# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1032979'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.20 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H Cl4 O4, C8 H2 Cl4 O4, C12 H9 N2, C H4 O'
_chemical_formula_sum            'C29 H16 Cl8 N2 O9'
_chemical_formula_weight         820.04
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.1486(4)
_cell_length_b                   8.7692(2)
_cell_length_c                   22.0638(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.758(2)
_cell_angle_gamma                90.00
_cell_volume                     3261.26(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17101
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.42
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5291
_reflns_number_total             6740
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         6740
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+1.3431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0991
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N2-H2
 0.82 with sigma of 0.01
 O9-H9
 0.85 with sigma of 0.02
 O1-H1
 0.85 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C56(H56)
3.b Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.14842(3) 0.07651(7) 0.29370(3) 0.04532(16) Uani 1 d . . .
Cl2 Cl -0.17687(4) 0.90522(8) 0.23505(3) 0.05613(19) Uani 1 d . . .
Cl3 Cl -0.03182(4) 0.92161(8) 0.19304(3) 0.04936(17) Uani 1 d . . .
Cl4 Cl 0.02048(4) 0.29973(9) 0.45923(3) 0.0589(2) Uani 1 d . . .
Cl5 Cl 0.00705(4) 0.10244(8) 0.33904(3) 0.0575(2) Uani 1 d . . .
Cl6 Cl -0.32440(4) 0.71361(9) 0.15401(4) 0.05733(19) Uani 1 d . . .
Cl7 Cl 0.17496(4) 0.47980(9) 0.53240(3) 0.0577(2) Uani 1 d . . .
Cl8 Cl -0.32933(4) 0.54712(9) 0.02866(4) 0.0584(2) Uani 1 d . . .
O1 O 0.01968(9) 0.6877(2) 0.11368(8) 0.0394(4) Uani 1 d . . D
O7 O 0.36183(8) 0.20893(17) 0.41489(7) 0.0355(4) Uani 1 d . . .
C3 C -0.11384(12) 0.7373(2) 0.09303(10) 0.0267(4) Uani 1 d . . .
C4 C 0.22775(12) 0.2661(2) 0.39325(10) 0.0275(4) Uani 1 d . . .
C5 C 0.29716(12) 0.2586(2) 0.37087(10) 0.0307(5) Uani 1 d . . .
C6 C 0.09924(12) 0.2872(3) 0.43416(11) 0.0335(5) Uani 1 d . . .
C7 C -0.24424(13) 0.7239(2) 0.13054(11) 0.0335(5) Uani 1 d . . .
O2 O -0.05000(9) 0.80021(18) 0.01982(7) 0.0389(4) Uani 1 d . . .
C9 C -0.04339(12) 0.7449(2) 0.07226(10) 0.0271(4) Uani 1 d . . .
C10 C 0.16953(13) 0.3635(2) 0.46759(10) 0.0324(5) Uani 1 d . . .
C11 C -0.17793(13) 0.8084(2) 0.16706(10) 0.0332(5) Uani 1 d . . .
O5 O 0.34783(10) 0.40313(19) 0.54347(7) 0.0446(4) Uani 1 d . . .
C13 C -0.18127(12) 0.6562(2) 0.05540(10) 0.0283(4) Uani 1 d . . .
C14 C 0.09319(12) 0.1993(2) 0.38027(10) 0.0317(5) Uani 1 d . . .
C15 C -0.18299(13) 0.5709(2) -0.00435(11) 0.0327(5) Uani 1 d . . .
C16 C 0.23389(12) 0.3515(2) 0.44831(10) 0.0285(4) Uani 1 d . . .
C17 C -0.24615(12) 0.6504(2) 0.07430(11) 0.0329(5) Uani 1 d . . .
C18 C 0.15693(12) 0.1892(2) 0.35998(10) 0.0293(5) Uani 1 d . . .
O8 O 0.28997(10) 0.2994(2) 0.31691(8) 0.0537(5) Uani 1 d . . .
C20 C -0.11286(12) 0.8147(2) 0.14841(10) 0.0296(5) Uani 1 d . . .
C21 C 0.31042(13) 0.4323(2) 0.48731(10) 0.0319(5) Uani 1 d . . .
O3 O -0.12842(10) 0.46454(19) 0.01150(7) 0.0437(4) Uani 1 d . . .
H3 H -0.1334 0.4128 -0.0207 0.066 Uiso 1 calc . . GR
O4 O -0.22881(11) 0.5974(2) -0.05816(8) 0.0531(5) Uani 1 d . . .
O6 O 0.32855(10) 0.53617(18) 0.45297(7) 0.0419(4) Uani 1 d . . .
H6 H 0.3694 0.5796 0.4758 0.063 Uiso 1 calc . . GR
N2 N -0.00281(13) 0.3771(2) 0.18060(10) 0.0442(5) Uani 1 d . . D
O9 O -0.16077(14) 0.3137(3) 0.13370(12) 0.0813(7) Uani 1 d . . D
C27 C 0.04713(15) 0.4634(3) 0.22977(11) 0.0407(6) Uani 1 d . . .
C28 C 0.12481(15) 0.4822(3) 0.23401(12) 0.0449(6) Uani 1 d . . .
C29 C 0.01798(18) 0.5330(3) 0.27560(12) 0.0482(7) Uani 1 d . . .
N1 N -0.05848(17) 0.5075(3) 0.26792(12) 0.0610(6) Uani 1 d . . .
C31 C 0.01970(17) 0.3089(3) 0.13660(12) 0.0501(6) Uani 1 d . . .
H31 H -0.0165 0.2510 0.1036 0.060 Uiso 1 calc . . R
C32 C 0.17679(19) 0.5783(3) 0.28567(15) 0.0649(9) Uani 1 d . . .
H32 H 0.2288 0.5951 0.2891 0.078 Uiso 1 calc . . R
C33 C 0.14861(17) 0.4098(3) 0.18835(14) 0.0553(7) Uani 1 d . . .
H33 H 0.2007 0.4201 0.1909 0.066 Uiso 1 calc . . R
C34 C 0.0704(2) 0.6226(3) 0.32509(13) 0.0592(8) Uani 1 d . . .
C35 C 0.09659(17) 0.3236(3) 0.13981(14) 0.0559(7) Uani 1 d . . .
H35 H 0.1128 0.2755 0.1093 0.067 Uiso 1 calc . . R
C36 C 0.1497(2) 0.6433(3) 0.32866(15) 0.0732(11) Uani 1 d . . .
H36 H 0.1840 0.7038 0.3618 0.088 Uiso 1 calc . . R
C37 C -0.0833(3) 0.5719(4) 0.31137(17) 0.0799(11) Uani 1 d . . .
H37 H -0.1355 0.5554 0.3074 0.096 Uiso 1 calc . . R
C38 C 0.0399(3) 0.6878(4) 0.36977(15) 0.0820(12) Uani 1 d . . .
H38 H 0.0721 0.7480 0.4041 0.098 Uiso 1 calc . . R
C43 C -0.2135(2) 0.2965(4) 0.16618(18) 0.0837(11) Uani 1 d . . .
H43A H -0.2670 0.3010 0.1351 0.126 Uiso 1 calc . . GR
H43B H -0.2050 0.3770 0.1976 0.126 Uiso 1 calc . . GR
H43C H -0.2045 0.1998 0.1881 0.126 Uiso 1 calc . . GR
C56 C -0.0360(3) 0.6619(4) 0.36214(18) 0.0907(13) Uani 1 d . . .
H56 H -0.0566 0.7047 0.3911 0.109 Uiso 1 calc . . R
H2 H -0.0504(8) 0.369(3) 0.1790(13) 0.049(8) Uiso 1 d . . D
H9 H -0.155(4) 0.231(5) 0.113(3) 0.26(4) Uiso 1 d . . D
H1 H 0.0613(12) 0.701(4) 0.1041(15) 0.081(11) Uiso 1 d . . D


_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 C18 1.724(2) . ?
Cl2 C11 1.718(2) . ?
Cl3 C20 1.714(2) . ?
Cl4 C6 1.717(2) . ?
Cl5 C14 1.714(2) . ?
Cl6 C7 1.718(2) . ?
Cl7 C10 1.729(2) . ?
Cl8 C17 1.728(2) . ?
