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

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

data_ijsf1330
_database_code_depnum_ccdc_archive 'CCDC 1863214'
_audit_update_record             
;
2018-08-21 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_audit_creation_date             2013-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13.97 H12 Br0.03 N1.97 O'
_chemical_formula_sum            'C13.97 H12 Br0.03 N1.97 O'
_chemical_formula_weight         225.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H12 N2 O1'
_chemical_oxdiff_usercomment     "Joshua's JTWB-3-162"
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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.0909(2)
_cell_length_b                   13.3680(4)
_cell_length_c                   7.95097(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.498(2)
_cell_angle_gamma                90.00
_cell_volume                     1177.72(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.6330
_cell_measurement_theta_min      3.4460
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             475
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'slow evaporation from CHCl3'
_exptl_crystal_size_max          0.1799
_exptl_crystal_size_mid          0.1320
_exptl_crystal_size_min          0.0503
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8699
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.05
_diffrn_reflns_theta_min         2.98
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9203
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0386464000
_diffrn_orient_matrix_UB_12      -0.0262240000
_diffrn_orient_matrix_UB_13      0.0534909000
_diffrn_orient_matrix_UB_21      -0.0478964000
_diffrn_orient_matrix_UB_22      0.0330700000
_diffrn_orient_matrix_UB_23      -0.0234815000
_diffrn_orient_matrix_UB_31      -0.0176613000
_diffrn_orient_matrix_UB_32      -0.0321771000
_diffrn_orient_matrix_UB_33      -0.0674804000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2788
_reflns_number_total             3781
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3781
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.1045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1318
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

There was a mix of product (-CN) and starting material (-Br), the ratio was fixed at 3% starting material.
The ADP of Bromide in the minor component was restrained to be approx. isotropic.
;
_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. Uiso/Uaniso restraints and constraints
Uanis(Br1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Others
 Fixed Sof: Br1(0.03) C6(0.97) N2(0.97)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.4700(9) 0.7374(9) 0.6900(15) 0.039(3) Uani 0.03 1 d PU A 2
C1 C 0.32152(11) 0.45698(11) 0.54174(15) 0.0160(3) Uani 1 1 d . . .
C2 C 0.37256(12) 0.55601(11) 0.53977(16) 0.0174(3) Uani 1 1 d . A .
H2 H 0.3884 0.5869 0.4354 0.021 Uiso 1 1 calc R . .
C3 C 0.39832(11) 0.60591(11) 0.68700(17) 0.0169(3) Uani 1 1 d . . .
C4 C 0.37729(12) 0.56171(11) 0.84472(16) 0.0175(3) Uani 1 1 d . A .
H4 H 0.3986 0.5962 0.9461 0.021 Uiso 1 1 calc R . .
C5 C 0.32617(11) 0.46911(11) 0.84968(15) 0.0154(3) Uani 1 1 d . . .
C6 C 0.44408(17) 0.70599(17) 0.6839(3) 0.0227(4) Uani 0.97 1 d P A 1
C7 C 0.30214(13) 0.41883(11) 1.01275(16) 0.0204(3) Uani 1 1 d . A .
H7A H 0.2163 0.4018 1.0154 0.031 Uiso 1 1 calc R . .
H7B H 0.3238 0.4641 1.1062 0.031 Uiso 1 1 calc R . .
H7C H 0.3506 0.3577 1.0236 0.031 Uiso 1 1 calc R . .
C8 C 0.23468(11) 0.32194(10) 0.70541(16) 0.0164(3) Uani 1 1 d . . .
H8A H 0.2748 0.2794 0.7931 0.020 Uiso 1 1 calc R A .
H8B H 0.2424 0.2882 0.5956 0.020 Uiso 1 1 calc R . .
C9 C 0.10208(11) 0.33125(11) 0.74120(16) 0.0166(3) Uani 1 1 d . A .
C10 C 0.04380(12) 0.24937(12) 0.80893(17) 0.0234(3) Uani 1 1 d . . .
H10 H 0.0877 0.1897 0.8333 0.028 Uiso 1 1 calc R A .
C11 C -0.07812(13) 0.25427(15) 0.8411(2) 0.0325(4) Uani 1 1 d . A .
H11 H -0.1173 0.1980 0.8872 0.039 Uiso 1 1 calc R . .
C12 C -0.14276(13) 0.34118(14) 0.8062(2) 0.0320(4) Uani 1 1 d . . .
H12 H -0.2260 0.3445 0.8289 0.038 Uiso 1 1 calc R A .
C13 C -0.08588(13) 0.42296(13) 0.7383(2) 0.0278(3) Uani 1 1 d . A .
H13 H -0.1301 0.4825 0.7139 0.033 Uiso 1 1 calc R . .
C14 C 0.03654(12) 0.41782(11) 0.70576(18) 0.0215(3) Uani 1 1 d . . .
H14 H 0.0754 0.4740 0.6590 0.026 Uiso 1 1 calc R A .
N1 N 0.29672(9) 0.41917(9) 0.70147(13) 0.0142(2) Uani 1 1 d . A .
N2 N 0.47520(13) 0.78806(14) 0.6866(2) 0.0258(3) Uani 0.97 1 d P A 1
O1 O 0.29755(9) 0.40722(8) 0.41331(11) 0.0229(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.039(3) 0.038(3) 0.039(3) -0.0001(19) 0.0028(18) -0.0022(19)
C1 0.0146(6) 0.0195(7) 0.0139(6) 0.0012(5) 0.0015(4) 0.0012(5)
C2 0.0172(6) 0.0186(7) 0.0166(6) 0.0026(5) 0.0025(4) 0.0004(5)
C3 0.0135(5) 0.0163(7) 0.0208(6) 0.0008(5) 0.0019(4) 0.0003(5)
C4 0.0182(6) 0.0182(7) 0.0162(6) -0.0019(5) 0.0005(5) -0.0008(5)
C5 0.0151(6) 0.0172(7) 0.0141(6) -0.0004(5) 0.0011(4) 0.0012(5)
C6 0.0166(8) 0.0287(12) 0.0228(8) 0.0044(8) 0.0002(6) 0.0040(8)
C7 0.0244(7) 0.0226(8) 0.0144(6) 0.0009(6) 0.0027(5) -0.0019(6)
C8 0.0171(6) 0.0125(7) 0.0195(6) -0.0006(5) 0.0010(4) -0.0005(5)
C9 0.0167(6) 0.0170(7) 0.0160(6) 0.0001(5) -0.0004(4) -0.0013(5)
C10 0.0206(6) 0.0218(7) 0.0274(7) 0.0051(7) -0.0013(5) -0.0023(6)
C11 0.0224(7) 0.0354(10) 0.0400(9) 0.0103(8) 0.0036(6) -0.0085(7)
C12 0.0155(6) 0.0427(11) 0.0380(9) 0.0036(8) 0.0044(6) -0.0012(6)
C13 0.0194(7) 0.0306(9) 0.0334(8) 0.0023(7) 0.0010(6) 0.0058(6)
C14 0.0183(6) 0.0200(8) 0.0263(7) 0.0026(6) 0.0020(5) -0.0001(5)
N1 0.0146(5) 0.0144(6) 0.0138(5) 0.0001(4) 0.0016(4) 0.0008(4)
N2 0.0216(7) 0.0247(9) 0.0310(8) 0.0050(7) -0.0002(5) 0.0032(6)
O1 0.0280(5) 0.0250(6) 0.0156(5) -0.0039(4) 0.0009(4) -0.0030(4)

_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
Br1 C3 1.929(11) . ?
C1 C2 1.4401(19) . ?
C1 N1 1.4052(16) . ?
C1 O1 1.2379(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3667(19) . ?
C3 C4 1.4148(19) . ?
C3 C6 1.431(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.3628(19) . ?
C5 C7 1.4947(18) . ?
C5 N1 1.3811(16) . ?
C6 N2 1.150(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5153(18) . ?
C8 N1 1.4717(17) . ?
C9 C10 1.391(2) . ?
C9 C14 1.3890(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(2) . ?
C14 H14 0.9500 . ?

