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

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

data_Crystal1-p-xylene
_database_code_depnum_ccdc_archive 'CCDC 1842175'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H39 Cl2 N4 O6'
_chemical_formula_weight         718.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   10.7680(5)
_cell_length_b                   12.2601(6)
_cell_length_c                   13.3043(6)
_cell_angle_alpha                97.054(2)
_cell_angle_beta                 101.999(2)
_cell_angle_gamma                98.839(2)
_cell_volume                     1675.71(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      78.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             754
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.201
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_T_max  0.8227
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            22483
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.440
_diffrn_reflns_theta_max         78.703
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6810
_reflns_number_gt                5948
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.8856P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6810
_refine_ls_number_parameters     456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.34196(13) 0.20257(12) 0.14747(11) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.43437(13) 0.27277(12) 0.24692(10) 0.0166(3) Uani 1 1 d . . . . .
H2A H 0.440076 0.227683 0.303993 0.020 Uiso 1 1 calc R U . . .
H2AB H 0.398451 0.339301 0.268096 0.020 Uiso 1 1 calc R U . . .
C3 C 0.57162(13) 0.31132(12) 0.23068(11) 0.0174(3) Uani 1 1 d . . . . .
C4 C 0.62407(14) 0.20633(13) 0.19744(11) 0.0201(3) Uani 1 1 d . . . . .
H4A H 0.711768 0.228688 0.186040 0.024 Uiso 1 1 calc R U . . .
H4AB H 0.630628 0.160194 0.253733 0.024 Uiso 1 1 calc R U . . .
C5 C 0.53565(14) 0.13696(13) 0.09717(12) 0.0218(3) Uani 1 1 d . . . . .
H5 H 0.572041 0.069344 0.077251 0.026 Uiso 1 1 calc R U . . .
C6 C 0.39954(14) 0.10003(12) 0.11407(11) 0.0200(3) Uani 1 1 d . . . . .
H6A H 0.403840 0.051525 0.168483 0.024 Uiso 1 1 calc R U . . .
H6AB H 0.342931 0.056116 0.048777 0.024 Uiso 1 1 calc R U . . .
C7 C 0.56257(14) 0.38103(13) 0.14138(11) 0.0209(3) Uani 1 1 d . . . . .
H7A H 0.528508 0.449214 0.160715 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.649644 0.404348 0.129129 0.025 Uiso 1 1 calc R U . . .
C8 C 0.47283(14) 0.31120(13) 0.04161(11) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.466585 0.357422 -0.015533 0.027 Uiso 1 1 calc R U . . .
C9 C 0.33745(14) 0.27462(13) 0.05996(11) 0.0208(3) Uani 1 1 d . . . . .
H9A H 0.279957 0.231157 -0.005161 0.025 Uiso 1 1 calc R U . . .
H9AB H 0.301218 0.341645 0.078987 0.025 Uiso 1 1 calc R U . . .
C10 C 0.52845(15) 0.20794(14) 0.01003(12) 0.0248(3) Uani 1 1 d . . . . .
H10A H 0.472590 0.163769 -0.055448 0.030 Uiso 1 1 calc R U . . .
H10B H 0.615785 0.231204 -0.001755 0.030 Uiso 1 1 calc R U . . .
C11 C 0.20800(14) 0.16366(12) 0.16788(11) 0.0182(3) Uani 1 1 d . . . . .
C12 C 0.09598(14) 0.15356(12) 0.09014(11) 0.0192(3) Uani 1 1 d . . . . .
H12 H 0.101962 0.174101 0.024505 0.023 Uiso 1 1 calc R U . . .
C13 C -0.02499(14) 0.11352(12) 0.10780(12) 0.0194(3) Uani 1 1 d . . . . .
C14 C -0.03298(14) 0.08242(12) 0.20338(12) 0.0200(3) Uani 1 1 d . . . . .
C15 C 0.07731(15) 0.09333(12) 0.28242(12) 0.0208(3) Uani 1 1 d . . . . .
C16 C 0.19750(14) 0.13387(13) 0.26442(11) 0.0209(3) Uani 1 1 d . . . . .
H16 H 0.273130 0.141369 0.318226 0.025 Uiso 1 1 calc R U . . .
C17 C -0.13662(15) 0.14474(14) -0.05710(12) 0.0259(3) Uani 1 1 d . . . . .
H17A H -0.224907 0.137186 -0.098707 0.039 Uiso 1 1 calc R U . . .
H17B H -0.087427 0.101788 -0.096135 0.039 Uiso 1 1 calc R U . . .
H17C H -0.095035 0.223736 -0.041823 0.039 Uiso 1 1 calc R U . . .
C18 C -0.18710(14) -0.06388(13) 0.22800(11) 0.0208(3) Uani 1 1 d . . . . .
C19 C -0.15584(17) -0.24037(14) 0.21260(12) 0.0276(3) Uani 1 1 d . . . . .
