# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_8952
_database_code_depnum_ccdc_archive 'CCDC 2151760'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2022-02-13 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N2 O P Se'
_chemical_formula_sum            'C18 H23 N2 O P Se'
_chemical_formula_weight         393.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8367(3)
_cell_length_b                   28.7426(13)
_cell_length_c                   9.8648(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.255(5)
_cell_angle_gamma                90
_cell_volume                     1830.04(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1548
_cell_measurement_theta_min      3.0860
_cell_measurement_theta_max      68.7450

_exptl_crystal_description       block
_exptl_crystal_colour            colrless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    3.642
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3911
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         70.109
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.784
_diffrn_measured_fraction_theta_full 0.803
_diffrn_reflns_Laue_measured_fraction_max 0.784
_diffrn_reflns_Laue_measured_fraction_full 0.803
_diffrn_reflns_point_group_measured_fraction_max 0.784
_diffrn_reflns_point_group_measured_fraction_full 0.803
_reflns_number_total             2720
_reflns_number_gt                2343
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    WinGx
_computing_publication_material  'ORTEP 3'
_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)+(0.0346P)²+2.7709P] 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         2720
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_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
Se1 Se 0.71855(8) 0.10674(2) 0.79105(7) 0.0626(2) Uani 1 1 d . . . . .
P1 P 0.43949(16) 0.12510(4) 0.82336(12) 0.0373(3) Uani 1 1 d . . . . .
O1 O -0.1242(7) -0.08770(13) 0.5441(4) 0.0758(12) Uani 1 1 d . . . . .
N1 N 0.2637(5) 0.08332(11) 0.8005(4) 0.0388(8) Uani 1 1 d . . . . .
H1 H 0.139179 0.086856 0.742793 0.047 Uiso 1 1 calc R U . . .
N2 N 0.0564(5) -0.01190(11) 0.7308(4) 0.0386(8) Uani 1 1 d . . . . .
C1 C 0.4816(7) 0.14448(14) 1.0056(5) 0.0411(10) Uani 1 1 d . . . . .
C2 C 0.3299(8) 0.13949(16) 1.0683(5) 0.0512(12) Uani 1 1 d . . . . .
H2 H 0.203094 0.126246 1.016541 0.061 Uiso 1 1 calc R U . . .
C3 C 0.3660(10) 0.15426(19) 1.2090(6) 0.0668(15) Uani 1 1 d . . . . .
H3 H 0.264373 0.150808 1.251812 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5550(11) 0.1741(2) 1.2842(6) 0.0774(19) Uani 1 1 d . . . . .
H4 H 0.580364 0.183968 1.378253 0.093 Uiso 1 1 calc R U . . .
C5 C 0.7031(11) 0.1794(2) 1.2227(6) 0.0760(18) Uani 1 1 d . . . . .
H5 H 0.828655 0.193137 1.274416 0.091 Uiso 1 1 calc R U . . .
C6 C 0.6707(8) 0.16452(17) 1.0840(5) 0.0574(13) Uani 1 1 d . . . . .
H6 H 0.774403 0.167884 1.042991 0.069 Uiso 1 1 calc R U . . .
C7 C 0.2985(7) 0.17131(14) 0.7063(4) 0.0385(10) Uani 1 1 d . . . . .
C8 C 0.1029(7) 0.18392(16) 0.7063(5) 0.0505(12) Uani 1 1 d . . . . .
H8 H 0.042121 0.168282 0.764703 0.061 Uiso 1 1 calc R U . . .
C9 C -0.0013(8) 0.21974(17) 0.6192(6) 0.0583(13) Uani 1 1 d . . . . .
H9 H -0.132279 0.228301 0.619747 0.070 Uiso 1 1 calc R U . . .
C10 C 0.0858(9) 0.24277(17) 0.5323(6) 0.0612(15) Uani 1 1 d . . . . .
H10 H 0.013869 0.266744 0.473501 0.073 Uiso 1 1 calc R U . . .
C11 C 0.2780(10) 0.23063(19) 0.5316(6) 0.0727(17) Uani 1 1 d . . . . .
H11 H 0.337297 0.246418 0.472652 0.087 Uiso 1 1 calc R U . . .
C12 C 0.3852(9) 0.19489(18) 0.6185(6) 0.0609(14) Uani 1 1 d . . . . .
H12 H 0.516402 0.186721 0.617623 0.073 Uiso 1 1 calc R U . . .
C13 C 0.3288(7) 0.04024(14) 0.8822(5) 0.0438(11) Uani 1 1 d . . . . .
H13A H 0.400981 0.047852 0.982068 0.053 Uiso 1 1 calc R U . . .
H13B H 0.424806 0.023744 0.845729 0.053 Uiso 1 1 calc R U . . .
C14 C 0.1477(7) 0.00900(14) 0.8729(5) 0.0413(10) Uani 1 1 d . . . . .
H14A H 0.193389 -0.015558 0.943804 0.050 Uiso 1 1 calc R U . . .
H14B H 0.042470 0.026925 0.895773 0.050 Uiso 1 1 calc R U . . .
C15 C -0.1523(8) -0.02858(18) 0.7125(6) 0.0584(13) Uani 1 1 d . . . . .
H15A H -0.237956 -0.002836 0.722902 0.070 Uiso 1 1 calc R U . . .
H15B H -0.146996 -0.051404 0.786093 0.070 Uiso 1 1 calc R U . . .
C16 C -0.2462(9) -0.0504(2) 0.5655(6) 0.0720(16) Uani 1 1 d . . . . .
H16A H -0.384076 -0.061681 0.555095 0.086 Uiso 1 1 calc R U . . .
H16B H -0.259085 -0.026891 0.492400 0.086 Uiso 1 1 calc R U . . .
C17 C 0.0805(9) -0.07225(19) 0.5642(6) 0.0672(16) Uani 1 1 d . . . . .
H17A H 0.077432 -0.049494 0.490925 0.081 Uiso 1 1 calc R U . . .
H17B H 0.163562 -0.098400 0.553038 0.081 Uiso 1 1 calc R U . . .
C18 C 0.1802(8) -0.05076(16) 0.7106(5) 0.0535(12) Uani 1 1 d . . . . .
