# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The Owner Societies 2012
data_global
_journal_name_full Phys.Chem.Chem.Phys.(PCCP)
_journal_coden_cambridge 1326
loop_
_publ_author_name
_publ_author_address
Y.Tobu
;
Department of Chemistry
University of Tukuba
Tukuba 305-8571
Japan
;
R.Ikeda
;
Department of Chemistry
University of Tukuba
Tukuba 305-8571
Japan
;
K.Gotoh
;
Department of Chemistry and Biochemistry
Numazu National College of Technology
Numazu 410-8501
Japan
;
H.Ishida
;
Department of Chemistry
Faculty of Science
Okayama University
Okayama 700-8530
Japan
;
T.Asaji
;
Department of Chemistry
Faculty of Science
Okayama University
Okayama 700-8530
Japan
;
_publ_contact_author_email ishidah@cc.okayama-u.ac.jp
#TrackingRef '- 114K.cif'
_publ_contact_author_name 'Ishida, Hiroyuki'
data_114K
_database_code_depnum_ccdc_archive 'CCDC 876320'
_chemical_name_common 'morpholinium hydrogen chloranilete'
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C10 H11 Cl2 N O5'
_chemical_formula_weight 296.10
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.61998(16)
_cell_length_b 9.10428(16)
_cell_length_c 9.19040(17)
_cell_angle_alpha 91.9088(7)
_cell_angle_beta 116.6760(7)
_cell_angle_gamma 114.0492(7)
_cell_volume 567.491(19)
_cell_formula_units_Z 2
_cell_measurement_temperature 114(1)
_cell_measurement_reflns_used 15964
_cell_measurement_theta_min 3.1
_cell_measurement_theta_max 30.1
_exptl_crystal_description block
_exptl_crystal_colour brown
_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
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.733
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.585
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_absorpt_correction_T_min 0.828
_exptl_absorpt_correction_T_max 0.900
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 114(2)
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16837
_diffrn_reflns_av_R_equivalents 0.0147
_diffrn_reflns_av_sigmaI/netI 0.0084
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 3.10
_diffrn_reflns_theta_max 30.03
_reflns_number_total 3303
_reflns_number_gt 3200
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_cell_refinement PROCESS-AUTO
_computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.2192P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3303
_refine_ls_number_parameters 178
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0232
_refine_ls_R_factor_gt 0.0226
_refine_ls_wR_factor_ref 0.0607
_refine_ls_wR_factor_gt 0.0603
_refine_ls_goodness_of_fit_ref 1.072
_refine_ls_restrained_S_all 1.072
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.76393(3) 0.16885(2) 0.70482(3) 0.01338(6) Uani 1 1 d . . .
Cl2 Cl -0.00105(3) 0.11695(3) 0.18027(3) 0.01557(6) Uani 1 1 d . . .
O1 O 1.17759(9) 0.32545(8) 0.98011(8) 0.01312(12) Uani 1 1 d . . .
O2 O 0.61736(9) 0.40882(8) 0.76686(8) 0.01287(12) Uani 1 1 d D . .
H2 H 0.544(3) 0.318(2) 0.696(3) 0.019 Uiso 0.63(2) 1 d PD . .
O3 O -0.34222(10) -0.07795(9) 0.22394(8) 0.01554(13) Uani 1 1 d . . .
O4 O 0.34827(9) 0.18429(8) 0.50812(8) 0.01280(12) Uani 1 1 d D . .
H4 H 0.431(5) 0.239(4) 0.609(3) 0.019 Uiso 0.37(2) 1 d PD . .
O5 O 0.82780(10) 0.41780(9) 0.26557(9) 0.01592(13) Uani 1 1 d . . .
N1 N 0.48576(11) 0.31963(10) 0.29314(10) 0.01313(14) Uani 1 1 d . . .
C1 C 1.09085(12) 0.40211(10) 0.98585(10) 0.00996(14) Uani 1 1 d . . .
C2 C 0.88668(12) 0.34900(10) 0.86453(10) 0.01032(15) Uani 1 1 d . . .
C3 C 0.79678(12) 0.43975(10) 0.87166(10) 0.01029(15) Uani 1 1 d . . .
C4 C -0.18299(12) -0.04153(10) 0.34759(11) 0.01061(15) Uani 1 1 d . . .
C5 C 0.00320(12) 0.05465(10) 0.35657(10) 0.01109(15) Uani 1 1 d . . .
C6 C 0.17975(12) 0.09817(10) 0.49733(11) 0.01066(15) Uani 1 1 d . . .
C7 C 0.50796(14) 0.19813(11) 0.19937(12) 0.01513(16) Uani 1 1 d . . .
H7A H 0.3772 0.1155 0.1044 0.018 Uiso 1 1 calc R . .
H7B H 0.5652 0.1375 0.2760 0.018 Uiso 1 1 calc R . .
C8 C 0.64084(14) 0.29151(12) 0.13270(12) 0.01604(17) Uani 1 1 d . . .
H8A H 0.6603 0.2121 0.0755 0.019 Uiso 1 1 calc R . .
H8B H 0.5771 0.3435 0.0484 0.019 Uiso 1 1 calc R . .
C9 C 0.80378(14) 0.53754(11) 0.34589(12) 0.01521(16) Uani 1 1 d . . .
H9A H 0.7381 0.5883 0.2614 0.018 Uiso 1 1 calc R . .
H9B H 0.9348 0.6274 0.4336 0.018 Uiso 1 1 calc R . .
C10 C 0.68187(13) 0.45656(12) 0.42620(11) 0.01400(16) Uani 1 1 d . . .
H10A H 0.7503 0.4108 0.5152 0.017 Uiso 1 1 calc R . .
H10B H 0.6641 0.5405 0.4790 0.017 Uiso 1 1 calc R . .
H1A H 0.415(2) 0.2660(19) 0.3417(19) 0.026(4) Uiso 1 1 d . . .
H1B H 0.420(2) 0.3636(18) 0.2199(19) 0.022(3) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01185(10) 0.01133(10) 0.01297(10) -0.00023(7) 0.00413(8) 0.00476(7)
Cl2 0.01238(10) 0.01986(11) 0.01170(10) 0.00730(8) 0.00592(8) 0.00525(8)
O1 0.0126(3) 0.0146(3) 0.0140(3) 0.0041(2) 0.0064(2) 0.0084(2)
O2 0.0079(3) 0.0134(3) 0.0129(3) 0.0012(2) 0.0024(2) 0.0046(2)
O3 0.0098(3) 0.0194(3) 0.0128(3) 0.0049(2) 0.0035(2) 0.0055(2)
O4 0.0078(3) 0.0148(3) 0.0113(3) 0.0020(2) 0.0044(2) 0.0023(2)
O5 0.0116(3) 0.0173(3) 0.0182(3) 0.0017(2) 0.0084(3) 0.0055(2)
N1 0.0113(3) 0.0166(3) 0.0147(3) 0.0067(3) 0.0079(3) 0.0075(3)
C1 0.0099(3) 0.0104(3) 0.0098(3) 0.0039(3) 0.0055(3) 0.0043(3)
C2 0.0091(3) 0.0099(3) 0.0094(3) 0.0013(3) 0.0037(3) 0.0034(3)
C3 0.0091(3) 0.0109(3) 0.0100(3) 0.0033(3) 0.0049(3) 0.0039(3)
C4 0.0099(3) 0.0101(3) 0.0107(4) 0.0022(3) 0.0048(3) 0.0043(3)
C5 0.0103(4) 0.0121(4) 0.0099(3) 0.0039(3) 0.0052(3) 0.0042(3)
C6 0.0103(4) 0.0098(3) 0.0111(4) 0.0021(3) 0.0053(3) 0.0044(3)
C7 0.0144(4) 0.0136(4) 0.0164(4) 0.0027(3) 0.0085(3) 0.0050(3)
C8 0.0150(4) 0.0178(4) 0.0140(4) 0.0018(3) 0.0085(3) 0.0055(3)
C9 0.0144(4) 0.0138(4) 0.0173(4) 0.0032(3) 0.0092(3) 0.0053(3)
C10 0.0139(4) 0.0158(4) 0.0130(4) 0.0036(3) 0.0072(3) 0.0072(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7306(8) . ?