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 C1 C2 115.66(11) . . ?
O1 C1 C2 123.74(12) . . ?
O1 C1 N1 120.59(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.46(13) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 Br1 121.7(4) . . ?
C2 C3 C4 121.26(13) . . ?
C2 C3 C6 120.17(14) . . ?
C4 C3 Br1 117.0(4) . . ?
C4 C3 C6 118.54(13) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.33(12) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C7 121.58(12) . . ?
C4 C5 N1 119.84(12) . . ?
N1 C5 C7 118.57(12) . . ?
N2 C6 C3 176.0(2) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
N1 C8 C9 112.95(11) . . ?
C10 C9 C8 118.63(12) . . ?
C14 C9 C8 122.28(12) . . ?
C14 C9 C10 119.09(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.44(15) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.10(16) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.98(14) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.83(15) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 120.56(14) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C1 N1 C8 116.55(10) . . ?
C5 N1 C1 123.30(12) . . ?
C5 N1 C8 120.14(11) . . ?

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
Br1 C3 C4 C5 179.6(4) . . . . ?
C1 C2 C3 Br1 178.6(4) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C2 C3 C6 -177.25(13) . . . . ?
C2 C1 N1 C5 -4.38(18) . . . . ?
C2 C1 N1 C8 174.75(11) . . . . ?
C2 C3 C4 C5 -2.5(2) . . . . ?
C3 C4 C5 C7 179.89(12) . . . . ?
C3 C4 C5 N1 0.67(19) . . . . ?
C4 C5 N1 C1 2.90(19) . . . . ?
C4 C5 N1 C8 -176.21(12) . . . . ?
C6 C3 C4 C5 175.62(13) . . . . ?
C7 C5 N1 C1 -176.35(12) . . . . ?
C7 C5 N1 C8 4.55(17) . . . . ?
C8 C9 C10 C11 -178.99(13) . . . . ?
C8 C9 C14 C13 179.06(13) . . . . ?
C9 C8 N1 C1 -103.74(13) . . . . ?
C9 C8 N1 C5 75.43(14) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C9 C14 C13 0.3(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C9 -0.1(2) . . . . ?
C14 C9 C10 C11 -0.2(2) . . . . ?
N1 C1 C2 C3 2.46(18) . . . . ?
N1 C8 C9 C10 -156.58(12) . . . . ?
N1 C8 C9 C14 24.67(17) . . . . ?
O1 C1 C2 C3 -179.02(13) . . . . ?
O1 C1 N1 C5 177.05(12) . . . . ?
O1 C1 N1 C8 -3.82(18) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 3 3 0.0660 2.0000 3.0000 3.0000 0.0045 -0.0670 -0.3343
-2 -4 1 0.0405 -2.0000 -4.0000 1.0000 0.2357 -0.0600 0.0966
0 2 1 0.0779 0.0000 2.0000 1.0000 0.0010 0.0427 -0.1318
-6 -4 3 0.0279 -6.0000 -4.0000 3.0000 0.4972 0.0847 0.0322
-4 -4 1 0.0390 -4.0000 -4.0000 1.0000 0.3130 0.0358 0.1319
3 2 -2 0.0180 3.0000 2.0000 -2.0000 -0.2754 -0.0306 0.0176
2 -3 0 0.0692 2.0000 -3.0000 -0.0000 0.0014 -0.1950 0.0612
-4 4 -1 0.0902 -4.0000 4.0000 -1.0000 -0.0038 0.3473 0.0094
-2 -3 -3 0.0660 -2.0000 -3.0000 -3.0000 -0.0045 0.0670 0.3343
-1 -1 2 0.0440 -1.0000 -1.0000 2.0000 0.1719 -0.0321 -0.0851
-2 -1 2 0.0363 -2.0000 -1.0000 2.0000 0.2105 0.0158 -0.0675

####################################################################### 
# 
# 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_ijsf1464a
_database_code_depnum_ccdc_archive 'CCDC 1863215'
_audit_update_record             
;
2018-08-21 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_audit_creation_date             2014-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H24 N2 O4 Pd, 2(H2 O)'
_chemical_formula_sum            'C12 H28 N2 O6 Pd'
_chemical_formula_weight         402.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H28 N2 O8 Pd1'
_chemical_oxdiff_usercomment     'Joshua JTWB-4-188'
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'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.1405(6)
_cell_length_b                   6.10222(17)
_cell_length_c                   16.0694(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.140(3)
_cell_angle_gamma                90
_cell_volume                     1680.78(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2263
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      69.3090
_cell_measurement_theta_min      5.1520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.155
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.1343
_exptl_crystal_size_mid          0.0963
_exptl_crystal_size_min          0.0364
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.9964
_diffrn_reflns_Laue_measured_fraction_max 0.9964
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4628
_diffrn_reflns_point_group_measured_fraction_full 0.9964
_diffrn_reflns_point_group_measured_fraction_max 0.9964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         5.161
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9964
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  154.0000 -159.0000 58

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000    0.0000 117

#__ type_ start__ end____ width___ exp.time_
  4 omega   24.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  5 omega  -16.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00  146.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   30.0000 110

