# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_181019RAL_RAHMAN_MR_01_009_100K_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2239373'
loop_
_audit_author_name
_audit_author_address
'Roger Lalancette'
;Rutgers University
United States of America
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H36 Au Cl N2'
_chemical_formula_sum            'C19 H36 Au Cl N2'
_chemical_formula_weight         524.91

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'
Au Au -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.5347(16)
_cell_length_b                   13.5209(17)
_cell_length_c                   13.0674(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.446(3)
_cell_angle_gamma                90
_cell_volume                     2210.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9783
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      66.54

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.231
_exptl_absorpt_coefficient_mu    13.610
_shelx_estimated_absorpt_T_min   0.099
_shelx_estimated_absorpt_T_max   0.145
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.064
_exptl_absorpt_correction_T_max  0.267
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_special_details           
; 
 'crystal mounted on a Cryoloop using Paratone-N' 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24461
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.711
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_full        66.583
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3890
_reflns_number_gt                3864
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_cell_refinement       'APEX 2'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0124P)²+4.6159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.000201(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3890
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0485
_refine_ls_wR_factor_gt          0.0484
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.15901(2) 0.36432(2) 0.36831(2) 0.01867(6) Uani 1 1 d . . . . .
Cl1 Cl 0.04039(7) 0.40228(6) 0.23481(6) 0.02785(18) Uani 1 1 d . . . . .
N2 N 0.3430(2) 0.26302(19) 0.4851(2) 0.0186(5) Uani 1 1 d . . . . .
N1 N 0.2672(2) 0.36967(19) 0.5818(2) 0.0191(6) Uani 1 1 d . . . . .
C1 C 0.2633(3) 0.3307(2) 0.4857(2) 0.0186(6) Uani 1 1 d . . . . .
C7 C 0.1745(3) 0.5342(2) 0.5566(2) 0.0198(6) Uani 1 1 d . . . . .
H7A H 0.111965 0.570021 0.580889 0.024 Uiso 1 1 calc R U . . .
H7B H 0.154102 0.511746 0.485991 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3954(3) 0.2638(2) 0.3069(3) 0.0242(7) Uani 1 1 d . . . . .
H14A H 0.332190 0.301895 0.282925 0.036 Uiso 1 1 calc R U . . .
H14B H 0.418736 0.222429 0.250896 0.036 Uiso 1 1 calc R U . . .
H14C H 0.453018 0.309279 0.329327 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2281(3) 0.6772(3) 0.4550(3) 0.0375(9) Uani 1 1 d . . . . .
H11A H 0.281442 0.728870 0.445769 0.056 Uiso 1 1 calc R U . . .
H11B H 0.159140 0.707803 0.467172 0.056 Uiso 1 1 calc R U . . .
H11C H 0.220724 0.636178 0.393077 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2713(3) 0.1328(2) 0.3602(3) 0.0212(7) Uani 1 1 d . . . . .
H15A H 0.296209 0.091016 0.304235 0.025 Uiso 1 1 calc R U . . .
H15B H 0.217085 0.178341 0.328352 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3674(3) 0.1978(2) 0.3971(3) 0.0208(7) Uani 1 1 d . . . . .
C5 C 0.0801(3) 0.3863(3) 0.6206(3) 0.0252(7) Uani 1 1 d . . . . .
H5A H 0.056349 0.371056 0.549555 0.038 Uiso 1 1 calc R U . . .
H5B H 0.026943 0.428567 0.651127 0.038 Uiso 1 1 calc R U . . .
H5C H 0.088159 0.324769 0.659910 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4668(3) 0.1357(3) 0.4276(3) 0.0285(8) Uani 1 1 d . . . . .
H13A H 0.528383 0.179532 0.440851 0.043 Uiso 1 1 calc R U . . .
H13B H 0.481259 0.090169 0.371704 0.043 Uiso 1 1 calc R U . . .
H13C H 0.454388 0.097729 0.489634 0.043 Uiso 1 1 calc R U . . .
C2 C 0.3500(3) 0.3259(3) 0.6399(3) 0.0244(7) Uani 1 1 d . . . . .
H2 H 0.369996 0.339739 0.709738 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1876(3) 0.4405(2) 0.6226(2) 0.0200(6) Uani 1 1 d . . . . .
C3 C 0.3969(3) 0.2604(2) 0.5803(3) 0.0232(7) Uani 1 1 d . . . . .
H3 H 0.456430 0.219693 0.599855 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2640(3) 0.6123(2) 0.5472(3) 0.0239(7) Uani 1 1 d . . . . .
C6 C 0.2215(3) 0.4641(3) 0.7347(3) 0.0277(8) Uani 1 1 d . . . . .
H6A H 0.217147 0.404049 0.776167 0.042 Uiso 1 1 calc R U . . .
H6B H 0.173845 0.514678 0.760396 0.042 Uiso 1 1 calc R U . . .
H6C H 0.295130 0.488851 0.739144 0.042 Uiso 1 1 calc R U . . .
C17 C 0.1545(3) 0.1171(3) 0.5160(3) 0.0394(10) Uani 1 1 d . . . . .
H17A H 0.112914 0.069753 0.554126 0.059 Uiso 1 1 calc R U . . .
H17B H 0.106700 0.167583 0.485091 0.059 Uiso 1 1 calc R U . . .
H17C H 0.208181 0.148666 0.562871 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2104(3) 0.0626(3) 0.4316(3) 0.0276(8) Uani 1 1 d . . . . .
C18 C 0.2816(4) -0.0187(3) 0.4817(3) 0.0404(10) Uani 1 1 d . . . . .
H18A H 0.331106 0.010769 0.533987 0.061 Uiso 1 1 calc R U . . .
H18B H 0.322289 -0.050854 0.429260 0.061 Uiso 1 1 calc R U . . .
H18C H 0.236730 -0.067810 0.513653 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2755(3) 0.6804(3) 0.6416(3) 0.0368(9) Uani 1 1 d . . . . .
H10A H 0.309707 0.643901 0.699504 0.055 Uiso 1 1 calc R U . . .
H10B H 0.204685 0.702916 0.659426 0.055 Uiso 1 1 calc R U . . .
H10C H 0.319560 0.737734 0.626025 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3722(3) 0.5665(3) 0.5271(3) 0.0309(8) Uani 1 1 d . . . . .
H9A H 0.363954 0.521482 0.468370 0.046 Uiso 1 1 calc R U . . .
H9B H 0.399234 0.529741 0.587810 0.046 Uiso 1 1 calc R U . . .
H9C H 0.422862 0.619056 0.512064 0.046 Uiso 1 1 calc R U . . .
C19 C 0.1243(4) 0.0128(3) 0.3604(4) 0.0484(11) Uani 1 1 d . . . . .
H19A H 0.084461 -0.034995 0.399609 0.073 Uiso 1 1 calc R U . . .
H19B H 0.158351 -0.021475 0.304889 0.073 Uiso 1 1 calc R U . . .
H19C H 0.075079 0.063170 0.331239 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 2.006(3) . ?
Au1 Cl1 2.2816(8) . ?
N2 C1 1.355(4) . ?
N2 C3 1.380(4) . ?
N2 C12 1.495(4) . ?
N1 C1 1.360(4) . ?
N1 C2 1.381(4) . ?
N1 C4 1.503(4) . ?
C7 C4 1.537(4) . ?
C7 C8 1.551(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C14 C12 1.537(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C11 C8 1.536(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C15 C12 1.544(4) . ?
C15 C16 1.562(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C12 C13 1.535(4) . ?
C5 C4 1.533(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C2 C3 1.339(5) . ?
C2 H2 0.9500 . ?
C4 C6 1.534(4) . ?
C3 H3 0.9500 . ?
C8 C9 1.528(5) . ?
C8 C10 1.539(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C17 C16 1.530(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 C18 1.537(5) . ?
C16 C19 1.538(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 Cl1 179.89(10) . . ?
C1 N2 C3 109.5(3) . . ?
C1 N2 C12 126.0(3) . . ?
C3 N2 C12 124.5(3) . . ?
C1 N1 C2 109.0(3) . . ?
C1 N1 C4 125.9(3) . . ?
C2 N1 C4 124.8(3) . . ?
N2 C1 N1 106.3(3) . . ?
N2 C1 Au1 126.5(2) . . ?
N1 C1 Au1 127.2(2) . . ?
C4 C7 C8 123.6(3) . . ?
C4 C7 H7A 106.4 . . ?
C8 C7 H7A 106.4 . . ?
C4 C7 H7B 106.4 . . ?
C8 C7 H7B 106.4 . . ?
H7A C7 H7B 106.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C15 C16 124.0(3) . . ?
C12 C15 H15A 106.3 . . ?
C16 C15 H15A 106.3 . . ?
C12 C15 H15B 106.3 . . ?
C16 C15 H15B 106.3 . . ?
H15A C15 H15B 106.4 . . ?
N2 C12 C13 108.9(3) . . ?
N2 C12 C14 108.3(3) . . ?
C13 C12 C14 107.3(3) . . ?
N2 C12 C15 112.6(3) . . ?
C13 C12 C15 112.1(3) . . ?
C14 C12 C15 107.5(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C2 N1 107.7(3) . . ?
C3 C2 H2 126.1 . . ?
N1 C2 H2 126.1 . . ?
N1 C4 C5 107.0(3) . . ?
N1 C4 C6 108.7(3) . . ?
C5 C4 C6 108.0(3) . . ?
N1 C4 C7 112.1(3) . . ?
C5 C4 C7 108.7(3) . . ?
C6 C4 C7 112.2(3) . . ?
C2 C3 N2 107.4(3) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
C9 C8 C11 108.5(3) . . ?
C9 C8 C10 109.8(3) . . ?
C11 C8 C10 107.3(3) . . ?
C9 C8 C7 113.0(3) . . ?
C11 C8 C7 105.8(3) . . ?
C10 C8 C7 112.2(3) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C17 C16 C18 108.4(3) . . ?
C17 C16 C19 108.1(3) . . ?
C18 C16 C19 108.2(3) . . ?
C17 C16 C15 113.5(3) . . ?
C18 C16 C15 113.4(3) . . ?
C19 C16 C15 104.8(3) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.593
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.079