O1 C9 1.273(2) . ?
O7 C5 1.291(2) . ?
C3 C9 1.511(3) . ?
C3 C13 1.393(3) . ?
C3 C20 1.392(3) . ?
C4 C5 1.515(3) . ?
C4 C16 1.396(3) . ?
C4 C18 1.395(3) . ?
C5 O8 1.203(3) . ?
C6 C10 1.386(3) . ?
C6 C14 1.387(3) . ?
C7 C11 1.388(3) . ?
C7 C17 1.388(3) . ?
O2 C9 1.219(2) . ?
C10 C16 1.387(3) . ?
C11 C20 1.388(3) . ?
O5 C21 1.199(3) . ?
C13 C15 1.506(3) . ?
C13 C17 1.388(3) . ?
C14 C18 1.389(3) . ?
C15 O3 1.310(3) . ?
C15 O4 1.193(3) . ?
C16 C21 1.512(3) . ?
C21 O6 1.303(3) . ?
N2 C27 1.357(3) . ?
N2 C31 1.327(3) . ?
O9 C43 1.400(4) . ?
C27 C28 1.388(4) . ?
C27 C29 1.439(4) . ?
C28 C32 1.450(4) . ?
C28 C33 1.388(4) . ?
C29 N1 1.353(4) . ?
C29 C34 1.394(4) . ?
N1 C37 1.327(4) . ?
C31 C35 1.377(4) . ?
C32 C36 1.346(5) . ?
C33 C35 1.364(4) . ?
C34 C36 1.424(5) . ?
C34 C38 1.418(5) . ?
C37 C56 1.379(5) . ?
C38 C56 1.343(6) . ?

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
C13 C3 C9 119.81(18) . . ?
C20 C3 C9 120.53(18) . . ?
C20 C3 C13 119.64(19) . . ?
C16 C4 C5 119.92(18) . . ?
C18 C4 C5 121.52(18) . . ?
C18 C4 C16 118.56(19) . . ?
O7 C5 C4 113.79(18) . . ?
O8 C5 O7 125.4(2) . . ?
O8 C5 C4 120.76(19) . . ?
C10 C6 Cl4 120.66(17) . . ?
C10 C6 C14 119.3(2) . . ?
C14 C6 Cl4 120.06(16) . . ?
C11 C7 Cl6 120.14(17) . . ?
C17 C7 Cl6 120.12(17) . . ?
C17 C7 C11 119.7(2) . . ?
O1 C9 C3 113.68(18) . . ?
O2 C9 O1 125.7(2) . . ?
O2 C9 C3 120.57(17) . . ?
C6 C10 Cl7 118.92(17) . . ?
C6 C10 C16 120.90(19) . . ?
C16 C10 Cl7 120.15(16) . . ?
C7 C11 Cl2 119.82(17) . . ?
C7 C11 C20 119.92(19) . . ?
C20 C11 Cl2 120.26(17) . . ?
C3 C13 C15 120.26(19) . . ?
C17 C13 C3 119.71(19) . . ?
C17 C13 C15 120.00(18) . . ?
C6 C14 Cl5 119.81(17) . . ?
C6 C14 C18 120.04(18) . . ?
C18 C14 Cl5 120.15(16) . . ?
O3 C15 C13 110.58(18) . . ?
O4 C15 C13 123.7(2) . . ?
O4 C15 O3 125.7(2) . . ?
C4 C16 C21 120.47(19) . . ?
C10 C16 C4 120.20(18) . . ?
C10 C16 C21 119.33(18) . . ?
C7 C17 Cl8 119.44(17) . . ?
C7 C17 C13 120.58(19) . . ?
C13 C17 Cl8 119.96(17) . . ?
C4 C18 Cl1 119.92(16) . . ?
C14 C18 Cl1 119.09(15) . . ?
C14 C18 C4 120.97(19) . . ?
C3 C20 Cl3 119.99(16) . . ?
C11 C20 Cl3 119.62(16) . . ?
C11 C20 C3 120.37(19) . . ?
O5 C21 C16 122.5(2) . . ?
O5 C21 O6 125.6(2) . . ?
O6 C21 C16 111.94(17) . . ?
C31 N2 C27 122.7(2) . . ?
N2 C27 C28 118.7(2) . . ?
N2 C27 C29 119.2(2) . . ?
C28 C27 C29 122.1(2) . . ?
C27 C28 C32 118.1(3) . . ?
C27 C28 C33 118.6(2) . . ?
C33 C28 C32 123.3(3) . . ?
N1 C29 C27 118.0(2) . . ?
N1 C29 C34 124.2(3) . . ?
C34 C29 C27 117.9(3) . . ?
C37 N1 C29 116.5(3) . . ?
N2 C31 C35 120.1(3) . . ?
C36 C32 C28 119.9(3) . . ?
C35 C33 C28 120.8(3) . . ?
C29 C34 C36 119.8(3) . . ?
C29 C34 C38 116.3(3) . . ?
C38 C34 C36 123.9(3) . . ?
C33 C35 C31 119.1(3) . . ?
C32 C36 C34 122.2(3) . . ?
N1 C37 C56 123.7(4) . . ?
C56 C38 C34 119.4(3) . . ?
C38 C56 C37 120.0(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1032980'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.20 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '(C8 H Cl4 O4),(C2 H5 N4)'
_chemical_formula_sum            'C10 H6 Cl4 N4 O4'
_chemical_formula_weight         387.99
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 'x, -y-1/2, z-1/2'
8 '-x-1/2, y-1/2, z'

_cell_length_a                   9.4206(3)
_cell_length_b                   12.0251(3)
_cell_length_c                   24.0488(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2724.34(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8878
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.75
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2448
_reflns_number_total             2950
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0246P)²+1.3405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0705
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3A), N4(H4), C17(H17)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.09841(6) 0.09932(4) 0.33185(2) 0.03394(14) Uani 1 d . . .
Cl2 Cl -0.16960(6) -0.12574(4) 0.17012(2) 0.03715(14) Uani 1 d . . .
Cl3 Cl -0.33902(5) -0.25775(4) 0.25874(2) 0.03202(13) Uani 1 d . . .
Cl4 Cl 0.05026(6) 0.05212(4) 0.20661(2) 0.03354(14) Uani 1 d . . .
O1 O 0.00045(15) -0.11661(11) 0.43952(6) 0.0335(3) Uani 1 d . . .
O2 O -0.10407(15) 0.04779(10) 0.43441(6) 0.0302(3) Uani 1 d . . .
C3 C -0.1405(2) -0.10227(15) 0.23951(8) 0.0240(4) Uani 1 d . . .
N3 N 0.27850(18) -0.43803(13) 0.46691(7) 0.0320(4) Uani 1 d . . .
H3A H 0.3564 -0.4669 0.4787 0.038 Uiso 1 calc . . R
C5 C -0.09244(19) -0.06315(14) 0.35236(8) 0.0217(4) Uani 1 d . . .
C6 C -0.0432(2) -0.02176(14) 0.25586(8) 0.0236(4) Uani 1 d . . .
C7 C -0.02094(19) -0.00155(14) 0.31191(8) 0.0231(4) Uani 1 d . . .
C8 C -0.06354(19) -0.04226(15) 0.41339(8) 0.0232(4) Uani 1 d . . .
O3 O -0.23681(16) -0.31893(10) 0.37757(6) 0.0339(3) Uani 1 d . . .
H3 H -0.2948 -0.3535 0.3962 0.051 Uiso 1 calc . . GR
C10 C -0.26514(19) -0.21190(15) 0.38028(8) 0.0237(4) Uani 1 d . . .
C11 C -0.21165(19) -0.16391(14) 0.27976(8) 0.0224(4) Uani 1 d . . .
O4 O -0.34143(15) -0.16828(12) 0.41380(6) 0.0380(4) Uani 1 d . . .
N2 N 0.1579(2) -0.49803(15) 0.45566(8) 0.0383(4) Uani 1 d . . .
C14 C -0.18665(19) -0.14633(14) 0.33613(8) 0.0217(4) Uani 1 d . . .
N4 N 0.1260(2) -0.31959(15) 0.43973(8) 0.0389(5) Uani 1 d . . .
