# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_191008_zjq191008_0m
_database_code_depnum_ccdc_archive 'CCDC 1987481'
loop_
_audit_author_name
_audit_author_address
'Hongbin Zou'
;Zhejiang University
China
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;
_audit_creation_date             2019-10-09
_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         'C17 H18 N4 O2 Pd, H2 O'
_chemical_formula_sum            'C17 H20 N4 O3 Pd'
_chemical_formula_weight         434.77
_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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   15.890(8)
_cell_length_b                   15.890(8)
_cell_length_c                   14.121(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3565(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5020
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1168 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.8930.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12462
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.007
_diffrn_reflns_theta_min         2.564
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_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         0.724
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3658
_reflns_number_total             3866
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.083
_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)+(0.0213P)²+0.2128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0498
_refine_ls_wR_factor_ref         0.0510
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H1 of C1, H11 of C11, H9 of C9, H8 of C8, H2 of C2, H4
  of C4, H3 of C3
 At 1.5 times of:
  All C(H,H,H) groups, H3A of C11, All O(H) groups
2. Restrained distances
 O3-H3A
 0.87 with sigma of 0.02
3.a Free rotating group:
 O3(H3B)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C11(H11)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.62394(2) 0.65236(2) 0.83072(2) 0.02926(8) Uani 1 1 d . . . . .
O1 O 0.60279(19) 0.77319(16) 0.78315(16) 0.0409(7) Uani 1 1 d . . . . .
O2 O 0.6289(2) 0.74264(18) 0.63141(17) 0.0428(7) Uani 1 1 d . . . . .
N1 N 0.49150(19) 0.62531(19) 0.85540(18) 0.0311(6) Uani 1 1 d . . . . .
N2 N 0.59877(19) 0.47138(18) 0.87527(17) 0.0264(6) Uani 1 1 d . . . . .
N3 N 0.6125(2) 0.32001(18) 0.87186(19) 0.0340(7) Uani 1 1 d . . . . .
N4 N 0.64967(19) 0.53975(17) 0.87714(17) 0.0279(6) Uani 1 1 d . . . . .
C1 C 0.4385(3) 0.6921(3) 0.8565(3) 0.0406(9) Uani 1 1 d . . . . .
H1 H 0.461264 0.746078 0.843314 0.049 Uiso 1 1 calc R . . . .
C2 C 0.3537(3) 0.6865(3) 0.8756(3) 0.0463(10) Uani 1 1 d . . . . .
H2 H 0.319089 0.735268 0.874698 0.056 Uiso 1 1 calc R . . . .
C3 C 0.3199(3) 0.6079(3) 0.8961(3) 0.0447(10) Uani 1 1 d . . . . .
H3 H 0.261618 0.601711 0.909585 0.054 Uiso 1 1 calc R . . . .
C4 C 0.3732(3) 0.5383(2) 0.8965(2) 0.0355(8) Uani 1 1 d . . . . .
H4 H 0.351627 0.484168 0.911490 0.043 Uiso 1 1 calc R . . . .
C5 C 0.4587(2) 0.5483(2) 0.8748(2) 0.0286(7) Uani 1 1 d . . . . .
C6 C 0.5117(2) 0.4705(2) 0.8717(2) 0.0272(7) Uani 1 1 d . . . . .
C7 C 0.6483(2) 0.3979(2) 0.8763(2) 0.0290(7) Uani 1 1 d . . . . .
C8 C 0.5291(3) 0.3182(2) 0.8657(2) 0.0350(8) Uani 1 1 d . . . . .
H8 H 0.502487 0.264801 0.861210 0.042 Uiso 1 1 calc R . . . .
C9 C 0.4773(2) 0.3905(2) 0.8655(2) 0.0318(8) Uani 1 1 d . . . . .
H9 H 0.418027 0.384138 0.861035 0.038 Uiso 1 1 calc R . . . .
C10 C 0.7307(2) 0.5112(2) 0.8782(2) 0.0292(8) Uani 1 1 d . . . . .
C11 C 0.7324(2) 0.4242(2) 0.8799(2) 0.0328(8) Uani 1 1 d . . . . .
H11 H 0.780834 0.389334 0.882822 0.039 Uiso 1 1 calc R . . . .
H3A H 0.670(3) 0.739(2) 0.416(3) 0.049 Uiso 1 1 d DR . . . .
C12 C 0.7940(2) 0.5824(3) 0.8729(2) 0.0340(8) Uani 1 1 d . . . . .
C13 C 0.7509(2) 0.6533(3) 0.8135(2) 0.0397(9) Uani 1 1 d . . . . .
H13A H 0.764494 0.645207 0.745640 0.048 Uiso 1 1 calc R . . . .
H13B H 0.773436 0.708657 0.833197 0.048 Uiso 1 1 calc R . . . .
C14 C 0.8766(3) 0.5526(3) 0.8278(3) 0.0505(10) Uani 1 1 d . . . . .
H14A H 0.865263 0.530598 0.764277 0.076 Uiso 1 1 calc GR . . . .
