# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

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

data_acspbsenet
_database_code_depnum_ccdc_archive 'CCDC 1586974'
loop_
_audit_author_name
_audit_author_address
'Fabian Mohr'
;University of Wuppertal
Germany
;
_audit_update_record             
;
2020-01-27 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H34 N4 O2 Pb Se2'
_chemical_formula_sum            'C26 H34 N4 O2 Pb Se2'
_chemical_formula_weight         799.68
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H44N4Se3Pb1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, z+1/2'
'x, -y, z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'

_cell_length_a                   20.7267(5)
_cell_length_b                   13.0349(11)
_cell_length_c                   10.1701(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2747.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2637
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      29.3314
_cell_measurement_theta_min      3.2013
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4251
_diffrn_reflns_point_group_measured_fraction_full 0.812
_diffrn_reflns_point_group_measured_fraction_max 0.670
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         29.447
_diffrn_reflns_theta_min         3.212
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 16.2705
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00  -20.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3850  106.0000 -161.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -88.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3850    0.0000  -60.0000 132
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0168259000
_diffrn_orient_matrix_UB_12      -0.0141898000
_diffrn_orient_matrix_UB_13      0.0578051000
_diffrn_orient_matrix_UB_21      -0.0149127000
_diffrn_orient_matrix_UB_22      -0.0408761000
_diffrn_orient_matrix_UB_23      -0.0344537000
_diffrn_orient_matrix_UB_31      0.0257339000
_diffrn_orient_matrix_UB_32      -0.0329030000
_diffrn_orient_matrix_UB_33      0.0178309000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.495
_reflns_Friedel_fraction_full    0.602
_reflns_Friedel_fraction_max     0.470
_reflns_number_gt                2256
_reflns_number_total             2543
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.007(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0052P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0461
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.0000 0.5000 0.15160(6) 0.01748(9) Uani 1 2 d S T P . .
Se1 Se -0.05897(3) 0.62608(5) 0.34886(8) 0.01933(15) Uani 1 1 d . . . . .
C1 C -0.1270(3) 0.5414(5) 0.4094(9) 0.0149(15) Uani 1 1 d . . . . .
N1 N -0.1233(2) 0.4397(4) 0.4242(6) 0.0162(15) Uani 1 1 d . . . . .
O1 O 0.09218(19) 0.6028(4) 0.2123(5) 0.0168(10) Uani 1 1 d . . . . .
N2 N -0.1807(2) 0.5863(4) 0.4535(5) 0.0161(12) Uani 1 1 d . . . . .
C6 C 0.1024(2) 0.6240(5) 0.3314(8) 0.0150(14) Uani 1 1 d . . . . .
C7 C 0.0950(2) 0.7336(5) 0.3722(6) 0.0154(17) Uani 1 1 d . . . . .
C11 C 0.0741(4) 0.9091(6) 0.3122(7) 0.027(2) Uani 1 1 d . . . . .
H11 H 0.0617 0.9575 0.2471 0.032 Uiso 1 1 calc R . . . .
C12 C 0.0777(3) 0.8058(6) 0.2791(7) 0.0223(17) Uani 1 1 d . . . . .
H12 H 0.0682 0.7847 0.1918 0.027 Uiso 1 1 calc R . . . .
C4 C -0.1880(3) 0.6964(6) 0.4672(7) 0.0243(18) Uani 1 1 d . . . . .
H4A H -0.1451 0.7277 0.4825 0.029 Uiso 1 1 calc R . . . .
H4B H -0.2153 0.7112 0.5448 0.029 Uiso 1 1 calc R . . . .
C5 C -0.2182(3) 0.7442(6) 0.3466(9) 0.0333(17) Uani 1 1 d . . . . .
H5A H -0.1904 0.7321 0.2702 0.050 Uiso 1 1 calc GR . . . .
H5B H -0.2232 0.8181 0.3603 0.050 Uiso 1 1 calc GR . . . .
H5C H -0.2606 0.7132 0.3309 0.050 Uiso 1 1 calc GR . . . .
C8 C 0.1064(3) 0.7672(6) 0.5001(7) 0.0178(15) Uani 1 1 d . . . . .
H8 H 0.1167 0.7187 0.5666 0.021 Uiso 1 1 calc R . . . .
C10 C 0.0878(3) 0.9423(5) 0.4358(7) 0.0215(18) Uani 1 1 d . . . . .
C9 C 0.1030(3) 0.8685(6) 0.5313(8) 0.0227(17) Uani 1 1 d . . . . .
H9 H 0.1111 0.8896 0.6192 0.027 Uiso 1 1 calc R . . . .
C13 C 0.0870(4) 1.0564(6) 0.4676(8) 0.035(2) Uani 1 1 d . . . . .
H13A H 0.0914 1.0960 0.3862 0.053 Uiso 1 1 calc GR . . . .
H13B H 0.1229 1.0728 0.5267 0.053 Uiso 1 1 calc GR . . . .
H13C H 0.0461 1.0740 0.5105 0.053 Uiso 1 1 calc GR . . . .
C2 C -0.2346(3) 0.4984(8) 0.6412(15) 0.0318(17) Uani 1 1 d . . . . .
H2A H -0.1963 0.4569 0.6606 0.048 Uiso 1 1 calc GR . . . .
H2B H -0.2735 0.4597 0.6645 0.048 Uiso 1 1 calc GR . . . .
H2C H -0.2331 0.5620 0.6925 0.048 Uiso 1 1 calc GR . . . .
C3 C -0.2360(3) 0.5239(6) 0.4967(7) 0.0204(17) Uani 1 1 d . . . . .
H3A H -0.2366 0.4593 0.4456 0.025 Uiso 1 1 calc R . . . .
H3B H -0.2763 0.5615 0.4769 0.025 Uiso 1 1 calc R . . . .


_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
Pb1 Se1 2.8669(8) . ?
Pb1 Se1 2.8669(8) 2_565 ?
Pb1 O1 2.414(4) 2_565 ?
Pb1 O1 2.414(4) . ?
Se1 C1 1.894(6) . ?
C1 N1 1.335(8) . ?
C1 N2 1.335(8) . ?
N1 C6 1.330(8) 2_565 ?
O1 C6 1.259(9) . ?
N2 C4 1.450(9) . ?
N2 C3 1.472(8) . ?
C6 N1 1.330(8) 2_565 ?
C6 C7 1.496(8) . ?
C7 C12 1.383(9) . ?
C7 C8 1.393(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(11) . ?
C11 C10 1.360(10) . ?
C12 H12 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.512(10) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.360(10) . ?
C10 C9 1.402(10) . ?
C10 C13 1.522(10) . ?