C20 C -0.26836(18) -0.27515(15) 0.24339(14) 0.0340(4) Uani 1 1 d . . . . .
H20 H -0.293448 -0.351669 0.248389 0.041 Uiso 1 1 calc R U . . .
C21 C -0.30158(16) -0.09630(15) 0.25848(13) 0.0304(4) Uani 1 1 d . . . . .
H21 H -0.351668 -0.041858 0.274078 0.036 Uiso 1 1 calc R U . . .
C22 C 0.16080(16) 0.08845(16) 0.46262(12) 0.0293(4) Uani 1 1 d . . . . .
H22A H 0.130314 0.068845 0.523699 0.044 Uiso 1 1 calc R U . . .
H22B H 0.196245 0.168703 0.474231 0.044 Uiso 1 1 calc R U . . .
H22C H 0.228140 0.046069 0.451318 0.044 Uiso 1 1 calc R U . . .
C23 C 0.65455(13) 0.38104(12) 0.33274(11) 0.0187(3) Uani 1 1 d . . . . .
C24 C 0.61908(14) 0.47978(12) 0.37165(11) 0.0200(3) Uani 1 1 d . . . . .
H24 H 0.546014 0.503710 0.333653 0.024 Uiso 1 1 calc R U . . .
C25 C 0.69010(15) 0.54348(12) 0.46581(11) 0.0215(3) Uani 1 1 d . . . . .
C26 C 0.79669(15) 0.50795(13) 0.52072(11) 0.0231(3) Uani 1 1 d . . . . .
C27 C 0.83157(14) 0.40911(14) 0.48433(12) 0.0237(3) Uani 1 1 d . . . . .
C28 C 0.76081(14) 0.34558(13) 0.38945(11) 0.0212(3) Uani 1 1 d . . . . .
H28 H 0.785210 0.278260 0.363671 0.025 Uiso 1 1 calc R U . . .
C29 C 0.54657(17) 0.67373(14) 0.46056(12) 0.0273(3) Uani 1 1 d . . . . .
H29A H 0.533714 0.740561 0.502796 0.041 Uiso 1 1 calc R U . . .
H29B H 0.472685 0.613175 0.452804 0.041 Uiso 1 1 calc R U . . .
H29C H 0.554148 0.690620 0.391732 0.041 Uiso 1 1 calc R U . . .
C30 C 0.86874(15) 0.55029(13) 0.70407(12) 0.0229(3) Uani 1 1 d . . . . .
C31 C 0.77076(16) 0.46330(14) 0.81175(13) 0.0259(3) Uani 1 1 d . . . . .
C32 C 0.87199(17) 0.50823(15) 0.89516(13) 0.0312(4) Uani 1 1 d . . . . .
H32 H 0.869468 0.489816 0.962102 0.037 Uiso 1 1 calc R U . . .
C33 C 0.97315(16) 0.59980(14) 0.78752(12) 0.0271(3) Uani 1 1 d . . . . .
H33 H 1.043553 0.649444 0.775574 0.032 Uiso 1 1 calc R U . . .
C34 C 0.96933(17) 0.27662(16) 0.51643(14) 0.0344(4) Uani 1 1 d . . . . .
H34A H 1.044385 0.266235 0.567842 0.052 Uiso 1 1 calc R U . . .
H34B H 0.990763 0.275757 0.448297 0.052 Uiso 1 1 calc R U . . .
H34C H 0.896568 0.215968 0.511841 0.052 Uiso 1 1 calc R U . . .
N1 N -0.11319(12) -0.13491(11) 0.20437(10) 0.0227(3) Uani 1 1 d . . . . .
N2 N -0.34163(15) -0.20222(14) 0.26602(13) 0.0383(4) Uani 1 1 d . . . . .
N3 N 0.76689(13) 0.48234(11) 0.71483(10) 0.0233(3) Uani 1 1 d . . . . .
N4 N 0.97442(14) 0.57799(13) 0.88252(11) 0.0313(3) Uani 1 1 d . . . . .
O1 O -0.14023(10) 0.10315(10) 0.03826(8) 0.0248(2) Uani 1 1 d . . . . .
O2 O -0.15445(10) 0.04596(9) 0.22239(9) 0.0230(2) Uani 1 1 d . . . . .
O3 O 0.05537(10) 0.06181(10) 0.37313(8) 0.0267(2) Uani 1 1 d . . . . .
O4 O 0.66216(11) 0.63992(9) 0.51069(8) 0.0273(2) Uani 1 1 d . . . . .
O5 O 0.87625(11) 0.57705(10) 0.60964(8) 0.0280(3) Uani 1 1 d . . . . .
O6 O 0.93484(11) 0.38110(11) 0.54739(9) 0.0312(3) Uani 1 1 d . . . . .