H14B H 0.901440 0.508177 0.866992 0.076 Uiso 1 1 calc GR . . . .
H14C H 0.915820 0.600041 0.823447 0.076 Uiso 1 1 calc GR . . . .
C15 C 0.8114(3) 0.6150(3) 0.9740(2) 0.0405(9) Uani 1 1 d . . . . .
H15A H 0.852141 0.661321 0.971173 0.061 Uiso 1 1 calc GR . . . .
H15B H 0.834415 0.569294 1.012671 0.061 Uiso 1 1 calc GR . . . .
H15C H 0.758861 0.635239 1.002233 0.061 Uiso 1 1 calc GR . . . .
C16 C 0.6046(3) 0.7910(2) 0.6949(3) 0.0383(9) Uani 1 1 d . . . . .
C17 C 0.5725(3) 0.8785(3) 0.6699(3) 0.0596(12) Uani 1 1 d . . . . .
H17A H 0.511077 0.879723 0.675669 0.089 Uiso 1 1 calc GR . . . .
H17B H 0.588646 0.892188 0.604760 0.089 Uiso 1 1 calc GR . . . .
H17C H 0.597204 0.919793 0.713325 0.089 Uiso 1 1 calc GR . . . .
O3 O 0.6418(3) 0.7834(3) 0.4380(2) 0.0742(11) Uani 1 1 d D . . . .
H3B H 0.635566 0.770582 0.497509 0.111 Uiso 1 1 d G . . . .


_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 O1 2.062(3) . ?
Pd1 N1 2.176(3) . ?
Pd1 N4 1.949(3) . ?
Pd1 C13 2.033(4) . ?
O1 C16 1.278(4) . ?
O2 C16 1.242(5) . ?
N1 C1 1.354(5) . ?
N1 C5 1.357(5) . ?
N2 N4 1.355(4) . ?
N2 C6 1.385(5) . ?
N2 C7 1.408(4) . ?
N3 C7 1.363(5) . ?
N3 C8 1.329(5) . ?
N4 C10 1.364(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(5) . ?
C5 C6 1.497(5) . ?
C6 C9 1.386(5) . ?
C7 C11 1.401(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.412(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(5) . ?
C10 C12 1.516(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.562(5) . ?
C12 C14 1.533(5) . ?
C12 C15 1.543(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.522(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O3 H3A 0.90(2) . ?
O3 H3B 0.8699 . ?

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
O1 Pd1 N1 94.50(12) . . ?
N4 Pd1 O1 177.15(13) . . ?
N4 Pd1 N1 88.15(12) . . ?
N4 Pd1 C13 80.71(14) . . ?
C13 Pd1 O1 96.67(14) . . ?
C13 Pd1 N1 168.74(14) . . ?
C16 O1 Pd1 121.3(3) . . ?
C1 N1 Pd1 116.7(3) . . ?
C1 N1 C5 117.7(3) . . ?
C5 N1 Pd1 125.6(2) . . ?
N4 N2 C6 127.3(3) . . ?
N4 N2 C7 109.3(3) . . ?
C6 N2 C7 123.4(3) . . ?
C8 N3 C7 116.0(3) . . ?
N2 N4 Pd1 127.2(2) . . ?
N2 N4 C10 107.3(3) . . ?
C10 N4 Pd1 120.4(2) . . ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.1(4) . . ?
C2 C1 H1 117.9 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 121.2(3) . . ?
N1 C5 C6 121.5(3) . . ?
C4 C5 C6 117.2(3) . . ?
N2 C6 C5 123.5(3) . . ?
N2 C6 C9 113.9(3) . . ?
C9 C6 C5 122.6(3) . . ?
N3 C7 N2 121.3(3) . . ?
N3 C7 C11 132.1(3) . . ?
C11 C7 N2 106.6(3) . . ?
N3 C8 H8 117.9 . . ?
N3 C8 C9 124.3(3) . . ?
C9 C8 H8 117.9 . . ?
C6 C9 C8 121.1(3) . . ?
C6 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
N4 C10 C11 110.5(3) . . ?
N4 C10 C12 112.2(3) . . ?
C11 C10 C12 137.2(3) . . ?
C7 C11 H11 126.9 . . ?
C10 C11 C7 106.2(3) . . ?
C10 C11 H11 126.9 . . ?
C10 C12 C13 105.9(3) . . ?
C10 C12 C14 111.0(3) . . ?
C10 C12 C15 108.9(3) . . ?
C14 C12 C13 112.0(3) . . ?
C14 C12 C15 109.5(3) . . ?
C15 C12 C13 109.5(3) . . ?
Pd1 C13 H13A 109.3 . . ?
Pd1 C13 H13B 109.3 . . ?
C12 C13 Pd1 111.4(2) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 C17 114.8(4) . . ?
O2 C16 O1 125.1(4) . . ?