####################################################################### 
# 
# 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_BD315_a
_database_code_depnum_ccdc_archive 'CCDC 2239374'
loop_
_audit_author_name
_audit_author_address
'Blazej Dziuk'
;Wroclaw University of Science and Technology
Poland
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT242_BD315_a             
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C6 Check 
RESPONSE: Large differences for average U(eq) occur for terminal 
groups such as the t-butyl moiety.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H36 Cl Cu N2'
_chemical_formula_weight         391.49

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6916(6)
_cell_length_b                   13.5030(7)
_cell_length_c                   13.0909(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.351(4)
_cell_angle_gamma                90
_cell_volume                     2233.67(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14984
_cell_measurement_theta_min      2.616
_cell_measurement_theta_max      25.994

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.57 (release 26-01-2010 CrysAlis171 .NET)
(compiled Jan 26 2010,14:36:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_reflns_number            14984
_diffrn_reflns_av_unetI/netI     0.1108
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.616
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4387
_reflns_number_gt                1951
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4387
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_restrained_S_all      0.824
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.15783(4) 0.35706(3) 0.37921(3) 0.0609(2) Uani 1 1 d . . . . .
C1 C 0.2563(3) 0.3217(3) 0.4900(3) 0.0495(9) Uani 1 1 d . . . . .
Cl1 Cl 0.04929(9) 0.39677(9) 0.25676(8) 0.0897(4) Uani 1 1 d . . . . .
N1 N 0.3334(2) 0.2527(2) 0.4900(2) 0.0542(8) Uani 1 1 d . . . . .
N2 N 0.2632(2) 0.3575(2) 0.5871(2) 0.0531(8) Uani 1 1 d . . . . .
C2 C 0.3885(3) 0.2480(3) 0.5851(3) 0.0700(12) Uani 1 1 d . . . . .
H2 H 0.4463 0.2075 0.6042 0.084 Uiso 1 1 calc R U . . .
C4 C 0.3560(3) 0.1925(3) 0.3992(3) 0.0614(11) Uani 1 1 d . . . . .
C3 C 0.3443(3) 0.3117(3) 0.6445(3) 0.0689(12) Uani 1 1 d . . . . .
H3 H 0.3648 0.3234 0.7135 0.083 Uiso 1 1 calc R U . . .
C5 C 0.2570(3) 0.1327(3) 0.3576(3) 0.0664(11) Uani 1 1 d . . . . .
H5A H 0.2051 0.1814 0.3316 0.080 Uiso 1 1 calc R U . . .
H5B H 0.2774 0.0970 0.2982 0.080 Uiso 1 1 calc R U . . .
C8 C 0.3830(3) 0.2635(3) 0.3143(3) 0.0830(13) Uani 1 1 d . . . . .
H8A H 0.4047 0.2262 0.2575 0.125 Uiso 1 1 calc R U . . .
H8B H 0.4395 0.3066 0.3402 0.125 Uiso 1 1 calc R U . . .
H8C H 0.3218 0.3023 0.2920 0.125 Uiso 1 1 calc R U . . .
C7 C 0.4521(3) 0.1261(3) 0.4280(4) 0.1010(16) Uani 1 1 d . . . . .
H7A H 0.4650 0.0853 0.3704 0.151 Uiso 1 1 calc R U . . .
H7B H 0.4385 0.0849 0.4850 0.151 Uiso 1 1 calc R U . . .
H7C H 0.5131 0.1666 0.4465 0.151 Uiso 1 1 calc R U . . .
C6 C 0.1970(4) 0.0582(3) 0.4185(4) 0.0832(14) Uani 1 1 d . . . . .
C9 C 0.1487(4) 0.1034(4) 0.5093(4) 0.1165(19) Uani 1 1 d . . . . .
H9A H 0.1005 0.1551 0.4858 0.175 Uiso 1 1 calc R U . . .
H9B H 0.2038 0.1305 0.5564 0.175 Uiso 1 1 calc R U . . .
H9C H 0.1113 0.0533 0.5433 0.175 Uiso 1 1 calc R U . . .
C10 C 0.1078(5) 0.0198(5) 0.3436(4) 0.179(3) Uani 1 1 d . . . . .
H10A H 0.0599 0.0729 0.3240 0.268 Uiso 1 1 calc R U . . .
H10B H 0.0706 -0.0319 0.3756 0.268 Uiso 1 1 calc R U . . .
H10C H 0.1366 -0.0060 0.2837 0.268 Uiso 1 1 calc R U . . .
C11 C 0.2668(5) -0.0291(4) 0.4592(5) 0.179(3) Uani 1 1 d . . . . .
H11A H 0.2967 -0.0610 0.4031 0.268 Uiso 1 1 calc R U . . .
H11B H 0.2245 -0.0758 0.4927 0.268 Uiso 1 1 calc R U . . .
H11C H 0.3226 -0.0050 0.5074 0.268 Uiso 1 1 calc R U . . .
C12 C 0.1873(3) 0.4295(3) 0.6250(3) 0.0588(11) Uani 1 1 d . . . . .
C13 C 0.1785(3) 0.5236(3) 0.5596(3) 0.0571(10) Uani 1 1 d . . . . .
H13A H 0.1202 0.5613 0.5828 0.068 Uiso 1 1 calc R U . . .
H13B H 0.1559 0.5024 0.4902 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2689(3) 0.5979(3) 0.5505(3) 0.0716(12) Uani 1 1 d . . . . .
C15 C 0.2198(3) 0.4524(3) 0.7391(3) 0.0920(15) Uani 1 1 d . . . . .
H15A H 0.2920 0.4744 0.7470 0.138 Uiso 1 1 calc R U . . .
H15B H 0.2128 0.3936 0.7792 0.138 Uiso 1 1 calc R U . . .
H15C H 0.1748 0.5033 0.7621 0.138 Uiso 1 1 calc R U . . .
C16 C 0.0789(3) 0.3796(3) 0.6180(3) 0.0797(13) Uani 1 1 d . . . . .
H16A H 0.0554 0.3672 0.5473 0.120 Uiso 1 1 calc R U . . .
H16B H 0.0293 0.4222 0.6474 0.120 Uiso 1 1 calc R U . . .
H16C H 0.0841 0.3181 0.6549 0.120 Uiso 1 1 calc R U . . .
C17 C 0.3702(3) 0.5505(3) 0.5240(4) 0.1159(19) Uani 1 1 d . . . . .
H17A H 0.3568 0.5125 0.4622 0.174 Uiso 1 1 calc R U . . .
H17B H 0.3969 0.5077 0.5790 0.174 Uiso 1 1 calc R U . . .
H17C H 0.4215 0.6010 0.5140 0.174 Uiso 1 1 calc R U . . .
C18 C 0.2912(4) 0.6610(4) 0.6469(4) 0.149(3) Uani 1 1 d . . . . .
H18A H 0.3308 0.7186 0.6309 0.224 Uiso 1 1 calc R U . . .
H18B H 0.3313 0.6230 0.6989 0.224 Uiso 1 1 calc R U . . .
H18C H 0.2255 0.6810 0.6714 0.224 Uiso 1 1 calc R U . . .
C19 C 0.2321(4) 0.6680(4) 0.4633(5) 0.137(2) Uani 1 1 d . . . . .
H19A H 0.2851 0.7177 0.4566 0.206 Uiso 1 1 calc R U . . .
H19B H 0.1672 0.6993 0.4779 0.206 Uiso 1 1 calc R U . . .
H19C H 0.2206 0.6314 0.4004 0.206 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 C1 1.885(3) . ?
Cu1 Cl1 2.0839(10) . ?
C1 N1 1.351(4) . ?
C1 N2 1.356(4) . ?
N1 C2 1.371(4) . ?
N1 C4 1.490(4) . ?
N2 C3 1.365(4) . ?
N2 C12 1.485(4) . ?
C2 C3 1.319(5) . ?
C2 H2 0.9300 . ?
C4 C8 1.530(5) . ?
C4 C7 1.532(5) . ?
C4 C5 1.549(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.530(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 C9 1.516(5) . ?
C6 C10 1.518(6) . ?
C6 C11 1.539(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C16 1.526(5) . ?
C12 C13 1.532(5) . ?
C12 C15 1.544(4) . ?
C13 C14 1.537(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C17 1.505(5) . ?
C14 C19 1.523(6) . ?
C14 C18 1.526(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Cu1 Cl1 179.76(12) . . ?
N1 C1 N2 105.2(3) . . ?
N1 C1 Cu1 127.1(3) . . ?
N2 C1 Cu1 127.7(3) . . ?
C1 N1 C2 109.9(3) . . ?
C1 N1 C4 124.7(3) . . ?
C2 N1 C4 125.4(3) . . ?
C1 N2 C3 109.5(3) . . ?
C1 N2 C12 124.0(3) . . ?
C3 N2 C12 126.3(3) . . ?
C3 C2 N1 107.2(3) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
N1 C4 C8 108.1(3) . . ?
N1 C4 C7 109.3(3) . . ?
C8 C4 C7 108.6(3) . . ?
N1 C4 C5 110.8(3) . . ?
C8 C4 C5 107.4(3) . . ?
C7 C4 C5 112.5(3) . . ?
C2 C3 N2 108.2(3) . . ?
C2 C3 H3 125.9 . . ?
N2 C3 H3 125.9 . . ?
C6 C5 C4 125.9(3) . . ?
C6 C5 H5A 105.8 . . ?
C4 C5 H5A 105.8 . . ?
C6 C5 H5B 105.8 . . ?
C4 C5 H5B 105.8 . . ?
H5A C5 H5B 106.2 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C6 C10 108.2(4) . . ?
C9 C6 C5 113.6(4) . . ?
C10 C6 C5 105.4(4) . . ?
C9 C6 C11 107.3(4) . . ?
C10 C6 C11 109.4(5) . . ?
C5 C6 C11 112.7(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C16 107.5(3) . . ?
N2 C12 C13 111.8(3) . . ?
C16 C12 C13 108.3(3) . . ?
N2 C12 C15 109.3(3) . . ?
C16 C12 C15 107.7(3) . . ?
C13 C12 C15 112.0(3) . . ?
C12 C13 C14 124.7(3) . . ?
C12 C13 H13A 106.2 . . ?
C14 C13 H13A 106.2 . . ?
C12 C13 H13B 106.2 . . ?
C14 C13 H13B 106.2 . . ?
H13A C13 H13B 106.4 . . ?
C17 C14 C19 107.5(4) . . ?
C17 C14 C18 109.4(4) . . ?
C19 C14 C18 107.0(4) . . ?
C17 C14 C13 113.5(4) . . ?
C19 C14 C13 106.5(4) . . ?
C18 C14 C13 112.5(4) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C2 -1.4(4) . . . . ?
Cu1 C1 N1 C2 -179.7(3) . . . . ?
N2 C1 N1 C4 179.7(3) . . . . ?
Cu1 C1 N1 C4 1.4(5) . . . . ?
N1 C1 N2 C3 0.8(4) . . . . ?
Cu1 C1 N2 C3 179.1(3) . . . . ?
N1 C1 N2 C12 -174.6(3) . . . . ?
Cu1 C1 N2 C12 3.7(5) . . . . ?
C1 N1 C2 C3 1.6(5) . . . . ?
C4 N1 C2 C3 -179.6(3) . . . . ?
C1 N1 C4 C8 59.4(4) . . . . ?
C2 N1 C4 C8 -119.3(4) . . . . ?
C1 N1 C4 C7 177.4(4) . . . . ?
C2 N1 C4 C7 -1.3(5) . . . . ?
C1 N1 C4 C5 -58.0(5) . . . . ?
C2 N1 C4 C5 123.2(4) . . . . ?
N1 C2 C3 N2 -1.0(5) . . . . ?
C1 N2 C3 C2 0.1(5) . . . . ?
C12 N2 C3 C2 175.4(4) . . . . ?
N1 C4 C5 C6 -57.5(5) . . . . ?
C8 C4 C5 C6 -175.4(4) . . . . ?
C7 C4 C5 C6 65.2(5) . . . . ?
C4 C5 C6 C9 62.1(6) . . . . ?
C4 C5 C6 C10 -179.6(4) . . . . ?
C4 C5 C6 C11 -60.3(6) . . . . ?
C1 N2 C12 C16 62.9(4) . . . . ?
C3 N2 C12 C16 -111.7(4) . . . . ?
C1 N2 C12 C13 -55.9(4) . . . . ?
C3 N2 C12 C13 129.5(4) . . . . ?
C1 N2 C12 C15 179.5(3) . . . . ?
C3 N2 C12 C15 4.9(5) . . . . ?
N2 C12 C13 C14 -65.0(4) . . . . ?
C16 C12 C13 C14 176.7(3) . . . . ?
C15 C12 C13 C14 58.1(5) . . . . ?
C12 C13 C14 C17 51.3(5) . . . . ?
C12 C13 C14 C19 169.5(4) . . . . ?
C12 C13 C14 C18 -73.6(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
C2 H2 Cl1 0.93 2.68 3.490(4) 145.7 4_666
C16 H16B Cl1 0.96 2.96 3.867(4) 157.5 3_566

