# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_RDS594
_database_code_depnum_ccdc_archive 'CCDC 1900109'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Fujita38-2
_chemical_formula_moiety         'C14 H16 Br N O4'
_chemical_formula_sum            'C14 H16 Br N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         342.19
_chemical_absolute_configuration ad

_chemical_melting_point          ?

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

_cell_length_a                   9.6116(5)
_cell_length_b                   21.6883(12)
_cell_length_c                   7.1486(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1490.19(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.3177
_cell_measurement_theta_max      29.3942
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.087
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    2.770
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_process_details   
;
Mu From Formula
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.80

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            32573
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5

_refine_special_details          
;
;

_reflns_number_total             4721
_reflns_number_gt                4000
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0938
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_number_reflns         4721
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+2.6056P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.707
_refine_diff_density_min         -1.226
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1512 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(4)

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 786)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.44508(4) 0.24823(2) 1.12813(5) 0.02236(11) Uani d . . . 1 . .
O O1 0.6411(4) 0.35661(17) 1.3061(4) 0.0262(8) Uani d . . . 1 . .
O O2 0.7407(3) 0.42693(13) 1.1174(5) 0.0201(6) Uani d . . . 1 . .
O O3 0.4762(3) 0.13641(14) 0.4674(4) 0.0169(6) Uani d . . . 1 . .
O O4 0.5112(4) 0.05529(17) 0.2814(6) 0.0306(8) Uani d . . . 1 . .
N N1 0.6487(4) 0.31305(16) 0.6796(5) 0.0167(7) Uani d . . . 1 . .
H H1A 0.6707 0.3122 0.5601 0.02 Uiso calc U . R 1 . .
C C1 0.6920(4) 0.35621(19) 0.8027(6) 0.0154(8) Uani d . . . 1 . .
H H1 0.7497 0.3905 0.7736 0.018 Uiso calc U . R 1 . .
C C2 0.6393(4) 0.34263(19) 0.9777(6) 0.0141(8) Uani d . . . 1 . .
C C3 0.5579(4) 0.28854(18) 0.9525(6) 0.0155(7) Uani d . . . 1 . .
C C4 0.5649(4) 0.27046(18) 0.7683(6) 0.0158(7) Uani d . . . 1 . .
C C5 0.4984(4) 0.2183(2) 0.6782(6) 0.0168(8) Uani d . . . 1 . .
H H5 0.4073 0.2077 0.7184 0.02 Uiso calc U . R 1 . .
C C6 0.5551(4) 0.18441(18) 0.5441(6) 0.0154(7) Uani d . . . 1 . .
C C7 0.6954(4) 0.1853(2) 0.4525(6) 0.0180(8) Uani d . . . 1 . .
H H7A 0.7695 0.1948 0.5442 0.022 Uiso calc U . R 1 . .
H H7B 0.6987 0.216 0.35 0.022 Uiso calc U . R 1 . .
C C8 0.7102(4) 0.1191(2) 0.3764(8) 0.0228(9) Uani d . . . 1 . .
C C9 0.5597(5) 0.09829(19) 0.3618(6) 0.0203(8) Uani d . . . 1 . .
C C10 0.6705(4) 0.37491(19) 1.1508(6) 0.0157(8) Uani d . . . 1 . .
C C11 0.7860(5) 0.4633(2) 1.2778(6) 0.0194(8) Uani d . . . 1 . .
H H11A 0.791 0.4371 1.391 0.023 Uiso calc U . R 1 . .
H H11B 0.7195 0.4973 1.3018 0.023 Uiso calc U . R 1 . .
C C12 0.9282(5) 0.4890(2) 1.2315(7) 0.0285(10) Uani d . . . 1 . .
H H12A 0.9221 0.5143 1.1182 0.043 Uiso calc U . R 1 . .
H H12B 0.9933 0.4549 1.2105 0.043 Uiso calc U . R 1 . .
H H12C 0.9612 0.5144 1.3358 0.043 Uiso calc U . R 1 . .
C C13 0.7806(6) 0.1145(3) 0.1866(8) 0.0362(13) Uani d . . . 1 . .
H H13A 0.7766 0.0718 0.1422 0.054 Uiso calc U . R 1 . .
H H13B 0.8779 0.1274 0.1978 0.054 Uiso calc U . R 1 . .
H H13C 0.7325 0.1414 0.0974 0.054 Uiso calc U . R 1 . .
C C14 0.7817(5) 0.0774(3) 0.5205(9) 0.0336(12) Uani d . . . 1 . .
H H14A 0.7348 0.0815 0.6415 0.05 Uiso calc U . R 1 . .
H H14B 0.8794 0.0897 0.5335 0.05 Uiso calc U . R 1 . .
H H14C 0.7768 0.0345 0.4787 0.05 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C3 . 1.875(4) ?
O1 C10 . 1.213(5) ?
O2 C10 . 1.336(5) ?
O2 C11 . 1.458(5) ?
O3 C9 . 1.378(5) ?