Cl1 Cl -0.06330(5) -0.33709(4) 0.18144(4) 0.04441(13) Uani 1 1 d . . . . .
Cl2 Cl 0.63671(4) 0.37684(4) 0.83072(3) 0.03770(12) Uani 1 1 d . . . . .
C35 C 0.5980(2) 0.07995(17) 0.57089(16) 0.0396(4) Uani 1 1 d . . . . .
C36 C 0.5217(2) -0.00312(17) 0.60354(15) 0.0388(4) Uani 1 1 d . . . . .
H36 H 0.536072 -0.006645 0.675884 0.047 Uiso 1 1 calc R U . . .
C37 C 0.5744(2) 0.08100(18) 0.46397(16) 0.0418(5) Uani 1 1 d . . . . .
H37 H 0.625124 0.136055 0.437554 0.050 Uiso 1 1 calc R U . . .
C38 C 0.7048(3) 0.1629(2) 0.64623(19) 0.0576(6) Uani 1 1 d . . . . .
H38A H 0.722376 0.231078 0.616145 0.086 Uiso 1 1 calc R U . . .
H38B H 0.783085 0.130290 0.659981 0.086 Uiso 1 1 calc R U . . .
H38C H 0.678445 0.181138 0.711545 0.086 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.5379(19) . ?
C1 C6 1.543(2) . ?
C1 C9 1.543(2) . ?
C1 C2 1.5464(19) . ?
C2 C3 1.5484(19) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C23 1.5324(19) . ?
C3 C4 1.536(2) . ?
C3 C7 1.542(2) . ?
C4 C5 1.534(2) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C10 1.529(2) . ?
C5 C6 1.537(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.537(2) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C10 1.531(2) . ?
C8 C9 1.536(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.394(2) . ?
C11 C16 1.400(2) . ?
C12 C13 1.397(2) . ?
C12 H12 0.9500 . ?
C13 O1 1.3628(17) . ?
C13 C14 1.387(2) . ?
C14 C15 1.390(2) . ?
C14 O2 1.4002(17) . ?
C15 O3 1.3662(18) . ?
C15 C16 1.393(2) . ?
C16 H16 0.9500 . ?
C17 O1 1.4299(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.319(2) . ?
C18 O2 1.3538(18) . ?
C18 C21 1.392(2) . ?
C19 N1 1.330(2) . ?
C19 C20 1.381(2) . ?
C19 Cl1 1.7278(18) . ?
C20 N2 1.327(3) . ?
C20 H20 0.9500 . ?
C21 N2 1.327(2) . ?
C21 H21 0.9500 . ?
C22 O3 1.4288(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.394(2) . ?
C23 C24 1.396(2) . ?
C24 C25 1.394(2) . ?
C24 H24 0.9500 . ?
C25 O4 1.3622(19) . ?
C25 C26 1.387(2) . ?
C26 C27 1.384(2) . ?
C26 O5 1.4002(17) . ?
C27 O6 1.3634(19) . ?
C27 C28 1.399(2) . ?
C28 H28 0.9500 . ?
C29 O4 1.431(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 N3 1.316(2) . ?
C30 O5 1.3520(19) . ?
C30 C33 1.404(2) . ?
C31 N3 1.332(2) . ?
C31 C32 1.373(2) . ?
C31 Cl2 1.7372(17) . ?
C32 N4 1.341(2) . ?
C32 H32 0.9500 . ?
C33 N4 1.321(2) . ?
C33 H33 0.9500 . ?
C34 O6 1.424(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.379(3) . ?
C35 C37 1.394(3) . ?
C35 C38 1.507(3) . ?
C36 C37 1.374(3) 2_656 ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C6 109.73(11) . . ?
C11 C1 C9 112.80(12) . . ?
C6 C1 C9 107.18(12) . . ?
C11 C1 C2 110.52(11) . . ?
C6 C1 C2 108.83(11) . . ?
C9 C1 C2 107.65(11) . . ?
C1 C2 C3 112.29(11) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2AB 109.1 . . ?
C3 C2 H2AB 109.1 . . ?
H2A C2 H2AB 107.9 . . ?
C23 C3 C4 112.75(12) . . ?
C23 C3 C7 110.92(12) . . ?
C4 C3 C7 108.06(12) . . ?
C23 C3 C2 108.13(11) . . ?
C4 C3 C2 107.77(11) . . ?
C7 C3 C2 109.11(11) . . ?
C5 C4 C3 111.00(12) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4AB 109.4 . . ?
C3 C4 H4AB 109.4 . . ?
H4A C4 H4AB 108.0 . . ?
C10 C5 C4 109.11(12) . . ?
C10 C5 C6 109.61(12) . . ?
C4 C5 C6 110.10(12) . . ?
C10 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C5 C6 C1 110.59(12) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6AB 109.5 . . ?
C1 C6 H6AB 109.5 . . ?
