# Electronic Supplementary Material (ESI) for ChemComm.
# 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_save_a
_database_code_depnum_ccdc_archive 'CCDC 1841283'
_audit_update_record             
;
2018-05-03 deposited with the CCDC.
2018-07-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT973_save_a              
;
PROBLEM: Check Calcd Positive Resid. Density on       Ce1       1.69 eA-3  
RESPONSE: This is due to the thermal motion of the heavy cerium atom
;
# end Validation Reply Form

_audit_creation_date             2018-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C56 H64 Ce N8 O4, 2(C H2 Cl2)'
_chemical_formula_sum            'C58 H68 Ce Cl4 N8 O4'
_chemical_formula_weight         1223.12
_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'
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'
Ce Ce -0.2486 2.6331 '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 2/c'
_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                   15.120(6)
_cell_length_b                   25.007(9)
_cell_length_c                   15.405(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.137(9)
_cell_angle_gamma                90
_cell_volume                     5801(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9808
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            54963
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         2.101
_diffrn_ambient_temperature      299.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7182
_reflns_number_total             8839
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.169
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         8839
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+3.8070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_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
2. Rigid bond restraints
 N4, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
N4 \\sim C20: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B), C7(H7A,H7B), C9(H9A,H9B), C29(H29A,H29B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C17(H17), C11(H11), C14(H14), C3(H3), C27(H27), C22(H22), C15(H15),
 C24(H24), C4(H4), C25(H25), C26(H26)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C21(H21A,H21B,H21C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Ce1 Ce 0.000000 0.28352(2) 0.250000 0.02442(6) Uani 1 2 d S T P . .
O2 O 0.08338(11) 0.27201(6) 0.37610(10) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.08422(11) 0.21947(6) 0.19751(10) 0.0341(3) Uani 1 1 d . . . . .
N2 N 0.09402(12) 0.36921(7) 0.28595(11) 0.0308(4) Uani 1 1 d . . . . .
N1 N 0.08879(12) 0.32423(7) 0.13107(11) 0.0319(4) Uani 1 1 d . . . . .
C1 C 0.10672(14) 0.20431(9) 0.12066(14) 0.0311(5) Uani 1 1 d . . . . .
C12 C 0.10598(14) 0.30024(9) 0.44717(14) 0.0324(5) Uani 1 1 d . . . . .
C6 C 0.11806(15) 0.15011(9) 0.10233(15) 0.0360(5) Uani 1 1 d . . . . .
H6 H 0.111327 0.125244 0.146144 0.043 Uiso 1 1 calc R . . . .
C2 C 0.12181(16) 0.24258(9) 0.05464(14) 0.0362(5) Uani 1 1 d . . . . .
C13 C 0.12919(15) 0.35527(9) 0.44129(14) 0.0341(5) Uani 1 1 d . . . . .
C17 C 0.11000(17) 0.27594(10) 0.52906(15) 0.0412(6) Uani 1 1 d . . . . .
H17 H 0.095127 0.239971 0.532642 0.049 Uiso 1 1 calc R . . . .
N3 N 0.14486(16) 0.07813(9) 0.00235(15) 0.0531(6) Uani 1 1 d . . . . .
C11 C 0.11803(17) 0.29869(9) 0.06643(15) 0.0374(5) Uani 1 1 d . . . . .
H11 H 0.138964 0.319555 0.022684 0.045 Uiso 1 1 calc R . . . .
C28 C 0.09310(15) 0.38089(9) 0.13161(14) 0.0341(5) Uani 1 1 d . . . . .
C14 C 0.15689(17) 0.38227(10) 0.51946(15) 0.0434(6) Uani 1 1 d . . . . .
H14 H 0.174349 0.417829 0.516446 0.052 Uiso 1 1 calc R . . . .
C5 C 0.13913(16) 0.13160(10) 0.02076(16) 0.0410(5) Uani 1 1 d . . . . .
C23 C 0.09819(15) 0.40469(8) 0.21401(15) 0.0338(5) Uani 1 1 d . . . . .
