# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_daley05
_audit_block_doi                 10.5517/ccdc.csd.cc23jtn4
_database_code_depnum_ccdc_archive 'CCDC 1952586'
loop_
_audit_author_name
_audit_author_address
'Arnold Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2019-09-09 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C40 H48 Cd N10 O4'
_chemical_formula_sum            'C40 H48 Cd N10 O4'
_chemical_formula_weight         845.28
_chemical_absolute_configuration ?
_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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   19.1032(14)
_cell_length_b                   19.103
_cell_length_c                   11.8529(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3746.0(6)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  0.8815
_exptl_absorpt_correction_T_min  0.7122
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1314
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25515
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         1.231
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                5385
_reflns_number_total             5598
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         2.540
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.198
_refine_ls_abs_structure_details 
;
 Flack x determined using 2311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.195
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1136P)²+3.6450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1795
_refine_special_details          SQUEEZE
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C14(H14), C15(H15), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5925(5) 0.1118(4) 0.3411(6) 0.0328(14) Uani 1 1 d . . . . .
H1 H 0.544410 0.094250 0.391130 0.039 Uiso 1 1 calc R . . . .
C2 C 0.6451(5) 0.2029(4) 0.3501(6) 0.0379(16) Uani 1 1 d . . . . .
H2A H 0.616648 0.226458 0.390999 0.045 Uiso 1 1 calc R . . . .
H2B H 0.696279 0.217743 0.389872 0.045 Uiso 1 1 calc R . . . .
C3 C 0.6073(4) 0.1673(4) 0.1712(5) 0.0271(13) Uani 1 1 d . . . . .
C4 C 0.5556(4) 0.1431(4) -0.0131(5) 0.0258(12) Uani 1 1 d . . . . .
C5 C 0.5666(4) 0.1654(4) -0.1337(5) 0.0283(13) Uani 1 1 d . . . . .
C6 C 0.6317(4) 0.2257(4) -0.1926(6) 0.0294(13) Uani 1 1 d . . . . .
H6 H 0.679868 0.263525 -0.154980 0.035 Uiso 1 1 calc R . . . .
C7 C 0.6236(5) 0.2284(4) -0.3091(6) 0.0328(14) Uani 1 1 d . . . . .
H7 H 0.667347 0.268583 -0.351853 0.039 Uiso 1 1 calc R . . . .
C8 C 0.5534(5) 0.1740(4) -0.3635(5) 0.0352(15) Uani 1 1 d . . . . .
H8 H 0.549713 0.177879 -0.442927 0.042 Uiso 1 1 calc R . . . .
C9 C 0.4870(5) 0.1129(4) -0.3043(5) 0.0337(14) Uani 1 1 d . . . . .
H9 H 0.438529 0.075336 -0.341461 0.040 Uiso 1 1 calc R . . . .
C10 C 0.4965(4) 0.1106(3) -0.1886(5) 0.0279(13) Uani 1 1 d . . . . .
C11 C 0.4429(4) 0.0533(4) -0.1010(5) 0.0299(14) Uani 1 1 d . . . . .
C12 C 0.3230(4) -0.0656(4) -0.0542(6) 0.0338(15) Uani 1 1 d . . . . .
C13 C 0.2187(6) -0.1915(5) -0.0251(8) 0.054(2) Uani 1 1 d . . . . .
H13A H 0.224848 -0.239693 -0.034326 0.065 Uiso 1 1 calc R . . . .
H13B H 0.160613 -0.208563 -0.029482 0.065 Uiso 1 1 calc R . . . .
C14 C 0.2550(5) -0.1491(5) 0.0884(7) 0.0401(16) Uani 1 1 d . . . . .
H14 H 0.276704 -0.180026 0.129272 0.048 Uiso 1 1 calc R . . . .
C15 C 0.6317(7) 0.0617(6) 0.3699(7) 0.057(3) Uani 1 1 d . . . . .
H15 H 0.591250 0.003830 0.354467 0.069 Uiso 1 1 calc R . . . .
C16 C 0.7048(9) 0.0843(10) 0.2963(11) 0.079(4) Uani 1 1 d . . . . .
H16A H 0.691276 0.087669 0.217454 0.119 Uiso 1 1 calc GR . . . .
H16B H 0.720720 0.043097 0.303523 0.119 Uiso 1 1 calc GR . . . .
H16C H 0.749561 0.136801 0.320280 0.119 Uiso 1 1 calc GR . . . .
C17 C 0.6511(9) 0.0697(8) 0.4972(8) 0.070(3) Uani 1 1 d . . . . .
H17A H 0.664903 0.028777 0.519671 0.105 Uiso 1 1 calc GR . . . .
H17B H 0.603711 0.061837 0.539897 0.105 Uiso 1 1 calc GR . . . .
H17C H 0.696826 0.123707 0.512899 0.105 Uiso 1 1 calc GR . . . .
C18 C 0.1962(7) -0.1400(7) 0.1659(10) 0.066(3) Uani 1 1 d . . . . .
H18 H 0.227547 -0.104867 0.230853 0.079 Uiso 1 1 calc R . . . .
C19 C 0.1346(10) -0.2211(9) 0.2119(15) 0.104(6) Uani 1 1 d . . . . .
H19A H 0.114971 -0.261072 0.150850 0.155 Uiso 1 1 calc GR . . . .
H19B H 0.089185 -0.217558 0.243959 0.155 Uiso 1 1 calc GR . . . .
H19C H 0.159464 -0.237536 0.270719 0.155 Uiso 1 1 calc GR . . . .
C20 C 0.1528(11) -0.1005(11) 0.107(2) 0.114(6) Uani 1 1 d . . . . .
H20A H 0.114763 -0.138057 0.050618 0.171 Uiso 1 1 calc GR . . . .
H20B H 0.192750 -0.050802 0.068802 0.171 Uiso 1 1 calc GR . . . .
H20C H 0.123178 -0.087577 0.162555 0.171 Uiso 1 1 calc GR . . . .
N1 N 0.5649(4) 0.1004(4) 0.2224(5) 0.0323(12) Uani 1 1 d . . . . .
N2 N 0.6121(3) 0.1872(3) 0.0588(5) 0.0275(11) Uani 1 1 d . . . . .
N3 N 0.4811(4) 0.0758(3) 0.0027(4) 0.0287(11) Uani 1 1 d . . . . .
N4 N 0.3728(4) -0.0076(3) -0.1296(5) 0.0337(13) Uani 1 1 d . . . . .
N5 N 0.3237(4) -0.0698(3) 0.0534(5) 0.0335(13) Uani 1 1 d . . . . .
O1 O 0.6607(3) 0.2308(3) 0.2335(4) 0.0352(11) Uani 1 1 d . . . . .
O2 O 0.2642(4) -0.1316(3) -0.1106(5) 0.0491(15) Uani 1 1 d . . . . .
Cd1 Cd 0.43645(4) 0.000000 0.166667 0.0276(2) Uani 1 2 d S T P . .


_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 1.516(10) . ?
C1 C15 1.521(12) . ?
C1 N1 1.479(8) . ?
C2 O1 1.457(8) . ?
C3 N1 1.275(9) . ?
C3 N2 1.376(8) . ?
C3 O1 1.348(8) . ?
C4 C5 1.476(8) . ?
C4 N2 1.301(9) . ?
C4 N3 1.372(8) . ?
C5 C6 1.388(10) . ?
C5 C10 1.382(10) . ?
C6 C7 1.393(9) . ?
C7 C8 1.379(11) . ?
C8 C9 1.408(10) . ?
C9 C10 1.386(8) . ?
C10 C11 1.485(8) . ?
C11 N3 1.384(8) . ?
C11 N4 1.306(9) . ?
C12 N4 1.370(9) . ?
C12 N5 1.278(9) . ?
C12 O2 1.372(8) . ?
C13 C14 1.544(12) . ?
C13 O2 1.449(10) . ?
C14 C18 1.527(13) . ?
C14 N5 1.485(9) . ?
C15 C16 1.513(17) . ?
C15 C17 1.543(12) . ?
C18 C19 1.502(16) . ?
C18 C20 1.54(2) . ?
N1 Cd1 2.330(6) . ?
N3 Cd1 2.317(5) . ?
N5 Cd1 2.312(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C15 116.9(7) . . ?
N1 C1 C2 102.7(5) . . ?
N1 C1 C15 111.8(6) . . ?
O1 C2 C1 104.5(5) . . ?
N1 C3 N2 131.3(6) . . ?
N1 C3 O1 117.2(6) . . ?
O1 C3 N2 111.4(6) . . ?
N2 C4 C5 119.7(6) . . ?
N2 C4 N3 130.8(6) . . ?
N3 C4 C5 109.5(6) . . ?
C6 C5 C4 131.7(7) . . ?
C10 C5 C4 107.0(6) . . ?
C10 C5 C6 121.2(6) . . ?
C5 C6 C7 117.3(6) . . ?
C8 C7 C6 121.3(6) . . ?
C7 C8 C9 121.7(6) . . ?
C10 C9 C8 116.2(7) . . ?
C5 C10 C9 122.3(6) . . ?
C5 C10 C11 106.2(5) . . ?
C9 C10 C11 131.4(6) . . ?
N3 C11 C10 109.2(6) . . ?
N4 C11 C10 119.8(6) . . ?
N4 C11 N3 130.9(6) . . ?
N4 C12 O2 110.1(6) . . ?
N5 C12 N4 132.6(6) . . ?
N5 C12 O2 117.3(6) . . ?
O2 C13 C14 105.1(6) . . ?
C18 C14 C13 114.9(9) . . ?
N5 C14 C13 103.2(6) . . ?
N5 C14 C18 112.2(7) . . ?
C1 C15 C17 109.0(8) . . ?
C16 C15 C1 111.4(8) . . ?
C16 C15 C17 113.3(10) . . ?
C14 C18 C20 112.8(11) . . ?
C19 C18 C14 110.0(10) . . ?