H4 H 0.0843 -0.2588 0.4303 0.047 Uiso 1 calc . . R
C16 C 0.2608(2) -0.33049(16) 0.45747(9) 0.0320(5) Uani 1 d . . .
C17 C 0.0685(2) -0.42352(19) 0.43956(10) 0.0426(6) Uani 1 d . . .
H17 H -0.0245 -0.4389 0.4290 0.051 Uiso 1 calc . . R
N1 N 0.3566(2) -0.25153(16) 0.46328(10) 0.0514(6) Uani 1 d . . .
H1A H 0.4409 -0.2679 0.4743 0.062 Uiso 1 calc . . R
H1B H 0.3348 -0.1836 0.4561 0.062 Uiso 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 C7 1.7220(19) . ?
Cl2 C3 1.714(2) . ?
Cl3 C11 1.7230(18) . ?
Cl4 C6 1.7228(19) . ?
O1 C8 1.248(2) . ?
O2 C8 1.254(2) . ?
C3 C6 1.390(3) . ?
C3 C11 1.391(3) . ?
N3 N2 1.373(2) . ?
N3 C16 1.324(2) . ?
C5 C7 1.396(3) . ?
C5 C8 1.514(3) . ?
C5 C14 1.393(3) . ?
C6 C7 1.386(3) . ?
O3 C10 1.316(2) . ?
C10 O4 1.201(2) . ?
C10 C14 1.515(3) . ?
C11 C14 1.392(3) . ?
N2 C17 1.289(3) . ?
N4 C16 1.346(3) . ?
N4 C17 1.362(3) . ?
C16 N1 1.317(3) . ?

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
C6 C3 Cl2 119.69(15) . . ?
C6 C3 C11 119.46(18) . . ?
C11 C3 Cl2 120.85(15) . . ?
C16 N3 N2 112.05(17) . . ?
C7 C5 C8 120.05(16) . . ?
C14 C5 C7 119.55(18) . . ?
C14 C5 C8 120.36(16) . . ?
C3 C6 Cl4 120.12(15) . . ?
C7 C6 Cl4 120.06(14) . . ?
C7 C6 C3 119.82(17) . . ?
C5 C7 Cl1 119.66(15) . . ?
C6 C7 Cl1 119.56(14) . . ?
C6 C7 C5 120.77(17) . . ?
O1 C8 O2 124.24(18) . . ?
O1 C8 C5 117.13(16) . . ?
O2 C8 C5 118.63(16) . . ?
O3 C10 C14 112.05(16) . . ?
O4 C10 O3 125.58(18) . . ?
O4 C10 C14 122.36(16) . . ?
C3 C11 Cl3 118.69(15) . . ?
C3 C11 C14 121.01(17) . . ?
C14 C11 Cl3 120.20(14) . . ?
C17 N2 N3 103.56(17) . . ?
C5 C14 C10 119.23(17) . . ?
C11 C14 C5 119.32(17) . . ?
C11 C14 C10 121.38(16) . . ?
C16 N4 C17 106.68(17) . . ?
N3 C16 N4 105.56(19) . . ?
N1 C16 N3 126.9(2) . . ?
N1 C16 N4 127.56(19) . . ?
N2 C17 N4 112.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound3
_database_code_depnum_ccdc_archive 'CCDC 1032981'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 Cl8 N4 O8'
_chemical_formula_sum            'C32 H22 Cl8 N4 O8'
_chemical_formula_weight         874.14

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'
Cl Cl 0.1484 0.1585 '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'

_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                   8.5055(6)
_cell_length_b                   9.8663(7)
_cell_length_c                   11.0901(7)
_cell_angle_alpha                88.1770(10)
_cell_angle_beta                 73.7680(10)
_cell_angle_gamma                87.1080(10)
_cell_volume                     892.27(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             442
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4639
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3107
_reflns_number_gt                2808
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0906P)²+2.0005P] 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         3107
_refine_ls_number_parameters     242
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1736
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.044
_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
Cl4 Cl 0.19975(11) -0.36321(11) 0.13914(10) 0.0450(3) Uani 1 1 d . . .
Cl1 Cl 0.85105(12) -0.56451(11) 0.24716(11) 0.0486(3) Uani 1 1 d . . .
Cl3 Cl 0.52821(13) -0.24508(11) -0.01709(10) 0.0496(3) Uani 1 1 d . . .
Cl2 Cl 0.85358(12) -0.33833(12) 0.04252(11) 0.0491(3) Uani 1 1 d . . .
O4 O 0.1357(4) -0.4662(3) 0.4274(3) 0.0458(7) Uani 1 1 d . . .
O1 O 0.5027(5) -0.6254(3) 0.4970(3) 0.0548(9) Uani 1 1 d . . .
O3 O 0.1774(4) -0.6736(3) 0.3528(3) 0.0545(8) Uani 1 1 d . . .
O2 O 0.5529(5) -0.7884(3) 0.3577(3) 0.0583(9) Uani 1 1 d . . .
C9 C 0.5252(4) -0.5616(3) 0.2855(3) 0.0275(7) Uani 1 1 d . . .
C10 C 0.3773(4) -0.5109(3) 0.2674(3) 0.0270(7) Uani 1 1 d . . .
C11 C 0.6732(4) -0.4078(4) 0.1244(3) 0.0311(8) Uani 1 1 d . . .
C12 C 0.2172(4) -0.5579(4) 0.3537(3) 0.0306(8) Uani 1 1 d . . .
C13 C 0.0026(6) 0.0423(4) 0.1181(4) 0.0424(9) Uani 1 1 d . . .
C14 C 0.6711(4) -0.5089(4) 0.2155(3) 0.0312(8) Uani 1 1 d . . .
C15 C 0.3800(4) -0.4148(4) 0.1720(3) 0.0296(7) Uani 1 1 d . . .
C16 C 0.5264(4) -0.3628(4) 0.1007(3) 0.0310(8) Uani 1 1 d . . .
C17 C 0.5271(5) -0.6700(4) 0.3865(4) 0.0348(8) Uani 1 1 d . . .
C18 C 0.1394(6) -0.0243(4) 0.0393(5) 0.0484(10) Uani 1 1 d . . .
H18 H 0.2338 -0.0401 0.0652 0.080 Uiso 1 1 calc . . .
N1 N 0.0770(7) -0.0086(4) 0.3165(4) 0.0624(12) Uani 1 1 d . . .
C20 C -0.1352(6) 0.0672(4) 0.0775(4) 0.0480(10) Uani 1 1 d . . .
H20 H -0.2263 0.1131 0.1290 0.080 Uiso 1 1 calc . . .
C21 C 0.0070(7) 0.0927(4) 0.2444(5) 0.0564(12) Uani 1 1 d . . .
H21A H 0.0711 0.1731 0.2316 0.068 Uiso 1 1 calc R . .
H21B H -0.1037 0.1185 0.2927 0.068 Uiso 1 1 calc R . .
N2 N 0.1277(16) -0.1859(6) 0.4143(6) 0.168(6) Uani 1.00(3) 1 d U A 1
H2 H 0.1150 -0.2631 0.4532 0.080 Uiso 1 1 calc . B 1
C23 C -0.1480(18) -0.1676(12) 0.3635(7) 0.186(7) Uani 1 1 d . A 1
H23A H -0.2282 -0.0944 0.3891 0.278 Uiso 1 1 calc R A 1
H23B H -0.1775 -0.2436 0.4202 0.278 Uiso 1 1 calc R A 1
H23C H -0.1440 -0.1938 0.2800 0.278 Uiso 1 1 calc R A 1
C24 C 0.0147(14) -0.1229(6) 0.3652(5) 0.116(4) Uani 1 1 d . A 1
C25 C 0.2315(10) -0.0032(7) 0.3353(6) 0.086(2) Uani 1 1 d . A 1
H25 H 0.3015 0.0680 0.3090 0.103 Uiso 1 1 calc R A 1
C26 C 0.2644(18) -0.1127(8) 0.3952(9) 0.139(5) Uani 1 1 d . A 1
H26 H 0.3590 -0.1353 0.4191 0.167 Uiso 1 1 calc R A 1
H4 H 0.055(11) -0.487(10) 0.470(9) 0.04(3) Uiso 0.50 1 d P . .