H18A H 0.192488 -0.073974 0.784314 0.064 Uiso 1 1 calc R U . . .
H18B H 0.318349 -0.039985 0.719437 0.064 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 P1 2.1026(13) . ?
P1 N1 1.661(3) . ?
P1 C1 1.812(5) . ?
P1 C7 1.815(4) . ?
O1 C16 1.417(7) . ?
O1 C17 1.418(7) . ?
N1 C13 1.465(5) . ?
N1 H1 0.8600 . ?
N2 C18 1.454(6) . ?
N2 C15 1.459(6) . ?
N2 C14 1.462(5) . ?
C1 C2 1.379(6) . ?
C1 C6 1.393(6) . ?
C2 C3 1.393(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.350(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.378(6) . ?
C7 C8 1.385(6) . ?
C8 C9 1.379(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.508(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.515(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.511(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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 P1 C1 103.2(2) . . ?
N1 P1 C7 103.54(18) . . ?
C1 P1 C7 106.47(19) . . ?
N1 P1 Se1 116.74(13) . . ?
C1 P1 Se1 111.86(15) . . ?
C7 P1 Se1 113.92(16) . . ?
C16 O1 C17 110.1(4) . . ?
C13 N1 P1 117.5(3) . . ?
C13 N1 H1 121.3 . . ?
P1 N1 H1 121.3 . . ?
C18 N2 C15 108.7(4) . . ?
C18 N2 C14 111.3(3) . . ?
C15 N2 C14 110.1(4) . . ?
C2 C1 C6 119.4(4) . . ?
C2 C1 P1 121.1(3) . . ?
C6 C1 P1 119.5(4) . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.2(6) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.6(6) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 119.1(4) . . ?
C12 C7 P1 120.8(4) . . ?
C8 C7 P1 120.1(3) . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.3(5) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N1 C13 C14 112.1(3) . . ?
N1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N2 C14 C13 112.7(4) . . ?
N2 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
N2 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N2 C15 C16 110.0(4) . . ?
N2 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O1 C16 C15 111.8(4) . . ?
O1 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
O1 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
O1 C17 C18 112.0(5) . . ?
O1 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
O1 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
N2 C18 C17 110.2(4) . . ?
N2 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N2 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 P1 N1 C13 -68.8(3) . . . . ?
C7 P1 N1 C13 -179.7(3) . . . . ?
Se1 P1 N1 C13 54.3(3) . . . . ?
N1 P1 C1 C2 -26.0(4) . . . . ?
C7 P1 C1 C2 82.6(4) . . . . ?
Se1 P1 C1 C2 -152.3(3) . . . . ?
N1 P1 C1 C6 153.6(4) . . . . ?
C7 P1 C1 C6 -97.7(4) . . . . ?
Se1 P1 C1 C6 27.3(4) . . . . ?
C6 C1 C2 C3 -0.2(7) . . . . ?
P1 C1 C2 C3 179.4(4) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C3 C4 C5 C6 -0.8(10) . . . . ?
C4 C5 C6 C1 0.9(9) . . . . ?
C2 C1 C6 C5 -0.4(7) . . . . ?
P1 C1 C6 C5 179.9(4) . . . . ?
N1 P1 C7 C12 -135.1(4) . . . . ?
C1 P1 C7 C12 116.4(4) . . . . ?
Se1 P1 C7 C12 -7.3(4) . . . . ?
N1 P1 C7 C8 46.1(4) . . . . ?
C1 P1 C7 C8 -62.4(4) . . . . ?
Se1 P1 C7 C8 173.9(3) . . . . ?
C12 C7 C8 C9 -0.2(7) . . . . ?
P1 C7 C8 C9 178.6(4) . . . . ?
C7 C8 C9 C10 0.4(8) . . . . ?
C8 C9 C10 C11 -0.4(8) . . . . ?
C9 C10 C11 C12 0.2(9) . . . . ?
C8 C7 C12 C11 0.0(8) . . . . ?
P1 C7 C12 C11 -178.8(4) . . . . ?
C10 C11 C12 C7 0.0(9) . . . . ?
P1 N1 C13 C14 169.5(3) . . . . ?
C18 N2 C14 C13 78.1(4) . . . . ?
C15 N2 C14 C13 -161.3(4) . . . . ?
N1 C13 C14 N2 70.8(5) . . . . ?
C18 N2 C15 C16 -57.6(5) . . . . ?
C14 N2 C15 C16 -179.8(4) . . . . ?
C17 O1 C16 C15 -56.7(6) . . . . ?
N2 C15 C16 O1 58.2(6) . . . . ?
C16 O1 C17 C18 56.6(6) . . . . ?
C15 N2 C18 C17 57.5(5) . . . . ?
C14 N2 C18 C17 178.9(4) . . . . ?
O1 C17 C18 N2 -57.9(6) . . . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2209322'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2022-09-25 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N2 O'
_chemical_formula_sum            'C22 H22 N2 O'
_chemical_formula_weight         330.41

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.242(12)
_cell_length_b                   15.493(18)
_cell_length_c                   11.726(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1861(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4117
_cell_measurement_theta_min      2.178
_cell_measurement_theta_max      27.160

_exptl_crystal_description       block
_exptl_crystal_colour            ;colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9865
_diffrn_reflns_av_unetI/netI     0.6040
_diffrn_reflns_av_R_equivalents  0.5948
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         27.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.872
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_point_group_measured_fraction_full 0.835
_reflns_number_total             3330
_reflns_number_gt                682
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.755
_reflns_Friedel_fraction_full    0.794

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    WinGx
_computing_publication_material  'ORTEP 3'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3330
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.4657
_refine_ls_R_factor_gt           0.1139
_refine_ls_wR_factor_ref         0.3236
_refine_ls_wR_factor_gt          0.1944
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_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
N1 N 0.4274(16) 0.7774(10) 0.4488(16) 0.067(5) Uani 1 1 d . . . . .
H1 H 0.350647 0.772209 0.477823 0.080 Uiso 1 1 calc R U . . .
O1 O 0.6428(15) 0.7369(8) 0.4760(17) 0.095(6) Uani 1 1 d . . . . .
N2 N 0.4849(15) 0.6770(10) 0.5833(17) 0.062(5) Uani 1 1 d . . . . .