C9 H9 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C3 1.507(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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
Se1 Pb1 Se1 91.18(3) . 2_565 ?
O1 Pb1 Se1 78.56(11) . 2_565 ?
O1 Pb1 Se1 78.56(11) 2_565 . ?
O1 Pb1 Se1 80.80(11) 2_565 2_565 ?
O1 Pb1 Se1 80.80(11) . . ?
O1 Pb1 O1 150.3(2) 2_565 . ?
C1 Se1 Pb1 102.2(2) . . ?
N1 C1 Se1 124.9(5) . . ?
N2 C1 Se1 118.3(5) . . ?
N2 C1 N1 116.5(6) . . ?
C6 N1 C1 123.9(6) 2_565 . ?
C6 O1 Pb1 120.1(4) . . ?
C1 N2 C4 123.6(5) . . ?
C1 N2 C3 120.4(5) . . ?
C4 N2 C3 115.9(5) . . ?
N1 C6 C7 115.6(6) 2_565 . ?
O1 C6 N1 126.9(6) . 2_565 ?
O1 C6 C7 117.3(6) . . ?
C12 C7 C6 119.1(6) . . ?
C12 C7 C8 118.0(6) . . ?
C8 C7 C6 122.8(6) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.5(7) . . ?
C7 C12 C11 120.5(7) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N2 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
N2 C4 C5 111.9(6) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.9(7) . . ?
C9 C8 H8 119.5 . . ?
C11 C10 C9 117.9(7) . . ?
C11 C10 C13 120.4(7) . . ?
C9 C10 C13 121.7(7) . . ?
C8 C9 C10 121.1(7) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
N2 C3 C2 113.4(5) . . ?
N2 C3 H3A 108.9 . . ?
N2 C3 H3B 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?

_olex2_date_sample_data_collection 2011-05-25
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/Hexanes'
####################################################################### 
# 
# 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_kk010_1
_database_code_depnum_ccdc_archive 'CCDC 1586977'
loop_
_audit_author_name
_audit_author_address
'Fabian Mohr'
;University of Wuppertal
Germany
;
_audit_update_record             
;
2020-01-27 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H23 Cl N2 O Se'
_chemical_formula_sum            'C16 H23 Cl N2 O Se'
_chemical_formula_weight         373.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H19O1N2Se1Cl1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

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

_cell_length_a                   8.1942(7)
_cell_length_b                   10.8431(8)
_cell_length_c                   11.8118(12)
_cell_angle_alpha                64.775(8)
_cell_angle_beta                 69.712(8)
_cell_angle_gamma                80.596(6)
_cell_volume                     890.36(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3250
_cell_measurement_temperature    149.9
_cell_measurement_theta_max      29.3607
_cell_measurement_theta_min      2.9151
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7450
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         29.425
_diffrn_reflns_theta_min         2.921
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.2705
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   26.00   53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9787   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   -6.00   20.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9787   81.0000  106.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -26.00   48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9787    0.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega  -90.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5412  -77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega  -45.00   50.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5412   77.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  6 omega  -82.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5412  -77.0000  120.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0844638000
_diffrn_orient_matrix_UB_12      0.0046893000
_diffrn_orient_matrix_UB_13      0.0425264000
_diffrn_orient_matrix_UB_21      -0.0372251000
_diffrn_orient_matrix_UB_22      -0.0071242000
_diffrn_orient_matrix_UB_23      -0.0428393000
_diffrn_orient_matrix_UB_31      -0.0001117000
_diffrn_orient_matrix_UB_32      -0.0718176000
_diffrn_orient_matrix_UB_33      0.0351078000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3604
_reflns_number_total             4067
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0225P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0699
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C8(H8), C5(H5), C7(H7)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.96346(3) 0.79335(2) 0.66307(2) 0.02168(8) Uani 1 1 d . . . . .
N2 N 0.6487(2) 0.83907(17) 0.83629(17) 0.0169(4) Uani 1 1 d . . . . .
N1 N 0.7876(2) 1.03498(17) 0.66604(17) 0.0185(4) Uani 1 1 d . . . . .
H1 H 0.8007 1.0719 0.5812 0.022 Uiso 1 1 calc R . . . .
C1 C 0.7841(3) 0.8926(2) 0.7312(2) 0.0166(4) Uani 1 1 d . . . . .
O1 O 0.75328(19) 1.07677(15) 0.84698(14) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.7712(2) 1.1200(2) 0.7301(2) 0.0182(4) Uani 1 1 d . . . . .
C4 C 0.7203(3) 1.3228(2) 0.5346(2) 0.0210(5) Uani 1 1 d . . . . .
H4 H 0.6928 1.2635 0.5037 0.025 Uiso 1 1 calc R . . . .
C6 C 0.7501(3) 1.5475(2) 0.5137(2) 0.0264(5) Uani 1 1 d . . . . .
C3 C 0.7701(3) 1.2691(2) 0.6476(2) 0.0186(4) Uani 1 1 d . . . . .
C8 C 0.8099(3) 1.3568(2) 0.6924(2) 0.0237(5) Uani 1 1 d . . . . .
H8 H 0.8445 1.3201 0.7696 0.028 Uiso 1 1 calc R . . . .
C5 C 0.7105(3) 1.4632(2) 0.4665(2) 0.0251(5) Uani 1 1 d . . . . .
H5 H 0.6772 1.5006 0.3888 0.030 Uiso 1 1 calc R . . . .
C7 C 0.7996(3) 1.4967(2) 0.6259(2) 0.0274(5) Uani 1 1 d . . . . .
H7 H 0.8261 1.5564 0.6568 0.033 Uiso 1 1 calc R . . . .
Cl1 Cl 0.73467(9) 1.72322(6) 0.43004(7) 0.03955(17) Uani 1 1 d . . . . .
C13 C 0.4798(2) 0.9115(2) 0.8651(2) 0.0195(4) Uani 1 1 d . . . . .
H13A H 0.4965 1.0109 0.8141 0.023 Uiso 1 1 calc R . . . .
H13B H 0.4368 0.8941 0.9598 0.023 Uiso 1 1 calc R . . . .
C10 C 0.7655(3) 0.6588(2) 1.0099(2) 0.0251(5) Uani 1 1 d . . . . .
H10 H 0.8875 0.6846 0.9519 0.030 Uiso 1 1 calc R . . . .
C14 C 0.3447(3) 0.8652(2) 0.8301(2) 0.0237(5) Uani 1 1 d . . . . .
H14 H 0.3295 0.7648 0.8818 0.028 Uiso 1 1 calc R . . . .
C9 C 0.6509(3) 0.6931(2) 0.9224(2) 0.0224(5) Uani 1 1 d . . . . .