Cl2 C5 1.7244(8) . ?
O1 C1 1.2277(10) . ?
O2 C3 1.2994(10) . ?
O2 H2 0.825(16) . ?
O3 C4 1.2201(10) . ?
O4 C6 1.2930(10) . ?
O4 H4 0.836(19) . ?
O5 C8 1.4281(11) . ?
O5 C9 1.4296(11) . ?
N1 C10 1.4940(12) . ?
N1 C7 1.5033(12) . ?
N1 H1A 0.908(16) . ?
N1 H1B 0.892(15) . ?
C1 C2 1.4433(11) . ?
C1 C3 1.5248(12) 2_767 ?
C2 C3 1.3606(11) . ?
C3 C1 1.5248(12) 2_767 ?
C4 C5 1.4423(11) . ?
C4 C6 1.5242(12) 2_556 ?
C5 C6 1.3613(11) . ?
C6 C4 1.5242(12) 2_556 ?
C7 C8 1.5104(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5145(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 117.0(16) . . ?
C6 O4 H4 108(3) . . ?
C8 O5 C9 110.32(7) . . ?
C10 N1 C7 111.27(7) . . ?
C10 N1 H1A 109.3(10) . . ?
C7 N1 H1A 110.1(10) . . ?
C10 N1 H1B 109.1(10) . . ?
C7 N1 H1B 108.9(9) . . ?
H1A N1 H1B 108.0(13) . . ?
O1 C1 C2 123.08(8) . . ?
O1 C1 C3 118.62(7) . 2_767 ?
C2 C1 C3 118.30(7) . 2_767 ?
C3 C2 C1 121.53(8) . . ?
C3 C2 Cl1 121.45(6) . . ?
C1 C2 Cl1 116.98(6) . . ?
O2 C3 C2 127.33(8) . . ?
O2 C3 C1 112.54(7) . 2_767 ?
C2 C3 C1 120.12(7) . 2_767 ?
O3 C4 C5 123.71(8) . . ?
O3 C4 C6 118.35(7) . 2_556 ?
C5 C4 C6 117.94(7) . 2_556 ?
C6 C5 C4 122.91(7) . . ?
C6 C5 Cl2 119.27(6) . . ?
C4 C5 Cl2 117.82(6) . . ?
O4 C6 C5 123.93(8) . . ?
O4 C6 C4 116.92(7) . 2_556 ?
C5 C6 C4 119.15(7) . 2_556 ?
N1 C7 C8 109.41(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 110.88(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 108.95(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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.95(8) . . . . ?
C3 C1 C2 C3 2.47(13) 2_767 . . . ?
O1 C1 C2 Cl1 -0.35(11) . . . . ?
C3 C1 C2 Cl1 -179.92(6) 2_767 . . . ?
C1 C2 C3 O2 177.13(8) . . . . ?
Cl1 C2 C3 O2 -0.37(13) . . . . ?
C1 C2 C3 C1 -2.52(13) . . . 2_767 ?
Cl1 C2 C3 C1 179.98(6) . . . 2_767 ?
O3 C4 C5 C6 178.08(9) . . . . ?
C6 C4 C5 C6 -0.89(14) 2_556 . . . ?
O3 C4 C5 Cl2 -1.60(12) . . . . ?
C6 C4 C5 Cl2 179.43(6) 2_556 . . . ?
C4 C5 C6 O4 -179.98(8) . . . . ?
Cl2 C5 C6 O4 -0.31(12) . . . . ?
C4 C5 C6 C4 0.90(14) . . . 2_556 ?
Cl2 C5 C6 C4 -179.43(6) . . . 2_556 ?
C10 N1 C7 C8 -53.55(10) . . . . ?
C9 O5 C8 C7 -61.23(10) . . . . ?
N1 C7 C8 O5 56.47(10) . . . . ?
C8 O5 C9 C10 62.08(9) . . . . ?
C7 N1 C10 C9 54.33(9) . . . . ?
O5 C9 C10 N1 -58.30(9) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.551
_refine_diff_density_min -0.219
_refine_diff_density_rms 0.058
# Attachment '- 120K.cif'
data_120K
_database_code_depnum_ccdc_archive 'CCDC 876321'
_chemical_name_common 'morpholinium hydrogen chloranilete'
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C10 H11 Cl2 N O5'
_chemical_formula_weight 296.10
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.62043(16)
_cell_length_b 9.10670(16)
_cell_length_c 9.19145(17)
_cell_angle_alpha 91.9171(7)
_cell_angle_beta 116.6737(7)
_cell_angle_gamma 114.0287(7)
_cell_volume 567.849(19)
_cell_formula_units_Z 2
_cell_measurement_temperature 120(1)
_cell_measurement_reflns_used 15975
_cell_measurement_theta_min 3.1
_cell_measurement_theta_max 30.1
_exptl_crystal_description block
_exptl_crystal_colour brown
_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
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.732
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.585
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_absorpt_correction_T_min 0.826
_exptl_absorpt_correction_T_max 0.900
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16851
_diffrn_reflns_av_R_equivalents 0.0147
_diffrn_reflns_av_sigmaI/netI 0.0083
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 3.10
_diffrn_reflns_theta_max 30.03
_reflns_number_total 3305
_reflns_number_gt 3205
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_cell_refinement PROCESS-AUTO
_computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.2012P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3305
_refine_ls_number_parameters 178
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0232
_refine_ls_R_factor_gt 0.0226
_refine_ls_wR_factor_ref 0.0618
_refine_ls_wR_factor_gt 0.0614
_refine_ls_goodness_of_fit_ref 1.091
_refine_ls_restrained_S_all 1.090
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
_atom_site_disorder_assembly
_atom_site_disorder_group
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01225(10) 0.01178(10) 0.01340(10) -0.00023(7) 0.00426(8) 0.00494(8)
Cl2 0.01284(10) 0.02054(11) 0.01202(10) 0.00754(8) 0.00608(8) 0.00541(8)
O1 0.0129(3) 0.0152(3) 0.0143(3) 0.0041(2) 0.0065(2) 0.0087(2)
O2 0.0082(3) 0.0138(3) 0.0133(3) 0.0012(2) 0.0025(2) 0.0048(2)
O3 0.0101(3) 0.0201(3) 0.0132(3) 0.0051(2) 0.0036(2) 0.0056(2)
O4 0.0081(3) 0.0154(3) 0.0115(3) 0.0021(2) 0.0045(2) 0.0023(2)
O5 0.0119(3) 0.0180(3) 0.0188(3) 0.0018(2) 0.0087(3) 0.0056(2)
N1 0.0115(3) 0.0173(3) 0.0150(3) 0.0070(3) 0.0080(3) 0.0078(3)
C1 0.0101(3) 0.0107(3) 0.0099(3) 0.0040(3) 0.0054(3) 0.0044(3)
C2 0.0093(3) 0.0102(3) 0.0096(3) 0.0014(3) 0.0038(3) 0.0035(3)
C3 0.0093(3) 0.0111(3) 0.0103(3) 0.0034(3) 0.0051(3) 0.0039(3)
C4 0.0102(3) 0.0105(3) 0.0110(4) 0.0023(3) 0.0050(3) 0.0045(3)
C5 0.0106(4) 0.0123(4) 0.0101(3) 0.0040(3) 0.0053(3) 0.0044(3)
C6 0.0106(4) 0.0101(3) 0.0113(4) 0.0021(3) 0.0054(3) 0.0045(3)
C7 0.0148(4) 0.0140(4) 0.0167(4) 0.0027(3) 0.0087(3) 0.0052(3)
C8 0.0155(4) 0.0183(4) 0.0145(4) 0.0020(3) 0.0088(3) 0.0057(3)
C9 0.0146(4) 0.0143(4) 0.0181(4) 0.0033(3) 0.0095(3) 0.0054(3)
