(9) 0.50774(8) 0.01830(13) Uani 1 1 d D
H4 H 0.430(4) 0.237(4) 0.608(3) 0.027 Uiso 0.41(3) 1 d PD
O5 O 0.82566(10) 0.41625(9) 0.26494(10) 0.02338(15) Uani 1 1 d .
N1 N 0.48500(12) 0.32028(11) 0.29237(11) 0.01892(15) Uani 1 1 d .
C1 C 1.09066(12) 0.40189(10) 0.98617(10) 0.01371(15) Uani 1 1 d .
C2 C 0.88759(12) 0.34958(10) 0.86542(10) 0.01426(15) Uani 1 1 d .
C3 C 0.79741(12) 0.44027(10) 0.87186(10) 0.01406(15) Uani 1 1 d .
C4 C -0.18257(12) -0.04173(11) 0.34819(11) 0.01497(15) Uani 1 1 d .
C5 C 0.00278(12) 0.05466(11) 0.35692(11) 0.01531(15) Uani 1 1 d .
C6 C 0.17857(12) 0.09830(10) 0.49724(11) 0.01489(15) Uani 1 1 d .
C7 C 0.50672(15) 0.19914(12) 0.19833(13) 0.02183(18) Uani 1 1 d .
H7A H 0.3763 0.1176 0.1034 0.026 Uiso 1 1 calc R
H7B H 0.5633 0.1381 0.2744 0.026 Uiso 1 1 calc R
C8 C 0.63960(15) 0.29168(13) 0.13225(13) 0.02318(19) Uani 1 1 d .
H8A H 0.6589 0.2125 0.0749 0.028 Uiso 1 1 calc R
H8B H 0.5765 0.3440 0.0485 0.028 Uiso 1 1 calc R
C9 C 0.80191(15) 0.53549(12) 0.34532(13) 0.02208(18) Uani 1 1 d .
H9A H 0.7368 0.5866 0.2613 0.026 Uiso 1 1 calc R
H9B H 0.9325 0.6244 0.4330 0.026 Uiso 1 1 calc R
C10 C 0.68019(14) 0.45554(12) 0.42513(12) 0.02010(17) Uani 1 1 d .
H10A H 0.7480 0.4095 0.5137 0.024 Uiso 1 1 calc R
H10B H 0.6626 0.5393 0.4780 0.024 Uiso 1 1 calc R
H1A H 0.416(2) 0.2672(19) 0.342(2) 0.033(4) Uiso 1 1 d .
H1B H 0.418(2) 0.3647(18) 0.2188(19) 0.027(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(18) .
C6 O4 H4 109(2) .
C8 O5 C9 110.31(7) .
C10 N1 C7 111.34(7) .
C10 N1 H1A 108.7(10) .
C7 N1 H1A 110.1(10) .
C10 N1 H1B 109.4(9) .
C7 N1 H1B 108.9(9) .
H1A N1 H1B 108.5(13) .
O1 C1 C2 123.23(8) .
O1 C1 C3 118.51(7) 2_767
C2 C1 C3 118.26(7) 2_767
C3 C2 C1 121.67(8) .
C3 C2 Cl1 121.19(7) .
C1 C2 Cl1 117.09(6) .
O2 C3 C2 127.19(8) .
O2 C3 C1 112.79(7) 2_767
C2 C3 C1 120.02(7) 2_767
O3 C4 C5 123.72(8) .
O3 C4 C6 118.36(8) 2_556
C5 C4 C6 117.92(7) 2_556
C6 C5 C4 122.77(8) .
C6 C5 Cl2 119.38(7) .
C4 C5 Cl2 117.85(6) .
O4 C6 C5 123.77(8) .
O4 C6 C4 116.92(7) 2_556
C5 C6 C4 119.30(7) 2_556
N1 C7 C8 109.37(8) .
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 111.32(8) .
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 110.94(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 108.94(8) .
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 1.7320(9) .
Cl2 C5 1.7232(9) .
O1 C1 1.2287(10) .
O2 C3 1.2951(10) .
O2 H2 0.820(17) .
O3 C4 1.2183(11) .
O4 C6 1.2946(10) .
O4 H4 0.835(19) .
O5 C8 1.4257(12) .
O5 C9 1.4270(12) .
N1 C10 1.4914(13) .
N1 C7 1.5018(13) .
N1 H1A 0.910(16) .
N1 H1B 0.901(15) .
C1 C2 1.4401(11) .
C1 C3 1.5269(12) 2_767
C2 C3 1.3619(12) .
C3 C1 1.5269(12) 2_767
C4 C5 1.4427(12) .
C4 C6 1.5218(12) 2_556
C5 C6 1.3590(12) .
C6 C4 1.5218(12) 2_556
C7 C8 1.5092(14) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.5120(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 -177.90(8) . .
C3 C1 C2 C3 2.49(13) 2_767 .
O1 C1 C2 Cl1 -0.33(12) . .
C3 C1 C2 Cl1 -179.94(6) 2_767 .
C1 C2 C3 O2 177.17(8) . .
Cl1 C2 C3 O2 -0.30(13) . .
C1 C2 C3 C1 -2.54(14) . 2_767
Cl1 C2 C3 C1 179.99(6) . 2_767
O3 C4 C5 C6 178.03(9) . .
C6 C4 C5 C6 -1.02(14) 2_556 .
O3 C4 C5 Cl2 -1.63(13) . .
C6 C4 C5 Cl2 179.33(6) 2_556 .
C4 C5 C6 O4 180.00(8) . .
Cl2 C5 C6 O4 -0.36(13) . .
C4 C5 C6 C4 1.03(14) . 2_556
Cl2 C5 C6 C4 -179.32(6) . 2_556
C10 N1 C7 C8 -53.46(10) . .
C9 O5 C8 C7 -61.26(11) . .
N1 C7 C8 O5 56.42(11) . .
C8 O5 C9 C10 62.15(10) . .
C7 N1 C10 C9 54.23(10) . .
O5 C9 C10 N1 -58.27(10) . .