C3 C 0.1473(2) 0.22311(10) -0.02496(18) 0.0511(7) Uani 1 1 d . . . . .
H3 H 0.159740 0.247737 -0.067455 0.061 Uiso 1 1 calc R . . . .
C27 C 0.08882(18) 0.41289(10) 0.05708(16) 0.0455(6) Uani 1 1 d . . . . .
H27 H 0.083494 0.397189 0.002132 0.055 Uiso 1 1 calc R . . . .
C22 C 0.12816(15) 0.38405(9) 0.36210(14) 0.0357(5) Uani 1 1 d . . . . .
H22 H 0.155163 0.417491 0.365194 0.043 Uiso 1 1 calc R . . . .
C15 C 0.15915(18) 0.35849(11) 0.59902(16) 0.0474(6) Uani 1 1 d . . . . .
H15 H 0.176176 0.378188 0.648946 0.057 Uiso 1 1 calc R . . . .
C16 C 0.13582(16) 0.30407(11) 0.60635(15) 0.0424(6) Uani 1 1 d . . . . .
N4 N 0.13855(18) 0.28063(10) 0.68701(14) 0.0575(6) Uani 1 1 d . U . . .
C24 C 0.10137(18) 0.46049(9) 0.22056(18) 0.0479(6) Uani 1 1 d . . . . .
H24 H 0.105027 0.476777 0.275042 0.057 Uiso 1 1 calc R . . . .
C4 C 0.15487(19) 0.17008(11) -0.04322(17) 0.0510(7) Uani 1 1 d . . . . .
H4 H 0.170326 0.159251 -0.097607 0.061 Uiso 1 1 calc R . . . .
C25 C 0.0991(2) 0.49142(10) 0.1459(2) 0.0573(7) Uani 1 1 d . . . . .
H25 H 0.101979 0.528466 0.150552 0.069 Uiso 1 1 calc R . . . .
C18 C 0.1820(2) 0.30692(15) 0.76422(16) 0.0617(8) Uani 1 1 d . . . . .
H18A H 0.230415 0.328785 0.746944 0.074 Uiso 1 1 calc R . . . .
H18B H 0.207141 0.279845 0.804241 0.074 Uiso 1 1 calc R . . . .
C20 C 0.1131(2) 0.22455(12) 0.69911(19) 0.0585(7) Uani 1 1 d . U . . .
H20A H 0.067107 0.214605 0.654070 0.070 Uiso 1 1 calc R . . . .
H20B H 0.089207 0.220590 0.755120 0.070 Uiso 1 1 calc R . . . .
C26 C 0.0925(2) 0.46795(11) 0.06500(19) 0.0559(7) Uani 1 1 d . . . . .
H26 H 0.090508 0.489182 0.015304 0.067 Uiso 1 1 calc R . . . .
C7 C 0.1626(2) 0.05907(12) -0.0843(2) 0.0629(8) Uani 1 1 d . . . . .
H7A H 0.184961 0.022744 -0.079429 0.075 Uiso 1 1 calc R . . . .
H7B H 0.208346 0.081189 -0.106174 0.075 Uiso 1 1 calc R . . . .
C9 C 0.1245(2) 0.03721(11) 0.0648(2) 0.0673(9) Uani 1 1 d . . . . .
H9A H 0.099145 0.006411 0.033399 0.081 Uiso 1 1 calc R . . . .
H9B H 0.080418 0.050980 0.100941 0.081 Uiso 1 1 calc R . . . .
C8 C 0.0809(3) 0.06017(15) -0.1489(2) 0.0844(11) Uani 1 1 d . . . . .
H8A H 0.096952 0.049594 -0.205316 0.127 Uiso 1 1 calc GR . . . .
H8B H 0.056880 0.095713 -0.152120 0.127 Uiso 1 1 calc GR . . . .
H8C H 0.037253 0.035892 -0.130217 0.127 Uiso 1 1 calc GR . . . .
C21 C 0.1904(3) 0.18850(17) 0.6952(3) 0.0893(12) Uani 1 1 d . . . . .