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00  130.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   86.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 14 omega   36.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 15 omega   78.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 16 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 17 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
 18 omega   24.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  120.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0892939000
_diffrn_orient_matrix_UB_12      -0.0059208000
_diffrn_orient_matrix_UB_13      -0.0104879000
_diffrn_orient_matrix_UB_21      -0.0005199000
_diffrn_orient_matrix_UB_22      0.2484407000
_diffrn_orient_matrix_UB_23      -0.0169170000
_diffrn_orient_matrix_UB_31      0.0099656000
_diffrn_orient_matrix_UB_32      -0.0440964000
_diffrn_orient_matrix_UB_33      -0.0938376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1307
_reflns_number_total             1496
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.645
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.086
_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)+(0.0393P)²+4.7337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0759
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3711(2) 0.1051(6) 0.4934(2) 0.0218(7) Uani 1 1 d . . . . .
H1A H 0.3961 0.0199 0.5369 0.026 Uiso 1 1 calc R . . . .
H1B H 0.3400 0.2194 0.5189 0.026 Uiso 1 1 calc R . . . .
C2 C 0.4317(2) 0.2033(6) 0.4348(3) 0.0267(8) Uani 1 1 d . . . . .
H2A H 0.4813 0.2219 0.4631 0.032 Uiso 1 1 calc R . . . .
H2B H 0.4144 0.3446 0.4141 0.032 Uiso 1 1 calc R . . . .
C3 C 0.4390(2) 0.0358(6) 0.3627(2) 0.0274(8) Uani 1 1 d . . . . .
H3A H 0.4283 0.1055 0.3096 0.033 Uiso 1 1 calc R . . . .
H3B H 0.4910 -0.0266 0.3612 0.033 Uiso 1 1 calc R . . . .
C4 C 0.3786(2) -0.1403(6) 0.3811(2) 0.0238(7) Uani 1 1 d . . . . .
H4A H 0.3525 -0.1861 0.3303 0.029 Uiso 1 1 calc R . . . .
H4B H 0.4030 -0.2673 0.4065 0.029 Uiso 1 1 calc R . . . .
C5 C 0.14892(19) -0.1337(5) 0.3656(2) 0.0180(7) Uani 1 1 d . . . . .
C6 C 0.0873(2) 0.0098(6) 0.3261(2) 0.0263(8) Uani 1 1 d . . . . .
H6A H 0.0426 0.0170 0.3618 0.040 Uiso 1 1 calc GR . . . .
H6B H 0.0723 -0.0510 0.2733 0.040 Uiso 1 1 calc GR . . . .
H6C H 0.1079 0.1545 0.3179 0.040 Uiso 1 1 calc GR . . . .
N1 N 0.32218(16) -0.0370(5) 0.43947(17) 0.0175(6) Uani 1 1 d . . . . .
H1 H 0.292(3) 0.044(8) 0.415(3) 0.029(12) Uiso 1 1 d . . . . .
O1 O 0.15673(13) -0.1111(4) 0.44451(14) 0.0178(5) Uani 1 1 d . . . . .
O2 O 0.18871(17) -0.2596(4) 0.32219(16) 0.0250(6) Uani 1 1 d . . . . .
Pd1 Pd 0.2500 -0.2500 0.5000 0.01255(13) Uani 1 2 d S T P . .
O3 O 0.25657(19) 0.3137(5) 0.33740(18) 0.0318(7) Uani 1 1 d . . . . .
H3C H 0.274(3) 0.301(9) 0.289(4) 0.044(15) Uiso 1 1 d . . . . .
H3D H 0.238(3) 0.418(9) 0.338(3) 0.035(15) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0281(17) 0.0152(16) 0.0223(17) -0.0020(14) -0.0002(14) -0.0022(14)
C2 0.0261(18) 0.0173(16) 0.037(2) 0.0031(16) 0.0038(16) -0.0017(15)
C3 0.0290(18) 0.0261(19) 0.0271(19) 0.0076(16) 0.0084(15) 0.0012(16)
C4 0.0321(18) 0.0190(17) 0.0204(17) -0.0024(15) 0.0089(14) 0.0004(15)
C5 0.0235(16) 0.0119(15) 0.0185(17) 0.0027(13) -0.0002(13) -0.0018(14)
C6 0.0290(18) 0.0233(18) 0.0267(19) 0.0032(15) -0.0069(14) 0.0033(16)
N1 0.0229(14) 0.0155(14) 0.0141(14) 0.0008(12) 0.0013(11) 0.0008(12)
O1 0.0223(11) 0.0150(11) 0.0162(12) -0.0003(9) -0.0010(9) 0.0022(10)
O2 0.0389(15) 0.0213(14) 0.0149(12) -0.0021(9) -0.0010(11) 0.0052(10)
Pd1 0.01921(19) 0.00880(19) 0.00964(19) 0.00047(11) 0.00063(12) 0.00001(12)
O3 0.0503(18) 0.0234(15) 0.0219(15) 0.0069(12) 0.0102(12) 0.0126(15)

_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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.525(5) . ?
C1 N1 1.484(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.550(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.522(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.489(4) . ?
C5 C6 1.510(5) . ?
C5 O1 1.282(4) . ?
C5 O2 1.243(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N1 H1 0.81(5) . ?
N1 Pd1 2.043(3) . ?
O1 Pd1 2.015(2) . ?
Pd1 N1 2.043(3) 7_546 ?
Pd1 O1 2.015(2) 7_546 ?
O3 H3C 0.83(6) . ?
O3 H3D 0.71(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
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
N1 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
N1 C1 C2 104.7(3) . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C1 C2 C3 105.0(3) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 105.3(3) . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C4 C3 105.4(3) . . ?
N1 C4 H4A 110.7 . . ?
N1 C4 H4B 110.7 . . ?
O1 C5 C6 115.2(3) . . ?
O2 C5 C6 120.4(3) . . ?
O2 C5 O1 124.4(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 N1 C4 104.4(3) . . ?
C1 N1 H1 106(3) . . ?
C1 N1 Pd1 115.9(2) . . ?
C4 N1 H1 111(3) . . ?
C4 N1 Pd1 115.2(2) . . ?
Pd1 N1 H1 103(3) . . ?
C5 O1 Pd1 118.2(2) . . ?
N1 Pd1 N1 180.0 . 7_546 ?
O1 Pd1 N1 89.86(11) 7_546 . ?
O1 Pd1 N1 89.86(11) . 7_546 ?
O1 Pd1 N1 90.14(11) . . ?
O1 Pd1 N1 90.14(11) 7_546 7_546 ?
O1 Pd1 O1 180.0 7_546 . ?
H3C O3 H3D 104(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3C O2 0.83(6) 1.94(6) 2.769(4) 174(5) 4
O3 H3D O2 0.71(6) 2.15(6) 2.862(4) 172(5) 1_565

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
C1 C2 C3 C4 3.7(4) . . . . ?
C2 C1 N1 C4 38.9(3) . . . . ?
C2 C1 N1 Pd1 166.7(2) . . . . ?
C2 C3 C4 N1 19.9(4) . . . . ?
C3 C4 N1 C1 -36.6(4) . . . . ?
C3 C4 N1 Pd1 -164.8(2) . . . . ?
C6 C5 O1 Pd1 -168.6(2) . . . . ?
N1 C1 C2 C3 -25.9(4) . . . . ?
O2 C5 O1 Pd1 10.3(4) . . . . ?