H6A C6 H6AB 108.1 . . ?
C8 C7 C3 109.79(12) . . ?
C8 C7 H7A 109.7 . . ?
C3 C7 H7A 109.7 . . ?
C8 C7 H7AB 109.7 . . ?
C3 C7 H7AB 109.7 . . ?
H7A C7 H7AB 108.2 . . ?
C10 C8 C9 109.71(13) . . ?
C10 C8 C7 109.46(13) . . ?
C9 C8 C7 110.05(12) . . ?
C10 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C8 C9 C1 111.18(12) . . ?
C8 C9 H9A 109.4 . . ?
C1 C9 H9A 109.4 . . ?
C8 C9 H9AB 109.4 . . ?
C1 C9 H9AB 109.4 . . ?
H9A C9 H9AB 108.0 . . ?
C5 C10 C8 108.78(12) . . ?
C5 C10 H10A 109.9 . . ?
C8 C10 H10A 109.9 . . ?
C5 C10 H10B 109.9 . . ?
C8 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C16 118.99(13) . . ?
C12 C11 C1 120.98(13) . . ?
C16 C11 C1 119.99(13) . . ?
C11 C12 C13 120.66(14) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
O1 C13 C14 115.29(13) . . ?
O1 C13 C12 125.31(14) . . ?
C14 C13 C12 119.40(13) . . ?
C13 C14 C15 120.85(13) . . ?
C13 C14 O2 119.42(13) . . ?
C15 C14 O2 119.62(13) . . ?
O3 C15 C14 114.78(13) . . ?
O3 C15 C16 125.82(14) . . ?
C14 C15 C16 119.40(14) . . ?
C15 C16 C11 120.68(13) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 O2 120.55(13) . . ?
N1 C18 C21 122.93(15) . . ?
O2 C18 C21 116.52(14) . . ?
N1 C19 C20 123.70(16) . . ?
N1 C19 Cl1 116.70(13) . . ?
C20 C19 Cl1 119.59(13) . . ?
N2 C20 C19 120.36(16) . . ?
N2 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N2 C21 C18 120.86(17) . . ?
N2 C21 H21 119.6 . . ?
C18 C21 H21 119.6 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 119.53(13) . . ?
C28 C23 C3 121.45(13) . . ?
C24 C23 C3 118.96(13) . . ?
C25 C24 C23 120.46(14) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
O4 C25 C26 115.84(13) . . ?
O4 C25 C24 124.78(14) . . ?
C26 C25 C24 119.38(14) . . ?
C27 C26 C25 120.88(14) . . ?
C27 C26 O5 119.25(14) . . ?
C25 C26 O5 119.67(14) . . ?
O6 C27 C26 115.27(14) . . ?
O6 C27 C28 125.01(15) . . ?
C26 C27 C28 119.72(14) . . ?
C23 C28 C27 120.01(15) . . ?
C23 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 O5 120.37(13) . . ?
N3 C30 C33 123.18(15) . . ?
O5 C30 C33 116.44(14) . . ?
N3 C31 C32 124.13(16) . . ?
N3 C31 Cl2 116.37(12) . . ?
C32 C31 Cl2 119.50(13) . . ?
N4 C32 C31 120.28(15) . . ?
N4 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
N4 C33 C30 120.62(16) . . ?
N4 C33 H33 119.7 . . ?
C30 C33 H33 119.7 . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 N1 C19 114.82(14) . . ?
C21 N2 C20 117.33(15) . . ?
C30 N3 C31 114.55(13) . . ?
C33 N4 C32 117.20(14) . . ?
C13 O1 C17 116.74(12) . . ?
C18 O2 C14 117.34(12) . . ?
C15 O3 C22 117.57(12) . . ?
C25 O4 C29 117.20(12) . . ?
C30 O5 C26 118.59(12) . . ?
C27 O6 C34 117.31(13) . . ?
C36 C35 C37 116.5(2) . . ?
C36 C35 C38 121.90(19) . . ?
C37 C35 C38 121.5(2) . . ?
C37 C36 C35 122.88(18) 2_656 . ?
C37 C36 H36 118.6 2_656 . ?
C35 C36 H36 118.6 . . ?
C36 C37 C35 120.59(19) 2_656 . ?
C36 C37 H37 119.7 2_656 . ?
C35 C37 H37 119.7 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

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
C11 C1 C2 C3 178.58(12) . . . . ?
C6 C1 C2 C3 58.02(15) . . . . ?
C9 C1 C2 C3 -57.83(15) . . . . ?
C1 C2 C3 C23 179.28(12) . . . . ?
C1 C2 C3 C4 -58.56(15) . . . . ?
C1 C2 C3 C7 58.54(15) . . . . ?
C23 C3 C4 C5 177.98(11) . . . . ?
C7 C3 C4 C5 -59.06(15) . . . . ?
C2 C3 C4 C5 58.72(15) . . . . ?