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_BD314_a
_database_code_depnum_ccdc_archive 'CCDC 2239375'
loop_
_audit_author_name
_audit_author_address
'Blazej Dziuk'
;Wroclaw University of Science and Technology
Poland
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H36 Ag Cl N2'
_chemical_formula_weight         435.82

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.9804(3)
_cell_length_b                   13.4131(3)
_cell_length_c                   13.1899(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.467(2)
_cell_angle_gamma                90
_cell_volume                     2296.38(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15291
_cell_measurement_theta_min      2.682
_cell_measurement_theta_max      26.000

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.996
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.57 (release 26-01-2010 CrysAlis171 .NET)
(compiled Jan 26 2010,14:36:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_reflns_number            15291
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4501
_reflns_number_gt                3372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4501
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.15824(2) 0.64353(2) 0.36835(2) 0.05428(9) Uani 1 1 d . . . . .
Cl1 Cl 0.04549(7) 0.61216(7) 0.23640(6) 0.0836(2) Uani 1 1 d . . . . .
N1 N 0.25985(16) 0.63203(14) 0.58169(15) 0.0529(5) Uani 1 1 d . . . . .
C1 C 0.25841(18) 0.67409(17) 0.48823(17) 0.0484(6) Uani 1 1 d . . . . .
N2 N 0.33506(14) 0.74256(14) 0.49028(15) 0.0527(5) Uani 1 1 d . . . . .
C2 C 0.3359(2) 0.6751(2) 0.6401(2) 0.0687(8) Uani 1 1 d . . . . .
H2 H 0.3517 0.6597 0.7072 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3827(2) 0.7427(2) 0.5832(2) 0.0670(7) Uani 1 1 d . . . . .
H3 H 0.4378 0.7828 0.6029 0.080 Uiso 1 1 calc R U . . .
C4 C 0.18267(19) 0.55705(19) 0.61909(18) 0.0592(7) Uani 1 1 d . . . . .
C7 C 0.0773(2) 0.6089(2) 0.6166(3) 0.0828(9) Uani 1 1 d . . . . .
H7A H 0.0572 0.6213 0.5475 0.124 Uiso 1 1 calc R U . . .
H7B H 0.0817 0.6711 0.6525 0.124 Uiso 1 1 calc R U . . .
H7C H 0.0270 0.5669 0.6482 0.124 Uiso 1 1 calc R U . . .
C6 C 0.2663(2) 0.3908(2) 0.5361(2) 0.0763(8) Uani 1 1 d . . . . .
C5 C 0.17820(19) 0.46572(19) 0.54992(19) 0.0594(7) Uani 1 1 d . . . . .
H5A H 0.1615 0.4906 0.4827 0.071 Uiso 1 1 calc R U . . .
H5B H 0.1191 0.4272 0.5716 0.071 Uiso 1 1 calc R U . . .
C9 C 0.2761(4) 0.3189(3) 0.6273(3) 0.1277(15) Uani 1 1 d . . . . .
H9A H 0.3195 0.2639 0.6094 0.192 Uiso 1 1 calc R U . . .
H9B H 0.2091 0.2946 0.6451 0.192 Uiso 1 1 calc R U . . .
H9C H 0.3057 0.3537 0.6841 0.192 Uiso 1 1 calc R U . . .
C8 C 0.2082(3) 0.5299(3) 0.72903(19) 0.0915(10) Uani 1 1 d . . . . .
H8A H 0.2776 0.5055 0.7333 0.137 Uiso 1 1 calc R U . . .
H8B H 0.1616 0.4793 0.7519 0.137 Uiso 1 1 calc R U . . .
H8C H 0.2015 0.5880 0.7710 0.137 Uiso 1 1 calc R U . . .
C10 C 0.2374(4) 0.3263(3) 0.4443(3) 0.1332(16) Uani 1 1 d . . . . .
H10A H 0.2363 0.3668 0.3843 0.200 Uiso 1 1 calc R U . . .
H10B H 0.1705 0.2976 0.4544 0.200 Uiso 1 1 calc R U . . .
H10C H 0.2873 0.2740 0.4368 0.200 Uiso 1 1 calc R U . . .
C11 C 0.3692(3) 0.4390(3) 0.5157(3) 0.1210(15) Uani 1 1 d . . . . .
H11A H 0.4193 0.3884 0.5013 0.182 Uiso 1 1 calc R U . . .
H11B H 0.3909 0.4762 0.5743 0.182 Uiso 1 1 calc R U . . .
H11C H 0.3629 0.4831 0.4587 0.182 Uiso 1 1 calc R U . . .
C12 C 0.36315(19) 0.8086(2) 0.4033(2) 0.0596(6) Uani 1 1 d . . . . .
C13 C 0.2712(2) 0.87227(18) 0.3679(2) 0.0651(7) Uani 1 1 d . . . . .
H13A H 0.2961 0.9126 0.3122 0.078 Uiso 1 1 calc R U . . .
H13B H 0.2216 0.8261 0.3387 0.078 Uiso 1 1 calc R U . . .
C14 C 0.2093(3) 0.9429(2) 0.4358(3) 0.0858(9) Uani 1 1 d . . . . .
C15 C 0.3960(2) 0.7415(2) 0.3156(2) 0.0782(8) Uani 1 1 d . . . . .
H15A H 0.3376 0.7047 0.2910 0.117 Uiso 1 1 calc R U . . .
H15B H 0.4481 0.6960 0.3388 0.117 Uiso 1 1 calc R U . . .
H15C H 0.4231 0.7818 0.2618 0.117 Uiso 1 1 calc R U . . .
C16 C 0.4573(3) 0.8719(2) 0.4333(3) 0.0946(11) Uani 1 1 d . . . . .
H16A H 0.5144 0.8288 0.4489 0.142 Uiso 1 1 calc R U . . .
H16B H 0.4412 0.9114 0.4918 0.142 Uiso 1 1 calc R U . . .
H16C H 0.4752 0.9149 0.3781 0.142 Uiso 1 1 calc R U . . .
C17 C 0.2768(4) 1.0255(3) 0.4848(3) 0.152(2) Uani 1 1 d . . . . .
H17A H 0.3149 1.0593 0.4331 0.228 Uiso 1 1 calc R U . . .
H17B H 0.3238 0.9959 0.5327 0.228 Uiso 1 1 calc R U . . .
H17C H 0.2334 1.0724 0.5191 0.228 Uiso 1 1 calc R U . . .
C18 C 0.1528(3) 0.8919(3) 0.5201(3) 0.1183(15) Uani 1 1 d . . . . .
H18A H 0.1071 0.8427 0.4922 0.178 Uiso 1 1 calc R U . . .
H18B H 0.1138 0.9403 0.5573 0.178 Uiso 1 1 calc R U . . .
H18C H 0.2015 0.8603 0.5649 0.178 Uiso 1 1 calc R U . . .
C19 C 0.1330(4) 0.9929(5) 0.3662(3) 0.181(3) Uani 1 1 d . . . . .
H19A H 0.1690 1.0246 0.3117 0.271 Uiso 1 1 calc R U . . .
H19B H 0.0950 1.0420 0.4033 0.271 Uiso 1 1 calc R U . . .
H19C H 0.0864 0.9440 0.3391 0.271 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 C1 2.080(2) . ?
Ag1 Cl1 2.3035(7) . ?
N1 C1 1.356(3) . ?
N1 C2 1.375(3) . ?
N1 C4 1.506(3) . ?
C1 N2 1.354(3) . ?
N2 C3 1.369(3) . ?
N2 C12 1.497(3) . ?
C2 C3 1.327(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.528(3) . ?
C4 C8 1.529(3) . ?
C4 C7 1.535(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 C11 1.510(4) . ?
C6 C10 1.532(5) . ?
C6 C5 1.535(4) . ?
C6 C9 1.546(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.530(4) . ?
C12 C16 1.537(4) . ?
C12 C13 1.537(4) . ?
C13 C14 1.535(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C18 1.502(5) . ?
C14 C19 1.503(5) . ?
C14 C17 1.550(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ag1 Cl1 178.95(7) . . ?
C1 N1 C2 109.8(2) . . ?
C1 N1 C4 124.9(2) . . ?
C2 N1 C4 125.0(2) . . ?
N2 C1 N1 105.0(2) . . ?
N2 C1 Ag1 127.12(17) . . ?
N1 C1 Ag1 127.82(17) . . ?
C1 N2 C3 110.2(2) . . ?
C1 N2 C12 124.7(2) . . ?
C3 N2 C12 125.1(2) . . ?
C3 C2 N1 107.4(2) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 107.5(2) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
N1 C4 C5 111.22(19) . . ?
N1 C4 C8 109.3(2) . . ?
C5 C4 C8 112.5(2) . . ?
N1 C4 C7 106.6(2) . . ?
C5 C4 C7 108.7(2) . . ?
C8 C4 C7 108.3(2) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C6 C10 108.2(3) . . ?
C11 C6 C5 113.7(3) . . ?
C10 C6 C5 106.6(3) . . ?
C11 C6 C9 109.8(3) . . ?
C10 C6 C9 106.3(3) . . ?
C5 C6 C9 111.9(3) . . ?
C4 C5 C6 124.8(2) . . ?
C4 C5 H5A 106.1 . . ?
C6 C5 H5A 106.1 . . ?
C4 C5 H5B 106.1 . . ?
C6 C5 H5B 106.1 . . ?
H5A C5 H5B 106.3 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C15 107.6(2) . . ?
N2 C12 C16 109.1(2) . . ?
C15 C12 C16 107.0(2) . . ?
N2 C12 C13 111.6(2) . . ?
C15 C12 C13 108.5(2) . . ?
C16 C12 C13 112.7(2) . . ?
C14 C13 C12 125.0(3) . . ?
C14 C13 H13A 106.1 . . ?
C12 C13 H13A 106.1 . . ?
C14 C13 H13B 106.1 . . ?
C12 C13 H13B 106.1 . . ?
H13A C13 H13B 106.3 . . ?
C18 C14 C19 109.4(4) . . ?
C18 C14 C13 114.4(3) . . ?
C19 C14 C13 105.3(3) . . ?
C18 C14 C17 107.1(3) . . ?
C19 C14 C17 107.6(4) . . ?
C13 C14 C17 112.8(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 0.5(3) . . . . ?
C4 N1 C1 N2 174.7(2) . . . . ?
C2 N1 C1 Ag1 -177.99(19) . . . . ?
C4 N1 C1 Ag1 -3.8(3) . . . . ?
N1 C1 N2 C3 -0.1(3) . . . . ?
Ag1 C1 N2 C3 178.49(18) . . . . ?
N1 C1 N2 C12 -179.9(2) . . . . ?
Ag1 C1 N2 C12 -1.3(3) . . . . ?
C1 N1 C2 C3 -0.8(3) . . . . ?
C4 N1 C2 C3 -175.0(2) . . . . ?
N1 C2 C3 N2 0.8(3) . . . . ?
C1 N2 C3 C2 -0.5(3) . . . . ?
C12 N2 C3 C2 179.4(2) . . . . ?
C1 N1 C4 C5 57.0(3) . . . . ?
C2 N1 C4 C5 -129.7(3) . . . . ?
C1 N1 C4 C8 -178.2(2) . . . . ?
C2 N1 C4 C8 -4.9(4) . . . . ?
C1 N1 C4 C7 -61.3(3) . . . . ?
C2 N1 C4 C7 112.0(3) . . . . ?
N1 C4 C5 C6 66.4(3) . . . . ?
C8 C4 C5 C6 -56.6(3) . . . . ?
C7 C4 C5 C6 -176.6(2) . . . . ?
C11 C6 C5 C4 -48.7(4) . . . . ?
C10 C6 C5 C4 -167.9(3) . . . . ?
C9 C6 C5 C4 76.3(4) . . . . ?
C1 N2 C12 C15 -61.2(3) . . . . ?
C3 N2 C12 C15 119.0(3) . . . . ?
C1 N2 C12 C16 -177.1(2) . . . . ?
C3 N2 C12 C16 3.2(4) . . . . ?
C1 N2 C12 C13 57.7(3) . . . . ?
C3 N2 C12 C13 -122.1(3) . . . . ?
N2 C12 C13 C14 56.1(3) . . . . ?
C15 C12 C13 C14 174.5(3) . . . . ?
C16 C12 C13 C14 -67.2(4) . . . . ?
C12 C13 C14 C18 -63.6(4) . . . . ?
C12 C13 C14 C19 176.3(3) . . . . ?
C12 C13 C14 C17 59.2(4) . . . . ?

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
C3 H3 Cl1 0.93 2.65 3.502(3) 153.5 4_676
C8 H8B Cl1 0.96 2.96 3.835(3) 152.2 3_566

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_BD311_b
_database_code_depnum_ccdc_archive 'CCDC 2239377'
loop_
_audit_author_name
_audit_author_address
'Blazej Dziuk'
;Wroclaw University of Science and Technology 
Poland
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H40 Cl3 N3 Pd'
_chemical_formula_weight         583.34

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.6940(3)
_cell_length_b                   14.2272(3)
_cell_length_c                   15.3472(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2771.71(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    19014
_cell_measurement_theta_min      2.654
_cell_measurement_theta_max      25.989

