#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:20:44 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257606 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240415.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_7240415
loop_
_publ_author_name
'Charpe, Vaibhav Pramod'
'Sagadevan, Arunachalam'
'Hwang, Kuo Chu'
_publ_section_title
;
 Visible light-induced aerobic oxidation of diarylalkynes to α-diketones
 catalyzed by copper-superoxo at room temperature
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              4426
_journal_page_last               4432
_journal_paper_doi               10.1039/D0GC00975J
_journal_volume                  22
_journal_year                    2020
_chemical_formula_sum            'C23 H22 N2 O2 S'
_chemical_formula_weight         390.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-07-30 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                95.845(2)
_cell_angle_beta                 105.956(2)
_cell_angle_gamma                109.513(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3322(5)
_cell_length_b                   10.0321(5)
_cell_length_c                   11.8425(6)
_cell_measurement_reflns_used    7970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.2355
_cell_measurement_theta_min      2.2047
_cell_volume                     981.56(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28567
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.568
_diffrn_reflns_theta_min         1.831
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0397
_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)+(0.0319P)²+1.0128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3282
_reflns_number_total             4075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc00975j2.cif
_cod_data_source_block           mo_180117lt_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7240411--7240415.cif.

 Adding full bibliography for 7240411--7240415.cif.
;
_cod_database_code               7240415
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.6025(2) 0.3360(2) 0.45780(18) 0.0143(4) Uani 1 1 d . . . . .
C2 C 0.5438(2) 0.3444(2) 0.62634(18) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.6819(2) 0.4607(2) 0.63993(18) 0.0145(4) Uani 1 1 d . . . . .
C4 C 0.6005(2) 0.2873(2) 0.33675(18) 0.0148(4) Uani 1 1 d . . . . .
C5 C 0.7365(2) 0.3546(2) 0.30338(19) 0.0159(4) Uani 1 1 d . . . . .
C6 C 0.7364(3) 0.3106(2) 0.18780(19) 0.0187(5) Uani 1 1 d . . . . .
H6 H 0.8286 0.3556 0.1656 0.022 Uiso 1 1 calc R U . . .
C7 C 0.6025(3) 0.2017(2) 0.1056(2) 0.0210(5) Uani 1 1 d . . . . .
H7 H 0.6026 0.1730 0.0267 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4676(3) 0.1336(2) 0.1373(2) 0.0213(5) Uani 1 1 d . . . . .
H8 H 0.3758 0.0586 0.0804 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4676(3) 0.1755(2) 0.25209(19) 0.0177(4) Uani 1 1 d . . . . .
H9 H 0.3758 0.1277 0.2739 0.021 Uiso 1 1 calc R U . . .
C10 C 0.4551(2) 0.2980(2) 0.70953(18) 0.0146(4) Uani 1 1 d . . . . .
C11 C 0.3951(2) 0.1519(2) 0.71527(18) 0.0167(4) Uani 1 1 d . . . . .
H11 H 0.4120 0.0826 0.6651 0.020 Uiso 1 1 calc R U . . .
C12 C 0.3112(3) 0.1074(2) 0.79355(19) 0.0202(5) Uani 1 1 d . . . . .
H12 H 0.2703 0.0080 0.7965 0.024 Uiso 1 1 calc R U . . .
C13 C 0.2870(3) 0.2085(2) 0.86763(19) 0.0205(5) Uani 1 1 d . . . . .
H13 H 0.2289 0.1781 0.9209 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3477(3) 0.3535(2) 0.8637(2) 0.0208(5) Uani 1 1 d . . . . .
H14 H 0.3326 0.4226 0.9155 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4303(2) 0.3986(2) 0.78493(19) 0.0175(4) Uani 1 1 d . . . . .
H15 H 0.4703 0.4981 0.7821 0.021 Uiso 1 1 calc R U . . .
C16 C 0.7889(2) 0.5766(2) 0.74634(18) 0.0149(4) Uani 1 1 d . . . . .
C17 C 0.8278(2) 0.5469(2) 0.86142(18) 0.0174(4) Uani 1 1 d . . . . .
H17 H 0.7846 0.4506 0.8718 0.021 Uiso 1 1 calc R U . . .
C18 C 0.9293(3) 0.6577(2) 0.9604(2) 0.0223(5) Uani 1 1 d . . . . .
H18 H 0.9558 0.6366 1.0381 0.027 Uiso 1 1 calc R U . . .
C19 C 0.9924(3) 0.7988(2) 0.9467(2) 0.0237(5) Uani 1 1 d . . . . .