C3 C4 C5 C10 60.36(15) . . . . ?
C3 C4 C5 C6 -59.97(16) . . . . ?
C10 C5 C6 C1 -61.50(15) . . . . ?
C4 C5 C6 C1 58.52(16) . . . . ?
C11 C1 C6 C5 -177.91(11) . . . . ?
C9 C1 C6 C5 59.29(15) . . . . ?
C2 C1 C6 C5 -56.86(15) . . . . ?
C23 C3 C7 C8 -176.85(12) . . . . ?
C4 C3 C7 C8 59.09(15) . . . . ?
C2 C3 C7 C8 -57.83(15) . . . . ?
C3 C7 C8 C10 -61.30(15) . . . . ?
C3 C7 C8 C9 59.35(16) . . . . ?
C10 C8 C9 C1 60.19(15) . . . . ?
C7 C8 C9 C1 -60.31(16) . . . . ?
C11 C1 C9 C8 -179.69(12) . . . . ?
C6 C1 C9 C8 -58.81(15) . . . . ?
C2 C1 C9 C8 58.12(15) . . . . ?
C4 C5 C10 C8 -60.37(15) . . . . ?
C6 C5 C10 C8 60.26(15) . . . . ?
C9 C8 C10 C5 -59.49(15) . . . . ?
C7 C8 C10 C5 61.36(15) . . . . ?
C6 C1 C11 C12 -94.12(16) . . . . ?
C9 C1 C11 C12 25.29(19) . . . . ?
C2 C1 C11 C12 145.86(13) . . . . ?
C6 C1 C11 C16 83.54(16) . . . . ?
C9 C1 C11 C16 -157.05(13) . . . . ?
C2 C1 C11 C16 -36.49(18) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
C1 C11 C12 C13 177.19(13) . . . . ?
C11 C12 C13 O1 178.23(14) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
O1 C13 C14 C15 -177.40(13) . . . . ?
C12 C13 C14 C15 1.7(2) . . . . ?
O1 C13 C14 O2 -1.3(2) . . . . ?
C12 C13 C14 O2 177.80(13) . . . . ?
C13 C14 C15 O3 178.69(13) . . . . ?
O2 C14 C15 O3 2.6(2) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
O2 C14 C15 C16 -177.46(13) . . . . ?
O3 C15 C16 C11 -179.97(14) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C1 C11 C16 C15 -176.87(13) . . . . ?
N1 C19 C20 N2 0.6(3) . . . . ?
Cl1 C19 C20 N2 -178.94(14) . . . . ?
N1 C18 C21 N2 0.5(2) . . . . ?
O2 C18 C21 N2 179.88(15) . . . . ?
C4 C3 C23 C28 -3.58(19) . . . . ?
C7 C3 C23 C28 -124.93(14) . . . . ?
C2 C3 C23 C28 115.47(14) . . . . ?
C4 C3 C23 C24 179.21(12) . . . . ?
C7 C3 C23 C24 57.86(17) . . . . ?
C2 C3 C23 C24 -61.74(16) . . . . ?
C28 C23 C24 C25 0.8(2) . . . . ?
C3 C23 C24 C25 178.09(12) . . . . ?
C23 C24 C25 O4 -179.07(13) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
O4 C25 C26 C27 177.80(13) . . . . ?
C24 C25 C26 C27 -1.4(2) . . . . ?
O4 C25 C26 O5 -7.4(2) . . . . ?
C24 C25 C26 O5 173.40(13) . . . . ?
C25 C26 C27 O6 -177.43(13) . . . . ?
O5 C26 C27 O6 7.8(2) . . . . ?
C25 C26 C27 C28 1.8(2) . . . . ?
O5 C26 C27 C28 -172.97(13) . . . . ?
C24 C23 C28 C27 -0.4(2) . . . . ?
C3 C23 C28 C27 -177.57(13) . . . . ?
O6 C27 C28 C23 178.25(14) . . . . ?
C26 C27 C28 C23 -0.9(2) . . . . ?
N3 C31 C32 N4 1.5(3) . . . . ?
Cl2 C31 C32 N4 -177.86(13) . . . . ?
N3 C30 C33 N4 1.2(3) . . . . ?
O5 C30 C33 N4 -179.64(15) . . . . ?
O2 C18 N1 C19 -179.79(13) . . . . ?
C21 C18 N1 C19 -0.5(2) . . . . ?
C20 C19 N1 C18 -0.1(2) . . . . ?
Cl1 C19 N1 C18 179.45(11) . . . . ?
C18 C21 N2 C20 0.0(3) . . . . ?
C19 C20 N2 C21 -0.5(3) . . . . ?
O5 C30 N3 C31 -179.51(14) . . . . ?
C33 C30 N3 C31 -0.4(2) . . . . ?
C32 C31 N3 C30 -0.9(2) . . . . ?