C10 0.0144(4) 0.0164(4) 0.0135(4) 0.0037(3) 0.0075(3) 0.0075(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.531
_refine_diff_density_min -0.236
_refine_diff_density_rms 0.057
# Attachment '- 130K.cif'
data_130K
_database_code_depnum_ccdc_archive 'CCDC 876322'
_chemical_name_common 'morpholinium hydrogen chloranilete'
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C10 H11 Cl2 N O5'
_chemical_formula_weight 296.10
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.62156(16)
_cell_length_b 9.11162(16)
_cell_length_c 9.19374(17)
_cell_angle_alpha 91.9362(7)
_cell_angle_beta 116.6690(7)
_cell_angle_gamma 113.9804(7)
_cell_volume 568.635(19)
_cell_formula_units_Z 2
_cell_measurement_temperature 130(1)
_cell_measurement_reflns_used 15908
_cell_measurement_theta_min 3.1
_cell_measurement_theta_max 30.1
_exptl_crystal_description block
_exptl_crystal_colour brown
_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
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.729
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.584
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_absorpt_correction_T_min 0.832
_exptl_absorpt_correction_T_max 0.900
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 130(1)
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16863
_diffrn_reflns_av_R_equivalents 0.0147
_diffrn_reflns_av_sigmaI/netI 0.0083
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 3.10
_diffrn_reflns_theta_max 30.03
_reflns_number_total 3310
_reflns_number_gt 3186
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_cell_refinement PROCESS-AUTO
_computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.1944P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3310
_refine_ls_number_parameters 178
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0235
_refine_ls_R_factor_gt 0.0227
_refine_ls_wR_factor_ref 0.0631
_refine_ls_wR_factor_gt 0.0624
_refine_ls_goodness_of_fit_ref 1.076
_refine_ls_restrained_S_all 1.076
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
_atom_site_disorder_assembly
_atom_site_disorder_group
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01306(10) 0.01251(10) 0.01435(10) -0.00026(7) 0.00451(8) 0.00527(8)
Cl2 0.01367(10) 0.02195(11) 0.01279(10) 0.00810(8) 0.00642(8) 0.00573(8)
O1 0.0136(3) 0.0161(3) 0.0152(3) 0.0042(2) 0.0068(2) 0.0091(2)
O2 0.0085(3) 0.0148(3) 0.0141(3) 0.0013(2) 0.0025(2) 0.0051(2)
O3 0.0106(3) 0.0215(3) 0.0141(3) 0.0055(2) 0.0038(2) 0.0059(2)
O4 0.0086(3) 0.0165(3) 0.0121(3) 0.0023(2) 0.0047(2) 0.0024(2)
O5 0.0127(3) 0.0193(3) 0.0202(3) 0.0021(3) 0.0094(3) 0.0061(3)
N1 0.0125(3) 0.0185(4) 0.0163(3) 0.0078(3) 0.0088(3) 0.0085(3)
C1 0.0106(3) 0.0114(3) 0.0107(3) 0.0043(3) 0.0059(3) 0.0048(3)
C2 0.0098(3) 0.0107(3) 0.0103(3) 0.0014(3) 0.0042(3) 0.0038(3)
C3 0.0098(3) 0.0116(3) 0.0109(3) 0.0036(3) 0.0055(3) 0.0041(3)
C4 0.0109(3) 0.0112(3) 0.0114(4) 0.0025(3) 0.0051(3) 0.0048(3)
C5 0.0111(4) 0.0131(4) 0.0105(3) 0.0040(3) 0.0055(3) 0.0046(3)
C6 0.0110(4) 0.0106(3) 0.0120(4) 0.0021(3) 0.0055(3) 0.0047(3)
C7 0.0157(4) 0.0151(4) 0.0177(4) 0.0030(3) 0.0092(3) 0.0054(3)
C8 0.0164(4) 0.0196(4) 0.0154(4) 0.0020(3) 0.0094(3) 0.0060(3)
C9 0.0155(4) 0.0152(4) 0.0192(4) 0.0035(3) 0.0100(3) 0.0057(3)
C10 0.0153(4) 0.0177(4) 0.0142(4) 0.0041(3) 0.0080(3) 0.0082(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.511
_refine_diff_density_min -0.204
_refine_diff_density_rms 0.057
# Attachment '- 145K.cif'
data_145K
_database_code_depnum_ccdc_archive 'CCDC 876323'
_chemical_name_common 'morpholinium hydrogen chloranilete'
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C10 H11 Cl2 N O5'
_chemical_formula_weight 296.10
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.62366(16)
_cell_length_b 9.11968(17)
_cell_length_c 9.19716(17)
_cell_angle_alpha 91.9817(7)
_cell_angle_beta 116.6494(7)
_cell_angle_gamma 113.9058(7)
_cell_volume 569.92(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 145(1)
_cell_measurement_reflns_used 15898
_cell_measurement_theta_min 3.1
_cell_measurement_theta_max 30.1
_exptl_crystal_description block
_exptl_crystal_colour brown
_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
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.725
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.583
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_absorpt_correction_T_min 0.829
_exptl_absorpt_correction_T_max 0.901
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 145(1)
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16941
_diffrn_reflns_av_R_equivalents 0.0143
_diffrn_reflns_av_sigmaI/netI 0.0082
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 3.09
_diffrn_reflns_theta_max 30.03
_reflns_number_total 3327
_reflns_number_gt 3171
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_cell_refinement PROCESS-AUTO
_computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.1977P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3327
_refine_ls_number_parameters 178
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0238
_refine_ls_R_factor_gt 0.0226
_refine_ls_wR_factor_ref 0.0627
_refine_ls_wR_factor_gt 0.0617
_refine_ls_goodness_of_fit_ref 1.075
_refine_ls_restrained_S_all 1.075
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.76437(3) 0.16933(3) 0.70551(3) 0.01632(6) Uani 1 1 d . . .