H9A H 0.6928 0.6398 0.8671 0.027 Uiso 1 1 calc R . . . .
H9B H 0.5305 0.6650 0.9789 0.027 Uiso 1 1 calc R . . . .
C11 C 0.7096(3) 0.7366(3) 1.0985(2) 0.0339(6) Uani 1 1 d . . . . .
H11A H 0.7119 0.8347 1.0443 0.051 Uiso 1 1 calc GR . . . .
H11B H 0.7895 0.7144 1.1502 0.051 Uiso 1 1 calc GR . . . .
H11C H 0.5913 0.7108 1.1580 0.051 Uiso 1 1 calc GR . . . .
C12 C 0.7628(4) 0.5041(2) 1.0896(3) 0.0398(7) Uani 1 1 d . . . . .
H12A H 0.6434 0.4763 1.1451 0.060 Uiso 1 1 calc GR . . . .
H12B H 0.8379 0.4797 1.1452 0.060 Uiso 1 1 calc GR . . . .
H12C H 0.8052 0.4576 1.0293 0.060 Uiso 1 1 calc GR . . . .
C15 C 0.4034(3) 0.8938(3) 0.6845(3) 0.0455(7) Uani 1 1 d . . . . .
H15A H 0.3108 0.8696 0.6633 0.068 Uiso 1 1 calc GR . . . .
H15B H 0.5084 0.8393 0.6638 0.068 Uiso 1 1 calc GR . . . .
H15C H 0.4288 0.9908 0.6325 0.068 Uiso 1 1 calc GR . . . .
C16 C 0.1716(3) 0.9371(3) 0.8700(2) 0.0307(6) Uani 1 1 d . . . . .
H16A H 0.1850 1.0359 0.8213 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.1358 0.9148 0.9647 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.0829 0.9068 0.8497 0.046 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.835(2) . ?
N2 C1 1.322(3) . ?
N2 C13 1.482(2) . ?
N2 C9 1.474(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.401(3) . ?
N1 C2 1.387(3) . ?
O1 C2 1.216(3) . ?
C2 C3 1.491(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.387(3) . ?
C4 C5 1.390(3) . ?
C6 C5 1.380(3) . ?
C6 C7 1.379(3) . ?
C6 Cl1 1.740(2) . ?
C3 C8 1.393(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.383(3) . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.524(3) . ?
C10 H10 1.0000 . ?
C10 C9 1.523(3) . ?
C10 C11 1.519(3) . ?
C10 C12 1.533(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.519(3) . ?
C14 C16 1.526(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C13 123.97(17) . . ?
C1 N2 C9 120.02(17) . . ?
C9 N2 C13 115.40(16) . . ?
C1 N1 H1 118.7 . . ?
C2 N1 H1 118.7 . . ?
C2 N1 C1 122.56(17) . . ?
N2 C1 Se1 124.54(15) . . ?
N2 C1 N1 117.35(18) . . ?
N1 C1 Se1 118.09(14) . . ?
N1 C2 C3 115.81(18) . . ?
O1 C2 N1 122.60(19) . . ?
O1 C2 C3 121.6(2) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C5 C6 Cl1 118.99(19) . . ?
C7 C6 C5 122.1(2) . . ?
C7 C6 Cl1 118.94(19) . . ?
C4 C3 C2 122.7(2) . . ?
C4 C3 C8 119.6(2) . . ?
C8 C3 C2 117.6(2) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 C3 120.7(2) . . ?
C7 C8 H8 119.6 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 120.5 . . ?
C6 C7 C8 118.5(2) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
N2 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
N2 C13 C14 111.48(17) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C9 C10 H10 108.2 . . ?
C9 C10 C12 108.2(2) . . ?
C11 C10 H10 108.2 . . ?
C11 C10 C9 112.24(19) . . ?
C11 C10 C12 111.8(2) . . ?
C12 C10 H10 108.2 . . ?
C13 C14 H14 108.5 . . ?
C13 C14 C16 108.67(19) . . ?
C15 C14 C13 111.06(19) . . ?
C15 C14 H14 108.5 . . ?
C15 C14 C16 111.4(2) . . ?
C16 C14 H14 108.5 . . ?
N2 C9 C10 113.42(18) . . ?
N2 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_date_sample_data_collection 2011-09-27
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_kk007
_database_code_depnum_ccdc_archive 'CCDC 1586975'
loop_
_audit_author_name
_audit_author_address
'Fabian Mohr'
;University of Wuppertal
Germany
;
_audit_update_record             
;
2020-01-27 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H23 Cl N2 O Se'
_chemical_formula_sum            'C16 H23 Cl N2 O Se'
_chemical_formula_weight         373.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H14Cl1O1Se1N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6871(5)
_cell_length_b                   15.8440(6)
_cell_length_c                   10.4873(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.813(4)
_cell_angle_gamma                90
_cell_volume                     1724.43(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4218
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.2370
_cell_measurement_theta_min      3.1128
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8277
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         29.302
_diffrn_reflns_theta_min         3.235
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.2705
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    5.00   76.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       17.8225   77.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   80.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       17.8225    0.0000  -60.0000 123

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   48.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3850   77.0000   90.0000 59
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0596677000
_diffrn_orient_matrix_UB_12      0.0218066000
_diffrn_orient_matrix_UB_13      -0.0145498000
_diffrn_orient_matrix_UB_21      0.0045830000
_diffrn_orient_matrix_UB_22      0.0055171000
_diffrn_orient_matrix_UB_23      0.0680916000
_diffrn_orient_matrix_UB_31      0.0329361000
_diffrn_orient_matrix_UB_32      0.0387242000
_diffrn_orient_matrix_UB_33      -0.0014938000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3392
_reflns_number_total             3951
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²+1.4217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0758
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C9(H9A,H9B), C11(H11A,H11B), C10(H10A,H10B),
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), N1(H1), C4(H4), C7(H7), C5(H5)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.18219(2) 0.07244(2) 0.01492(2) 0.02201(8) Uani 1 1 d . . . . .
Cl1 Cl -0.55486(6) -0.02712(4) 0.30667(7) 0.03875(17) Uani 1 1 d . . . . .
C1 C 0.0982(2) 0.13774(13) 0.1139(2) 0.0180(4) Uani 1 1 d . . . . .
C8 C -0.1774(2) 0.01454(14) 0.3801(2) 0.0217(4) Uani 1 1 d . . . . .
H8 H -0.1035 0.0025 0.4484 0.026 Uiso 1 1 calc R . . . .
N1 N -0.01443(17) 0.10368(11) 0.14077(17) 0.0191(4) Uani 1 1 d . . . . .
H1 H -0.0782 0.0908 0.0735 0.023 Uiso 1 1 calc R . . . .