H1 H 0.5000 -0.5000 0.5000 0.08(2) Uiso 1 2 d S . .


_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
Cl4 C15 1.722(3) . ?
Cl1 C14 1.724(4) . ?
Cl3 C16 1.717(4) . ?
Cl2 C11 1.713(4) . ?
O4 C12 1.279(5) . ?
O1 C17 1.273(5) . ?
O3 C12 1.208(5) . ?
O2 C17 1.214(5) . ?
C9 C14 1.384(5) . ?
C9 C10 1.394(5) . ?
C9 C17 1.527(5) . ?
C10 C15 1.395(5) . ?
C10 C12 1.514(5) . ?
C11 C14 1.394(5) . ?
C11 C16 1.394(5) . ?
C13 C20 1.377(6) . ?
C13 C18 1.393(6) . ?
C13 C21 1.512(6) . ?
C15 C16 1.388(5) . ?
C18 C20 1.386(7) 2 ?
N1 C24 1.306(7) . ?
N1 C25 1.391(9) . ?
N1 C21 1.466(6) . ?
C20 C18 1.386(7) 2 ?
N2 C24 1.349(14) . ?
N2 C26 1.361(16) . ?
C23 C24 1.479(14) . ?
C25 C26 1.310(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
C14 C9 C10 119.8(3) . . ?
C14 C9 C17 119.6(3) . . ?
C10 C9 C17 120.5(3) . . ?
C9 C10 C15 119.1(3) . . ?
C9 C10 C12 119.6(3) . . ?
C15 C10 C12 121.2(3) . . ?
C14 C11 C16 119.3(3) . . ?
C14 C11 Cl2 120.6(3) . . ?
C16 C11 Cl2 120.0(3) . . ?
O3 C12 O4 125.1(3) . . ?
O3 C12 C10 121.1(3) . . ?
O4 C12 C10 113.7(3) . . ?
C20 C13 C18 119.3(4) . . ?
C20 C13 C21 120.0(4) . . ?
C18 C13 C21 120.7(4) . . ?
C9 C14 C11 121.0(3) . . ?
C9 C14 Cl1 119.0(3) . . ?
C11 C14 Cl1 120.0(3) . . ?
C16 C15 C10 121.0(3) . . ?
C16 C15 Cl4 119.4(3) . . ?
C10 C15 Cl4 119.5(3) . . ?
C15 C16 C11 119.5(3) . . ?
C15 C16 Cl3 120.6(3) . . ?
C11 C16 Cl3 119.9(3) . . ?
O2 C17 O1 125.2(4) . . ?
O2 C17 C9 119.7(4) . . ?
O1 C17 C9 115.1(3) . . ?
C20 C18 C13 120.2(4) 2 . ?
C24 N1 C25 108.0(6) . . ?
C24 N1 C21 127.4(6) . . ?
C25 N1 C21 124.5(5) . . ?
C13 C20 C18 120.5(4) . 2 ?
N1 C21 C13 113.1(4) . . ?
C24 N2 C26 112.0(6) . . ?
N1 C24 N2 105.9(8) . . ?
N1 C24 C23 124.7(9) . . ?
N2 C24 C23 129.5(7) . . ?
C26 C25 N1 110.2(9) . . ?
C25 C26 N2 103.9(9) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.512
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.095
####################################################################### 
# 
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 1032982'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.20 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H Cl4 O4, C4 H6 N3'
_chemical_formula_sum            'C12 H7 Cl4 N3 O4'
_chemical_formula_weight         399.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.614(3)
_cell_length_b                   11.255(2)
_cell_length_c                   10.900(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.969(3)
_cell_angle_gamma                90.00
_cell_volume                     1480.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9642
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.294
_cell_measurement_theta_min      2.475
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1676
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14714
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.69
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2324
_reflns_number_total             2590
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0960P)²+0.5287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1498
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C33(H33), C36(H36), C38(H38)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.00273(6) 0.32276(7) -0.05284(7) 0.0464(3) Uani 1 d . . .
Cl4 Cl 0.17471(6) -0.08568(7) 0.33613(8) 0.0495(3) Uani 1 d . . .
Cl5 Cl -0.16395(5) 0.15207(7) 0.01828(7) 0.0424(3) Uani 1 d . . .
Cl7 Cl -0.07718(6) -0.04875(7) 0.21763(7) 0.0450(3) Uani 1 d . . .
O1 O 0.3007(2) 0.3397(2) 0.1559(2) 0.0507(6) Uani 1 d . . .
O2 O 0.25272(17) 0.2650(2) -0.04148(18) 0.0448(5) Uani 1 d . . .
O3 O 0.37154(16) 0.10376(19) 0.37055(17) 0.0385(5) Uani 1 d . . .
H3 H 0.3276 0.1403 0.3990 0.058 Uiso 1 calc . . GR
O4 O 0.37748(16) 0.04171(18) 0.18151(18) 0.0397(5) Uani 1 d . . .
C5 C -0.0243(2) 0.1339(2) 0.0866(2) 0.0295(6) Uani 1 d . . .
C6 C 0.2026(2) 0.1031(2) 0.1958(2) 0.0263(5) Uani 1 d . . .
C9 C 0.1640(2) 0.1922(2) 0.1061(2) 0.0279(5) Uani 1 d . . .
C11 C 0.3255(2) 0.0802(2) 0.2499(2) 0.0286(5) Uani 1 d . . .
C14 C 0.0139(2) 0.0442(2) 0.1747(2) 0.0296(6) Uani 1 d . . .
C17 C 0.0510(2) 0.2083(2) 0.0533(2) 0.0296(6) Uani 1 d . . .
C22 C 0.2458(2) 0.2733(2) 0.0702(2) 0.0308(6) Uani 1 d . . .
C31 C 0.1276(2) 0.0290(2) 0.2296(2) 0.0291(5) Uani 1 d . . .
N1 N 0.6383(2) -0.0263(2) 0.0966(2) 0.0421(6) Uani 1 d . . .
H1A H 0.6278 -0.0239 0.0151 0.051 Uiso 1 calc . . R
H1B H 0.6607 -0.0909 0.1383 0.051 Uiso 1 calc . . R
N5 N 0.63623(19) 0.0616(2) 0.2858(2) 0.0366(5) Uani 1 d . . .
H5 H 0.6616 -0.0030 0.3259 0.044 Uiso 1 calc . . R
N6 N 0.5850(2) 0.1696(2) 0.0933(2) 0.0410(6) Uani 1 d . . .
C27 C 0.6200(2) 0.0685(2) 0.1574(2) 0.0321(6) Uani 1 d . . .
C33 C 0.6131(2) 0.1548(3) 0.3514(3) 0.0426(7) Uani 1 d . . .
H33 H 0.6235 0.1486 0.4392 0.051 Uiso 1 calc . . R
C36 C 0.5633(3) 0.2592(3) 0.1602(3) 0.0447(7) Uani 1 d . . .
H36 H 0.5382 0.3296 0.1165 0.054 Uiso 1 calc . . R
C38 C 0.5751(3) 0.2564(3) 0.2900(3) 0.0459(7) Uani 1 d . . .
H38 H 0.5575 0.3215 0.3328 0.055 Uiso 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 C17 1.720(3) . ?
Cl4 C31 1.721(3) . ?
Cl5 C5 1.713(3) . ?
Cl7 C14 1.716(2) . ?
O1 C22 1.239(3) . ?
O2 C22 1.249(3) . ?
O3 H3 0.8200 . ?
O3 C11 1.301(3) . ?
O4 C11 1.207(3) . ?
C5 C14 1.380(4) . ?
C5 C17 1.391(4) . ?
C6 C9 1.386(4) . ?
C6 C11 1.512(4) . ?
C6 C31 1.389(3) . ?
C9 C17 1.385(4) . ?
C9 C22 1.511(3) . ?
C14 C31 1.395(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C27 1.312(4) . ?
N5 H5 0.8600 . ?
N5 C27 1.356(3) . ?
N5 C33 1.349(4) . ?
N6 C27 1.341(4) . ?
N6 C36 1.319(4) . ?
C33 H33 0.9300 . ?
C33 C38 1.340(4) . ?
C36 H36 0.9300 . ?
C36 C38 1.380(4) . ?
C38 H38 0.9300 . ?