_shelx_res_file                  
;
TITL ijsf1464a in Cc
CELL 1.54184 17.140547 6.10222 16.069432 90 90.1398 90
ZERR 4 0.000577 0.000169 0.000487 0 0.0029 0
LATT 7
SYMM -X,+Y,0.5-Z

SFAC C H N O Pd
UNIT 48 112 8 24 4
EQIV $1 +X,1+Y,+Z
EQIV $2 0.5-X,0.5+Y,0.5-Z

L.S. 9
PLAN  20
HTAB O3 O2_$1
HTAB O3 O2_$2
MORE -1
BOND $H
CONF
fmap 2 53
acta
REM <HKL>C:/Users/adria_000/Documents/XRD/ijsf1464a/struct/olex2_ijsf1464a/ijs
REM f1464a.hkl</HKL>

WGHT    0.039300    4.733700
FVAR       3.86225
C1    1    0.371141    0.105145    0.493389    11.00000    0.02805    0.01520 =
         0.02229   -0.00199   -0.00017   -0.00223
AFIX  23
H1A   2    0.396142    0.019915    0.536871    11.00000   -1.20000
H1B   2    0.339953    0.219353    0.518922    11.00000   -1.20000
AFIX   0
C2    1    0.431652    0.203295    0.434813    11.00000    0.02606    0.01733 =
         0.03678    0.00315    0.00384   -0.00169
AFIX  23
H2A   2    0.481290    0.221871    0.463061    11.00000   -1.20000
H2B   2    0.414428    0.344572    0.414080    11.00000   -1.20000
AFIX   0
C3    1    0.438986    0.035838    0.362693    11.00000    0.02899    0.02610 =
         0.02708    0.00756    0.00845    0.00118
AFIX  23
H3A   2    0.428317    0.105479    0.309610    11.00000   -1.20000
H3B   2    0.491010   -0.026579    0.361230    11.00000   -1.20000
AFIX   0
C4    1    0.378589   -0.140344    0.381057    11.00000    0.03212    0.01901 =
         0.02042   -0.00238    0.00891    0.00036
AFIX  23
H4A   2    0.352487   -0.186063    0.330321    11.00000   -1.20000
H4B   2    0.402999   -0.267265    0.406473    11.00000   -1.20000
AFIX   0
C5    1    0.148923   -0.133655    0.365600    11.00000    0.02352    0.01188 =
         0.01850    0.00267   -0.00022   -0.00177
C6    1    0.087324    0.009775    0.326067    11.00000    0.02904    0.02327 =
         0.02665    0.00316   -0.00686    0.00334
AFIX 137
H6A   2    0.042607    0.017023    0.361817    11.00000   -1.50000
H6B   2    0.072294   -0.051015    0.273311    11.00000   -1.50000
H6C   2    0.107917    0.154482    0.317945    11.00000   -1.50000
AFIX   0
N1    3    0.322182   -0.036977    0.439474    11.00000    0.02287    0.01554 =
         0.01407    0.00082    0.00128    0.00076
H1    2    0.292276    0.043792    0.415191    11.00000    0.02932
O1    4    0.156734   -0.111116    0.444514    11.00000    0.02229    0.01500 =
         0.01615   -0.00029   -0.00097    0.00217
O2    4    0.188711   -0.259605    0.322190    11.00000    0.03886    0.02126 =
         0.01488   -0.00209   -0.00099    0.00520
PD1   5    0.250000   -0.250000    0.500000    10.50000    0.01921    0.00880 =
         0.00964    0.00047    0.00063    0.00001

O3    4    0.256572    0.313662    0.337405    11.00000    0.05026    0.02336 =
         0.02186    0.00692    0.01019    0.01261
H3C   2    0.273650    0.301182    0.289343    11.00000    0.04386
H3D   2    0.238056    0.418203    0.337822    11.00000    0.03502
HKLF 4

REM  ijsf1464a in Cc
REM R1 =  0.0290 for    1307 Fo > 4sig(Fo)  and  0.0335 for all    1496 data
REM    110 parameters refined using      0 restraints

END

WGHT      0.0393      4.7337

REM Highest difference peak  1.645,  deepest hole -0.760,  1-sigma level  0.099
Q1    1   0.2994 -0.2459  0.5133  11.00000  0.05    1.64
Q2    1   0.1197 -0.2421  0.4863  11.00000  0.05    0.47
Q3    1   0.1547 -0.2839  0.4378  11.00000  0.05    0.46
Q4    1   0.1981 -0.1035  0.4421  11.00000  0.05    0.43
Q5    1   0.2469 -0.0940  0.5076  11.00000  0.05    0.41
Q6    1   0.3164 -0.2542  0.3248  11.00000  0.05    0.41
Q7    1   0.1448 -0.1457  0.4928  11.00000  0.05    0.39
Q8    1   0.2715 -0.2656  0.4355  11.00000  0.05    0.36
Q9    1   0.2815 -0.0529  0.5014  11.00000  0.05    0.34
Q10   1   0.1019 -0.0934  0.4380  11.00000  0.05    0.31
Q11   1   0.3483 -0.0932  0.4168  11.00000  0.05    0.30
Q12   1   0.3022 -0.1141  0.4564  11.00000  0.05    0.27
Q13   1   0.3572 -0.0265  0.4805  11.00000  0.05    0.26
Q14   1   0.0552 -0.2238  0.3177  11.00000  0.05    0.26
Q15   1   0.2497  0.1631  0.3407  11.00000  0.05    0.25
Q16   1   0.0732 -0.1120  0.4721  11.00000  0.05    0.25
Q17   1   0.4382  0.1241  0.3979  11.00000  0.05    0.25
Q18   1   0.3749  0.3653  0.4844  11.00000  0.05    0.25
Q19   1   0.4077  0.1091  0.4674  11.00000  0.05    0.24
Q20   1   0.4673  0.0574  0.3374  11.00000  0.05    0.24
;
_shelx_res_checksum              71854
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 0 0.0212 -1.0004 -0.0003 0.0007 0.0893 0.0004 -0.0100
1 0 0 0.0152 1.0004 0.0003 -0.0007 -0.0893 -0.0004 0.0100
0 0 -1 0.0393 -0.0010 0.0001 -0.9999 0.0106 0.0169 0.0938
0 0 1 0.0570 0.0010 -0.0001 0.9999 -0.0106 -0.0169 -0.0938
0 4 1 0.0394 0.0034 4.0022 1.0008 -0.0345 0.9774 -0.2704
0 -1 -1 0.0648 -0.0016 -1.0004 -1.0001 0.0166 -0.2316 0.1379

