# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_LT
_database_code_depnum_ccdc_archive 'CCDC 1863126'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H14 Cl N O5'
_chemical_formula_weight         227.64

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   11.7255(6)
_cell_length_b                   8.2616(6)
_cell_length_c                   10.4236(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1009.75(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5091
_cell_measurement_theta_min      2.615
_cell_measurement_theta_max      24.994

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             480.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.376
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5091
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.615
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             955
_reflns_number_gt                834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2900P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         945
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0956
_refine_ls_wR_factor_ref         0.3265
_refine_ls_wR_factor_gt          0.3086
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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_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 0.08692(9) 0.2500 0.13300(12) 0.0405(8) Uani 1 2 d S T P . .
N1 N 0.2296(3) 0.2500 0.7491(4) 0.0351(11) Uani 1 2 d S T P . .
C1 C 0.3167(4) 0.2500 0.6446(5) 0.0419(13) Uani 1 2 d S T P . .
H1A H 0.3652 0.1538 0.6514 0.050 Uiso 0.5 1 calc R U P . .
H1B H 0.3652 0.3462 0.6514 0.050 Uiso 0.5 1 calc R U P . .
C2 C 0.2542(5) 0.2500 0.5171(6) 0.070(2) Uani 1 2 d S T P . .
H2A H 0.2759 0.1540 0.4677 0.084 Uiso 0.5 1 calc R U P . .
H2B H 0.2759 0.3460 0.4677 0.084 Uiso 0.5 1 calc R U P . .
C3 C 0.1253(4) 0.2500 0.5389(6) 0.0563(16) Uani 1 2 d S T P . .
H3 H 0.0847 0.2500 0.4556 0.068 Uiso 1 2 calc R U P . .
O1 O 0.2948(3) 0.2500 0.8646(3) 0.0562(14) Uani 1 2 d S T P . .
H1 H 0.2548 0.2162 0.9246 0.084 Uiso 0.5 1 calc R U P . .
C4 C 0.0938(3) 0.0995(8) 0.6160(5) 0.0577(14) Uani 1 1 d . . . . .
H4A H 0.1139 0.0020 0.5674 0.069 Uiso 1 1 calc R U . . .
H4B H 0.0114 0.0978 0.6319 0.069 Uiso 1 1 calc R U . . .
C5 C 0.1582(3) 0.1017(5) 0.7435(3) 0.0467(11) Uani 1 1 d . . . . .
H5A H 0.1040 0.1010 0.8150 0.056 Uiso 1 1 calc R U . . .
H5B H 0.2066 0.0054 0.7505 0.056 Uiso 1 1 calc R U . . .
O3 O 0.2022(7) 0.2500 0.0917(8) 0.167(5) Uani 1 2 d S T P . .
O2 O 0.0662(10) 0.1192(8) 0.2128(11) 0.184(4) Uani 1 1 d . . . . .
O4 O 0.0248(7) 0.2500 0.0255(9) 0.258(9) Uani 1 2 d S T P . .

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 0.0418(11) 0.0401(11) 0.0396(12) 0.000 0.0036(4) 0.000
N1 0.0327(18) 0.047(2) 0.026(2) 0.000 -0.0005(13) 0.000
C1 0.031(2) 0.051(3) 0.044(3) 0.000 0.0075(16) 0.000
C2 0.046(3) 0.127(7) 0.037(3) 0.000 0.008(2) 0.000
C3 0.041(3) 0.092(4) 0.036(3) 0.000 -0.0066(19) 0.000
O1 0.040(2) 0.096(4) 0.032(2) 0.000 -0.0112(11) 0.000
C4 0.054(2) 0.063(3) 0.056(3) -0.016(2) -0.0064(14) -0.0067(17)
C5 0.047(2) 0.050(2) 0.043(2) 0.0062(13) 0.0042(14) -0.0076(14)
O3 0.085(5) 0.325(15) 0.090(5) 0.000 0.031(4) 0.000
O2 0.283(11) 0.083(4) 0.186(8) 0.010(5) 0.079(7) -0.053(5)
O4 0.081(5) 0.61(3) 0.084(6) 0.000 -0.012(3) 0.000