Cl2 C31 N3 C30 178.45(11) . . . . ?
C30 C33 N4 C32 -0.7(2) . . . . ?
C31 C32 N4 C33 -0.6(2) . . . . ?
C14 C13 O1 C17 174.01(13) . . . . ?
C12 C13 O1 C17 -5.0(2) . . . . ?
N1 C18 O2 C14 -7.7(2) . . . . ?
C21 C18 O2 C14 172.99(13) . . . . ?
C13 C14 O2 C18 109.47(15) . . . . ?
C15 C14 O2 C18 -74.35(17) . . . . ?
C14 C15 O3 C22 -169.59(14) . . . . ?
C16 C15 O3 C22 10.4(2) . . . . ?
C26 C25 O4 C29 -174.79(13) . . . . ?
C24 C25 O4 C29 4.4(2) . . . . ?
N3 C30 O5 C26 -19.1(2) . . . . ?
C33 C30 O5 C26 161.75(14) . . . . ?
C27 C26 O5 C30 -79.49(18) . . . . ?
C25 C26 O5 C30 105.63(17) . . . . ?
C26 C27 O6 C34 176.15(14) . . . . ?
C28 C27 O6 C34 -3.1(2) . . . . ?
C37 C35 C36 C37 -0.7(3) . . . 2_656 ?
C38 C35 C36 C37 -178.59(19) . . . 2_656 ?
C36 C35 C37 C36 0.7(3) . . . 2_656 ?
C38 C35 C37 C36 178.58(19) . . . 2_656 ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_Crystal1
_database_code_depnum_ccdc_archive 'CCDC 1842176'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H34 Cl2 N4 O6'
_chemical_formula_weight         665.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   23.5127(11)
_cell_length_b                   7.1104(3)
_cell_length_c                   19.6874(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.636(2)
_cell_angle_gamma                90
_cell_volume                     3118.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      77.97

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.318
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7873
_exptl_absorpt_correction_T_max  0.8735
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            20154
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.968
_diffrn_reflns_theta_max         78.763
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3273
_reflns_number_gt                3022
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+2.4128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.46917(5) 0.26458(16) 0.29338(6) 0.0112(2) Uani 1 1 d . . . . .
C2 C 0.42292(5) 0.13757(16) 0.24017(6) 0.0137(2) Uani 1 1 d . . . . .
H2A H 0.402883 0.056948 0.266685 0.016 Uiso 1 1 calc R U . . .
H2B H 0.391876 0.216619 0.206426 0.016 Uiso 1 1 calc R U . . .
C3 C 0.45313(5) 0.01322(16) 0.19791(6) 0.0152(2) Uani 1 1 d . . . . .
H3 H 0.422090 -0.067841 0.163947 0.018 Uiso 1 1 calc R U . . .
C4 C 0.48331(5) 0.13706(16) 0.15509(6) 0.0135(2) Uani 1 1 d . . . . .
H4A H 0.452659 0.215443 0.120494 0.016 Uiso 1 1 calc R U . . .
H4B H 0.502604 0.056336 0.127782 0.016 Uiso 1 1 calc R U . . .
C5 C 0.500000 0.3855(2) 0.250000 0.0107(3) Uani 1 2 d S T P . .
H5A H 0.530350 0.467526 0.283313 0.013 Uiso 0.5 1 calc R U P . .
H5B H 0.469648 0.467519 0.216686 0.013 Uiso 0.5 1 calc R U P . .
C6 C 0.500000 -0.1118(2) 0.250000 0.0175(3) Uani 1 2 d S T P . .
H6A H 0.480478 -0.193361 0.276807 0.021 Uiso 0.5 1 calc R U P . .
H6B H 0.519524 -0.193356 0.223192 0.021 Uiso 0.5 1 calc R U P . .
C7 C 0.44044(5) 0.40099(16) 0.33303(6) 0.0123(2) Uani 1 1 d . . . . .
C8 C 0.47738(5) 0.52267(16) 0.38414(6) 0.0125(2) Uani 1 1 d . . . . .
H8 H 0.519757 0.510023 0.397585 0.015 Uiso 1 1 calc R U . . .
C9 C 0.45243(5) 0.66219(16) 0.41543(6) 0.0131(2) Uani 1 1 d . . . . .
C10 C 0.39014(5) 0.68093(16) 0.39489(6) 0.0152(2) Uani 1 1 d . . . . .
C11 C 0.35295(5) 0.55696(18) 0.34652(7) 0.0163(2) Uani 1 1 d . . . . .
C12 C 0.37821(5) 0.41635(17) 0.31573(6) 0.0153(2) Uani 1 1 d . . . . .
H12 H 0.352858 0.330443 0.282755 0.018 Uiso 1 1 calc R U . . .
C13 C 0.54792(5) 0.77839(17) 0.48675(6) 0.0161(2) Uani 1 1 d . . . . .