O2 C16 C17 120.1(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H3A O3 H3B 102.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_191220_t191220_0m
_database_code_depnum_ccdc_archive 'CCDC 1987484'
loop_
_audit_author_name
_audit_author_address
'Hongbin Zou'
;Zhejiang University
China
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-20
_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            SP34Cl
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 Cl N4'
_chemical_formula_sum            'C21 H19 Cl N4'
_chemical_formula_weight         362.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.907(6)
_cell_length_b                   10.254(9)
_cell_length_c                   11.143(9)
_cell_angle_alpha                68.74(4)
_cell_angle_beta                 87.11(4)
_cell_angle_gamma                66.43(4)
_cell_volume                     864.0(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6593
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0894 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.7532.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10576
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.060
_diffrn_reflns_theta_min         2.430
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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                3432
_reflns_number_total             3792
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.070
_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)+(0.0622P)²+0.2592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1185
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C15(H15), C16(H16),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.88319(4) -0.00062(4) 0.37047(4) 0.03421(14) Uani 1 1 d . . . . .
N1 N -0.28096(14) 0.22066(14) 1.02766(12) 0.0270(3) Uani 1 1 d . . . . .
N2 N -0.17058(14) 0.69581(14) 0.87138(12) 0.0278(3) Uani 1 1 d . . . . .
N3 N -0.07441(13) 0.45823(13) 0.83339(10) 0.0201(2) Uani 1 1 d . . . . .
N4 N 0.04060(13) 0.38153(13) 0.76941(10) 0.0210(2) Uani 1 1 d . . . . .
C1 C -0.29980(18) 0.09129(17) 1.05168(14) 0.0301(3) Uani 1 1 d . . . . .
H1 H -0.356863 0.059560 1.123186 0.036 Uiso 1 1 calc R . . . .
C2 C -0.24118(17) -0.00020(17) 0.97865(14) 0.0285(3) Uani 1 1 d . . . . .
H2 H -0.257864 -0.091529 0.999683 0.034 Uiso 1 1 calc R . . . .
C3 C -0.15779(17) 0.04561(17) 0.87437(14) 0.0274(3) Uani 1 1 d . . . . .
H3 H -0.117638 -0.013050 0.821385 0.033 Uiso 1 1 calc R . . . .
C4 C -0.13363(16) 0.17897(16) 0.84831(13) 0.0239(3) Uani 1 1 d . . . . .
H4 H -0.075259 0.211806 0.778181 0.029 Uiso 1 1 calc R . . . .
C5 C -0.19658(15) 0.26335(15) 0.92690(12) 0.0210(3) Uani 1 1 d . . . . .
C6 C -0.18401(15) 0.40951(15) 0.90883(12) 0.0210(3) Uani 1 1 d . . . . .
C7 C -0.28434(16) 0.50760(16) 0.96532(13) 0.0254(3) Uani 1 1 d . . . . .
H7 H -0.361827 0.480722 1.019141 0.030 Uiso 1 1 calc R . . . .
C8 C -0.27366(17) 0.64756(17) 0.94435(15) 0.0281(3) Uani 1 1 d . . . . .
H8 H -0.345464 0.711525 0.985496 0.034 Uiso 1 1 calc R . . . .
C9 C -0.06945(16) 0.59920(15) 0.81606(13) 0.0233(3) Uani 1 1 d . . . . .
C10 C 0.05299(16) 0.61021(16) 0.73669(14) 0.0258(3) Uani 1 1 d . . . . .
H10 H 0.086866 0.692408 0.705740 0.031 Uiso 1 1 calc R . . . .
C11 C 0.11649(15) 0.47530(15) 0.71147(12) 0.0215(3) Uani 1 1 d . . . . .
C12 C 0.26224(15) 0.42616(15) 0.63651(12) 0.0215(3) Uani 1 1 d . . . . .
C13 C 0.26368(16) 0.29664(16) 0.59535(14) 0.0256(3) Uani 1 1 d . . . . .
H13A H 0.251457 0.215807 0.672197 0.031 Uiso 1 1 calc R . . . .
H13B H 0.166828 0.339174 0.531242 0.031 Uiso 1 1 calc R . . . .
C14 C 0.41758(16) 0.22337(16) 0.53724(13) 0.0236(3) Uani 1 1 d . . . . .
C15 C 0.54979(17) 0.09135(16) 0.61557(13) 0.0267(3) Uani 1 1 d . . . . .
H15 H 0.541681 0.047723 0.705480 0.032 Uiso 1 1 calc R . . . .
C16 C 0.69270(17) 0.02223(16) 0.56544(14) 0.0269(3) Uani 1 1 d . . . . .
H16 H 0.781497 -0.067324 0.620182 0.032 Uiso 1 1 calc R . . . .
C17 C 0.70352(17) 0.08649(16) 0.43364(14) 0.0245(3) Uani 1 1 d . . . . .
C18 C 0.57469(17) 0.21627(17) 0.35194(13) 0.0262(3) Uani 1 1 d . . . . .
H18 H 0.583008 0.258624 0.261928 0.031 Uiso 1 1 calc R . . . .
C19 C 0.43268(17) 0.28321(16) 0.40486(14) 0.0261(3) Uani 1 1 d . . . . .
H19 H 0.343623 0.371948 0.349534 0.031 Uiso 1 1 calc R . . . .