C10 C 0.5652(19) 0.5304(14) 0.643(3) 0.068(8) Uani 1 1 d . . . . .
C20 C 0.256(3) 0.796(2) 0.936(3) 0.134(13) Uani 1 1 d . . . . .
H20 H 0.234918 0.822520 1.004827 0.161 Uiso 1 1 calc R U . . .
C21 C 0.198(3) 0.721(2) 0.902(3) 0.121(12) Uani 1 1 d . . . . .
H21 H 0.128752 0.700222 0.945444 0.145 Uiso 1 1 calc R U . . .
C22 C 0.232(3) 0.6750(16) 0.810(3) 0.123(12) Uani 1 1 d . . . . .
H22 H 0.197778 0.620275 0.798217 0.147 Uiso 1 1 calc R U . . .
C17 C 0.323(2) 0.7107(16) 0.731(3) 0.091(9) Uani 1 1 d . . . . .
C16 C 0.353(2) 0.6606(12) 0.6248(18) 0.068(7) Uani 1 1 d . . . . .
H16A H 0.343115 0.599405 0.640389 0.082 Uiso 1 1 calc R U . . .
H16B H 0.290596 0.675972 0.565887 0.082 Uiso 1 1 calc R U . . .
C8 C 0.530(3) 0.7301(13) 0.498(2) 0.067(7) Uani 1 1 d . . . . .
C1 C 0.444(2) 0.8343(13) 0.353(2) 0.065(7) Uani 1 1 d . . . . .
C2 C 0.564(2) 0.8585(14) 0.306(3) 0.094(8) Uani 1 1 d . . . . .
H2 H 0.641090 0.836700 0.336879 0.112 Uiso 1 1 calc R U . . .
C3 C 0.568(3) 0.9131(15) 0.218(2) 0.096(10) Uani 1 1 d . . . . .
H3 H 0.648333 0.925009 0.184602 0.115 Uiso 1 1 calc R U . . .
C4 C 0.464(3) 0.9503(13) 0.177(3) 0.081(9) Uani 1 1 d . . . . .
C5 C 0.472(2) 1.0094(14) 0.068(2) 0.120(10) Uani 1 1 d . . . . .
H5A H 0.556851 1.004491 0.034068 0.180 Uiso 1 1 calc R U . . .
H5B H 0.456307 1.068381 0.089166 0.180 Uiso 1 1 calc R U . . .
H5C H 0.406840 0.991451 0.013829 0.180 Uiso 1 1 calc R U . . .
C9 C 0.589(2) 0.6318(11) 0.653(2) 0.092(8) Uani 1 1 d . . . . .
H9A H 0.583903 0.649806 0.732400 0.110 Uiso 1 1 calc R U . . .
H9B H 0.675317 0.646364 0.624594 0.110 Uiso 1 1 calc R U . . .
C11 C 0.571(2) 0.4892(15) 0.545(3) 0.089(8) Uani 1 1 d . . . . .
H11 H 0.585233 0.517894 0.476236 0.107 Uiso 1 1 calc R U . . .
C12 C 0.555(2) 0.3956(18) 0.551(3) 0.116(11) Uani 1 1 d . . . . .
H12 H 0.547030 0.362521 0.484784 0.140 Uiso 1 1 calc R U . . .
C13 C 0.553(3) 0.359(2) 0.656(4) 0.121(12) Uani 1 1 d . . . . .
H13 H 0.555114 0.298876 0.657880 0.145 Uiso 1 1 calc R U . . .
C14 C 0.547(4) 0.399(2) 0.754(4) 0.18(2) Uani 1 1 d . . . . .
H14 H 0.532194 0.370215 0.822904 0.211 Uiso 1 1 calc R U . . .
C15 C 0.566(2) 0.4894(18) 0.746(3) 0.104(9) Uani 1 1 d . . . . .
H15 H 0.578782 0.521384 0.811873 0.124 Uiso 1 1 calc R U . . .
C19 C 0.346(3) 0.831(2) 0.864(4) 0.139(14) Uani 1 1 d . . . . .
H19 H 0.384636 0.883669 0.883182 0.167 Uiso 1 1 calc R U . . .
C18 C 0.382(2) 0.7892(18) 0.760(3) 0.095(8) Uani 1 1 d . . . . .
H18 H 0.443763 0.813840 0.712567 0.114 Uiso 1 1 calc R U . . .
C7 C 0.332(2) 0.8723(14) 0.303(2) 0.078(7) Uani 1 1 d . . . . .
H7 H 0.249623 0.859255 0.330059 0.093 Uiso 1 1 calc R U . . .
C6 C 0.346(3) 0.9264(14) 0.217(2) 0.092(8) Uani 1 1 d . . . . .
H6 H 0.271666 0.948843 0.182011 0.110 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
N1 C8 1.40(2) . ?
N1 C1 1.44(3) . ?
N1 H1 0.8600 . ?
O1 C8 1.19(2) . ?
N2 C8 1.38(2) . ?
N2 C16 1.46(2) . ?
N2 C9 1.52(2) . ?
C10 C11 1.32(3) . ?
C10 C15 1.36(4) . ?
C10 C9 1.59(3) . ?
C20 C19 1.36(4) . ?
C20 C21 1.37(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.34(4) . ?
C21 H21 0.9300 . ?
C22 C17 1.42(3) . ?
C22 H22 0.9300 . ?
C17 C18 1.40(3) . ?
C17 C16 1.50(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C7 1.41(3) . ?
C1 C2 1.40(3) . ?
C2 C3 1.34(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.30(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.35(3) . ?
C4 C5 1.58(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.46(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.36(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.31(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.42(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C19 C18 1.43(4) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C7 C6 1.32(3) . ?
C7 H7 0.9300 . ?
C6 H6 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
C8 N1 C1 123.4(18) . . ?
C8 N1 H1 118.3 . . ?
C1 N1 H1 118.3 . . ?
C8 N2 C16 131.1(18) . . ?
C8 N2 C9 115.7(18) . . ?
C16 N2 C9 113.0(19) . . ?
C11 C10 C15 123(3) . . ?
C11 C10 C9 122(2) . . ?
C15 C10 C9 113(3) . . ?
C19 C20 C21 117(3) . . ?