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
C11 O3 H3 109.5 . . ?
C14 C5 Cl5 119.69(19) . . ?
C14 C5 C17 119.8(2) . . ?
C17 C5 Cl5 120.6(2) . . ?
C9 C6 C11 120.4(2) . . ?
C9 C6 C31 119.7(2) . . ?
C31 C6 C11 119.7(2) . . ?
C6 C9 C22 119.6(2) . . ?
C17 C9 C6 119.6(2) . . ?
C17 C9 C22 120.7(2) . . ?
O3 C11 C6 117.6(2) . . ?
O4 C11 O3 122.4(2) . . ?
O4 C11 C6 120.0(2) . . ?
C5 C14 Cl7 120.71(19) . . ?
C5 C14 C31 119.6(2) . . ?
C31 C14 Cl7 119.7(2) . . ?
C5 C17 Cl1 119.46(19) . . ?
C9 C17 Cl1 119.8(2) . . ?
C9 C17 C5 120.8(2) . . ?
O1 C22 O2 126.7(2) . . ?
O1 C22 C9 116.3(2) . . ?
O2 C22 C9 117.0(2) . . ?
C6 C31 Cl4 120.10(19) . . ?
C6 C31 C14 120.5(2) . . ?
C14 C31 Cl4 119.36(19) . . ?
H1A N1 H1B 120.0 . . ?
C27 N1 H1A 120.0 . . ?
C27 N1 H1B 120.0 . . ?
C27 N5 H5 119.6 . . ?
C33 N5 H5 119.6 . . ?
C33 N5 C27 120.8(2) . . ?
C36 N6 C27 116.8(2) . . ?
N1 C27 N5 118.6(3) . . ?
N1 C27 N6 120.4(2) . . ?
N6 C27 N5 120.9(2) . . ?
N5 C33 H33 120.0 . . ?
C38 C33 N5 120.0(3) . . ?
C38 C33 H33 120.0 . . ?
N6 C36 H36 117.6 . . ?
N6 C36 C38 124.8(3) . . ?
C38 C36 H36 117.6 . . ?
C33 C38 C36 116.6(3) . . ?
C33 C38 H38 121.7 . . ?
C36 C38 H38 121.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 1032983'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.20 svn.r3092 for OlexSys, GUI svn.r4949)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H Cl4 O4, C H5 N'
_chemical_formula_sum            'C9 H6 Cl4 N O4'
_chemical_formula_weight         333.95
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.8502(17)
_cell_length_b                   5.5385(2)
_cell_length_c                   12.5520(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.115(6)
_cell_angle_gamma                90
_cell_volume                     2473.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9460
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.290
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2254
_reflns_number_total             2667
_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       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.041
_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)+(0.0403P)²+2.4684P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.13649(2) 0.40752(9) 0.41016(4) 0.03572(15) Uani 1 1 d . . . . .
Cl2 Cl 0.05199(2) 0.44130(12) 0.29979(5) 0.05482(19) Uani 1 1 d . . . . .
Cl3 Cl 0.07677(2) 1.15893(14) 0.03817(5) 0.0616(2) Uani 1 1 d . . . . .
Cl4 Cl 0.02157(2) 0.81576(18) 0.11391(7) 0.0853(3) Uani 1 1 d . . . . .
O1 O 0.19828(4) 0.7749(2) 0.43369(10) 0.0283(3) Uani 1 1 d . . . . .
O2 O 0.20971(4) 0.7791(2) 0.27013(10) 0.0308(3) Uani 1 1 d . . . . .
N1 N 0.26922(4) 1.0631(3) 0.40104(12) 0.0263(3) Uani 1 1 d . . . . .
H1A H 0.2821 1.1181 0.3551 0.032 Uiso 1 1 calc GR . . . .
H1B H 0.2521 0.9568 0.3660 0.032 Uiso 1 1 calc GR . . . .
H1C H 0.2849 0.9920 0.4585 0.032 Uiso 1 1 calc GR . . . .
O3 O 0.17468(4) 1.2622(3) 0.18882(12) 0.0398(4) Uani 1 1 d . . . . .
C6 C 0.15818(5) 1.0882(3) 0.14309(14) 0.0255(4) Uani 1 1 d . . . . .
C7 C 0.14585(5) 0.7734(3) 0.27536(14) 0.0230(4) Uani 1 1 d . . . . .
C8 C 0.18754(5) 0.7721(3) 0.32965(14) 0.0217(4) Uani 1 1 d . . . . .
O4 O 0.15971(4) 1.0058(3) 0.04653(11) 0.0389(4) Uani 1 1 d . . . . .
H4 H 0.1725 1.0967 0.0198 0.058 Uiso 1 1 calc GR . . . .
C10 C 0.13200(5) 0.9335(3) 0.18881(14) 0.0255(4) Uani 1 1 d . . . . .
C11 C 0.09364(6) 0.9476(4) 0.14096(16) 0.0360(5) Uani 1 1 d . . . . .
C12 C 0.08254(6) 0.6328(4) 0.25890(17) 0.0340(5) Uani 1 1 d . . . . .
C13 C 0.12081(5) 0.6224(3) 0.30947(14) 0.0260(4) Uani 1 1 d . . . . .
C14 C 0.25007(6) 1.2680(3) 0.44041(14) 0.0281(4) Uani 1 1 d . . . . .
H14A H 0.2244 1.2804 0.3952 0.034 Uiso 1 1 calc R . . . .
H14B H 0.2629 1.4175 0.4331 0.034 Uiso 1 1 calc R . . . .
C15 C 0.06873(6) 0.7991(4) 0.17558(18) 0.0418(5) Uani 1 1 d . . . . .


_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 C13 1.7224(18) . ?
Cl2 C12 1.720(2) . ?
Cl3 C11 1.7327(19) . ?
Cl4 C15 1.711(2) . ?
O1 C8 1.262(2) . ?
O2 C8 1.243(2) . ?
N1 C14 1.487(2) . ?
O3 C6 1.203(2) . ?
C6 O4 1.310(2) . ?
C6 C10 1.511(2) . ?
C7 C8 1.509(2) . ?
C7 C10 1.392(2) . ?
C7 C13 1.393(2) . ?
C10 C11 1.386(3) . ?
C11 C15 1.384(3) . ?
C12 C13 1.389(3) . ?
C12 C15 1.387(3) . ?
C14 C14 1.511(3) 7_576 ?

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
O3 C6 O4 125.63(17) . . ?
O3 C6 C10 124.52(17) . . ?
O4 C6 C10 109.85(15) . . ?
C10 C7 C8 118.58(16) . . ?
C10 C7 C13 118.99(17) . . ?
C13 C7 C8 122.43(15) . . ?
O1 C8 C7 118.34(15) . . ?
O2 C8 O1 122.93(17) . . ?
O2 C8 C7 118.65(15) . . ?
C7 C10 C6 121.13(16) . . ?
C11 C10 C6 118.89(16) . . ?
C11 C10 C7 119.95(17) . . ?
C10 C11 Cl3 119.22(15) . . ?
C15 C11 Cl3 119.77(16) . . ?
C15 C11 C10 121.00(18) . . ?
C13 C12 Cl2 120.26(15) . . ?
C15 C12 Cl2 119.65(16) . . ?
C15 C12 C13 120.08(18) . . ?
C7 C13 Cl1 121.20(14) . . ?
C12 C13 Cl1 118.06(14) . . ?
C12 C13 C7 120.66(16) . . ?
N1 C14 C14 110.65(18) . 7_576 ?
C11 C15 Cl4 120.30(16) . . ?
C11 C15 C12 119.24(19) . . ?
C12 C15 Cl4 120.43(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound6
_database_code_depnum_ccdc_archive 'CCDC 1032984'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 Cl4 O4, 2(C5 H8 N3 O), 2(H2 O)'
_chemical_formula_sum            'C18 H20 Cl4 N6 O8'
_chemical_formula_weight         590.20
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.4149(4)
_cell_length_b                   8.9129(6)
_cell_length_c                   18.7130(11)
_cell_angle_alpha                97.470(5)
_cell_angle_beta                 97.712(5)
_cell_angle_gamma                98.484(5)
_cell_volume                     1197.87(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8950
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.22
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2812
_reflns_number_total             4215
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1262
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O7-H7B
 0.85 with sigma of 0.01
 H2-H7B
 2.2 with sigma of 0.01
3.a Free rotating group:
 O7(H7A), O6(H6C,H6D)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C30(H30), N4(H4), N5(H5), C22(H22)
3.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N6(H6A,H6B)
3.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.37940(13) 0.83148(10) 0.12197(5) 0.0538(3) Uani 1 d . . .