H21A H 0.213015 0.191611 0.639114 0.134 Uiso 1 1 calc GR . . . .
H21B H 0.172344 0.152252 0.704046 0.134 Uiso 1 1 calc GR . . . .
H21C H 0.235930 0.198278 0.739802 0.134 Uiso 1 1 calc GR . . . .
C10 C 0.2051(3) 0.01975(17) 0.1223(3) 0.1063(15) Uani 1 1 d . . . . .
H10A H 0.248337 0.005049 0.087009 0.160 Uiso 1 1 calc GR . . . .
H10B H 0.188237 -0.006906 0.162521 0.160 Uiso 1 1 calc GR . . . .
H10C H 0.230159 0.049990 0.154100 0.160 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.39983(7) 0.38138(4) 0.50134(7) 0.0940(3) Uani 1 1 d . . . . .
Cl2 Cl 0.37889(9) 0.41643(4) 0.67556(7) 0.1051(4) Uani 1 1 d . . . . .
C19 C 0.1193(3) 0.34180(16) 0.8110(2) 0.0838(11) Uani 1 1 d . . . . .
H19A H 0.094109 0.368707 0.771814 0.126 Uiso 1 1 calc GR . . . .
H19B H 0.151478 0.358657 0.860189 0.126 Uiso 1 1 calc GR . . . .
H19C H 0.072660 0.320126 0.830732 0.126 Uiso 1 1 calc GR . . . .
C29 C 0.3898(2) 0.36129(13) 0.6093(3) 0.0768(11) Uani 1 1 d . . . . .
H29A H 0.338205 0.338361 0.611080 0.092 Uiso 1 1 calc R . . . .
H29B H 0.441855 0.340947 0.630613 0.092 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ce1 O2 2.2377(16) 2 ?
Ce1 O2 2.2377(16) . ?
Ce1 O1 2.2417(15) . ?
Ce1 O1 2.2418(15) 2 ?
Ce1 N2 2.6033(18) . ?
Ce1 N2 2.6032(18) 2 ?
Ce1 N1 2.5760(19) . ?
Ce1 N1 2.5760(19) 2 ?
O2 C12 1.322(3) . ?
O1 C1 1.316(3) . ?
N2 C23 1.426(3) . ?
N2 C22 1.293(3) . ?
N1 C11 1.294(3) . ?
N1 C28 1.418(3) . ?
C1 C6 1.398(3) . ?
C1 C2 1.430(3) . ?
C12 C13 1.425(3) . ?
C12 C17 1.397(3) . ?
C6 C5 1.402(3) . ?
C2 C11 1.417(3) . ?
C2 C3 1.405(3) . ?
C13 C14 1.411(3) . ?
C13 C22 1.415(3) . ?
C17 C16 1.408(3) . ?
N3 C5 1.371(3) . ?
N3 C7 1.464(3) . ?
N3 C9 1.456(4) . ?
C28 C23 1.398(3) . ?
C28 C27 1.396(3) . ?
C14 C15 1.360(3) . ?
C5 C4 1.413(4) . ?
C23 C24 1.400(3) . ?
C3 C4 1.363(3) . ?
C27 C26 1.383(4) . ?
C15 C16 1.413(4) . ?
C16 N4 1.371(3) . ?
N4 C18 1.462(3) . ?
N4 C20 1.470(4) . ?
C24 C25 1.384(4) . ?
C25 C26 1.373(4) . ?
C18 C19 1.517(5) . ?
C20 C21 1.481(5) . ?
C7 C8 1.515(5) . ?
C9 C10 1.506(5) . ?
Cl1 C29 1.756(4) . ?
Cl2 C29 1.732(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
O2 Ce1 O2 165.21(8) 2 . ?
O2 Ce1 O1 85.82(6) . . ?
O2 Ce1 O1 83.62(6) . 2 ?
O2 Ce1 O1 83.62(6) 2 . ?
O2 Ce1 O1 85.82(6) 2 2 ?