C19 C20 H20 121.5 . . ?
C21 C20 H20 121.5 . . ?
C22 C21 C20 125(3) . . ?
C22 C21 H21 117.6 . . ?
C20 C21 H21 117.6 . . ?
C21 C22 C17 119(3) . . ?
C21 C22 H22 120.3 . . ?
C17 C22 H22 120.3 . . ?
C18 C17 C22 117(3) . . ?
C18 C17 C16 124(3) . . ?
C22 C17 C16 118(3) . . ?
N2 C16 C17 112.2(19) . . ?
N2 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
O1 C8 N2 122(2) . . ?
O1 C8 N1 127(2) . . ?
N2 C8 N1 111(2) . . ?
C7 C1 C2 116(2) . . ?
C7 C1 N1 119(2) . . ?
C2 C1 N1 125(3) . . ?
C3 C2 C1 120(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 123(3) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C6 119(3) . . ?
C3 C4 C5 121(3) . . ?
C6 C4 C5 119(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 . . ?
N2 C9 C10 107.8(17) . . ?
N2 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
N2 C9 H9B 110.1 . . ?
C10 C9 H9B 110.1 . . ?
H9A C9 H9B 108.5 . . ?
C10 C11 C12 116(3) . . ?
C10 C11 H11 122.1 . . ?
C12 C11 H11 122.1 . . ?
C13 C12 C11 117(3) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C14 C13 C12 127(4) . . ?
C14 C13 H13 116.4 . . ?
C12 C13 H13 116.4 . . ?
C13 C14 C15 113(4) . . ?
C13 C14 H14 123.3 . . ?
C15 C14 H14 123.3 . . ?
C14 C15 C10 122(3) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C20 C19 C18 121(3) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C17 C18 C19 120(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C6 C7 C1 120(2) . . ?
C6 C7 H7 120.0 . . ?
C1 C7 H7 120.0 . . ?
C7 C6 C4 122(3) . . ?
C7 C6 H6 118.9 . . ?
C4 C6 H6 118.9 . . ?

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
C19 C20 C21 C22 7(5) . . . . ?
C20 C21 C22 C17 -10(5) . . . . ?
C21 C22 C17 C18 7(4) . . . . ?
C21 C22 C17 C16 -176(3) . . . . ?
C8 N2 C16 C17 -100(3) . . . . ?
C9 N2 C16 C17 76(2) . . . . ?
C18 C17 C16 N2 27(3) . . . . ?
C22 C17 C16 N2 -150(2) . . . . ?
C16 N2 C8 O1 179(2) . . . . ?
C9 N2 C8 O1 4(3) . . . . ?
C16 N2 C8 N1 3(3) . . . . ?
C9 N2 C8 N1 -171.9(17) . . . . ?
C1 N1 C8 O1 9(4) . . . . ?
C1 N1 C8 N2 -176.1(19) . . . . ?
C8 N1 C1 C7 173.6(18) . . . . ?
C8 N1 C1 C2 -9(3) . . . . ?
C7 C1 C2 C3 -1(3) . . . . ?
N1 C1 C2 C3 -179(2) . . . . ?
C1 C2 C3 C4 5(4) . . . . ?
C2 C3 C4 C6 -7(4) . . . . ?
C2 C3 C4 C5 -176(2) . . . . ?
C8 N2 C9 C10 -122(2) . . . . ?
C16 N2 C9 C10 62(3) . . . . ?
C11 C10 C9 N2 62(3) . . . . ?
C15 C10 C9 N2 -131(2) . . . . ?
C15 C10 C11 C12 11(3) . . . . ?
C9 C10 C11 C12 176.3(19) . . . . ?
C10 C11 C12 C13 -8(3) . . . . ?
C11 C12 C13 C14 9(5) . . . . ?
C12 C13 C14 C15 -10(6) . . . . ?
C13 C14 C15 C10 11(5) . . . . ?
C11 C10 C15 C14 -13(4) . . . . ?
C9 C10 C15 C14 -179(2) . . . . ?
C21 C20 C19 C18 -3(5) . . . . ?
C22 C17 C18 C19 -2(3) . . . . ?
C16 C17 C18 C19 -180(2) . . . . ?
C20 C19 C18 C17 0(4) . . . . ?
C2 C1 C7 C6 1(3) . . . . ?
N1 C1 C7 C6 178(2) . . . . ?
C1 C7 C6 C4 -3(4) . . . . ?
C3 C4 C6 C7 6(4) . . . . ?
C5 C4 C6 C7 175(2) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_9399
_database_code_depnum_ccdc_archive 'CCDC 2151762'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2022-02-13 deposited with the CCDC.	2022-12-22 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         'C20 H28 Al N2 O P Se'
_chemical_formula_sum            'C20 H28 Al N2 O P Se'
_chemical_formula_weight         449.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Al Al 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   7.6068(2)
_cell_length_b                   19.9624(7)
_cell_length_c                   14.6284(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.245(3)
_cell_angle_gamma                90
_cell_volume                     2220.80(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4332
_cell_measurement_theta_min      3.7520
_cell_measurement_theta_max      68.9790

_exptl_crystal_description       block
_exptl_crystal_colour            ;colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    3.434
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11354
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.747
_diffrn_reflns_theta_max         69.904
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4169
_reflns_number_gt                3321
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_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)+(0.0430P)²+1.3141P] 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         4169
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
P1 P 0.54469(9) 0.24532(4) 0.66115(5) 0.04185(18) Uani 1 1 d . . . . .
Al1 Al 0.60449(11) 0.38797(4) 0.75784(6) 0.0451(2) Uani 1 1 d . . . . .
C15 C 0.4218(4) 0.18777(14) 0.7317(2) 0.0476(7) Uani 1 1 d . . . . .
C18 C 0.2255(7) 0.1043(2) 0.8403(3) 0.0957(14) Uani 1 1 d . . . . .
H18 H 0.1597 0.0759 0.8766 0.115 Uiso 1 1 calc R U . . .
C9 C 0.3813(4) 0.29685(14) 0.6028(2) 0.0455(7) Uani 1 1 d . . . . .
O1 O 0.7258(3) 0.46386(12) 1.01881(16) 0.0705(7) Uani 1 1 d . . . . .