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.975
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.57 (release 26-01-2010 CrysAlis171 .NET)
(compiled Jan 26 2010,14:36:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_reflns_number            19014
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5434
_reflns_number_gt                4778
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0205P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5434
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0389
_refine_ls_wR_factor_gt          0.0380
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.29869(2) 0.50171(2) 0.58015(2) 0.03344(6) Uani 1 1 d . . . . .
Cl1 Cl 0.42249(6) 0.61853(5) 0.60422(6) 0.0513(2) Uani 1 1 d . . . . .
N1 N 0.46884(16) 0.36907(15) 0.52310(14) 0.0346(5) Uani 1 1 d . . . . .
C1 C 0.4096(2) 0.40548(17) 0.5890(2) 0.0320(6) Uani 1 1 d . . . . .
N2 N 0.43716(16) 0.35829(14) 0.66198(14) 0.0329(5) Uani 1 1 d . . . . .
Cl2 Cl 0.18037(6) 0.38107(6) 0.55687(7) 0.0562(3) Uani 1 1 d . . . . .
C2 C 0.5334(2) 0.29982(19) 0.55678(19) 0.0441(8) Uani 1 1 d . . . . .
H2 H 0.5826 0.2649 0.5257 0.053 Uiso 1 1 calc R U . . .
C3 C 0.5128(2) 0.29183(19) 0.6409(2) 0.0426(7) Uani 1 1 d . . . . .
H3 H 0.5436 0.2492 0.6791 0.051 Uiso 1 1 calc R U . . .
N3 N 0.17526(19) 0.60270(16) 0.57238(19) 0.0409(6) Uani 1 1 d . . . . .
Cl3 Cl -0.12356(7) 0.61461(9) 0.64046(7) 0.0894(3) Uani 1 1 d . . . . .
C4 C 0.4802(2) 0.39881(19) 0.42984(18) 0.0408(7) Uani 1 1 d . . . . .
C5 C 0.4820(2) 0.3125(2) 0.36877(18) 0.0434(7) Uani 1 1 d . . . . .
H5A H 0.5003 0.3362 0.3115 0.052 Uiso 1 1 calc R U . . .
H5B H 0.5409 0.2742 0.3876 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3890(2) 0.2442(2) 0.35491(19) 0.0472(7) Uani 1 1 d . . . . .
C7 C 0.3977(3) 0.4700(2) 0.40273(19) 0.0579(9) Uani 1 1 d . . . . .
H7A H 0.4055 0.4838 0.3418 0.087 Uiso 1 1 calc R U . . .
H7B H 0.4066 0.5266 0.4360 0.087 Uiso 1 1 calc R U . . .
H7C H 0.3287 0.4446 0.4132 0.087 Uiso 1 1 calc R U . . .
C9 C 0.3544(3) 0.1942(2) 0.4378(2) 0.0642(10) Uani 1 1 d . . . . .
H9A H 0.3016 0.1483 0.4239 0.096 Uiso 1 1 calc R U . . .
H9B H 0.3260 0.2392 0.4780 0.096 Uiso 1 1 calc R U . . .
H9C H 0.4140 0.1635 0.4638 0.096 Uiso 1 1 calc R U . . .
C8 C 0.5883(3) 0.4467(2) 0.4237(2) 0.0688(10) Uani 1 1 d . . . . .
H8A H 0.5974 0.4725 0.3664 0.103 Uiso 1 1 calc R U . . .
H8B H 0.6427 0.4013 0.4347 0.103 Uiso 1 1 calc R U . . .
H8C H 0.5925 0.4962 0.4660 0.103 Uiso 1 1 calc R U . . .
C10 C 0.2922(3) 0.2914(3) 0.3135(3) 0.0761(11) Uani 1 1 d . . . . .
H10A H 0.3140 0.3279 0.2640 0.114 Uiso 1 1 calc R U . . .
H10B H 0.2591 0.3318 0.3554 0.114 Uiso 1 1 calc R U . . .
H10C H 0.2432 0.2441 0.2950 0.114 Uiso 1 1 calc R U . . .
C11 C 0.4294(3) 0.1690(3) 0.2911(2) 0.0758(11) Uani 1 1 d . . . . .
H11A H 0.3762 0.1219 0.2829 0.114 Uiso 1 1 calc R U . . .
H11B H 0.4918 0.1404 0.3144 0.114 Uiso 1 1 calc R U . . .
H11C H 0.4455 0.1979 0.2361 0.114 Uiso 1 1 calc R U . . .
C12 C 0.3973(2) 0.36406(19) 0.75371(17) 0.0403(7) Uani 1 1 d . . . . .
C13 C 0.4905(2) 0.3666(2) 0.81827(18) 0.0411(7) Uani 1 1 d . . . . .
H13A H 0.4602 0.3596 0.8759 0.049 Uiso 1 1 calc R U . . .
H13B H 0.5312 0.3102 0.8074 0.049 Uiso 1 1 calc R U . . .
C14 C 0.5707(3) 0.4478(2) 0.82488(18) 0.0468(8) Uani 1 1 d . . . . .
C15 C 0.3228(3) 0.4468(2) 0.7679(2) 0.0622(10) Uani 1 1 d . . . . .
H15A H 0.3548 0.5032 0.7460 0.093 Uiso 1 1 calc R U . . .
H15B H 0.3090 0.4538 0.8291 0.093 Uiso 1 1 calc R U . . .
H15C H 0.2579 0.4355 0.7377 0.093 Uiso 1 1 calc R U . . .
C16 C 0.3358(3) 0.2725(2) 0.7695(3) 0.0702(11) Uani 1 1 d . . . . .
H16A H 0.2826 0.2656 0.7254 0.105 Uiso 1 1 calc R U . . .
H16B H 0.3031 0.2748 0.8258 0.105 Uiso 1 1 calc R U . . .
H16C H 0.3832 0.2201 0.7669 0.105 Uiso 1 1 calc R U . . .
C17 C 0.6214(3) 0.4751(2) 0.7382(2) 0.0571(9) Uani 1 1 d . . . . .
H17A H 0.6496 0.4200 0.7106 0.086 Uiso 1 1 calc R U . . .
H17B H 0.6772 0.5193 0.7485 0.086 Uiso 1 1 calc R U . . .
H17C H 0.5694 0.5031 0.7010 0.086 Uiso 1 1 calc R U . . .
C18 C 0.6586(3) 0.4106(3) 0.8847(3) 0.0862(13) Uani 1 1 d . . . . .
H18A H 0.6892 0.3553 0.8594 0.129 Uiso 1 1 calc R U . . .
H18B H 0.6296 0.3955 0.9408 0.129 Uiso 1 1 calc R U . . .
H18C H 0.7119 0.4580 0.8914 0.129 Uiso 1 1 calc R U . . .
C19 C 0.5245(4) 0.5362(3) 0.8654(3) 0.0982(15) Uani 1 1 d . . . . .
H19A H 0.5801 0.5798 0.8780 0.147 Uiso 1 1 calc R U . . .
H19B H 0.4885 0.5201 0.9183 0.147 Uiso 1 1 calc R U . . .
H19C H 0.4757 0.5643 0.8254 0.147 Uiso 1 1 calc R U . . .
C20 C 0.0802(2) 0.5832(2) 0.60237(19) 0.0467(8) Uani 1 1 d . . . . .
H20 H 0.0682 0.5243 0.6267 0.056 Uiso 1 1 calc R U . . .
C21 C -0.0017(3) 0.6462(2) 0.5992(2) 0.0548(9) Uani 1 1 d . . . . .
C22 C 0.0141(3) 0.7331(3) 0.5630(2) 0.0654(11) Uani 1 1 d . . . . .
H22 H -0.0402 0.7768 0.5601 0.078 Uiso 1 1 calc R U . . .
C23 C 0.1114(3) 0.7533(2) 0.5315(2) 0.0628(10) Uani 1 1 d . . . . .
H23 H 0.1243 0.8114 0.5058 0.075 Uiso 1 1 calc R U . . .
C24 C 0.1916(3) 0.6876(2) 0.5376(2) 0.0511(8) Uani 1 1 d . . . . .
H24 H 0.2583 0.7029 0.5171 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 C1 1.969(3) . ?
Pd1 N3 2.129(2) . ?
Pd1 Cl2 2.3085(8) . ?
Pd1 Cl1 2.3170(8) . ?
N1 C1 1.362(4) . ?
N1 C2 1.381(3) . ?
N1 C4 1.500(3) . ?
C1 N2 1.352(3) . ?
N2 C3 1.386(3) . ?
N2 C12 1.498(3) . ?
C2 C3 1.322(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
N3 C20 1.321(4) . ?
N3 C24 1.336(4) . ?
Cl3 C21 1.731(4) . ?
C4 C7 1.515(4) . ?
C4 C8 1.535(4) . ?
C4 C5 1.545(4) . ?
C5 C6 1.544(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.522(4) . ?
C6 C10 1.537(4) . ?
C6 C11 1.538(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.526(4) . ?
C12 C16 1.538(4) . ?
C12 C13 1.544(4) . ?
C13 C14 1.544(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.520(4) . ?
C14 C17 1.528(4) . ?
C14 C18 1.539(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(5) . ?
C22 C23 1.357(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Pd1 N3 178.18(11) . . ?
C1 Pd1 Cl2 87.65(7) . . ?
N3 Pd1 Cl2 90.82(7) . . ?
C1 Pd1 Cl1 90.15(7) . . ?
N3 Pd1 Cl1 91.37(7) . . ?
Cl2 Pd1 Cl1 177.80(3) . . ?
C1 N1 C2 108.7(2) . . ?
C1 N1 C4 130.9(2) . . ?
C2 N1 C4 120.1(2) . . ?
N2 C1 N1 106.5(2) . . ?
N2 C1 Pd1 126.0(2) . . ?
N1 C1 Pd1 127.4(2) . . ?
C1 N2 C3 108.9(2) . . ?
C1 N2 C12 131.6(2) . . ?
C3 N2 C12 119.4(2) . . ?
C3 C2 N1 108.0(2) . . ?
C3 C2 H2 126.0 . . ?
N1 C2 H2 126.0 . . ?
C2 C3 N2 107.8(2) . . ?
C2 C3 H3 126.1 . . ?
N2 C3 H3 126.1 . . ?
C20 N3 C24 118.1(3) . . ?
C20 N3 Pd1 120.7(2) . . ?
C24 N3 Pd1 121.2(2) . . ?
N1 C4 C7 112.6(2) . . ?
N1 C4 C8 105.7(2) . . ?
C7 C4 C8 107.7(2) . . ?
N1 C4 C5 110.9(2) . . ?
C7 C4 C5 112.0(2) . . ?
C8 C4 C5 107.6(2) . . ?
C6 C5 C4 125.0(2) . . ?
C6 C5 H5A 106.1 . . ?
C4 C5 H5A 106.1 . . ?
C6 C5 H5B 106.1 . . ?
C4 C5 H5B 106.1 . . ?
H5A C5 H5B 106.3 . . ?
C9 C6 C10 108.7(3) . . ?
C9 C6 C11 107.7(3) . . ?
C10 C6 C11 107.9(3) . . ?
C9 C6 C5 113.5(2) . . ?
C10 C6 C5 113.1(3) . . ?
C11 C6 C5 105.7(3) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C15 112.7(2) . . ?
N2 C12 C16 105.8(2) . . ?
C15 C12 C16 108.5(3) . . ?
N2 C12 C13 110.2(2) . . ?
C15 C12 C13 111.4(2) . . ?
C16 C12 C13 108.0(2) . . ?
C14 C13 C12 124.5(2) . . ?
C14 C13 H13A 106.2 . . ?
C12 C13 H13A 106.2 . . ?
C14 C13 H13B 106.2 . . ?
C12 C13 H13B 106.2 . . ?
H13A C13 H13B 106.4 . . ?
C19 C14 C17 108.0(3) . . ?
C19 C14 C18 108.7(3) . . ?
C17 C14 C18 107.6(3) . . ?
C19 C14 C13 113.0(3) . . ?
C17 C14 C13 114.3(2) . . ?
C18 C14 C13 105.1(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C21 122.8(3) . . ?
N3 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 Cl3 120.9(3) . . ?
C20 C21 Cl3 119.6(3) . . ?
C23 C22 C21 118.0(3) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C22 C23 C24 120.1(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
N3 C24 C23 121.6(3) . . ?
N3 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?