C19 C18 C20 109.5(13) . . ?
C1 N1 Cd1 122.9(4) . . ?
C3 N1 C1 107.7(5) . . ?
C3 N1 Cd1 124.8(5) . . ?
C4 N2 C3 122.4(6) . . ?
C4 N3 C11 108.0(5) . . ?
C4 N3 Cd1 125.8(4) . . ?
C11 N3 Cd1 125.3(4) . . ?
C11 N4 C12 122.6(6) . . ?
C12 N5 C14 108.1(6) . . ?
C12 N5 Cd1 125.4(5) . . ?
C14 N5 Cd1 121.3(5) . . ?
C3 O1 C2 105.4(5) . . ?
C12 O2 C13 106.1(6) . . ?
N1 Cd1 N1 100.2(3) . 4 ?
N3 Cd1 N1 96.4(2) . 4 ?
N3 Cd1 N1 79.42(19) 4 4 ?
N3 Cd1 N1 96.4(2) 4 . ?
N3 Cd1 N1 79.42(19) . . ?
N3 Cd1 N3 173.6(3) 4 . ?
N5 Cd1 N1 83.8(2) 4 . ?
N5 Cd1 N1 158.93(19) 4 4 ?
N5 Cd1 N1 83.8(2) . 4 ?
N5 Cd1 N1 158.93(19) . . ?
N5 Cd1 N3 79.58(19) 4 4 ?
N5 Cd1 N3 104.6(2) 4 . ?
N5 Cd1 N3 79.58(19) . . ?
N5 Cd1 N3 104.6(2) . 4 ?
N5 Cd1 N5 99.9(3) 4 . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_daley10
_audit_block_doi                 10.5517/ccdc.csd.cc23klq0
_database_code_depnum_ccdc_archive 'CCDC 1953332'
loop_
_audit_author_name
_audit_author_address
'Arnold Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H21 N5 O2'
_chemical_formula_sum            'C26 H21 N5 O2'
_chemical_formula_weight         435.48
_chemical_absolute_configuration unk
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.1731(2)
_cell_length_b                   9.1085(3)
_cell_length_c                   37.2539(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2094.70(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4689
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      64.37
_cell_measurement_theta_min      4.86
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.9175
_exptl_absorpt_correction_T_min  0.7841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            6476
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        64.541
_diffrn_reflns_theta_max         64.541
_diffrn_reflns_theta_min         4.748
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.506
_reflns_Friedel_fraction_full    0.713
_reflns_Friedel_fraction_max     0.713
_reflns_number_gt                2776
_reflns_number_total             3056
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(2)
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.098
_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)+(0.0504P)²+1.5039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1293
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14),
 C15(H15), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), N3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0196(8) 0.2295(5) 0.06397(11) 0.0344(10) Uani 1 1 d . . . . .
H1 H 1.126170 0.174259 0.076455 0.041 Uiso 1 1 calc R . . . .
C2 C 1.0594(8) 0.3753(5) 0.05542(12) 0.0403(12) Uani 1 1 d . . . . .
H2 H 1.192321 0.419505 0.062353 0.048 Uiso 1 1 calc R . . . .
C3 C 0.9081(9) 0.4560(5) 0.03701(12) 0.0415(12) Uani 1 1 d . . . . .
H3 H 0.935534 0.555819 0.031182 0.050 Uiso 1 1 calc R . . . .
C4 C 0.7143(9) 0.3901(5) 0.02698(12) 0.0415(12) Uani 1 1 d . . . . .
H4 H 0.608864 0.444950 0.014105 0.050 Uiso 1 1 calc R . . . .
C5 C 0.6745(8) 0.2458(5) 0.03563(11) 0.0350(11) Uani 1 1 d . . . . .
H5 H 0.541637 0.201759 0.028589 0.042 Uiso 1 1 calc R . . . .
C6 C 0.8250(7) 0.1638(5) 0.05442(10) 0.0269(9) Uani 1 1 d . . . . .
C7 C 0.7783(8) 0.0048(5) 0.06330(11) 0.0306(10) Uani 1 1 d . . . . .
H7 H 0.631159 -0.003001 0.074380 0.037 Uiso 1 1 calc R . . . .
C8 C 0.7930(8) -0.1008(5) 0.03098(12) 0.0363(11) Uani 1 1 d . . . . .
H8A H 0.675732 -0.174863 0.031756 0.044 Uiso 1 1 calc R . . . .
H8B H 0.783982 -0.046360 0.008024 0.044 Uiso 1 1 calc R . . . .
C9 C 1.0576(7) -0.1451(5) 0.07010(10) 0.0296(10) Uani 1 1 d . . . . .
C10 C 1.3004(8) -0.2130(4) 0.11328(11) 0.0308(10) Uani 1 1 d . . . . .
C11 C 1.4906(7) -0.2895(4) 0.12824(11) 0.0314(10) Uani 1 1 d . . . . .
C12 C 1.6412(8) -0.3788(5) 0.11197(13) 0.0408(12) Uani 1 1 d . . . . .
H12 H 1.632810 -0.400954 0.087087 0.049 Uiso 1 1 calc R . . . .
C13 C 1.8053(9) -0.4352(6) 0.13322(13) 0.0453(12) Uani 1 1 d . . . . .
H13 H 1.913002 -0.495952 0.122643 0.054 Uiso 1 1 calc R . . . .
C14 C 1.8154(9) -0.4048(6) 0.16962(14) 0.0490(13) Uani 1 1 d . . . . .
H14 H 1.928474 -0.446279 0.183635 0.059 Uiso 1 1 calc R . . . .
C15 C 1.6630(8) -0.3144(5) 0.18603(13) 0.0419(12) Uani 1 1 d . . . . .
H15 H 1.669893 -0.292669 0.210943 0.050 Uiso 1 1 calc R . . . .
C16 C 1.5021(8) -0.2581(4) 0.16462(11) 0.0325(10) Uani 1 1 d . . . . .
C17 C 1.3154(8) -0.1634(4) 0.17335(11) 0.0298(10) Uani 1 1 d . . . . .
C18 C 1.0935(8) -0.0244(5) 0.20876(11) 0.0326(10) Uani 1 1 d . . . . .
C19 C 0.8280(9) 0.0763(6) 0.23978(12) 0.0491(14) Uani 1 1 d . . . . .
H19A H 0.814941 0.144776 0.260312 0.059 Uiso 1 1 calc R . . . .
H19B H 0.695206 0.015751 0.238253 0.059 Uiso 1 1 calc R . . . .
C20 C 0.8671(8) 0.1564(6) 0.20598(12) 0.0424(12) Uani 1 1 d . . . . .
H20 H 0.952741 0.246042 0.212168 0.051 Uiso 1 1 calc R . . . .
C21 C 0.6685(7) 0.2074(5) 0.18536(11) 0.0295(10) Uani 1 1 d . . . . .
C22 C 0.5224(8) 0.2974(5) 0.20255(12) 0.0412(12) Uani 1 1 d . . . . .
H22 H 0.542267 0.322201 0.227094 0.049 Uiso 1 1 calc R . . . .
C23 C 0.3491(9) 0.3505(7) 0.18405(16) 0.0621(16) Uani 1 1 d . . . . .
H23 H 0.249765 0.414365 0.195703 0.074 Uiso 1 1 calc R . . . .
C24 C 0.3159(10) 0.3129(8) 0.14859(15) 0.0673(18) Uani 1 1 d . . . . .
H24 H 0.194074 0.349340 0.135807 0.081 Uiso 1 1 calc R . . . .
C25 C 0.4631(9) 0.2212(7) 0.13211(14) 0.0575(16) Uani 1 1 d . . . . .
H25 H 0.442484 0.194817 0.107672 0.069 Uiso 1 1 calc R . . . .
C26 C 0.6355(8) 0.1685(6) 0.15002(12) 0.0401(12) Uani 1 1 d . . . . .
H26 H 0.734429 0.104441 0.138337 0.048 Uiso 1 1 calc R . . . .
N1 N 0.9407(6) -0.0566(4) 0.08816(9) 0.0318(9) Uani 1 1 d . . . . .
N2 N 1.2420(6) -0.2205(4) 0.08022(9) 0.0324(9) Uani 1 1 d . . . . .
N3 N 1.2090(6) -0.1388(4) 0.14132(9) 0.0306(8) Uani 1 1 d . . . . .
H3A H 1.094806 -0.081676 0.139202 0.037 Uiso 1 1 calc R . . . .
N4 N 1.2655(6) -0.1189(4) 0.20497(9) 0.0352(9) Uani 1 1 d . . . . .
N5 N 1.0115(7) 0.0583(4) 0.18597(9) 0.0411(10) Uani 1 1 d . . . . .
O1 O 1.0038(5) -0.1695(3) 0.03513(7) 0.0339(7) Uani 1 1 d . . . . .
O2 O 1.0197(7) -0.0147(4) 0.24304(7) 0.0528(10) 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 H1 0.9500 . ?
C1 C2 1.387(7) . ?
C1 C6 1.388(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.373(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(6) . ?
C6 C7 1.513(6) . ?
C7 H7 1.0000 . ?
C7 C8 1.544(6) . ?
C7 N1 1.475(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 O1 1.452(6) . ?
C9 N1 1.274(5) . ?
C9 N2 1.382(6) . ?
C9 O1 1.362(5) . ?
C10 C11 1.474(6) . ?
C10 N2 1.285(5) . ?
C10 N3 1.366(5) . ?
C11 C12 1.376(6) . ?
C11 C16 1.387(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.373(6) . ?
C16 C17 1.476(6) . ?
C17 N3 1.380(5) . ?
C17 N4 1.283(5) . ?
C18 N4 1.374(6) . ?
C18 N5 1.243(6) . ?
C18 O2 1.359(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.475(7) . ?
C19 O2 1.450(6) . ?
C20 H20 1.0000 . ?
C20 C21 1.519(7) . ?
C20 N5 1.466(6) . ?
C21 C22 1.377(6) . ?