O3 C6 . 1.400(5) ?
O4 C9 . 1.190(5) ?
N1 C1 . 1.351(6) ?
N1 C4 . 1.380(5) ?
N1 H1A . 0.88 ?
C1 C2 . 1.381(5) ?
C1 H1 . 0.95 ?
C2 C3 . 1.421(6) ?
C2 C10 . 1.453(6) ?
C3 C4 . 1.376(6) ?
C4 C5 . 1.450(6) ?
C5 C6 . 1.325(6) ?
C5 H5 . 0.95 ?
C6 C7 . 1.500(6) ?
C7 C8 . 1.543(6) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C13 . 1.519(7) ?
C8 C9 . 1.519(6) ?
C8 C14 . 1.532(7) ?
C11 C12 . 1.513(6) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O2 C11 . . 117.8(3) ?
C9 O3 C6 . . 110.2(3) ?
C1 N1 C4 . . 110.1(4) ?
C1 N1 H1A . . 124.9 ?
C4 N1 H1A . . 124.9 ?
N1 C1 C2 . . 109.2(4) ?
N1 C1 H1 . . 125.4 ?
C2 C1 H1 . . 125.4 ?
C1 C2 C3 . . 105.3(4) ?
C1 C2 C10 . . 126.3(4) ?
C3 C2 C10 . . 128.2(4) ?
C4 C3 C2 . . 109.2(4) ?
C4 C3 Br1 . . 122.4(3) ?
C2 C3 Br1 . . 128.2(3) ?
C3 C4 N1 . . 106.1(4) ?
C3 C4 C5 . . 128.8(4) ?
N1 C4 C5 . . 125.1(4) ?
C6 C5 C4 . . 124.9(4) ?
C6 C5 H5 . . 117.5 ?
C4 C5 H5 . . 117.5 ?
C5 C6 O3 . . 118.3(4) ?
C5 C6 C7 . . 132.7(4) ?
O3 C6 C7 . . 109.0(3) ?
C6 C7 C8 . . 103.0(3) ?
C6 C7 H7A . . 111.2 ?
C8 C7 H7A . . 111.2 ?
C6 C7 H7B . . 111.2 ?
C8 C7 H7B . . 111.2 ?
H7A C7 H7B . . 109.1 ?
C13 C8 C9 . . 110.1(4) ?
C13 C8 C14 . . 111.3(4) ?
C9 C8 C14 . . 107.4(4) ?
C13 C8 C7 . . 114.6(4) ?
C9 C8 C7 . . 102.3(3) ?
C14 C8 C7 . . 110.7(4) ?
O4 C9 O3 . . 120.4(4) ?
O4 C9 C8 . . 129.7(4) ?
O3 C9 C8 . . 109.8(3) ?
O1 C10 O2 . . 123.9(4) ?
O1 C10 C2 . . 125.0(4) ?
O2 C10 C2 . . 111.0(4) ?
O2 C11 C12 . . 107.3(4) ?
O2 C11 H11A . . 110.3 ?
C12 C11 H11A . . 110.3 ?
O2 C11 H11B . . 110.3 ?
C12 C11 H11B . . 110.3 ?
H11A C11 H11B . . 108.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C8 C13 H13A . . 109.5 ?
C8 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C8 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C8 C14 H14A . . 109.5 ?
C8 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C8 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C2 . . . . 0.9(5) ?
N1 C1 C2 C3 . . . . -1.1(5) ?
N1 C1 C2 C10 . . . . 174.8(4) ?
C1 C2 C3 C4 . . . . 1.0(5) ?
C10 C2 C3 C4 . . . . -174.8(4) ?
C1 C2 C3 Br1 . . . . -174.7(3) ?
C10 C2 C3 Br1 . . . . 9.5(7) ?
C2 C3 C4 N1 . . . . -0.5(5) ?
Br1 C3 C4 N1 . . . . 175.5(3) ?
C2 C3 C4 C5 . . . . -179.7(4) ?
Br1 C3 C4 C5 . . . . -3.7(7) ?
C1 N1 C4 C3 . . . . -0.2(5) ?
C1 N1 C4 C5 . . . . 179.0(4) ?
C3 C4 C5 C6 . . . . -143.2(5) ?
N1 C4 C5 C6 . . . . 37.7(7) ?
C4 C5 C6 O3 . . . . -178.3(4) ?
C4 C5 C6 C7 . . . . 3.1(8) ?
C9 O3 C6 C5 . . . . -167.0(4) ?
C9 O3 C6 C7 . . . . 11.9(5) ?
C5 C6 C7 C8 . . . . 156.6(5) ?
O3 C6 C7 C8 . . . . -22.0(5) ?
C6 C7 C8 C13 . . . . 141.8(4) ?
C6 C7 C8 C9 . . . . 22.7(5) ?
C6 C7 C8 C14 . . . . -91.4(4) ?
C6 O3 C9 O4 . . . . -178.4(4) ?