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 N1 C1 N2 -0.5(3) . . . . ?
C4 N1 C1 N2 -173.6(2) . . . . ?
C2 N1 C1 Pd1 -176.76(19) . . . . ?
C4 N1 C1 Pd1 10.2(4) . . . . ?
N1 C1 N2 C3 -0.6(3) . . . . ?
Pd1 C1 N2 C3 175.67(18) . . . . ?
N1 C1 N2 C12 -177.6(2) . . . . ?
Pd1 C1 N2 C12 -1.3(4) . . . . ?
C1 N1 C2 C3 1.6(3) . . . . ?
C4 N1 C2 C3 175.5(2) . . . . ?
N1 C2 C3 N2 -1.9(3) . . . . ?
C1 N2 C3 C2 1.6(3) . . . . ?
C12 N2 C3 C2 179.0(2) . . . . ?
C1 N1 C4 C7 -12.0(4) . . . . ?
C2 N1 C4 C7 175.7(2) . . . . ?
C1 N1 C4 C8 105.4(3) . . . . ?
C2 N1 C4 C8 -67.0(3) . . . . ?
C1 N1 C4 C5 -138.3(3) . . . . ?
C2 N1 C4 C5 49.3(3) . . . . ?
N1 C4 C5 C6 65.0(3) . . . . ?
C7 C4 C5 C6 -61.7(4) . . . . ?
C8 C4 C5 C6 -179.9(3) . . . . ?
C4 C5 C6 C9 -60.6(4) . . . . ?
C4 C5 C6 C10 63.8(4) . . . . ?
C4 C5 C6 C11 -178.4(3) . . . . ?
C1 N2 C12 C15 -9.0(4) . . . . ?
C3 N2 C12 C15 174.3(2) . . . . ?
C1 N2 C12 C16 109.4(3) . . . . ?
C3 N2 C12 C16 -67.3(3) . . . . ?
C1 N2 C12 C13 -134.1(3) . . . . ?
C3 N2 C12 C13 49.2(3) . . . . ?
N2 C12 C13 C14 65.9(3) . . . . ?
C15 C12 C13 C14 -59.9(3) . . . . ?
C16 C12 C13 C14 -178.9(3) . . . . ?
C12 C13 C14 C19 72.0(4) . . . . ?
C12 C13 C14 C17 -52.0(4) . . . . ?
C12 C13 C14 C18 -169.7(3) . . . . ?
C24 N3 C20 C21 0.0(5) . . . . ?
Pd1 N3 C20 C21 179.7(2) . . . . ?
N3 C20 C21 C22 0.5(5) . . . . ?
N3 C20 C21 Cl3 -179.8(2) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
Cl3 C21 C22 C23 -179.8(3) . . . . ?
C21 C22 C23 C24 -0.9(5) . . . . ?
C20 N3 C24 C23 -1.0(5) . . . . ?
Pd1 N3 C24 C23 179.3(2) . . . . ?
C22 C23 C24 N3 1.5(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
C2 H2 Cl2 0.93 2.73 3.626(3) 161.7 4_556
C5 H5B Cl2 0.97 2.96 3.903(3) 165.4 4_556
C7 H7B Cl1 0.96 2.90 3.759(3) 149.3 .
C15 H15A Cl1 0.96 2.86 3.726(3) 150.9 .
C20 H20 Cl2 0.93 2.71 3.221(3) 115.7 .
C22 H22 Cl1 0.93 2.97 3.521(4) 119.7 4_466
C24 H24 Cl1 0.93 2.75 3.256(3) 115.0 .

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_BD309_a
_database_code_depnum_ccdc_archive 'CCDC 2239376'
loop_
_audit_author_name
_audit_author_address
'Blazej Dziuk'
;Wroclaw University of Science and Technology 
Poland
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_BD309_a             
;
PROBLEM: Hirshfeld Test Diff for    C12--C16.       11.0 s.u.  
RESPONSE: Hirshfeld Rigid-Bond Test for few atoms is a consequence of the 
vibration of the terminal groups such as the t-butyl moiety.
;
_vrf_PLAT242_BD309_a             
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C14 Check 
RESPONSE: Large differences for average U(eq) occur for terminal groups such 
as the t-butyl moiety.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H36 N2 Se'
_chemical_formula_weight         371.46

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   32.8739(10)
_cell_length_b                   10.3807(3)
_cell_length_c                   12.1090(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4132.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    26934
_cell_measurement_theta_min      2.658
_cell_measurement_theta_max      25.999

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.818
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.57 (release 26-01-2010 CrysAlis171 .NET)
(compiled Jan 26 2010,14:36:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_reflns_number            26934
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.658
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.705
_diffrn_reflns_point_group_measured_fraction_full 0.705
_reflns_number_total             5729
_reflns_number_gt                3327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.346
_reflns_Friedel_fraction_max     0.382
_reflns_Friedel_fraction_full    0.380

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5729
_refine_ls_number_parameters     417
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_restrained_S_all      0.839
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001