_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_ijsf1402
_database_code_depnum_ccdc_archive 'CCDC 1863216'
_audit_update_record             
;
2018-08-21 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_audit_creation_date             2014-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H32 N2 O4 Pd'
_chemical_formula_sum            'C16 H32 N2 O4 Pd'
_chemical_formula_weight         422.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H32 N2 O4 Pd1'
_chemical_oxdiff_usercomment     "Joshuaa's JTWB-4-193"
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      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                   6.0767(4)
_cell_length_b                   7.1046(4)
_cell_length_c                   10.4577(5)
_cell_angle_alpha                89.399(4)
_cell_angle_beta                 84.578(5)
_cell_angle_gamma                86.939(5)
_cell_volume                     448.82(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5162
_cell_measurement_temperature    110.10(14)
_cell_measurement_theta_max      32.0550
_cell_measurement_theta_min      3.4830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'yellowish colourless'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method DCM/pentane
_exptl_crystal_size_max          0.2829
_exptl_crystal_size_mid          0.1162
_exptl_crystal_size_min          0.0986
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8212
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.081
_diffrn_reflns_theta_min         2.868
_diffrn_ambient_temperature      110.10(14)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1105634000
_diffrn_orient_matrix_UB_12      -0.0248808000
_diffrn_orient_matrix_UB_13      -0.0042481000
_diffrn_orient_matrix_UB_21      0.0195544000
_diffrn_orient_matrix_UB_22      -0.0022973000
_diffrn_orient_matrix_UB_23      -0.0679289000
_diffrn_orient_matrix_UB_31      0.0343367000
_diffrn_orient_matrix_UB_32      -0.0968077000
_diffrn_orient_matrix_UB_33      0.0030895000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2912
_reflns_number_total             2927
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.606
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.081
_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)+(0.0338P)²+0.1374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0645
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8744(3) 0.1238(3) 0.62188(16) 0.0156(3) Uani 1 1 d . . . . .
C2 C 1.0223(3) 0.2822(3) 0.64797(19) 0.0188(3) Uani 1 1 d . . . . .
H2A H 1.1640 0.2645 0.5953 0.028 Uiso 1 1 calc GR . . . .
H2B H 1.0484 0.2809 0.7390 0.028 Uiso 1 1 calc GR . . . .
H2C H 0.9500 0.4035 0.6264 0.028 Uiso 1 1 calc GR . . . .
C3 C 0.4975(3) 0.3271(2) 0.33453(17) 0.0166(3) Uani 1 1 d . . . . .
H3A H 0.5698 0.3959 0.3995 0.020 Uiso 1 1 calc R . . . .
H3B H 0.3387 0.3228 0.3654 0.020 Uiso 1 1 calc R . . . .
C4 C 0.5163(3) 0.4400(3) 0.20958(18) 0.0186(3) Uani 1 1 d . . . . .
H4A H 0.4914 0.5754 0.2309 0.022 Uiso 1 1 calc R . . . .
H4B H 0.3956 0.4058 0.1584 0.022 Uiso 1 1 calc R . . . .
C5 C 0.7350(3) 0.4143(3) 0.12537(18) 0.0189(3) Uani 1 1 d . . . . .
H5A H 0.7604 0.5309 0.0746 0.023 Uiso 1 1 calc R . . . .
H5B H 0.8572 0.3951 0.1811 0.023 Uiso 1 1 calc R . . . .
C6 C 0.7397(3) 0.2482(3) 0.03420(17) 0.0178(3) Uani 1 1 d . . . . .
H6A H 0.8722 0.2536 -0.0283 0.021 Uiso 1 1 calc R . . . .
H6B H 0.6077 0.2610 -0.0146 0.021 Uiso 1 1 calc R . . . .
C7 C 0.7435(3) 0.0555(2) 0.10062(16) 0.0147(3) Uani 1 1 d . . . . .
H7A H 0.7336 -0.0422 0.0349 0.018 Uiso 1 1 calc R . . . .
H7B H 0.8884 0.0339 0.1359 0.018 Uiso 1 1 calc R . . . .
C8 C 0.5617(3) 0.0276(2) 0.20871(16) 0.0126(3) Uani 1 1 d . . . . .
H8A H 0.4176 0.0713 0.1790 0.015 Uiso 1 1 calc R . . . .
H8B H 0.5554 -0.1086 0.2286 0.015 Uiso 1 1 calc R . . . .
N1 N 0.5954(2) 0.13026(19) 0.32783(13) 0.0110(2) Uani 1 1 d . . . . .
H1 H 0.741(4) 0.136(3) 0.333(2) 0.016(6) Uiso 1 1 d . . . . .
O1 O 0.6948(2) 0.18105(17) 0.57443(12) 0.0125(2) Uani 1 1 d . . . . .
O2 O 0.9270(2) -0.04207(19) 0.64665(13) 0.0188(3) Uani 1 1 d . . . . .
Pd1 Pd 0.5000 0.0000 0.5000 0.00913(6) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0147(7) 0.0204(8) 0.0112(7) -0.0029(6) 0.0011(6) -0.0015(6)
C2 0.0153(8) 0.0195(8) 0.0224(9) -0.0046(7) -0.0049(7) -0.0036(6)
C3 0.0259(9) 0.0105(7) 0.0122(7) 0.0004(6) 0.0016(6) 0.0029(6)
C4 0.0267(9) 0.0124(8) 0.0159(8) 0.0025(6) -0.0002(7) 0.0020(7)
C5 0.0263(9) 0.0150(8) 0.0154(8) 0.0017(6) 0.0005(7) -0.0058(7)
C6 0.0220(8) 0.0184(8) 0.0125(8) 0.0020(6) 0.0012(6) -0.0030(7)
C7 0.0172(8) 0.0154(8) 0.0109(7) -0.0010(6) 0.0001(6) 0.0010(6)
C8 0.0158(7) 0.0129(7) 0.0093(7) -0.0001(5) -0.0012(5) -0.0021(6)
N1 0.0138(6) 0.0107(6) 0.0085(6) -0.0003(5) -0.0006(5) -0.0012(5)
O1 0.0121(5) 0.0128(5) 0.0128(5) -0.0025(4) -0.0027(4) -0.0003(4)
O2 0.0175(6) 0.0195(6) 0.0193(6) 0.0010(5) -0.0019(5) 0.0012(5)
Pd1 0.00953(8) 0.01041(9) 0.00752(8) -0.00043(5) -0.00136(5) -0.00016(6)

_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 1.520(2) . ?
C1 O1 1.286(2) . ?
C1 O2 1.236(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.524(2) . ?
C3 N1 1.490(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.527(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.529(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.523(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 N1 1.486(2) . ?
N1 H1 0.89(3) . ?
N1 Pd1 2.0638(14) . ?
O1 Pd1 2.0050(12) . ?
Pd1 N1 2.0638(14) 2_656 ?
Pd1 O1 2.0050(12) 2_656 ?

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 C1 C2 113.52(15) . . ?
O2 C1 C2 121.30(16) . . ?
O2 C1 O1 125.17(17) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
N1 C3 H3A 108.2 . . ?
N1 C3 H3B 108.2 . . ?
N1 C3 C4 116.15(14) . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
C3 C4 C5 116.36(16) . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.77(16) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C5 C6 C7 114.24(15) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C6 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 C6 116.07(15) . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
N1 C8 C7 113.16(14) . . ?
N1 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C3 N1 H1 107.2(15) . . ?
C3 N1 Pd1 107.34(10) . . ?
C8 N1 C3 114.77(13) . . ?
C8 N1 H1 108.7(16) . . ?
C8 N1 Pd1 116.84(10) . . ?
Pd1 N1 H1 100.7(16) . . ?
C1 O1 Pd1 121.42(11) . . ?
N1 Pd1 N1 180.0 . 2_656 ?
O1 Pd1 N1 84.48(5) . . ?
O1 Pd1 N1 95.52(5) 2_656 . ?
O1 Pd1 N1 95.52(5) . 2_656 ?
O1 Pd1 N1 84.48(5) 2_656 2_656 ?
O1 Pd1 O1 180.0 . 2_656 ?