H13A H 0.565245 0.875021 0.522956 0.024 Uiso 1 1 calc R U . . .
H13B H 0.560865 0.800224 0.444777 0.024 Uiso 1 1 calc R U . . .
H13C H 0.561545 0.653978 0.506820 0.024 Uiso 1 1 calc R U . . .
C14 C 0.34693(5) 0.80169(17) 0.47863(6) 0.0153(2) Uani 1 1 d . . . . .
C15 C 0.32753(5) 0.61533(18) 0.55980(7) 0.0183(3) Uani 1 1 d . . . . .
C16 C 0.30266(5) 0.76375(19) 0.58614(7) 0.0190(3) Uani 1 1 d . . . . .
H16 H 0.286105 0.742708 0.623638 0.023 Uiso 1 1 calc R U . . .
C17 C 0.32396(5) 0.95708(18) 0.50536(7) 0.0182(3) Uani 1 1 d . . . . .
H17 H 0.324260 1.077857 0.484841 0.022 Uiso 1 1 calc R U . . .
C18 C 0.25359(6) 0.4421(2) 0.29203(10) 0.0354(4) Uani 1 1 d . . . . .
H18A H 0.212336 0.469088 0.290539 0.053 Uiso 1 1 calc R U . . .
H18B H 0.265993 0.319863 0.314988 0.053 Uiso 1 1 calc R U . . .
H18C H 0.255617 0.439105 0.243093 0.053 Uiso 1 1 calc R U . . .
N1 N 0.35003(5) 0.63127(15) 0.50616(6) 0.0169(2) Uani 1 1 d . . . . .
N2 N 0.30185(5) 0.93663(16) 0.55902(6) 0.0202(2) Uani 1 1 d . . . . .
O1 O 0.48371(4) 0.78711(12) 0.46585(5) 0.01658(19) Uani 1 1 d . . . . .
O2 O 0.36579(4) 0.83320(12) 0.42140(5) 0.01764(19) Uani 1 1 d . . . . .
O3 O 0.29266(4) 0.58516(14) 0.33206(5) 0.0229(2) Uani 1 1 d . . . . .
Cl1 Cl 0.32925(2) 0.39378(5) 0.59705(2) 0.03041(11) 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
C1 C7 1.5307(15) . ?
C1 C2 1.5387(15) . ?
C1 C4 1.5412(15) 2_655 ?
C1 C5 1.5461(13) . ?
C2 C3 1.5352(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C6 1.5280(15) . ?
C3 C4 1.5401(15) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.3967(16) . ?
C7 C8 1.3988(16) . ?
C8 C9 1.3923(16) . ?
C8 H8 0.9500 . ?
C9 O1 1.3596(14) . ?
C9 C10 1.3957(17) . ?
C10 C11 1.3843(17) . ?
C10 O2 1.4012(14) . ?
C11 O3 1.3685(14) . ?
C11 C12 1.3964(17) . ?
C12 H12 0.9500 . ?
C13 O1 1.4336(14) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N1 1.3200(17) . ?
C14 O2 1.3548(15) . ?
C14 C17 1.4040(16) . ?
C15 N1 1.3285(17) . ?
C15 C16 1.3850(18) . ?
C15 Cl1 1.7326(13) . ?
C16 N2 1.3380(18) . ?
C16 H16 0.9500 . ?
C17 N2 1.3260(17) . ?
C17 H17 0.9500 . ?
C18 O3 1.4272(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 112.83(9) . . ?
C7 C1 C4 112.48(9) . 2_655 ?
C2 C1 C4 107.99(9) . 2_655 ?
C7 C1 C5 106.88(9) . . ?
C2 C1 C5 107.73(8) . . ?
C4 C1 C5 108.76(8) 2_655 . ?
C3 C2 C1 110.99(9) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C6 C3 C2 109.32(9) . . ?
C6 C3 C4 109.91(9) . . ?
C2 C3 C4 109.96(9) . . ?
C6 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C3 C4 C1 109.87(9) . 2_655 ?
C3 C4 H4A 109.7 . . ?
C1 C4 H4A 109.7 2_655 . ?
C3 C4 H4B 109.7 . . ?
C1 C4 H4B 109.7 2_655 . ?
H4A C4 H4B 108.2 . . ?
C1 C5 C1 112.40(12) . 2_655 ?
C1 C5 H5A 109.1 . . ?
C1 C5 H5A 109.1 2_655 . ?
C1 C5 H5B 109.1 . . ?
C1 C5 H5B 109.1 2_655 . ?
H5A C5 H5B 107.9 . . ?
C3 C6 C3 108.82(13) 2_655 . ?
C3 C6 H6A 109.9 2_655 . ?
C3 C6 H6A 109.9 . . ?
C3 C6 H6B 109.9 2_655 . ?
C3 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C12 C7 C8 119.23(10) . . ?
