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

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 976639'
_audit_update_record             
;
2015-05-30 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Cl2 N5 O11'
_chemical_formula_weight         574.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.7180(5)
_cell_length_b                   10.2978(5)
_cell_length_c                   12.2586(5)
_cell_angle_alpha                89.871(4)
_cell_angle_beta                 80.340(4)
_cell_angle_gamma                74.104(4)
_cell_volume                     1161.89(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.353
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18302
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.230
_diffrn_reflns_theta_max         29.078
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5381
_reflns_number_gt                4320
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2014
_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     
'w=1/[σ²(Fo²)+(0.0487P)²+4.8780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5381
_refine_ls_number_parameters     346
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0973
_refine_ls_wR_factor_ref         0.2281
_refine_ls_wR_factor_gt          0.2217
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9057(4) 0.7694(4) 0.5344(3) 0.0396(9) Uani 1 1 d . . . . .
H1 H 0.9455 0.8360 0.5554 0.048 Uiso 1 1 calc R U . . .
C2 C 0.9687(5) 0.6902(5) 0.4407(4) 0.0476(11) Uani 1 1 d . . . . .
H2 H 1.0525 0.7019 0.3976 0.057 Uiso 1 1 calc R U . . .
C3 C 0.9069(6) 0.5908(5) 0.4091(4) 0.0517(12) Uani 1 1 d . . . . .
H3 H 0.9520 0.5353 0.3462 0.062 Uiso 1 1 calc R U . . .
C4 C 0.7816(5) 0.5744(4) 0.4693(4) 0.0476(11) Uani 1 1 d . . . . .
H4 H 0.7395 0.5100 0.4474 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7189(4) 0.6570(4) 0.5645(3) 0.0373(9) Uani 1 1 d . . . . .
C6 C 0.5733(4) 0.7681(4) 0.7178(3) 0.0345(8) Uani 1 1 d . . . . .
C7 C 0.6957(4) 0.8212(4) 0.6943(3) 0.0323(8) Uani 1 1 d . . . . .
C8 C 0.7403(4) 0.9024(4) 0.7674(3) 0.0308(8) Uani 1 1 d . . . . .
C9 C 0.6462(4) 1.0057(4) 0.8354(3) 0.0328(8) Uani 1 1 d . . . . .
C10 C 0.4329(4) 1.0794(4) 0.7352(4) 0.0395(9) Uani 1 1 d . . . . .
H10 H 0.4753 1.0191 0.6747 0.047 Uiso 1 1 calc R U . . .
C11 C 0.2987(5) 1.1681(5) 0.7386(5) 0.0521(12) Uani 1 1 d . . . . .
H11 H 0.2496 1.1686 0.6796 0.062 Uiso 1 1 calc R U . . .
C12 C 0.2349(5) 1.2572(5) 0.8292(5) 0.0611(14) Uani 1 1 d . . . . .
H12 H 0.1421 1.3147 0.8314 0.073 Uiso 1 1 calc R U . . .
C13 C 0.3071(6) 1.2616(5) 0.9156(5) 0.0584(13) Uani 1 1 d . . . . .
H13 H 0.2657 1.3225 0.9758 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4442(5) 1.1719(4) 0.9098(4) 0.0403(9) Uani 1 1 d . . . . .
C15 C 0.6676(5) 1.0573(4) 0.9422(3) 0.0393(9) Uani 1 1 d . . . . .
C16 C 0.8959(4) 0.8644(4) 0.7821(3) 0.0323(8) Uani 1 1 d . . . . .
C17 C 0.9708(5) 0.9601(5) 0.7812(4) 0.0459(10) Uani 1 1 d . . . . .
H17 H 0.9266 1.0501 0.7697 0.055 Uiso 1 1 calc R U . . .
C18 C 1.1136(5) 0.9195(6) 0.7977(4) 0.0571(13) Uani 1 1 d . . . . .
H18 H 1.1657 0.9829 0.7980 0.069 Uiso 1 1 calc R U . . .
C19 C 1.1067(5) 0.6974(6) 0.8151(4) 0.0551(12) Uani 1 1 d . . . . .
H19 H 1.1543 0.6086 0.8274 0.066 Uiso 1 1 calc R U . . .
C20 C 0.9658(4) 0.7306(4) 0.7993(4) 0.0410(9) Uani 1 1 d . . . . .
H20 H 0.9169 0.6645 0.8000 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7704(2) 0.41117(16) 0.88056(15) 0.0770(5) Uani 1 1 d . . . . .
Cl2 Cl 0.70049(14) 1.16332(13) 0.50981(10) 0.0535(3) Uani 1 1 d . . . . .
N1 N 0.7829(3) 0.7500(3) 0.5977(3) 0.0331(7) Uani 1 1 d . . . . .
N2 N 0.5948(4) 0.6679(3) 0.6375(3) 0.0398(8) Uani 1 1 d . . . . .
H2A H 0.5370 0.6186 0.6341 0.048 Uiso 1 1 calc DR U . . .
N3 N 0.5034(3) 1.0812(3) 0.8220(3) 0.0334(7) Uani 1 1 d . . . . .