Cl2 Cl -0.00158(3) 0.11683(3) 0.18059(3) 0.01894(6) Uani 1 1 d . . .
O1 O 1.17762(10) 0.32529(8) 0.98045(8) 0.01560(13) Uani 1 1 d . . .
O2 O 0.61822(9) 0.40910(8) 0.76713(8) 0.01543(13) Uani 1 1 d D . .
H2 H 0.546(3) 0.318(2) 0.697(3) 0.023 Uiso 0.61(3) 1 d PD . .
O3 O -0.34174(10) -0.07820(9) 0.22444(9) 0.01876(14) Uani 1 1 d . . .
O4 O 0.34730(9) 0.18450(8) 0.50794(8) 0.01538(13) Uani 1 1 d D . .
H4 H 0.430(4) 0.238(4) 0.609(3) 0.023 Uiso 0.39(3) 1 d PD . .
O5 O 0.82667(10) 0.41691(9) 0.26525(9) 0.01930(14) Uani 1 1 d . . .
N1 N 0.48538(12) 0.32002(10) 0.29267(10) 0.01586(15) Uani 1 1 d . . .
C1 C 1.09074(12) 0.40197(10) 0.98594(10) 0.01168(15) Uani 1 1 d . . .
C2 C 0.88716(12) 0.34931(10) 0.86496(10) 0.01213(15) Uani 1 1 d . . .
C3 C 0.79707(12) 0.44002(10) 0.87183(10) 0.01199(15) Uani 1 1 d . . .
C4 C -0.18274(12) -0.04170(10) 0.34786(11) 0.01261(15) Uani 1 1 d . . .
C5 C 0.00304(12) 0.05464(11) 0.35678(10) 0.01301(15) Uani 1 1 d . . .
C6 C 0.17907(12) 0.09823(10) 0.49729(11) 0.01263(15) Uani 1 1 d . . .
C7 C 0.50736(14) 0.19870(12) 0.19873(12) 0.01825(17) Uani 1 1 d . . .
H7A H 0.3768 0.1167 0.1037 0.022 Uiso 1 1 calc R . .
H7B H 0.5642 0.1378 0.2751 0.022 Uiso 1 1 calc R . .
C8 C 0.64020(14) 0.29164(12) 0.13244(12) 0.01934(18) Uani 1 1 d . . .
H8A H 0.6595 0.2123 0.0750 0.023 Uiso 1 1 calc R . .
H8B H 0.5768 0.3439 0.0485 0.023 Uiso 1 1 calc R . .
C9 C 0.80279(14) 0.53643(12) 0.34562(12) 0.01842(17) Uani 1 1 d . . .
H9A H 0.7374 0.5874 0.2614 0.022 Uiso 1 1 calc R . .
H9B H 0.9336 0.6258 0.4333 0.022 Uiso 1 1 calc R . .
C10 C 0.68105(14) 0.45602(12) 0.42574(12) 0.01681(16) Uani 1 1 d . . .
H10A H 0.7491 0.4100 0.5144 0.020 Uiso 1 1 calc R . .
H10B H 0.6634 0.5399 0.4787 0.020 Uiso 1 1 calc R . .
H1A H 0.415(2) 0.2669(19) 0.343(2) 0.029(4) Uiso 1 1 d . . .
H1B H 0.419(2) 0.3642(18) 0.2192(19) 0.026(4) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01433(10) 0.01385(10) 0.01580(10) -0.00031(7) 0.00488(8) 0.00582(8)
Cl2 0.01504(10) 0.02420(12) 0.01398(10) 0.00892(8) 0.00695(8) 0.00628(8)
O1 0.0147(3) 0.0176(3) 0.0166(3) 0.0046(2) 0.0073(2) 0.0100(2)
O2 0.0094(3) 0.0161(3) 0.0155(3) 0.0016(2) 0.0028(2) 0.0057(2)
O3 0.0114(3) 0.0239(3) 0.0152(3) 0.0063(3) 0.0040(2) 0.0064(3)
O4 0.0095(3) 0.0181(3) 0.0134(3) 0.0027(2) 0.0053(2) 0.0027(2)
O5 0.0139(3) 0.0214(3) 0.0221(3) 0.0023(3) 0.0104(3) 0.0066(3)
N1 0.0135(3) 0.0204(4) 0.0177(4) 0.0087(3) 0.0095(3) 0.0093(3)
C1 0.0112(3) 0.0126(3) 0.0117(3) 0.0048(3) 0.0063(3) 0.0053(3)
C2 0.0105(3) 0.0118(3) 0.0113(3) 0.0017(3) 0.0045(3) 0.0041(3)
C3 0.0105(3) 0.0127(3) 0.0121(3) 0.0040(3) 0.0059(3) 0.0046(3)
C4 0.0116(4) 0.0123(3) 0.0126(4) 0.0029(3) 0.0055(3) 0.0052(3)
C5 0.0118(4) 0.0144(4) 0.0113(4) 0.0043(3) 0.0057(3) 0.0050(3)
C6 0.0120(4) 0.0118(3) 0.0127(4) 0.0023(3) 0.0058(3) 0.0051(3)
C7 0.0168(4) 0.0167(4) 0.0194(4) 0.0033(3) 0.0098(3) 0.0058(3)
C8 0.0179(4) 0.0217(4) 0.0170(4) 0.0023(3) 0.0103(3) 0.0066(3)
C9 0.0169(4) 0.0168(4) 0.0209(4) 0.0039(3) 0.0108(3) 0.0061(3)
C10 0.0169(4) 0.0195(4) 0.0156(4) 0.0046(3) 0.0089(3) 0.0092(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7314(9) . ?
Cl2 C5 1.7242(9) . ?
O1 C1 1.2284(10) . ?
O2 C3 1.2969(10) . ?
O2 H2 0.821(17) . ?
O3 C4 1.2195(11) . ?
O4 C6 1.2944(10) . ?
O4 H4 0.835(19) . ?
O5 C8 1.4267(12) . ?
O5 C9 1.4281(12) . ?
N1 C10 1.4932(12) . ?
N1 C7 1.5024(12) . ?
N1 H1A 0.917(16) . ?
N1 H1B 0.897(15) . ?
C1 C2 1.4416(11) . ?
C1 C3 1.5258(12) 2_767 ?
C2 C3 1.3613(11) . ?
C3 C1 1.5258(12) 2_767 ?
C4 C5 1.4428(12) . ?
C4 C6 1.5227(12) 2_556 ?
C5 C6 1.3594(11) . ?
C6 C4 1.5227(12) 2_556 ?
C7 C8 1.5092(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5133(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 116.9(17) . . ?
C6 O4 H4 108(3) . . ?
C8 O5 C9 110.28(7) . . ?
C10 N1 C7 111.29(7) . . ?
C10 N1 H1A 108.6(10) . . ?
C7 N1 H1A 110.4(10) . . ?
C10 N1 H1B 109.3(10) . . ?
C7 N1 H1B 108.8(9) . . ?
H1A N1 H1B 108.3(13) . . ?
O1 C1 C2 123.16(8) . . ?
O1 C1 C3 118.55(7) . 2_767 ?
C2 C1 C3 118.29(7) . 2_767 ?
C3 C2 C1 121.61(8) . . ?
C3 C2 Cl1 121.31(6) . . ?