C6 O3 C9 C8 . . . . 3.9(5) ?
C13 C8 C9 O4 . . . . 43.2(7) ?
C14 C8 C9 O4 . . . . -78.0(7) ?
C7 C8 C9 O4 . . . . 165.4(5) ?
C13 C8 C9 O3 . . . . -139.4(4) ?
C14 C8 C9 O3 . . . . 99.3(4) ?
C7 C8 C9 O3 . . . . -17.2(5) ?
C11 O2 C10 O1 . . . . 0.9(6) ?
C11 O2 C10 C2 . . . . -177.1(3) ?
C1 C2 C10 O1 . . . . -167.7(5) ?
C3 C2 C10 O1 . . . . 7.3(7) ?
C1 C2 C10 O2 . . . . 10.2(6) ?
C3 C2 C10 O2 . . . . -174.8(4) ?
C10 O2 C11 C12 . . . . 142.3(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O1 1_554 0.88 2.07 2.833(5) 143.8 ?

####################################################################### 
# 
# 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_rds662
_database_code_depnum_ccdc_archive 'CCDC 1900118'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            GVR-DHDP-NaEt
_chemical_formula_moiety         'C25 H26 N2 O2'
_chemical_formula_sum            'C25 H26 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         386.48

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.7670(4)
_cell_length_b                   7.3416(2)
_cell_length_c                   18.1519(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.7904(10)
_cell_angle_gamma                90
_cell_volume                     2093.83(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6895
_cell_measurement_theta_min      2.2518
_cell_measurement_theta_max      25.4929
_cell_measurement_temperature    121.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      121.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            30616
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_full        27.11
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             4625
_reflns_number_gt                3389
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1264
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_number_reflns         4625
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+0.9485P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.317
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 786)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.65570(7) 0.75355(16) 0.16601(6) 0.0270(3) Uani d . . . 1 . .
O O2 0.51589(7) 0.72983(15) 0.18118(6) 0.0243(3) Uani d . . . 1 . .
N N1 0.66906(8) -0.07384(18) 0.36438(7) 0.0220(3) Uani d . . . 1 . .
N N2 0.66259(8) 0.26705(19) 0.29213(7) 0.0190(3) Uani d . . . 1 . .
H H2 0.7010(11) 0.192(3) 0.3148(9) 0.023 Uiso d U . . 1 . .
C C1 0.68953(11) -0.2044(2) 0.40973(9) 0.0236(4) Uani d . . . 1 . .
C C2 0.61451(11) -0.2870(2) 0.44631(9) 0.0243(4) Uani d . . . 1 . .
C C3 0.54098(11) -0.2237(2) 0.39134(9) 0.0243(4) Uani d . . . 1 . .
H H3A 0.525 -0.3191 0.3542 0.029 Uiso calc U . R 1 . .
H H3B 0.4903 -0.1899 0.4171 0.029 Uiso calc U . R 1 . .
C C4 0.57909(10) -0.0596(2) 0.35620(9) 0.0211(3) Uani d . . . 1 . .
C C5 0.53820(10) 0.0793(2) 0.32141(9) 0.0212(3) Uani d . . . 1 . .
H H5 0.4778 0.0746 0.3179 0.025 Uiso calc U . R 1 . .
C C6 0.57604(10) 0.2362(2) 0.28848(9) 0.0198(3) Uani d . . . 1 . .
C C7 0.53677(10) 0.3797(2) 0.25009(9) 0.0204(3) Uani d . . . 1 . .
C C8 0.60324(10) 0.4990(2) 0.22967(8) 0.0188(3) Uani d . . . 1 . .
C C9 0.67932(10) 0.4236(2) 0.25745(8) 0.0192(3) Uani d . . . 1 . .
H H9 0.7342 0.4735 0.2529 0.023 Uiso calc U . R 1 . .
C C10 0.77866(12) -0.2647(3) 0.42685(11) 0.0334(4) Uani d . . . 1 . .
H H10A 0.7849 -0.3903 0.4098 0.05 Uiso calc U . R 1 . .
H H10B 0.7932 -0.2587 0.4804 0.05 Uiso calc U . R 1 . .
H H10C 0.8169 -0.1849 0.4017 0.05 Uiso calc U . R 1 . .
C C11 0.62043(12) -0.4923(2) 0.45739(10) 0.0328(4) Uani d . . . 1 . .
H H11A 0.6251 -0.5519 0.4096 0.049 Uiso calc U . R 1 . .
H H11B 0.5693 -0.5359 0.479 0.049 Uiso calc U . R 1 . .
H H11C 0.6708 -0.5212 0.4907 0.049 Uiso calc U . R 1 . .
C C12 0.60923(13) -0.1902(3) 0.52119(9) 0.0327(4) Uani d . . . 1 . .
H H12A 0.6614 -0.2136 0.553 0.049 Uiso calc U . R 1 . .
H H12B 0.5601 -0.2366 0.5451 0.049 Uiso calc U . R 1 . .