O2 Ce1 N2 123.03(5) 2 . ?
O2 Ce1 N2 123.03(5) . 2 ?
O2 Ce1 N2 70.54(6) 2 2 ?
O2 Ce1 N2 70.54(6) . . ?
O2 Ce1 N1 73.88(6) . 2 ?
O2 Ce1 N1 112.29(6) . . ?
O2 Ce1 N1 73.88(6) 2 . ?
O2 Ce1 N1 112.29(6) 2 2 ?
O1 Ce1 O1 88.79(8) . 2 ?
O1 Ce1 N2 145.93(6) . 2 ?
O1 Ce1 N2 110.36(6) . . ?
O1 Ce1 N2 145.93(6) 2 . ?
O1 Ce1 N2 110.36(6) 2 2 ?
O1 Ce1 N1 71.14(6) . . ?
O1 Ce1 N1 152.61(6) 2 . ?
O1 Ce1 N1 71.14(6) 2 2 ?
O1 Ce1 N1 152.62(6) . 2 ?
N2 Ce1 N2 69.22(8) 2 . ?
N1 Ce1 N2 80.38(6) 2 . ?
N1 Ce1 N2 80.38(6) . 2 ?
N1 Ce1 N2 61.10(6) . . ?
N1 Ce1 N2 61.09(6) 2 2 ?
N1 Ce1 N1 133.45(8) . 2 ?
C12 O2 Ce1 137.23(14) . . ?
C1 O1 Ce1 136.97(13) . . ?
C23 N2 Ce1 114.10(13) . . ?
C22 N2 Ce1 126.53(14) . . ?
C22 N2 C23 119.00(18) . . ?
C11 N1 Ce1 126.02(15) . . ?
C11 N1 C28 118.62(19) . . ?
C28 N1 Ce1 114.65(14) . . ?
O1 C1 C6 120.5(2) . . ?
O1 C1 C2 121.2(2) . . ?
C6 C1 C2 118.4(2) . . ?
O2 C12 C13 120.7(2) . . ?
O2 C12 C17 120.2(2) . . ?
C17 C12 C13 119.1(2) . . ?
C1 C6 C5 122.9(2) . . ?
C11 C2 C1 124.1(2) . . ?
C3 C2 C1 117.6(2) . . ?
C3 C2 C11 118.2(2) . . ?
C14 C13 C12 117.6(2) . . ?
C14 C13 C22 118.2(2) . . ?
C22 C13 C12 124.2(2) . . ?
C12 C17 C16 122.2(2) . . ?
C5 N3 C7 121.7(2) . . ?
C5 N3 C9 121.9(2) . . ?
C9 N3 C7 116.1(2) . . ?
N1 C11 C2 127.5(2) . . ?
C23 C28 N1 115.44(19) . . ?
C27 C28 N1 124.7(2) . . ?
C27 C28 C23 119.8(2) . . ?
C15 C14 C13 122.8(2) . . ?
C6 C5 C4 117.8(2) . . ?
N3 C5 C6 122.1(2) . . ?
N3 C5 C4 120.1(2) . . ?
C28 C23 N2 115.98(19) . . ?
C28 C23 C24 119.3(2) . . ?
C24 C23 N2 124.6(2) . . ?
C4 C3 C2 123.5(2) . . ?
C26 C27 C28 120.0(2) . . ?
N2 C22 C13 127.5(2) . . ?
C14 C15 C16 120.5(2) . . ?
C17 C16 C15 117.8(2) . . ?
N4 C16 C17 122.4(2) . . ?
N4 C16 C15 119.8(2) . . ?
C16 N4 C18 121.3(2) . . ?
C16 N4 C20 122.4(2) . . ?
C18 N4 C20 115.4(2) . . ?
C25 C24 C23 119.9(2) . . ?
C3 C4 C5 119.8(2) . . ?
C26 C25 C24 120.7(2) . . ?
N4 C18 C19 113.0(3) . . ?
N4 C20 C21 111.0(3) . . ?
C25 C26 C27 120.3(2) . . ?