C21 C26 1.379(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.361(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.345(7) . ?
C26 H26 0.9500 . ?
N3 H3A 0.8800 . ?

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 H1 119.8 . . ?
C2 C1 C6 120.5(5) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(4) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(5) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 121.4(4) . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 120.0(4) . . ?
C6 C7 H7 109.3 . . ?
C6 C7 C8 114.5(3) . . ?
C8 C7 H7 109.3 . . ?
N1 C7 C6 111.7(4) . . ?
N1 C7 H7 109.3 . . ?
N1 C7 C8 102.3(4) . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
O1 C8 C7 103.8(3) . . ?
O1 C8 H8A 111.0 . . ?
O1 C8 H8B 111.0 . . ?
N1 C9 N2 129.5(4) . . ?
N1 C9 O1 118.1(4) . . ?
O1 C9 N2 112.4(4) . . ?
N2 C10 C11 124.1(4) . . ?
N2 C10 N3 130.0(4) . . ?
N3 C10 C11 105.9(3) . . ?
C12 C11 C10 130.6(4) . . ?
C12 C11 C16 121.2(4) . . ?
C16 C11 C10 108.2(4) . . ?
C11 C12 H12 121.2 . . ?
C11 C12 C13 117.5(4) . . ?
C13 C12 H12 121.2 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 121.5 . . ?
C16 C15 C14 117.1(4) . . ?
C16 C15 H15 121.5 . . ?
C11 C16 C17 107.2(4) . . ?
C15 C16 C11 121.9(4) . . ?
C15 C16 C17 130.9(4) . . ?
N3 C17 C16 106.0(3) . . ?
N4 C17 C16 125.1(4) . . ?
N4 C17 N3 128.9(4) . . ?
N5 C18 N4 128.6(4) . . ?
N5 C18 O2 117.8(4) . . ?
O2 C18 N4 113.3(4) . . ?
H19A C19 H19B 109.1 . . ?
C20 C19 H19A 111.2 . . ?
C20 C19 H19B 111.2 . . ?
O2 C19 H19A 111.2 . . ?
O2 C19 H19B 111.2 . . ?
O2 C19 C20 102.8(4) . . ?
C19 C20 H20 107.1 . . ?
C19 C20 C21 116.8(4) . . ?
C21 C20 H20 107.1 . . ?
N5 C20 C19 103.5(4) . . ?
N5 C20 H20 107.1 . . ?
N5 C20 C21 114.8(4) . . ?
C22 C21 C20 118.4(4) . . ?
C22 C21 C26 120.0(4) . . ?
C26 C21 C20 121.6(4) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.4(4) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.9(5) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.7 . . ?
C25 C24 C23 118.6(5) . . ?
C25 C24 H24 120.7 . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.1(5) . . ?
C26 C25 H25 119.4 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 119.9(5) . . ?
C25 C26 H26 120.0 . . ?
C9 N1 C7 107.0(3) . . ?
C10 N2 C9 117.8(4) . . ?
C10 N3 C17 112.6(4) . . ?
C10 N3 H3A 123.7 . . ?
C17 N3 H3A 123.7 . . ?
C17 N4 C18 118.5(4) . . ?
C18 N5 C20 105.6(4) . . ?
C9 O1 C8 104.5(3) . . ?
C18 O2 C19 103.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_daley13
_database_code_depnum_ccdc_archive 'CCDC 2016087'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
1,3-bis(4,5-dihydro-4-(S)-iso-propyloxazol-2-ylimino)isoindoline
_chemical_formula_moiety         'C20 H25 N5 O2'
_chemical_formula_sum            'C20 H25 N5 O2'
_chemical_formula_weight         367.45
_chemical_absolute_configuration unk
_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 0.0181 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'

_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.2785(4)
_cell_length_b                   10.8229(4)
_cell_length_c                   11.2472(4)
_cell_angle_alpha                100.313(2)
_cell_angle_beta                 109.063(2)
_cell_angle_gamma                110.537(2)
_cell_volume                     943.06(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7586
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.45
_cell_measurement_theta_min      4.41
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10393
_diffrn_reflns_point_group_measured_fraction_full 0.712
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.099
_diffrn_reflns_theta_min         4.409
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.512
_reflns_Friedel_fraction_full    0.483
_reflns_Friedel_fraction_max     0.478
_reflns_number_gt                4596
_reflns_number_total             4863
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.1916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0750
_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. Restrained distances
 N3-H3 = N3'-H3'
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3A), C4(H4), C17(H17), C18(H18), C3'(H3'A), C4'(H4'), C17'(H17'),
 C18'(H18')
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C16(H16A,H16B), C5'(H5'A,H5'B), C16'(H16C,H16D)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C9'(H9'), C10'(H10'), C11'(H11'),
 C12'(H12')
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C),
 C1'(H1'A,H1'B,H1'C), C2'(H2'A,H2'B,H2'C), C19'(H19D,H19E,H19F), C20'(H20D,H20E,
 H20F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O1 O 1.4341(3) 0.3117(2) 1.1108(2) 0.0289(5) Uani 1 1 d . . . . .
O2 O 1.4764(3) -0.0289(2) 0.66646(19) 0.0262(4) Uani 1 1 d . . . . .
N1 N 1.4792(3) 0.2231(2) 0.9355(2) 0.0236(5) Uani 1 1 d . . . . .
N2 N 1.3380(3) 0.0745(3) 1.0378(2) 0.0238(5) Uani 1 1 d . . . . .
N3 N 1.3663(3) -0.0529(3) 0.8551(2) 0.0222(5) Uani 1 1 d D . . . .
H3 H 1.419(4) 0.019(3) 0.834(3) 0.030(9) Uiso 1 1 d D . . . .
N4 N 1.3594(3) -0.2463(2) 0.7004(2) 0.0228(5) Uani 1 1 d . . . . .
N5 N 1.4797(3) -0.2206(3) 0.5487(2) 0.0260(5) Uani 1 1 d . . . . .
C1 C 1.5811(4) 0.3519(3) 0.7494(3) 0.0316(7) Uani 1 1 d . . . . .
H1A H 1.704093 0.383147 0.792546 0.047 Uiso 1 1 calc GR . . . .
H1B H 1.552292 0.377970 0.668761 0.047 Uiso 1 1 calc GR . . . .
H1C H 1.522510 0.250008 0.725334 0.047 Uiso 1 1 calc GR . . . .
C2 C 1.6115(4) 0.5808(3) 0.8848(3) 0.0313(6) Uani 1 1 d . . . . .
H2A H 1.571217 0.621468 0.944661 0.047 Uiso 1 1 calc GR . . . .
H2B H 1.583224 0.607685 0.804524 0.047 Uiso 1 1 calc GR . . . .
H2C H 1.734859 0.615503 0.930288 0.047 Uiso 1 1 calc GR . . . .
C3 C 1.5257(3) 0.4211(3) 0.8454(3) 0.0249(6) Uani 1 1 d . . . . .
H3A H 1.400279 0.388313 0.798934 0.030 Uiso 1 1 calc R . . . .
C4 C 1.5615(4) 0.3769(3) 0.9682(3) 0.0242(6) Uani 1 1 d . . . . .
H4 H 1.687031 0.412254 1.017700 0.029 Uiso 1 1 calc R . . . .
C5 C 1.4925(4) 0.4282(3) 1.0640(3) 0.0280(6) Uani 1 1 d . . . . .
H5A H 1.582905 0.513214 1.139016 0.034 Uiso 1 1 calc R . . . .
H5B H 1.397833 0.448997 1.016881 0.034 Uiso 1 1 calc R . . . .
C6 C 1.4177(3) 0.2000(3) 1.0202(3) 0.0225(6) Uani 1 1 d . . . . .
C7 C 1.3180(3) -0.0381(3) 0.9581(3) 0.0220(6) Uani 1 1 d . . . . .
C8 C 1.2379(3) -0.1794(3) 0.9645(3) 0.0228(6) Uani 1 1 d . . . . .
C9 C 1.1628(4) -0.2259(3) 1.0457(3) 0.0246(6) Uani 1 1 d . . . . .
H9 H 1.155544 -0.162822 1.111535 0.029 Uiso 1 1 calc R . . . .
C10 C 1.0984(4) -0.3679(3) 1.0279(3) 0.0277(7) Uani 1 1 d . . . . .
H10 H 1.045530 -0.402720 1.082080 0.033 Uiso 1 1 calc R . . . .
C11 C 1.1101(4) -0.4607(3) 0.9314(3) 0.0271(7) Uani 1 1 d . . . . .
H11 H 1.065615 -0.557374 0.921439 0.032 Uiso 1 1 calc R . . . .
C12 C 1.1859(4) -0.4134(3) 0.8502(3) 0.0253(6) Uani 1 1 d . . . . .
H12 H 1.194228 -0.476096 0.784865 0.030 Uiso 1 1 calc R . . . .
C13 C 1.2488(3) -0.2719(3) 0.8673(3) 0.0226(6) Uani 1 1 d . . . . .
C14 C 1.3307(3) -0.1911(3) 0.7957(3) 0.0216(6) Uani 1 1 d . . . . .
C15 C 1.4379(3) -0.1689(3) 0.6344(3) 0.0214(6) Uani 1 1 d . . . . .
C16 C 1.5509(4) 0.0201(3) 0.5785(3) 0.0256(6) Uani 1 1 d . . . . .
H16A H 1.662717 0.102449 0.630089 0.031 Uiso 1 1 calc R . . . .
H16B H 1.475494 0.045446 0.512926 0.031 Uiso 1 1 calc R . . . .
C17 C 1.5702(3) -0.1056(3) 0.5083(3) 0.0240(6) Uani 1 1 d . . . . .
H17 H 1.693264 -0.084073 0.545935 0.029 Uiso 1 1 calc R . . . .
C18 C 1.5047(4) -0.1405(3) 0.3579(3) 0.0260(6) Uani 1 1 d . . . . .