N1 N 0.6486(3) 0.29763(11) 0.72936(16) 0.0422(5) Uani 1 1 d . . . . .
N2 N 0.7829(3) 0.37765(11) 0.86325(16) 0.0428(5) Uani 1 1 d . . . . .
C16 C 0.3402(5) 0.21181(17) 0.8091(2) 0.0632(9) Uani 1 1 d . . . . .
H16 H 0.3538 0.2566 0.8255 0.076 Uiso 1 1 calc R U . . .
C4 C 0.9009(4) 0.32545(16) 0.8242(2) 0.0541(8) Uani 1 1 d . . . . .
H4A H 0.9801 0.3087 0.8718 0.065 Uiso 1 1 calc R U . . .
H4B H 0.9712 0.3452 0.7767 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7941(4) 0.26833(15) 0.7849(2) 0.0533(8) Uani 1 1 d . . . . .
H3A H 0.8670 0.2402 0.7471 0.064 Uiso 1 1 calc R U . . .
H3B H 0.7477 0.2411 0.8336 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8904(4) 0.43828(16) 0.8850(2) 0.0569(8) Uani 1 1 d . . . . .
H7A H 0.9331 0.4576 0.8288 0.068 Uiso 1 1 calc R U . . .
H7B H 0.9915 0.4256 0.9227 0.068 Uiso 1 1 calc R U . . .
C11 C 0.0829(5) 0.3258(2) 0.5613(3) 0.0760(11) Uani 1 1 d . . . . .
H11 H -0.0370 0.3172 0.5646 0.091 Uiso 1 1 calc R U . . .
C2 C 0.7046(6) 0.45663(18) 0.6783(3) 0.0819(12) Uani 1 1 d . . . . .
H2A H 0.8217 0.4439 0.6624 0.123 Uiso 1 1 calc R U . . .
H2B H 0.7080 0.4988 0.7100 0.123 Uiso 1 1 calc R U . . .
H2C H 0.6330 0.4608 0.6238 0.123 Uiso 1 1 calc R U . . .
C13 C 0.3191(5) 0.3902(2) 0.5040(3) 0.0784(11) Uani 1 1 d . . . . .
H13 H 0.3589 0.4258 0.4691 0.094 Uiso 1 1 calc R U . . .
C10 C 0.2013(4) 0.28513(17) 0.6082(2) 0.0574(8) Uani 1 1 d . . . . .
H10 H 0.1605 0.2499 0.6435 0.069 Uiso 1 1 calc R U . . .
C20 C 0.4042(6) 0.12090(18) 0.7102(3) 0.0782(11) Uani 1 1 d . . . . .
H20 H 0.4573 0.1036 0.6586 0.094 Uiso 1 1 calc R U . . .
C17 C 0.2401(6) 0.1706(2) 0.8617(3) 0.0793(11) Uani 1 1 d . . . . .
H17 H 0.1823 0.1878 0.9120 0.095 Uiso 1 1 calc R U . . .
C6 C 0.6161(5) 0.40735(17) 1.0026(2) 0.0639(9) Uani 1 1 d . . . . .
H6A H 0.5123 0.4213 0.9678 0.077 Uiso 1 1 calc R U . . .
H6B H 0.5780 0.3896 1.0606 0.077 Uiso 1 1 calc R U . . .
C8 C 0.7834(5) 0.48924(17) 0.9345(2) 0.0658(9) Uani 1 1 d . . . . .
H8A H 0.8536 0.5291 0.9453 0.079 Uiso 1 1 calc R U . . .
H8B H 0.6822 0.5017 0.8967 0.079 Uiso 1 1 calc R U . . .
C12 C 0.1397(5) 0.3780(2) 0.5103(3) 0.0871(13) Uani 1 1 d . . . . .
H12 H 0.0591 0.4054 0.4797 0.105 Uiso 1 1 calc R U . . .
C14 C 0.4378(4) 0.34938(17) 0.5498(2) 0.0588(8) Uani 1 1 d . . . . .
H14 H 0.5576 0.3574 0.5448 0.071 Uiso 1 1 calc R U . . .
C5 C 0.7092(4) 0.35298(15) 0.9508(2) 0.0516(7) Uani 1 1 d . . . . .
H5A H 0.8039 0.3351 0.9890 0.062 Uiso 1 1 calc R U . . .
H5B H 0.6272 0.3169 0.9377 0.062 Uiso 1 1 calc R U . . .
C19 C 0.3074(8) 0.0799(2) 0.7655(4) 0.1098(18) Uani 1 1 d . . . . .
H19 H 0.2979 0.0346 0.7516 0.132 Uiso 1 1 calc R U . . .
Se1 Se 0.70185(4) 0.19258(2) 0.56697(2) 0.05697(13) Uani 1 1 d . . . . .
C1 C 0.3649(4) 0.40556(17) 0.7991(3) 0.0679(10) Uani 1 1 d . . . . .
H1A H 0.2849 0.4051 0.7474 0.102 Uiso 1 1 calc R U . . .
H1B H 0.3612 0.4486 0.8283 0.102 Uiso 1 1 calc R U . . .
H1C H 0.3316 0.3716 0.8418 0.102 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
P1 N1 1.636(2) . ?
P1 C9 1.812(3) . ?
P1 C15 1.817(3) . ?
P1 Se1 2.1230(8) . ?
Al1 N1 1.883(2) . ?
Al1 C2 1.962(4) . ?
Al1 C1 1.964(3) . ?
Al1 N2 2.043(2) . ?
C15 C20 1.378(4) . ?
C15 C16 1.388(4) . ?
C18 C19 1.361(6) . ?
C18 C17 1.364(6) . ?
C18 H18 0.9300 . ?
C9 C14 1.378(4) . ?
C9 C10 1.393(4) . ?
O1 C8 1.412(4) . ?
O1 C6 1.420(4) . ?
N1 C3 1.479(3) . ?
N2 C7 1.491(3) . ?
N2 C5 1.493(4) . ?
N2 C4 1.496(4) . ?
C16 C17 1.369(5) . ?
C16 H16 0.9300 . ?
C4 C3 1.507(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C7 C8 1.499(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C11 C12 1.358(6) . ?
C11 C10 1.383(5) . ?
