#------------------------------------------------------------------------------
#$Date: 2022-09-24 01:58:21 +0300 (Sat, 24 Sep 2022) $
#$Revision: 278140 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/13/7711332.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7711332
loop_
_publ_author_name
'Sanjay Kumar, Siddharth'
'Rangarajan, Shalini'
'Kunchur, Harish S.'
'Balakrishna, Maravanji Shivaramaiah'
_publ_section_title
;
 A greener approach towards the synthesis of N-heterocyclic thiones and
 selones using mechanochemical technique
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02322A
_journal_year                    2022
_chemical_formula_moiety         'C17 H17 N2 O P Se'
_chemical_formula_sum            'C17 H17 N2 O P Se'
_chemical_formula_weight         375.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-12 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9392(3)
_cell_length_b                   8.0482(3)
_cell_length_c                   37.8833(12)
_cell_measurement_reflns_used    8045
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      24.3330
_cell_measurement_theta_min      2.1390
_cell_volume                     3335.28(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     67.17 201.67   0.50    2.00  13.96 -12.24 -31.50    --   269
  2  φ   -121.38  29.12   0.50    2.00  78.62 -12.24  31.50    --   301
  3  ω   -110.52  18.48   0.50    2.00    --  -12.24 -59.25  20.08  258
  4  ω   -110.52  18.48   0.50    2.00    --  -12.24 -59.25  71.08  258
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            55566
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.660
_diffrn_reflns_theta_min         2.150
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         5557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0528
_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)+(0.0564P)²+1.2104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3181
_reflns_number_total             5557
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02322a2.cif
_cod_data_source_block           comp_4
_cod_database_code               7711332
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.796
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C12(H12), C3(H3), C6(H6), C15(H15), C13(H13), C14(H14),
 C9(H9), C8(H8), C7(H7), C2(H2)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.44329(3) 0.17993(5) 0.45092(2) 0.06098(15) Uani 1 1 d . . . . .
P1 P 0.60376(6) 0.37252(8) 0.34353(2) 0.03228(16) Uani 1 1 d . . . . .
O1 O 0.72616(16) 0.4212(2) 0.33052(5) 0.0439(4) Uani 1 1 d . . . . .
N2 N 0.6589(2) 0.2685(3) 0.41183(5) 0.0378(5) Uani 1 1 d . . . . .
N1 N 0.6775(2) 0.3153(3) 0.46768(6) 0.0518(6) Uani 1 1 d . . . . .
C5 C 0.5125(2) 0.2644(3) 0.31091(6) 0.0334(5) Uani 1 1 d . . . . .
C11 C 0.5146(2) 0.5466(3) 0.35803(6) 0.0342(5) Uani 1 1 d . . . . .
C1 C 0.5980(3) 0.2594(4) 0.44312(7) 0.0413(6) Uani 1 1 d . . . . .
C4 C 0.6086(2) 0.2151(3) 0.37841(6) 0.0361(5) Uani 1 1 d . . . . .
H4A H 0.524277 0.174744 0.382525 0.043 Uiso 1 1 calc R U . . .
H4B H 0.657312 0.119736 0.369792 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3859(3) 0.2694(3) 0.31093(7) 0.0430(6) Uani 1 1 d . . . . .
H10 H 0.344036 0.335692 0.327810 0.052 Uiso 1 1 calc R U . . .
C16 C 0.5281(3) 0.6930(3) 0.33892(7) 0.0411(6) Uani 1 1 d . . . . .
H16 H 0.584533 0.697442 0.319890 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4320(2) 0.5417(4) 0.38607(7) 0.0445(6) Uani 1 1 d . . . . .
H12 H 0.421554 0.442467 0.399318 0.053 Uiso 1 1 calc R U . . .
C3 C 0.7767(3) 0.3266(4) 0.41749(8) 0.0470(7) Uani 1 1 d . . . . .
H3 H 0.838148 0.342432 0.400089 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5734(3) 0.1657(4) 0.28629(7) 0.0448(7) Uani 1 1 d . . . . .
H6 H 0.660178 0.161105 0.286146 0.054 Uiso 1 1 calc R U . . .
C15 C 0.4602(3) 0.8316(4) 0.34735(9) 0.0528(8) Uani 1 1 d . . . . .
H15 H 0.469342 0.930903 0.334046 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3653(3) 0.6829(4) 0.39446(9) 0.0569(8) Uani 1 1 d . . . . .
H13 H 0.309827 0.680250 0.413739 0.068 Uiso 1 1 calc R U . . .
C14 C 0.3784(3) 0.8260(4) 0.37532(9) 0.0548(8) Uani 1 1 d . . . . .
H14 H 0.331545 0.921399 0.381184 0.066 Uiso 1 1 calc R U . . .
C9 C 0.3197(3) 0.1778(4) 0.28632(8) 0.0539(8) Uani 1 1 d . . . . .
H9 H 0.232915 0.182127 0.286228 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3807(3) 0.0806(4) 0.26209(8) 0.0551(8) Uani 1 1 d . . . . .
H8 H 0.335877 0.017484 0.245314 0.066 Uiso 1 1 calc R U . . .
C7 C 0.5068(3) 0.0748(4) 0.26214(7) 0.0540(8) Uani 1 1 d . . . . .
H7 H 0.548165 0.007491 0.245365 0.065 Uiso 1 1 calc R U . . .
C2 C 0.7873(3) 0.3562(4) 0.45208(8) 0.0557(8) Uani 1 1 d . . . . .
