# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_roth1
_database_code_depnum_ccdc_archive 'CCDC 1019891'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_audit_creation_date             2014-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'4-methylmorpholine 4-oxide compound with 2,2,2-trichloroethane-1,1-diol (1:1)'
_chemical_formula_moiety         'C2 H3 Cl3 O2, C5 H11 N O2'
_chemical_formula_sum            'C7 H14 Cl3 N O4'
_chemical_formula_weight         282.54
_chemical_melting_point          348-350
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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6911(2)
_cell_length_b                   12.4710(2)
_cell_length_c                   14.9357(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.68
_cell_angle_gamma                90
_cell_volume                     2362.86(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1
_cell_measurement_temperature    100
_cell_measurement_theta_max      1
_cell_measurement_theta_min      1
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            51329
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.563
_diffrn_reflns_theta_min         2.076
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'BRUKER AXS SMART APEX'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         1
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7682
_reflns_number_total             8934
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         8934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.8250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0644
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Me refined with riding coordinates:
 C3(H3A,H3B,H3C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O5(H5), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.83838(2) 0.23558(2) 0.42554(2) 0.02391(6) Uani 1 1 d . . . . .
Cl2 Cl 0.76362(2) 0.42270(2) 0.51880(2) 0.01923(5) Uani 1 1 d . . . . .
Cl3 Cl 0.64411(2) 0.22530(2) 0.52002(2) 0.01831(5) Uani 1 1 d . . . . .
O1 O 0.78526(6) 0.29023(6) 0.68213(5) 0.01760(13) Uani 1 1 d . . . . .
H1 H 0.8278 0.3274 0.7131 0.026 Uiso 1 1 calc R U . . .
O2 O 0.84348(6) 0.13828(6) 0.61070(5) 0.01947(14) Uani 1 1 d . . . . .
H2 H 0.8641 0.1184 0.6620 0.029 Uiso 1 1 calc R U . . .
C1 C 0.83613(7) 0.24913(7) 0.60866(6) 0.01476(16) Uani 1 1 d . . . . .
H1A H 0.9085 0.2805 0.6065 0.018 Uiso 1 1 calc R U . . .
C2 C 0.77249(7) 0.28056(8) 0.52219(6) 0.01485(16) Uani 1 1 d . . . . .
Cl4 Cl 0.81362(2) 0.90876(2) 0.52167(2) 0.02133(5) Uani 1 1 d . . . . .
Cl5 Cl 0.71633(2) 0.75324(2) 0.40023(2) 0.01608(5) Uani 1 1 d . . . . .
Cl6 Cl 0.88550(2) 0.68949(2) 0.52219(2) 0.01965(5) Uani 1 1 d . . . . .
O5 O 0.66640(6) 0.63872(6) 0.57283(5) 0.02075(14) Uani 1 1 d . . . . .
H5 H 0.6389 0.6172 0.6201 0.031 Uiso 1 1 calc R U . . .
O6 O 0.60381(6) 0.81293(6) 0.56649(5) 0.02139(15) Uani 1 1 d . . . . .
H6 H 0.5875 0.8418 0.6149 0.032 Uiso 1 1 calc R U . . .
C8 C 0.69115(7) 0.74695(7) 0.58117(6) 0.01546(16) Uani 1 1 d . . . . .
H8 H 0.7230 0.7611 0.6421 0.019 Uiso 1 1 calc R U . . .
C9 C 0.77245(7) 0.77323(7) 0.50880(6) 0.01399(16) Uani 1 1 d . . . . .
O3 O 0.56516(6) -0.10900(5) 0.72577(5) 0.01741(13) Uani 1 1 d . . . . .
O4 O 0.31980(6) 0.00655(7) 0.73295(5) 0.02434(16) Uani 1 1 d . . . . .
N2 N 0.54657(6) 0.00158(6) 0.73004(5) 0.01484(14) Uani 1 1 d . . . . .
C3 C 0.64886(9) 0.06051(10) 0.73140(9) 0.0284(2) Uani 1 1 d . . . . .
