# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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).
# 
# 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_200K
_database_code_depnum_ccdc_archive 'CCDC 1019423'
_audit_update_record             
;
2014-08-14 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H11 Cl N2 O4'
_chemical_formula_weight         186.60

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.8955(8)
_cell_length_b                   7.9685(10)
_cell_length_c                   12.611(2)
_cell_angle_alpha                84.587(14)
_cell_angle_beta                 88.678(14)
_cell_angle_gamma                76.076(10)
_cell_volume                     766.66(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    3535
_cell_measurement_theta_min      2.6377
_cell_measurement_theta_max      29.6921

_exptl_crystal_description       transparent
_exptl_crystal_colour            colourles
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_T_min  0.99616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7672
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.68
_reflns_number_total             4414
_reflns_number_gt                2831
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0640P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0082(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.25(11)
_refine_ls_number_reflns         4414
_refine_ls_number_parameters     245
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.004
_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 0.77096(11) 0.20418(11) 0.01946(8) 0.0218(5) Uani 1 1 d . . .
O1 O 0.6496(3) 0.3661(4) 0.0264(2) 0.0371(17) Uani 1 1 d . . .
O2 O 0.6764(4) 0.0731(4) 0.0075(2) 0.0390(17) Uani 1 1 d . . .
O3 O 0.8684(5) 0.1564(4) 0.1157(3) 0.070(3) Uani 1 1 d . . .
O4 O 0.8771(5) 0.2130(5) -0.0708(3) 0.077(3) Uani 1 1 d U . .
Cl2 Cl 0.71828(11) 0.28946(12) 0.48498(7) 0.0213(5) Uani 1 1 d . . .
O5 O 0.8342(4) 0.1258(4) 0.4735(2) 0.0458(19) Uani 1 1 d . . .
O6 O 0.6093(5) 0.3402(5) 0.3942(3) 0.075(3) Uani 1 1 d . . .
O7 O 0.8161(4) 0.4166(4) 0.4937(3) 0.0467(19) Uani 1 1 d . . .
O8 O 0.6187(5) 0.2811(6) 0.5793(3) 0.089(3) Uani 1 1 d U . .
N1 N 0.6018(4) 0.8865(4) 0.2053(3) 0.0223(16) Uani 1 1 d . . .
H1A H 0.4893 0.9442 0.2098 0.027 Uiso 0.5 1 calc PR . .
H1B H 0.6492 0.9344 0.1481 0.027 Uiso 1 1 calc PR . .
N2 N 0.8957(8) 0.6216(8) 0.2895(5) 0.0243(16) Uani 1 1 d . . .
H2A H 0.8500 0.5755 0.3480 0.029 Uiso 1 1 calc PR . .
H2B H 1.0091 0.5665 0.2854 0.029 Uiso 0.5 1 calc PR . .
C1 C 0.6981(11) 0.9034(12) 0.3052(7) 0.0295(19) Uani 1 1 d . . .
H1C H 0.6924 1.0247 0.3125 0.035 Uiso 1 1 calc R . .
H1D H 0.6445 0.8567 0.3676 0.035 Uiso 1 1 calc R . .
C2 C 0.8789(9) 0.8081(8) 0.2968(6) 0.0221(17) Uani 1 1 d . . .
H2C H 0.9428 0.8231 0.3586 0.026 Uiso 1 1 calc R . .
H2D H 0.9308 0.8558 0.2341 0.026 Uiso 1 1 calc R . .
C3 C 0.8019(10) 0.5985(11) 0.1932(7) 0.0210(18) Uani 1 1 d . . .
H3A H 0.8048 0.4765 0.1913 0.025 Uiso 1 1 calc R . .
H3B H 0.8609 0.6352 0.1301 0.025 Uiso 1 1 calc R . .
C4 C 0.6118(8) 0.7034(9) 0.1921(6) 0.0197(18) Uani 1 1 d . . .
H4A H 0.5578 0.6946 0.1252 0.024 Uiso 1 1 calc R . .
H4B H 0.5481 0.6557 0.2493 0.024 Uiso 1 1 calc R . .
N3 N 0.2484(8) 0.4047(8) 0.3074(6) 0.0262(17) Uani 1 1 d . . .
H3C H 0.1415 0.4734 0.2933 0.031 Uiso 0.5 1 calc PR . .
H3D H 0.3045 0.4603 0.3485 0.031 Uiso 1 1 calc PR . .
N4 N 0.2558(8) 0.1042(9) 0.1978(5) 0.0246(16) Uani 1 1 d . . .
H4C H 0.3654 0.0440 0.2137 0.030 Uiso 0.5 1 calc PR . .