C1 C2 Cl1 117.03(6) . . ?
O2 C3 C2 127.25(8) . . ?
O2 C3 C1 112.69(7) . 2_767 ?
C2 C3 C1 120.05(7) . 2_767 ?
O3 C4 C5 123.71(8) . . ?
O3 C4 C6 118.37(8) . 2_556 ?
C5 C4 C6 117.91(7) . 2_556 ?
C6 C5 C4 122.84(8) . . ?
C6 C5 Cl2 119.33(7) . . ?
C4 C5 Cl2 117.82(6) . . ?
O4 C6 C5 123.84(8) . . ?
O4 C6 C4 116.92(7) . 2_556 ?
C5 C6 C4 119.24(7) . 2_556 ?
N1 C7 C8 109.38(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 111.34(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 110.91(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 108.90(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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.98(8) . . . . ?
C3 C1 C2 C3 2.45(13) 2_767 . . . ?
O1 C1 C2 Cl1 -0.32(12) . . . . ?
C3 C1 C2 Cl1 -179.90(6) 2_767 . . . ?
C1 C2 C3 O2 177.12(8) . . . . ?
Cl1 C2 C3 O2 -0.43(13) . . . . ?
C1 C2 C3 C1 -2.49(13) . . . 2_767 ?
Cl1 C2 C3 C1 179.95(6) . . . 2_767 ?
O3 C4 C5 C6 178.02(9) . . . . ?
C6 C4 C5 C6 -0.93(14) 2_556 . . . ?
O3 C4 C5 Cl2 -1.65(12) . . . . ?
C6 C4 C5 Cl2 179.40(6) 2_556 . . . ?
C4 C5 C6 O4 179.98(8) . . . . ?
Cl2 C5 C6 O4 -0.35(13) . . . . ?
C4 C5 C6 C4 0.94(14) . . . 2_556 ?
Cl2 C5 C6 C4 -179.39(6) . . . 2_556 ?
C10 N1 C7 C8 -53.54(10) . . . . ?
C9 O5 C8 C7 -61.29(10) . . . . ?
N1 C7 C8 O5 56.49(10) . . . . ?
C8 O5 C9 C10 62.16(10) . . . . ?
C7 N1 C10 C9 54.30(10) . . . . ?
O5 C9 C10 N1 -58.33(10) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.475
_refine_diff_density_min -0.237
_refine_diff_density_rms 0.055
# Attachment '- 160K.cif'
data_160K
_database_code_depnum_ccdc_archive 'CCDC 876324'
_chemical_name_common 'morpholinium hydrogen chloranilete'
_chemical_melting_point ?
_chemical_formula_moiety 'C4 H10 N O, C6 H2 Cl2 O4'
_chemical_formula_sum 'C10 H11 Cl2 N O5'
_chemical_formula_weight 296.10
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.62499(16)
_cell_length_b 9.12773(17)
_cell_length_c 9.20087(17)
_cell_angle_alpha 92.0011(7)
_cell_angle_beta 116.6392(7)
_cell_angle_gamma 113.8619(7)
_cell_volume 571.01(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 15910
_cell_measurement_theta_min 3.1
_cell_measurement_theta_max 30.2
_cell_measurement_temperature 160(1)
_exptl_crystal_description block
_exptl_crystal_colour brown
_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
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.722
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.581
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_absorpt_correction_T_min 0.834
_exptl_absorpt_correction_T_max 0.901
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 160(1)
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16945
_diffrn_reflns_av_R_equivalents 0.0141
_diffrn_reflns_av_sigmaI/netI 0.0080
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 3.09
_diffrn_reflns_theta_max 30.03
_reflns_number_total 3334
_reflns_number_gt 3180
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_cell_refinement PROCESS-AUTO
_computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.2004P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3334
_refine_ls_number_parameters 178
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0240
_refine_ls_R_factor_gt 0.0230
_refine_ls_wR_factor_ref 0.0632
_refine_ls_wR_factor_gt 0.0623
_refine_ls_goodness_of_fit_ref 1.056
_refine_ls_restrained_S_all 1.056
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.76459(3) 0.16961(3) 0.70582(3) 0.01787(6) Uani 1 1 d . . .
Cl2 Cl -0.00185(3) 0.11679(3) 0.18076(3) 0.02073(6) Uani 1 1 d . . .
O1 O 1.17765(10) 0.32532(8) 0.98069(8) 0.01700(13) Uani 1 1 d . . .
O2 O 0.61855(9) 0.40915(8) 0.76715(9) 0.01678(13) Uani 1 1 d D . .
H2 H 0.546(3) 0.319(2) 0.697(3) 0.025 Uiso 0.59(3) 1 d PD . .
O3 O -0.34155(10) -0.07827(9) 0.22476(9) 0.02047(14) Uani 1 1 d . . .
O4 O 0.34689(9) 0.18457(8) 0.50784(8) 0.01676(13) Uani 1 1 d D . .
H4 H 0.430(4) 0.237(4) 0.609(3) 0.025 Uiso 0.41(3) 1 d PD . .
O5 O 0.82620(10) 0.41658(9) 0.26511(9) 0.02117(14) Uani 1 1 d . . .
N1 N 0.48521(12) 0.32015(10) 0.29249(10) 0.01724(15) Uani 1 1 d . . .
C1 C 1.09076(12) 0.40193(10) 0.98607(10) 0.01266(15) Uani 1 1 d . . .
C2 C 0.88734(12) 0.34938(10) 0.86520(10) 0.01315(15) Uani 1 1 d . . .
C3 C 0.79725(12) 0.44014(10) 0.87184(10) 0.01298(15) Uani 1 1 d . . .
C4 C -0.18264(12) -0.04170(10) 0.34796(11) 0.01369(15) Uani 1 1 d . . .
C5 C 0.00287(12) 0.05470(11) 0.35682(11) 0.01411(15) Uani 1 1 d . . .
C6 C 0.17887(12) 0.09829(10) 0.49731(11) 0.01368(15) Uani 1 1 d . . .
C7 C 0.50705(14) 0.19888(12) 0.19854(12) 0.01989(17) Uani 1 1 d . . .
H7A H 0.3766 0.1171 0.1036 0.024 Uiso 1 1 calc R . .
H7B H 0.5638 0.1380 0.2748 0.024 Uiso 1 1 calc R . .
C8 C 0.63991(14) 0.29164(13) 0.13231(12) 0.02112(18) Uani 1 1 d . . .
H8A H 0.6592 0.2124 0.0749 0.025 Uiso 1 1 calc R . .
H8B H 0.5767 0.3440 0.0484 0.025 Uiso 1 1 calc R . .
C9 C 0.80235(14) 0.53597(12) 0.34546(13) 0.02012(18) Uani 1 1 d . . .
H9A H 0.7370 0.5870 0.2613 0.024 Uiso 1 1 calc R . .
H9B H 0.9331 0.6251 0.4331 0.024 Uiso 1 1 calc R . .
C10 C 0.68066(14) 0.45581(12) 0.42548(12) 0.01832(17) Uani 1 1 d . . .
H10A H 0.7486 0.4097 0.5141 0.022 Uiso 1 1 calc R . .
H10B H 0.6631 0.5397 0.4784 0.022 Uiso 1 1 calc R . .
H1A H 0.417(2) 0.2680(19) 0.343(2) 0.030(4) Uiso 1 1 d . . .