H18 H 1.381493 -0.162335 0.320414 0.031 Uiso 1 1 calc R . . . .
C19 C 1.5226(5) -0.2679(3) 0.2942(3) 0.0364(7) Uani 1 1 d . . . . .
H19A H 1.477034 -0.289284 0.197325 0.055 Uiso 1 1 calc GR . . . .
H19B H 1.459527 -0.348303 0.315139 0.055 Uiso 1 1 calc GR . . . .
H19C H 1.642868 -0.248103 0.329375 0.055 Uiso 1 1 calc GR . . . .
C20 C 1.5990(4) -0.0151(3) 0.3240(3) 0.0330(7) Uani 1 1 d . . . . .
H20A H 1.720309 0.008166 0.360450 0.050 Uiso 1 1 calc GR . . . .
H20B H 1.583416 0.065175 0.362853 0.050 Uiso 1 1 calc GR . . . .
H20C H 1.554103 -0.037956 0.226941 0.050 Uiso 1 1 calc GR . . . .
O1' O 1.0214(3) -0.3442(2) 0.2932(2) 0.0331(5) Uani 1 1 d . . . . .
O2' O 0.9906(2) -0.0001(2) 0.74423(19) 0.0249(4) Uani 1 1 d . . . . .
N1' N 1.0080(3) -0.2511(2) 0.4835(2) 0.0258(5) Uani 1 1 d . . . . .
N2' N 1.1019(3) -0.1094(3) 0.3574(2) 0.0256(5) Uani 1 1 d . . . . .
N3' N 1.0710(3) 0.0180(3) 0.5392(2) 0.0225(5) Uani 1 1 d D . . . .
H3' H 1.040(4) -0.054(3) 0.569(3) 0.036(9) Uiso 1 1 d D . . . .
N4' N 1.0765(3) 0.2107(3) 0.6933(2) 0.0241(5) Uani 1 1 d . . . . .
N5' N 1.0124(3) 0.1972(2) 0.8756(2) 0.0248(5) Uani 1 1 d . . . . .
C1' C 0.7855(4) -0.3870(3) 0.6014(3) 0.0327(7) Uani 1 1 d . . . . .
H1'A H 0.868993 -0.388125 0.681071 0.049 Uiso 1 1 calc GR . . . .
H1'B H 0.672159 -0.429674 0.599477 0.049 Uiso 1 1 calc GR . . . .
H1'C H 0.814359 -0.290137 0.603567 0.049 Uiso 1 1 calc GR . . . .
C2' C 0.7503(4) -0.6205(3) 0.4725(3) 0.0351(7) Uani 1 1 d . . . . .
H2'A H 0.749192 -0.671384 0.390622 0.053 Uiso 1 1 calc GR . . . .
H2'B H 0.639485 -0.666564 0.473982 0.053 Uiso 1 1 calc GR . . . .
H2'C H 0.838731 -0.619774 0.550078 0.053 Uiso 1 1 calc GR . . . .
C3' C 0.7870(4) -0.4695(3) 0.4770(3) 0.0269(6) Uani 1 1 d . . . . .
H3'A H 0.695955 -0.472443 0.396901 0.032 Uiso 1 1 calc R . . . .
C4' C 0.9561(3) -0.4000(3) 0.4698(3) 0.0243(6) Uani 1 1 d . . . . .
H4' H 1.045614 -0.408230 0.542379 0.029 Uiso 1 1 calc R . . . .
C5' C 0.9555(4) -0.4627(3) 0.3345(3) 0.0291(7) Uani 1 1 d . . . . .
H5'A H 1.028566 -0.511816 0.345135 0.035 Uiso 1 1 calc R . . . .
H5'B H 0.838827 -0.529473 0.268407 0.035 Uiso 1 1 calc R . . . .
C6' C 1.0418(3) -0.2318(3) 0.3859(3) 0.0242(6) Uani 1 1 d . . . . .
C7' C 1.1142(3) 0.0027(3) 0.4330(3) 0.0229(6) Uani 1 1 d . . . . .
C8' C 1.1785(3) 0.1413(3) 0.4185(3) 0.0220(6) Uani 1 1 d . . . . .
C9' C 1.2498(3) 0.1872(3) 0.3344(3) 0.0258(6) Uani 1 1 d . . . . .
H9' H 1.259013 0.124731 0.269390 0.031 Uiso 1 1 calc R . . . .
C10' C 1.3073(4) 0.3286(3) 0.3497(3) 0.0265(6) Uani 1 1 d . . . . .
H10' H 1.357024 0.363536 0.293877 0.032 Uiso 1 1 calc R . . . .
C11' C 1.2940(4) 0.4206(3) 0.4446(3) 0.0265(7) Uani 1 1 d . . . . .
H11' H 1.335206 0.516829 0.452757 0.032 Uiso 1 1 calc R . . . .
C12' C 1.2210(4) 0.3732(3) 0.5275(3) 0.0247(6) Uani 1 1 d . . . . .
H12' H 1.210260 0.435247 0.591686 0.030 Uiso 1 1 calc R . . . .
C13' C 1.1644(3) 0.2326(3) 0.5133(3) 0.0233(6) Uani 1 1 d . . . . .
C14' C 1.0972(3) 0.1540(3) 0.5933(3) 0.0218(6) Uani 1 1 d . . . . .
C15' C 1.0254(3) 0.1392(3) 0.7737(3) 0.0223(6) Uani 1 1 d . . . . .
C16' C 0.9176(4) -0.0461(3) 0.8343(3) 0.0236(6) Uani 1 1 d . . . . .
H16C H 0.966860 -0.103512 0.876082 0.028 Uiso 1 1 calc R . . . .
H16D H 0.792813 -0.101359 0.786349 0.028 Uiso 1 1 calc R . . . .
C17' C 0.9649(3) 0.0908(3) 0.9393(3) 0.0224(5) Uani 1 1 d . . . . .
H17' H 1.067428 0.110269 1.019956 0.027 Uiso 1 1 calc R . . . .
C18' C 0.8240(3) 0.0887(3) 0.9814(3) 0.0243(6) Uani 1 1 d . . . . .
H18' H 0.722625 0.071171 0.900694 0.029 Uiso 1 1 calc R . . . .
C19' C 0.8784(4) 0.2288(3) 1.0832(3) 0.0298(7) Uani 1 1 d . . . . .
H19D H 0.974819 0.245806 1.164557 0.045 Uiso 1 1 calc GR . . . .
H19E H 0.783434 0.226697 1.104586 0.045 Uiso 1 1 calc GR . . . .
H19F H 0.911798 0.303756 1.045990 0.045 Uiso 1 1 calc GR . . . .
C20' C 0.7743(4) -0.0301(3) 1.0375(3) 0.0315(7) Uani 1 1 d . . . . .
H20D H 0.873409 -0.016266 1.115007 0.047 Uiso 1 1 calc GR . . . .
H20E H 0.733734 -0.119510 0.969024 0.047 Uiso 1 1 calc GR . . . .
H20F H 0.683950 -0.030669 1.064672 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.451(4) . ?
O1 C6 1.361(4) . ?
O2 C15 1.376(3) . ?
O2 C16 1.454(3) . ?
N1 C4 1.482(4) . ?
N1 C6 1.279(3) . ?
N2 C6 1.385(4) . ?
N2 C7 1.290(4) . ?
N3 H3 0.88(2) . ?
N3 C7 1.376(4) . ?
N3 C14 1.394(4) . ?
N4 C14 1.283(4) . ?
N4 C15 1.389(3) . ?
N5 C15 1.264(4) . ?
N5 C17 1.476(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C3 1.528(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C3 1.532(4) . ?
C3 H3A 1.0000 . ?
C3 C4 1.516(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.538(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.474(4) . ?
C8 C9 1.381(4) . ?
C8 C13 1.400(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.401(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(4) . ?
C13 C14 1.475(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.543(4) . ?
C17 H17 1.0000 . ?
C17 C18 1.521(4) . ?
C18 H18 1.0000 . ?
C18 C19 1.526(4) . ?
C18 C20 1.524(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1' C5' 1.444(4) . ?
O1' C6' 1.363(4) . ?
O2' C15' 1.377(3) . ?
O2' C16' 1.457(3) . ?
N1' C4' 1.473(4) . ?
N1' C6' 1.268(3) . ?
N2' C6' 1.385(4) . ?
N2' C7' 1.295(4) . ?
N3' H3' 0.89(2) . ?
N3' C7' 1.381(4) . ?
N3' C14' 1.388(4) . ?
N4' C14' 1.287(4) . ?
N4' C15' 1.384(3) . ?
N5' C15' 1.269(4) . ?
N5' C17' 1.476(3) . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C1' C3' 1.527(4) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C2' C3' 1.535(4) . ?
C3' H3'A 1.0000 . ?
C3' C4' 1.520(4) . ?
C4' H4' 1.0000 . ?
C4' C5' 1.548(4) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C7' C8' 1.468(4) . ?
C8' C9' 1.387(4) . ?
C8' C13' 1.391(4) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.390(4) . ?
C10' H10' 0.9500 . ?
C10' C11' 1.392(4) . ?
C11' H11' 0.9500 . ?
C11' C12' 1.390(4) . ?
C12' H12' 0.9500 . ?
C12' C13' 1.384(4) . ?
C13' C14' 1.479(4) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C16' C17' 1.536(4) . ?
C17' H17' 1.0000 . ?
C17' C18' 1.524(3) . ?
C18' H18' 1.0000 . ?
C18' C19' 1.526(4) . ?
C18' C20' 1.526(4) . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 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
C6 O1 C5 104.8(2) . . ?
C15 O2 C16 105.3(2) . . ?
C6 N1 C4 106.5(2) . . ?
C7 N2 C6 117.7(2) . . ?
C7 N3 H3 123(2) . . ?
C7 N3 C14 112.2(2) . . ?
C14 N3 H3 125(2) . . ?
C14 N4 C15 122.7(2) . . ?
C15 N5 C17 107.3(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
C1 C3 C2 111.8(2) . . ?