C2 C -0.0319(2) 0.08897(13) 0.2655(2) 0.0179(4) Uani 1 1 d . . . . .
N2 N 0.13106(18) 0.21520(11) 0.15636(18) 0.0208(4) Uani 1 1 d . . . . .
C4 C -0.2726(2) 0.07605(14) 0.1695(2) 0.0228(5) Uani 1 1 d . . . . .
H4 H -0.2642 0.1061 0.0936 0.027 Uiso 1 1 calc R . . . .
C13 C 0.0517(2) 0.26967(14) 0.2214(2) 0.0227(5) Uani 1 1 d . . . . .
H13A H 0.1060 0.3164 0.2670 0.027 Uiso 1 1 calc R . . . .
H13B H 0.0228 0.2360 0.2886 0.027 Uiso 1 1 calc R . . . .
C3 C -0.1633(2) 0.05858(13) 0.2694(2) 0.0184(4) Uani 1 1 d . . . . .
C6 C -0.4039(2) 0.00608(14) 0.2917(2) 0.0237(5) Uani 1 1 d . . . . .
C7 C -0.2973(2) -0.01191(14) 0.3921(2) 0.0243(5) Uani 1 1 d . . . . .
H7 H -0.3064 -0.0419 0.4678 0.029 Uiso 1 1 calc R . . . .
C15 C -0.1374(3) 0.36737(16) 0.1978(2) 0.0310(5) Uani 1 1 d . . . . .
H15A H -0.0767 0.4115 0.2417 0.037 Uiso 1 1 calc R . . . .
H15B H -0.2068 0.3955 0.1320 0.037 Uiso 1 1 calc R . . . .
C9 C 0.2444(2) 0.25811(16) 0.1284(3) 0.0309(5) Uani 1 1 d . . . . .
H9A H 0.2155 0.3109 0.0797 0.037 Uiso 1 1 calc R . . . .
H9B H 0.2818 0.2214 0.0707 0.037 Uiso 1 1 calc R . . . .
C5 C -0.3933(2) 0.04975(15) 0.1806(2) 0.0259(5) Uani 1 1 d . . . . .
H5 H -0.4677 0.0616 0.1129 0.031 Uiso 1 1 calc R . . . .
C11 C 0.3988(3) 0.2040(2) 0.3304(3) 0.0465(7) Uani 1 1 d . . . . .
H11A H 0.4237 0.1605 0.2733 0.056 Uiso 1 1 calc R . . . .
H11B H 0.3295 0.1802 0.3674 0.056 Uiso 1 1 calc R . . . .
C10 C 0.3484(3) 0.27936(18) 0.2494(3) 0.0388(6) Uani 1 1 d . . . . .
H10A H 0.4205 0.3075 0.2221 0.047 Uiso 1 1 calc R . . . .
H10B H 0.3132 0.3198 0.3039 0.047 Uiso 1 1 calc R . . . .
C12 C 0.5174(3) 0.2248(2) 0.4448(3) 0.0560(9) Uani 1 1 d . . . . .
H12A H 0.5865 0.2484 0.4088 0.084 Uiso 1 1 calc GR . . . .
H12B H 0.5479 0.1731 0.4936 0.084 Uiso 1 1 calc GR . . . .
H12C H 0.4924 0.2660 0.5038 0.084 Uiso 1 1 calc GR . . . .
O1 O 0.05207(15) 0.10202(10) 0.36537(15) 0.0241(3) Uani 1 1 d . . . . .
C16 C -0.1959(3) 0.32485(19) 0.2989(3) 0.0409(7) Uani 1 1 d . . . . .
H16A H -0.2567 0.2813 0.2562 0.061 Uiso 1 1 calc GR . . . .
H16B H -0.2414 0.3669 0.3395 0.061 Uiso 1 1 calc GR . . . .
H16C H -0.1275 0.2988 0.3666 0.061 Uiso 1 1 calc GR . . . .
C14 C -0.0658(2) 0.30676(16) 0.1266(2) 0.0276(5) Uani 1 1 d . . . . .
H14A H -0.1244 0.2606 0.0863 0.033 Uiso 1 1 calc R . . . .
H14B H -0.0383 0.3373 0.0556 0.033 Uiso 1 1 calc R . . . .


_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(2) . ?
Cl1 C6 1.740(2) . ?
C1 N1 1.408(3) . ?
C1 N2 1.324(3) . ?
C8 H8 0.9500 . ?
C8 C3 1.393(3) . ?
C8 C7 1.382(3) . ?
N1 H1 0.8800 . ?
N1 C2 1.385(3) . ?
C2 C3 1.494(3) . ?
C2 O1 1.223(3) . ?
N2 C13 1.485(3) . ?
N2 C9 1.478(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.398(3) . ?
C4 C5 1.387(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.521(3) . ?
C6 C7 1.383(3) . ?
C6 C5 1.382(3) . ?
C7 H7 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.513(3) . ?
C15 C14 1.529(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(4) . ?
C5 H5 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.490(4) . ?
C11 C12 1.558(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 Se1 116.87(15) . . ?
N2 C1 Se1 125.72(16) . . ?
N2 C1 N1 117.32(18) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C3 120.9(2) . . ?
C1 N1 H1 117.7 . . ?
C2 N1 C1 124.63(18) . . ?
C2 N1 H1 117.7 . . ?
N1 C2 C3 114.80(18) . . ?
O1 C2 N1 122.91(19) . . ?
O1 C2 C3 122.27(19) . . ?
C1 N2 C13 123.95(18) . . ?
C1 N2 C9 121.58(19) . . ?
C9 N2 C13 114.12(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.3(2) . . ?
N2 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
N2 C13 C14 113.42(18) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C8 C3 C2 118.22(19) . . ?
C8 C3 C4 119.1(2) . . ?
C4 C3 C2 122.59(19) . . ?
C7 C6 Cl1 118.81(18) . . ?
C5 C6 Cl1 119.42(18) . . ?
C5 C6 C7 121.8(2) . . ?
C8 C7 C6 118.8(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C16 C15 C14 113.7(2) . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
N2 C9 H9A 108.7 . . ?
N2 C9 H9B 108.7 . . ?
N2 C9 C10 114.1(2) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
H11A C11 H11B 107.8 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C10 C11 C12 112.7(3) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 C9 113.2(2) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 C15 110.82(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?