N4 N 0.5396(4) 1.1551(4) 0.9805(3) 0.0478(9) Uani 1 1 d . . . . .
H4A H 0.5224 1.2003 1.0425 0.057 Uiso 1 1 calc R U . . .
N5 N 1.1757(4) 0.7927(5) 0.8130(4) 0.0584(11) Uani 1 1 d . . . . .
H5 H 1.2649 0.7699 0.8220 0.070 Uiso 1 1 calc R U . . .
O1 O 0.4678(3) 0.7980(3) 0.7955(3) 0.0417(7) Uani 1 1 d . . . . .
O2 O 0.7675(4) 1.0200(4) 0.9918(3) 0.0542(9) Uani 1 1 d . . . . .
O3 O 0.8897(11) 0.4387(12) 0.9193(10) 0.213(4) Uani 1 1 d . U . . .
O4 O 0.7109(10) 0.3920(8) 0.9933(6) 0.160(3) Uani 1 1 d . U . . .
O5 O 0.7970(16) 0.3025(9) 0.8238(9) 0.237(4) Uani 1 1 d . U . . .
O6 O 0.7115(13) 0.5291(9) 0.8467(9) 0.211(4) Uani 1 1 d . U . . .
O7 O 0.5841(11) 1.2460(11) 0.5803(9) 0.224(5) Uani 1 1 d . . . . .
O8 O 0.7447(8) 1.2537(6) 0.4373(4) 0.117(2) Uani 1 1 d . . . . .
O9 O 0.6447(8) 1.0715(6) 0.4640(5) 0.135(3) Uani 1 1 d . . . . .
O10 O 0.7896(10) 1.1115(7) 0.5820(7) 0.172(4) Uani 1 1 d . . . . .
O11 O 0.4465(5) 0.4754(5) 0.7140(6) 0.1081(19) Uani 1 1 d G . . . .
H11A H 0.5052 0.4695 0.7592 0.162 Uiso 1 1 d G U . . .
H11B H 0.4913 0.4314 0.6539 0.162 Uiso 1 1 d DG U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.362(6) . ?
C1 N1 1.373(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.405(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(6) . ?
C4 H4 0.9300 . ?
C5 N2 1.354(6) . ?
C5 N1 1.372(5) . ?
C6 O1 1.247(5) . ?
C6 N2 1.377(5) . ?
C6 C7 1.427(5) . ?
C7 N1 1.408(5) . ?
C7 C8 1.423(5) . ?
C8 C9 1.370(5) . ?
C8 C16 1.496(5) . ?
C9 N3 1.429(5) . ?
C9 C15 1.480(5) . ?
C10 N3 1.361(5) . ?
C10 C11 1.366(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(6) . ?
C13 H13 0.9300 . ?
C14 N4 1.350(6) . ?
C14 N3 1.366(5) . ?
C15 O2 1.206(5) . ?
C15 N4 1.379(6) . ?
C16 C17 1.376(5) . ?
C16 C20 1.392(6) . ?
C17 C18 1.384(6) . ?
C17 H17 0.9300 . ?
C18 N5 1.308(7) . ?
C18 H18 0.9300 . ?
C19 N5 1.329(7) . ?
C19 C20 1.365(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
Cl1 O5 1.260(8) . ?
Cl1 O6 1.293(8) . ?
Cl1 O3 1.420(11) . ?
Cl1 O4 1.441(8) . ?
Cl2 O10 1.349(6) . ?
Cl2 O9 1.374(5) . ?
Cl2 O7 1.378(8) . ?
Cl2 O8 1.388(5) . ?
N2 H2A 0.8600 . ?
N4 H4A 0.8600 . ?
N5 H5 0.8600 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8500 . ?

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
C2 C1 N1 119.4(4) . . ?
C2 C1 H1 120.3 . . ?
N1 C1 H1 120.3 . . ?
C1 C2 C3 119.8(5) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 117.9(4) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
N2 C5 N1 107.7(3) . . ?
N2 C5 C4 131.5(4) . . ?
N1 C5 C4 120.9(4) . . ?
O1 C6 N2 124.1(3) . . ?
O1 C6 C7 129.7(4) . . ?
N2 C6 C7 106.1(3) . . ?
N1 C7 C8 125.4(3) . . ?
N1 C7 C6 106.1(3) . . ?
C8 C7 C6 126.6(4) . . ?
C9 C8 C7 123.8(3) . . ?
C9 C8 C16 116.9(3) . . ?
C7 C8 C16 118.9(3) . . ?
C8 C9 N3 127.5(3) . . ?
C8 C9 C15 127.2(4) . . ?
N3 C9 C15 105.2(3) . . ?
N3 C10 C11 118.7(4) . . ?
N3 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C10 C11 C12 120.7(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 117.6(5) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
N4 C14 N3 108.6(4) . . ?
N4 C14 C13 130.5(4) . . ?
N3 C14 C13 120.9(4) . . ?
O2 C15 N4 125.2(4) . . ?
O2 C15 C9 130.0(4) . . ?
N4 C15 C9 104.6(3) . . ?
C17 C16 C20 119.1(4) . . ?
C17 C16 C8 121.1(4) . . ?