N3 C7 C8 112.9(3) . . ?
N3 C9 C10 112.7(3) . . ?
Cl2 C29 Cl1 110.56(17) . . ?

_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_test
_database_code_depnum_ccdc_archive 'CCDC 1841285'
_audit_update_record             
;
2018-05-03 deposited with the CCDC.
2018-07-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT971_test                
;
PROBLEM: Check Calcd Resid. Dens.  0.98A   From Pu1             2.78 eA-3  
RESPONSE: This is due to the thermal motion of the heavy plutonium atom
;
# end Validation Reply Form


_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            'C58 H68 Cl4 N8 O4 Pu'
_chemical_formula_weight         1325.00

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'
Pu Pu -9.4100 4.3056 '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                   15.0632(9)
_cell_length_b                   24.9196(15)
_cell_length_c                   15.3540(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.012(2)
_cell_angle_gamma                90
_cell_volume                     5741.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9750
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      30.40

_exptl_crystal_description       irregular
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             2664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.387
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6146
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69626
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.108
_diffrn_reflns_theta_max         30.625
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8836
_reflns_number_gt                7136
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+36.3036P] 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         8836
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.003
_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
Pu1 Pu 0.500000 0.71536(2) 0.250000 0.02070(6) Uani 1 2 d S T P . .
Cl1 Cl 0.59968(14) 0.88196(8) 0.49759(14) 0.0884(6) Uani 1 1 d . . . . .
Cl2 Cl 0.62222(18) 0.91688(8) 0.32367(14) 0.1007(7) Uani 1 1 d . . . . .
O1 O 0.58306(19) 0.72835(11) 0.37529(17) 0.0280(6) Uani 1 1 d . . . . .
O2 O 0.58334(18) 0.77970(11) 0.19844(16) 0.0266(6) Uani 1 1 d . . . . .
N1 N 0.5931(2) 0.63050(12) 0.2866(2) 0.0242(7) Uani 1 1 d . . . . .
N2 N 0.5874(2) 0.67506(13) 0.1320(2) 0.0254(7) Uani 1 1 d . . . . .
N3 N 0.6384(3) 0.72071(19) 0.6866(2) 0.0507(11) Uani 1 1 d . U . . .
N4 N 0.6445(3) 0.92146(16) 0.0034(3) 0.0473(11) Uani 1 1 d . . . . .
C1 C 0.6054(3) 0.70057(16) 0.4469(3) 0.0261(8) Uani 1 1 d . . . . .
C2 C 0.6289(3) 0.64521(17) 0.4419(3) 0.0279(8) Uani 1 1 d . . . . .
C3 C 0.6564(3) 0.61877(19) 0.5199(3) 0.0372(10) Uani 1 1 d . . . . .
H3 H 0.673359 0.582980 0.516955 0.045 Uiso 1 1 calc R U . . .
C4 C 0.6596(3) 0.6424(2) 0.5993(3) 0.0418(11) Uani 1 1 d . . . . .
H4 H 0.677326 0.622844 0.649403 0.050 Uiso 1 1 calc R U . . .
C5 C 0.6358(3) 0.6971(2) 0.6057(3) 0.0379(11) Uani 1 1 d . . . . .
C6 C 0.6097(3) 0.72462(19) 0.5287(3) 0.0346(10) Uani 1 1 d . . . . .
H6 H 0.594433 0.760670 0.532200 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6818(4) 0.6945(3) 0.7641(3) 0.0574(16) Uani 1 1 d . . . . .
H7A H 0.707125 0.721696 0.804097 0.069 Uiso 1 1 calc R U . . .
H7B H 0.730219 0.672323 0.746922 0.069 Uiso 1 1 calc R U . . .
C8 C 0.6184(5) 0.6603(3) 0.8103(4) 0.079(2) Uani 1 1 d . . . . .
H8A H 0.595173 0.632328 0.771781 0.119 Uiso 1 1 calc R U . . .
H8B H 0.570282 0.682042 0.827292 0.119 Uiso 1 1 calc R U . . .