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
C2 C1 O1 Pd1 168.05(11) . . . . ?
C3 C4 C5 C6 86.8(2) . . . . ?
C4 C3 N1 C8 -38.9(2) . . . . ?
C4 C3 N1 Pd1 -170.63(13) . . . . ?
C4 C5 C6 C7 -69.0(2) . . . . ?
C5 C6 C7 C8 53.3(2) . . . . ?
C6 C7 C8 N1 -73.55(19) . . . . ?
C7 C8 N1 C3 88.63(18) . . . . ?
C7 C8 N1 Pd1 -144.40(11) . . . . ?
N1 C3 C4 C5 -40.0(2) . . . . ?
O2 C1 O1 Pd1 -12.7(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 1 0 0.0581 0.0000 1.0000 0.0000 -0.0249 -0.0023 -0.0968
0 -1 0 0.0581 -0.0000 -1.0000 -0.0000 0.0249 0.0023 0.0968
1 1 0 0.1151 1.0000 1.0000 0.0000 -0.1354 0.0173 -0.0625
0 0 1 0.0493 -0.0000 -0.0000 1.0000 -0.0042 -0.0679 0.0031
0 0 -1 0.0493 0.0000 0.0000 -1.0000 0.0042 0.0679 -0.0031
0 1 -3 0.0573 0.0000 1.0000 -3.0000 -0.0121 0.2015 -0.1061
1 0 0 0.1438 1.0000 -0.0000 0.0000 -0.1106 0.0196 0.0343
-2 0 -3 0.1105 -2.0000 0.0000 -3.0000 0.2339 0.1647 -0.0779
2 1 3 0.1051 2.0000 1.0000 3.0000 -0.2588 -0.1670 -0.0189
0 3 2 0.0551 0.0000 3.0000 2.0000 -0.0831 -0.1427 -0.2842
1 -1 3 0.0821 1.0000 -1.0000 3.0000 -0.0984 -0.1819 0.1404
0 -1 -3 0.0581 0.0000 -1.0000 -3.0000 0.0376 0.2061 0.0875
-1 -1 4 0.0859 -1.0000 -1.0000 4.0000 0.1185 -0.2890 0.0748
1 1 -4 0.0728 1.0000 1.0000 -4.0000 -0.1185 0.2890 -0.0748
-2 0 1 0.1245 -2.0000 0.0000 1.0000 0.2169 -0.1070 -0.0656
-1 0 -4 0.0710 -1.0000 0.0000 -4.0000 0.1276 0.2522 -0.0467
1 1 -1 0.0964 1.0000 1.0000 -1.0000 -0.1312 0.0852 -0.0656

####################################################################### 
# 
# 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_ijsf1470
_database_code_depnum_ccdc_archive 'CCDC 1863217'
_audit_update_record             
;
2018-08-21 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_audit_creation_date             2014-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H36 N2 O4 Pd'
_chemical_formula_sum            'C18 H36 N2 O4 Pd'
_chemical_formula_weight         450.89
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H36 N2 O4 Pd1'
_chemical_oxdiff_usercomment     'Joshua Bray JTWB-5-324'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.49848(14)
_cell_length_b                   9.61025(19)
_cell_length_c                   14.3500(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.4862(18)
_cell_angle_gamma                90
_cell_volume                     1033.12(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      32.0590
_cell_measurement_theta_min      3.8950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.3156
_exptl_crystal_size_mid          0.2728
_exptl_crystal_size_min          0.1575
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6182
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.164
_diffrn_reflns_theta_min         3.448
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   67.00   1.0000    2.6300
omega____ theta____ kappa____ phi______ frames
    -       25.4797  -99.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   64.00   1.0000    2.6300
omega____ theta____ kappa____ phi______ frames
    -       25.4797  -99.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   68.00   1.0000    2.6300
omega____ theta____ kappa____ phi______ frames
    -       25.4797  -19.0000  150.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0884126000
_diffrn_orient_matrix_UB_12      -0.0159194000
_diffrn_orient_matrix_UB_13      0.0159900000
_diffrn_orient_matrix_UB_21      -0.0168232000
_diffrn_orient_matrix_UB_22      -0.0718346000
_diffrn_orient_matrix_UB_23      -0.0081815000
_diffrn_orient_matrix_UB_31      0.0293368000
_diffrn_orient_matrix_UB_32      0.0070111000
_diffrn_orient_matrix_UB_33      -0.0460364000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2650
_reflns_number_total             3286
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.055
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.224
_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)+(0.0131P)²+0.7690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0722
_refine_special_details          
;
 The hydrogen atom on the nitrogen was found by difference map after refinement
 of all other atoms. All other hydrogen atoms were calculated and refined using
 a riding model.
;
_olex2_refinement_description    
;
;
_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
C1 C 0.3629(3) 0.2918(2) -0.01273(16) 0.0164(4) Uani 1 1 d . . . . .
C2 C 0.2576(3) 0.4050(3) 0.03241(17) 0.0218(5) Uani 1 1 d . . . . .
H2A H 0.1600 0.4327 -0.0090 0.033 Uiso 1 1 calc GR . . . .
H2B H 0.3337 0.4836 0.0454 0.033 Uiso 1 1 calc GR . . . .
H2C H 0.2120 0.3709 0.0896 0.033 Uiso 1 1 calc GR . . . .
C3 C 0.1678(3) -0.1060(3) 0.08022(16) 0.0197(5) Uani 1 1 d . . . . .
H3 H 0.1134 -0.0140 0.0714 0.024 Uiso 1 1 calc R . . . .
C4 C 0.0709(3) -0.1812(3) 0.15655(18) 0.0301(6) Uani 1 1 d . . . . .
H4A H -0.0555 -0.1860 0.1393 0.036 Uiso 1 1 calc R . . . .
H4B H 0.1157 -0.2756 0.1623 0.036 Uiso 1 1 calc R . . . .
C5 C 0.0960(4) -0.1079(4) 0.2498(2) 0.0374(7) Uani 1 1 d . . . . .
H5A H 0.0389 -0.0173 0.2466 0.045 Uiso 1 1 calc R . . . .
H5B H 0.0406 -0.1619 0.2978 0.045 Uiso 1 1 calc R . . . .
C6 C 0.2927(4) -0.0907(3) 0.27428(17) 0.0269(6) Uani 1 1 d . . . . .
H6A H 0.3461 -0.1817 0.2843 0.032 Uiso 1 1 calc R . . . .
H6B H 0.3074 -0.0387 0.3321 0.032 Uiso 1 1 calc R . . . .
C7 C 0.3895(3) -0.0154(3) 0.19836(16) 0.0200(5) Uani 1 1 d . . . . .
H7 H 0.3420 0.0794 0.1930 0.024 Uiso 1 1 calc R . . . .
C8 C 0.1477(3) -0.1845(3) -0.01101(17) 0.0236(5) Uani 1 1 d . . . . .
H8A H 0.1994 -0.1311 -0.0595 0.035 Uiso 1 1 calc GR . . . .
H8B H 0.0233 -0.1997 -0.0264 0.035 Uiso 1 1 calc GR . . . .
H8C H 0.2076 -0.2725 -0.0050 0.035 Uiso 1 1 calc GR . . . .
C9 C 0.5868(3) -0.0065(3) 0.22283(17) 0.0283(6) Uani 1 1 d . . . . .
H9A H 0.6365 -0.0986 0.2259 0.042 Uiso 1 1 calc GR . . . .
H9B H 0.6052 0.0384 0.2822 0.042 Uiso 1 1 calc GR . . . .
H9C H 0.6445 0.0462 0.1759 0.042 Uiso 1 1 calc GR . . . .
N1 N 0.3593(3) -0.0866(2) 0.10655(13) 0.0148(4) Uani 1 1 d . . . . .
H1 H 0.411(3) -0.159(3) 0.1111(16) 0.009(6) Uiso 1 1 d . . . . .
O1 O 0.3655(2) 0.17570(17) 0.02889(11) 0.0183(3) Uani 1 1 d . . . . .
O2 O 0.4372(3) 0.31938(19) -0.08515(12) 0.0284(4) Uani 1 1 d . . . . .
Pd1 Pd 0.5000 0.0000 0.0000 0.01228(6) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0136(10) 0.0154(11) 0.0201(11) -0.0010(9) -0.0009(8) -0.0006(9)
C2 0.0235(11) 0.0147(11) 0.0276(12) 0.0010(10) 0.0060(10) 0.0035(10)
C3 0.0145(10) 0.0201(12) 0.0246(12) 0.0032(10) 0.0035(9) 0.0012(9)
C4 0.0230(12) 0.0369(16) 0.0312(14) 0.0024(12) 0.0102(11) -0.0070(12)
C5 0.0328(15) 0.0486(19) 0.0325(15) -0.0015(14) 0.0194(12) -0.0061(15)
C6 0.0364(14) 0.0267(13) 0.0186(11) -0.0015(10) 0.0114(10) -0.0073(12)
C7 0.0275(11) 0.0163(11) 0.0168(10) -0.0034(9) 0.0068(9) -0.0027(10)
C8 0.0191(11) 0.0253(13) 0.0260(12) 0.0025(10) -0.0023(9) -0.0054(10)
C9 0.0331(13) 0.0353(15) 0.0165(11) -0.0013(11) 0.0006(9) -0.0104(14)
N1 0.0165(9) 0.0117(9) 0.0167(9) 0.0008(7) 0.0044(7) 0.0016(8)
O1 0.0190(8) 0.0150(8) 0.0213(8) 0.0003(7) 0.0068(6) 0.0022(7)
O2 0.0382(10) 0.0204(9) 0.0277(9) 0.0091(8) 0.0157(8) 0.0098(9)
Pd1 0.01494(11) 0.00947(10) 0.01258(11) 0.00096(9) 0.00252(7) -0.00010(10)