H H12C 0.6028 -0.0588 0.513 0.049 Uiso calc U . R 1 . .
C C13 0.59664(10) 0.6716(2) 0.18952(8) 0.0193(3) Uani d . . . 1 . .
C C14 0.49736(11) 0.8937(2) 0.13879(10) 0.0254(4) Uani d . . . 1 . .
H H14A 0.5247 0.89 0.0917 0.031 Uiso calc U . R 1 . .
H H14B 0.5179 1.0027 0.167 0.031 Uiso calc U . R 1 . .
C C15 0.40296(13) 0.8973(3) 0.12479(16) 0.0594(7) Uani d . . . 1 . .
H H15A 0.3859 1.0036 0.0944 0.089 Uiso calc U . R 1 . .
H H15B 0.3772 0.9046 0.172 0.089 Uiso calc U . R 1 . .
H H15C 0.3837 0.7859 0.0987 0.089 Uiso calc U . R 1 . .
C C16 0.44295(10) 0.3948(2) 0.23523(9) 0.0222(4) Uani d . . . 1 . .
C C17 0.39207(11) 0.4139(2) 0.29253(10) 0.0270(4) Uani d . . . 1 . .
H H17 0.4184 0.4259 0.3413 0.032 Uiso calc U . R 1 . .
C C18 0.30322(12) 0.4165(3) 0.28219(12) 0.0366(5) Uani d . . . 1 . .
H H18 0.2702 0.4316 0.3232 0.044 Uiso calc U . R 1 . .
C C19 0.26426(12) 0.3971(3) 0.21217(12) 0.0387(5) Uani d . . . 1 . .
H H19 0.2039 0.3967 0.2051 0.046 Uiso calc U . R 1 . .
C C20 0.31215(11) 0.3779(2) 0.15078(10) 0.0284(4) Uani d . . . 1 . .
C C21 0.40358(11) 0.3797(2) 0.16166(10) 0.0249(4) Uani d . . . 1 . .
C C22 0.45058(12) 0.3655(2) 0.09852(9) 0.0256(4) Uani d . . . 1 . .
H H22 0.511 0.3659 0.1043 0.031 Uiso calc U . R 1 . .
C C23 0.40936(14) 0.3511(3) 0.02954(11) 0.0374(5) Uani d . . . 1 . .
H H23 0.4419 0.3465 -0.0122 0.045 Uiso calc U . R 1 . .
C C24 0.32096(15) 0.3428(3) 0.01856(12) 0.0459(6) Uani d . . . 1 . .
H H24 0.2937 0.3285 -0.0298 0.055 Uiso calc U . R 1 . .
C C25 0.27465(14) 0.3555(3) 0.07755(12) 0.0399(5) Uani d . . . 1 . .
H H25 0.2144 0.3492 0.0697 0.048 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.2157(19) ?
O2 C13 . 1.3396(19) ?
O2 C14 . 1.4450(19) ?
N1 C1 . 1.287(2) ?
N1 C4 . 1.418(2) ?
N2 C9 . 1.347(2) ?
N2 C6 . 1.379(2) ?
N2 H2 . 0.891(18) ?
C1 C10 . 1.481(2) ?
C1 C2 . 1.529(2) ?
C2 C11 . 1.522(2) ?
C2 C3 . 1.537(2) ?
C2 C12 . 1.542(2) ?
C3 C4 . 1.511(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.336(2) ?
C5 C6 . 1.449(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.381(2) ?
C7 C8 . 1.438(2) ?
C7 C16 . 1.485(2) ?
C8 C9 . 1.378(2) ?
C8 C13 . 1.461(2) ?
C9 H9 . 0.95 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C14 C15 . 1.489(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 C17 . 1.373(2) ?
C16 C21 . 1.429(2) ?
C17 C18 . 1.398(2) ?
C17 H17 . 0.95 ?
C18 C19 . 1.372(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.404(3) ?
C19 H19 . 0.95 ?
C20 C25 . 1.419(3) ?
C20 C21 . 1.439(2) ?
C21 C22 . 1.420(2) ?
C22 C23 . 1.366(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.393(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.349(3) ?
C24 H24 . 0.95 ?
C25 H25 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O2 C14 . . 118.29(13) ?
C1 N1 C4 . . 108.50(14) ?
C9 N2 C6 . . 110.43(13) ?
C9 N2 H2 . . 126.0(12) ?
C6 N2 H2 . . 123.6(12) ?
N1 C1 C10 . . 122.65(15) ?
N1 C1 C2 . . 114.28(14) ?
C10 C1 C2 . . 123.04(15) ?
C11 C2 C1 . . 114.12(14) ?
C11 C2 C3 . . 114.81(15) ?
C1 C2 C3 . . 99.63(13) ?
C11 C2 C12 . . 110.31(14) ?
C1 C2 C12 . . 107.50(14) ?
C3 C2 C12 . . 109.84(14) ?
C4 C3 C2 . . 102.12(13) ?
C4 C3 H3A . . 111.3 ?