H8C H 0.649440 0.644591 0.861379 0.119 Uiso 1 1 calc R U . . .
C9 C 0.6125(4) 0.7771(3) 0.6981(3) 0.0566(15) Uani 1 1 d . U . . .
H9A H 0.566377 0.786838 0.652805 0.068 Uiso 1 1 calc R U . . .
H9B H 0.588293 0.781277 0.754251 0.068 Uiso 1 1 calc R U . . .
C10 C 0.6893(5) 0.8131(3) 0.6938(5) 0.087(2) Uani 1 1 d . . . . .
H10A H 0.710916 0.810706 0.636960 0.131 Uiso 1 1 calc R U . . .
H10B H 0.735784 0.802714 0.737407 0.131 Uiso 1 1 calc R U . . .
H10C H 0.671536 0.849335 0.704388 0.131 Uiso 1 1 calc R U . . .
C11 C 0.6274(3) 0.61571(16) 0.3633(3) 0.0295(9) Uani 1 1 d . . . . .
H11 H 0.654035 0.582013 0.366818 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6057(2) 0.79493(16) 0.1214(2) 0.0253(8) Uani 1 1 d . . . . .
C13 C 0.6212(3) 0.75687(17) 0.0558(3) 0.0305(9) Uani 1 1 d . . . . .
C14 C 0.6473(4) 0.7764(2) -0.0241(3) 0.0448(12) Uani 1 1 d . . . . .
H14 H 0.660009 0.751759 -0.066757 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6549(4) 0.8293(2) -0.0420(3) 0.0468(13) Uani 1 1 d . . . . .
H15 H 0.670685 0.840106 -0.096565 0.056 Uiso 1 1 calc R U . . .
C16 C 0.6392(3) 0.86792(18) 0.0214(3) 0.0346(10) Uani 1 1 d . . . . .
C17 C 0.6175(3) 0.84940(17) 0.1034(3) 0.0314(9) Uani 1 1 d . . . . .
H17 H 0.610674 0.874319 0.147443 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6626(4) 0.9403(2) -0.0835(4) 0.0577(15) Uani 1 1 d . . . . .
H18A H 0.708181 0.917710 -0.105445 0.069 Uiso 1 1 calc R U . . .
H18B H 0.685741 0.976564 -0.078823 0.069 Uiso 1 1 calc R U . . .
C19 C 0.5815(5) 0.9396(3) -0.1478(4) 0.078(2) Uani 1 1 d . . . . .
H19A H 0.596583 0.953487 -0.202882 0.118 Uiso 1 1 calc R U . . .
H19B H 0.535758 0.961440 -0.126092 0.118 Uiso 1 1 calc R U . . .
H19C H 0.560273 0.903423 -0.155366 0.118 Uiso 1 1 calc R U . . .
C20 C 0.6247(4) 0.9623(2) 0.0654(4) 0.0603(16) Uani 1 1 d . . . . .
H20A H 0.580334 0.948697 0.101910 0.072 Uiso 1 1 calc R U . . .
H20B H 0.599354 0.993240 0.033866 0.072 Uiso 1 1 calc R U . . .
C21 C 0.7054(6) 0.9796(3) 0.1224(5) 0.101(3) Uani 1 1 d . . . . .
H21A H 0.750227 0.992038 0.086552 0.151 Uiso 1 1 calc R U . . .
H21B H 0.728088 0.949748 0.157080 0.151 Uiso 1 1 calc R U . . .
H21C H 0.689465 1.008065 0.160222 0.151 Uiso 1 1 calc R U . . .
C22 C 0.6174(3) 0.70061(17) 0.0670(3) 0.0310(9) Uani 1 1 d . . . . .
H22 H 0.638746 0.679710 0.023156 0.037 Uiso 1 1 calc R U . . .
C23 C 0.5926(3) 0.61859(16) 0.1324(3) 0.0258(8) Uani 1 1 d . . . . .
C24 C 0.5885(3) 0.58595(18) 0.0584(3) 0.0403(11) Uani 1 1 d . . . . .