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
Se1 Se 0.41602(2) 0.18826(6) 0.62086(5) 0.0684(2) Uani 1 1 d . . . . .
Se2 Se 0.15696(2) 0.63557(6) 0.64732(5) 0.05983(19) Uani 1 1 d . . . . .
N1 N 0.35965(13) 0.2357(5) 0.4432(4) 0.0465(12) Uani 1 1 d . . . . .
N2 N 0.38834(13) 0.0452(5) 0.4325(3) 0.0421(12) Uani 1 1 d . . . . .
N3 N 0.11567(13) 0.5361(4) 0.4559(4) 0.0447(12) Uani 1 1 d . . . . .
N4 N 0.14054(13) 0.7273(4) 0.4267(4) 0.0438(12) Uani 1 1 d . . . . .
C1 C 0.38677(15) 0.1561(6) 0.4938(4) 0.0394(14) Uani 1 1 d . . . . .
C2 C 0.3451(2) 0.1727(7) 0.3502(5) 0.071(2) Uani 1 1 d . . . . .
H2 H 0.3265 0.2069 0.3002 0.085 Uiso 1 1 calc R U . . .
C3 C 0.36159(18) 0.0564(7) 0.3433(5) 0.0584(17) Uani 1 1 d . . . . .
H3 H 0.3564 -0.0055 0.2897 0.070 Uiso 1 1 calc R U . . .
C4 C 0.34566(19) 0.3662(6) 0.4787(6) 0.0572(17) Uani 1 1 d . . . . .
C5 C 0.32903(17) 0.3671(5) 0.5962(5) 0.0523(15) Uani 1 1 d . . . . .
H5A H 0.3243 0.4566 0.6151 0.063 Uiso 1 1 calc R U . . .
H5B H 0.3509 0.3373 0.6435 0.063 Uiso 1 1 calc R U . . .
C6 C 0.29051(15) 0.2925(5) 0.6317(5) 0.0563(15) Uani 1 1 d . . . . .
C7 C 0.3142(2) 0.4166(7) 0.3972(6) 0.088(2) Uani 1 1 d . . . . .
H7A H 0.3257 0.4178 0.3243 0.132 Uiso 1 1 calc R U . . .
H7B H 0.3063 0.5024 0.4178 0.132 Uiso 1 1 calc R U . . .
H7C H 0.2908 0.3615 0.3980 0.132 Uiso 1 1 calc R U . . .
C8 C 0.3825(2) 0.4566(7) 0.4742(8) 0.111(3) Uani 1 1 d . . . . .
H8A H 0.3962 0.4460 0.4048 0.167 Uiso 1 1 calc R U . . .
H8B H 0.4008 0.4362 0.5334 0.167 Uiso 1 1 calc R U . . .
H8C H 0.3735 0.5442 0.4814 0.167 Uiso 1 1 calc R U . . .
C9 C 0.2897(2) 0.1546(6) 0.5904(6) 0.084(2) Uani 1 1 d . . . . .
H9A H 0.2889 0.1543 0.5112 0.126 Uiso 1 1 calc R U . . .
H9B H 0.2661 0.1117 0.6188 0.126 Uiso 1 1 calc R U . . .
H9C H 0.3137 0.1105 0.6151 0.126 Uiso 1 1 calc R U . . .
C10 C 0.2917(2) 0.2873(7) 0.7583(6) 0.085(2) Uani 1 1 d . . . . .
H10A H 0.3152 0.2398 0.7817 0.128 Uiso 1 1 calc R U . . .
H10B H 0.2676 0.2455 0.7852 0.128 Uiso 1 1 calc R U . . .
H10C H 0.2930 0.3733 0.7872 0.128 Uiso 1 1 calc R U . . .
C11 C 0.2514(2) 0.3637(8) 0.6005(7) 0.117(3) Uani 1 1 d . . . . .
H11A H 0.2466 0.3551 0.5226 0.176 Uiso 1 1 calc R U . . .
H11B H 0.2540 0.4532 0.6190 0.176 Uiso 1 1 calc R U . . .
H11C H 0.2289 0.3274 0.6404 0.176 Uiso 1 1 calc R U . . .
C12 C 0.41354(17) -0.0732(6) 0.4495(5) 0.0499(15) Uani 1 1 d . . . . .
C13 C 0.45904(17) -0.0436(6) 0.4463(5) 0.0553(17) Uani 1 1 d . . . . .
H13A H 0.4729 -0.1239 0.4623 0.066 Uiso 1 1 calc R U . . .
H13B H 0.4645 0.0134 0.5081 0.066 Uiso 1 1 calc R U . . .
C14 C 0.4808(2) 0.0155(7) 0.3456(6) 0.0599(19) Uani 1 1 d . . . . .
C15 C 0.4012(2) -0.1757(6) 0.3660(7) 0.077(2) Uani 1 1 d . . . . .
H15A H 0.4034 -0.1412 0.2927 0.115 Uiso 1 1 calc R U . . .
H15B H 0.3736 -0.2015 0.3795 0.115 Uiso 1 1 calc R U . . .
H15C H 0.4188 -0.2490 0.3731 0.115 Uiso 1 1 calc R U . . .
C16 C 0.4041(2) -0.1380(7) 0.5674(7) 0.100(3) Uani 1 1 d . . . . .
H16A H 0.3763 -0.1660 0.5696 0.151 Uiso 1 1 calc R U . . .
H16B H 0.4088 -0.0761 0.6250 0.151 Uiso 1 1 calc R U . . .
H16C H 0.4217 -0.2108 0.5782 0.151 Uiso 1 1 calc R U . . .
C17 C 0.4641(2) 0.1445(9) 0.3161(9) 0.131(4) Uani 1 1 d . . . . .
H17A H 0.4845 0.1937 0.2785 0.197 Uiso 1 1 calc R U . . .
H17B H 0.4560 0.1889 0.3822 0.197 Uiso 1 1 calc R U . . .
H17C H 0.4409 0.1340 0.2688 0.197 Uiso 1 1 calc R U . . .
C18 C 0.4814(3) -0.0707(11) 0.2465(7) 0.161(5) Uani 1 1 d . . . . .
H18A H 0.4587 -0.0511 0.1999 0.241 Uiso 1 1 calc R U . . .
H18B H 0.4798 -0.1590 0.2699 0.241 Uiso 1 1 calc R U . . .
H18C H 0.5062 -0.0575 0.2062 0.241 Uiso 1 1 calc R U . . .
C19 C 0.5251(2) 0.0368(8) 0.3781(8) 0.102(3) Uani 1 1 d . . . . .
H19A H 0.5411 0.0510 0.3129 0.153 Uiso 1 1 calc R U . . .
H19B H 0.5351 -0.0379 0.4163 0.153 Uiso 1 1 calc R U . . .
H19C H 0.5270 0.1106 0.4256 0.153 Uiso 1 1 calc R U . . .
C20 C 0.13682(16) 0.6324(5) 0.5030(4) 0.0387(13) Uani 1 1 d . . . . .
C21 C 0.1077(2) 0.5690(7) 0.3473(5) 0.0663(19) Uani 1 1 d . . . . .
H21 H 0.0946 0.5180 0.2952 0.080 Uiso 1 1 calc R U . . .
C22 C 0.12210(19) 0.6871(7) 0.3314(5) 0.0637(18) Uani 1 1 d . . . . .
H22 H 0.1200 0.7344 0.2665 0.076 Uiso 1 1 calc R U . . .
C23 C 0.10177(17) 0.4115(5) 0.5046(5) 0.0489(15) Uani 1 1 d . . . . .
C24 C 0.07423(16) 0.4339(5) 0.6054(5) 0.0488(14) Uani 1 1 d . . . . .
H24A H 0.0696 0.3498 0.6381 0.059 Uiso 1 1 calc R U . . .
H24B H 0.0903 0.4823 0.6582 0.059 Uiso 1 1 calc R U . . .
C25 C 0.03265(17) 0.5000(5) 0.6003(5) 0.0528(16) Uani 1 1 d . . . . .
C26 C 0.0810(2) 0.3310(6) 0.4155(6) 0.076(2) Uani 1 1 d . . . . .
H26A H 0.0600 0.3810 0.3810 0.114 Uiso 1 1 calc R U . . .
H26B H 0.0694 0.2554 0.4483 0.114 Uiso 1 1 calc R U . . .
H26C H 0.1007 0.3060 0.3610 0.114 Uiso 1 1 calc R U . . .
C27 C 0.1399(2) 0.3341(6) 0.5422(7) 0.082(2) Uani 1 1 d . . . . .