C20 C16 C8 119.8(3) . . ?
C16 C17 C18 118.5(5) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
N5 C18 C17 120.5(4) . . ?
N5 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N5 C19 C20 119.7(5) . . ?
N5 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C16 119.4(4) . . ?
C19 C20 H20 120.3 . . ?
C16 C20 H20 120.3 . . ?
O5 Cl1 O6 123.9(7) . . ?
O5 Cl1 O3 116.6(8) . . ?
O6 Cl1 O3 99.4(7) . . ?
O5 Cl1 O4 109.4(6) . . ?
O6 Cl1 O4 113.1(7) . . ?
O3 Cl1 O4 88.7(6) . . ?
O10 Cl2 O9 114.5(4) . . ?
O10 Cl2 O7 100.7(7) . . ?
O9 Cl2 O7 104.8(6) . . ?
O10 Cl2 O8 115.8(4) . . ?
O9 Cl2 O8 115.5(4) . . ?
O7 Cl2 O8 102.7(6) . . ?
C5 N1 C1 120.8(3) . . ?
C5 N1 C7 109.0(3) . . ?
C1 N1 C7 130.0(3) . . ?
C5 N2 C6 111.1(3) . . ?
C5 N2 H2A 124.4 . . ?
C6 N2 H2A 124.4 . . ?
C10 N3 C14 121.2(4) . . ?
C10 N3 C9 129.5(3) . . ?
C14 N3 C9 109.0(3) . . ?
C14 N4 C15 112.5(4) . . ?
C14 N4 H4A 123.8 . . ?
C15 N4 H4A 123.8 . . ?
C18 N5 C19 122.8(4) . . ?
C18 N5 H5 118.6 . . ?
C19 N5 H5 118.6 . . ?
H11A O11 H11B 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O11 0.86 2.08 2.826(6) 145.0 .
N4 H4A O1 0.86 2.00 2.774(5) 148.7 2_677
N5 H5 O1 0.86 2.04 2.827(5) 151.1 1_655
O11 H11B O7 0.85 2.02 2.758(11) 145.4 1_545

_refine_diff_density_max         1.376
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc142sbb
_database_code_depnum_ccdc_archive 'CCDC 1045361'
_audit_update_record             
;
2015-05-30 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Cl2 N5 O11'
_chemical_formula_weight         574.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.9344(2)
_cell_length_b                   18.8814(6)
_cell_length_c                   14.1420(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.449(2)
_cell_angle_gamma                90
_cell_volume                     2385.60(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_process_details   
;     
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18462
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.076
_diffrn_reflns_theta_max         29.241
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5652
_reflns_number_gt                3722
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2014
_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     
'w=1/[σ²(Fo²)+(0.0832P)²+2.8481P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5652
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1794
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6339(4) 0.19471(18) 0.6771(2) 0.0438(8) Uani 1 1 d . . . . .
H1 H 0.7011 0.1604 0.6569 0.053 Uiso 1 1 calc R U . . .
C2 C 0.5495(5) 0.1837(2) 0.7552(3) 0.0572(10) Uani 1 1 d . . . . .
H2 H 0.5580 0.1411 0.7879 0.069 Uiso 1 1 calc R U . . .
C3 C 0.4516(5) 0.2346(2) 0.7867(3) 0.0610(11) Uani 1 1 d . . . . .
H3 H 0.3936 0.2257 0.8397 0.073 Uiso 1 1 calc R U . . .
C4 C 0.4385(4) 0.2985(2) 0.7405(3) 0.0542(10) Uani 1 1 d . . . . .
H4 H 0.3722 0.3332 0.7611 0.065 Uiso 1 1 calc R U . . .
C5 C 0.5280(4) 0.30925(18) 0.6621(2) 0.0420(8) Uani 1 1 d . . . . .
C6 C 0.6512(4) 0.35475(18) 0.5374(3) 0.0419(8) Uani 1 1 d . . . . .
C7 C 0.6973(4) 0.28230(17) 0.5493(2) 0.0362(7) Uani 1 1 d . . . . .
C8 C 0.7739(3) 0.24246(16) 0.4819(2) 0.0338(7) Uani 1 1 d . . . . .
C9 C 0.8797(3) 0.27089(17) 0.4218(2) 0.0359(7) Uani 1 1 d . . . . .
C10 C 0.9982(4) 0.36809(19) 0.5190(3) 0.0490(9) Uani 1 1 d . . . . .
H10 H 0.9429 0.3588 0.5730 0.059 Uiso 1 1 calc R U . . .
C11 C 1.1041(5) 0.4204(2) 0.5199(4) 0.0622(11) Uani 1 1 d . . . . .
H11 H 1.1210 0.4467 0.5745 0.075 Uiso 1 1 calc R U . . .
C12 C 1.1858(5) 0.4342(2) 0.4394(4) 0.0657(12) Uani 1 1 d . . . . .
H12 H 1.2565 0.4704 0.4400 0.079 Uiso 1 1 calc R U . . .
C13 C 1.1644(4) 0.3956(2) 0.3593(3) 0.0593(11) Uani 1 1 d . . . . .
H13 H 1.2195 0.4051 0.3051 0.071 Uiso 1 1 calc R U . . .