_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 O4 1.336(8) . ?
Cl1 O2 1.385(7) . ?
Cl1 O2 1.385(7) 7_565 ?
Cl1 O3 1.419(7) . ?
N1 O1 1.425(5) . ?
N1 C5 1.485(4) . ?
N1 C5 1.485(4) 7_565 ?
N1 C1 1.494(6) . ?
C1 C2 1.517(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.529(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.526(7) . ?
C3 C4 1.526(7) 7_565 ?
C3 H3 0.9900 . ?
O1 H1 0.8300 . ?
C4 C5 1.529(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?

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
O4 Cl1 O2 114.1(6) . . ?
O4 Cl1 O2 114.1(6) . 7_565 ?
O2 Cl1 O2 102.6(8) . 7_565 ?
O4 Cl1 O3 105.4(5) . . ?
O2 Cl1 O3 110.4(6) . . ?
O2 Cl1 O3 110.4(6) 7_565 . ?
O1 N1 C5 109.6(2) . . ?
O1 N1 C5 109.6(2) . 7_565 ?
C5 N1 C5 111.2(4) . 7_565 ?
O1 N1 C1 104.4(4) . . ?
C5 N1 C1 110.9(2) . . ?
C5 N1 C1 110.9(2) 7_565 . ?
N1 C1 C2 108.0(4) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
C1 C2 C3 110.4(4) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C4 109.2(5) . 7_565 ?
C4 C3 C2 108.5(3) . . ?
C4 C3 C2 108.5(3) 7_565 . ?
C4 C3 H3 110.2 . . ?
C4 C3 H3 110.2 7_565 . ?
C2 C3 H3 110.2 . . ?
N1 O1 H1 109.5 . . ?
C3 C4 C5 109.2(4) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C4 108.8(4) . . ?
N1 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556
C1 H1A O2 0.98 2.48 3.420(9) 160.9 2
C1 H1B O2 0.98 2.48 3.420(9) 160.9 8_666
O1 H1 Cl1 0.83 2.95 3.711(4) 154.4 1_556
O1 H1 O3 0.83 1.87 2.605(8) 147.0 1_556
C4 H4B O2 0.98 2.58 3.158(9) 117.6 5_556

_refine_diff_density_max         0.896
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.119

_shelx_res_file                  
;