C11 H11 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C13 C14 1.379(5) . ?
C13 C12 1.392(6) . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
C20 C19 1.376(5) . ?
C20 H20 0.9300 . ?
C17 H17 0.9300 . ?
C6 C5 1.509(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C19 H19 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
N1 P1 C9 104.01(12) . . ?
N1 P1 C15 107.74(13) . . ?
C9 P1 C15 105.68(14) . . ?
N1 P1 Se1 116.15(9) . . ?
C9 P1 Se1 111.47(10) . . ?
C15 P1 Se1 111.06(10) . . ?
N1 Al1 C2 117.69(15) . . ?
N1 Al1 C1 114.24(13) . . ?
C2 Al1 C1 115.58(18) . . ?
N1 Al1 N2 87.23(10) . . ?
C2 Al1 N2 104.94(14) . . ?
C1 Al1 N2 113.08(14) . . ?
C20 C15 C16 118.6(3) . . ?
C20 C15 P1 122.1(3) . . ?
C16 C15 P1 119.3(2) . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C14 C9 C10 118.5(3) . . ?
C14 C9 P1 118.6(2) . . ?
C10 C9 P1 122.9(2) . . ?
C8 O1 C6 109.3(2) . . ?
C3 N1 P1 115.37(18) . . ?
C3 N1 Al1 113.09(17) . . ?
P1 N1 Al1 131.31(13) . . ?
C7 N2 C5 107.4(2) . . ?
C7 N2 C4 108.4(2) . . ?
C5 N2 C4 109.7(2) . . ?
C7 N2 Al1 115.56(18) . . ?
C5 N2 Al1 115.15(17) . . ?
C4 N2 Al1 100.17(16) . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
N2 C4 C3 110.5(2) . . ?
N2 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C3 C4 107.5(2) . . ?
N1 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
N1 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N2 C7 C8 110.6(3) . . ?
N2 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
Al1 C2 H2A 109.5 . . ?
Al1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Al1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C19 C20 C15 119.5(4) . . ?
C19 C20 H20 120.2 . . ?
C15 C20 H20 120.2 . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O1 C6 C5 112.0(3) . . ?
O1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
O1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O1 C8 C7 111.1(3) . . ?
O1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
O1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C5 C6 112.5(3) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C18 C19 C20 121.3(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
Al1 C1 H1A 109.5 . . ?
Al1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Al1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
C3 H3A Se1 0.97 3.05 3.584(3) 116.3 .
C20 H20 Se1 0.93 2.92 3.431(4) 116.1 .

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_9646
_database_code_depnum_ccdc_archive 'CCDC 2209321'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2022-09-25 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H37 Al2 N2 O P Se '
_chemical_formula_sum            'C23 H37 Al2 N2 O P Se '
_chemical_formula_weight         521.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Al Al 0.0645 0.0514 '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'
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1432(5)
_cell_length_b                   7.1641(2)
_cell_length_c                   27.1954(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.638(4)
_cell_angle_gamma                90
_cell_volume                     2746.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2556
_cell_measurement_theta_min      2.8880
_cell_measurement_theta_max      24.6020

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.506
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11147
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.890
_diffrn_reflns_theta_max         29.178
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6274
_reflns_number_gt                4036
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_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)+(0.0385P)²+0.3180P] 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         6274
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Al1 Al 0.22286(6) 0.14402(12) 0.54171(3) 0.0442(2) Uani 1 1 d . . . . .
Al2 Al 0.11655(8) 0.33167(16) 0.33932(4) 0.0687(3) Uani 1 1 d . . . . .
Se1 Se 0.48256(2) 0.45350(4) 0.56605(2) 0.05647(13) Uani 1 1 d . . . . .
P1 P 0.40537(5) 0.26185(10) 0.60667(3) 0.03935(19) Uani 1 1 d . . . . .
O1 O 0.19560(14) 0.1759(3) 0.38793(8) 0.0579(6) Uani 1 1 d . . . . .
N1 N 0.34378(15) 0.1044(3) 0.57382(9) 0.0391(6) Uani 1 1 d . . . . .
N2 N 0.27409(16) 0.0197(3) 0.48081(9) 0.0444(6) Uani 1 1 d . . . . .
C1 C 0.4026(2) -0.0245(4) 0.54641(12) 0.0464(7) Uani 1 1 d . . . . .
H1A H 0.432926 -0.115896 0.568768 0.056 Uiso 1 1 calc R U . . .
H1B H 0.451570 0.044826 0.531323 0.056 Uiso 1 1 calc R U . . .
C2 C 0.3383(2) -0.1217(4) 0.50690(12) 0.0513(8) Uani 1 1 d . . . . .
H2A H 0.376260 -0.182637 0.483460 0.062 Uiso 1 1 calc R U . . .
H2B H 0.300739 -0.216184 0.521893 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2042(2) -0.0804(4) 0.44662(13) 0.0567(9) Uani 1 1 d . . . . .
H3A H 0.166273 -0.162938 0.465330 0.068 Uiso 1 1 calc R U . . .
H3B H 0.237561 -0.156039 0.423994 0.068 Uiso 1 1 calc R U . . .
C4 C 0.1410(2) 0.0550(5) 0.41807(13) 0.0609(9) Uani 1 1 d . . . . .
H4A H 0.094140 -0.012830 0.397014 0.073 Uiso 1 1 calc R U . . .
H4B H 0.107590 0.130374 0.440723 0.073 Uiso 1 1 calc R U . . .
C5 C 0.2690(2) 0.2737(5) 0.41864(12) 0.0574(9) Uani 1 1 d . . . . .
H5A H 0.239240 0.361499 0.439750 0.069 Uiso 1 1 calc R U . . .
H5B H 0.308274 0.344134 0.397662 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3301(2) 0.1429(4) 0.44993(12) 0.0526(8) Uani 1 1 d . . . . .
H6A H 0.366231 0.066111 0.428816 0.063 Uiso 1 1 calc R U . . .
H6B H 0.374753 0.214720 0.471266 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1223(2) -0.0226(5) 0.56042(15) 0.0747(11) Uani 1 1 d . . . . .
H7A H 0.147266 -0.146294 0.565487 0.112 Uiso 1 1 calc R U . . .