H4D H 0.2066 0.0414 0.1575 0.030 Uiso 1 1 calc PR . .
C5 C 0.3424(10) 0.3777(10) 0.2088(7) 0.0256(19) Uani 1 1 d . . .
H5A H 0.4624 0.3163 0.2239 0.031 Uiso 1 1 calc R . .
H5B H 0.3429 0.4890 0.1706 0.031 Uiso 1 1 calc R . .
C6 C 0.2580(10) 0.2723(10) 0.1393(6) 0.0238(19) Uani 1 1 d . . .
H6A H 0.1398 0.3358 0.1212 0.029 Uiso 1 1 calc R . .
H6B H 0.3237 0.2536 0.0738 0.029 Uiso 1 1 calc R . .
C7 C 0.1510(9) 0.1388(10) 0.2995(7) 0.0228(18) Uani 1 1 d . . .
H7A H 0.0327 0.2024 0.2814 0.027 Uiso 1 1 calc R . .
H7B H 0.1455 0.0292 0.3383 0.027 Uiso 1 1 calc R . .
C8 C 0.23000(5) 0.23943(5) 0.36754(4) 0.0185(16) Uani 1 1 d . . .
H8A H 0.3439 0.1713 0.3915 0.022 Uiso 1 1 calc R . .
H8B H 0.1574 0.2654 0.4298 0.022 Uiso 1 1 calc R . .
Cl3 Cl 0.22922(5) 0.79603(5) 0.98032(4) 0.0247(5) Uani 1 1 d R . .
O9 O 0.35018(5) 0.63275(5) 0.97331(4) 0.0442(19) Uani 1 1 d R . .
O10 O 0.32311(5) 0.92773(5) 0.99274(4) 0.0431(17) Uani 1 1 d R . .
O11 O 0.13298(5) 0.84339(5) 0.88408(4) 0.069(3) Uani 1 1 d RU . .
O12 O 0.12428(5) 0.78685(5) 1.07147(4) 0.086(3) Uani 1 1 d R . .
Cl4 Cl 0.28205(5) 0.71064(5) 0.51492(4) 0.0273(6) Uani 1 1 d R . .
O13 O 0.16608(5) 0.87474(5) 0.52663(4) 0.0399(17) Uani 1 1 d R . .
O14 O 0.38923(5) 0.65784(5) 0.60726(4) 0.060(2) Uani 1 1 d R . .
O15 O 0.18458(5) 0.58294(5) 0.50594(4) 0.0454(18) Uani 1 1 d R . .
O16 O 0.37933(5) 0.71791(5) 0.41933(4) 0.077(3) Uani 1 1 d R . .
N5 N 0.39700(5) 0.11347(5) 0.79504(4) 0.0191(15) Uani 1 1 d R . .
H5C H 0.5102 0.0583 0.7898 0.023 Uiso 0.5 1 calc PR . .
H5D H 0.3532 0.0660 0.8538 0.023 Uiso 1 1 calc PR . .
N6 N 0.1000(7) 0.3850(7) 0.7153(5) 0.0197(15) Uani 1 1 d . . .
H6C H 0.1433 0.4368 0.6580 0.024 Uiso 1 1 calc PR . .
H6D H -0.0126 0.4409 0.7226 0.024 Uiso 0.5 1 calc PR . .
C9 C 0.3024(9) 0.0883(10) 0.7006(6) 0.0192(16) Uani 1 1 d . . .
H9A H 0.2996 -0.0329 0.7018 0.023 Uiso 1 1 calc R . .
H9B H 0.3635 0.1181 0.6367 0.023 Uiso 1 1 calc R . .
C10 C 0.1097(8) 0.2044(9) 0.6977(6) 0.0217(18) Uani 1 1 d . . .
H10A H 0.0584 0.2008 0.6291 0.026 Uiso 1 1 calc R . .
H10B H 0.0414 0.1560 0.7519 0.026 Uiso 1 1 calc R . .
C11 C 0.1955(10) 0.3998(11) 0.8089(7) 0.0249(19) Uani 1 1 d . . .
H11A H 0.1406 0.3554 0.8714 0.030 Uiso 1 1 calc R . .
H11B H 0.1893 0.5215 0.8153 0.030 Uiso 1 1 calc R . .
C12 C 0.3829(10) 0.3036(9) 0.8061(7) 0.028(2) Uani 1 1 d . . .
H12A H 0.4404 0.3158 0.8711 0.033 Uiso 1 1 calc R . .
H12B H 0.4409 0.3524 0.7465 0.033 Uiso 1 1 calc R . .
N7 N 0.7560(7) 0.5926(8) 0.6917(5) 0.0181(15) Uani 1 1 d . . .
H7C H 0.8637 0.5248 0.7047 0.022 Uiso 0.5 1 calc PR . .
H7D H 0.6989 0.5367 0.6514 0.022 Uiso 1 1 calc PR . .
N8 N 0.7496(8) 0.8958(8) 0.7975(5) 0.0199(15) Uani 1 1 d . . .
H8C H 0.6412 0.9560 0.7786 0.024 Uiso 0.5 1 calc PR . .
H8D H 0.7957 0.9607 0.8380 0.024 Uiso 1 1 calc PR . .
C13 C 0.6586(9) 0.6243(10) 0.7974(6) 0.0215(17) Uani 1 1 d . . .
H13A H 0.5374 0.6824 0.7833 0.026 Uiso 1 1 calc R . .
H13B H 0.6620 0.5140 0.8381 0.026 Uiso 1 1 calc R . .
C14 C 0.7399(10) 0.7328(10) 0.8601(6) 0.0228(18) Uani 1 1 d . . .
H14A H 0.6719 0.7591 0.9241 0.027 Uiso 1 1 calc R . .
H14B H 0.8565 0.6685 0.8815 0.027 Uiso 1 1 calc R . .
C15 C 0.8528(10) 0.8643(11) 0.7048(7) 0.0231(18) Uani 1 1 d . . .
H15A H 0.9699 0.7994 0.7246 0.028 Uiso 1 1 calc R . .
H15B H 0.8604 0.9737 0.6666 0.028 Uiso 1 1 calc R . .
C16 C 0.7696(6) 0.7602(6) 0.6327(3) 0.031(2) Uani 1 1 d . . .
H16A H 0.6544 0.8273 0.6106 0.037 Uiso 1 1 calc R . .
H16B H 0.8405 0.7374 0.5694 0.037 Uiso 1 1 calc R . .