_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 1.507(3) . ?
C1 O1 1.266(3) . ?
C1 O2 1.229(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3 0.9800 . ?
C3 C4 1.523(3) . ?
C3 C8 1.513(3) . ?
C3 N1 1.481(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.517(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.511(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.518(3) . ?
C7 H7 0.9800 . ?
C7 C9 1.508(3) . ?
C7 N1 1.493(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N1 H1 0.80(3) . ?
N1 Pd1 2.0696(18) . ?
O1 Pd1 2.0191(16) . ?
Pd1 N1 2.0696(18) 3_655 ?
Pd1 O1 2.0191(16) 3_655 ?

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 C1 C2 115.53(19) . . ?
O2 C1 C2 118.2(2) . . ?
O2 C1 O1 126.2(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3 108.2 . . ?
C8 C3 H3 108.2 . . ?
C8 C3 C4 110.7(2) . . ?
N1 C3 H3 108.2 . . ?
N1 C3 C4 111.4(2) . . ?
N1 C3 C8 110.04(18) . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 111.7(2) . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 C4 109.8(2) . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C5 C6 C7 112.2(2) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7 108.4 . . ?
C9 C7 C6 110.8(2) . . ?
C9 C7 H7 108.4 . . ?
N1 C7 C6 110.8(2) . . ?
N1 C7 H7 108.4 . . ?
N1 C7 C9 109.95(19) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 N1 C7 113.04(18) . . ?
C3 N1 H1 111.6(18) . . ?
C3 N1 Pd1 112.46(14) . . ?
C7 N1 H1 105.9(18) . . ?
C7 N1 Pd1 113.89(14) . . ?
Pd1 N1 H1 98.8(17) . . ?
C1 O1 Pd1 129.64(14) . . ?
N1 Pd1 N1 180.0 . 3_655 ?
O1 Pd1 N1 84.79(7) . . ?
O1 Pd1 N1 95.21(7) . 3_655 ?
O1 Pd1 N1 84.79(7) 3_655 3_655 ?
O1 Pd1 N1 95.21(7) 3_655 . ?
O1 Pd1 O1 180.0 3_655 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.80(3) 1.96(3) 2.733(3) 162(2) 3_655

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
C2 C1 O1 Pd1 -175.49(15) . . . . ?
C3 C4 C5 C6 -55.0(3) . . . . ?
C4 C3 N1 C7 -54.2(3) . . . . ?
C4 C3 N1 Pd1 175.07(17) . . . . ?
C4 C5 C6 C7 55.4(3) . . . . ?
C5 C6 C7 C9 -177.1(2) . . . . ?
C5 C6 C7 N1 -54.8(3) . . . . ?
C6 C7 N1 C3 54.1(3) . . . . ?
C6 C7 N1 Pd1 -175.96(17) . . . . ?
C8 C3 C4 C5 177.4(2) . . . . ?
C8 C3 N1 C7 -177.4(2) . . . . ?
C8 C3 N1 Pd1 51.9(2) . . . . ?
C9 C7 N1 C3 176.8(2) . . . . ?
C9 C7 N1 Pd1 -53.2(2) . . . . ?
N1 C3 C4 C5 54.7(3) . . . . ?
O2 C1 O1 Pd1 4.5(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 1 1 0.0493 0.0000 1.0000 1.0000 0.0001 -0.0800 -0.0390
0 -1 0 0.0540 0.0000 -1.0000 0.0000 0.0159 0.0718 -0.0070
0 0 2 0.1563 0.0000 0.0000 2.0000 0.0320 -0.0164 -0.0921
0 0 -2 0.1563 -0.0000 -0.0000 -2.0000 -0.0320 0.0164 0.0921
-1 0 0 0.1244 -1.0000 -0.0000 -0.0000 -0.0884 0.0168 -0.0293
1 0 0 0.1484 1.0000 0.0000 0.0000 0.0884 -0.0168 0.0293
0 1 -1 0.1229 -0.0000 1.0000 -1.0000 -0.0319 -0.0637 0.0530
-1 -5 -2 0.0706 -1.0000 -5.0000 -2.0000 -0.0408 0.3924 0.0277
1 0 1 0.1244 1.0000 0.0000 1.0000 0.1044 -0.0250 -0.0167
1 0 -5 0.1593 1.0000 0.0000 -5.0000 0.0085 0.0241 0.2595
-2 0 5 0.1443 -2.0000 -0.0000 5.0000 -0.0969 -0.0073 -0.2889
2 -4 -5 0.1165 2.0000 -4.0000 -5.0000 0.1606 0.2946 0.2608

_iucr_refine_instructions_details 
;
TITL ijsf1470 in P21/c #14
CELL 0.71073 7.498476 9.610249 14.34998 90 92.4862 90
ZERR 2 0.000136 0.000186 0.000285 0 0.0018 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
 