Cl2 Cl 0.25246(14) 0.12196(10) 0.03444(5) 0.0558(3) Uani 1 d . . .
Cl3 Cl 0.22724(13) 0.68305(11) -0.03976(5) 0.0550(3) Uani 1 d . . .
Cl4 Cl 0.15793(13) 0.32719(11) -0.08194(4) 0.0547(3) Uani 1 d . . .
O4 O 0.6196(3) 0.6344(3) 0.25184(12) 0.0444(6) Uani 1 d . . .
O2 O 0.5514(3) 0.2149(3) 0.17392(12) 0.0535(7) Uani 1 d . . .
C5 C 0.2746(4) 0.5694(4) 0.02559(16) 0.0340(7) Uani 1 d . . .
C6 C 0.3419(4) 0.6333(4) 0.09706(16) 0.0334(7) Uani 1 d . . .
C7 C 0.3612(4) 0.3832(3) 0.13073(15) 0.0293(7) Uani 1 d . . .
N1 N 0.7213(3) 0.0599(3) 0.26382(14) 0.0375(7) Uani 1 d . . .
H1 H 0.6623 0.1113 0.2356 0.045 Uiso 1 calc . . R
C10 C 0.2459(4) 0.4102(4) 0.00675(16) 0.0351(8) Uani 1 d . . .
O1 O 0.3559(3) 0.2902(3) 0.24511(12) 0.0459(6) Uani 1 d . . .
C12 C 0.3840(3) 0.5426(3) 0.15055(15) 0.0281(7) Uani 1 d . . .
C13 C 0.4259(4) 0.2882(4) 0.18793(16) 0.0331(7) Uani 1 d . . .
C14 C 0.4503(4) 0.6165(4) 0.22937(16) 0.0327(7) Uani 1 d . . .
C15 C 0.2913(4) 0.3192(4) 0.05907(16) 0.0341(7) Uani 1 d . . .
O3 O 0.3278(3) 0.6516(3) 0.26424(12) 0.0517(7) Uani 1 d . . .
N2 N 0.7543(3) -0.0450(3) 0.37007(15) 0.0430(7) Uani 1 d . . .
H2 H 0.7170 -0.0582 0.4107 0.052 Uiso 1 calc . . DR
C21 C 0.6583(4) 0.0309(4) 0.32516(17) 0.0374(8) Uani 1 d . . .
N3 N 0.5077(4) 0.0800(3) 0.34184(15) 0.0491(8) Uani 1 d . . .
H3A H 0.4494 0.1309 0.3132 0.059 Uiso 1 calc . . R
H3B H 0.4678 0.0610 0.3814 0.059 Uiso 1 calc . . R
C26 C 0.8779(4) 0.0099(4) 0.24450(17) 0.0383(8) Uani 1 d . . .
O5 O 0.9818(3) -0.1783(3) 0.39810(15) 0.0671(8) Uani 1 d . . .
C28 C 0.9290(5) 0.0536(4) 0.17442(18) 0.0523(9) Uani 1 d . . .
H28A H 0.8341 0.0046 0.1348 0.078 Uiso 1 calc . . GR
H28B H 1.0437 0.0213 0.1668 0.078 Uiso 1 calc . . GR
H28C H 0.9418 0.1630 0.1767 0.078 Uiso 1 calc . . GR
C29 C 0.9116(5) -0.1038(4) 0.35434(19) 0.0462(9) Uani 1 d . . .
C30 C 0.9716(4) -0.0687(4) 0.2883(2) 0.0468(9) Uani 1 d . . .
H30 H 1.0780 -0.1012 0.2754 0.056 Uiso 1 calc . . R
O8 O 1.2169(3) 0.2531(3) 0.40178(12) 0.0517(7) Uani 1 d . . .
N4 N 0.8119(3) 0.4712(3) 0.33407(13) 0.0356(6) Uani 1 d . . .
H4 H 0.7219 0.5137 0.3169 0.043 Uiso 1 calc . . R
N5 N 1.0832(3) 0.3830(3) 0.32009(13) 0.0353(6) Uani 1 d . . .
H5 H 1.1699 0.3721 0.2945 0.042 Uiso 1 calc . . R
C18 C 1.0892(4) 0.3213(4) 0.38477(16) 0.0359(8) Uani 1 d . . .
C19 C 0.9505(4) 0.4583(4) 0.29540(16) 0.0344(8) Uani 1 d . . .
C22 C 0.9420(4) 0.3444(4) 0.42480(16) 0.0378(8) Uani 1 d . . .
H22 H 0.9388 0.3070 0.4688 0.045 Uiso 1 calc . . R
C24 C 0.8081(4) 0.4194(4) 0.39990(16) 0.0361(8) Uani 1 d . . .
N6 N 0.9518(4) 0.5149(4) 0.23450(15) 0.0530(8) Uani 1 d . . .
H6A H 1.0393 0.5041 0.2094 0.064 Uiso 1 calc . . R
H6B H 0.8651 0.5630 0.2195 0.064 Uiso 1 calc . . R
C32 C 0.6531(4) 0.4565(5) 0.43805(19) 0.0519(10) Uani 1 d . . .
H32A H 0.6651 0.5659 0.4506 0.078 Uiso 1 calc . . GR
H32B H 0.6562 0.4104 0.4817 0.078 Uiso 1 calc . . GR
H32C H 0.5380 0.4174 0.4065 0.078 Uiso 1 calc . . GR
O7 O 0.6310(4) -0.0983(4) 0.49801(15) 0.0672(8) Uani 1 d . . D
H7A H 0.6953 -0.1595 0.5164 0.101 Uiso 1 d . . G
O6 O 0.3290(4) -0.2646(4) 0.41065(14) 0.0796(10) Uani 1 d . . .
H6C H 0.3336 -0.3016 0.3669 0.119 Uiso 1 d . . G
H6D H 0.2316 -0.2252 0.4121 0.119 Uiso 1 d . . G
H7B H 0.530(5) -0.158(7) 0.4800(8) 0.22(4) Uiso 1 d . . D


_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 C6 1.738(3) . ?
Cl2 C15 1.729(3) . ?
Cl3 C5 1.720(3) . ?
Cl4 C10 1.725(3) . ?
O4 C14 1.249(3) . ?
O2 C13 1.250(4) . ?
C5 C6 1.379(4) . ?
C5 C10 1.394(4) . ?
C6 C12 1.398(4) . ?
C7 C12 1.400(4) . ?
C7 C13 1.520(4) . ?
C7 C15 1.385(4) . ?
N1 C21 1.337(4) . ?
N1 C26 1.379(4) . ?
C10 C15 1.389(4) . ?
O1 C13 1.249(4) . ?
C12 C14 1.519(4) . ?
C14 O3 1.240(4) . ?
N2 C21 1.342(4) . ?
N2 C29 1.398(4) . ?
C21 N3 1.318(4) . ?
C26 C28 1.496(5) . ?
C26 C30 1.336(5) . ?
O5 C29 1.229(4) . ?
C29 C30 1.425(5) . ?
O8 C18 1.228(4) . ?
N4 C19 1.344(4) . ?
N4 C24 1.373(4) . ?
N5 C18 1.391(4) . ?
N5 C19 1.336(4) . ?
C18 C22 1.429(4) . ?
C19 N6 1.306(4) . ?
C22 C24 1.342(4) . ?
C24 C32 1.487(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C5 Cl3 121.0(3) . . ?
C6 C5 C10 118.9(3) . . ?
C10 C5 Cl3 120.1(2) . . ?
C5 C6 Cl1 119.8(2) . . ?
C5 C6 C12 121.6(3) . . ?
C12 C6 Cl1 118.5(2) . . ?
C12 C7 C13 118.3(2) . . ?
C15 C7 C12 119.0(3) . . ?
C15 C7 C13 122.5(3) . . ?