_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 1.404(3) . ?
Cl1 O1 1.419(3) . ?
Cl1 O3 1.424(3) . ?
Cl1 O2 1.442(3) . ?
Cl2 O6 1.416(3) . ?
Cl2 O8 1.416(3) . ?
Cl2 O5 1.419(3) . ?
Cl2 O7 1.427(3) . ?
N1 C4 1.467(8) . ?
N1 C1 1.519(8) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C2 1.471(9) . ?
N2 C3 1.485(9) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
C1 C2 1.453(10) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.532(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N3 C5 1.440(10) . ?
N3 C8 1.493(7) . ?
N3 H3C 0.9000 . ?
N3 H3D 0.9000 . ?
N4 C6 1.470(11) . ?
N4 C7 1.521(9) . ?
N4 H4C 0.9000 . ?
N4 H4D 0.9000 . ?
C5 C6 1.534(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.471(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
Cl3 O12 1.4081 . ?
Cl3 O11 1.4181 . ?
Cl3 O9 1.4257 . ?
Cl3 O10 1.4443 . ?
Cl4 O16 1.4184 . ?
Cl4 O13 1.4227 . ?
Cl4 O14 1.4251 . ?
Cl4 O15 1.4294 . ?
N5 C9 1.475(8) . ?
N5 C12 1.511(7) . ?
N5 H5C 0.9000 . ?
N5 H5D 0.9000 . ?
N6 C11 1.444(10) . ?
N6 C10 1.461(9) . ?
N6 H6C 0.9000 . ?
N6 H6D 0.9000 . ?
C9 C10 1.578(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.495(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N7 C16 1.492(8) . ?
N7 C13 1.535(8) . ?
N7 H7C 0.9000 . ?
N7 H7D 0.9000 . ?
N8 C15 1.416(9) . ?
N8 C14 1.473(10) . ?
N8 H8C 0.9000 . ?
N8 H8D 0.9000 . ?
C13 C14 1.484(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.542(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 O1 109.9(2) . . ?
O4 Cl1 O3 112.8(3) . . ?
O1 Cl1 O3 109.6(2) . . ?
O4 Cl1 O2 107.9(2) . . ?
O1 Cl1 O2 108.86(18) . . ?
O3 Cl1 O2 107.6(2) . . ?
O6 Cl2 O8 111.2(3) . . ?
O6 Cl2 O5 109.7(2) . . ?
O8 Cl2 O5 110.1(2) . . ?
O6 Cl2 O7 108.5(2) . . ?
O8 Cl2 O7 107.7(3) . . ?
O5 Cl2 O7 109.5(2) . . ?
C4 N1 C1 110.7(5) . . ?
C4 N1 H1A 109.5 . . ?
C1 N1 H1A 109.4 . . ?
C4 N1 H1B 109.5 . . ?
C1 N1 H1B 109.6 . . ?
H1A N1 H1B 108.1 . . ?
C2 N2 C3 109.1(6) . . ?
C2 N2 H2A 109.9 . . ?
C3 N2 H2A 109.8 . . ?
C2 N2 H2B 109.8 . . ?
C3 N2 H2B 109.9 . . ?
H2A N2 H2B 108.3 . . ?
C2 C1 N1 108.6(6) . . ?
C2 C1 H1C 109.9 . . ?
N1 C1 H1C 110.0 . . ?
C2 C1 H1D 110.0 . . ?
N1 C1 H1D 110.0 . . ?
H1C C1 H1D 108.3 . . ?
C1 C2 N2 112.3(6) . . ?
C1 C2 H2C 109.1 . . ?
N2 C2 H2C 109.1 . . ?
C1 C2 H2D 109.2 . . ?
N2 C2 H2D 109.2 . . ?
H2C C2 H2D 107.9 . . ?
N2 C3 C4 111.6(6) . . ?
N2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C3 110.8(6) . . ?
N1 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.1 . . ?
C5 N3 C8 112.9(5) . . ?
C5 N3 H3C 109.0 . . ?
C8 N3 H3C 109.1 . . ?
C5 N3 H3D 109.0 . . ?
C8 N3 H3D 109.0 . . ?
H3C N3 H3D 107.8 . . ?
C6 N4 C7 108.2(6) . . ?
C6 N4 H4C 110.0 . . ?
C7 N4 H4C 110.1 . . ?
C6 N4 H4D 110.0 . . ?
C7 N4 H4D 110.1 . . ?
H4C N4 H4D 108.4 . . ?
N3 C5 C6 110.7(6) . . ?
N3 C5 H5A 109.5 . . ?
C6 C5 H5A 109.4 . . ?
N3 C5 H5B 109.6 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N4 C6 C5 109.4(7) . . ?
N4 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N4 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 N4 111.2(5) . . ?
C8 C7 H7A 109.4 . . ?
N4 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
N4 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 N3 110.3(4) . . ?
C7 C8 H8A 109.6 . . ?
N3 C8 H8A 109.6 . . ?
C7 C8 H8B 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O12 Cl3 O11 113.7 . . ?
O12 Cl3 O9 109.5 . . ?
O11 Cl3 O9 109.2 . . ?
O12 Cl3 O10 107.3 . . ?
O11 Cl3 O10 107.6 . . ?
O9 Cl3 O10 109.5 . . ?
O16 Cl4 O13 110.2 . . ?
O16 Cl4 O14 113.1 . . ?
O13 Cl4 O14 109.5 . . ?
O16 Cl4 O15 106.6 . . ?
O13 Cl4 O15 109.8 . . ?
O14 Cl4 O15 107.6 . . ?
C9 N5 C12 111.7(4) . . ?
C9 N5 H5C 109.3 . . ?
C12 N5 H5C 109.3 . . ?
C9 N5 H5D 109.2 . . ?
C12 N5 H5D 109.3 . . ?
H5C N5 H5D 107.9 . . ?
C11 N6 C10 112.2(6) . . ?
C11 N6 H6C 109.2 . . ?
C10 N6 H6C 109.2 . . ?
C11 N6 H6D 109.1 . . ?
C10 N6 H6D 109.2 . . ?
H6C N6 H6D 107.9 . . ?
N5 C9 C10 111.2(5) . . ?
N5 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N5 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N6 C10 C9 113.1(6) . . ?
N6 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N6 C10 H10B 109.0 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
N6 C11 C12 112.9(6) . . ?
N6 C11 H11A 109.0 . . ?
C12 C11 H11A 109.1 . . ?
N6 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 N5 110.3(6) . . ?
C11 C12 H12A 109.5 . . ?
N5 C12 H12A 109.6 . . ?
C11 C12 H12B 109.7 . . ?
N5 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C16 N7 C13 110.7(5) . . ?
C16 N7 H7C 109.4 . . ?
C13 N7 H7C 109.5 . . ?
C16 N7 H7D 109.5 . . ?
C13 N7 H7D 109.5 . . ?
H7C N7 H7D 108.1 . . ?
C15 N8 C14 111.6(6) . . ?
C15 N8 H8C 109.3 . . ?
C14 N8 H8C 109.4 . . ?
C15 N8 H8D 109.2 . . ?
C14 N8 H8D 109.3 . . ?
H8C N8 H8D 108.0 . . ?
C14 C13 N7 110.3(6) . . ?
C14 C13 H13A 109.7 . . ?
N7 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
N7 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
N8 C14 C13 111.1(7) . . ?
N8 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
N8 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
N8 C15 C16 109.4(6) . . ?
N8 C15 H15A 109.8 . . ?
C16 C15 H15A 109.7 . . ?
N8 C15 H15B 109.9 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
N7 C16 C15 109.9(5) . . ?
N7 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
N7 C16 H16B 109.7 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?