C1 C3 H3A 108.0 . . ?
C2 C3 H3A 108.0 . . ?
C4 C3 C1 110.5(2) . . ?
C4 C3 C2 110.6(2) . . ?
C4 C3 H3A 108.0 . . ?
N1 C4 C3 112.7(2) . . ?
N1 C4 H4 108.9 . . ?
N1 C4 C5 102.9(2) . . ?
C3 C4 H4 108.9 . . ?
C3 C4 C5 114.4(2) . . ?
C5 C4 H4 108.9 . . ?
O1 C5 C4 103.7(2) . . ?
O1 C5 H5A 111.0 . . ?
O1 C5 H5B 111.0 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
O1 C6 N2 112.6(2) . . ?
N1 C6 O1 118.1(3) . . ?
N1 C6 N2 129.3(3) . . ?
N2 C7 N3 128.9(3) . . ?
N2 C7 C8 124.4(3) . . ?
N3 C7 C8 106.6(2) . . ?
C9 C8 C7 131.3(3) . . ?
C9 C8 C13 121.4(3) . . ?
C13 C8 C7 107.3(2) . . ?
C8 C9 H9 121.1 . . ?
C8 C9 C10 117.7(3) . . ?
C10 C9 H9 121.1 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 H12 121.0 . . ?
C8 C13 C14 108.2(2) . . ?
C12 C13 C8 120.9(3) . . ?
C12 C13 C14 130.9(3) . . ?
N3 C14 C13 105.6(2) . . ?
N4 C14 N3 131.1(3) . . ?
N4 C14 C13 123.3(3) . . ?
O2 C15 N4 118.7(2) . . ?
N5 C15 O2 118.4(2) . . ?
N5 C15 N4 122.8(3) . . ?
O2 C16 H16A 110.9 . . ?
O2 C16 H16B 110.9 . . ?
O2 C16 C17 104.2(2) . . ?
H16A C16 H16B 108.9 . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
N5 C17 C16 104.0(2) . . ?
N5 C17 H17 108.5 . . ?
N5 C17 C18 113.2(2) . . ?
C16 C17 H17 108.5 . . ?
C18 C17 C16 113.9(2) . . ?
C18 C17 H17 108.5 . . ?
C17 C18 H18 108.4 . . ?
C17 C18 C19 111.3(2) . . ?
C17 C18 C20 110.2(2) . . ?
C19 C18 H18 108.4 . . ?
C20 C18 H18 108.4 . . ?
C20 C18 C19 110.2(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6' O1' C5' 105.5(2) . . ?
C15' O2' C16' 104.3(2) . . ?
C6' N1' C4' 107.8(2) . . ?
C7' N2' C6' 117.7(3) . . ?
C7' N3' H3' 119(2) . . ?
C7' N3' C14' 112.0(2) . . ?
C14' N3' H3' 129(2) . . ?
C14' N4' C15' 123.0(2) . . ?
C15' N5' C17' 107.0(2) . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
C3' C1' H1'A 109.5 . . ?
C3' C1' H1'B 109.5 . . ?
C3' C1' H1'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C3' C2' H2'A 109.5 . . ?
C3' C2' H2'B 109.5 . . ?
C3' C2' H2'C 109.5 . . ?
C1' C3' C2' 111.3(2) . . ?
C1' C3' H3'A 108.2 . . ?
C2' C3' H3'A 108.2 . . ?
C4' C3' C1' 111.3(2) . . ?
C4' C3' C2' 109.3(2) . . ?
C4' C3' H3'A 108.2 . . ?
N1' C4' C3' 113.1(2) . . ?
N1' C4' H4' 108.8 . . ?
N1' C4' C5' 103.1(2) . . ?
C3' C4' H4' 108.8 . . ?
C3' C4' C5' 113.9(2) . . ?
C5' C4' H4' 108.8 . . ?
O1' C5' C4' 105.0(2) . . ?
O1' C5' H5'A 110.8 . . ?
O1' C5' H5'B 110.8 . . ?
C4' C5' H5'A 110.8 . . ?
C4' C5' H5'B 110.8 . . ?
H5'A C5' H5'B 108.8 . . ?
O1' C6' N2' 112.1(2) . . ?
N1' C6' O1' 118.3(3) . . ?
N1' C6' N2' 129.7(3) . . ?
N2' C7' N3' 128.6(3) . . ?
N2' C7' C8' 124.8(3) . . ?
N3' C7' C8' 106.6(2) . . ?
C9' C8' C7' 130.7(3) . . ?
C9' C8' C13' 121.6(3) . . ?
C13' C8' C7' 107.7(2) . . ?
C8' C9' H9' 121.5 . . ?
C8' C9' C10' 116.9(3) . . ?
C10' C9' H9' 121.5 . . ?
C9' C10' H10' 119.1 . . ?
C9' C10' C11' 121.9(3) . . ?
C11' C10' H10' 119.1 . . ?
C10' C11' H11' 119.7 . . ?
C12' C11' C10' 120.7(3) . . ?
C12' C11' H11' 119.7 . . ?
C11' C12' H12' 121.1 . . ?
C13' C12' C11' 117.8(3) . . ?
C13' C12' H12' 121.1 . . ?
C8' C13' C14' 108.0(3) . . ?
C12' C13' C8' 121.2(3) . . ?
C12' C13' C14' 130.6(3) . . ?
N3' C14' C13' 105.7(2) . . ?
N4' C14' N3' 131.0(3) . . ?
N4' C14' C13' 123.3(3) . . ?
O2' C15' N4' 119.0(2) . . ?
N5' C15' O2' 118.2(2) . . ?
N5' C15' N4' 122.8(3) . . ?
O2' C16' H16C 111.0 . . ?
O2' C16' H16D 111.0 . . ?
O2' C16' C17' 104.0(2) . . ?
H16C C16' H16D 109.0 . . ?
C17' C16' H16C 111.0 . . ?
C17' C16' H16D 111.0 . . ?
N5' C17' C16' 103.4(2) . . ?
N5' C17' H17' 108.7 . . ?
N5' C17' C18' 113.2(2) . . ?
C16' C17' H17' 108.7 . . ?
C18' C17' C16' 114.0(2) . . ?
C18' C17' H17' 108.7 . . ?
C17' C18' H18' 108.4 . . ?
C17' C18' C19' 111.0(2) . . ?
C17' C18' C20' 109.9(2) . . ?
C19' C18' H18' 108.4 . . ?
C20' C18' H18' 108.4 . . ?
C20' C18' C19' 110.7(2) . . ?
C18' C19' H19D 109.5 . . ?
C18' C19' H19E 109.5 . . ?
C18' C19' H19F 109.5 . . ?
H19D C19' H19E 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C18' C20' H20D 109.5 . . ?
C18' C20' H20E 109.5 . . ?
C18' C20' H20F 109.5 . . ?
H20D C20' H20E 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?

_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_test4_c
_database_code_depnum_ccdc_archive 'CCDC 2016649'
loop_
_audit_author_name
_audit_author_address
'Christopher Daley'
;University of San Diego
United States of America
;
_audit_update_record             
;
2020-07-15 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H27 N5 O4 Pd'
_chemical_formula_sum            'C22 H27 N5 O4 Pd'
_chemical_formula_weight         531.88
_chemical_absolute_configuration ad
_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'
Pd Pd -0.9988 1.0072 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.6646(5)
_cell_length_b                   12.2835(10)
_cell_length_c                   13.5762(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.441(2)
_cell_angle_gamma                90
_cell_volume                     1106.40(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3839
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.744
_cell_measurement_theta_min      2.240
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0469 before and 0.0436 after correction. The Ratio of minimum to maximum transmission is 0.7271. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Slow evaporation acetone:pentane solution (10:1) of compound.'
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.085
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12875
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_min         1.507
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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         0.897
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                4476
_reflns_number_total             5069
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 1953 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0608
_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.a Ternary CH refined with riding coordinates:
 C15(H15), C1(H1), C14(H14), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C20(H20A,H20B,
 H20C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Pd1 Pd 0.49914(4) 0.50567(4) 0.26823(2) 0.01796(9) Uani 1 1 d . . . . .
O3 O 0.7496(4) 0.5002(6) 0.1953(2) 0.0234(6) Uani 1 1 d . . . . .
O2 O 0.6211(5) 0.7911(3) 0.4268(2) 0.0247(7) Uani 1 1 d . . . . .
O1 O 0.1771(5) 0.2218(3) 0.1949(2) 0.0243(8) Uani 1 1 d . . . . .
N3 N 0.2790(5) 0.5104(8) 0.3565(2) 0.0199(8) Uani 1 1 d . . . . .
N1 N 0.3924(6) 0.3623(3) 0.2163(3) 0.0184(8) Uani 1 1 d . . . . .
N5 N 0.5915(6) 0.6508(3) 0.3220(3) 0.0204(9) Uani 1 1 d . . . . .
O4 O 0.5985(5) 0.5201(4) 0.0423(2) 0.0333(10) Uani 1 1 d . . . . .
N2 N 0.1079(6) 0.3410(3) 0.3136(3) 0.0209(8) Uani 1 1 d . . . . .
C15 C 0.6678(11) 0.2369(5) 0.1715(5) 0.0254(16) Uani 1 1 d . . . . .
H15 H 0.7676 0.2932 0.1975 0.030 Uiso 1 1 calc R . . . .
N4 N 0.3646(6) 0.6748(3) 0.4485(3) 0.0218(9) Uani 1 1 d . . . . .
C12 C 0.5251(7) 0.6991(4) 0.3961(3) 0.0208(10) Uani 1 1 d . . . . .
C5 C -0.0033(8) 0.4655(4) 0.4354(4) 0.0200(11) Uani 1 1 d . . . . .
C13 C 0.7890(8) 0.8018(4) 0.3671(4) 0.0253(11) Uani 1 1 d . . . . .
H13A H 0.9173 0.7824 0.4059 0.030 Uiso 1 1 calc R . . . .