_olex2_date_sample_data_collection 2011-09-06
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_acspbsemear
_database_code_depnum_ccdc_archive 'CCDC 1586978'
loop_
_audit_author_name
_audit_author_address
'Fabian Mohr' 'University of Wuppertal'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H28 N6 O6 Pb Se2'
_chemical_formula_sum            'C32 H28 N6 O6 Pb Se2'
_chemical_formula_weight         957.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H28N6O2Se2Pb1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.1737(2)
_cell_length_b                   14.1942(2)
_cell_length_c                   16.5168(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.0944(16)
_cell_angle_gamma                90
_cell_volume                     3309.79(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6569
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.3402
_cell_measurement_theta_min      3.0314
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13648
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         29.405
_diffrn_reflns_theta_min         3.105
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.2705
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00   11.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3850  -77.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00   35.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3850    0.0000    0.0000 107
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0383736000
_diffrn_orient_matrix_UB_12      -0.0077614000
_diffrn_orient_matrix_UB_13      0.0298242000
_diffrn_orient_matrix_UB_21      -0.0278615000
_diffrn_orient_matrix_UB_22      0.0169785000
_diffrn_orient_matrix_UB_23      0.0305052000
_diffrn_orient_matrix_UB_31      -0.0166251000
_diffrn_orient_matrix_UB_32      -0.0463528000
_diffrn_orient_matrix_UB_33      0.0061707000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6269
_reflns_number_total             7523
_reflns_odcompleteness_completeness 98.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.492
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         7523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²+0.0568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0700
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C32(H32), C22(H22), C31(H31), C3(H3), C4(H4), C29(H29),
 C16(H16), C7(H7), C28(H28), C12(H12), C6(H6), C15(H15), C13(H13), C20(H20)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 1.11462(2) 0.01103(2) 0.58609(2) 0.02330(5) Uani 1 1 d . . . . .
Se2 Se 1.21977(3) 0.16662(3) 0.64717(2) 0.02277(9) Uani 1 1 d . . . . .
Se1 Se 0.94336(3) 0.06837(3) 0.63697(2) 0.02429(10) Uani 1 1 d . . . . .
O4 O 1.0527(2) 0.14278(18) 0.50052(14) 0.0245(6) Uani 1 1 d . . . . .
C25 C 1.1071(3) 0.2384(3) 0.6510(2) 0.0201(8) Uani 1 1 d . . . . .
N5 N 1.0795(2) 0.2620(2) 0.72310(17) 0.0192(7) Uani 1 1 d . . . . .
O1 O 1.1143(2) -0.06898(18) 0.72029(15) 0.0266(6) Uani 1 1 d . . . . .
C10 C 1.0595(3) -0.0725(3) 0.7755(2) 0.0222(8) Uani 1 1 d . . . . .
N4 N 1.0581(2) 0.2731(2) 0.58516(17) 0.0203(7) Uani 1 1 d . . . . .
C19 C 1.1412(3) 0.1409(3) 0.9197(2) 0.0267(9) Uani 1 1 d . . . . .
H19 H 1.1173 0.0913 0.9506 0.032 Uiso 1 1 calc R . . . .
C23 C 1.2566(3) 0.2594(3) 0.9026(2) 0.0280(9) Uani 1 1 d . . . . .
H23 H 1.3126 0.2922 0.9219 0.034 Uiso 1 1 calc R . . . .
C32 C 0.9820(3) 0.3824(3) 0.4509(2) 0.0225(8) Uani 1 1 d . . . . .
H32 H 0.9833 0.4099 0.5035 0.027 Uiso 1 1 calc R . . . .
C9 C 0.9108(3) -0.0293(3) 0.7088(2) 0.0240(9) Uani 1 1 d . . . . .
N2 N 0.8193(2) -0.0552(3) 0.70074(19) 0.0301(8) Uani 1 1 d . . . . .
C26 C 1.0454(3) 0.2300(3) 0.5135(2) 0.0207(8) Uani 1 1 d . . . . .
C22 C 1.2117(3) 0.2826(3) 0.8272(2) 0.0227(8) Uani 1 1 d . . . . .
H22 H 1.2366 0.3307 0.7953 0.027 Uiso 1 1 calc R . . . .
N1 N 0.9650(2) -0.0673(2) 0.76897(18) 0.0250(8) Uani 1 1 d . . . . .
C31 C 0.9495(3) 0.4338(3) 0.3839(2) 0.0230(8) Uani 1 1 d . . . . .
H31 H 0.9270 0.4963 0.3894 0.028 Uiso 1 1 calc R . . . .
C3 C 0.6643(3) -0.0037(3) 0.5142(3) 0.0304(10) Uani 1 1 d . . . . .
H3 H 0.6508 -0.0296 0.4613 0.036 Uiso 1 1 calc R . . . .
C4 C 0.7290(3) -0.0487(3) 0.5681(2) 0.0267(9) Uani 1 1 d . . . . .
H4 H 0.7586 -0.1055 0.5531 0.032 Uiso 1 1 calc R . . . .
C29 C 0.9808(3) 0.3027(3) 0.2974(2) 0.0284(9) Uani 1 1 d . . . . .
H29 H 0.9806 0.2763 0.2445 0.034 Uiso 1 1 calc R . . . .
C2 C 0.6184(3) 0.0776(3) 0.5343(2) 0.0296(10) Uani 1 1 d . . . . .
O5 O 0.9298(2) 0.4158(2) 0.16925(16) 0.0369(7) Uani 1 1 d . . . . .
C16 C 1.2001(3) -0.0807(3) 0.8779(2) 0.0260(9) Uani 1 1 d . . . . .
H16 H 1.2387 -0.0636 0.8360 0.031 Uiso 1 1 calc R . . . .
C18 C 1.2220(3) 0.1898(3) 0.9502(2) 0.0244(9) Uani 1 1 d . . . . .
O2 O 1.1780(3) -0.1711(3) 1.1478(2) 0.0782(14) Uani 1 1 d . . . . .
C30 C 0.9501(3) 0.3929(3) 0.3080(2) 0.0216(8) Uani 1 1 d . . . . .
C27 C 1.0131(3) 0.2901(3) 0.4424(2) 0.0193(8) Uani 1 1 d . . . . .
C7 C 0.6399(3) 0.1136(3) 0.6125(3) 0.0348(10) Uani 1 1 d . . . . .
H7 H 0.6089 0.1690 0.6285 0.042 Uiso 1 1 calc R . . . .
C24 C 0.9879(3) 0.3101(3) 0.7293(2) 0.0277(9) Uani 1 1 d . . . . .
H24A H 0.9768 0.3554 0.6847 0.042 Uiso 1 1 calc GR . . . .
H24B H 0.9893 0.3433 0.7814 0.042 Uiso 1 1 calc GR . . . .
H24C H 0.9368 0.2634 0.7260 0.042 Uiso 1 1 calc GR . . . .
C28 C 1.0119(3) 0.2510(3) 0.3654(2) 0.0265(9) Uani 1 1 d . . . . .
H28 H 1.0326 0.1879 0.3593 0.032 Uiso 1 1 calc R . . . .