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

N1 H1A N4 0.90 1.97 2.856(7) 168.7 1_565
N4 H4C N1 0.90 1.98 2.856(7) 162.9 1_545
N1 H1B O2 0.90 2.03 2.901(4) 162.2 1_565
N2 H2A O7 0.90 2.17 3.053(8) 163.4 .
N3 H3C N2 0.90 2.01 2.902(9) 169.6 1_455
N2 H2B N3 0.90 2.02 2.902(9) 166.1 1_655
N3 H3D O15 0.90 2.38 2.963(7) 123.0 .
N3 H3D O16 0.90 2.50 3.356(7) 155.8 .
N4 H4D O10 0.90 2.41 3.035(7) 125.3 1_544
N4 H4D O12 0.90 2.60 3.480(7) 163.7 1_544
N5 H5C N8 0.90 2.02 2.901(6) 167.8 1_545
N8 H8C N5 0.90 2.05 2.901(6) 157.5 1_565
N5 H5D O10 0.90 2.02 2.898 165.0 1_545
N6 H6C O15 0.90 2.21 3.092(6) 166.3 .
N7 H7C N6 0.90 1.93 2.823(8) 173.3 1_655
N6 H6D N7 0.90 1.96 2.823(8) 161.5 1_455
N7 H7D O7 0.90 2.36 2.956(6) 123 .
N7 H7D O14 0.90 2.46 3.017(6) 121 .
N7 H7D O8 0.90 2.53 3.377(8) 157.0 .
N8 H8D O2 0.90 2.48 3.096(7) 127.0 1_566