H13B H 0.7990 0.8774 0.3425 0.030 Uiso 1 1 calc R . . . .
C1 C 0.4717(8) 0.2944(4) 0.1368(3) 0.0225(10) Uani 1 1 d . . . . .
H1 H 0.4931 0.3416 0.0787 0.027 Uiso 1 1 calc R . . . .
C10 C 0.0726(8) 0.5622(4) 0.4761(4) 0.0201(11) Uani 1 1 d . . . . .
C21 C 0.7476(6) 0.5081(9) 0.1015(3) 0.0242(9) Uani 1 1 d . . . . .
C14 C 0.7429(8) 0.7227(4) 0.2810(4) 0.0241(11) Uani 1 1 d . . . . .
H14 H 0.8663 0.6800 0.2695 0.029 Uiso 1 1 calc R . . . .
C6 C -0.1773(7) 0.4192(4) 0.4650(3) 0.0221(10) Uani 1 1 d . . . . .
H6 H -0.2315 0.3537 0.4364 0.026 Uiso 1 1 calc R . . . .
C2 C 0.2941(7) 0.2183(4) 0.1099(4) 0.0243(11) Uani 1 1 d . . . . .
H2A H 0.2128 0.2439 0.0495 0.029 Uiso 1 1 calc R . . . .
H2B H 0.3415 0.1434 0.0984 0.029 Uiso 1 1 calc R . . . .
C4 C 0.1325(7) 0.4323(4) 0.3617(3) 0.0192(10) Uani 1 1 d . . . . .
C22 C 0.9570(8) 0.5012(9) 0.0657(4) 0.0423(13) Uani 1 1 d . . . . .
H22A H 1.0496 0.5484 0.1065 0.063 Uiso 1 1 calc GR . . . .
H22B H 0.9509 0.5248 -0.0035 0.063 Uiso 1 1 calc GR . . . .
H22C H 1.0052 0.4258 0.0709 0.063 Uiso 1 1 calc GR . . . .
C3 C 0.2351(7) 0.3143(4) 0.2430(3) 0.0209(10) Uani 1 1 d . . . . .
C9 C -0.0188(8) 0.6164(4) 0.5486(3) 0.0258(11) Uani 1 1 d . . . . .
H9 H 0.0335 0.6829 0.5760 0.031 Uiso 1 1 calc R . . . .
C7 C -0.2690(8) 0.4738(4) 0.5391(4) 0.0243(12) Uani 1 1 d . . . . .
H7 H -0.3878 0.4444 0.5621 0.029 Uiso 1 1 calc R . . . .
C18 C 0.6556(12) 0.7765(6) 0.1849(5) 0.0293(18) Uani 1 1 d . . . . .
H18 H 0.6199 0.7168 0.1362 0.035 Uiso 1 1 calc R . . . .
C11 C 0.2541(8) 0.5893(4) 0.4258(3) 0.0212(10) Uani 1 1 d . . . . .
C8 C -0.1909(9) 0.5692(4) 0.5795(4) 0.0280(12) Uani 1 1 d . . . . .
H8 H -0.2569 0.6037 0.6301 0.034 Uiso 1 1 calc R . . . .
C19 C 0.4657(9) 0.8413(4) 0.1947(4) 0.0343(13) Uani 1 1 d . . . . .
H19A H 0.3632 0.7939 0.2193 0.051 Uiso 1 1 calc GR . . . .
H19B H 0.4153 0.8706 0.1299 0.051 Uiso 1 1 calc GR . . . .
H19C H 0.4956 0.9014 0.2412 0.051 Uiso 1 1 calc GR . . . .
C17 C 0.7488(9) 0.1818(5) 0.0817(5) 0.0437(16) Uani 1 1 d . . . . .
H17A H 0.6485 0.1302 0.0520 0.065 Uiso 1 1 calc GR . . . .
H17B H 0.8739 0.1429 0.1030 0.065 Uiso 1 1 calc GR . . . .
H17C H 0.7758 0.2373 0.0327 0.065 Uiso 1 1 calc GR . . . .
C20 C 0.8172(10) 0.8468(5) 0.1423(4) 0.0384(15) Uani 1 1 d . . . . .
H20A H 0.8604 0.9044 0.1896 0.058 Uiso 1 1 calc GR . . . .
H20B H 0.7612 0.8795 0.0799 0.058 Uiso 1 1 calc GR . . . .
H20C H 0.9332 0.8012 0.1304 0.058 Uiso 1 1 calc GR . . . .
C16 C 0.6435(9) 0.1555(4) 0.2534(4) 0.0392(14) Uani 1 1 d . . . . .
H16A H 0.6023 0.1937 0.3116 0.059 Uiso 1 1 calc GR . . . .
H16B H 0.7720 0.1183 0.2709 0.059 Uiso 1 1 calc GR . . . .
H16C H 0.5404 0.1019 0.2307 0.059 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 O3 2.021(3) . ?
Pd1 N3 1.981(3) . ?
Pd1 N1 2.002(4) . ?
Pd1 N5 2.002(4) . ?
O3 C21 1.277(5) . ?
O2 C12 1.345(6) . ?
O2 C13 1.449(6) . ?
O1 C2 1.454(5) . ?
O1 C3 1.348(6) . ?
N3 C4 1.375(8) . ?
N3 C11 1.372(9) . ?
N1 C1 1.499(6) . ?
N1 C3 1.285(6) . ?
N5 C12 1.281(6) . ?
N5 C14 1.488(6) . ?
O4 C21 1.226(5) . ?
N2 C4 1.300(6) . ?
N2 C3 1.377(6) . ?
C15 H15 1.0000 . ?
C15 C1 1.521(9) . ?
C15 C17 1.537(9) . ?
C15 C16 1.515(9) . ?
N4 C12 1.373(6) . ?
N4 C11 1.303(6) . ?
C5 C10 1.385(6) . ?
C5 C6 1.385(7) . ?
C5 C4 1.470(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.529(7) . ?
C1 H1 1.0000 . ?
C1 C2 1.525(7) . ?
C10 C9 1.378(7) . ?
C10 C11 1.482(7) . ?
C21 C22 1.523(6) . ?
C14 H14 1.0000 . ?
C14 C18 1.528(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.397(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C8 1.386(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(7) . ?
C18 H18 1.0000 . ?
C18 C19 1.512(9) . ?
C18 C20 1.535(9) . ?
C8 H8 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
N3 Pd1 O3 172.15(13) . . ?
N3 Pd1 N1 88.9(3) . . ?
N3 Pd1 N5 88.4(3) . . ?
N1 Pd1 O3 94.6(2) . . ?
N5 Pd1 O3 88.2(2) . . ?
N5 Pd1 N1 177.02(16) . . ?
C21 O3 Pd1 123.7(3) . . ?
C12 O2 C13 105.9(3) . . ?
C3 O1 C2 105.0(3) . . ?
C4 N3 Pd1 125.5(5) . . ?
C11 N3 Pd1 125.5(5) . . ?
C11 N3 C4 109.0(3) . . ?
C1 N1 Pd1 127.2(3) . . ?
C3 N1 Pd1 125.2(3) . . ?
C3 N1 C1 107.5(4) . . ?
C12 N5 Pd1 125.5(3) . . ?
C12 N5 C14 108.4(4) . . ?
C14 N5 Pd1 126.0(3) . . ?
C4 N2 C3 119.9(4) . . ?
C1 C15 H15 108.2 . . ?
C1 C15 C17 108.3(6) . . ?
C17 C15 H15 108.2 . . ?
C16 C15 H15 108.2 . . ?
C16 C15 C1 112.7(5) . . ?
C16 C15 C17 111.2(6) . . ?
C11 N4 C12 120.3(4) . . ?
O2 C12 N4 113.2(4) . . ?
N5 C12 O2 116.2(4) . . ?
N5 C12 N4 130.5(4) . . ?
C10 C5 C4 106.5(5) . . ?
C6 C5 C10 121.4(5) . . ?
C6 C5 C4 132.1(5) . . ?
O2 C13 H13A 110.7 . . ?
O2 C13 H13B 110.7 . . ?
O2 C13 C14 105.1(4) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
N1 C1 C15 112.7(4) . . ?
N1 C1 H1 109.4 . . ?
N1 C1 C2 101.2(4) . . ?
C15 C1 H1 109.4 . . ?
C15 C1 C2 114.5(4) . . ?
C2 C1 H1 109.4 . . ?
C5 C10 C11 107.0(5) . . ?
C9 C10 C5 122.0(5) . . ?
C9 C10 C11 131.0(5) . . ?
O3 C21 C22 113.0(4) . . ?
O4 C21 O3 126.5(4) . . ?
O4 C21 C22 120.5(4) . . ?
N5 C14 C13 100.7(4) . . ?
N5 C14 H14 110.2 . . ?
N5 C14 C18 111.0(5) . . ?
C13 C14 H14 110.2 . . ?
C18 C14 C13 114.2(5) . . ?
C18 C14 H14 110.2 . . ?
C5 C6 H6 121.7 . . ?
C5 C6 C7 116.6(4) . . ?
C7 C6 H6 121.7 . . ?
O1 C2 C1 104.7(4) . . ?
O1 C2 H2A 110.8 . . ?
O1 C2 H2B 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
N3 C4 C5 109.1(4) . . ?
N2 C4 N3 129.2(5) . . ?
N2 C4 C5 121.7(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C3 N2 111.7(4) . . ?
N1 C3 O1 117.0(4) . . ?
N1 C3 N2 131.3(4) . . ?
C10 C9 H9 121.7 . . ?
C10 C9 C8 116.7(5) . . ?
C8 C9 H9 121.7 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.5(5) . . ?
C8 C7 H7 119.3 . . ?
C14 C18 H18 107.2 . . ?
C14 C18 C20 109.9(6) . . ?
C19 C18 C14 114.0(5) . . ?
C19 C18 H18 107.2 . . ?
C19 C18 C20 111.1(6) . . ?