C20 C 0.41946(16) 0.36960(17) 0.72708(14) 0.0278(3) Uani 1 1 d . . . . .
H20A H 0.412670 0.450292 0.757216 0.042 Uiso 1 1 calc GR . . . .
H20B H 0.516159 0.344937 0.679769 0.042 Uiso 1 1 calc GR . . . .
H20C H 0.429334 0.277686 0.801722 0.042 Uiso 1 1 calc GR . . . .
C21 C 0.25111(18) 0.56621(17) 0.51596(14) 0.0280(3) Uani 1 1 d . . . . .
H21A H 0.147476 0.606653 0.461476 0.042 Uiso 1 1 calc GR . . . .
H21B H 0.344101 0.535197 0.466573 0.042 Uiso 1 1 calc GR . . . .
H21C H 0.254660 0.645797 0.543201 0.042 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
Cl1 C17 1.7475(18) . ?
N1 C1 1.332(2) . ?
N1 C5 1.3559(19) . ?
N2 C8 1.321(2) . ?
N2 C9 1.359(2) . ?
N3 N4 1.3656(17) . ?
N3 C6 1.3827(18) . ?
N3 C9 1.406(2) . ?
N4 C11 1.3504(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C5 C6 1.487(2) . ?
C6 C7 1.375(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.410(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(2) . ?
C11 C12 1.520(2) . ?
C12 C13 1.550(2) . ?
C12 C20 1.544(2) . ?
C12 C21 1.542(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.517(2) . ?
C14 C15 1.398(2) . ?
C14 C19 1.400(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(2) . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 N1 C5 117.46(13) . . ?
C8 N2 C9 115.36(14) . . ?
N4 N3 C6 126.99(12) . . ?
N4 N3 C9 111.57(11) . . ?
C6 N3 C9 121.43(12) . . ?
C11 N4 N3 104.31(12) . . ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.12(14) . . ?
C2 C1 H1 117.9 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.11(14) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.04(14) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.85(13) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.40(13) . . ?
N1 C5 C6 112.75(12) . . ?
C4 C5 C6 124.83(12) . . ?
N3 C6 C5 123.21(12) . . ?
C7 C6 N3 115.18(13) . . ?
C7 C6 C5 121.60(13) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.82(13) . . ?
C8 C7 H7 119.6 . . ?
N2 C8 C7 124.44(13) . . ?
N2 C8 H8 117.8 . . ?
C7 C8 H8 117.8 . . ?
N2 C9 N3 122.77(13) . . ?
N2 C9 C10 131.41(14) . . ?
C10 C9 N3 105.83(12) . . ?
C9 C10 H10 127.1 . . ?
C9 C10 C11 105.70(13) . . ?
C11 C10 H10 127.1 . . ?
N4 C11 C10 112.58(13) . . ?
N4 C11 C12 120.82(13) . . ?
C10 C11 C12 126.46(12) . . ?
C11 C12 C13 110.70(11) . . ?
C11 C12 C20 106.91(12) . . ?
C11 C12 C21 108.98(12) . . ?
C20 C12 C13 110.61(12) . . ?
C21 C12 C13 110.14(13) . . ?
C21 C12 C20 109.44(12) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C12 114.77(11) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C15 C14 C13 120.38(13) . . ?
C15 C14 C19 117.62(13) . . ?
C19 C14 C13 122.00(13) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.74(14) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.82(14) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 Cl1 118.83(12) . . ?
C18 C17 Cl1 119.71(12) . . ?
C18 C17 C16 121.46(14) . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.50(14) . . ?
C19 C18 H18 120.7 . . ?
C14 C19 H19 119.1 . . ?
C18 C19 C14 121.86(14) . . ?
C18 C19 H19 119.1 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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_200106_zjq200106_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1987482'
loop_
_audit_author_name
_audit_author_address
'Hongbin Zou'
;Zhejiang University
China
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;
_audit_creation_date             2020-01-06
_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         'C60 H60 Cl4 N16 Pd4'
_chemical_formula_sum            'C60 H60 Cl4 N16 Pd4'
_chemical_formula_weight         1572.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   20.0376(7)
_cell_length_b                   20.0376(7)
_cell_length_c                   23.8666(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9582.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.843
_shelx_estimated_absorpt_T_min   0.724
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0688 before and 0.0449 after correction.
The Ratio of minimum to maximum transmission is 0.8723.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            58452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.108
_diffrn_reflns_theta_min         2.231
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                3910
_reflns_number_total             5296
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²+30.4529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1468
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C10(H10)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.60641(2) 0.63097(2) 0.54368(2) 0.05785(14) Uani 1 1 d . . . . .
Cl1 Cl 0.71029(8) 0.66608(11) 0.50576(6) 0.1039(6) Uani 1 1 d . . . . .
N1 N 0.57031(18) 0.59198(19) 0.47142(13) 0.0567(8) Uani 1 1 d . . . . .
N2 N 0.42047(19) 0.61874(18) 0.63091(13) 0.0583(8) Uani 1 1 d . . . . .