C14 C 1.0583(4) 0.34171(19) 0.3600(3) 0.0450(8) Uani 1 1 d . . . . .
C15 C 0.9096(4) 0.24801(18) 0.3250(2) 0.0392(7) Uani 1 1 d . . . . .
C16 C 0.7283(3) 0.16809(17) 0.4625(2) 0.0342(7) Uani 1 1 d . . . . .
C17 C 0.5806(4) 0.14815(19) 0.4549(2) 0.0407(7) Uani 1 1 d . . . . .
H17 H 0.5053 0.1808 0.4670 0.049 Uiso 1 1 calc R U . . .
C18 C 0.5441(5) 0.0796(2) 0.4293(3) 0.0548(10) Uani 1 1 d . . . . .
H18 H 0.4443 0.0663 0.4233 0.066 Uiso 1 1 calc R U . . .
C19 C 0.6551(5) 0.0317(2) 0.4129(3) 0.0603(11) Uani 1 1 d . . . . .
H19 H 0.6317 -0.0142 0.3942 0.072 Uiso 1 1 calc R U . . .
C20 C 0.8030(5) 0.0522(2) 0.4244(3) 0.0555(10) Uani 1 1 d . . . . .
H20 H 0.8800 0.0198 0.4154 0.067 Uiso 1 1 calc R U . . .
Cl1 Cl 0.19809(9) 0.31072(5) 0.04712(6) 0.0510(3) Uani 1 1 d . . . . .
Cl2 Cl 0.83702(13) 0.48656(7) 0.20261(8) 0.0667(3) Uani 1 1 d . . . . .
N1 N 0.6187(3) 0.25662(14) 0.62897(19) 0.0371(6) Uani 1 1 d . . . . .
N2 N 0.5460(3) 0.36681(15) 0.6068(2) 0.0474(7) Uani 1 1 d . . . . .
H2A H 0.4981 0.4060 0.6137 0.057 Uiso 1 1 calc R U . . .
N3 N 0.9743(3) 0.32973(14) 0.4388(2) 0.0384(6) Uani 1 1 d . . . . .
N4 N 1.0196(3) 0.29461(16) 0.2932(2) 0.0468(7) Uani 1 1 d . . . . .
H4A H 1.0578 0.2933 0.2376 0.056 Uiso 1 1 calc R U . . .
N5 N 0.8337(3) 0.11876(15) 0.4484(2) 0.0426(7) Uani 1 1 d . . . . .
H5 H 0.9260 0.1308 0.4552 0.051 Uiso 1 1 calc R U . . .
O1 O 0.6903(3) 0.39815(13) 0.4779(2) 0.0543(7) Uani 1 1 d . . . . .
O2 O 0.8519(3) 0.20118(14) 0.27807(17) 0.0501(6) Uani 1 1 d . . . . .
O3 O 0.0691(3) 0.28486(18) 0.0958(2) 0.0704(9) Uani 1 1 d . . . . .
O4 O 0.2867(4) 0.2523(2) 0.0158(3) 0.0896(11) Uani 1 1 d . . . . .
O5 O 0.2867(4) 0.35336(18) 0.1074(3) 0.0843(10) Uani 1 1 d . . . . .
O6 O 0.1486(4) 0.3492(3) -0.0331(3) 0.1148(17) Uani 1 1 d . . . . .
O7 O 0.8394(5) 0.4507(3) 0.2894(3) 0.1272(18) Uani 1 1 d . . . . .
O8 O 0.6836(6) 0.4829(4) 0.1786(5) 0.180(3) Uani 1 1 d . . . . .
O9 O 0.8950(13) 0.5501(3) 0.2167(6) 0.244(5) Uani 1 1 d . . . . .
O10 O 0.9100(7) 0.4485(4) 0.1358(4) 0.172(3) Uani 1 1 d . . . . .
O11 O 0.5380(4) 0.49584(17) 0.3673(3) 0.0698(9) Uani 1 1 d G . . . .
H11A H 0.5903 0.4950 0.3174 0.105 Uiso 1 1 d G U . . .
H11B H 0.5836 0.4736 0.4111 0.105 Uiso 1 1 d G U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.359(5) . ?
C1 N1 1.359(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 N2 1.350(5) . ?
C5 N1 1.367(4) . ?
C6 O1 1.227(4) . ?
C6 N2 1.383(4) . ?
C6 C7 1.438(5) . ?
C7 C8 1.397(4) . ?
C7 N1 1.418(4) . ?
C8 C9 1.384(4) . ?
C8 C16 1.487(4) . ?
C9 N3 1.416(4) . ?
C9 C15 1.461(5) . ?
C10 N3 1.361(5) . ?
C10 C11 1.367(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(5) . ?
C13 H13 0.9300 . ?
C14 N4 1.341(5) . ?
C14 N3 1.367(4) . ?
C15 O2 1.218(4) . ?
C15 N4 1.396(4) . ?
C16 N5 1.341(4) . ?
C16 C17 1.375(4) . ?
C17 C18 1.382(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(6) . ?
C19 H19 0.9300 . ?
C20 N5 1.330(5) . ?