C2 C3 H3A . . 111.3 ?
C4 C3 H3B . . 111.3 ?
C2 C3 H3B . . 111.3 ?
H3A C3 H3B . . 109.2 ?
C5 C4 N1 . . 123.02(15) ?
C5 C4 C3 . . 127.92(15) ?
N1 C4 C3 . . 109.05(13) ?
C4 C5 C6 . . 127.04(15) ?
C4 C5 H5 . . 116.5 ?
C6 C5 H5 . . 116.5 ?
N2 C6 C7 . . 107.41(14) ?
N2 C6 C5 . . 123.39(14) ?
C7 C6 C5 . . 129.19(15) ?
C6 C7 C8 . . 106.80(14) ?
C6 C7 C16 . . 123.13(14) ?
C8 C7 C16 . . 130.07(14) ?
C9 C8 C7 . . 106.96(14) ?
C9 C8 C13 . . 123.68(14) ?
C7 C8 C13 . . 129.33(14) ?
N2 C9 C8 . . 108.39(14) ?
N2 C9 H9 . . 125.8 ?
C8 C9 H9 . . 125.8 ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C2 C12 H12A . . 109.5 ?
C2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O1 C13 O2 . . 123.43(15) ?
O1 C13 C8 . . 125.43(14) ?
O2 C13 C8 . . 111.14(13) ?
O2 C14 C15 . . 105.07(14) ?
O2 C14 H14A . . 110.7 ?
C15 C14 H14A . . 110.7 ?
O2 C14 H14B . . 110.7 ?
C15 C14 H14B . . 110.7 ?
H14A C14 H14B . . 108.8 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C21 . . 118.70(15) ?
C17 C16 C7 . . 120.41(15) ?
C21 C16 C7 . . 120.80(15) ?
C16 C17 C18 . . 122.83(17) ?
C16 C17 H17 . . 118.6 ?
C18 C17 H17 . . 118.6 ?
C19 C18 C17 . . 119.28(18) ?
C19 C18 H18 . . 120.4 ?
C17 C18 H18 . . 120.4 ?
C18 C19 C20 . . 121.11(18) ?
C18 C19 H19 . . 119.4 ?
C20 C19 H19 . . 119.4 ?
C19 C20 C25 . . 123.06(18) ?
C19 C20 C21 . . 119.28(16) ?
C25 C20 C21 . . 117.66(18) ?
C22 C21 C16 . . 123.01(15) ?
C22 C21 C20 . . 118.23(16) ?
C16 C21 C20 . . 118.75(16) ?
C23 C22 C21 . . 120.35(17) ?
C23 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C22 C23 C24 . . 121.9(2) ?
C22 C23 H23 . . 119.0 ?
C24 C23 H23 . . 119.0 ?
C25 C24 C23 . . 119.01(19) ?
C25 C24 H24 . . 120.5 ?
C23 C24 H24 . . 120.5 ?
C24 C25 C20 . . 122.76(19) ?
C24 C25 H25 . . 118.6 ?
C20 C25 H25 . . 118.6 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C10 . . . . 175.71(15) ?
C4 N1 C1 C2 . . . . -6.35(19) ?
N1 C1 C2 C11 . . . . 142.86(16) ?
C10 C1 C2 C11 . . . . -39.2(2) ?
N1 C1 C2 C3 . . . . 20.02(18) ?
C10 C1 C2 C3 . . . . -162.05(16) ?
N1 C1 C2 C12 . . . . -94.46(17) ?
C10 C1 C2 C12 . . . . 83.5(2) ?
C11 C2 C3 C4 . . . . -145.90(14) ?
C1 C2 C3 C4 . . . . -23.55(15) ?
C12 C2 C3 C4 . . . . 89.12(15) ?
C1 N1 C4 C5 . . . . 169.93(15) ?
C1 N1 C4 C3 . . . . -10.92(18) ?
C2 C3 C4 C5 . . . . -158.24(16) ?
C2 C3 C4 N1 . . . . 22.66(16) ?
N1 C4 C5 C6 . . . . -1.5(3) ?
C3 C4 C5 C6 . . . . 179.56(15) ?
C9 N2 C6 C7 . . . . -0.18(18) ?
C9 N2 C6 C5 . . . . -179.39(14) ?
C4 C5 C6 N2 . . . . -3.2(3) ?
C4 C5 C6 C7 . . . . 177.73(17) ?
N2 C6 C7 C8 . . . . 0.59(17) ?
C5 C6 C7 C8 . . . . 179.74(15) ?
N2 C6 C7 C16 . . . . -179.69(14) ?
C5 C6 C7 C16 . . . . -0.5(3) ?
C6 C7 C8 C9 . . . . -0.79(18) ?
C16 C7 C8 C9 . . . . 179.52(16) ?
C6 C7 C8 C13 . . . . -178.96(15) ?
C16 C7 C8 C13 . . . . 1.4(3) ?
C6 N2 C9 C8 . . . . -0.33(17) ?