    LT.res created by SHELXL-2014/7

TITL LT in Pnma
CELL 0.71073  11.7255   8.2616  10.4236  90.000  90.000  90.000
ZERR   13.00   0.0006   0.0006   0.0007   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, 0.5-Z
SFAC C  H  N  O  Cl
UNIT 13 13 13 13 13
OMIT 4   2   1
OMIT 2   1   4
OMIT 6   6   1
OMIT 4   1   2
OMIT 1   4   6
OMIT 3   6   1
OMIT 8   5   1
OMIT 6   0   2
OMIT 5   2   2
OMIT 4   4   0
OMIT   0.00  50.00
L.S. 20
ACTA
BOND $H
FMAP 2
PLAN 2
HTAB C4 O2_$4
HTAB O1 O3_$1
HTAB O1 Cl1_$1
HTAB C1 O2_$3
HTAB C1 O2_$2
HTAB C4 O2_$4
HTAB O1 O3_$1
HTAB O1 Cl1_$1
HTAB C1 O2_$3
HTAB C1 O2_$2
HTAB C4 O2_$4
HTAB O1 O3_$1
HTAB O1 Cl1_$1
HTAB C1 O2_$3
HTAB C1 O2_$2
HTAB C4 O2_$4
HTAB O1 O3_$1
HTAB O1 Cl1_$1
HTAB C1 O2_$3
HTAB C1 O2_$2
HTAB C4 O2_$4
HTAB O1 O3_$1
HTAB O1 Cl1_$1
HTAB C1 O2_$3
HTAB C1 O2_$2
HTAB C4 O2_$4
HTAB O1 O3_$1
HTAB C1 O2_$3
HTAB C1 O2_$2
HTAB C4 O2_$4
HTAB O1 O3_$1
HTAB O1 Cl1_$1
HTAB C1 O2_$3
HTAB C1 O2_$2
HTAB C4 O2_$4
HTAB C1 O2_$3
HTAB C1 O2_$2
HTAB
EQIV $1 x, y, z+1
HTAB O1 O3_$1
EQIV $2 -x+1/2, -y, z+1/2
HTAB C1 O2_$2
EQIV $3 -x+1/2, y+1/2, z+1/2
HTAB C1 O2_$3
EQIV $4 -x, -y, -z+1
HTAB C4 O2_$4
HTAB C1 O2_$2
HTAB C1 O2_$3
HTAB O1 O3_$1
HTAB C4 O2_$4
HTAB C1 O2_$2
HTAB C1 O2_$3
HTAB O1 Cl1_$1
HTAB O1 O3_$1
HTAB C4 O2_$4
HTAB C1 O2_$2
HTAB C1 O2_$3
HTAB O1 Cl1_$1
HTAB O1 O3_$1
HTAB C4 O2_$4
HTAB C1 O2_$2
HTAB C1 O2_$3
HTAB O1 Cl1_$1
HTAB O1 O3_$1
HTAB C4 O2_$4
HTAB C1 O2_$2
HTAB C1 O2_$3
HTAB O1 Cl1_$1
HTAB O1 O3_$1
HTAB C4 O2_$4
HTAB C1 O2_$2
HTAB C1 O2_$3
HTAB O1 Cl1_$1
HTAB O1 O3_$1
HTAB C4 O2_$4
HTAB C1 O2_$2
HTAB C1 O2_$3
HTAB O1 Cl1_$1
HTAB O1 O3_$1
HTAB C4 O2_$4
TEMP -50
WGHT    0.290000
FVAR       0.19741
CL1   5    0.086918    0.250000    0.132996    10.50000    0.04178    0.04011 =
         0.03962    0.00000    0.00357    0.00000
N1    3    0.229617    0.250000    0.749140    10.50000    0.03269    0.04654 =
         0.02612    0.00000   -0.00049    0.00000
C1    1    0.316727    0.250000    0.644557    10.50000    0.03077    0.05124 =
         0.04376    0.00000    0.00748    0.00000
AFIX  23
H1A   2    0.365220    0.153770    0.651368    10.50000   -1.20000
H1B   2    0.365220    0.346230    0.651368    10.50000   -1.20000
AFIX   0
C2    1    0.254191    0.250000    0.517132    10.50000    0.04590    0.12712 =
         0.03727    0.00000    0.00751    0.00000
AFIX  23
H2A   2    0.275911    0.153962    0.467652    10.50000   -1.20000
H2B   2    0.275911    0.346038    0.467652    10.50000   -1.20000
AFIX   0
C3    1    0.125262    0.250000    0.538904    10.50000    0.04137    0.09158 =
         0.03608    0.00000   -0.00655    0.00000
AFIX  13
H3    2    0.084670    0.249999    0.455624    10.50000   -1.20000
AFIX   0
O1    4    0.294803    0.250000    0.864564    10.50000    0.04043    0.09565 =
         0.03245    0.00000   -0.01122    0.00000
AFIX 147
H1    2    0.254823    0.216240    0.924580    10.50000   -1.50000
AFIX   0
C4    1    0.093753    0.099502    0.615974    11.00000    0.05377    0.06323 =
         0.05607   -0.01552   -0.00638   -0.00668
AFIX  23
H4A   2    0.113897    0.002021    0.567432    11.00000   -1.20000
H4B   2    0.011396    0.097832    0.631934    11.00000   -1.20000
AFIX   0
C5    1    0.158188    0.101692    0.743499    11.00000    0.04720    0.04957 =
         0.04333    0.00617    0.00420   -0.00764
AFIX  23
H5A   2    0.103953    0.100983    0.815032    11.00000   -1.20000
H5B   2    0.206555    0.005352    0.750462    11.00000   -1.20000
AFIX   0
O3    4    0.202205    0.250000    0.091716    10.50000    0.08532    0.32477 =
         0.09011    0.00000    0.03060    0.00000
O2    4    0.066237    0.119216    0.212785    11.00000    0.28308    0.08324 =
         0.18576    0.01036    0.07945   -0.05255
O4    4    0.024787    0.250000    0.025517    10.50000    0.08091    0.60834 =
         0.08434    0.00000   -0.01246    0.00000
HKLF 4