H19 H 1.0611 0.8743 1.0148 0.028 Uiso 1 1 calc R U . . .
C20 C 0.9545(3) 0.8289(2) 0.8331(2) 0.0223(5) Uani 1 1 d . . . . .
H20 H 0.9968 0.9257 0.8234 0.027 Uiso 1 1 calc R U . . .
C21 C 0.8554(2) 0.7188(2) 0.7336(2) 0.0186(4) Uani 1 1 d . . . . .
H21 H 0.8324 0.7403 0.6558 0.022 Uiso 1 1 calc R U . . .
C22 C 0.1042(3) 0.7558(2) 0.2964(2) 0.0227(5) Uani 1 1 d . . . . .
H22A H 0.0089 0.7700 0.2481 0.034 Uiso 1 1 calc R U . . .
H22B H 0.0726 0.6571 0.3106 0.034 Uiso 1 1 calc R U . . .
H22C H 0.1822 0.7704 0.2533 0.034 Uiso 1 1 calc R U . . .
C23 C 0.0259(3) 0.8251(2) 0.4897(2) 0.0261(5) Uani 1 1 d . . . . .
H23A H 0.0467 0.8944 0.5625 0.039 Uiso 1 1 calc R U . . .
H23B H 0.0103 0.7293 0.5081 0.039 Uiso 1 1 calc R U . . .
H23C H -0.0712 0.8202 0.4276 0.039 Uiso 1 1 calc R U . . .
N1 N 0.4950(2) 0.26670(18) 0.51035(15) 0.0143(4) Uani 1 1 d . . . . .
H1 H 0.4094 0.1865 0.4765 0.017 Uiso 1 1 calc R U . . .
N2 N 0.7170(2) 0.45391(18) 0.53394(15) 0.0150(4) Uani 1 1 d . . . . .
O1 O 0.87052(17) 0.46245(16) 0.38039(13) 0.0204(3) Uani 1 1 d . . . . .
H1A H 0.8557 0.4819 0.4459 0.031 Uiso 1 1 calc R U . . .
O2 O 0.20573(18) 1.02761(15) 0.40539(13) 0.0197(3) Uani 1 1 d . . . . .
S1 S 0.19305(6) 0.88248(6) 0.43666(5) 0.01679(14) Uani 1 1 d . . . . .
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'
S S 0.1246 0.1234 '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
N2 C1 N1 110.60(18) . . ?
N2 C1 C4 123.34(18) . . ?
N1 C1 C4 126.00(18) . . ?
C3 C2 N1 105.95(17) . . ?
C3 C2 C10 131.95(19) . . ?
N1 C2 C10 122.10(17) . . ?
C2 C3 N2 109.12(18) . . ?
C2 C3 C16 129.79(19) . . ?
N2 C3 C16 121.04(18) . . ?
C9 C4 C5 118.53(19) . . ?
C9 C4 C1 122.30(19) . . ?
C5 C4 C1 119.17(18) . . ?
O1 C5 C6 117.77(19) . . ?
O1 C5 C4 122.18(18) . . ?
C6 C5 C4 120.05(19) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C15 C10 C11 118.87(19) . . ?
C15 C10 C2 120.82(18) . . ?
C11 C10 C2 120.30(18) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C21 C16 C17 118.66(19) . . ?
C21 C16 C3 120.13(19) . . ?
C17 C16 C3 121.21(19) . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.5(2) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C2 107.80(16) . . ?
C1 N1 H1 126.1 . . ?
C2 N1 H1 126.1 . . ?
C1 N2 C3 106.53(17) . . ?
C5 O1 H1A 109.5 . . ?
O2 S1 C23 106.55(10) . . ?
O2 S1 C22 105.34(10) . . ?
C23 S1 C22 97.70(11) . . ?
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
C1 N2 1.328(3) . ?
C1 N1 1.357(3) . ?
C1 C4 1.460(3) . ?
C2 C3 1.376(3) . ?
C2 N1 1.379(3) . ?
C2 C10 1.468(3) . ?
C3 N2 1.382(3) . ?
C3 C16 1.473(3) . ?
C4 C9 1.400(3) . ?
C4 C5 1.408(3) . ?
C5 O1 1.354(2) . ?
C5 C6 1.394(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.398(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.395(3) . ?
C16 C17 1.400(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 S1 1.780(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 S1 1.780(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1 H1 0.8800 . ?
O1 H1A 0.8400 . ?
O2 S1 1.5132(15) . ?