C7 C8 C9 N2 . . . . 0.69(17) ?
C13 C8 C9 N2 . . . . 178.99(14) ?
C14 O2 C13 O1 . . . . 3.3(2) ?
C14 O2 C13 C8 . . . . -176.45(13) ?
C9 C8 C13 O1 . . . . 12.1(3) ?
C7 C8 C13 O1 . . . . -170.02(16) ?
C9 C8 C13 O2 . . . . -168.19(14) ?
C7 C8 C13 O2 . . . . 9.7(2) ?
C13 O2 C14 C15 . . . . 167.03(17) ?
C6 C7 C16 C17 . . . . 64.1(2) ?
C8 C7 C16 C17 . . . . -116.2(2) ?
C6 C7 C16 C21 . . . . -112.40(18) ?
C8 C7 C16 C21 . . . . 67.2(2) ?
C21 C16 C17 C18 . . . . 1.0(3) ?
C7 C16 C17 C18 . . . . -175.61(16) ?
C16 C17 C18 C19 . . . . 0.8(3) ?
C17 C18 C19 C20 . . . . -1.1(3) ?
C18 C19 C20 C25 . . . . 179.31(18) ?
C18 C19 C20 C21 . . . . -0.4(3) ?
C17 C16 C21 C22 . . . . 177.87(15) ?
C7 C16 C21 C22 . . . . -5.5(2) ?
C17 C16 C21 C20 . . . . -2.4(2) ?
C7 C16 C21 C20 . . . . 174.16(14) ?
C19 C20 C21 C22 . . . . -178.15(16) ?
C25 C20 C21 C22 . . . . 2.2(2) ?
C19 C20 C21 C16 . . . . 2.1(2) ?
C25 C20 C21 C16 . . . . -177.55(15) ?
C16 C21 C22 C23 . . . . 179.89(16) ?
C20 C21 C22 C23 . . . . 0.2(2) ?
C21 C22 C23 C24 . . . . -2.5(3) ?
C22 C23 C24 C25 . . . . 2.2(3) ?
C23 C24 C25 C20 . . . . 0.3(3) ?
C19 C20 C25 C24 . . . . 177.85(19) ?
C21 C20 C25 C24 . . . . -2.5(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1 2_645 0.891(18) 2.302(18) 2.9038(17) 124.8(15) ?
N2 H2 N1 . 0.891(18) 2.228(18) 2.8234(19) 123.9(14) ?

####################################################################### 
# 
# 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_rds642
_database_code_depnum_ccdc_archive 'CCDC 1900117'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'ZW50 Pd-DHDP'
_chemical_formula_moiety         'C30 H36 Br2 N4 O4 Pd'
_chemical_formula_sum            'C30 H36 Br2 N4 O4 Pd'
_chemical_formula_iupac          ?
_chemical_formula_weight         782.85

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   13.0158(3)
_cell_length_b                   8.1799(2)
_cell_length_c                   14.3232(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.1060(9)
_cell_angle_gamma                90
_cell_volume                     1521.05(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    505
_cell_measurement_theta_min      2.8646
_cell_measurement_theta_max      34.3261
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.142
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784

_exptl_absorpt_coefficient_mu    3.279
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  0.65

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            71519
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         40.43
_diffrn_reflns_theta_full        40.43
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
reflection 1 0 0 omitted; blocked by beamstop
;

_reflns_number_total             9654
_reflns_number_gt                8790
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0174
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0431
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         9654
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0191P)²+0.5858P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.824
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 786)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd1 0 0.5 0.5 0.00604(10) Uani d . P S 1 . .
Br Br1 0.26672(2) 0.13051(2) 0.25922(2) 0.01406(2) Uani d . . . 1 . .
N N2 0.12680(4) 0.40830(7) 0.44802(4) 0.00830(8) Uani d . . . 1 . .
N N1 -0.07649(4) 0.30782(7) 0.44194(4) 0.00764(8) Uani d . . . 1 . .
C C7 0.22671(5) 0.26497(9) 0.35630(5) 0.00982(10) Uani d . . . 1 . .
C C1 -0.14525(5) 0.21302(8) 0.47464(5) 0.00802(9) Uani d . . . 1 . .
C C8 0.28986(5) 0.32190(9) 0.43421(5) 0.01030(10) Uani d . . . 1 . .
C C9 0.22404(5) 0.41028(9) 0.48806(5) 0.00965(9) Uani d . . . 1 . .
H H9 0.2447 0.4644 0.545 0.012 Uiso calc U . R 1 . .
C C12 -0.30279(6) 0.05975(10) 0.40567(6) 0.01468(12) Uani d . . . 1 . .
H H12A -0.3173 0.0153 0.4669 0.022 Uiso calc U . R 1 . .
H H12B -0.3256 -0.0182 0.3565 0.022 Uiso calc U . R 1 . .
H H12C -0.3396 0.1634 0.3953 0.022 Uiso calc U . R 1 . .