C1 C 0.5465(3) 0.1255(3) 0.4760(3) 0.0428(12) Uani 1 1 d . . . . .
H1A H 0.5768 0.1772 0.4488 0.064 Uiso 1 1 calc GR . . . .
H1B H 0.4953 0.1506 0.5058 0.064 Uiso 1 1 calc GR . . . .
H1C H 0.5205 0.0800 0.4353 0.064 Uiso 1 1 calc GR . . . .
C5 C 0.7504(3) -0.0097(3) 0.6447(2) 0.0263(9) Uani 1 1 d . . . . .
C12 C 1.0467(3) -0.1188(3) 0.9208(2) 0.0375(11) Uani 1 1 d . . . . .
H12 H 0.9803 -0.1262 0.9088 0.045 Uiso 1 1 calc R . . . .
C6 C 0.7051(3) 0.0701(3) 0.6665(3) 0.0351(11) Uani 1 1 d . . . . .
H6 H 0.7188 0.0957 0.7194 0.042 Uiso 1 1 calc R . . . .
C15 C 1.2403(3) -0.0942(3) 0.9564(2) 0.0334(10) Uani 1 1 d . . . . .
H15 H 1.3064 -0.0857 0.9693 0.040 Uiso 1 1 calc R . . . .
N3 N 1.2248(3) -0.1322(3) 1.1000(2) 0.0495(12) Uani 1 1 d . . . . .
O3 O 1.3034(3) -0.0994(4) 1.1172(2) 0.0759(14) Uani 1 1 d . . . . .
C13 C 1.0879(4) -0.1347(4) 0.9996(3) 0.0456(13) Uani 1 1 d . . . . .
H13 H 1.0508 -0.1552 1.0413 0.055 Uiso 1 1 calc R . . . .
C20 C 1.0953(3) 0.1642(3) 0.8443(2) 0.0247(9) Uani 1 1 d . . . . .
H20 H 1.0397 0.1313 0.8242 0.030 Uiso 1 1 calc R . . . .
C21 C 1.1307(3) 0.2350(3) 0.7990(2) 0.0194(8) Uani 1 1 d . . . . .
C11 C 1.1026(3) -0.0923(3) 0.8603(2) 0.0239(9) Uani 1 1 d . . . . .
C14 C 1.1831(3) -0.1201(3) 1.0151(2) 0.0321(10) Uani 1 1 d . . . . .
C17 C 1.2681(3) 0.1683(4) 1.0343(2) 0.0400(12) Uani 1 1 d . . . . .
H17A H 1.2272 0.1905 1.0751 0.060 Uiso 1 1 calc GR . . . .
H17B H 1.3295 0.2002 1.0420 0.060 Uiso 1 1 calc GR . . . .
H17C H 1.2774 0.1001 1.0401 0.060 Uiso 1 1 calc GR . . . .
C8 C 0.7827(4) -0.1269(4) 0.7534(3) 0.0549(15) Uani 1 1 d . . . . .
H8A H 0.7671 -0.0977 0.8043 0.082 Uiso 1 1 calc GR . . . .
H8B H 0.8308 -0.1757 0.7653 0.082 Uiso 1 1 calc GR . . . .
H8C H 0.7255 -0.1554 0.7259 0.082 Uiso 1 1 calc GR . . . .
O6 O 0.8712(3) 0.5202(2) 0.2463(2) 0.0411(8) Uani 1 1 d . . . . .
N6 N 0.9151(2) 0.4469(3) 0.2356(2) 0.0291(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pb1 Se2 2.8017(4) . ?
Pb1 Se1 2.7610(4) . ?
Pb1 O4 2.459(3) . ?
Pb1 O1 2.491(2) . ?
Se2 C25 1.900(4) . ?
Se1 C9 1.908(4) . ?
O4 C26 1.262(4) . ?
C25 N5 1.328(4) . ?
C25 N4 1.332(5) . ?
N5 C24 1.479(5) . ?
N5 C21 1.443(4) . ?
O1 C10 1.250(4) . ?
C10 N1 1.336(5) . ?
C10 C11 1.504(5) . ?
N4 C26 1.330(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.394(6) . ?
C19 C20 1.394(5) . ?
C23 H23 0.9500 . ?
C23 C22 1.387(5) . ?
C23 C18 1.380(5) . ?
C32 H32 0.9500 . ?
C32 C31 1.372(5) . ?
C32 C27 1.394(5) . ?
C9 N2 1.343(5) . ?
C9 N1 1.317(5) . ?
N2 C5 1.437(5) . ?
N2 C8 1.464(5) . ?
C26 C27 1.491(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.377(5) . ?
C31 H31 0.9500 . ?
C31 C30 1.381(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(6) . ?
C3 C2 1.380(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.369(6) . ?
C29 C28 1.380(5) . ?
C2 C7 1.398(6) . ?
C2 C1 1.501(6) . ?
O5 N6 1.217(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.382(6) . ?
C16 C11 1.397(6) . ?
C18 C17 1.511(5) . ?
O2 N3 1.209(5) . ?
C30 N6 1.470(5) . ?
C27 C28 1.387(5) . ?
C7 H7 0.9500 . ?
C7 C6 1.373(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C28 H28 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C5 C6 1.367(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.397(6) . ?
C12 C11 1.380(5) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.368(6) . ?
N3 O3 1.218(6) . ?
N3 C14 1.483(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.366(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O6 N6 1.232(4) . ?

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
Se1 Pb1 Se2 96.429(12) . . ?
O4 Pb1 Se2 76.05(6) . . ?
O4 Pb1 Se1 70.85(6) . . ?
O4 Pb1 O1 146.04(8) . . ?
O1 Pb1 Se2 94.70(7) . . ?
O1 Pb1 Se1 78.01(6) . . ?
C25 Se2 Pb1 90.74(11) . . ?
C9 Se1 Pb1 104.06(12) . . ?
C26 O4 Pb1 132.7(2) . . ?
N5 C25 Se2 118.7(3) . . ?
N5 C25 N4 117.7(3) . . ?
N4 C25 Se2 123.3(3) . . ?
C25 N5 C24 120.6(3) . . ?
C25 N5 C21 123.1(3) . . ?
C21 N5 C24 116.0(3) . . ?
C10 O1 Pb1 135.9(2) . . ?
O1 C10 N1 128.5(4) . . ?
O1 C10 C11 117.4(4) . . ?
N1 C10 C11 114.0(3) . . ?
C26 N4 C25 125.1(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C20 C19 C18 120.6(4) . . ?
C22 C23 H23 119.2 . . ?
C18 C23 H23 119.2 . . ?
C18 C23 C22 121.6(4) . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C27 120.3(4) . . ?