H1B H 0.419(2) 0.3646(18) 0.2183(19) 0.026(3) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01564(10) 0.01516(10) 0.01735(11) -0.00032(7) 0.00529(8) 0.00638(8)
Cl2 0.01644(10) 0.02648(12) 0.01525(10) 0.00979(8) 0.00756(8) 0.00684(9)
O1 0.0159(3) 0.0191(3) 0.0180(3) 0.0049(2) 0.0078(2) 0.0109(2)
O2 0.0103(3) 0.0175(3) 0.0168(3) 0.0016(2) 0.0030(2) 0.0062(2)
O3 0.0124(3) 0.0261(3) 0.0164(3) 0.0070(3) 0.0042(2) 0.0069(3)
O4 0.0104(3) 0.0199(3) 0.0142(3) 0.0029(2) 0.0056(2) 0.0030(2)
O5 0.0151(3) 0.0237(3) 0.0243(3) 0.0027(3) 0.0115(3) 0.0073(3)
N1 0.0146(3) 0.0224(4) 0.0193(4) 0.0096(3) 0.0104(3) 0.0101(3)
C1 0.0121(3) 0.0135(3) 0.0128(3) 0.0053(3) 0.0068(3) 0.0058(3)
C2 0.0115(3) 0.0128(3) 0.0123(3) 0.0019(3) 0.0049(3) 0.0046(3)
C3 0.0113(3) 0.0137(3) 0.0130(4) 0.0043(3) 0.0063(3) 0.0050(3)
C4 0.0126(4) 0.0135(3) 0.0133(4) 0.0030(3) 0.0057(3) 0.0058(3)
C5 0.0130(4) 0.0155(4) 0.0124(4) 0.0048(3) 0.0062(3) 0.0057(3)
C6 0.0131(4) 0.0127(3) 0.0137(4) 0.0025(3) 0.0062(3) 0.0055(3)
C7 0.0181(4) 0.0183(4) 0.0211(4) 0.0038(3) 0.0105(4) 0.0061(3)
C8 0.0197(4) 0.0238(4) 0.0184(4) 0.0027(3) 0.0112(4) 0.0075(4)
C9 0.0182(4) 0.0184(4) 0.0229(4) 0.0043(3) 0.0116(4) 0.0067(3)
C10 0.0184(4) 0.0214(4) 0.0170(4) 0.0052(3) 0.0097(3) 0.0102(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7315(9) . ?
Cl2 C5 1.7235(9) . ?
O1 C1 1.2280(10) . ?
O2 C3 1.2962(10) . ?
O2 H2 0.821(17) . ?
O3 C4 1.2186(11) . ?
O4 C6 1.2943(10) . ?
O4 H4 0.837(19) . ?
O5 C8 1.4264(12) . ?
O5 C9 1.4276(12) . ?
N1 C10 1.4927(12) . ?
N1 C7 1.5020(12) . ?
N1 H1A 0.910(16) . ?
N1 H1B 0.904(15) . ?
C1 C2 1.4413(11) . ?
C1 C3 1.5263(12) 2_767 ?
C2 C3 1.3615(12) . ?
C3 C1 1.5263(12) 2_767 ?
C4 C5 1.4422(12) . ?
C4 C6 1.5226(12) 2_556 ?
C5 C6 1.3599(11) . ?
C6 C4 1.5226(12) 2_556 ?
C7 C8 1.5095(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5127(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 116.8(18) . . ?
C6 O4 H4 108(2) . . ?
C8 O5 C9 110.30(7) . . ?
C10 N1 C7 111.33(7) . . ?
C10 N1 H1A 108.2(10) . . ?
C7 N1 H1A 110.6(10) . . ?
C10 N1 H1B 109.4(9) . . ?
C7 N1 H1B 108.7(9) . . ?
H1A N1 H1B 108.6(13) . . ?
O1 C1 C2 123.18(8) . . ?
O1 C1 C3 118.56(7) . 2_767 ?
C2 C1 C3 118.26(7) . 2_767 ?
C3 C2 C1 121.63(8) . . ?
C3 C2 Cl1 121.26(6) . . ?
C1 C2 Cl1 117.07(6) . . ?
O2 C3 C2 127.20(8) . . ?
O2 C3 C1 112.73(7) . 2_767 ?
C2 C3 C1 120.06(7) . 2_767 ?
O3 C4 C5 123.74(8) . . ?
O3 C4 C6 118.33(8) . 2_556 ?
C5 C4 C6 117.93(7) . 2_556 ?
C6 C5 C4 122.81(8) . . ?
C6 C5 Cl2 119.35(7) . . ?
C4 C5 Cl2 117.84(6) . . ?
O4 C6 C5 123.78(8) . . ?
O4 C6 C4 116.95(7) . 2_556 ?
C5 C6 C4 119.25(7) . 2_556 ?
N1 C7 C8 109.36(8) . . ?
N1 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O5 C8 C7 111.31(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 110.93(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 108.89(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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.91(8) . . . . ?
C3 C1 C2 C3 2.52(13) 2_767 . . . ?
O1 C1 C2 Cl1 -0.36(12) . . . . ?
C3 C1 C2 Cl1 -179.92(6) 2_767 . . . ?
C1 C2 C3 O2 177.13(8) . . . . ?
Cl1 C2 C3 O2 -0.31(13) . . . . ?
C1 C2 C3 C1 -2.57(13) . . . 2_767 ?
Cl1 C2 C3 C1 179.98(6) . . . 2_767 ?
O3 C4 C5 C6 178.03(9) . . . . ?
C6 C4 C5 C6 -0.92(14) 2_556 . . . ?
O3 C4 C5 Cl2 -1.71(12) . . . . ?
C6 C4 C5 Cl2 179.35(6) 2_556 . . . ?
C4 C5 C6 O4 179.95(8) . . . . ?
Cl2 C5 C6 O4 -0.32(13) . . . . ?
C4 C5 C6 C4 0.93(14) . . . 2_556 ?
Cl2 C5 C6 C4 -179.34(6) . . . 2_556 ?
C10 N1 C7 C8 -53.53(10) . . . . ?
C9 O5 C8 C7 -61.29(10) . . . . ?
N1 C7 C8 O5 56.47(11) . . . . ?
C8 O5 C9 C10 62.18(10) . . . . ?
C7 N1 C10 C9 54.30(10) . . . . ?
O5 C9 C10 N1 -58.32(10) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.459
_refine_diff_density_min -0.203
_refine_diff_density_rms 0.055
# Attachment '- 180K.cif'
data_180K
_database_code_depnum_ccdc_archive 'CCDC 876325'
#TrackingRef '- 180K.cif'
_audit_update_record
;
2012-04-16 # Formatted by publCIF
;
_chemical_name_common 'morpholinium hydrogen chloranilete'
_chemical_melting_point ?