C C13 0.39781(5) 0.28319(10) 0.45948(5) 0.01331(11) Uani d . . . 1 . .
C C4 -0.06037(5) 0.25953(8) 0.34766(4) 0.00829(9) Uani d . . . 1 . .
C C6 0.12648(5) 0.31683(8) 0.36686(5) 0.00857(9) Uani d . . . 1 . .
C C5 0.03339(5) 0.26481(8) 0.31397(5) 0.00939(9) Uani d . . . 1 . .
H H5 0.0389 0.232 0.2509 0.011 Uiso calc U . R 1 . .
C C3 -0.15517(5) 0.16906(9) 0.31172(5) 0.00979(10) Uani d . . . 1 . .
H H3A -0.1395 0.086 0.2645 0.012 Uiso calc U . R 1 . .
H H3B -0.2089 0.2443 0.2846 0.012 Uiso calc U . R 1 . .
O O2 0.42700(4) 0.33665(8) 0.54640(4) 0.01607(10) Uani d . . . 1 . .
O O1 0.45449(5) 0.20898(11) 0.41100(5) 0.02449(14) Uani d . . . 1 . .
C C14 0.53097(6) 0.29330(13) 0.57983(6) 0.02065(16) Uani d . . . 1 . .
H H14A 0.5811 0.3424 0.5392 0.025 Uiso calc U . R 1 . .
H H14B 0.5397 0.1731 0.5793 0.025 Uiso calc U . R 1 . .
C C15 0.54856(7) 0.35772(17) 0.67812(7) 0.0287(2) Uani d . . . 1 . .
H H15A 0.5367 0.476 0.6782 0.043 Uiso calc U . R 1 . .
H H15B 0.6196 0.3348 0.7018 0.043 Uiso calc U . R 1 . .
H H15C 0.5009 0.3042 0.7184 0.043 Uiso calc U . R 1 . .
C C10 -0.17251(6) 0.21273(9) 0.57329(5) 0.01233(11) Uani d . . . 1 . .
H H10A -0.1244 0.2829 0.6107 0.018 Uiso calc U . R 1 . .
H H10B -0.1683 0.1009 0.5979 0.018 Uiso calc U . R 1 . .
H H10C -0.2428 0.2542 0.5766 0.018 Uiso calc U . R 1 . .
C C2 -0.18740(5) 0.08894(8) 0.40306(5) 0.00889(9) Uani d . . . 1 . .
C C11 -0.12604(6) -0.06972(9) 0.42248(6) 0.01305(11) Uani d . . . 1 . .
H H11A -0.0528 -0.0492 0.4155 0.02 Uiso calc U . R 1 . .
H H11B -0.1509 -0.1541 0.3779 0.02 Uiso calc U . R 1 . .
H H11C -0.1353 -0.1069 0.4864 0.02 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 N2 . 2.0041(6) ?
Pd1 N2 3_566 2.0042(6) ?
Pd1 N1 . 2.0088(6) ?
Pd1 N1 3_566 2.0089(6) ?
Br1 C7 . 1.8757(7) ?
N2 C9 . 1.3517(9) ?
N2 C6 . 1.3822(9) ?
N1 C1 . 1.2969(8) ?
N1 C4 . 1.4366(9) ?
C7 C6 . 1.3904(9) ?
C7 C8 . 1.4164(10) ?
C1 C10 . 1.4813(10) ?
C1 C2 . 1.5171(9) ?
C8 C9 . 1.3950(10) ?
C8 C13 . 1.4603(10) ?
C9 H9 . 0.95 ?
C12 C2 . 1.5239(10) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 O1 . 1.2117(10) ?
C13 O2 . 1.3482(10) ?
C4 C5 . 1.3447(9) ?
C4 C3 . 1.4980(9) ?
C6 C5 . 1.4462(9) ?
C5 H5 . 0.95 ?
C3 C2 . 1.5477(10) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
O2 C14 . 1.4469(10) ?
C14 C15 . 1.5052(14) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C2 C11 . 1.5386(10) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Pd1 N2 . 3_566 179.999(16) ?
N2 Pd1 N1 . . 87.14(2) ?
N2 Pd1 N1 3_566 . 92.85(2) ?
N2 Pd1 N1 . 3_566 92.86(2) ?
N2 Pd1 N1 3_566 3_566 87.14(2) ?
N1 Pd1 N1 . 3_566 180.0 ?
C9 N2 C6 . . 108.04(6) ?
C9 N2 Pd1 . . 127.51(5) ?
C6 N2 Pd1 . . 124.20(4) ?
C1 N1 C4 . . 109.03(5) ?
C1 N1 Pd1 . . 130.75(5) ?
C4 N1 Pd1 . . 120.19(4) ?
C6 C7 C8 . . 108.06(6) ?
C6 C7 Br1 . . 124.89(5) ?
C8 C7 Br1 . . 126.92(5) ?
N1 C1 C10 . . 124.34(6) ?
N1 C1 C2 . . 112.42(6) ?
C10 C1 C2 . . 122.94(6) ?