C27 C32 H32 119.8 . . ?
N2 C9 Se1 115.0(3) . . ?
N1 C9 Se1 127.6(3) . . ?
N1 C9 N2 117.2(4) . . ?
C9 N2 C5 122.4(3) . . ?
C9 N2 C8 121.4(4) . . ?
C5 N2 C8 116.0(4) . . ?
O4 C26 N4 126.6(3) . . ?
O4 C26 C27 116.8(3) . . ?
N4 C26 C27 116.4(3) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 C23 119.3(4) . . ?
C21 C22 H22 120.4 . . ?
C9 N1 C10 126.7(3) . . ?
C32 C31 H31 120.7 . . ?
C32 C31 C30 118.7(3) . . ?
C30 C31 H31 120.7 . . ?
C4 C3 H3 118.9 . . ?
C4 C3 C2 122.3(4) . . ?
C2 C3 H3 118.9 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C30 C29 H29 120.8 . . ?
C30 C29 C28 118.3(4) . . ?
C28 C29 H29 120.8 . . ?
C3 C2 C7 117.4(4) . . ?
C3 C2 C1 122.2(4) . . ?
C7 C2 C1 120.4(4) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C11 119.8(4) . . ?
C11 C16 H16 120.1 . . ?
C19 C18 C17 120.4(4) . . ?
C23 C18 C19 118.2(4) . . ?
C23 C18 C17 121.4(4) . . ?
C31 C30 N6 119.3(3) . . ?
C29 C30 C31 122.6(4) . . ?
C29 C30 N6 118.1(4) . . ?
C32 C27 C26 122.4(3) . . ?
C28 C27 C32 119.4(3) . . ?
C28 C27 C26 118.1(3) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.0(4) . . ?
C6 C7 H7 119.5 . . ?
N5 C24 H24A 109.5 . . ?
N5 C24 H24B 109.5 . . ?
N5 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C29 C28 C27 120.7(4) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C5 N2 119.2(4) . . ?
C6 C5 N2 120.7(4) . . ?
C6 C5 C4 120.1(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C16 C15 H15 120.6 . . ?
C14 C15 C16 118.8(4) . . ?
C14 C15 H15 120.6 . . ?
O2 N3 O3 124.4(4) . . ?
O2 N3 C14 118.4(4) . . ?
O3 N3 C14 117.1(4) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.3(4) . . ?
C14 C13 H13 120.8 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.7(4) . . ?
C21 C20 H20 120.1 . . ?
C22 C21 N5 120.2(3) . . ?
C20 C21 N5 119.1(4) . . ?
C20 C21 C22 120.6(4) . . ?
C16 C11 C10 118.9(3) . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 C16 120.2(4) . . ?
C15 C14 N3 119.4(4) . . ?
C13 C14 C15 123.0(4) . . ?
C13 C14 N3 117.6(4) . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 N6 C30 118.1(3) . . ?
O5 N6 O6 124.3(3) . . ?
O6 N6 C30 117.6(3) . . ?

_olex2_date_sample_data_collection 2011-05-24
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/Hexane'
####################################################################### 
# 
# 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_kk110
_database_code_depnum_ccdc_archive 'CCDC 1586976'
loop_
_audit_author_name
_audit_author_address
'Fabian Mohr'
;University of Wuppertal
Germany
;
_audit_update_record             
;
2020-01-27 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H44 Cl2 N4 O2 Pb Se2'
_chemical_formula_sum            'C32 H44 Cl2 N4 O2 Pb Se2'
_chemical_formula_weight         952.72
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C32H44O2Se2N4Cl2Pb1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, z+1/2'
'x, -y, z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'

_cell_length_a                   17.9384(5)
_cell_length_b                   19.0184(12)
_cell_length_c                   10.4156(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3553.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2158
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.3806
_cell_measurement_theta_min      3.1088
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5214
_diffrn_reflns_point_group_measured_fraction_full 0.826
_diffrn_reflns_point_group_measured_fraction_max 0.659
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         29.446
_diffrn_reflns_theta_min         3.115
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.2705
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -78.00   38.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5412    0.0000  -60.0000 116

#__ type_ start__ end____ width___ exp.time_
  2 omega  -66.00  -33.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5412  110.0000 -109.0000 33
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0123013000
_diffrn_orient_matrix_UB_12      0.0338142000
_diffrn_orient_matrix_UB_13      0.0194590000
_diffrn_orient_matrix_UB_21      0.0362670000
_diffrn_orient_matrix_UB_22      -0.0136905000
_diffrn_orient_matrix_UB_23      0.0110545000
_diffrn_orient_matrix_UB_31      0.0098573000
_diffrn_orient_matrix_UB_32      0.0079368000
_diffrn_orient_matrix_UB_33      -0.0642311000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_full    0.630
_reflns_Friedel_fraction_max     0.443
_reflns_number_gt                2931
_reflns_number_total             3244
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 
;
 Flack x determined using 884 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.069(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0489
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C5(H5), C7(H7)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.5000 0.5000 0.09705(5) 0.01969(7) Uani 1 2 d S T P . .
Se1 Se 0.56747(3) 0.41268(3) 0.28729(5) 0.02008(12) Uani 1 1 d . . . . .
N1 N 0.6547(2) 0.5328(3) 0.3506(7) 0.0212(10) Uani 1 1 d . . . . .
C1 C 0.6550(3) 0.4637(3) 0.3264(6) 0.0176(14) Uani 1 1 d . . . . .
N2 N 0.7183(2) 0.4282(2) 0.3500(5) 0.0184(9) Uani 1 1 d . . . . .
O1 O 0.3929(2) 0.42987(19) 0.1564(3) 0.0199(9) Uani 1 1 d . . . . .
C2 C 0.3776(3) 0.4210(3) 0.2734(6) 0.0188(12) Uani 1 1 d . . . . .
C3 C 0.3968(3) 0.3508(3) 0.3331(6) 0.0181(11) Uani 1 1 d . . . . .
C9 C 0.7230(3) 0.3511(3) 0.3426(6) 0.0215(11) Uani 1 1 d . . . . .
H9A H 0.7756 0.3376 0.3281 0.026 Uiso 1 1 calc R . . . .
H9B H 0.6939 0.3349 0.2675 0.026 Uiso 1 1 calc R . . . .
C4 C 0.4259(3) 0.2986(3) 0.2557(5) 0.0212(13) Uani 1 1 d . . . . .
H4 H 0.4299 0.3060 0.1658 0.025 Uiso 1 1 calc R . . . .
C8 C 0.3915(3) 0.3400(3) 0.4638(5) 0.0204(12) Uani 1 1 d . . . . .
H8 H 0.3712 0.3757 0.5172 0.024 Uiso 1 1 calc R . . . .