REM  LT in Pnma
REM R1 =  0.0956 for     834 Fo > 4sig(Fo)  and  0.1009 for all     945 data
REM     77 parameters refined using      0 restraints

END

WGHT      0.2000      0.0000

REM Instructions for potential hydrogen bonds
HTAB C1 O2_$2
HTAB C1 O2_$3
HTAB O1 Cl1_$1
HTAB O1 O3_$1
HTAB C4 O2_$4

REM Highest difference peak  0.896,  deepest hole -0.708,  1-sigma level  0.119
Q1    1   0.0473  0.1100  0.0676  11.00000  0.05    0.90
Q2    1   0.1343  0.1428  0.0433  11.00000  0.05    0.87
;
_shelx_res_checksum              57677
####################################################################### 
# 
# 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_HT
_database_code_depnum_ccdc_archive 'CCDC 1863127'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H14 N O, Cl O4'
_chemical_formula_sum            'C7 H14 Cl N O5'
_chemical_formula_weight         227.64

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'

_space_group_crystal_system      cubic
_space_group_IT_number           221
_space_group_name_H-M_alt        'P m -3 m'
_space_group_name_Hall           '-P 4 2 3'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'

_cell_length_a                   6.4782(8)
_cell_length_b                   6.4782(8)
_cell_length_c                   6.4782(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     271.87(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    353(2)
_cell_measurement_reflns_used    277
_cell_measurement_theta_min      3.145
_cell_measurement_theta_max      24.920

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             106.6
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.338
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      353(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            277
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_av_R_equivalents  0.1755
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         24.920
_diffrn_reflns_theta_full        24.920
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             72
_reflns_number_gt                37
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         70
_refine_ls_number_parameters     10
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1864
_refine_ls_R_factor_gt           0.1552
_refine_ls_wR_factor_ref         0.3987
_refine_ls_wR_factor_gt          0.3544
_refine_ls_goodness_of_fit_ref   1.258
_refine_ls_restrained_S_all      1.258
_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_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 0.0000 0.0000 0.0000 0.139(8) Uani 1 48 d S T P . .
C1 C 0.338(2) 0.338(2) 0.5000 0.249(16) Uani 0.8 4 d S T P . .
O1 O 0.0000 0.209(7) 0.0000 0.296(17) Uani 0.6666 8 d S T P . .

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 0.139(8) 0.139(8) 0.139(8) 0.000 0.000 0.000
C1 0.240(18) 0.240(18) 0.27(3) 0.000 0.000 -0.054(14)
O1 0.30(3) 0.29(4) 0.30(3) 0.000 0.000 0.000

_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 O1 1.35(4) 33 ?
Cl1 O1 1.35(4) 9 ?
Cl1 O1 1.35(4) 25 ?
Cl1 O1 1.35(4) 5 ?
Cl1 O1 1.35(4) 29 ?
Cl1 O1 1.35(4) . ?
C1 C1 1.487(19) 11_566 ?
C1 C1 1.487(19) 31_556 ?
C1 C1 1.487(19) 5 ?
C1 C1 1.487(19) 9 ?