C9 C8 C7 . . 105.14(6) ?
C9 C8 C13 . . 126.40(7) ?
C7 C8 C13 . . 128.15(6) ?
N2 C9 C8 . . 110.65(6) ?
N2 C9 H9 . . 124.7 ?
C8 C9 H9 . . 124.7 ?
C2 C12 H12A . . 109.5 ?
C2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O1 C13 O2 . . 123.29(7) ?
O1 C13 C8 . . 125.52(7) ?
O2 C13 C8 . . 111.16(6) ?
C5 C4 N1 . . 121.72(6) ?
C5 C4 C3 . . 129.71(6) ?
N1 C4 C3 . . 106.66(5) ?
N2 C6 C7 . . 108.08(6) ?
N2 C6 C5 . . 123.49(6) ?
C7 C6 C5 . . 127.64(6) ?
C4 C5 C6 . . 124.70(6) ?
C4 C5 H5 . . 117.6 ?
C6 C5 H5 . . 117.6 ?
C4 C3 C2 . . 100.67(5) ?
C4 C3 H3A . . 111.6 ?
C2 C3 H3A . . 111.6 ?
C4 C3 H3B . . 111.6 ?
C2 C3 H3B . . 111.6 ?
H3A C3 H3B . . 109.4 ?
C13 O2 C14 . . 114.91(6) ?
O2 C14 C15 . . 107.45(7) ?
O2 C14 H14A . . 110.2 ?
C15 C14 H14A . . 110.2 ?
O2 C14 H14B . . 110.2 ?
C15 C14 H14B . . 110.2 ?
H14A C14 H14B . . 108.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C1 C2 C12 . . 113.42(6) ?
C1 C2 C11 . . 106.52(5) ?
C12 C2 C11 . . 111.29(6) ?
C1 C2 C3 . . 100.44(5) ?
C12 C2 C3 . . 114.48(6) ?
C11 C2 C3 . . 109.96(6) ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C10 . . . . 172.15(6) ?
Pd1 N1 C1 C10 . . . . -9.76(10) ?
C4 N1 C1 C2 . . . . -1.80(7) ?
Pd1 N1 C1 C2 . . . . 176.28(4) ?
C6 C7 C8 C9 . . . . -1.35(8) ?
Br1 C7 C8 C9 . . . . -177.31(5) ?
C6 C7 C8 C13 . . . . 172.53(7) ?
Br1 C7 C8 C13 . . . . -3.43(11) ?
C6 N2 C9 C8 . . . . 0.49(8) ?
Pd1 N2 C9 C8 . . . . 174.81(5) ?
C7 C8 C9 N2 . . . . 0.54(8) ?
C13 C8 C9 N2 . . . . -173.48(7) ?
C9 C8 C13 O1 . . . . -178.44(9) ?
C7 C8 C13 O1 . . . . 8.91(14) ?
C9 C8 C13 O2 . . . . 3.47(11) ?
C7 C8 C13 O2 . . . . -169.19(7) ?
C1 N1 C4 C5 . . . . -143.32(7) ?
Pd1 N1 C4 C5 . . . . 38.36(8) ?
C1 N1 C4 C3 . . . . 22.36(7) ?
Pd1 N1 C4 C3 . . . . -155.96(4) ?
C9 N2 C6 C7 . . . . -1.34(8) ?
Pd1 N2 C6 C7 . . . . -175.90(5) ?
C9 N2 C6 C5 . . . . 169.14(6) ?
Pd1 N2 C6 C5 . . . . -5.42(9) ?
C8 C7 C6 N2 . . . . 1.68(8) ?
Br1 C7 C6 N2 . . . . 177.74(5) ?
C8 C7 C6 C5 . . . . -168.29(7) ?
Br1 C7 C6 C5 . . . . 7.77(11) ?
N1 C4 C5 C6 . . . . 0.45(11) ?
C3 C4 C5 C6 . . . . -161.61(7) ?
N2 C6 C5 C4 . . . . -18.47(11) ?
C7 C6 C5 C4 . . . . 150.08(7) ?
C5 C4 C3 C2 . . . . 132.06(7) ?
N1 C4 C3 C2 . . . . -32.07(7) ?
O1 C13 O2 C14 . . . . -2.31(13) ?
C8 C13 O2 C14 . . . . 175.83(7) ?
C13 O2 C14 C15 . . . . -178.16(8) ?
N1 C1 C2 C12 . . . . -140.86(6) ?
C10 C1 C2 C12 . . . . 45.09(9) ?
N1 C1 C2 C11 . . . . 96.38(7) ?
C10 C1 C2 C11 . . . . -77.67(8) ?
N1 C1 C2 C3 . . . . -18.25(7) ?
C10 C1 C2 C3 . . . . 167.70(6) ?
C4 C3 C2 C1 . . . . 29.00(6) ?
C4 C3 C2 C12 . . . . 150.86(6) ?
C4 C3 C2 C11 . . . . -82.99(6) ?