_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_409K
_database_code_depnum_ccdc_archive 'CCDC 1019424'
_audit_update_record             
;
2014-08-14 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H11 Cl N2 O4'
_chemical_formula_weight         186.60

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0326(8)
_cell_length_b                   8.0754(10)
_cell_length_c                   12.745(2)
_cell_angle_alpha                84.190(14)
_cell_angle_beta                 88.360(14)
_cell_angle_gamma                76.009(10)
_cell_volume                     798.07(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    413(2)
_cell_measurement_reflns_used    2987
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      25.68

_exptl_crystal_description       transparent
_exptl_crystal_colour            colourles
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_min  0.99616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      413(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7153
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.68
_reflns_number_total             2987
_reflns_number_gt                1468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0860P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2987
_refine_ls_number_parameters     236
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.898
_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 0.22775(10) 0.79213(11) 0.98265(7) 0.0550(3) Uani 1 1 d D . .
O1 O 0.3487(3) 0.6370(3) 0.9721(3) 0.1080(11) Uani 1 1 d D . .
O2 O 0.3145(4) 0.9224(4) 0.9908(2) 0.1125(12) Uani 1 1 d D . .
O3 O 0.1654(15) 0.844(2) 0.8803(5) 0.128(5) Uani 0.50 1 d PD . .
O4 O 0.0881(14) 0.8250(18) 0.9143(10) 0.151(6) Uani 0.50 1 d PD . .
O5 O 0.1810(13) 0.7801(16) 1.0893(3) 0.102(3) Uani 0.50 1 d PD . .
O6 O 0.1022(16) 0.767(2) 1.0565(11) 0.203(8) Uani 0.50 1 d PD . .
Cl2 Cl 0.28758(10) 0.71612(11) 0.51128(7) 0.0551(3) Uani 1 1 d D . .
O7 O 0.1665(4) 0.8700(3) 0.5256(2) 0.1014(10) Uani 1 1 d D . .
O8 O 0.1986(5) 0.5845(5) 0.5078(3) 0.1188(12) Uani 1 1 d . . .
O9 O 0.3679(11) 0.6544(15) 0.6067(8) 0.095(3) Uani 0.50 1 d P . .
O10 O 0.4352(11) 0.6877(19) 0.5725(10) 0.169(8) Uani 0.50 1 d PD . .
O11 O 0.3960(19) 0.748(2) 0.4279(10) 0.227(9) Uani 0.50 1 d PD . .
O12 O 0.3336(14) 0.7109(14) 0.4046(3) 0.092(3) Uani 0.50 1 d PD . .
N1 N 0.3943(3) 0.1106(4) 0.7915(2) 0.0556(8) Uani 1 1 d . . .
H1A H 0.5051 0.0560 0.7842 0.067 Uiso 0.50 1 calc PR . .
H1B H 0.3521 0.0587 0.8484 0.067 Uiso 1 1 calc R . .
N2 N 0.1067(3) 0.3802(4) 0.7159(2) 0.0550(8) Uani 1 1 d . . .
H2A H 0.1482 0.4325 0.6589 0.066 Uiso 1 1 calc R . .
H2B H -0.0042 0.4343 0.7236 0.066 Uiso 0.50 1 calc PR . .
C1 C 0.2996(4) 0.0950(5) 0.6979(3) 0.0596(10) Uani 1 1 d . . .
H1C H 0.2970 -0.0240 0.6955 0.072 Uiso 1 1 calc R . .
H1D H 0.3586 0.1299 0.6352 0.072 Uiso 1 1 calc R . .
C2 C 0.1177(4) 0.2044(5) 0.6986(3) 0.0582(10) Uani 1 1 d . . .
H2C H 0.0646 0.2017 0.6316 0.070 Uiso 1 1 calc R . .
H2D H 0.0531 0.1549 0.7534 0.070 Uiso 1 1 calc R . .
C3 C 0.1997(4) 0.3948(4) 0.8069(3) 0.0577(10) Uani 1 1 d . . .
H3A H 0.1408 0.3587 0.8693 0.069 Uiso 1 1 calc R . .
H3B H 0.1995 0.5144 0.8098 0.069 Uiso 1 1 calc R . .
C4 C 0.3837(4) 0.2900(5) 0.8091(3) 0.0601(10) Uani 1 1 d . . .
H4A H 0.4493 0.3398 0.7550 0.072 Uiso 1 1 calc R . .
H4B H 0.4339 0.2937 0.8769 0.072 Uiso 1 1 calc R . .
N3 N 0.7632(3) 0.5977(3) 0.6889(2) 0.0507(7) Uani 1 1 d . . .
H3C H 0.8687 0.5317 0.7043 0.061 Uiso 0.5 1 calc R . .
H3D H 0.7132 0.5434 0.6452 0.061 Uiso 1 1 calc PR . .
N4 N 0.7399(3) 0.8870(3) 0.8025(2) 0.0508(7) Uani 1 1 d . . .
H4C H 0.7809 0.9489 0.8458 0.061 Uiso 1 1 calc PR . .
H4D H 0.6333 0.9453 0.7830 0.061 Uiso 0.5 1 calc R . .
C5 C 0.6603(4) 0.6187(4) 0.7879(3) 0.0553(9) Uani 1 1 d . . .
H5A H 0.6620 0.5070 0.8245 0.066 Uiso 1 1 calc R . .
H5B H 0.5422 0.6760 0.7710 0.066 Uiso 1 1 calc R . .
C6 C 0.7334(4) 0.7225(5) 0.8578(3) 0.0541(9) Uani 1 1 d . . .
H6A H 0.6629 0.7404 0.9206 0.065 Uiso 1 1 calc R . .
H6B H 0.8481 0.6602 0.8795 0.065 Uiso 1 1 calc R . .
C7 C 0.8502(4) 0.8631(4) 0.7087(3) 0.0536(9) Uani 1 1 d . . .
H7A H 0.9655 0.8014 0.7295 0.064 Uiso 1 1 calc R . .
H7B H 0.8556 0.9739 0.6734 0.064 Uiso 1 1 calc R . .
C8 C 0.7789(4) 0.7637(5) 0.6348(3) 0.0555(9) Uani 1 1 d . . .
H8A H 0.6671 0.8297 0.6100 0.067 Uiso 1 1 calc R . .
H8B H 0.8542 0.7442 0.5741 0.067 Uiso 1 1 calc R . .


