#------------------------------------------------------------------------------
#$Date: 2021-04-05 16:50:07 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263614 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/01/1560130.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_1560130
loop_
_publ_author_name
'Hua, Jiawei'
'Bian, Mixue'
'Ma, Tao'
'Yang, Man'
'He, Wei'
'Yang, Zhao'
'Liu, ChengKou'
'Fang, Zheng'
'Guo, Kai'
_publ_section_title
;
 The sunlight-promoted aerobic selective cyclization of olefinic amides
 and diselenides
;
_journal_issue                   6
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              2299
_journal_page_last               2305
_journal_paper_doi               10.1039/D0CY02273J
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C22 H19 N O3 S Se'
_chemical_formula_sum            'C22 H19 N O3 S Se'
_chemical_formula_weight         456.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-16 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.402(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8297(4)
_cell_length_b                   16.2078(10)
_cell_length_c                   20.9813(13)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.935
_cell_measurement_theta_min      4.375
_cell_volume                     1979.0(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.01
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21746
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.911
_diffrn_reflns_theta_min         2.999
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.526
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1347 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.7913. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.595
_refine_diff_density_min         -2.001
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0625
_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)+(0.0714P)²+6.8320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3507
_reflns_number_total             3717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cy02273j2.cif
_cod_data_source_block           2009141304_0m
_cod_depositor_comments
'Adding full bibliography for 1560129--1560130.cif.'
_cod_database_code               1560130
_shelx_shelxl_version_number     2016/6
_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   0.863
_shelx_estimated_absorpt_t_min   0.823
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 0.64057(11) 0.76046(4) 0.17528(2) 0.0588(2) Uani 1 1 d . . . . .
S1 S 0.72068(15) 0.72155(5) 0.36637(4) 0.0272(2) Uani 1 1 d . . . . .
O1 O 0.9255(5) 0.56125(19) 0.32226(14) 0.0411(7) Uani 1 1 d . . . . .
O2 O 0.9638(5) 0.73217(18) 0.36314(13) 0.0357(6) Uani 1 1 d . . . . .
O3 O 0.5718(5) 0.79143(16) 0.36052(13) 0.0336(6) Uani 1 1 d . . . . .
N1 N 0.6331(5) 0.65870(19) 0.30737(14) 0.0277(7) Uani 1 1 d . . . . .
C1 C 0.7461(7) 0.5834(2) 0.29570(17) 0.0309(8) Uani 1 1 d . . . . .
C2 C 0.5942(7) 0.5398(2) 0.24836(18) 0.0326(8) Uani 1 1 d . . . . .
C3 C 0.6249(9) 0.4626(3) 0.2213(2) 0.0454(11) Uani 1 1 d . . . . .
H3 H 0.762296 0.432078 0.230006 0.054 Uiso 1 1 calc R . . . .
C4 C 0.4480(10) 0.4318(3) 0.1812(2) 0.0525(13) Uani 1 1 d . . . . .
H4 H 0.463483 0.379086 0.162097 0.063 Uiso 1 1 calc R . . . .
C5 C 0.2488(10) 0.4770(3) 0.1686(2) 0.0515(12) Uani 1 1 d . . . . .
H5 H 0.130051 0.454715 0.140783 0.062 Uiso 1 1 calc R . . . .
C6 C 0.2186(8) 0.5541(3) 0.1957(2) 0.0413(10) Uani 1 1 d . . . . .
H6 H 0.081032 0.584630 0.187136 0.050 Uiso 1 1 calc R . . . .
C7 C 0.3960(7) 0.5852(2) 0.23585(17) 0.0311(8) Uani 1 1 d . . . . .
C8 C 0.4048(6) 0.6651(2) 0.27241(17) 0.0300(8) Uani 1 1 d . . . . .
H8 H 0.281104 0.665984 0.303447 0.036 Uiso 1 1 calc R . . . .
C9 C 0.3842(8) 0.7416(3) 0.2292(2) 0.0416(10) Uani 1 1 d . . . . .
H9A H 0.367207 0.790778 0.256464 0.050 Uiso 1 1 calc R . . . .
H9B H 0.241775 0.736487 0.201310 0.050 Uiso 1 1 calc R . . . .
C10 C 0.5569(8) 0.6950(3) 0.1026(2) 0.0445(10) Uani 1 1 d . . . . .
C11 C 0.3469(9) 0.6994(3) 0.0704(2) 0.0467(11) Uani 1 1 d . . . . .
H11 H 0.231265 0.734140 0.085875 0.056 Uiso 1 1 calc R . . . .
C12 C 0.3008(12) 0.6537(3) 0.0154(2) 0.0599(14) Uani 1 1 d . . . . .
H12 H 0.151802 0.656793 -0.005404 0.072 Uiso 1 1 calc R . . . .
C13 C 0.4584(15) 0.6055(4) -0.0094(3) 0.0783(19) Uani 1 1 d . . . . .
H13 H 0.422345 0.574763 -0.047210 0.094 Uiso 1 1 calc R . . . .