_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
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.62739(16)
_cell_length_b 9.13846(17)
_cell_length_c 9.20609(17)
_cell_angle_alpha 92.0264(7)
_cell_angle_beta 116.6211(7)
_cell_angle_gamma 113.8289(7)
_cell_volume 572.40(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 180(1)
_cell_measurement_reflns_used 15822
_cell_measurement_theta_min 3.1
_cell_measurement_theta_max 30.1
_exptl_crystal_description block
_exptl_crystal_colour brown
_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
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.718
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.580
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_absorpt_correction_T_min 0.824
_exptl_absorpt_correction_T_max 0.901
_diffrn_ambient_temperature 180(2)
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16984
_diffrn_reflns_av_R_equivalents 0.0141
_diffrn_reflns_av_sigmaI/netI 0.0081
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 3.09
_diffrn_reflns_theta_max 30.03
_reflns_number_total 3342
_reflns_number_gt 3167
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_cell_refinement PROCESS-AUTO
_computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.1931P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3342
_refine_ls_number_parameters 178
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0246
_refine_ls_R_factor_gt 0.0234
_refine_ls_wR_factor_ref 0.0642
_refine_ls_wR_factor_gt 0.0631
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.046
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
_atom_site_disorder_assembly
_atom_site_disorder_group
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01715(10) 0.01668(10) 0.01907(11) -0.00039(8) 0.00568(8) 0.00701(8)
Cl2 0.01796(11) 0.02924(12) 0.01672(11) 0.01083(8) 0.00822(8) 0.00743(9)
O1 0.0172(3) 0.0210(3) 0.0197(3) 0.0053(2) 0.0083(3) 0.0120(3)
O2 0.0111(3) 0.0193(3) 0.0186(3) 0.0019(2) 0.0033(2) 0.0068(2)
O3 0.0133(3) 0.0288(4) 0.0179(3) 0.0078(3) 0.0044(3) 0.0074(3)
O4 0.0113(3) 0.0217(3) 0.0155(3) 0.0032(2) 0.0060(2) 0.0033(2)
O5 0.0166(3) 0.0264(3) 0.0267(4) 0.0031(3) 0.0127(3) 0.0081(3)
N1 0.0160(3) 0.0245(4) 0.0213(4) 0.0107(3) 0.0115(3) 0.0111(3)
C1 0.0130(3) 0.0148(3) 0.0139(4) 0.0056(3) 0.0073(3) 0.0064(3)
C2 0.0123(3) 0.0140(3) 0.0135(4) 0.0022(3) 0.0054(3) 0.0051(3)
C3 0.0119(3) 0.0151(4) 0.0141(4) 0.0047(3) 0.0066(3) 0.0053(3)
C4 0.0136(4) 0.0149(4) 0.0145(4) 0.0034(3) 0.0061(3) 0.0063(3)
C5 0.0139(4) 0.0170(4) 0.0134(4) 0.0052(3) 0.0066(3) 0.0061(3)
C6 0.0141(4) 0.0142(4) 0.0147(4) 0.0026(3) 0.0066(3) 0.0060(3)
C7 0.0197(4) 0.0200(4) 0.0231(4) 0.0040(3) 0.0114(4) 0.0066(3)
C8 0.0218(4) 0.0263(5) 0.0202(4) 0.0029(4) 0.0125(4) 0.0084(4)
C9 0.0199(4) 0.0204(4) 0.0252(5) 0.0047(3) 0.0129(4) 0.0073(3)
C10 0.0205(4) 0.0237(4) 0.0186(4) 0.0059(3) 0.0108(3) 0.0115(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 30.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.440
_refine_diff_density_min -0.202
_refine_diff_density_rms 0.055
# Attachment '- 200K.cif'
data_200K
_database_code_depnum_ccdc_archive 'CCDC 876326'
#TrackingRef '- 200K.cif'
_audit_update_record
;
2012-04-16 # Formatted by publCIF
;
_chemical_name_common 'morpholinium hydrogen chloranilete'
_chemical_melting_point ?
_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
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.62930(16)
_cell_length_b 9.15077(17)
_cell_length_c 9.21274(17)
_cell_angle_alpha 92.0613(7)
_cell_angle_beta 116.6008(7)
_cell_angle_gamma 113.7992(7)
_cell_volume 573.91(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 200(1)
_cell_measurement_reflns_used 15792
_cell_measurement_theta_min 3.1
_cell_measurement_theta_max 30.1
_exptl_crystal_description block
_exptl_crystal_colour brown
_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
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.713
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.578
_exptl_absorpt_correction_T_min 0.824
_exptl_absorpt_correction_T_max 0.901
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_diffrn_ambient_temperature 200(1)
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17031
_diffrn_reflns_av_R_equivalents 0.0146
_diffrn_reflns_av_sigmaI/netI 0.0083
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 3.08
_diffrn_reflns_theta_max 30.02
_reflns_number_total 3346
_reflns_number_gt 3185
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_cell_refinement PROCESS-AUTO
_computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.1816P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3346
_refine_ls_number_parameters 178
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0254
_refine_ls_R_factor_gt 0.0241
_refine_ls_wR_factor_ref 0.0659
_refine_ls_wR_factor_gt 0.0651
_refine_ls_goodness_of_fit_ref 1.056
_refine_ls_restrained_S_all 1.056
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.76513(3) 0.17033(3) 0.70648(3) 0.02201(6) Uani 1 1 d . . .
Cl2 Cl -0.00246(3) 0.11669(3) 0.18128(3) 0.02542(7) Uani 1 1 d . . .
O1 O 1.17755(10) 0.32538(9) 0.98132(9) 0.02070(14) Uani 1 1 d . . .
O2 O 0.61940(10) 0.40944(9) 0.76722(9) 0.02034(13) Uani 1 1 d D . .
H2 H 0.547(3) 0.320(2) 0.698(3) 0.031 Uiso 0.59(3) 1 d PD . .
O3 O -0.34123(10) -0.07847(10) 0.22563(9) 0.02504(15) Uani 1 1 d . . .
O4 O 0.34606(10) 0.18478(9) 0.50760(9) 0.02032(13) Uani 1 1 d D . .
H4 H 0.430(4) 0.234(4) 0.608(3) 0.030 Uiso 0.41(3) 1 d PD . .
O5 O 0.82500(11) 0.41597(10) 0.26467(10) 0.02596(15) Uani 1 1 d . . .
N1 N 0.48482(12) 0.32041(11) 0.29217(11) 0.02102(16) Uani 1 1 d . . .
C1 C 1.09053(12) 0.40180(10) 0.98630(11) 0.01518(15) Uani 1 1 d . . .
C2 C 0.88784(12) 0.34981(10) 0.86557(11) 0.01587(15) Uani 1 1 d . . .
C3 C 0.79756(12) 0.44040(11) 0.87191(11) 0.01559(15) Uani 1 1 d . . .
C4 C -0.18239(13) -0.04175(11) 0.34843(11) 0.01665(15) Uani 1 1 d . . .
C5 C 0.00261(13) 0.05466(11) 0.35700(11) 0.01710(16) Uani 1 1 d . . .
C6 C 0.17829(12) 0.09833(10) 0.49715(11) 0.01649(16) Uani 1 1 d . . .
C7 C 0.50641(15) 0.19935(13) 0.19819(13) 0.02420(19) Uani 1 1 d . . .
H7A H 0.3761 0.1180 0.1033 0.029 Uiso 1 1 calc R . .
H7B H 0.5629 0.1384 0.2741 0.029 Uiso 1 1 calc R . .
C8 C 0.63917(15) 0.29169(13) 0.13223(13) 0.0258(2) Uani 1 1 d . . .
H8A H 0.6585 0.2126 0.0748 0.031 Uiso 1 1 calc R . .