H27A H 0.1320 0.2476 0.5604 0.123 Uiso 1 1 calc R U . . .
H27B H 0.1516 0.3746 0.6060 0.123 Uiso 1 1 calc R U . . .
H27C H 0.1595 0.3324 0.4835 0.123 Uiso 1 1 calc R U . . .
C28 C 0.0333(2) 0.6285(7) 0.5421(7) 0.103(3) Uani 1 1 d . . . . .
H28A H 0.0389 0.6156 0.4651 0.155 Uiso 1 1 calc R U . . .
H28B H 0.0540 0.6819 0.5739 0.155 Uiso 1 1 calc R U . . .
H28C H 0.0073 0.6697 0.5503 0.155 Uiso 1 1 calc R U . . .
C29 C -0.0011(2) 0.4148(9) 0.5497(8) 0.110(3) Uani 1 1 d . . . . .
H29A H -0.0251 0.4656 0.5382 0.164 Uiso 1 1 calc R U . . .
H29B H -0.0071 0.3451 0.5991 0.164 Uiso 1 1 calc R U . . .
H29C H 0.0081 0.3808 0.4802 0.164 Uiso 1 1 calc R U . . .
C30 C 0.0192(2) 0.5232(8) 0.7199(6) 0.081(2) Uani 1 1 d . . . . .
H30A H -0.0064 0.5677 0.7202 0.122 Uiso 1 1 calc R U . . .
H30B H 0.0392 0.5744 0.7572 0.122 Uiso 1 1 calc R U . . .
H30C H 0.0163 0.4420 0.7570 0.122 Uiso 1 1 calc R U . . .
C31 C 0.15986(18) 0.8602(6) 0.4413(5) 0.0562(16) Uani 1 1 d . . . . .
C32 C 0.20528(17) 0.8498(6) 0.4717(5) 0.0559(16) Uani 1 1 d . . . . .
H32A H 0.2140 0.9363 0.4907 0.067 Uiso 1 1 calc R U . . .
H32B H 0.2065 0.8000 0.5394 0.067 Uiso 1 1 calc R U . . .
C33 C 0.23855(18) 0.7948(6) 0.3961(6) 0.0559(18) Uani 1 1 d . . . . .
C34 C 0.1542(2) 0.9354(7) 0.3336(6) 0.081(2) Uani 1 1 d . . . . .
H34A H 0.1692 0.8940 0.2755 0.122 Uiso 1 1 calc R U . . .
H34B H 0.1640 1.0218 0.3431 0.122 Uiso 1 1 calc R U . . .
H34C H 0.1258 0.9376 0.3147 0.122 Uiso 1 1 calc R U . . .
C35 C 0.1367(2) 0.9270(6) 0.5361(7) 0.082(2) Uani 1 1 d . . . . .
H35A H 0.1458 1.0146 0.5426 0.123 Uiso 1 1 calc R U . . .
H35B H 0.1418 0.8823 0.6041 0.123 Uiso 1 1 calc R U . . .
H35C H 0.1080 0.9257 0.5207 0.123 Uiso 1 1 calc R U . . .
C36 C 0.2510(2) 0.8900(8) 0.3044(7) 0.101(3) Uani 1 1 d . . . . .
H36A H 0.2780 0.8699 0.2793 0.151 Uiso 1 1 calc R U . . .
H36B H 0.2505 0.9762 0.3329 0.151 Uiso 1 1 calc R U . . .
H36C H 0.2323 0.8830 0.2437 0.151 Uiso 1 1 calc R U . . .
C37 C 0.27579(18) 0.7754(8) 0.4709(7) 0.092(3) Uani 1 1 d . . . . .
H37A H 0.2983 0.7455 0.4274 0.138 Uiso 1 1 calc R U . . .
H37B H 0.2695 0.7130 0.5268 0.138 Uiso 1 1 calc R U . . .
H37C H 0.2828 0.8558 0.5052 0.138 Uiso 1 1 calc R U . . .
C38 C 0.2271(2) 0.6643(6) 0.3476(7) 0.082(2) Uani 1 1 d . . . . .
H38A H 0.2065 0.6757 0.2922 0.123 Uiso 1 1 calc R U . . .
H38B H 0.2168 0.6095 0.4051 0.123 Uiso 1 1 calc R U . . .
H38C H 0.2507 0.6253 0.3150 0.123 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.844(5) . ?
Se2 C20 1.869(5) . ?
N1 C1 1.361(6) . ?
N1 C2 1.388(8) . ?
N1 C4 1.494(7) . ?
N2 C1 1.371(6) . ?
N2 C3 1.398(7) . ?
N2 C12 1.496(7) . ?
N3 C20 1.345(7) . ?
N3 C21 1.384(7) . ?
N3 C23 1.493(7) . ?
N4 C20 1.357(6) . ?
N4 C22 1.368(7) . ?
N4 C31 1.529(7) . ?
C2 C3 1.326(8) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.524(9) . ?
C4 C7 1.523(9) . ?
C4 C8 1.532(9) . ?
C5 C6 1.545(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.516(8) . ?
C6 C10 1.534(9) . ?
C6 C11 1.532(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.523(8) . ?
C12 C13 1.528(7) . ?
C12 C16 1.609(10) . ?
C13 C14 1.541(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C18 1.497(10) . ?
C14 C17 1.491(9) . ?
C14 C19 1.525(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.329(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C26 1.526(8) . ?
C23 C24 1.537(8) . ?
C23 C27 1.556(8) . ?
C24 C25 1.531(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C28 1.508(8) . ?
C25 C30 1.534(8) . ?
C25 C29 1.545(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C34 1.532(9) . ?
C31 C32 1.542(8) . ?
C31 C35 1.543(9) . ?
C32 C33 1.536(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C38 1.524(8) . ?
C33 C37 1.536(9) . ?
C33 C36 1.542(9) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 107.8(5) . . ?
C1 N1 C4 128.4(5) . . ?
C2 N1 C4 123.7(5) . . ?
C1 N2 C3 108.9(5) . . ?
C1 N2 C12 129.5(4) . . ?
C3 N2 C12 121.5(5) . . ?
C20 N3 C21 108.5(5) . . ?
C20 N3 C23 129.4(4) . . ?
C21 N3 C23 122.1(5) . . ?
C20 N4 C22 108.3(5) . . ?
C20 N4 C31 127.8(5) . . ?
C22 N4 C31 123.9(5) . . ?
N1 C1 N2 106.9(4) . . ?
N1 C1 Se1 127.4(4) . . ?
N2 C1 Se1 125.7(4) . . ?
C3 C2 N1 109.7(6) . . ?
C3 C2 H2 125.1 . . ?
N1 C2 H2 125.1 . . ?
C2 C3 N2 106.6(6) . . ?
C2 C3 H3 126.7 . . ?
N2 C3 H3 126.7 . . ?
N1 C4 C5 112.6(5) . . ?
N1 C4 C7 109.5(5) . . ?
C5 C4 C7 111.1(5) . . ?
N1 C4 C8 107.6(5) . . ?
C5 C4 C8 108.3(6) . . ?
C7 C4 C8 107.6(6) . . ?
C4 C5 C6 123.4(5) . . ?
C4 C5 H5A 106.5 . . ?
C6 C5 H5A 106.5 . . ?
C4 C5 H5B 106.5 . . ?
C6 C5 H5B 106.5 . . ?
H5A C5 H5B 106.5 . . ?
C9 C6 C10 107.3(5) . . ?
C9 C6 C11 111.1(6) . . ?
C10 C6 C11 106.5(5) . . ?
C9 C6 C5 113.3(5) . . ?
C10 C6 C5 105.9(5) . . ?
C11 C6 C5 112.2(5) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C15 109.6(5) . . ?
N2 C12 C13 111.9(5) . . ?