H7B H 0.071779 -0.024796 0.534610 0.112 Uiso 1 1 calc R U . . .
H7C H 0.098338 0.021534 0.590357 0.112 Uiso 1 1 calc R U . . .
C8 C 0.1842(3) 0.4027(4) 0.53050(14) 0.0692(10) Uani 1 1 d . . . . .
H8A H 0.165725 0.455566 0.560707 0.104 Uiso 1 1 calc R U . . .
H8B H 0.131642 0.407362 0.505892 0.104 Uiso 1 1 calc R U . . .
H8C H 0.236322 0.472707 0.519365 0.104 Uiso 1 1 calc R U . . .
C9 C 0.4841(2) 0.1365(4) 0.65137(11) 0.0439(7) Uani 1 1 d . . . . .
C10 C 0.4520(3) -0.0188(5) 0.67401(16) 0.0807(13) Uani 1 1 d . . . . .
H10 H 0.390014 -0.058679 0.666325 0.097 Uiso 1 1 calc R U . . .
C11 C 0.5104(3) -0.1187(6) 0.70838(17) 0.0992(15) Uani 1 1 d . . . . .
H11 H 0.487271 -0.222972 0.723875 0.119 Uiso 1 1 calc R U . . .
C12 C 0.6015(3) -0.0622(6) 0.71903(16) 0.0879(13) Uani 1 1 d . . . . .
H12 H 0.641278 -0.127733 0.741806 0.105 Uiso 1 1 calc R U . . .
C13 C 0.6335(3) 0.0887(7) 0.69648(18) 0.1076(17) Uani 1 1 d . . . . .
H13 H 0.695993 0.126516 0.703697 0.129 Uiso 1 1 calc R U . . .
C14 C 0.5758(2) 0.1889(6) 0.66281(15) 0.0772(12) Uani 1 1 d . . . . .
H14 H 0.599730 0.293415 0.647759 0.093 Uiso 1 1 calc R U . . .
C15 C 0.31578(19) 0.3692(4) 0.64111(11) 0.0417(7) Uani 1 1 d . . . . .
C16 C 0.2483(2) 0.2632(5) 0.66177(11) 0.0525(8) Uani 1 1 d . . . . .
H16 H 0.249487 0.134001 0.658481 0.063 Uiso 1 1 calc R U . . .
C17 C 0.1787(2) 0.3452(5) 0.68732(13) 0.0635(9) Uani 1 1 d . . . . .
H17 H 0.132844 0.271621 0.700550 0.076 Uiso 1 1 calc R U . . .
C18 C 0.1773(3) 0.5343(6) 0.69310(14) 0.0699(11) Uani 1 1 d . . . . .
H18 H 0.131231 0.589759 0.710822 0.084 Uiso 1 1 calc R U . . .
C19 C 0.2435(3) 0.6416(5) 0.67282(15) 0.0767(12) Uani 1 1 d . . . . .
H19 H 0.242014 0.770601 0.676377 0.092 Uiso 1 1 calc R U . . .
C20 C 0.3127(2) 0.5603(5) 0.64712(14) 0.0625(9) Uani 1 1 d . . . . .
H20 H 0.357747 0.635023 0.633660 0.075 Uiso 1 1 calc R U . . .
C21 C 0.2115(3) 0.4609(6) 0.30319(18) 0.1073(16) Uani 1 1 d . . . . .
H21A H 0.256434 0.372007 0.292648 0.161 Uiso 1 1 calc R U . . .
H21B H 0.243888 0.551782 0.324336 0.161 Uiso 1 1 calc R U . . .
H21C H 0.180665 0.522331 0.274893 0.161 Uiso 1 1 calc R U . . .
C22 C 0.0405(2) 0.1373(5) 0.30451(13) 0.0761(11) Uani 1 1 d . . . . .
H22A H 0.013307 0.185524 0.273590 0.114 Uiso 1 1 calc R U . . .
H22B H -0.009341 0.098870 0.324252 0.114 Uiso 1 1 calc R U . . .
H22C H 0.080108 0.032225 0.298605 0.114 Uiso 1 1 calc R U . . .
C23 C 0.0519(3) 0.4963(6) 0.38395(18) 0.1094(17) Uani 1 1 d . . . . .
H23A H 0.024030 0.599644 0.365599 0.164 Uiso 1 1 calc R U . . .
H23B H 0.097097 0.541929 0.409381 0.164 Uiso 1 1 calc R U . . .
H23C H 0.003226 0.427480 0.398631 0.164 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
Al1 N1 1.878(2) . ?
Al1 C8 1.949(3) . ?
Al1 C7 1.956(3) . ?
Al1 N2 2.063(3) . ?
Al2 C22 1.956(4) . ?
Al2 C21 1.959(5) . ?
Al2 C23 1.969(4) . ?
Al2 O1 2.001(2) . ?
Se1 P1 2.1195(8) . ?
P1 N1 1.644(2) . ?
P1 C15 1.807(3) . ?
P1 C9 1.818(3) . ?
O1 C4 1.457(4) . ?
O1 C5 1.458(3) . ?
N1 C1 1.483(3) . ?
N2 C3 1.485(4) . ?
N2 C6 1.490(4) . ?
N2 C2 1.500(4) . ?
C1 C2 1.520(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.494(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.494(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
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 C14 1.362(4) . ?
C9 C10 1.367(4) . ?
C10 C11 1.394(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.339(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.375(4) . ?
C15 C20 1.380(4) . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
N1 Al1 C8 116.72(14) . . ?
N1 Al1 C7 116.17(14) . . ?
C8 Al1 C7 114.86(17) . . ?
N1 Al1 N2 86.68(10) . . ?
C8 Al1 N2 113.40(14) . . ?
C7 Al1 N2 104.80(14) . . ?
C22 Al2 C21 117.78(19) . . ?
C22 Al2 C23 117.38(18) . . ?
C21 Al2 C23 113.4(2) . . ?
C22 Al2 O1 100.30(14) . . ?
C21 Al2 O1 103.06(15) . . ?
C23 Al2 O1 100.89(16) . . ?
N1 P1 C15 102.17(12) . . ?
N1 P1 C9 107.05(13) . . ?
C15 P1 C9 106.30(14) . . ?