H3A H 0.6355 0.1378 0.7344 0.043 Uiso 1 1 calc R U . . .
H3B H 0.6916 0.0384 0.7839 0.043 Uiso 1 1 calc R U . . .
H3C H 0.6867 0.0441 0.6768 0.043 Uiso 1 1 calc R U . . .
C4 C 0.47881(8) 0.03555(8) 0.65045(6) 0.01941(18) Uani 1 1 d . . . . .
H4A H 0.5142 0.0165 0.5944 0.023 Uiso 1 1 calc R U . . .
H4B H 0.4688 0.1143 0.6515 0.023 Uiso 1 1 calc R U . . .
C5 C 0.37309(8) -0.01966(9) 0.65301(7) 0.0224(2) Uani 1 1 d . . . . .
H5A H 0.3292 0.0024 0.6003 0.027 Uiso 1 1 calc R U . . .
H5B H 0.3833 -0.0983 0.6499 0.027 Uiso 1 1 calc R U . . .
C6 C 0.38069(8) -0.02949(9) 0.80879(7) 0.02216(19) Uani 1 1 d . . . . .
H6A H 0.3906 -0.1081 0.8050 0.027 Uiso 1 1 calc R U . . .
H6B H 0.3424 -0.0138 0.8641 0.027 Uiso 1 1 calc R U . . .
C7 C 0.48718(8) 0.02509(8) 0.81330(6) 0.01860(18) Uani 1 1 d . . . . .
H7A H 0.4775 0.1035 0.8194 0.022 Uiso 1 1 calc R U . . .
H7B H 0.5281 -0.0008 0.8664 0.022 Uiso 1 1 calc R U . . .
O7 O 0.58662(5) 0.58248(6) 0.72871(5) 0.01672(13) Uani 1 1 d . . . . .
O8 O 0.48421(6) 0.32801(6) 0.69853(5) 0.02110(14) Uani 1 1 d . . . . .
N1 N 0.47998(6) 0.55486(6) 0.73359(5) 0.01496(14) Uani 1 1 d . . . . .
C10 C 0.41750(9) 0.65238(9) 0.75450(9) 0.0271(2) Uani 1 1 d . . . . .
H10A H 0.3428 0.6332 0.7579 0.041 Uiso 1 1 calc R U . . .
H10B H 0.4424 0.6821 0.8121 0.041 Uiso 1 1 calc R U . . .
H10C H 0.4262 0.7059 0.7073 0.041 Uiso 1 1 calc R U . . .
C11 C 0.44150(8) 0.50690(9) 0.64606(6) 0.01909(18) Uani 1 1 d . . . . .
H11A H 0.4533 0.5583 0.5968 0.023 Uiso 1 1 calc R U . . .
H11B H 0.3649 0.4927 0.6483 0.023 Uiso 1 1 calc R U . . .
C12 C 0.49911(8) 0.40372(9) 0.62798(7) 0.02080(19) Uani 1 1 d . . . . .
H12A H 0.4727 0.3729 0.5705 0.025 Uiso 1 1 calc R U . . .
H12B H 0.5753 0.4187 0.6227 0.025 Uiso 1 1 calc R U . . .
C13 C 0.52627(8) 0.37103(8) 0.78046(7) 0.01901(18) Uani 1 1 d . . . . .
H13A H 0.6018 0.3880 0.7738 0.023 Uiso 1 1 calc R U . . .
H13B H 0.5205 0.3170 0.8286 0.023 Uiso 1 1 calc R U . . .
C14 C 0.46744(8) 0.47161(8) 0.80584(6) 0.01679(17) Uani 1 1 d . . . . .
H14A H 0.3918 0.4550 0.8126 0.020 Uiso 1 1 calc R U . . .
H14B H 0.4959 0.4995 0.8637 0.020 Uiso 1 1 calc R U . . .


_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 1.7801(9) . ?
Cl2 C2 1.7768(10) . ?
Cl3 C2 1.7684(9) . ?
O1 H1 0.8400 . ?
O1 C1 1.3875(11) . ?