H24 H 0.582544 0.601434 0.003081 0.048 Uiso 1 1 calc R U . . .
C25 C 0.5930(4) 0.5312(2) 0.0666(3) 0.0498(13) Uani 1 1 d . . . . .
H25 H 0.591570 0.509855 0.016744 0.060 Uiso 1 1 calc R U . . .
C26 C 0.5997(4) 0.50740(19) 0.1480(4) 0.0523(14) Uani 1 1 d . . . . .
H26 H 0.603027 0.470246 0.152929 0.063 Uiso 1 1 calc R U . . .
C27 C 0.6015(3) 0.53906(18) 0.2225(3) 0.0417(11) Uani 1 1 d . . . . .
H27 H 0.605132 0.522999 0.277378 0.050 Uiso 1 1 calc R U . . .
C28 C 0.5978(3) 0.59483(16) 0.2155(3) 0.0266(8) Uani 1 1 d . . . . .
C29 C 0.6104(4) 0.8619(2) 0.3904(5) 0.0705(19) Uani 1 1 d . . . . .
H00A H 0.662027 0.838731 0.388984 0.085 Uiso 1 1 calc R U . . .
H00B H 0.558134 0.841561 0.368837 0.085 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
Pu1 O2 2.224(3) 2_655 ?
Pu1 O2 2.224(3) . ?
Pu1 O1 2.225(3) 2_655 ?
Pu1 O1 2.225(3) . ?
Pu1 N2 2.538(3) 2_655 ?
Pu1 N2 2.538(3) . ?
Pu1 N1 2.572(3) 2_655 ?
Pu1 N1 2.572(3) . ?
Cl1 C29 1.741(7) . ?
Cl2 C29 1.730(7) . ?
O1 C1 1.318(5) . ?
O2 C12 1.313(4) . ?
N1 C11 1.298(5) . ?
N1 C28 1.414(5) . ?
N2 C22 1.298(5) . ?
N2 C23 1.409(5) . ?
N3 C5 1.371(6) . ?
N3 C7 1.460(6) . ?
N3 C9 1.474(7) . ?
N4 C16 1.366(6) . ?
N4 C20 1.442(7) . ?
N4 C18 1.463(6) . ?
C1 C6 1.388(5) . ?
C1 C2 1.428(6) . ?
C2 C3 1.397(5) . ?
C2 C11 1.413(6) . ?
C3 C4 1.351(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.504(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.470(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C12 C17 1.400(6) . ?
C12 C13 1.418(6) . ?
C13 C14 1.409(6) . ?
C13 C22 1.414(6) . ?
C14 C15 1.352(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.405(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.406(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.502(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.498(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?
C23 C24 1.394(6) . ?
C23 C28 1.402(6) . ?
C24 C25 1.372(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.389(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.395(6) . ?
C27 H27 0.9300 . ?
C29 H00A 0.9700 . ?
C29 H00B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Pu1 O2 87.75(14) 2_655 . ?
O2 Pu1 O1 84.87(10) 2_655 2_655 ?
O2 Pu1 O1 83.08(10) . 2_655 ?
O2 Pu1 O1 83.09(10) 2_655 . ?
O2 Pu1 O1 84.87(10) . . ?
O1 Pu1 O1 163.27(14) 2_655 . ?
O2 Pu1 N2 71.77(10) 2_655 2_655 ?
O2 Pu1 N2 152.05(10) . 2_655 ?
O1 Pu1 N2 112.80(11) 2_655 2_655 ?
O1 Pu1 N2 74.19(10) . 2_655 ?
O2 Pu1 N2 152.05(10) 2_655 . ?
O2 Pu1 N2 71.76(10) . . ?
O1 Pu1 N2 74.20(10) 2_655 . ?
O1 Pu1 N2 112.80(11) . . ?
N2 Pu1 N2 133.38(14) 2_655 . ?
O2 Pu1 N1 110.89(10) 2_655 2_655 ?
O2 Pu1 N1 145.97(10) . 2_655 ?