N1 P1 Se1 115.72(9) . . ?
C15 P1 Se1 114.00(10) . . ?
C9 P1 Se1 110.80(10) . . ?
C4 O1 C5 110.4(2) . . ?
C4 O1 Al2 114.20(17) . . ?
C5 O1 Al2 116.39(18) . . ?
C1 N1 P1 113.97(17) . . ?
C1 N1 Al1 112.76(18) . . ?
P1 N1 Al1 124.84(13) . . ?
C3 N2 C6 106.9(2) . . ?
C3 N2 C2 108.4(2) . . ?
C6 N2 C2 109.7(2) . . ?
C3 N2 Al1 116.88(19) . . ?
C6 N2 Al1 115.72(18) . . ?
C2 N2 Al1 98.65(18) . . ?
N1 C1 C2 108.2(2) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 109.2(2) . . ?
N2 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C4 110.6(3) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
O1 C4 C3 110.8(2) . . ?
O1 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
O1 C5 C6 112.2(3) . . ?
O1 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
O1 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 C6 C5 112.5(2) . . ?
N2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
Al1 C7 H7A 109.5 . . ?
Al1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Al1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Al1 C8 H8A 109.5 . . ?
Al1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Al1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 117.8(3) . . ?
C14 C9 P1 122.5(3) . . ?
C10 C9 P1 119.7(2) . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.4(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C9 C14 C13 120.6(4) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C20 118.0(3) . . ?
C16 C15 P1 121.0(2) . . ?
C20 C15 P1 120.9(2) . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
Al2 C21 H21A 109.5 . . ?
Al2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Al2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Al2 C22 H22A 109.5 . . ?
Al2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Al2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Al2 C23 H23A 109.5 . . ?
Al2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Al2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C15 P1 N1 C1 -172.1(2) . . . . ?
C9 P1 N1 C1 -60.6(2) . . . . ?
Se1 P1 N1 C1 63.4(2) . . . . ?
C15 P1 N1 Al1 42.23(19) . . . . ?
C9 P1 N1 Al1 153.73(16) . . . . ?
Se1 P1 N1 Al1 -82.22(15) . . . . ?
C8 Al1 N1 C1 -127.4(2) . . . . ?
C7 Al1 N1 C1 92.0(2) . . . . ?
N2 Al1 N1 C1 -12.83(19) . . . . ?
C8 Al1 N1 P1 18.6(2) . . . . ?
C7 Al1 N1 P1 -121.96(19) . . . . ?
N2 Al1 N1 P1 133.16(16) . . . . ?
P1 N1 C1 C2 -163.5(2) . . . . ?
Al1 N1 C1 C2 -13.7(3) . . . . ?
C3 N2 C2 C1 -173.3(2) . . . . ?
C6 N2 C2 C1 70.3(3) . . . . ?
Al1 N2 C2 C1 -51.1(2) . . . . ?
N1 C1 C2 N2 45.5(3) . . . . ?
C6 N2 C3 C4 -59.4(3) . . . . ?
C2 N2 C3 C4 -177.6(3) . . . . ?
Al1 N2 C3 C4 72.1(3) . . . . ?
C5 O1 C4 C3 -56.9(3) . . . . ?
Al2 O1 C4 C3 169.7(2) . . . . ?
N2 C3 C4 O1 61.6(3) . . . . ?
C4 O1 C5 C6 53.5(3) . . . . ?
Al2 O1 C5 C6 -174.2(2) . . . . ?
C3 N2 C6 C5 56.3(3) . . . . ?
C2 N2 C6 C5 173.7(3) . . . . ?
Al1 N2 C6 C5 -75.8(3) . . . . ?
O1 C5 C6 N2 -54.8(4) . . . . ?
N1 P1 C9 C14 139.0(3) . . . . ?
C15 P1 C9 C14 -112.4(3) . . . . ?
Se1 P1 C9 C14 12.0(3) . . . . ?
N1 P1 C9 C10 -39.6(3) . . . . ?
C15 P1 C9 C10 69.0(3) . . . . ?
Se1 P1 C9 C10 -166.6(3) . . . . ?
C14 C9 C10 C11 1.2(6) . . . . ?
P1 C9 C10 C11 179.9(3) . . . . ?
C9 C10 C11 C12 -1.0(7) . . . . ?
C10 C11 C12 C13 0.2(8) . . . . ?
C11 C12 C13 C14 0.4(8) . . . . ?
C10 C9 C14 C13 -0.6(6) . . . . ?
P1 C9 C14 C13 -179.2(3) . . . . ?
C12 C13 C14 C9 -0.2(7) . . . . ?
N1 P1 C15 C16 42.2(3) . . . . ?
C9 P1 C15 C16 -69.9(3) . . . . ?
Se1 P1 C15 C16 167.8(2) . . . . ?
N1 P1 C15 C20 -137.3(3) . . . . ?
C9 P1 C15 C20 110.7(3) . . . . ?
Se1 P1 C15 C20 -11.7(3) . . . . ?
C20 C15 C16 C17 0.7(5) . . . . ?
P1 C15 C16 C17 -178.8(2) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C16 C17 C18 C19 1.2(6) . . . . ?
C17 C18 C19 C20 -0.9(6) . . . . ?
C18 C19 C20 C15 0.5(6) . . . . ?
C16 C15 C20 C19 -0.4(5) . . . . ?
P1 C15 C20 C19 179.1(3) . . . . ?

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
C20 H20 Se1 0.93 2.95 3.475(3) 117.1 .
C1 H1A Se1 0.97 3.17 3.931(3) 137.0 1_545
C1 H1B Se1 0.97 3.10 3.632(3) 116.3 .
C2 H2A Se1 0.97 3.16 4.101(3) 163.4 3_656
C14 H14 Se1 0.93 2.90 3.420(4) 116.8 .
C1 H1A Se1 0.97 3.17 3.931(3) 137.0 1_545
C1 H1B Se1 0.97 3.10 3.632(3) 116.3 .
C2 H2A Se1 0.97 3.16 4.101(3) 163.4 3_656
C14 H14 Se1 0.93 2.90 3.420(4) 116.8 .
C20 H20 Se1 0.93 2.95 3.475(3) 117.1 .

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.056