C13 C 0.7859(3) 0.4679(3) 0.3838(5) 0.0224(13) Uani 1 1 d . . . . .
H13A H 0.8205 0.4364 0.4302 0.027 Uiso 1 1 calc R . . . .
H13B H 0.7721 0.5066 0.4427 0.027 Uiso 1 1 calc R . . . .
C6 C 0.4441(3) 0.2263(3) 0.4386(5) 0.0201(13) Uani 1 1 d . . . . .
C5 C 0.4495(3) 0.2355(3) 0.3081(5) 0.0230(14) Uani 1 1 d . . . . .
H5 H 0.4690 0.1993 0.2550 0.028 Uiso 1 1 calc R . . . .
C11 C 0.7454(3) 0.3257(4) 0.5770(6) 0.0300(14) Uani 1 1 d . . . . .
H11A H 0.7472 0.3760 0.5966 0.045 Uiso 1 1 calc GR . . . .
H11B H 0.7958 0.3088 0.5571 0.045 Uiso 1 1 calc GR . . . .
H11C H 0.7259 0.3000 0.6513 0.045 Uiso 1 1 calc GR . . . .
C10 C 0.6947(3) 0.3134(3) 0.4614(5) 0.0222(13) Uani 1 1 d . . . . .
H10 H 0.6443 0.3326 0.4826 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4156(3) 0.2776(4) 0.5175(6) 0.0219(14) Uani 1 1 d . . . . .
H7 H 0.4124 0.2702 0.6076 0.026 Uiso 1 1 calc R . . . .
C12 C 0.6863(4) 0.2355(4) 0.4326(7) 0.0409(18) Uani 1 1 d . . . . .
H12A H 0.7348 0.2158 0.4087 0.061 Uiso 1 1 calc GR . . . .
H12B H 0.6511 0.2291 0.3615 0.061 Uiso 1 1 calc GR . . . .
H12C H 0.6674 0.2112 0.5090 0.061 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.47398(10) 0.14701(9) 0.50561(17) 0.0328(4) Uani 1 1 d . . . . .
C14 C 0.8263(4) 0.4990(3) 0.2669(6) 0.0276(14) Uani 1 1 d . . . . .
H14 H 0.7897 0.5276 0.2167 0.033 Uiso 1 1 calc R . . . .
C15 C 0.8570(4) 0.4422(4) 0.1801(6) 0.0372(17) Uani 1 1 d . . . . .
H15A H 0.8161 0.4126 0.1494 0.056 Uiso 1 1 calc GR . . . .
H15B H 0.8927 0.4134 0.2280 0.056 Uiso 1 1 calc GR . . . .
H15C H 0.8822 0.4640 0.1066 0.056 Uiso 1 1 calc GR . . . .
C16 C 0.8880(4) 0.5473(4) 0.3130(6) 0.043(2) Uani 1 1 d . . . . .
H16A H 0.9237 0.5203 0.3645 0.065 Uiso 1 1 calc GR . . . .
H16B H 0.8666 0.5850 0.3655 0.065 Uiso 1 1 calc GR . . . .
H16C H 0.9137 0.5677 0.2388 0.065 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pb1 Se1 2.8546(7) 2_665 ?
Pb1 Se1 2.8546(7) . ?
Pb1 O1 2.418(4) . ?
Pb1 O1 2.419(4) 2_665 ?
Se1 C1 1.889(6) . ?
N1 C1 1.339(6) . ?
N1 C2 1.323(8) 2_665 ?
C1 N2 1.344(7) . ?
N2 C9 1.471(6) . ?
N2 C13 1.470(7) . ?
O1 C2 1.260(7) . ?
C2 N1 1.323(8) 2_665 ?
C2 C3 1.513(7) . ?
C3 C4 1.382(7) . ?
C3 C8 1.381(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.517(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(8) . ?
C8 H8 0.9500 . ?
C8 C7 1.381(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.535(8) . ?
C6 C5 1.374(8) . ?
C6 C7 1.375(8) . ?
C6 Cl1 1.745(6) . ?
C5 H5 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C10 1.527(8) . ?
C10 H10 1.0000 . ?
C10 C12 1.520(9) . ?
C7 H7 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.512(9) . ?
C14 C16 1.517(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Se1 Pb1 Se1 92.08(3) 2_665 . ?
O1 Pb1 Se1 80.70(9) . . ?
O1 Pb1 Se1 78.86(9) . 2_665 ?
O1 Pb1 Se1 80.70(9) 2_665 2_665 ?
O1 Pb1 Se1 78.86(9) 2_665 . ?
O1 Pb1 O1 150.38(17) . 2_665 ?
C1 Se1 Pb1 101.7(2) . . ?
C2 N1 C1 122.6(5) 2_665 . ?
N1 C1 Se1 122.8(5) . . ?
N1 C1 N2 117.5(6) . . ?
N2 C1 Se1 119.0(4) . . ?
C1 N2 C9 122.6(5) . . ?
C1 N2 C13 118.9(5) . . ?
C13 N2 C9 118.5(4) . . ?
C2 O1 Pb1 119.6(3) . . ?
N1 C2 C3 115.8(5) 2_665 . ?
O1 C2 N1 126.5(5) . 2_665 ?
O1 C2 C3 117.7(5) . . ?
C4 C3 C2 118.8(5) . . ?
C8 C3 C2 121.4(5) . . ?
C8 C3 C4 119.6(5) . . ?
N2 C9 H9A 108.7 . . ?
N2 C9 H9B 108.7 . . ?
N2 C9 C10 114.1(5) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C8 H8 119.8 . . ?
C3 C8 C7 120.4(5) . . ?
C7 C8 H8 119.8 . . ?
N2 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
N2 C13 C14 113.4(5) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C5 C6 C7 121.8(5) . . ?
C5 C6 Cl1 118.9(5) . . ?
C7 C6 Cl1 119.2(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(5) . . ?
C6 C5 H5 120.7 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
C9 C10 C11 111.8(5) . . ?
C9 C10 H10 108.1 . . ?
C9 C10 C12 109.4(5) . . ?
C11 C10 H10 108.1 . . ?
C12 C10 C11 111.3(5) . . ?
C12 C10 H10 108.1 . . ?
C8 C7 H7 120.5 . . ?
C6 C7 C8 119.0(5) . . ?
C6 C7 H7 120.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C14 H14 108.3 . . ?
C15 C14 C13 111.8(5) . . ?
C15 C14 H14 108.3 . . ?
C15 C14 C16 110.8(6) . . ?
C16 C14 C13 109.1(5) . . ?
C16 C14 H14 108.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_date_sample_data_collection 2011-10-17
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/Hexanes'