C14 C 0.6682(15) 0.6012(5) 0.0201(4) 0.091(2) Uani 1 1 d . . . . .
H14 H 0.781929 0.568167 0.001891 0.109 Uiso 1 1 calc R . . . .
C15 C 0.7253(11) 0.6439(4) 0.0768(3) 0.0750(18) Uani 1 1 d . . . . .
H15 H 0.873834 0.638591 0.097635 0.090 Uiso 1 1 calc R . . . .
C16 C 0.6676(6) 0.6686(2) 0.43688(16) 0.0259(7) Uani 1 1 d . . . . .
C17 C 0.8398(6) 0.6192(2) 0.46560(18) 0.0301(8) Uani 1 1 d . . . . .
H17 H 0.981139 0.611557 0.446040 0.036 Uiso 1 1 calc R . . . .
C18 C 0.8013(7) 0.5815(2) 0.52304(18) 0.0315(8) Uani 1 1 d . . . . .
H18 H 0.918453 0.548100 0.543158 0.038 Uiso 1 1 calc R . . . .
C19 C 0.5941(7) 0.5913(2) 0.55208(17) 0.0308(8) Uani 1 1 d . . . . .
C20 C 0.4249(6) 0.6403(3) 0.52207(18) 0.0318(8) Uani 1 1 d . . . . .
H20 H 0.283173 0.647490 0.541516 0.038 Uiso 1 1 calc R . . . .
C21 C 0.4579(6) 0.6790(2) 0.46433(17) 0.0289(8) Uani 1 1 d . . . . .
H21 H 0.339981 0.711762 0.443985 0.035 Uiso 1 1 calc R . . . .
C22 C 0.5580(8) 0.5508(3) 0.6151(2) 0.0424(10) Uani 1 1 d . . . . .
H22A H 0.562893 0.490712 0.610066 0.064 Uiso 1 1 calc GR . . . .
H22B H 0.408126 0.567064 0.629792 0.064 Uiso 1 1 calc GR . . . .
H22C H 0.679532 0.568148 0.646528 0.064 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -1.0986 0.9246 '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
C10 Se1 C9 102.05(19) . . ?
O2 S1 N1 107.44(17) . . ?
O2 S1 C16 108.85(17) . . ?
O3 S1 O2 119.89(17) . . ?
O3 S1 N1 105.31(16) . . ?
O3 S1 C16 108.90(17) . . ?
N1 S1 C16 105.49(16) . . ?
C1 N1 S1 122.2(3) . . ?
C1 N1 C8 112.8(3) . . ?
C8 N1 S1 123.5(2) . . ?
O1 C1 N1 125.1(4) . . ?
O1 C1 C2 129.5(4) . . ?
N1 C1 C2 105.3(3) . . ?
C3 C2 C1 128.4(4) . . ?
C7 C2 C1 109.6(3) . . ?
C7 C2 C3 121.9(4) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.6(5) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(5) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.8(5) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C6 120.4(4) . . ?
C2 C7 C8 111.0(3) . . ?
C6 C7 C8 128.5(4) . . ?
N1 C8 C7 101.2(3) . . ?
N1 C8 H8 109.8 . . ?
N1 C8 C9 112.6(3) . . ?
C7 C8 H8 109.8 . . ?
C7 C8 C9 113.2(3) . . ?
C9 C8 H8 109.8 . . ?
Se1 C9 H9A 108.4 . . ?
Se1 C9 H9B 108.4 . . ?
C8 C9 Se1 115.6(3) . . ?
C8 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C11 C10 Se1 123.3(4) . . ?
C11 C10 C15 117.6(5) . . ?
C15 C10 Se1 118.9(4) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 118.9 . . ?
C13 C12 C11 122.3(6) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(6) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.1(7) . . ?
C15 C14 H14 118.9 . . ?
C10 C15 H15 120.7 . . ?
C14 C15 C10 118.6(6) . . ?
C14 C15 H15 120.7 . . ?
C17 C16 S1 119.2(3) . . ?
C21 C16 S1 119.6(3) . . ?
C21 C16 C17 121.2(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(4) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C22 120.3(4) . . ?
C20 C19 C18 118.6(3) . . ?
C20 C19 C22 121.1(4) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.7 . . ?
C20 C21 C16 118.5(3) . . ?
C20 C21 H21 120.7 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C9 1.951(5) . ?
Se1 C10 1.897(5) . ?
S1 O2 1.433(3) . ?
S1 O3 1.428(3) . ?
S1 N1 1.660(3) . ?
S1 C16 1.754(4) . ?
O1 C1 1.210(5) . ?
N1 C1 1.415(5) . ?
N1 C8 1.485(5) . ?
C1 C2 1.472(6) . ?
C2 C3 1.389(6) . ?
C2 C7 1.382(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(6) . ?
C7 C8 1.505(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.536(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.365(6) . ?
C10 C15 1.417(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.335(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.339(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(5) . ?
C16 C21 1.392(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(6) . ?
C19 C20 1.388(6) . ?
C19 C22 1.502(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