_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 O6 1.396(2) . ?
Cl1 O4 1.397(2) . ?
Cl1 O3 1.398(2) . ?
Cl1 O1 1.4036(17) . ?
Cl1 O2 1.4080(17) . ?
Cl1 O5 1.400(2) . ?
O3 O4 0.784(17) . ?
O4 O6 1.825(15) . ?
O5 O6 0.802(17) . ?
Cl2 O11 1.3989(15) . ?
Cl2 O10 1.397(2) . ?
Cl2 O7 1.4051(17) . ?
Cl2 O8 1.422(3) . ?
Cl2 O9 1.382(7) . ?
Cl2 O12 1.401(2) . ?
O9 O10 0.766(16) . ?
O10 O11 1.874(16) . ?
O11 O12 0.73(2) . ?
N1 C1 1.464(4) . ?
N1 C4 1.470(4) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C3 1.428(4) . ?
N2 C2 1.440(4) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
C1 C2 1.514(4) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.515(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N3 C8 1.476(4) . ?
N3 C5 1.490(4) . ?
N3 H3C 0.9000 . ?
N3 H3D 0.9000 . ?
N4 C6 1.451(4) . ?
N4 C7 1.467(4) . ?
N4 H4C 0.9000 . ?
N4 H4D 0.9000 . ?
C5 C6 1.503(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.505(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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
O6 Cl1 O4 81.6(8) . . ?
O6 Cl1 O3 114.0(8) . . ?
O4 Cl1 O3 32.6(7) . . ?
O6 Cl1 O1 110.3(8) . . ?
O4 Cl1 O1 114.6(6) . . ?
O3 Cl1 O1 103.6(7) . . ?
O6 Cl1 O2 120.4(8) . . ?
O4 Cl1 O2 118.7(6) . . ?
O3 Cl1 O2 97.6(5) . . ?
O1 Cl1 O2 109.1(2) . . ?
O6 Cl1 O5 33.3(7) . . ?
O4 Cl1 O5 113.4(8) . . ?
O3 Cl1 O5 144.2(7) . . ?
O1 Cl1 O5 103.7(6) . . ?
O2 Cl1 O5 94.8(4) . . ?
O4 O3 Cl1 73.7(4) . . ?
O3 O4 Cl1 73.8(4) . . ?
O3 O4 O6 122.8(5) . . ?
Cl1 O4 O6 49.2(4) . . ?
O6 O5 Cl1 73.1(4) . . ?
O5 O6 Cl1 73.6(4) . . ?
O5 O6 O4 120.6(8) . . ?
Cl1 O6 O4 49.2(4) . . ?
O11 Cl2 O10 84.2(9) . . ?
O11 Cl2 O7 108.1(8) . . ?
O10 Cl2 O7 114.3(6) . . ?
O11 Cl2 O8 119.8(8) . . ?
O10 Cl2 O8 120.3(7) . . ?
O7 Cl2 O8 108.3(2) . . ?
O11 Cl2 O9 115.4(8) . . ?
O10 Cl2 O9 32.0(7) . . ?
O7 Cl2 O9 108.1(6) . . ?
O8 Cl2 O9 96.4(4) . . ?
O11 Cl2 O12 30.2(9) . . ?
O10 Cl2 O12 109.5(8) . . ?
O7 Cl2 O12 109.9(5) . . ?
O8 Cl2 O12 92.1(4) . . ?
O9 Cl2 O12 136.0(7) . . ?
O10 O9 Cl2 75.1(8) . . ?
O9 O10 Cl2 72.9(5) . . ?
O9 O10 O11 119.7(9) . . ?
Cl2 O10 O11 48.0(5) . . ?
O12 O11 Cl2 75.1(5) . . ?
O12 O11 O10 115.7(12) . . ?
Cl2 O11 O10 47.9(4) . . ?
O11 O12 Cl2 74.7(5) . . ?
C1 N1 C4 112.7(3) . . ?
C1 N1 H1A 109.1 . . ?
C4 N1 H1A 109.1 . . ?
C1 N1 H1B 109.1 . . ?
C4 N1 H1B 109.1 . . ?
H1A N1 H1B 107.8 . . ?
C3 N2 C2 112.4(3) . . ?
C3 N2 H2A 109.1 . . ?
C2 N2 H2A 109.1 . . ?
C3 N2 H2B 109.1 . . ?
C2 N2 H2B 109.1 . . ?
H2A N2 H2B 107.9 . . ?
N1 C1 C2 111.6(3) . . ?
N1 C1 H1C 109.3 . . ?
C2 C1 H1C 109.3 . . ?
N1 C1 H1D 109.3 . . ?
C2 C1 H1D 109.3 . . ?
H1C C1 H1D 108.0 . . ?
N2 C2 C1 113.7(3) . . ?
N2 C2 H2C 108.8 . . ?
C1 C2 H2C 108.8 . . ?
N2 C2 H2D 108.8 . . ?
C1 C2 H2D 108.8 . . ?
H2C C2 H2D 107.7 . . ?
N2 C3 C4 113.9(3) . . ?
N2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
N2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N1 C4 C3 111.5(3) . . ?
N1 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C8 N3 C5 112.1(3) . . ?
C8 N3 H3C 109.2 . . ?
C5 N3 H3C 109.2 . . ?
C8 N3 H3D 109.2 . . ?
C5 N3 H3D 109.2 . . ?
H3C N3 H3D 107.9 . . ?
C6 N4 C7 110.6(3) . . ?
C6 N4 H4C 109.5 . . ?
C7 N4 H4C 109.5 . . ?
C6 N4 H4D 109.5 . . ?
C7 N4 H4D 109.5 . . ?
H4C N4 H4D 108.1 . . ?
N3 C5 C6 109.8(2) . . ?
N3 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N3 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N4 C6 C5 110.5(3) . . ?
N4 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N4 C7 C8 109.6(2) . . ?
N4 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N4 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
N3 C8 C7 110.3(3) . . ?
N3 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N3 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?