SFAC C H N O Pd
UNIT 36 72 4 8 2
EQIV $1 1-X,-Y,-Z
 
L.S. 8
PLAN  25
HTAB N1 O2_$1
REM reset to P21/c #14
BOND $H
MORE -1
CONF
fmap 2
acta
REM <HKL>D:/frames/ijsf1470/struct/olex2_ijsf1470/ijsf1470.hkl</HKL>
 
WGHT    0.013100    0.769000
FVAR       6.81127
C1    1    0.362927    0.291834   -0.012732    11.00000    0.01355    0.01541 =
         0.02007   -0.00097   -0.00088   -0.00059
C2    1    0.257620    0.405008    0.032414    11.00000    0.02352    0.01474 =
         0.02760    0.00101    0.00605    0.00346
AFIX 137
H2A   2    0.160037    0.432677   -0.009002    11.00000   -1.50000
H2B   2    0.333722    0.483587    0.045439    11.00000   -1.50000
H2C   2    0.212010    0.370863    0.089566    11.00000   -1.50000
AFIX   0
C3    1    0.167761   -0.106019    0.080220    11.00000    0.01453    0.02015 =
         0.02464    0.00321    0.00349    0.00125
AFIX  13
H3    2    0.113374   -0.013976    0.071364    11.00000   -1.20000
AFIX   0
C4    1    0.070858   -0.181191    0.156545    11.00000    0.02304    0.03693 =
         0.03118    0.00245    0.01019   -0.00705
AFIX  23
H4A   2   -0.055493   -0.186038    0.139268    11.00000   -1.20000
H4B   2    0.115729   -0.275608    0.162278    11.00000   -1.20000
AFIX   0
C5    1    0.095956   -0.107883    0.249838    11.00000    0.03279    0.04856 =
         0.03252   -0.00154    0.01937   -0.00612
AFIX  23
H5A   2    0.038851   -0.017339    0.246650    11.00000   -1.20000
H5B   2    0.040630   -0.161926    0.297828    11.00000   -1.20000
AFIX   0
C6    1    0.292729   -0.090654    0.274281    11.00000    0.03637    0.02667 =
         0.01855   -0.00150    0.01143   -0.00734
AFIX  23
H6A   2    0.346142   -0.181664    0.284252    11.00000   -1.20000
H6B   2    0.307401   -0.038725    0.332069    11.00000   -1.20000
AFIX   0
C7    1    0.389523   -0.015376    0.198357    11.00000    0.02754    0.01630 =
         0.01677   -0.00340    0.00677   -0.00266
AFIX  13
H7    2    0.341991    0.079412    0.192985    11.00000   -1.20000
AFIX   0
C8    1    0.147693   -0.184500   -0.011006    11.00000    0.01913    0.02533 =
         0.02599    0.00248   -0.00226   -0.00538
AFIX 137
H8A   2    0.199378   -0.131139   -0.059537    11.00000   -1.50000
H8B   2    0.023323   -0.199652   -0.026352    11.00000   -1.50000
H8C   2    0.207643   -0.272518   -0.005024    11.00000   -1.50000
AFIX   0
C9    1    0.586850   -0.006538    0.222829    11.00000    0.03310    0.03532 =
         0.01648   -0.00135    0.00065   -0.01043
AFIX 137
H9A   2    0.636494   -0.098585    0.225897    11.00000   -1.50000
H9B   2    0.605187    0.038383    0.282226    11.00000   -1.50000
H9C   2    0.644466    0.046213    0.175940    11.00000   -1.50000
AFIX   0
N1    3    0.359292   -0.086562    0.106554    11.00000    0.01648    0.01165 =
         0.01665    0.00075    0.00442    0.00156
H1    2    0.410603   -0.159251    0.111089    11.00000    0.00942
O1    4    0.365471    0.175701    0.028894    11.00000    0.01904    0.01502 =
         0.02132    0.00033    0.00676    0.00215
O2    4    0.437250    0.319385   -0.085151    11.00000    0.03823    0.02042 =
         0.02769    0.00906    0.01574    0.00983
PD1   5    0.500000    0.000000    0.000000    10.50000    0.01494    0.00947 =
         0.01258    0.00096    0.00252   -0.00010
HKLF 4
 
REM  ijsf1470 in P21/c #14
REM R1 =  0.0342 for    2650 Fo > 4sig(Fo)  and  0.0460 for all    3286 data
REM    122 parameters refined using      0 restraints
 
END  
     
WGHT      0.0131      0.7690 

REM Highest difference peak  1.055,  deepest hole -0.574,  1-sigma level  0.092
Q1    1   0.6274  0.0014  0.0006  11.00000  0.05    1.06
Q2    1   0.3710  0.2376  0.0138  11.00000  0.05    0.51
Q3    1   0.5680  0.0219  0.0568  11.00000  0.05    0.47
Q4    1   0.0954 -0.1449  0.1950  11.00000  0.05    0.46
Q5    1   0.4808  0.0015  0.2159  11.00000  0.05    0.43
Q6    1   0.1096 -0.1374  0.1196  11.00000  0.05    0.43
Q7    1   0.5278  0.1710  0.0245  11.00000  0.05    0.43
Q8    1   0.2161  0.1821  0.0250  11.00000  0.05    0.42
Q9    1   0.4165  0.1623  0.0453  11.00000  0.05    0.39
Q10   1   0.2610  0.0962  0.1156  11.00000  0.05    0.34
Q11   1   0.0455 -0.1111  0.2753  11.00000  0.05    0.34
Q12   1   0.1212 -0.1509  0.0336  11.00000  0.05    0.33
Q13   1   0.3929  0.1805 -0.0169  11.00000  0.05    0.32
Q14   1  -0.2431 -0.1009  0.0840  11.00000  0.05    0.32
Q15   1   0.3280  0.1881  0.0721  11.00000  0.05    0.31
Q16   1   0.4555 -0.1375  0.0279  11.00000  0.05    0.31
Q17   1   0.4937 -0.0626  0.0715  11.00000  0.05    0.30
Q18   1   0.2829 -0.0607  0.0933  11.00000  0.05    0.29
Q19   1   0.5248 -0.0922  0.1106  11.00000  0.05    0.29
Q20   1   0.5488  0.2842 -0.0012  11.00000  0.05    0.28
Q21   1   0.3262 -0.1022 -0.0825  11.00000  0.05    0.28
Q22   1   0.1682 -0.0871  0.2729  11.00000  0.05    0.28
Q23   1   0.3595  0.2811 -0.0801  11.00000  0.05    0.28
Q24   1   0.6227 -0.0826  0.1075  11.00000  0.05    0.27
Q25   1   0.4818 -0.1622  0.4027  11.00000  0.05    0.27

REM The information below was added by Olex2.
REM
REM R1 = 0.0342 for 2650 Fo > 4sig(Fo) and 0.0460 for all 6436 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 1.06, deepest hole -0.57
REM Mean Shift 0, Max Shift 0.000.

REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0460
REM R1_gt = 0.0342
REM wR_ref = 0.0722
REM GOOF = 1.224
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 6436
REM Reflections_gt = 2650
REM Parameters = n/a
REM Hole = -0.57
REM Peak = 1.06
REM Flack = n/a

;
_olex2_exptl_crystal_mounting_method 'Oil on loop'
_olex2_submission_special_instructions 'No special instructions were received'