C21 N1 C26 121.9(3) . . ?
C5 C10 Cl4 119.8(2) . . ?
C15 C10 Cl4 120.2(2) . . ?
C15 C10 C5 119.9(3) . . ?
C6 C12 C7 119.2(3) . . ?
C6 C12 C14 120.2(3) . . ?
C7 C12 C14 120.7(3) . . ?
O2 C13 C7 115.8(3) . . ?
O1 C13 O2 124.7(3) . . ?
O1 C13 C7 119.5(3) . . ?
O4 C14 C12 117.1(3) . . ?
O3 C14 O4 127.4(3) . . ?
O3 C14 C12 115.4(2) . . ?
C7 C15 Cl2 119.7(2) . . ?
C7 C15 C10 121.3(3) . . ?
C10 C15 Cl2 119.0(2) . . ?
C21 N2 C29 123.6(3) . . ?
N1 C21 N2 118.7(3) . . ?
N3 C21 N1 120.4(3) . . ?
N3 C21 N2 120.9(3) . . ?
N1 C26 C28 114.8(3) . . ?
C30 C26 N1 119.6(3) . . ?
C30 C26 C28 125.7(3) . . ?
N2 C29 C30 114.9(3) . . ?
O5 C29 N2 117.4(3) . . ?
O5 C29 C30 127.7(3) . . ?
C26 C30 C29 121.3(3) . . ?
C19 N4 C24 122.6(3) . . ?
C19 N5 C18 123.7(3) . . ?
O8 C18 N5 118.1(3) . . ?
O8 C18 C22 126.6(3) . . ?
N5 C18 C22 115.3(3) . . ?
N5 C19 N4 118.2(3) . . ?
N6 C19 N4 120.4(3) . . ?
N6 C19 N5 121.4(3) . . ?
C24 C22 C18 121.0(3) . . ?
N4 C24 C32 115.0(3) . . ?
C22 C24 N4 119.0(3) . . ?
C22 C24 C32 126.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound7
_database_code_depnum_ccdc_archive 'CCDC 1032985'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 Cl4 O4, C16 H20 N4, 2(H2 O)'
_chemical_formula_sum            'C24 H24 Cl4 N4 O6'
_chemical_formula_weight         606.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 N1 Cd1'
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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.6127(5)
_cell_length_b                   23.7989(9)
_cell_length_c                   9.5324(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.590(4)
_cell_angle_gamma                90.00
_cell_volume                     2829.23(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8030
_cell_measurement_theta_min      3.0310
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6437
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.65
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   12.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  -38.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega  -95.00   31.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  -19.0000  150.0000 126
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0124318000
_diffrn_orient_matrix_UB_12      0.0266880000
_diffrn_orient_matrix_UB_13      0.0263648000
_diffrn_orient_matrix_UB_21      0.0524438000
_diffrn_orient_matrix_UB_22      0.0017885000
_diffrn_orient_matrix_UB_23      0.0388472000
_diffrn_orient_matrix_UB_31      0.0181896000
_diffrn_orient_matrix_UB_32      0.0131493000
_diffrn_orient_matrix_UB_33      -0.0587958000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2057
_reflns_number_total             2925
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0506P)²+4.4516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1551
_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. 
;
_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,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C19(H19)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.29478(9) 0.43525(6) 0.02419(14) 0.1241(5) Uani 1 d . . .
Cl2 Cl 0.40065(14) 0.54894(5) 0.1304(3) 0.1865(10) Uani 1 d . . .
O1 O 0.33891(16) 0.30883(9) 0.2134(2) 0.0637(6) Uani 1 d . . .
N2 N 0.19485(16) 0.32800(9) 0.6327(2) 0.0458(5) Uani 1 d . . .
N1 N 0.30073(18) 0.32576(10) 0.4768(3) 0.0523(6) Uani 1 d . . .
O2 O 0.43140(19) 0.31157(11) 0.0351(2) 0.0811(7) Uani 1 d . . .
C7 C 0.4045(2) 0.33067(13) 0.1444(3) 0.0488(6) Uani 1 d . . .
C8 C 0.0489(2) 0.38259(11) 0.7232(3) 0.0470(6) Uani 1 d . . .
O3 O 0.1324(2) 0.29601(12) 1.0432(3) 0.0862(8) Uani 1 d . . .
H3A H 0.1963 0.2965 1.0869 0.129 Uiso 1 d . . G
H3B H 0.1150 0.2625 1.0186 0.129 Uiso 1 d . . G
C10 C 0.1995(2) 0.33239(12) 0.4946(3) 0.0489(6) Uani 1 d . . .
C11 C 0.4544(2) 0.38579(12) 0.1992(3) 0.0501(7) Uani 1 d . . .
C12 C 0.0967(2) 0.32639(12) 0.6978(3) 0.0530(7) Uani 1 d . . .
H12A H 0.1123 0.3069 0.7879 0.064 Uiso 1 calc . . R
H12B H 0.0435 0.3045 0.6372 0.064 Uiso 1 calc . . R
C13 C 0.2965(2) 0.31821(13) 0.7029(3) 0.0552(7) Uani 1 d . . .
H13 H 0.3160 0.3135 0.8002 0.066 Uiso 1 calc . . R
C14 C 0.3620(2) 0.31681(13) 0.6052(3) 0.0586(7) Uani 1 d . . .
H14 H 0.4357 0.3109 0.6216 0.070 Uiso 1 calc . . R
C15 C 0.0957(3) 0.43316(13) 0.6980(4) 0.0682(9) Uani 1 d . . .
H15 H 0.1605 0.4334 0.6625 0.082 Uiso 1 calc . . R
C16 C 0.1088(3) 0.34368(18) 0.3820(3) 0.0803(11) Uani 1 d . . .
H16A H 0.0492 0.3203 0.3957 0.120 Uiso 1 calc . . GR
H16B H 0.1296 0.3357 0.2912 0.120 Uiso 1 calc . . GR
H16C H 0.0883 0.3824 0.3855 0.120 Uiso 1 calc . . GR
C17 C 0.4089(3) 0.43628(15) 0.1489(4) 0.0746(10) Uani 1 d . . .
C18 C 0.4549(3) 0.48658(15) 0.1987(6) 0.0993(17) Uani 1 d . . .
C19 C 0.0482(3) 0.48334(16) 0.7245(5) 0.0982(14) Uani 1 d . . .
H19 H 0.0811 0.5171 0.7079 0.118 Uiso 1 calc . . R
H1 H 0.319(3) 0.3241(14) 0.386(4) 0.079(10) Uiso 1 d . . .


_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 C17 1.725(4) . ?
Cl2 C18 1.721(4) . ?
O1 C7 1.244(3) . ?
N2 C10 1.331(3) . ?
N2 C12 1.465(3) . ?
N2 C13 1.375(3) . ?
N1 C10 1.322(3) . ?
N1 C14 1.363(4) . ?
O2 C7 1.231(3) . ?
C7 C11 1.514(4) . ?
C8 C8 1.403(5) 2_556 ?
C8 C12 1.502(4) . ?
C8 C15 1.377(4) . ?
C10 C16 1.472(4) . ?
C11 C11 1.389(5) 2_655 ?
C11 C17 1.386(4) . ?
C13 C14 1.335(4) . ?
C15 C19 1.376(5) . ?
C17 C18 1.383(5) . ?
C18 C18 1.385(10) 2_655 ?
C19 C19 1.375(7) 2_556 ?

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
C10 N2 C12 125.9(2) . . ?
C10 N2 C13 108.6(2) . . ?
C13 N2 C12 125.1(2) . . ?
C10 N1 C14 109.5(2) . . ?
O1 C7 C11 117.1(2) . . ?
O2 C7 O1 125.6(3) . . ?
O2 C7 C11 117.3(2) . . ?
C8 C8 C12 117.05(13) 2_556 . ?
C15 C8 C8 119.10(17) . 2_556 ?
C15 C8 C12 123.8(2) . . ?
N2 C10 C16 126.3(2) . . ?
N1 C10 N2 107.6(2) . . ?
N1 C10 C16 126.1(2) . . ?
C11 C11 C7 119.93(14) 2_655 . ?
C17 C11 C7 120.2(3) . . ?
C17 C11 C11 119.9(2) . 2_655 ?