N3 N 0.40594(19) 0.58579(19) 0.53533(13) 0.0583(9) Uani 1 1 d . . . . .
N4 N 0.35718(19) 0.5683(2) 0.49837(15) 0.0680(10) Uani 1 1 d . . . . .
C1 C 0.6070(2) 0.5796(3) 0.42583(17) 0.0656(11) Uani 1 1 d . . . . .
H1 H 0.653683 0.587881 0.426919 0.079 Uiso 1 1 calc R . . . .
C2 C 0.5790(3) 0.5551(2) 0.37730(17) 0.0661(12) Uani 1 1 d . . . . .
H2 H 0.606272 0.545718 0.345702 0.079 Uiso 1 1 calc R . . . .
C3 C 0.5116(2) 0.5443(2) 0.37490(16) 0.0625(11) Uani 1 1 d . . . . .
H3 H 0.491546 0.528638 0.341336 0.075 Uiso 1 1 calc R . . . .
C4 C 0.4728(2) 0.5566(2) 0.42217(16) 0.0595(10) Uani 1 1 d . . . . .
H4 H 0.425981 0.549287 0.421303 0.071 Uiso 1 1 calc R . . . .
C5 C 0.5032(2) 0.5797(2) 0.47028(15) 0.0536(9) Uani 1 1 d . . . . .
C6 C 0.4731(2) 0.5932(2) 0.52494(15) 0.0544(9) Uani 1 1 d . . . . .
C7 C 0.5145(2) 0.6136(2) 0.56758(15) 0.0543(9) Uani 1 1 d . . . . .
C8 C 0.4851(2) 0.6250(2) 0.62063(15) 0.0571(10) Uani 1 1 d . . . . .
H8 H 0.513360 0.637994 0.650657 0.068 Uiso 1 1 calc R . . . .
C9 C 0.3793(2) 0.5996(2) 0.58825(16) 0.0596(10) Uani 1 1 d . . . . .
C10 C 0.3117(2) 0.5908(3) 0.58399(19) 0.0707(12) Uani 1 1 d . . . . .
H10 H 0.279286 0.596277 0.612690 0.085 Uiso 1 1 calc R . . . .
C11 C 0.3006(3) 0.5720(3) 0.5282(2) 0.0744(13) Uani 1 1 d . . . . .
C12 C 0.2339(3) 0.5584(4) 0.5005(2) 0.102(2) Uani 1 1 d . . . . .
C13 C 0.1925(5) 0.6177(6) 0.5023(6) 0.203(6) Uani 1 1 d . . . . .
H13A H 0.187881 0.632722 0.541216 0.305 Uiso 1 1 calc GR . . . .
H13B H 0.148309 0.607476 0.486966 0.305 Uiso 1 1 calc GR . . . .
H13C H 0.213327 0.653112 0.480007 0.305 Uiso 1 1 calc GR . . . .
C14 C 0.2428(4) 0.5261(5) 0.4438(3) 0.120(3) Uani 1 1 d . . . . .
H14A H 0.265478 0.557294 0.418528 0.180 Uiso 1 1 calc GR . . . .
H14B H 0.198950 0.514656 0.428272 0.180 Uiso 1 1 calc GR . . . .
H14C H 0.269604 0.485527 0.447747 0.180 Uiso 1 1 calc GR . . . .
C15 C 0.1973(4) 0.5010(6) 0.5354(3) 0.152(4) Uani 1 1 d . . . . .
H15A H 0.225344 0.461005 0.536023 0.229 Uiso 1 1 calc GR . . . .
H15B H 0.154396 0.490501 0.517728 0.229 Uiso 1 1 calc GR . . . .
H15C H 0.189607 0.516442 0.573834 0.229 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 Cl1 2.3763(16) . ?
Pd1 N1 2.027(3) . ?
Pd1 N2 2.028(3) 12_767 ?
Pd1 C7 1.958(4) . ?
N1 C1 1.337(5) . ?
N1 C5 1.367(6) . ?
N2 C8 1.323(6) . ?
N2 C9 1.365(5) . ?
N3 N4 1.362(5) . ?
N3 C6 1.376(6) . ?
N3 C9 1.399(5) . ?
N4 C11 1.342(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(5) . ?
C5 C6 1.463(5) . ?
C6 C7 1.376(5) . ?
C7 C8 1.416(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.401(6) . ?
C11 C12 1.516(7) . ?
C12 C13 1.450(11) . ?
C12 C14 1.511(8) . ?
C12 C15 1.597(11) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
N1 Pd1 Cl1 95.89(11) . . ?
N1 Pd1 N2 173.28(15) . 12_767 ?
N2 Pd1 Cl1 90.42(11) 12_767 . ?
C7 Pd1 Cl1 170.71(13) . . ?
C7 Pd1 N1 81.03(15) . . ?
C7 Pd1 N2 92.38(15) . 12_767 ?
C1 N1 Pd1 124.6(3) . . ?
C1 N1 C5 119.4(3) . . ?
C5 N1 Pd1 115.9(2) . . ?