C20 C18 H18 107.2 . . ?
N3 C11 C10 108.3(4) . . ?
N4 C11 N3 129.0(5) . . ?
N4 C11 C10 122.7(4) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 C9 121.9(5) . . ?
C7 C8 H8 119.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
Pd1 O3 C21 O4 0.1(15) . . . . ?
Pd1 O3 C21 C22 -179.9(7) . . . . ?
Pd1 N3 C4 N2 1.3(8) . . . . ?
Pd1 N3 C4 C5 -179.8(4) . . . . ?
Pd1 N3 C11 N4 -0.2(9) . . . . ?
Pd1 N3 C11 C10 -179.7(4) . . . . ?
Pd1 N1 C1 C15 74.1(5) . . . . ?
Pd1 N1 C1 C2 -163.1(3) . . . . ?
Pd1 N1 C3 O1 175.4(3) . . . . ?
Pd1 N1 C3 N2 -3.7(8) . . . . ?
Pd1 N5 C12 O2 173.5(3) . . . . ?
Pd1 N5 C12 N4 -9.2(8) . . . . ?
Pd1 N5 C14 C13 -165.3(3) . . . . ?
Pd1 N5 C14 C18 73.3(5) . . . . ?
O2 C13 C14 N5 -18.7(5) . . . . ?
O2 C13 C14 C18 100.4(5) . . . . ?
N1 C1 C2 O1 -20.3(5) . . . . ?
N5 C14 C18 C19 56.6(7) . . . . ?
N5 C14 C18 C20 -178.0(5) . . . . ?
C15 C1 C2 O1 101.3(5) . . . . ?
C12 O2 C13 C14 15.0(5) . . . . ?
C12 N5 C14 C13 16.6(5) . . . . ?
C12 N5 C14 C18 -104.7(5) . . . . ?
C12 N4 C11 N3 4.1(8) . . . . ?
C12 N4 C11 C10 -176.6(4) . . . . ?
C5 C10 C9 C8 0.3(7) . . . . ?
C5 C10 C11 N3 1.0(5) . . . . ?
C5 C10 C11 N4 -178.4(4) . . . . ?
C5 C6 C7 C8 0.7(7) . . . . ?
C13 O2 C12 N5 -4.6(6) . . . . ?
C13 O2 C12 N4 177.7(4) . . . . ?
C13 C14 C18 C19 -56.5(7) . . . . ?
C13 C14 C18 C20 69.0(7) . . . . ?
C1 N1 C3 O1 -1.8(6) . . . . ?
C1 N1 C3 N2 179.1(5) . . . . ?
C10 C5 C6 C7 -1.3(7) . . . . ?
C10 C5 C4 N3 -2.5(5) . . . . ?
C10 C5 C4 N2 176.5(4) . . . . ?
C10 C9 C8 C7 -0.9(8) . . . . ?
C14 N5 C12 O2 -8.5(6) . . . . ?
C14 N5 C12 N4 168.8(5) . . . . ?
C6 C5 C10 C9 0.8(7) . . . . ?
C6 C5 C10 C11 -178.4(5) . . . . ?
C6 C5 C4 N3 176.6(5) . . . . ?
C6 C5 C4 N2 -4.4(8) . . . . ?
C6 C7 C8 C9 0.5(7) . . . . ?
C2 O1 C3 N1 -12.0(6) . . . . ?
C2 O1 C3 N2 167.2(4) . . . . ?
C4 N3 C11 N4 176.8(5) . . . . ?
C4 N3 C11 C10 -2.7(6) . . . . ?
C4 N2 C3 O1 -174.7(4) . . . . ?
C4 N2 C3 N1 4.4(8) . . . . ?
C4 C5 C10 C9 -179.9(5) . . . . ?
C4 C5 C10 C11 0.9(5) . . . . ?
C4 C5 C6 C7 179.7(5) . . . . ?
C3 O1 C2 C1 19.9(5) . . . . ?
C3 N1 C1 C15 -108.7(5) . . . . ?
C3 N1 C1 C2 14.0(5) . . . . ?
C3 N2 C4 N3 -3.0(8) . . . . ?
C3 N2 C4 C5 178.2(4) . . . . ?
C9 C10 C11 N3 -178.0(5) . . . . ?
C9 C10 C11 N4 2.5(8) . . . . ?
C11 N3 C4 N2 -175.7(5) . . . . ?
C11 N3 C4 C5 3.3(6) . . . . ?
C11 N4 C12 O2 178.5(4) . . . . ?
C11 N4 C12 N5 1.1(8) . . . . ?
C11 C10 C9 C8 179.3(5) . . . . ?
C17 C15 C1 N1 -173.0(4) . . . . ?
C17 C15 C1 C2 72.0(6) . . . . ?
C16 C15 C1 N1 63.5(6) . . . . ?
C16 C15 C1 C2 -51.5(6) . . . . ?

_olex2_submission_original_sample_id KZ-1-58
_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_daley04_0m
_audit_block_doi                 10.5517/ccdc.csd.cc23k4f8
_database_code_depnum_ccdc_archive 'CCDC 1952889'
loop_
_audit_author_name
_audit_author_address
'Arnold Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C52 H40 Cd N10 O4'
_chemical_formula_sum            'C52 H40 Cd N10 O4'
_chemical_formula_weight         981.34
_chemical_absolute_configuration ad
_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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -z'

_cell_length_a                   19.2930(15)
_cell_length_b                   19.293
_cell_length_c                   11.7970(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3802.8(7)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    8724
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.857
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.8567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1506
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_min         1.219
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4133
_reflns_number_total             4678
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details 
;
 Flack x determined using 1681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0861P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.699(2)
 0.301(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 C1-C15B
 1.54 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C15B) = Uanis(C20B)
5. Others
 Sof(H1B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=
 Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=1-FVAR(1)
 Sof(H1A)=Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=
 Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B), C14(H14)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26)
6.d Fitted hexagon refined as free rotating group:
 C15(C16,C17,C18,C19,C20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4030(7) 0.8868(7) 0.6623(9) 0.067(3) Uani 1 1 d D . . . .
H1A H 0.448933 0.907214 0.608141 0.081 Uiso 0.63(2) 1 calc R . . A 1
H1B H 0.451823 0.898435 0.617961 0.081 Uiso 0.37(2) 1 calc R . . A 2
C2 C 0.3492(7) 0.7957(7) 0.6545(8) 0.063(3) Uani 1 1 d . . . . .
H2A H 0.297499 0.781505 0.618162 0.075 Uiso 1 1 calc R . . . .
H2B H 0.375536 0.771830 0.609968 0.075 Uiso 1 1 calc R . . . .
C3 C 0.3892(5) 0.8330(6) 0.8334(7) 0.0451(18) Uani 1 1 d . . . . .
C4 C 0.4424(5) 0.8589(5) 1.0178(6) 0.0394(18) Uani 1 1 d . . . . .
C5 C 0.4341(6) 0.8369(5) 1.1387(7) 0.039(2) Uani 1 1 d . . . . .
C6 C 0.3706(6) 0.7774(6) 1.2008(7) 0.048(2) Uani 1 1 d . . . . .
H6 H 0.321828 0.740107 1.165093 0.058 Uiso 1 1 calc R . . . .
C7 C 0.3814(6) 0.7750(6) 1.3152(8) 0.052(2) Uani 1 1 d . . . . .
H7 H 0.339387 0.734616 1.359343 0.063 Uiso 1 1 calc R . . . .
C8 C 0.4503(8) 0.8285(6) 1.3672(7) 0.061(3) Uani 1 1 d . . . . .
H8 H 0.454709 0.825461 1.447004 0.074 Uiso 1 1 calc R . . . .
C9 C 0.5156(6) 0.8885(5) 1.3065(7) 0.047(2) Uani 1 1 d . . . . .
H9 H 0.564599 0.924792 1.342450 0.057 Uiso 1 1 calc R . . . .
C10 C 0.5038(5) 0.8912(5) 1.1906(6) 0.0378(16) Uani 1 1 d . . . . .
C11 C 0.5539(5) 0.9474(5) 1.1003(6) 0.0380(19) Uani 1 1 d . . . . .
C12 C 0.6728(5) 1.0650(7) 1.0503(7) 0.049(2) Uani 1 1 d . . . . .
C13 C 0.7837(7) 1.1850(7) 1.0152(10) 0.069(3) Uani 1 1 d . . . . .
H13A H 0.837594 1.190819 1.009959 0.083 Uiso 1 1 calc R . . . .
H13B H 0.789516 1.238154 1.029944 0.083 Uiso 1 1 calc R . . . .
C14 C 0.7364(6) 1.1486(6) 0.9082(8) 0.055(2) Uani 1 1 d . . . . .
H14 H 0.712116 1.181823 0.885687 0.066 Uiso 1 1 calc R . . . .