O2 H2 0.8400 . ?
O2 C1 1.3858(11) . ?
C1 H1A 1.0000 . ?
C1 C2 1.5533(13) . ?
Cl4 C9 1.7779(9) . ?
Cl5 C9 1.7695(9) . ?
Cl6 C9 1.7811(9) . ?
O5 H5 0.8400 . ?
O5 C8 1.3906(12) . ?
O6 H6 0.8400 . ?
O6 C8 1.3926(12) . ?
C8 H8 1.0000 . ?
C8 C9 1.5511(13) . ?
O3 N2 1.4008(10) . ?
O4 C5 1.4273(13) . ?
O4 C6 1.4250(13) . ?
N2 C3 1.4913(13) . ?
N2 C4 1.5072(12) . ?
N2 C7 1.5019(12) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5096(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5129(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O7 N1 1.4004(10) . ?
O8 C12 1.4316(13) . ?
O8 C13 1.4254(12) . ?
N1 C10 1.4900(13) . ?
N1 C11 1.5059(12) . ?
N1 C14 1.5093(12) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5082(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5136(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 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
C1 O1 H1 109.5 . . ?
C1 O2 H2 109.5 . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 C2 108.76(7) . . ?
O2 C1 O1 112.57(8) . . ?
O2 C1 H1A 109.3 . . ?
O2 C1 C2 107.64(7) . . ?
C2 C1 H1A 109.3 . . ?
Cl2 C2 Cl1 108.79(5) . . ?
Cl3 C2 Cl1 108.47(5) . . ?
Cl3 C2 Cl2 109.31(5) . . ?
C1 C2 Cl1 110.46(6) . . ?
C1 C2 Cl2 107.84(6) . . ?
C1 C2 Cl3 111.91(6) . . ?
C8 O5 H5 109.5 . . ?
C8 O6 H6 109.5 . . ?
O5 C8 O6 112.50(8) . . ?
O5 C8 H8 109.7 . . ?
O5 C8 C9 107.21(7) . . ?
O6 C8 H8 109.7 . . ?
O6 C8 C9 107.94(7) . . ?
C9 C8 H8 109.7 . . ?
Cl4 C9 Cl6 108.18(5) . . ?
Cl5 C9 Cl4 110.01(5) . . ?
Cl5 C9 Cl6 108.75(5) . . ?
C8 C9 Cl4 108.96(6) . . ?
C8 C9 Cl5 110.54(6) . . ?
C8 C9 Cl6 110.37(6) . . ?
C6 O4 C5 109.49(7) . . ?
O3 N2 C3 109.76(8) . . ?
O3 N2 C4 109.50(7) . . ?
O3 N2 C7 108.61(7) . . ?
C3 N2 C4 110.40(8) . . ?
C3 N2 C7 110.51(8) . . ?
C7 N2 C4 108.03(7) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
N2 C4 C5 109.81(8) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
O4 C5 C4 111.10(8) . . ?
O4 C5 H5A 109.4 . . ?
O4 C5 H5B 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
O4 C6 C7 110.87(8) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
N2 C7 C6 110.16(8) . . ?
N2 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C13 O8 C12 109.23(7) . . ?
O7 N1 C10 109.34(7) . . ?
O7 N1 C11 109.99(7) . . ?
O7 N1 C14 109.19(7) . . ?
C10 N1 C11 110.19(8) . . ?
C10 N1 C14 110.10(8) . . ?
C11 N1 C14 108.00(7) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
N1 C11 C12 110.35(8) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
O8 C12 C11 110.84(8) . . ?
O8 C12 H12A 109.5 . . ?
O8 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O8 C13 H13A 109.5 . . ?
O8 C13 H13B 109.5 . . ?
O8 C13 C14 110.60(8) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
N1 C14 C13 109.13(7) . . ?
N1 C14 H14A 109.9 . . ?
N1 C14 H14B 109.9 . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 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 Cl1 176.96(6) . . . . ?
O1 C1 C2 Cl2 58.19(8) . . . . ?