C8 N2 Pd1 121.5(3) . 15_566 ?
C8 N2 C9 118.7(3) . . ?
C9 N2 Pd1 119.7(3) . 15_566 ?
N4 N3 C6 127.8(3) . . ?
N4 N3 C9 111.2(4) . . ?
C6 N3 C9 121.0(3) . . ?
C11 N4 N3 104.4(3) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(4) . . ?
C2 C1 H1 119.1 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.3(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 120.8(4) . . ?
N1 C5 C6 110.8(3) . . ?
C4 C5 C6 128.4(4) . . ?
N3 C6 C5 123.0(3) . . ?
N3 C6 C7 119.3(3) . . ?
C7 C6 C5 117.7(4) . . ?
C6 C7 Pd1 113.9(3) . . ?
C6 C7 C8 117.2(4) . . ?
C8 C7 Pd1 128.6(3) . . ?
N2 C8 C7 124.0(4) . . ?
N2 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
N2 C9 N3 119.9(4) . . ?
N2 C9 C10 133.6(4) . . ?
C10 C9 N3 106.6(4) . . ?
C9 C10 H10 127.4 . . ?
C9 C10 C11 105.2(4) . . ?
C11 C10 H10 127.4 . . ?
N4 C11 C10 112.7(4) . . ?
N4 C11 C12 120.2(4) . . ?
C10 C11 C12 127.1(5) . . ?
C11 C12 C15 107.8(6) . . ?
C13 C12 C11 110.1(6) . . ?
C13 C12 C14 116.4(7) . . ?
C13 C12 C15 108.2(8) . . ?
C14 C12 C11 111.3(5) . . ?
C14 C12 C15 102.3(7) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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_191105_t191104_0m
_database_code_depnum_ccdc_archive 'CCDC 1987483'
loop_
_audit_author_name
_audit_author_address
'Hongbin Zou'
;Zhejiang University
China
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_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            SP24OMe
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N4 O'
_chemical_formula_sum            'C23 H24 N4 O'
_chemical_formula_weight         372.46
_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'

_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4235(3)
_cell_length_b                   9.4517(3)
_cell_length_c                   11.8728(4)
_cell_angle_alpha                81.6620(10)
_cell_angle_beta                 82.0120(10)
_cell_angle_gamma                79.0930(10)
_cell_volume                     1020.62(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1187 before and 0.0388 after correction.
The Ratio of minimum to maximum transmission is 0.9231.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20604
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.117
_diffrn_reflns_theta_min         2.644
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4042
_reflns_number_total             4492
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.030
_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)+(0.0566P)²+0.2254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C22 \\sim C20-C22A
 with sigma of 0.02
 C20-C21 \\sim C20-C21A
 with sigma of 0.02
 C20-C23 \\sim C20-C23A
 with sigma of 0.02
3. Rigid bond restraints
 C20, C21, C22, C23, C21A, C22A, C23A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C23 \\sim C21A \\sim C22A \\sim C23A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
5. Others
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17)
6.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C21A(H21D,H21E,H21F), C22A(H22D,H22E,H22F),
 C23A(H23D,H23E,H23F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.64337(12) 0.27575(9) 0.86309(7) 0.0494(2) Uani 1 1 d . . . . .
N1 N 0.61590(10) 0.23011(11) 0.21730(8) 0.0377(2) Uani 1 1 d . . . . .
N2 N 0.36632(9) 0.21427(9) 0.28412(7) 0.02981(19) Uani 1 1 d . . . . .
N3 N 0.23974(10) 0.20569(10) 0.24465(8) 0.0329(2) Uani 1 1 d . . . . .
N4 N 0.21223(9) 0.34564(10) 0.53297(8) 0.0318(2) Uani 1 1 d . . . . .
C1 C 0.63029(12) 0.24154(13) 0.32376(10) 0.0354(2) Uani 1 1 d . . . . .
H1 H 0.723422 0.252324 0.339765 0.042 Uiso 1 1 calc R . . . .
C2 C 0.51778(11) 0.23916(11) 0.41774(9) 0.0303(2) Uani 1 1 d . . . . .
C3 C 0.38216(11) 0.22536(10) 0.39513(9) 0.0290(2) Uani 1 1 d . . . . .
C4 C 0.48149(12) 0.21625(11) 0.19633(9) 0.0320(2) Uani 1 1 d . . . . .
C5 C 0.42385(12) 0.20628(12) 0.09760(9) 0.0350(2) Uani 1 1 d . . . . .
H5 H 0.473797 0.203488 0.022514 0.042 Uiso 1 1 calc R . . . .
C6 C 0.27654(12) 0.20117(11) 0.13134(9) 0.0336(2) Uani 1 1 d . . . . .
C7 C 0.55063(11) 0.25070(11) 0.53428(9) 0.0296(2) Uani 1 1 d . . . . .
C8 C 0.51438(12) 0.15135(11) 0.62852(9) 0.0340(2) Uani 1 1 d . . . . .
H8 H 0.466395 0.075167 0.618143 0.041 Uiso 1 1 calc R . . . .