H2 H 0.857767 0.397755 0.463787 0.067 Uiso 1 1 calc R U . . .
C17 C 0.6493(3) 0.3298(5) 0.50545(8) 0.0766(12) Uani 1 1 d . . . . .
H17A H 0.596926 0.426933 0.509347 0.115 Uiso 1 1 calc R U . . .
H17B H 0.725375 0.342858 0.518820 0.115 Uiso 1 1 calc R U . . .
H17C H 0.606695 0.229446 0.513384 0.115 Uiso 1 1 calc R U . . .
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'
P P 0.1023 0.0942 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C5 113.51(11) . . ?
O1 P1 C11 112.79(11) . . ?
O1 P1 C4 113.43(12) . . ?
C5 P1 C4 100.12(11) . . ?
C11 P1 C5 106.52(12) . . ?
C11 P1 C4 109.57(12) . . ?
C1 N2 C4 124.1(2) . . ?
C1 N2 C3 109.7(2) . . ?
C3 N2 C4 126.1(2) . . ?
C1 N1 C2 110.2(2) . . ?
C1 N1 C17 124.2(3) . . ?
C2 N1 C17 125.6(3) . . ?
C10 C5 P1 122.46(19) . . ?
C10 C5 C6 119.6(2) . . ?
C6 C5 P1 117.8(2) . . ?
C16 C11 P1 116.4(2) . . ?
C16 C11 C12 119.3(2) . . ?
C12 C11 P1 124.3(2) . . ?
N2 C1 Se1 127.6(2) . . ?
N1 C1 Se1 126.9(2) . . ?
N1 C1 N2 105.5(2) . . ?
P1 C4 H4A 108.3 . . ?
P1 C4 H4B 108.3 . . ?
N2 C4 P1 115.92(17) . . ?
N2 C4 H4A 108.3 . . ?
N2 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C5 C10 H10 119.9 . . ?
C5 C10 C9 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
N2 C3 H3 126.5 . . ?
C2 C3 N2 107.0(3) . . ?
C2 C3 H3 126.5 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.9(3) . . ?
C14 C15 H15 120.1 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.1(3) . . ?
C7 C8 H8 119.9 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N1 C2 H2 126.2 . . ?
C3 C2 N1 107.6(3) . . ?
C3 C2 H2 126.2 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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 1.833(3) . ?
P1 O1 1.4796(18) . ?
P1 C5 1.811(3) . ?
P1 C11 1.793(3) . ?
P1 C4 1.831(2) . ?
N2 C1 1.362(3) . ?
N2 C4 1.446(3) . ?
N2 C3 1.388(4) . ?
N1 C1 1.351(4) . ?
N1 C2 1.378(4) . ?
N1 C17 1.468(4) . ?
C5 C10 1.386(4) . ?
C5 C6 1.395(4) . ?
C11 C16 1.391(4) . ?
C11 C12 1.395(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C9 1.392(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.378(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.337(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(4) . ?
C14 H14 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.378(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.380(5) . ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
P1 C5 C10 C9 -176.9(2) . . . . ?
P1 C5 C6 C7 176.8(2) . . . . ?
P1 C11 C16 C15 177.8(2) . . . . ?
P1 C11 C12 C13 -178.3(2) . . . . ?
O1 P1 C5 C10 -152.0(2) . . . . ?
O1 P1 C5 C6 31.7(2) . . . . ?
O1 P1 C11 C16 36.2(2) . . . . ?
O1 P1 C11 C12 -145.6(2) . . . . ?
O1 P1 C4 N2 68.3(2) . . . . ?
N2 C3 C2 N1 0.5(4) . . . . ?
C5 P1 C11 C16 -88.9(2) . . . . ?
C5 P1 C11 C12 89.2(2) . . . . ?
C5 P1 C4 N2 -170.45(19) . . . . ?
C5 C10 C9 C8 0.6(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C11 P1 C5 C10 -27.2(2) . . . . ?
C11 P1 C5 C6 156.4(2) . . . . ?
C11 P1 C4 N2 -58.7(2) . . . . ?
C11 C16 C15 C14 0.6(4) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C1 N2 C4 P1 123.1(2) . . . . ?
C1 N2 C3 C2 -1.2(3) . . . . ?
C1 N1 C2 C3 0.3(4) . . . . ?
C4 P1 C5 C10 86.8(2) . . . . ?
C4 P1 C5 C6 -89.5(2) . . . . ?
C4 P1 C11 C16 163.6(2) . . . . ?
C4 P1 C11 C12 -18.3(3) . . . . ?
C4 N2 C1 Se1 0.2(4) . . . . ?
C4 N2 C1 N1 177.9(2) . . . . ?
C4 N2 C3 C2 -177.6(3) . . . . ?
C10 C5 C6 C7 0.3(4) . . . . ?
C10 C9 C8 C7 -0.3(5) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C16 C15 C14 C13 0.0(5) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C3 N2 C1 Se1 -176.3(2) . . . . ?
C3 N2 C1 N1 1.4(3) . . . . ?
C3 N2 C4 P1 -61.0(3) . . . . ?
C6 C5 C10 C9 -0.6(4) . . . . ?
C9 C8 C7 C6 0.0(5) . . . . ?
C2 N1 C1 Se1 176.6(2) . . . . ?
C2 N1 C1 N2 -1.0(3) . . . . ?
C17 N1 C1 Se1 -3.4(5) . . . . ?
C17 N1 C1 N2 178.9(3) . . . . ?
C17 N1 C2 C3 -179.6(3) . . . . ?