C20 H20 0.9300 . ?
Cl1 O5 1.411(3) . ?
Cl1 O6 1.415(3) . ?
Cl1 O4 1.429(4) . ?
Cl1 O3 1.433(3) . ?
Cl2 O9 1.321(6) . ?
Cl2 O10 1.359(5) . ?
Cl2 O7 1.402(4) . ?
Cl2 O8 1.411(5) . ?
N2 H2A 0.8600 . ?
N4 H4A 0.8600 . ?
N5 H5 0.8600 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8500 . ?

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
C2 C1 N1 119.0(4) . . ?
C2 C1 H1 120.5 . . ?
N1 C1 H1 120.5 . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 117.3(4) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
N2 C5 N1 108.2(3) . . ?
N2 C5 C4 130.8(3) . . ?
N1 C5 C4 121.0(3) . . ?
O1 C6 N2 125.1(3) . . ?
O1 C6 C7 129.2(3) . . ?
N2 C6 C7 105.7(3) . . ?
C8 C7 N1 127.3(3) . . ?
C8 C7 C6 125.0(3) . . ?
N1 C7 C6 105.9(3) . . ?
C9 C8 C7 123.4(3) . . ?
C9 C8 C16 116.1(3) . . ?
C7 C8 C16 119.9(3) . . ?
C8 C9 N3 127.5(3) . . ?
C8 C9 C15 126.2(3) . . ?
N3 C9 C15 106.1(3) . . ?
N3 C10 C11 119.7(4) . . ?
N3 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 118.5(4) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
N4 C14 N3 109.0(3) . . ?
N4 C14 C13 130.6(4) . . ?
N3 C14 C13 120.4(4) . . ?
O2 C15 N4 125.3(3) . . ?
O2 C15 C9 130.2(3) . . ?
N4 C15 C9 104.5(3) . . ?
N5 C16 C17 118.2(3) . . ?
N5 C16 C8 119.5(3) . . ?
C17 C16 C8 122.3(3) . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 119.3(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
N5 C20 C19 119.2(4) . . ?
N5 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
O5 Cl1 O6 111.2(3) . . ?
O5 Cl1 O4 108.5(2) . . ?
O6 Cl1 O4 108.6(3) . . ?
O5 Cl1 O3 110.7(2) . . ?
O6 Cl1 O3 108.2(2) . . ?
O4 Cl1 O3 109.6(2) . . ?
O9 Cl2 O10 113.3(5) . . ?
O9 Cl2 O7 107.6(5) . . ?
O10 Cl2 O7 110.5(4) . . ?
O9 Cl2 O8 117.3(6) . . ?
O10 Cl2 O8 106.1(4) . . ?
O7 Cl2 O8 101.3(3) . . ?
C1 N1 C5 120.7(3) . . ?
C1 N1 C7 130.1(3) . . ?
C5 N1 C7 108.8(3) . . ?
C5 N2 C6 111.3(3) . . ?
C5 N2 H2A 124.3 . . ?
C6 N2 H2A 124.3 . . ?
C10 N3 C14 120.5(3) . . ?
C10 N3 C9 130.5(3) . . ?
C14 N3 C9 108.8(3) . . ?
C14 N4 C15 111.6(3) . . ?
C14 N4 H4A 124.2 . . ?
C15 N4 H4A 124.2 . . ?
C20 N5 C16 123.5(3) . . ?
C20 N5 H5 118.3 . . ?
C16 N5 H5 118.3 . . ?
H11A O11 H11B 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O11 0.86 1.90 2.725(4) 159.9 3_666
N4 H4A O3 0.86 2.02 2.836(4) 159.3 1_655
N5 H5 O6 0.86 2.03 2.887(5) 175.0 4_666
O11 H11A O7 0.85 2.41 3.040(5) 131.0 .
O11 H11A O8 0.85 2.15 2.989(8) 168.5 .
O11 H11B O1 0.85 1.95 2.769(4) 160.4 .

_refine_diff_density_max         1.062
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_2
_audit_block_doi                 10.5517/cc142scc
_database_code_depnum_ccdc_archive 'CCDC 1045362'
_audit_update_record             
;
2015-05-30 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Cl2 N5 O11'
_chemical_formula_weight         574.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   32.842(7)
_cell_length_b                   8.4292(17)
_cell_length_c                   17.392(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.11(3)
_cell_angle_gamma                90
_cell_volume                     4689.2(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             2352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    0.350
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8866
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.405
_diffrn_reflns_theta_max         25.650
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             4232
_reflns_number_gt                3482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2014
_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     
'w=1/[σ²(Fo²)+(0.0989P)²+11.9986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4232
_refine_ls_number_parameters     346
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.2012
_refine_ls_wR_factor_gt          0.1910
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.34179(11) 0.2940(5) 0.2537(2) 0.0474(9) Uani 1 1 d . . . . .
H1 H 0.3350 0.3259 0.3004 0.057 Uiso 1 1 calc R U . . .
C2 C 0.31474(12) 0.3174(6) 0.1839(2) 0.0587(11) Uani 1 1 d . . . . .
H2 H 0.2886 0.3616 0.1825 0.070 Uiso 1 1 calc R U . . .