N2 C12 C8 115.5(2) . . ?
C14 C13 N2 107.1(2) . . ?
C13 C14 N1 107.2(2) . . ?
C19 C15 C8 121.1(3) . . ?
C11 C17 Cl1 119.0(3) . . ?
C18 C17 Cl1 120.9(3) . . ?
C18 C17 C11 120.1(4) . . ?
C17 C18 Cl2 119.6(4) . . ?
C17 C18 C18 120.0(2) . 2_655 ?
C18 C18 Cl2 120.35(18) 2_655 . ?
C19 C19 C15 119.82(19) 2_556 . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound8
_database_code_depnum_ccdc_archive 'CCDC 1032986'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H Cl4 O4, C7 H7 N2, H2 O'
_chemical_formula_sum            'C15 H10 Cl4 N2 O5'
_chemical_formula_weight         440.05
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.047(4)
_cell_length_b                   8.497(5)
_cell_length_c                   15.269(9)
_cell_angle_alpha                84.240(9)
_cell_angle_beta                 83.995(10)
_cell_angle_gamma                72.863(9)
_cell_volume                     866.5(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1313
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.161
_cell_measurement_theta_min      2.515
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_av_unetI/netI     0.1025
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4437
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.52
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1918
_reflns_number_total             3006
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0891
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1508P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2169
_refine_ls_wR_factor_ref         0.2354
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.2805(2) 0.41805(16) 0.37529(11) 0.0654(5) Uani 1 d . . .
Cl2 Cl 0.1049(3) 1.05029(18) 0.11928(9) 0.0688(5) Uani 1 d . . .
Cl3 Cl 0.3484(2) 0.38782(18) 0.17253(11) 0.0737(6) Uani 1 d . . .
Cl4 Cl 0.2704(2) 0.7055(2) 0.04445(9) 0.0676(5) Uani 1 d . . .
O2 O 0.1252(5) 1.0918(4) 0.3749(2) 0.0512(9) Uani 1 d . . .
C29 C 0.0246(8) 1.0558(6) 0.3201(3) 0.0411(12) Uani 1 d . . .
C1 C 0.2651(7) 0.5791(6) 0.2143(3) 0.0442(12) Uani 1 d . . .
C2 C 0.1165(7) 0.8897(6) 0.2811(3) 0.0380(11) Uani 1 d . . .
C3 C 0.2346(7) 0.5938(6) 0.3047(3) 0.0411(11) Uani 1 d . . .
O4 O 0.2872(6) 0.7220(5) 0.4799(2) 0.0578(10) Uani 1 d . . .
C6 C 0.1460(8) 0.7601(6) 0.4376(3) 0.0408(11) Uani 1 d . . .
C7 C 0.1662(7) 0.7473(5) 0.3382(3) 0.0351(11) Uani 1 d . . .
N2 N 0.3288(6) 0.2795(5) 0.6600(3) 0.0492(11) Uani 1 d . . .
H2 H 0.3659 0.1965 0.6278 0.059 Uiso 1 calc . . R
C9 C 0.1516(7) 0.8752(6) 0.1909(3) 0.0426(12) Uani 1 d . . .
O1 O -0.1398(6) 1.1400(4) 0.2971(3) 0.0610(11) Uani 1 d . . .
C11 C 0.2269(7) 0.7204(6) 0.1565(3) 0.0442(12) Uani 1 d . . .
C12 C 0.3023(7) 0.2698(6) 0.7508(3) 0.0441(12) Uani 1 d . . .
C13 C 0.2424(7) 0.4313(6) 0.7749(3) 0.0471(13) Uani 1 d . . .
O5 O 0.5279(6) 1.0153(5) 0.4059(3) 0.0745(13) Uani 1 d . . .
H5A H 0.4077 1.0624 0.3948 0.112 Uiso 1 d . . G
H5B H 0.5910 1.0871 0.4029 0.112 Uiso 1 d . . G
N1 N 0.2347(6) 0.5310(5) 0.6973(3) 0.0532(12) Uani 1 d . . .
H1 H 0.2007 0.6372 0.6932 0.064 Uiso 1 calc . . R
C16 C 0.3265(8) 0.1370(7) 0.8137(4) 0.0556(14) Uani 1 d . . .
H16 H 0.3661 0.0284 0.7980 0.067 Uiso 1 calc . . R
C17 C 0.2887(8) 0.4350(7) 0.6302(4) 0.0545(14) Uani 1 d . . .
H17 H 0.2968 0.4725 0.5709 0.065 Uiso 1 calc . . R
C18 C 0.2015(9) 0.4682(9) 0.8630(4) 0.0652(16) Uani 1 d . . .
H18 H 0.1586 0.5764 0.8794 0.078 Uiso 1 calc . . R
C19 C 0.2891(10) 0.1742(9) 0.8994(4) 0.0724(19) Uani 1 d . . .
H19 H 0.3046 0.0885 0.9434 0.087 Uiso 1 calc . . R
C20 C 0.2283(10) 0.3359(11) 0.9236(4) 0.077(2) Uani 1 d . . .
H20 H 0.2051 0.3546 0.9833 0.093 Uiso 1 calc . . R
O3 O -0.0401(5) 0.8145(5) 0.4674(2) 0.0515(9) Uani 1 d . . .
H3 H -0.0464 0.8254 0.5205 0.077 Uiso 1 calc . . GR


_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 C3 1.721(5) . ?
Cl2 C9 1.726(5) . ?
Cl3 C1 1.721(5) . ?
Cl4 C11 1.718(5) . ?
O2 C29 1.265(6) . ?
C29 C2 1.521(6) . ?
C29 O1 1.234(6) . ?
C1 C3 1.387(7) . ?
C1 C11 1.392(7) . ?
C2 C7 1.396(6) . ?
C2 C9 1.386(7) . ?
C3 C7 1.381(6) . ?
O4 C6 1.189(6) . ?
C6 C7 1.522(6) . ?
C6 O3 1.304(6) . ?
N2 C12 1.377(6) . ?
N2 C17 1.312(6) . ?
C9 C11 1.398(7) . ?
C12 C13 1.387(7) . ?
C12 C16 1.389(7) . ?
C13 N1 1.381(7) . ?
C13 C18 1.393(8) . ?
N1 C17 1.329(7) . ?
C16 C19 1.357(8) . ?
C18 C20 1.363(9) . ?
C19 C20 1.389(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
O2 C29 C2 115.6(4) . . ?
O1 C29 O2 126.5(5) . . ?
O1 C29 C2 117.9(4) . . ?
C3 C1 Cl3 120.7(4) . . ?
C3 C1 C11 119.8(4) . . ?
C11 C1 Cl3 119.5(4) . . ?
C7 C2 C29 118.9(4) . . ?
C9 C2 C29 122.1(4) . . ?
C9 C2 C7 119.0(4) . . ?
C1 C3 Cl1 119.3(4) . . ?
C7 C3 Cl1 120.0(4) . . ?
C7 C3 C1 120.7(4) . . ?
O4 C6 C7 121.8(5) . . ?
O4 C6 O3 126.7(5) . . ?
O3 C6 C7 111.5(4) . . ?
C2 C7 C6 120.3(4) . . ?
C3 C7 C2 120.1(4) . . ?
C3 C7 C6 119.6(4) . . ?
C17 N2 C12 109.3(5) . . ?
C2 C9 Cl2 119.8(4) . . ?
C2 C9 C11 121.1(4) . . ?
C11 C9 Cl2 119.1(4) . . ?
C1 C11 Cl4 120.6(4) . . ?
C1 C11 C9 119.2(4) . . ?
C9 C11 Cl4 120.2(4) . . ?
N2 C12 C13 106.1(4) . . ?
N2 C12 C16 132.5(5) . . ?
C13 C12 C16 121.4(5) . . ?
C12 C13 C18 121.8(5) . . ?
N1 C13 C12 106.4(5) . . ?
N1 C13 C18 131.8(5) . . ?
C17 N1 C13 108.4(4) . . ?
C19 C16 C12 116.4(6) . . ?
N2 C17 N1 109.8(5) . . ?
C20 C18 C13 115.8(6) . . ?
C16 C19 C20 122.3(6) . . ?
C18 C20 C19 122.4(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