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
N1 H1A N4 0.90 2.05 2.922(4) 163.7 1_545
N1 H1B O2 0.90 2.08 2.961(4) 166.5 1_545
N1 H1B O3 0.90 2.55 3.254(10) 135.8 1_545
N2 H2A O8 0.90 2.26 3.145(5) 168.9 .
N2 H2B N3 0.90 2.04 2.899(4) 159.1 1_455
N3 H3C N2 0.90 2.01 2.899(4) 171.5 1_655
N3 H3D O8 0.90 2.31 3.005(4) 133.6 2_666
N3 H3D O12 0.90 2.33 3.135(9) 149.3 2_666
N4 H4C O2 0.90 2.44 3.152(4) 135.9 2_677
N4 H4C O5 0.90 2.50 3.341(11) 154.8 2_677
N4 H4D N1 0.90 2.06 2.922(4) 159.0 1_565

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_426K
_database_code_depnum_ccdc_archive 'CCDC 1019425'
_audit_update_record             
;
2014-08-14 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H44 Cl4 N8 O16'
_chemical_formula_weight         746.39

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/m

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

_cell_length_a                   13.047(8)
_cell_length_b                   9.700(3)
_cell_length_c                   8.348(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.31(9)
_cell_angle_gamma                90.00
_cell_volume                     817.5(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    426(1)
_cell_measurement_reflns_used    819
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.67