O1 C1 C2 Cl3 -62.07(9) . . . . ?
O2 C1 C2 Cl1 -60.82(9) . . . . ?
O2 C1 C2 Cl2 -179.59(6) . . . . ?
O2 C1 C2 Cl3 60.15(9) . . . . ?
O5 C8 C9 Cl4 -176.02(6) . . . . ?
O5 C8 C9 Cl5 62.98(8) . . . . ?
O5 C8 C9 Cl6 -57.37(9) . . . . ?
O6 C8 C9 Cl4 62.56(8) . . . . ?
O6 C8 C9 Cl5 -58.44(9) . . . . ?
O6 C8 C9 Cl6 -178.79(6) . . . . ?
O3 N2 C4 C5 62.47(10) . . . . ?
O3 N2 C7 C6 -63.02(10) . . . . ?
O4 C6 C7 N2 -59.45(11) . . . . ?
N2 C4 C5 O4 59.61(11) . . . . ?
C3 N2 C4 C5 -176.58(9) . . . . ?
C3 N2 C7 C6 176.52(8) . . . . ?
C4 N2 C7 C6 55.66(10) . . . . ?
C5 O4 C6 C7 61.29(11) . . . . ?
C6 O4 C5 C4 -61.64(11) . . . . ?
C7 N2 C4 C5 -55.65(10) . . . . ?
O7 N1 C11 C12 63.54(10) . . . . ?
O7 N1 C14 C13 -63.25(9) . . . . ?
O8 C13 C14 N1 -61.24(10) . . . . ?
N1 C11 C12 O8 58.78(10) . . . . ?
C10 N1 C11 C12 -175.84(8) . . . . ?
C10 N1 C14 C13 176.69(8) . . . . ?
C11 N1 C14 C13 56.33(10) . . . . ?
C12 O8 C13 C14 63.00(10) . . . . ?
C13 O8 C12 C11 -61.52(10) . . . . ?
C14 N1 C11 C12 -55.54(10) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_roth2
_audit_block_doi                 10.5517/cc1378xj
_database_code_depnum_ccdc_archive 'CCDC 1019897'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_audit_creation_date             2014-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'pyridine-N-oxide compound with 2,2,2-trichloroethane-1,1-diol (1:1)'
_chemical_formula_moiety         'C2 H3 Cl3 O2, C5 H5 N O'
_chemical_formula_sum            'C7 H8 Cl3 N O3'
_chemical_formula_weight         260.49
_chemical_melting_point          none
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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.15940(10)
_cell_length_b                   12.8396(2)
_cell_length_c                   13.3985(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.56
_cell_angle_gamma                90
_cell_volume                     1038.13(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100
_cell_measurement_theta_max      1.8
_cell_measurement_theta_min      33.5
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.7024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   0.7466
_exptl_transmission_factor_min   0.7024
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23617
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.548
_diffrn_reflns_theta_min         2.219
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'BRUKER AXS SMART APEX'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3623
_reflns_number_total             3873
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         3873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+0.2949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0588
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.13201(3) 0.13963(2) 0.45920(2) 0.02167(5) Uani 1 1 d . . . . .
Cl2 Cl 0.41290(3) 0.18685(2) 0.31743(2) 0.02093(5) Uani 1 1 d . . . . .
Cl3 Cl 0.61057(3) 0.12699(2) 0.52394(2) 0.02052(5) Uani 1 1 d . . . . .
O1 O 0.58096(11) 0.36084(5) 0.46205(5) 0.01796(11) Uani 1 1 d . . . . .
H1 H 0.684(3) 0.3483(12) 0.5080(12) 0.035(4) Uiso 1 1 d . . . . .
O2 O 0.38086(10) 0.31642(5) 0.58296(4) 0.01821(11) Uani 1 1 d . . . . .
H2 H 0.256(3) 0.3282(12) 0.5863(12) 0.037(4) Uiso 1 1 d . . . . .
C1 C 0.39326(12) 0.31190(6) 0.48052(6) 0.01411(13) Uani 1 1 d . . . . .