C12 C7 C1 121.59(10) . . ?
C8 C7 C1 119.01(10) . . ?
C9 C8 C7 120.43(10) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
O1 C9 C8 125.62(11) . . ?
O1 C9 C10 114.95(10) . . ?
C8 C9 C10 119.43(11) . . ?
C11 C10 C9 120.81(11) . . ?
C11 C10 O2 120.31(11) . . ?
C9 C10 O2 118.80(10) . . ?
O3 C11 C10 115.75(11) . . ?
O3 C11 C12 124.79(11) . . ?
C10 C11 C12 119.45(11) . . ?
C11 C12 C7 120.53(11) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 O2 120.24(10) . . ?
N1 C14 C17 123.08(11) . . ?
O2 C14 C17 116.68(11) . . ?
N1 C15 C16 123.75(12) . . ?
N1 C15 Cl1 116.91(9) . . ?
C16 C15 Cl1 119.33(10) . . ?
N2 C16 C15 120.29(12) . . ?
N2 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N2 C17 C14 120.53(12) . . ?
N2 C17 H17 119.7 . . ?
C14 C17 H17 119.7 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 N1 C15 114.90(10) . . ?
C17 N2 C16 117.36(11) . . ?
C9 O1 C13 117.11(9) . . ?
C14 O2 C10 117.60(9) . . ?
C11 O3 C18 116.85(10) . . ?

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
C7 C1 C2 C3 175.98(9) . . . . ?
C4 C1 C2 C3 -59.07(12) 2_655 . . . ?
C5 C1 C2 C3 58.25(12) . . . . ?
C1 C2 C3 C6 60.40(12) . . . . ?
C1 C2 C3 C4 -60.34(12) . . . . ?
C6 C3 C4 C1 -60.84(12) . . . 2_655 ?
C2 C3 C4 C1 59.55(12) . . . 2_655 ?
C7 C1 C5 C1 -179.68(9) . . . 2_655 ?
C2 C1 C5 C1 -58.17(7) . . . 2_655 ?
C4 C1 C5 C1 58.65(7) 2_655 . . 2_655 ?
C2 C3 C6 C3 -60.02(7) . . . 2_655 ?
C4 C3 C6 C3 60.75(7) . . . 2_655 ?
C2 C1 C7 C12 -5.93(15) . . . . ?
C4 C1 C7 C12 -128.40(11) 2_655 . . . ?
C5 C1 C7 C12 112.30(11) . . . . ?
C2 C1 C7 C8 178.81(10) . . . . ?
C4 C1 C7 C8 56.34(13) 2_655 . . . ?
C5 C1 C7 C8 -62.96(12) . . . . ?
C12 C7 C8 C9 -2.43(17) . . . . ?
C1 C7 C8 C9 172.94(10) . . . . ?
C7 C8 C9 O1 179.49(10) . . . . ?
C7 C8 C9 C10 -0.59(17) . . . . ?
O1 C9 C10 C11 -176.89(10) . . . . ?
C8 C9 C10 C11 3.18(18) . . . . ?
O1 C9 C10 O2 6.19(16) . . . . ?
C8 C9 C10 O2 -173.74(10) . . . . ?
C9 C10 C11 O3 177.99(11) . . . . ?
O2 C10 C11 O3 -5.14(17) . . . . ?
C9 C10 C11 C12 -2.67(18) . . . . ?
O2 C10 C11 C12 174.20(11) . . . . ?
O3 C11 C12 C7 178.85(11) . . . . ?
C10 C11 C12 C7 -0.42(18) . . . . ?
C8 C7 C12 C11 2.95(17) . . . . ?
C1 C7 C12 C11 -172.30(11) . . . . ?
N1 C15 C16 N2 -2.02(19) . . . . ?
Cl1 C15 C16 N2 178.79(9) . . . . ?
N1 C14 C17 N2 -2.59(18) . . . . ?
O2 C14 C17 N2 176.71(11) . . . . ?
O2 C14 N1 C15 -176.79(10) . . . . ?
C17 C14 N1 C15 2.49(17) . . . . ?
C16 C15 N1 C14 -0.25(18) . . . . ?
Cl1 C15 N1 C14 178.96(9) . . . . ?
C14 C17 N2 C16 0.20(17) . . . . ?
C15 C16 N2 C17 1.93(18) . . . . ?
C8 C9 O1 C13 2.26(16) . . . . ?
C10 C9 O1 C13 -177.66(10) . . . . ?
N1 C14 O2 C10 -2.09(16) . . . . ?
C17 C14 O2 C10 178.58(10) . . . . ?
C11 C10 O2 C14 84.76(14) . . . . ?
C9 C10 O2 C14 -98.30(13) . . . . ?
C10 C11 O3 C18 -169.87(13) . . . . ?
C12 C11 O3 C18 10.83(19) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.058