C15 C12 C13 112.6(5) . . ?
N2 C12 C16 111.0(5) . . ?
C15 C12 C16 104.2(5) . . ?
C13 C12 C16 107.2(5) . . ?
C12 C13 C14 123.7(5) . . ?
C12 C13 H13A 106.4 . . ?
C14 C13 H13A 106.4 . . ?
C12 C13 H13B 106.4 . . ?
C14 C13 H13B 106.4 . . ?
H13A C13 H13B 106.5 . . ?
C18 C14 C17 110.5(8) . . ?
C18 C14 C19 106.2(6) . . ?
C17 C14 C19 106.5(6) . . ?
C18 C14 C13 113.7(6) . . ?
C17 C14 C13 112.1(5) . . ?
C19 C14 C13 107.3(6) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 N4 107.3(4) . . ?
N3 C20 Se2 126.4(4) . . ?
N4 C20 Se2 126.4(4) . . ?
C22 C21 N3 107.3(6) . . ?
C22 C21 H21 126.3 . . ?
N3 C21 H21 126.3 . . ?
C21 C22 N4 108.5(5) . . ?
C21 C22 H22 125.7 . . ?
N4 C22 H22 125.7 . . ?
N3 C23 C26 109.3(5) . . ?
N3 C23 C24 111.3(4) . . ?
C26 C23 C24 112.4(5) . . ?
N3 C23 C27 108.4(5) . . ?
C26 C23 C27 106.5(5) . . ?
C24 C23 C27 108.7(5) . . ?
C25 C24 C23 124.2(5) . . ?
C25 C24 H24A 106.3 . . ?
C23 C24 H24A 106.3 . . ?
C25 C24 H24B 106.3 . . ?
C23 C24 H24B 106.3 . . ?
H24A C24 H24B 106.4 . . ?
C28 C25 C24 113.8(5) . . ?
C28 C25 C30 107.8(6) . . ?
C24 C25 C30 106.9(5) . . ?
C28 C25 C29 109.3(6) . . ?
C24 C25 C29 113.6(5) . . ?
C30 C25 C29 104.9(6) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N4 C31 C34 108.1(5) . . ?
N4 C31 C32 111.5(4) . . ?
C34 C31 C32 110.9(5) . . ?
N4 C31 C35 106.7(5) . . ?
C34 C31 C35 110.1(5) . . ?
C32 C31 C35 109.4(6) . . ?
C33 C32 C31 125.0(5) . . ?
C33 C32 H32A 106.1 . . ?
C31 C32 H32A 106.1 . . ?
C33 C32 H32B 106.1 . . ?
C31 C32 H32B 106.1 . . ?
H32A C32 H32B 106.3 . . ?
C38 C33 C32 112.6(5) . . ?
C38 C33 C37 108.0(6) . . ?
C32 C33 C37 105.4(6) . . ?
C38 C33 C36 110.9(6) . . ?
C32 C33 C36 112.3(5) . . ?
C37 C33 C36 107.3(5) . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C31 C35 H35A 109.5 . . ?
C31 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C31 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C37 H37A 109.5 . . ?
C33 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C33 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C33 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C33 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -0.5(6) . . . . ?
C4 N1 C1 N2 177.5(5) . . . . ?
C2 N1 C1 Se1 179.8(4) . . . . ?
C4 N1 C1 Se1 -2.2(8) . . . . ?
C3 N2 C1 N1 -0.4(6) . . . . ?
C12 N2 C1 N1 178.9(5) . . . . ?
C3 N2 C1 Se1 179.3(4) . . . . ?
C12 N2 C1 Se1 -1.4(8) . . . . ?
C1 N1 C2 C3 1.3(7) . . . . ?
C4 N1 C2 C3 -176.8(5) . . . . ?
N1 C2 C3 N2 -1.5(7) . . . . ?
C1 N2 C3 C2 1.2(7) . . . . ?
C12 N2 C3 C2 -178.2(5) . . . . ?
C1 N1 C4 C5 -54.4(7) . . . . ?
C2 N1 C4 C5 123.4(6) . . . . ?
C1 N1 C4 C7 -178.5(5) . . . . ?
C2 N1 C4 C7 -0.7(7) . . . . ?
C1 N1 C4 C8 64.8(8) . . . . ?
C2 N1 C4 C8 -117.4(7) . . . . ?
N1 C4 C5 C6 -64.3(7) . . . . ?
C7 C4 C5 C6 58.9(7) . . . . ?
C8 C4 C5 C6 176.9(5) . . . . ?
C4 C5 C6 C9 46.8(8) . . . . ?
C4 C5 C6 C10 164.1(5) . . . . ?
C4 C5 C6 C11 -80.0(7) . . . . ?
C1 N2 C12 C15 174.2(5) . . . . ?
C3 N2 C12 C15 -6.6(7) . . . . ?
C1 N2 C12 C13 -60.2(7) . . . . ?
C3 N2 C12 C13 119.1(6) . . . . ?
C1 N2 C12 C16 59.6(7) . . . . ?
C3 N2 C12 C16 -121.2(6) . . . . ?
N2 C12 C13 C14 -60.0(7) . . . . ?
C15 C12 C13 C14 64.0(8) . . . . ?
C16 C12 C13 C14 178.0(6) . . . . ?
C12 C13 C14 C18 -66.1(9) . . . . ?
C12 C13 C14 C17 60.2(9) . . . . ?
C12 C13 C14 C19 176.8(5) . . . . ?
C21 N3 C20 N4 2.6(6) . . . . ?
C23 N3 C20 N4 -177.4(5) . . . . ?
C21 N3 C20 Se2 -177.9(4) . . . . ?
C23 N3 C20 Se2 2.1(8) . . . . ?
C22 N4 C20 N3 -1.1(6) . . . . ?
C31 N4 C20 N3 176.2(5) . . . . ?
C22 N4 C20 Se2 179.3(4) . . . . ?
C31 N4 C20 Se2 -3.3(8) . . . . ?
C20 N3 C21 C22 -3.1(7) . . . . ?
C23 N3 C21 C22 176.9(5) . . . . ?
N3 C21 C22 N4 2.4(7) . . . . ?
C20 N4 C22 C21 -0.8(7) . . . . ?
C31 N4 C22 C21 -178.3(5) . . . . ?
C20 N3 C23 C26 -176.6(5) . . . . ?
C21 N3 C23 C26 3.4(7) . . . . ?
C20 N3 C23 C24 58.6(7) . . . . ?
C21 N3 C23 C24 -121.4(6) . . . . ?
C20 N3 C23 C27 -60.9(7) . . . . ?
C21 N3 C23 C27 119.1(6) . . . . ?
N3 C23 C24 C25 64.2(7) . . . . ?
C26 C23 C24 C25 -58.8(7) . . . . ?
C27 C23 C24 C25 -176.4(5) . . . . ?
C23 C24 C25 C28 -51.5(8) . . . . ?
C23 C24 C25 C30 -170.4(6) . . . . ?
C23 C24 C25 C29 74.5(7) . . . . ?
C20 N4 C31 C34 -176.4(5) . . . . ?
C22 N4 C31 C34 0.6(7) . . . . ?
C20 N4 C31 C32 61.5(7) . . . . ?
C22 N4 C31 C32 -121.5(6) . . . . ?
C20 N4 C31 C35 -58.0(7) . . . . ?
C22 N4 C31 C35 119.0(6) . . . . ?
N4 C31 C32 C33 65.2(7) . . . . ?
C34 C31 C32 C33 -55.3(8) . . . . ?
C35 C31 C32 C33 -177.0(5) . . . . ?
C31 C32 C33 C38 -49.6(8) . . . . ?
C31 C32 C33 C37 -167.0(6) . . . . ?
C31 C32 C33 C36 76.5(8) . . . . ?

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
C5 H5B Se1 0.97 2.66 3.422(5) 136.2 .
C7 H7A Se2 0.96 3.17 3.901(7) 134.6 4_554

_refine_diff_density_max         1.036
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.050