H8B H 0.5761 0.3440 0.0486 0.031 Uiso 1 1 calc R . .
C9 C 0.80135(15) 0.53503(13) 0.34507(13) 0.02450(19) Uani 1 1 d . . .
H9A H 0.7363 0.5861 0.2612 0.029 Uiso 1 1 calc R . .
H9B H 0.9319 0.6238 0.4326 0.029 Uiso 1 1 calc R . .
C10 C 0.67981(15) 0.45530(13) 0.42488(12) 0.02237(18) Uani 1 1 d . . .
H10A H 0.7475 0.4092 0.5133 0.027 Uiso 1 1 calc R . .
H10B H 0.6623 0.5390 0.4778 0.027 Uiso 1 1 calc R . .
H1A H 0.415(2) 0.2678(19) 0.341(2) 0.034(4) Uiso 1 1 d . . .
H1B H 0.418(2) 0.3653(19) 0.2184(19) 0.031(4) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01907(11) 0.01870(11) 0.02133(11) -0.00042(8) 0.00630(9) 0.00779(8)
Cl2 0.01993(11) 0.03258(13) 0.01857(11) 0.01202(9) 0.00907(9) 0.00818(9)
O1 0.0188(3) 0.0234(3) 0.0219(3) 0.0057(3) 0.0090(3) 0.0131(3)
O2 0.0124(3) 0.0215(3) 0.0205(3) 0.0022(2) 0.0037(2) 0.0077(2)
O3 0.0147(3) 0.0323(4) 0.0197(3) 0.0087(3) 0.0048(3) 0.0080(3)
O4 0.0125(3) 0.0241(3) 0.0171(3) 0.0037(2) 0.0066(2) 0.0036(2)
O5 0.0186(3) 0.0294(4) 0.0299(4) 0.0038(3) 0.0144(3) 0.0092(3)
N1 0.0176(3) 0.0276(4) 0.0238(4) 0.0123(3) 0.0130(3) 0.0125(3)
C1 0.0144(3) 0.0167(4) 0.0153(4) 0.0062(3) 0.0081(3) 0.0072(3)
C2 0.0136(3) 0.0158(4) 0.0152(4) 0.0028(3) 0.0061(3) 0.0058(3)
C3 0.0131(4) 0.0170(4) 0.0154(4) 0.0053(3) 0.0072(3) 0.0060(3)
C4 0.0149(4) 0.0165(4) 0.0161(4) 0.0036(3) 0.0065(3) 0.0067(3)
C5 0.0154(4) 0.0188(4) 0.0150(4) 0.0056(3) 0.0072(3) 0.0067(3)
C6 0.0153(4) 0.0157(4) 0.0159(4) 0.0028(3) 0.0069(3) 0.0063(3)
C7 0.0215(4) 0.0223(4) 0.0258(5) 0.0046(4) 0.0124(4) 0.0073(4)
C8 0.0243(5) 0.0293(5) 0.0226(4) 0.0034(4) 0.0139(4) 0.0094(4)
C9 0.0219(4) 0.0226(4) 0.0280(5) 0.0052(4) 0.0141(4) 0.0079(4)
C10 0.0229(4) 0.0266(4) 0.0208(4) 0.0067(3) 0.0121(4) 0.0131(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7321(9) . ?
Cl2 C5 1.7226(9) . ?
O1 C1 1.2278(10) . ?
O2 C3 1.2942(10) . ?
O2 H2 0.812(17) . ?
O3 C4 1.2181(11) . ?
O4 C6 1.2947(10) . ?
O4 H4 0.832(19) . ?
O5 C8 1.4247(13) . ?
O5 C9 1.4262(12) . ?
N1 C10 1.4908(13) . ?
N1 C7 1.5012(13) . ?
N1 H1A 0.904(16) . ?
N1 H1B 0.909(16) . ?
C1 C2 1.4390(11) . ?
C1 C3 1.5275(12) 2_767 ?
C2 C3 1.3624(12) . ?
C3 C1 1.5275(12) 2_767 ?
C4 C5 1.4418(12) . ?
C4 C6 1.5217(12) 2_556 ?
C5 C6 1.3587(12) . ?
C6 C4 1.5217(12) 2_556 ?
C7 C8 1.5083(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5115(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 117.5(19) . . ?
C6 O4 H4 108(3) . . ?
C8 O5 C9 110.33(8) . . ?
C10 N1 C7 111.37(7) . . ?
C10 N1 H1A 109.0(10) . . ?
C7 N1 H1A 110.1(10) . . ?
C10 N1 H1B 109.3(10) . . ?
C7 N1 H1B 109.1(9) . . ?
H1A N1 H1B 107.9(13) . . ?
O1 C1 C2 123.29(8) . . ?
O1 C1 C3 118.46(7) . 2_767 ?
C2 C1 C3 118.25(7) . 2_767 ?
C3 C2 C1 121.72(8) . . ?
C3 C2 Cl1 121.15(7) . . ?
C1 C2 Cl1 117.09(6) . . ?
O2 C3 C2 127.15(8) . . ?
O2 C3 C1 112.85(7) . 2_767 ?
C2 C3 C1 119.99(7) . 2_767 ?
O3 C4 C5 123.74(8) . . ?
O3 C4 C6 118.29(8) . 2_556 ?
C5 C4 C6 117.97(7) . 2_556 ?
C6 C5 C4 122.72(8) . . ?
C6 C5 Cl2 119.40(7) . . ?
C4 C5 Cl2 117.88(6) . . ?
O4 C6 C5 123.75(8) . . ?
O4 C6 C4 116.94(7) . 2_556 ?
C5 C6 C4 119.31(7) . 2_556 ?
N1 C7 C8 109.32(8) . . ?
N1 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O5 C8 C7 111.35(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 108.88(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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.95(8) . . . . ?
C3 C1 C2 C3 2.34(13) 2_767 . . . ?
O1 C1 C2 Cl1 -0.25(12) . . . . ?
C3 C1 C2 Cl1 -179.96(6) 2_767 . . . ?
C1 C2 C3 O2 177.19(8) . . . . ?
Cl1 C2 C3 O2 -0.41(13) . . . . ?
C1 C2 C3 C1 -2.38(14) . . . 2_767 ?
Cl1 C2 C3 C1 -179.99(6) . . . 2_767 ?
O3 C4 C5 C6 177.99(9) . . . . ?
C6 C4 C5 C6 -1.01(14) 2_556 . . . ?
O3 C4 C5 Cl2 -1.68(13) . . . . ?
C6 C4 C5 Cl2 179.33(6) 2_556 . . . ?
C4 C5 C6 O4 180.00(8) . . . . ?
Cl2 C5 C6 O4 -0.34(13) . . . . ?
C4 C5 C6 C4 1.02(14) . . . 2_556 ?
Cl2 C5 C6 C4 -179.32(6) . . . 2_556 ?
C10 N1 C7 C8 -53.51(11) . . . . ?
C9 O5 C8 C7 -61.25(11) . . . . ?
N1 C7 C8 O5 56.41(11) . . . . ?
C8 O5 C9 C10 62.14(11) . . . . ?
C7 N1 C10 C9 54.30(10) . . . . ?
O5 C9 C10 N1 -58.29(11) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.448
_refine_diff_density_min -0.252
_refine_diff_density_rms 0.058