O1 Pu1 N1 71.11(10) 2_655 2_655 ?
O1 Pu1 N1 124.27(10) . 2_655 ?
N2 Pu1 N1 61.57(10) 2_655 2_655 ?
N2 Pu1 N1 79.95(10) . 2_655 ?
O2 Pu1 N1 145.98(10) 2_655 . ?
O2 Pu1 N1 110.89(10) . . ?
O1 Pu1 N1 124.27(10) 2_655 . ?
O1 Pu1 N1 71.11(10) . . ?
N2 Pu1 N1 79.95(10) 2_655 . ?
N2 Pu1 N1 61.57(10) . . ?
N1 Pu1 N1 69.39(14) 2_655 . ?
C1 O1 Pu1 136.7(2) . . ?
C12 O2 Pu1 136.5(2) . . ?
C11 N1 C28 118.6(3) . . ?
C11 N1 Pu1 126.7(3) . . ?
C28 N1 Pu1 114.3(2) . . ?
C22 N2 C23 118.0(3) . . ?
C22 N2 Pu1 126.3(3) . . ?
C23 N2 Pu1 115.1(2) . . ?
C5 N3 C7 121.4(5) . . ?
C5 N3 C9 122.1(4) . . ?
C7 N3 C9 115.7(4) . . ?
C16 N4 C20 122.5(4) . . ?
C16 N4 C18 121.1(4) . . ?
C20 N4 C18 116.2(4) . . ?
O1 C1 C6 121.1(4) . . ?
O1 C1 C2 120.6(3) . . ?
C6 C1 C2 118.2(4) . . ?
C3 C2 C11 117.9(4) . . ?
C3 C2 C1 117.8(4) . . ?
C11 C2 C1 124.3(4) . . ?
C4 C3 C2 123.5(4) . . ?
C4 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N3 C5 C6 122.8(5) . . ?
N3 C5 C4 119.3(4) . . ?
C6 C5 C4 117.9(4) . . ?
C1 C6 C5 122.9(4) . . ?
C1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
N3 C7 C8 112.4(5) . . ?
N3 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N3 111.0(5) . . ?
C10 C9 H9A 109.4 . . ?
N3 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N3 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C2 127.1(4) . . ?
N1 C11 H11 116.4 . . ?
C2 C11 H11 116.4 . . ?
O2 C12 C17 120.3(4) . . ?
O2 C12 C13 121.2(4) . . ?
C17 C12 C13 118.5(4) . . ?
C14 C13 C22 117.8(4) . . ?
C14 C13 C12 117.6(4) . . ?
C22 C13 C12 124.5(4) . . ?
C15 C14 C13 123.3(4) . . ?
C15 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
N4 C16 C15 120.8(4) . . ?
N4 C16 C17 121.6(4) . . ?
C15 C16 C17 117.6(4) . . ?
C12 C17 C16 122.6(4) . . ?
C12 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
N4 C18 C19 113.0(5) . . ?
N4 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N4 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 C21 112.6(6) . . ?
N4 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
N4 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C13 126.9(4) . . ?
N2 C22 H22 116.6 . . ?
C13 C22 H22 116.6 . . ?
C24 C23 C28 119.4(4) . . ?
C24 C23 N2 125.4(4) . . ?
C28 C23 N2 115.1(3) . . ?
C25 C24 C23 120.5(5) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.6(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C27 119.9(4) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.3(5) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 119.3(4) . . ?
C27 C28 N1 124.8(4) . . ?
C23 C28 N1 115.7(3) . . ?
Cl2 C29 Cl1 110.8(3) . . ?
Cl2 C29 H00A 109.5 . . ?
Cl1 C29 H00A 109.5 . . ?
Cl2 C29 H00B 109.5 . . ?
Cl1 C29 H00B 109.5 . . ?
H00A C29 H00B 108.1 . . ?

_refine_diff_density_max         2.913
_refine_diff_density_min         -1.318
_refine_diff_density_rms         0.189


_exptl_crystal_recrystallization_method Layering