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 Cl1 O1 180.0 33 9 ?
O1 Cl1 O1 90.000(1) 33 25 ?
O1 Cl1 O1 90.000(1) 9 25 ?
O1 Cl1 O1 90.000(1) 33 5 ?
O1 Cl1 O1 90.000(1) 9 5 ?
O1 Cl1 O1 90.000(1) 25 5 ?
O1 Cl1 O1 90.000(1) 33 29 ?
O1 Cl1 O1 90.000(1) 9 29 ?
O1 Cl1 O1 90.000(1) 25 29 ?
O1 Cl1 O1 180.0 5 29 ?
O1 Cl1 O1 90.000(1) 33 . ?
O1 Cl1 O1 90.000(1) 9 . ?
O1 Cl1 O1 180.0 25 . ?
O1 Cl1 O1 90.0 5 . ?
O1 Cl1 O1 90.0 29 . ?
C1 C1 C1 60.0 11_566 31_556 ?
C1 C1 C1 120.002(10) 11_566 5 ?
C1 C1 C1 90.001(7) 31_556 5 ?
C1 C1 C1 90.001(5) 11_566 9 ?
C1 C1 C1 120.002(9) 31_556 9 ?
C1 C1 C1 60.0 5 9 ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.121



# start Validation Reply Form

_vrf_DENSD01_HT                  
;
PROBLEM: The ratio of the submitted crystal density and that
            calculated from the formula is outside the range 0.95 <> 1.05
            Crystal density given    =      1.312
            Calculated crystal density =      1.390   
RESPONSE: The mistake was caused by the disorder behaviour.
;
_vrf_PLAT043_HT                  
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      12.90 Check   
RESPONSE: The mistake was caused by the disorder behaviour.
;
_vrf_PLAT082_HT                  
;
PROBLEM: High R1 Value ..................................       0.16 Report  
RESPONSE: High temperature resulted in poor quality of the crystal.
;
_vrf_PLAT084_HT                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.40 Report  
RESPONSE: High temperature resulted in poor quality of the crystal.
;
_vrf_PLAT088_HT                  
;
PROBLEM:  Poor Data / Parameter Ratio ....................       7.20 Note  
RESPONSE: High temperature resulted in poor quality of the crystal.
;
# end Validation Reply Form







_HT_res_file                     
;

    HT.res created by SHELXL-2014/7

TITL 1 in Pm-3m
CELL 0.71073   6.4782   6.4782   6.4782  90.000  90.000  90.000
ZERR   1  0.0008   0.0008   0.0008   0.000   0.000   0.000
LATT 1
SYMM -X, -Y, Z
SYMM -X, Y, -Z
SYMM X, -Y, -Z
SYMM Z, X, Y
SYMM Z, -X, -Y
SYMM -Z, -X, Y
SYMM -Z, X, -Y
SYMM Y, Z, X
SYMM -Y, Z, -X
SYMM Y, -Z, -X
SYMM -Y, -Z, X
SYMM Y, X, -Z
SYMM -Y, -X, -Z
SYMM Y, -X, Z
SYMM -Y, X, Z
SYMM X, Z, -Y
SYMM -X, Z, Y
SYMM -X, -Z, -Y
SYMM X, -Z, Y
SYMM Z, Y, -X
SYMM Z, -Y, X
SYMM -Z, Y, X
SYMM -Z, -Y, -X
SFAC C  H  N  O  Cl
UNIT 7 14 1 5 1
OMIT 1 1 1
OMIT 1 2 3
OMIT  -3.00  50.00
L.S. 40
ACTA
BOND
FMAP 2
PLAN 1
TEMP 73
WGHT    0.200000
FVAR       1.68553   0.66667
CL1   5    0.000000    0.000000    0.000000    10.02083    0.13929    0.13929 =
         0.13929    0.00000    0.00000    0.00000
C1    1    0.337665    0.337665    0.500000    10.20000    0.24009    0.24009 =
         0.26612    0.00000    0.00000   -0.05435
O1    4    0.000000    0.208764    0.000000    10.08333    0.29754    0.29403 =
         0.29754    0.00000    0.00000    0.00000
HKLF 4

REM  HT in Pm-3m
REM R1 =  0.1552 for      37 Fo > 4sig(Fo)  and  0.1864 for all      70 data
REM     10 parameters refined using      0 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.472,  deepest hole -0.246,  1-sigma level  0.121
Q1    1   0.5000  0.5000  0.5000  10.02083  0.05    0.26
;
_shelx_res_checksum              69268