C15 C 0.3509(10) 0.9267(9) 0.6423(12) 0.078(11) Uani 0.63(2) 1 d . . . A 1
C16 C 0.2870(12) 0.9115(12) 0.7126(12) 0.126(14) Uani 0.63(2) 1 d G . . A 1
H16 H 0.274782 0.876977 0.776044 0.152 Uiso 0.63(2) 1 calc R . . A 1
C17 C 0.2409(11) 0.9469(13) 0.6902(13) 0.121(11) Uani 0.63(2) 1 d G . . A 1
H17 H 0.197285 0.936578 0.738273 0.146 Uiso 0.63(2) 1 calc R . . A 1
C18 C 0.2588(12) 0.9975(11) 0.5974(15) 0.090(8) Uani 0.63(2) 1 d G . . A 1
H18 H 0.227324 1.021714 0.582115 0.108 Uiso 0.63(2) 1 calc R . . A 1
C19 C 0.3227(12) 1.0127(9) 0.5271(13) 0.092(17) Uani 0.63(2) 1 d G . . A 1
H19 H 0.334860 1.047248 0.463726 0.111 Uiso 0.63(2) 1 calc R . . A 1
C20 C 0.3687(9) 0.9773(8) 0.5496(12) 0.061(6) Uani 0.63(2) 1 d G . . A 1
H20 H 0.412358 0.987647 0.501495 0.073 Uiso 0.63(2) 1 calc R . . A 1
C15B C 0.3739(16) 0.9402(15) 0.608(3) 0.047(6) Uani 0.37(2) 1 d D . . A 2
C16B C 0.330(3) 0.9498(19) 0.669(4) 0.079(16) Uani 0.37(2) 1 d . . . A 2
H16B H 0.320740 0.930771 0.744925 0.094 Uiso 0.37(2) 1 calc R . . A 2
C17B C 0.295(2) 0.987(2) 0.628(2) 0.064(10) Uani 0.37(2) 1 d . . . A 2
H17B H 0.256152 0.991281 0.673408 0.077 Uiso 0.37(2) 1 calc R . . A 2
C18B C 0.311(3) 1.019(2) 0.526(2) 0.036(10) Uani 0.37(2) 1 d . . . A 2
H18B H 0.284137 1.044979 0.494350 0.044 Uiso 0.37(2) 1 calc R . . A 2
C19B C 0.3716(16) 1.0120(12) 0.465(2) 0.043(8) Uani 0.37(2) 1 d . . . A 2
H19B H 0.389505 1.038406 0.393796 0.051 Uiso 0.37(2) 1 calc R . . A 2
C20B C 0.4052(16) 0.9675(15) 0.507(2) 0.047(6) Uani 0.37(2) 1 d . . . A 2
H20B H 0.443585 0.958463 0.469038 0.057 Uiso 0.37(2) 1 calc R . . A 2
C21 C 0.7801(5) 1.1436(6) 0.8076(8) 0.057(3) Uani 1 1 d . . . . .
C22 C 0.8184(7) 1.1005(7) 0.8156(12) 0.075(3) Uani 1 1 d . . . . .
H22 H 0.814863 1.073389 0.884488 0.090 Uiso 1 1 calc R . . . .
C23 C 0.8625(8) 1.0948(9) 0.7263(13) 0.092(4) Uani 1 1 d . . . . .
H23 H 0.887565 1.063195 0.731340 0.110 Uiso 1 1 calc R . . . .
C24 C 0.8677(10) 1.1384(9) 0.6284(12) 0.101(6) Uani 1 1 d . . . . .
H24 H 0.897531 1.135885 0.565952 0.121 Uiso 1 1 calc R . . . .
C25 C 0.8324(8) 1.1843(10) 0.6176(11) 0.085(4) Uani 1 1 d . . . . .
H25 H 0.840193 1.216174 0.552302 0.102 Uiso 1 1 calc R . . . .
C26 C 0.7848(7) 1.1818(9) 0.7069(9) 0.076(4) Uani 1 1 d . . . . .
H26 H 0.754081 1.207537 0.698460 0.091 Uiso 1 1 calc R . . . .
Cd1 Cd 0.55657(5) 1.000000 0.833333 0.0444(2) Uani 1 2 d S T P . .
N1 N 0.4303(5) 0.9008(5) 0.7813(6) 0.0529(19) Uani 1 1 d . . . . .
N2 N 0.3857(5) 0.8142(5) 0.9472(6) 0.0446(18) Uani 1 1 d . . . . .
N3 N 0.5157(4) 0.9264(4) 0.9996(6) 0.0376(13) Uani 1 1 d . . . . .
N4 N 0.6249(5) 1.0083(5) 1.1263(5) 0.0444(18) Uani 1 1 d . . . . .
N5 N 0.6697(5) 1.0692(5) 0.9429(6) 0.053(2) Uani 1 1 d . . . . .
O1 O 0.3369(4) 0.7673(4) 0.7714(5) 0.0546(17) Uani 1 1 d . . . . .
O2 O 0.7364(4) 1.1282(5) 1.1035(5) 0.067(2) 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 C2 1.534(16) . ?
C1 C15 1.561(16) . ?
C1 C15B 1.5398(15) . ?
C1 N1 1.475(12) . ?
C2 O1 1.458(11) . ?
C3 N1 1.296(12) . ?
C3 N2 1.384(11) . ?
C3 O1 1.371(11) . ?
C4 C5 1.473(11) . ?
C4 N2 1.299(11) . ?
C4 N3 1.380(11) . ?
C5 C6 1.396(13) . ?
C5 C10 1.368(13) . ?
C6 C7 1.371(12) . ?
C7 C8 1.356(14) . ?
C8 C9 1.406(14) . ?
C9 C10 1.392(10) . ?
C10 C11 1.482(11) . ?
C11 N3 1.349(10) . ?
C11 N4 1.320(11) . ?
C12 N4 1.357(13) . ?
C12 N5 1.273(10) . ?
C12 O2 1.376(12) . ?
C13 C14 1.509(15) . ?
C13 O2 1.456(13) . ?
C14 C21 1.486(12) . ?
C14 N5 1.483(13) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C15B C16B 1.20(6) . ?
C15B C20B 1.32(4) . ?
C16B C17B 1.30(5) . ?
C17B C18B 1.32(5) . ?
C18B C19B 1.44(5) . ?
C19B C20B 1.40(4) . ?
C21 C22 1.365(16) . ?
C21 C26 1.376(16) . ?
C22 C23 1.393(18) . ?
C23 C24 1.40(2) . ?
C24 C25 1.37(2) . ?
C25 C26 1.383(16) . ?
Cd1 N1 2.305(8) 4_676 ?
Cd1 N1 2.305(8) . ?
Cd1 N3 2.316(7) . ?
Cd1 N3 2.316(7) 4_676 ?
Cd1 N5 2.302(8) . ?
Cd1 N5 2.302(8) 4_676 ?

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 C15 108.8(10) . . ?
C2 C1 C15B 118.5(13) . . ?
N1 C1 C2 104.0(8) . . ?
N1 C1 C15 108.2(10) . . ?
N1 C1 C15B 119.4(15) . . ?
O1 C2 C1 105.2(8) . . ?
N1 C3 N2 130.6(8) . . ?
N1 C3 O1 118.5(7) . . ?
O1 C3 N2 110.9(8) . . ?
N2 C4 C5 119.7(8) . . ?
N2 C4 N3 130.7(7) . . ?
N3 C4 C5 109.6(7) . . ?
C6 C5 C4 132.0(9) . . ?
C10 C5 C4 106.8(8) . . ?
C10 C5 C6 121.1(7) . . ?
C7 C6 C5 117.3(9) . . ?
C8 C7 C6 121.8(9) . . ?
C7 C8 C9 122.0(8) . . ?
C10 C9 C8 115.8(9) . . ?
C5 C10 C9 121.9(8) . . ?
C5 C10 C11 105.7(6) . . ?
C9 C10 C11 132.4(8) . . ?
N3 C11 C10 110.8(7) . . ?
N4 C11 C10 119.4(7) . . ?
N4 C11 N3 129.8(7) . . ?
N4 C12 O2 111.0(7) . . ?
N5 C12 N4 132.4(10) . . ?
N5 C12 O2 116.5(9) . . ?
O2 C13 C14 104.1(8) . . ?
C21 C14 C13 117.8(9) . . ?
N5 C14 C13 105.1(8) . . ?
N5 C14 C21 112.3(8) . . ?
C16 C15 C1 121.9(9) . . ?
C16 C15 C20 120.0 . . ?
C20 C15 C1 118.1(9) . . ?
C15 C16 C17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C19 C18 C17 120.0 . . ?
C18 C19 C20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C16B C15B C1 112(2) . . ?
C16B C15B C20B 135(2) . . ?
C20B C15B C1 113(2) . . ?
C15B C16B C17B 118(4) . . ?
C16B C17B C18B 122(4) . . ?
C17B C18B C19B 115(3) . . ?
C20B C19B C18B 122(3) . . ?
C15B C20B C19B 108(3) . . ?
C22 C21 C14 118.8(10) . . ?
C22 C21 C26 118.4(10) . . ?
C26 C21 C14 122.8(11) . . ?
C21 C22 C23 122.3(13) . . ?
C22 C23 C24 116.0(14) . . ?
C25 C24 C23 123.8(12) . . ?
C24 C25 C26 116.4(14) . . ?
C21 C26 C25 122.7(14) . . ?
N1 Cd1 N1 100.1(4) . 4_676 ?
N1 Cd1 N3 79.8(2) . . ?
N1 Cd1 N3 97.7(2) 4_676 . ?
N1 Cd1 N3 79.8(2) 4_676 4_676 ?
N1 Cd1 N3 97.7(2) . 4_676 ?
N3 Cd1 N3 176.1(3) 4_676 . ?
N5 Cd1 N1 85.0(3) 4_676 . ?
N5 Cd1 N1 158.9(2) . . ?
N5 Cd1 N1 85.0(3) . 4_676 ?
N5 Cd1 N1 158.9(2) 4_676 4_676 ?
N5 Cd1 N3 103.4(3) . 4_676 ?
N5 Cd1 N3 79.3(3) . . ?
N5 Cd1 N3 103.4(3) 4_676 . ?
N5 Cd1 N3 79.3(3) 4_676 4_676 ?
N5 Cd1 N5 97.7(4) 4_676 . ?
C1 N1 Cd1 122.5(6) . . ?
C3 N1 C1 106.5(8) . . ?
C3 N1 Cd1 124.8(5) . . ?
C4 N2 C3 122.2(8) . . ?
C4 N3 Cd1 125.8(5) . . ?
C11 N3 C4 107.1(7) . . ?
C11 N3 Cd1 126.5(5) . . ?
C11 N4 C12 123.3(7) . . ?
C12 N5 C14 107.3(9) . . ?
C12 N5 Cd1 125.6(7) . . ?
C14 N5 Cd1 121.7(6) . . ?
C3 O1 C2 104.5(8) . . ?
C12 O2 C13 106.7(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.699(2)
2 0.301(2)