H1A H 0.264(2) 0.3433(9) 0.4366(9) 0.015(3) Uiso 1 1 d . . . . .
C2 C 0.38939(12) 0.19531(6) 0.44721(6) 0.01442(13) Uani 1 1 d . . . . .
O3 O 0.97032(10) 0.36324(5) 0.59690(5) 0.01823(11) Uani 1 1 d . . . . .
N1 N 0.96811(11) 0.44740(5) 0.65544(5) 0.01413(11) Uani 1 1 d . . . . .
C3 C 0.80695(14) 0.45640(7) 0.71016(6) 0.01826(14) Uani 1 1 d . . . . .
H3 H 0.6990 0.4051 0.7059 0.022 Uiso 1 1 calc R U . . .
C4 C 0.80251(14) 0.54187(7) 0.77255(6) 0.02062(15) Uani 1 1 d . . . . .
H4 H 0.6918 0.5479 0.8103 0.025 Uiso 1 1 calc R U . . .
C5 C 0.96336(15) 0.61868(7) 0.77884(6) 0.02015(15) Uani 1 1 d . . . . .
H5 H 0.9626 0.6762 0.8210 0.024 Uiso 1 1 calc R U . . .
C6 C 1.12562(14) 0.60774(7) 0.72078(7) 0.01973(15) Uani 1 1 d . . . . .
H6 H 1.2343 0.6585 0.7235 0.024 Uiso 1 1 calc R U . . .
C7 C 1.12565(13) 0.52155(6) 0.65909(6) 0.01676(13) Uani 1 1 d . . . . .
H7 H 1.2339 0.5145 0.6201 0.020 Uiso 1 1 calc R U . . .


_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 1.7754(8) . ?
Cl2 C2 1.7770(8) . ?
Cl3 C2 1.7667(8) . ?
O1 C1 1.3810(10) . ?
O2 C1 1.3912(9) . ?
C1 C2 1.5609(11) . ?
O3 N1 1.3369(9) . ?
N1 C3 1.3521(10) . ?
N1 C7 1.3532(10) . ?
C3 C4 1.3832(12) . ?
C4 C5 1.3884(13) . ?
C5 C6 1.3911(13) . ?
C6 C7 1.3813(12) . ?

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
O1 C1 O2 111.79(6) . . ?
O1 C1 C2 110.52(6) . . ?
O2 C1 C2 108.74(6) . . ?
Cl1 C2 Cl2 108.26(4) . . ?
Cl3 C2 Cl1 110.23(4) . . ?
Cl3 C2 Cl2 109.55(4) . . ?
C1 C2 Cl1 108.85(5) . . ?
C1 C2 Cl2 109.80(5) . . ?
C1 C2 Cl3 110.12(5) . . ?
O3 N1 C3 118.82(7) . . ?
O3 N1 C7 119.89(6) . . ?
C3 N1 C7 121.29(7) . . ?
N1 C3 C4 120.07(8) . . ?
C3 C4 C5 120.00(8) . . ?
C4 C5 C6 118.57(8) . . ?
C7 C6 C5 120.12(8) . . ?
N1 C7 C6 119.94(7) . . ?

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 Cl1 -173.65(5) . . . . ?
O1 C1 C2 Cl2 -55.30(7) . . . . ?
O1 C1 C2 Cl3 65.40(7) . . . . ?
O2 C1 C2 Cl1 63.29(7) . . . . ?
O2 C1 C2 Cl2 -178.37(5) . . . . ?
O2 C1 C2 Cl3 -57.66(7) . . . . ?
O3 N1 C3 C4 179.03(7) . . . . ?
O3 N1 C7 C6 -178.97(7) . . . . ?
N1 C3 C4 C5 0.16(13) . . . . ?
C3 N1 C7 C6 0.98(12) . . . . ?
C3 C4 C5 C6 0.51(13) . . . . ?
C4 C5 C6 C7 -0.46(13) . . . . ?
C5 C6 C7 N1 -0.28(12) . . . . ?
C7 N1 C3 C4 -0.92(12) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