C9 C 0.54725(13) 0.16241(11) 0.73603(10) 0.0375(3) Uani 1 1 d . . . . .
H9 H 0.523540 0.092974 0.798739 0.045 Uiso 1 1 calc R . . . .
C10 C 0.61516(12) 0.27506(11) 0.75315(9) 0.0341(2) Uani 1 1 d . . . . .
C11 C 0.65212(11) 0.37480(11) 0.66109(10) 0.0331(2) Uani 1 1 d . . . . .
H11 H 0.698260 0.452005 0.672136 0.040 Uiso 1 1 calc R . . . .
C12 C 0.62113(11) 0.36086(11) 0.55267(9) 0.0315(2) Uani 1 1 d . . . . .
H12 H 0.648641 0.428034 0.489528 0.038 Uiso 1 1 calc R . . . .
C13 C 0.67989(17) 0.40165(15) 0.89370(11) 0.0499(3) Uani 1 1 d . . . . .
H13A H 0.773089 0.418743 0.851024 0.075 Uiso 1 1 calc GR . . . .
H13B H 0.688004 0.388814 0.976095 0.075 Uiso 1 1 calc GR . . . .
H13C H 0.604016 0.485032 0.875291 0.075 Uiso 1 1 calc GR . . . .
C14 C 0.25168(11) 0.22504(11) 0.48181(9) 0.0300(2) Uani 1 1 d . . . . .
C15 C 0.18226(12) 0.10540(13) 0.50813(10) 0.0387(3) Uani 1 1 d . . . . .
H15 H 0.211405 0.023333 0.467383 0.046 Uiso 1 1 calc R . . . .
C16 C 0.06889(13) 0.11010(14) 0.59602(11) 0.0440(3) Uani 1 1 d . . . . .
H16 H 0.019749 0.029691 0.618171 0.053 Uiso 1 1 calc R . . . .
C17 C 0.02813(12) 0.23297(14) 0.65106(10) 0.0410(3) Uani 1 1 d . . . . .
H17 H -0.048565 0.237363 0.712195 0.049 Uiso 1 1 calc R . . . .
C18 C 0.10015(12) 0.35039(13) 0.61640(9) 0.0356(2) Uani 1 1 d . . . . .
C19 C 0.05843(15) 0.48983(15) 0.66904(12) 0.0491(3) Uani 1 1 d . . . . .
H19A H 0.134172 0.498996 0.715023 0.074 Uiso 1 1 calc GR . . . .
H19B H -0.034143 0.489572 0.718187 0.074 Uiso 1 1 calc GR . . . .
H19C H 0.048047 0.571879 0.608260 0.074 Uiso 1 1 calc GR . . . .
C20 C 0.16245(13) 0.19395(13) 0.05520(10) 0.0399(3) Uani 1 1 d D U . . .
C21 C 0.2020(4) 0.0538(4) 0.0006(4) 0.0698(10) Uani 0.752(8) 1 d D U P A 1
H21A H 0.301102 0.046226 -0.038964 0.105 Uiso 0.752(8) 1 calc GR . P A 1
H21B H 0.133782 0.053855 -0.054692 0.105 Uiso 0.752(8) 1 calc GR . P A 1
H21C H 0.196564 -0.029063 0.060115 0.105 Uiso 0.752(8) 1 calc GR . P A 1
C22 C 0.0105(3) 0.2079(4) 0.1197(3) 0.0593(8) Uani 0.752(8) 1 d D U P A 1
H22A H 0.007930 0.129759 0.183504 0.089 Uiso 0.752(8) 1 calc GR . P A 1
H22B H -0.059346 0.201064 0.067617 0.089 Uiso 0.752(8) 1 calc GR . P A 1
H22C H -0.015069 0.302016 0.149464 0.089 Uiso 0.752(8) 1 calc GR . P A 1
C23 C 0.1651(4) 0.3207(4) -0.0434(3) 0.0685(9) Uani 0.752(8) 1 d D U P A 1
H23A H 0.141540 0.413326 -0.011348 0.103 Uiso 0.752(8) 1 calc GR . P A 1
H23B H 0.093202 0.316830 -0.094632 0.103 Uiso 0.752(8) 1 calc GR . P A 1
H23C H 0.262197 0.312048 -0.086593 0.103 Uiso 0.752(8) 1 calc GR . P A 1
C21A C 0.2316(14) 0.111(2) -0.0439(13) 0.092(4) Uani 0.248(8) 1 d D U P A 2
H21D H 0.305487 0.162247 -0.089872 0.139 Uiso 0.248(8) 1 calc GR . P A 2
H21E H 0.156814 0.104554 -0.091612 0.139 Uiso 0.248(8) 1 calc GR . P A 2
H21F H 0.277274 0.013473 -0.014379 0.139 Uiso 0.248(8) 1 calc GR . P A 2
C22A C 0.0461(16) 0.114(2) 0.1279(9) 0.103(5) Uani 0.248(8) 1 d D U P A 2
H22D H 0.090848 0.014432 0.154111 0.155 Uiso 0.248(8) 1 calc GR . P A 2
H22E H -0.031382 0.111610 0.081428 0.155 Uiso 0.248(8) 1 calc GR . P A 2
H22F H 0.005043 0.164939 0.194418 0.155 Uiso 0.248(8) 1 calc GR . P A 2
C23A C 0.0998(16) 0.3468(9) 0.0148(14) 0.084(4) Uani 0.248(8) 1 d D U P A 2
H23D H 0.053735 0.396761 0.080793 0.127 Uiso 0.248(8) 1 calc GR . P A 2
H23E H 0.027004 0.347492 -0.036823 0.127 Uiso 0.248(8) 1 calc GR . P A 2
H23F H 0.177497 0.396765 -0.026161 0.127 Uiso 0.248(8) 1 calc GR . P A 2


_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 C10 1.3690(14) . ?