C3 C 0.32572(13) 0.2755(6) 0.1131(2) 0.0604(11) Uani 1 1 d . . . . .
H3 H 0.3068 0.2917 0.0653 0.073 Uiso 1 1 calc R U . . .
C4 C 0.36382(12) 0.2114(5) 0.1140(2) 0.0498(9) Uani 1 1 d . . . . .
H4 H 0.3715 0.1848 0.0673 0.060 Uiso 1 1 calc R U . . .
C5 C 0.39095(11) 0.1867(4) 0.18688(18) 0.0384(7) Uani 1 1 d . . . . .
C6 C 0.44687(10) 0.1364(4) 0.28584(18) 0.0348(7) Uani 1 1 d . . . . .
C7 C 0.41302(9) 0.1920(4) 0.31966(18) 0.0347(7) Uani 1 1 d . . . . .
C8 C 0.41188(9) 0.1799(4) 0.39923(18) 0.0331(7) Uani 1 1 d . . . . .
C9 C 0.44751(9) 0.1915(4) 0.45975(18) 0.0335(7) Uani 1 1 d . . . . .
C10 C 0.49472(11) 0.3726(4) 0.4033(2) 0.0421(7) Uani 1 1 d . . . . .
H10 H 0.4747 0.3963 0.3578 0.050 Uiso 1 1 calc R U . . .
C11 C 0.53381(12) 0.4378(5) 0.4157(2) 0.0518(9) Uani 1 1 d . . . . .
H11 H 0.5403 0.5069 0.3786 0.062 Uiso 1 1 calc R U . . .
C12 C 0.56374(12) 0.4013(5) 0.4835(3) 0.0564(10) Uani 1 1 d . . . . .
H12 H 0.5905 0.4430 0.4905 0.068 Uiso 1 1 calc R U . . .
C13 C 0.55432(11) 0.3045(5) 0.5402(2) 0.0500(9) Uani 1 1 d . . . . .
H13 H 0.5741 0.2813 0.5862 0.060 Uiso 1 1 calc R U . . .
C14 C 0.51411(10) 0.2420(4) 0.52664(19) 0.0396(7) Uani 1 1 d . . . . .
C15 C 0.45569(10) 0.1089(4) 0.53535(18) 0.0370(7) Uani 1 1 d . . . . .
C16 C 0.37219(10) 0.1351(4) 0.42143(19) 0.0374(7) Uani 1 1 d . . . . .
C17 C 0.34658(12) 0.0174(5) 0.3802(2) 0.0525(9) Uani 1 1 d . . . . .
H17 H 0.3537 -0.0335 0.3376 0.063 Uiso 1 1 calc R U . . .
C18 C 0.31037(14) -0.0230(6) 0.4035(3) 0.0716(13) Uani 1 1 d . . . . .
H18 H 0.2925 -0.0989 0.3752 0.086 Uiso 1 1 calc R U . . .
C19 C 0.30076(13) 0.0470(6) 0.4669(3) 0.0755(15) Uani 1 1 d . . . . .
H19 H 0.2765 0.0186 0.4826 0.091 Uiso 1 1 calc R U . . .
C20 C 0.36117(11) 0.2033(5) 0.4863(2) 0.0442(8) Uani 1 1 d . . . . .
H20 H 0.3781 0.2810 0.5154 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl 0.21089(4) 0.04104(14) 0.11519(8) 0.0690(4) Uani 1 1 d . . . . .
Cl2 Cl 0.08964(4) 0.18098(12) 0.26777(6) 0.0604(3) Uani 1 1 d . . . . .
N1 N 0.37918(8) 0.2232(3) 0.25511(15) 0.0358(6) Uani 1 1 d . . . . .
N2 N 0.43096(8) 0.1352(3) 0.20492(15) 0.0397(6) Uani 1 1 d . . . . .
H2A H 0.4447 0.1057 0.1708 0.048 Uiso 1 1 calc R U . . .
N3 N 0.48550(8) 0.2728(3) 0.45826(15) 0.0346(6) Uani 1 1 d . . . . .
N4 N 0.49625(9) 0.1472(4) 0.57233(16) 0.0444(7) Uani 1 1 d . . . . .
H4A H 0.5086 0.1148 0.6186 0.053 Uiso 1 1 calc R U . . .
N5 N 0.32625(11) 0.1573(5) 0.5070(2) 0.0646(10) Uani 1 1 d . . . . .
H5 H 0.3199 0.2002 0.5476 0.078 Uiso 1 1 calc DR U . . .
O1 O 0.48168(7) 0.0927(3) 0.32005(13) 0.0418(6) Uani 1 1 d . . . . .
O2 O 0.43339(8) 0.0166(3) 0.56139(14) 0.0468(6) Uani 1 1 d . . . . .
O3 O 0.22247(15) -0.1184(6) 0.1347(4) 0.1295(19) Uani 1 1 d . . . . .
O4 O 0.21795(19) 0.1254(8) 0.1881(3) 0.137(2) Uani 1 1 d . . . . .
O5 O 0.16834(11) 0.0431(6) 0.0799(3) 0.1071(14) Uani 1 1 d . . . . .