_exptl_crystal_description       transparent
_exptl_crystal_colour            colourles
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_min  0.99616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      426(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4145
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.67
_reflns_number_total             819
_reflns_number_gt                491
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1570P)²+0.0000P] where P=(Fo²+2Fc²)/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         819
_refine_ls_number_parameters     79
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.2163
_refine_ls_wR_factor_gt          0.1977
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.959
_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 0.26726(15) 0.5000 0.2301(2) 0.0808(7) Uani 1 2 d SD . .
O1 O 0.1285(2) 0.5000 0.0952(13) 0.213(3) Uani 1 2 d SD . .
O21 O 0.3640(14) 0.5841(17) 0.257(3) 0.267(10) Uani 0.50 1 d PD . .
O22 O 0.2839(11) 0.6135(9) 0.1454(19) 0.131(3) Uani 0.50 1 d PD . .
O31 O 0.316(5) 0.527(6) 0.432(4) 0.174(19) Uani 0.25 1 d PD . .
O32 O 0.276(4) 0.4084(16) 0.368(3) 0.122(8) Uani 0.25 1 d PD . .
N1 N 0.0963(5) 0.5000 0.4748(8) 0.0871(15) Uani 1 2 d S . .
H1A H 0.1199 0.5000 0.3942 0.105 Uiso 1 2 calc SPR . .
H1B H 0.1707 0.5000 0.6079 0.105 Uiso 0.5 2 calc SPR . .
C1 C 0.0196(5) 0.3776(4) 0.4337(7) 0.0875(13) Uani 1 1 d . . .
H2A H 0.0718 0.2961 0.4622 0.105 Uiso 1 1 calc R . .
H2B H -0.0589 0.3756 0.2890 0.105 Uiso 1 1 calc R . .
N2 N 0.3593(4) 0.5000 0.8748(7) 0.0823(14) Uani 1 2 d S . .
H3A H 0.2791 0.5000 0.7484 0.099 Uiso 0.5 2 calc SPR . .
H4B H 0.3474 0.5000 0.9699 0.099 Uiso 1 2 calc SPR . .
C2 C 0.4308(5) 0.6203(4) 0.8991(7) 0.1087(16) Uani 1 1 d . . .
H5A H 0.3846 0.7014 0.8919 0.130 Uiso 1 1 calc R . .
H6B H 0.4341 0.6252 0.7863 0.130 Uiso 1 1 calc R . .


_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 O21 1.397(2) . ?
Cl1 O31 1.400(3) . ?
Cl1 O22 1.398(2) . ?
Cl1 O1 1.401(3) . ?
Cl1 O32 1.400(2) . ?
N1 C1 1.447(5) . ?
N1 C1 1.447(5) 6_565 ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C1 C1 1.484(8) 2_556 ?
C1 H2A 0.9700 . ?
C1 H2B 0.9700 . ?
N2 C2 1.426(6) . ?
N2 C2 1.426(6) 6_565 ?
N2 H3A 0.9000 . ?
N2 H4B 0.9000 . ?
C2 C2 1.498(10) 2_657 ?
C2 H5A 0.9700 . ?
C2 H6B 0.9700 . ?

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



O21 Cl1 O31 104(3) 6_565 . ?
O21 Cl1 O31 104(3) . 6_565 ?
O31 Cl1 O22 131(3) . 6_565 ?
O31 Cl1 O22 111(2) 6_565 6_565 ?
O31 Cl1 O22 111(2) . . ?
O31 Cl1 O22 131(3) 6_565 . ?
O21 Cl1 O1 134.8(8) . . ?
O21 Cl1 O1 134.8(8) 6_565 . ?
O31 Cl1 O1 110(2) . . ?
O31 Cl1 O1 110(2) 6_565 . ?
O21 Cl1 O32 130.1(17) 6_565 6_565 ?
O22 Cl1 O32 163.3(11) 6_565 6_565 ?
O22 Cl1 O32 87.6(11) . 6_565 ?
O1 Cl1 O32 93.0(16) . 6_565 ?
O21 Cl1 O32 130.1(17) . . ?
O22 Cl1 O32 163.3(11) . . ?
C1 N1 C1 110.2(4) . 6_565 ?
C1 N1 H1A 109.6 . . ?
C1 N1 H1A 109.6 6_565 . ?
C1 N1 H1B 109.6 . . ?
C1 N1 H1B 109.6 6_565 . ?
H1A N1 H1B 108.1 . . ?
N1 C1 C1 109.7(3) . 2_556 ?
N1 C1 H2A 109.7 . . ?
C1 C1 H2A 109.7 2_556 . ?
N1 C1 H2B 109.7 . . ?
C1 C1 H2B 109.7 2_556 . ?
H2A C1 H2B 108.2 . . ?
C2 N2 C2 109.8(5) . 6_565 ?
C2 N2 H3A 109.7 . . ?
C2 N2 H3A 109.7 6_565 . ?
C2 N2 H4B 109.7 . . ?
C2 N2 H4B 109.7 6_565 . ?
H3A N2 H4B 108.2 . . ?
N2 C2 C2 112.0(4) . 2_657 ?
N2 C2 H5A 109.2 . . ?
C2 C2 H5A 109.2 2_657 . ?
N2 C2 H6B 109.2 . . ?
C2 C2 H6B 109.2 2_657 . ?
H5A C2 H6B 107.9 . . ?

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
N2 H3A N1 0.90 2.00 2.899(9) 176.9 .
N1 H1B N2 0.90 2.02 2.899(9) 165.9 .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.080