O1 C13 1.4077(14) . ?
N1 C1 1.3118(15) . ?
N1 C4 1.3578(14) . ?
N2 N3 1.3609(12) . ?
N2 C3 1.3679(13) . ?
N2 C4 1.3972(13) . ?
N3 C6 1.3466(14) . ?
N4 C14 1.3357(14) . ?
N4 C18 1.3428(14) . ?
C1 H1 0.9500 . ?
C1 C2 1.4292(15) . ?
C2 C3 1.3751(14) . ?
C2 C7 1.4825(15) . ?
C3 C14 1.4899(14) . ?
C4 C5 1.3806(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3983(16) . ?
C6 C20 1.5145(16) . ?
C7 C8 1.4003(15) . ?
C7 C12 1.3933(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.3774(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3933(15) . ?
C10 C11 1.3871(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3885(15) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3874(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.3849(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3802(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3916(17) . ?
C18 C19 1.5022(17) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.520(3) . ?
C20 C22 1.519(3) . ?
C20 C23 1.550(3) . ?
C20 C21A 1.509(10) . ?
C20 C22A 1.543(9) . ?
C20 C23A 1.490(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 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
C10 O1 C13 119.04(9) . . ?
C1 N1 C4 116.15(9) . . ?
N3 N2 C3 125.50(8) . . ?
N3 N2 C4 112.10(8) . . ?
C3 N2 C4 122.36(9) . . ?
C6 N3 N2 104.01(9) . . ?
C14 N4 C18 118.00(9) . . ?
N1 C1 H1 117.2 . . ?
N1 C1 C2 125.55(10) . . ?
C2 C1 H1 117.2 . . ?
C1 C2 C7 119.62(9) . . ?
C3 C2 C1 117.63(10) . . ?
C3 C2 C7 122.75(9) . . ?
N2 C3 C2 117.07(9) . . ?
N2 C3 C14 118.08(9) . . ?
C2 C3 C14 124.84(9) . . ?
N1 C4 N2 121.24(10) . . ?
N1 C4 C5 133.02(10) . . ?
C5 C4 N2 105.71(9) . . ?
C4 C5 H5 127.2 . . ?
C4 C5 C6 105.54(10) . . ?
C6 C5 H5 127.2 . . ?
N3 C6 C5 112.63(10) . . ?
N3 C6 C20 120.23(10) . . ?
C5 C6 C20 127.13(10) . . ?
C8 C7 C2 121.66(9) . . ?
C12 C7 C2 120.41(9) . . ?
C12 C7 C8 117.92(10) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.99(10) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.24(10) . . ?
C10 C9 H9 119.9 . . ?
O1 C10 C9 115.53(10) . . ?
O1 C10 C11 124.66(10) . . ?
C11 C10 C9 119.80(10) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.46(10) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.56(9) . . ?
C11 C12 H12 119.2 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C3 114.54(9) . . ?
N4 C14 C15 124.02(10) . . ?
C15 C14 C3 121.40(9) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 C14 117.51(11) . . ?
C16 C15 H15 121.2 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.22(11) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.55(10) . . ?
C18 C17 H17 120.2 . . ?
N4 C18 C17 121.63(10) . . ?
N4 C18 C19 115.69(10) . . ?
C17 C18 C19 122.68(10) . . ?
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 . . ?
C6 C20 C21 109.57(17) . . ?
C6 C20 C22 112.24(13) . . ?
C6 C20 C23 108.18(13) . . ?
C6 C20 C22A 107.9(4) . . ?
C21 C20 C23 107.0(2) . . ?
C22 C20 C21 111.01(19) . . ?
C22 C20 C23 108.61(18) . . ?
C21A C20 C6 109.8(5) . . ?
C21A C20 C22A 109.6(8) . . ?
C23A C20 C6 106.6(3) . . ?
C23A C20 C21A 111.5(7) . . ?
C23A C20 C22A 111.4(8) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C21A H21D 109.5 . . ?
C20 C21A H21E 109.5 . . ?
C20 C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C20 C22A H22D 109.5 . . ?
C20 C22A H22E 109.5 . . ?
C20 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C20 C23A H23D 109.5 . . ?
C20 C23A H23E 109.5 . . ?
C20 C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