O6 O 0.23473(12) 0.1159(5) 0.0678(2) 0.0949(12) Uani 1 1 d . . . . .
O7 O 0.1149(4) 0.2693(14) 0.2380(4) 0.271(6) Uani 1 1 d . . . . .
O8 O 0.0784(3) 0.0418(6) 0.2322(3) 0.173(3) Uani 1 1 d . . . . .
O9 O 0.0558(3) 0.2692(11) 0.2495(8) 0.289(7) Uani 1 1 d . . . . .
O10 O 0.1036(2) 0.1651(8) 0.3468(2) 0.153(3) Uani 1 1 d . . . . .
O11 O 0.29822(15) 0.2764(7) 0.6297(3) 0.1311(19) Uani 1 1 d G . . . .
H11A H 0.2738 0.2595 0.6365 0.197 Uiso 1 1 d DG U . . .
H11B H 0.3162 0.2463 0.6703 0.197 Uiso 1 1 d DG U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.346(5) . ?
C1 N1 1.361(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9300 . ?
C5 N2 1.351(4) . ?
C5 N1 1.364(4) . ?
C6 O1 1.220(4) . ?
C6 N2 1.386(4) . ?
C6 C7 1.449(4) . ?
C7 C8 1.397(4) . ?
C7 N1 1.414(4) . ?
C8 C9 1.388(4) . ?
C8 C16 1.489(4) . ?
C9 N3 1.429(4) . ?
C9 C15 1.458(4) . ?
C10 N3 1.357(4) . ?
C10 C11 1.368(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(5) . ?
C13 H13 0.9300 . ?
C14 N4 1.351(4) . ?
C14 N3 1.363(4) . ?
C15 O2 1.223(4) . ?
C15 N4 1.380(4) . ?
C16 C20 1.386(5) . ?
C16 C17 1.391(5) . ?
C17 C18 1.383(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.350(8) . ?
C18 H18 0.9300 . ?
C19 N5 1.336(7) . ?
C19 H19 0.9300 . ?
C20 N5 1.335(5) . ?
C20 H20 0.9300 . ?
Cl1 O5 1.393(4) . ?
Cl1 O6 1.408(4) . ?
Cl1 O3 1.417(5) . ?
Cl1 O4 1.425(5) . ?
Cl2 O7 1.306(6) . ?
Cl2 O9 1.316(7) . ?
Cl2 O8 1.338(4) . ?
Cl2 O10 1.354(4) . ?
N2 H2A 0.8600 . ?
N4 H4A 0.8600 . ?
N5 H5 0.8600 . ?
O11 H11A 0.8501 . ?
O11 H11B 0.8500 . ?

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
C2 C1 N1 119.3(3) . . ?
C2 C1 H1 120.4 . . ?
N1 C1 H1 120.4 . . ?
C1 C2 C3 120.4(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
N2 C5 N1 108.8(3) . . ?
N2 C5 C4 130.4(3) . . ?
N1 C5 C4 120.7(3) . . ?
O1 C6 N2 126.1(3) . . ?
O1 C6 C7 128.3(3) . . ?
N2 C6 C7 105.5(3) . . ?
C8 C7 N1 127.4(3) . . ?
C8 C7 C6 125.0(3) . . ?
N1 C7 C6 106.0(3) . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 C16 117.2(3) . . ?
C7 C8 C16 119.8(3) . . ?
C8 C9 N3 127.5(3) . . ?
C8 C9 C15 127.0(3) . . ?
N3 C9 C15 105.2(3) . . ?
N3 C10 C11 119.3(3) . . ?
N3 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 117.7(4) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
N4 C14 N3 108.7(3) . . ?
N4 C14 C13 130.3(3) . . ?
N3 C14 C13 121.0(3) . . ?
O2 C15 N4 124.9(3) . . ?
O2 C15 C9 129.3(3) . . ?
N4 C15 C9 105.6(3) . . ?
C20 C16 C17 118.5(3) . . ?
C20 C16 C8 120.8(3) . . ?
C17 C16 C8 120.6(3) . . ?
C18 C17 C16 119.0(4) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N5 C19 C18 119.7(4) . . ?
N5 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N5 C20 C16 119.8(4) . . ?
N5 C20 H20 120.1 . . ?
C16 C20 H20 120.1 . . ?
O5 Cl1 O6 111.8(3) . . ?
O5 Cl1 O3 107.8(3) . . ?
O6 Cl1 O3 114.2(3) . . ?
O5 Cl1 O4 109.3(3) . . ?
O6 Cl1 O4 107.3(3) . . ?
O3 Cl1 O4 106.2(4) . . ?
O7 Cl2 O9 99.3(9) . . ?
O7 Cl2 O8 116.8(6) . . ?
O9 Cl2 O8 104.7(5) . . ?
O7 Cl2 O10 111.1(5) . . ?
O9 Cl2 O10 111.9(7) . . ?
O8 Cl2 O10 112.1(4) . . ?
C1 N1 C5 121.0(3) . . ?
C1 N1 C7 129.8(3) . . ?
C5 N1 C7 108.8(3) . . ?
C5 N2 C6 110.9(3) . . ?
C5 N2 H2A 124.6 . . ?
C6 N2 H2A 124.6 . . ?
C10 N3 C14 120.8(3) . . ?
C10 N3 C9 130.2(3) . . ?
C14 N3 C9 109.0(3) . . ?
C14 N4 C15 111.5(3) . . ?
C14 N4 H4A 124.3 . . ?
C15 N4 H4A 124.3 . . ?
C20 N5 C19 122.5(4) . . ?
C20 N5 H5 118.8 . . ?
C19 N5 H5 118.8 . . ?
H11A O11 H11B 109.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -2.7(7) . . . . ?
C1 C2 C3 C4 -0.3(7) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C3 C4 C5 N2 -175.3(4) . . . . ?
C3 C4 C5 N1 1.3(6) . . . . ?
O1 C6 C7 C8 -11.7(6) . . . . ?
N2 C6 C7 C8 165.5(3) . . . . ?
O1 C6 C7 N1 -178.3(3) . . . . ?
N2 C6 C7 N1 -1.1(3) . . . . ?
N1 C7 C8 C9 -162.2(3) . . . . ?
C6 C7 C8 C9 34.1(5) . . . . ?
N1 C7 C8 C16 24.8(5) . . . . ?
C6 C7 C8 C16 -138.8(3) . . . . ?
C7 C8 C9 N3 25.9(5) . . . . ?
C16 C8 C9 N3 -160.9(3) . . . . ?
C7 C8 C9 C15 -146.9(3) . . . . ?
C16 C8 C9 C15 26.3(5) . . . . ?
N3 C10 C11 C12 0.4(5) . . . . ?
C10 C11 C12 C13 -2.4(6) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
C12 C13 C14 N4 -178.6(4) . . . . ?
C12 C13 C14 N3 1.8(5) . . . . ?
C8 C9 C15 O2 -1.3(6) . . . . ?
N3 C9 C15 O2 -175.4(3) . . . . ?
C8 C9 C15 N4 174.8(3) . . . . ?
N3 C9 C15 N4 0.7(3) . . . . ?
C9 C8 C16 C20 43.9(4) . . . . ?
C7 C8 C16 C20 -142.7(3) . . . . ?
C9 C8 C16 C17 -132.3(3) . . . . ?
C7 C8 C16 C17 41.0(5) . . . . ?
C20 C16 C17 C18 2.4(6) . . . . ?
C8 C16 C17 C18 178.8(4) . . . . ?
C16 C17 C18 C19 -2.2(7) . . . . ?
C17 C18 C19 N5 0.7(7) . . . . ?
C17 C16 C20 N5 -1.2(5) . . . . ?
C8 C16 C20 N5 -177.5(3) . . . . ?
C2 C1 N1 C5 5.1(6) . . . . ?
C2 C1 N1 C7 177.1(4) . . . . ?
N2 C5 N1 C1 172.9(3) . . . . ?
C4 C5 N1 C1 -4.4(5) . . . . ?
N2 C5 N1 C7 -0.6(4) . . . . ?
C4 C5 N1 C7 -177.9(3) . . . . ?
C8 C7 N1 C1 22.2(6) . . . . ?
C6 C7 N1 C1 -171.7(3) . . . . ?
C8 C7 N1 C5 -165.1(3) . . . . ?
C6 C7 N1 C5 1.1(4) . . . . ?
N1 C5 N2 C6 -0.1(4) . . . . ?
C4 C5 N2 C6 176.8(4) . . . . ?
O1 C6 N2 C5 178.0(3) . . . . ?
C7 C6 N2 C5 0.7(4) . . . . ?
C11 C10 N3 C14 2.6(5) . . . . ?
C11 C10 N3 C9 179.4(3) . . . . ?
N4 C14 N3 C10 176.5(3) . . . . ?
C13 C14 N3 C10 -3.7(5) . . . . ?
N4 C14 N3 C9 -0.9(3) . . . . ?
C13 C14 N3 C9 178.8(3) . . . . ?
C8 C9 N3 C10 9.0(5) . . . . ?
C15 C9 N3 C10 -177.0(3) . . . . ?
C8 C9 N3 C14 -173.9(3) . . . . ?
C15 C9 N3 C14 0.1(3) . . . . ?
N3 C14 N4 C15 1.4(4) . . . . ?
C13 C14 N4 C15 -178.3(3) . . . . ?
O2 C15 N4 C14 175.0(3) . . . . ?
C9 C15 N4 C14 -1.3(4) . . . . ?
C16 C20 N5 C19 -0.4(6) . . . . ?
C18 C19 N5 C20 0.7(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.86 2.39 3.019(3) 130.4 2_655
N2 H2A O2 0.86 2.12 2.823(3) 138.4 6
N4 H4A O1 0.86 2.04 2.739(4) 138.4 5_656
N4 H4A O9 0.86 2.63 3.329(11) 138.7 8_556
N5 H5 O11 0.86 1.85 2.702(6) 170.9 .
O11 H11A O3 0.85 2.06 2.840(7) 153.0 6_556
O11 H11B O7 0.85 2.46 3.256(13) 156.7 7_556

_refine_diff_density_max         0.822
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.076

