#------------------------------------------------------------------------------
#$Date: 2021-05-05 12:02:33 +0300 (Wed, 05 May 2021) $
#$Revision: 264941 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157988.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_7157988
loop_
_publ_author_name
'Liu, Xue'
'Wang, Jingjing'
'Wu, Ziyan'
'Li, Feng'
'Gao, Kexin'
'Peng, Fanyang'
'Wang, Junjie'
'Shen, Renzeng'
'Zhou, Yao'
'Liu, Lantao'
_publ_section_title
;
 An organophotoredox-catalyzed C(sp²)-N cross coupling reaction
 of cyclic aldimines with cyclic aliphatic amines.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3595
_journal_page_last               3600
_journal_paper_doi               10.1039/d1ob00223f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C11 H12 N2 O4 S'
_chemical_formula_weight         268.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-10-24 deposited with the CCDC.	2021-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                95.122(5)
_cell_angle_beta                 107.332(5)
_cell_angle_gamma                113.574(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4413(11)
_cell_length_b                   8.9170(13)
_cell_length_c                   9.0986(11)
_cell_measurement_reflns_used    5799
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.83
_cell_volume                     581.96(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10933
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.1831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                2239
_reflns_number_total             2643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob00223f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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

 Adding full bibliography for 7157988.cif.
;
_cod_original_cell_volume        581.95(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7157988
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.85809(5) 0.35714(5) 0.70064(4) 0.03336(12) Uani 1 1 d . . .
N1 N 0.55503(17) 0.25786(14) 0.27213(13) 0.0316(3) Uani 1 1 d . . .
O1 O 0.98975(14) 0.54182(13) 0.68742(13) 0.0367(3) Uani 1 1 d . . .
O2 O 0.98231(17) 0.28683(16) 0.75602(15) 0.0499(3) Uani 1 1 d . . .
N2 N 0.72491(17) 0.25936(15) 0.52075(14) 0.0329(3) Uani 1 1 d . . .
O3 O 0.75710(16) 0.37742(16) 0.79484(13) 0.0461(3) Uani 1 1 d . . .
C1 C 0.3779(3) 0.2553(2) 0.00573(19) 0.0497(4) Uani 1 1 d . . .
H4 H 0.3012 0.2927 0.0443 0.060 Uiso 1 1 calc R . .
H5 H 0.3870 0.2975 -0.0876 0.060 Uiso 1 1 calc R . .
O4 O 0.29445(18) 0.07618(15) -0.03506(13) 0.0507(3) Uani 1 1 d . . .
C2 C 0.5686(2) 0.32428(19) 0.13175(17) 0.0378(3) Uani 1 1 d . . .
H14 H 0.6474 0.2920 0.0914 0.045 Uiso 1 1 calc R . .
H13 H 0.6237 0.4463 0.1605 0.045 Uiso 1 1 calc R . .
C3 C 0.67209(18) 0.34402(16) 0.42105(15) 0.0265(3) Uani 1 1 d . . .
C4 C 0.73282(18) 0.52647(16) 0.46974(16) 0.0264(3) Uani 1 1 d . . .
C5 C 0.89233(19) 0.62139(17) 0.60317(16) 0.0295(3) Uani 1 1 d . . .
C6 C 0.9605(2) 0.79277(19) 0.65599(19) 0.0391(4) Uani 1 1 d . . .
H12 H 1.0702 0.8537 0.7432 0.047 Uiso 1 1 calc R . .
C7 C 0.8630(2) 0.87229(19) 0.5771(2) 0.0433(4) Uani 1 1 d . . .
H2 H 0.9087 0.9883 0.6097 0.052 Uiso 1 1 calc R . .
C8 C 0.4633(2) 0.07303(18) 0.23230(18) 0.0392(4) Uani 1 1 d . . .
H9 H 0.4460 0.0325 0.3245 0.047 Uiso 1 1 calc R . .
H6 H 0.5394 0.0304 0.1989 0.047 Uiso 1 1 calc R . .
C9 C 0.2770(2) 0.0117(2) 0.09974(19) 0.0460(4) Uani 1 1 d . . .
H7 H 0.2177 -0.1104 0.0691 0.055 Uiso 1 1 calc R . .
H8 H 0.1980 0.0462 0.1378 0.055 Uiso 1 1 calc R . .
C10 C 0.6321(2) 0.60905(18) 0.39648(18) 0.0328(3) Uani 1 1 d . . .
H10 H 0.5204 0.5479 0.3114 0.039 Uiso 1 1 calc R . .
C11 C 0.6970(2) 0.7802(2) 0.4492(2) 0.0406(4) Uani 1 1 d . . .
H11 H 0.6295 0.8340 0.3991 0.049 Uiso 1 1 calc R . .
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
O2 S1 O3 118.54(8) . . ?
O2 S1 N2 109.14(7) . . ?
O3 S1 N2 111.98(7) . . ?
O2 S1 O1 103.87(7) . . ?
O3 S1 O1 107.98(7) . . ?
N2 S1 O1 104.02(6) . . ?
C3 N1 C8 120.08(12) . . ?
C3 N1 C2 123.27(12) . . ?
C8 N1 C2 111.59(11) . . ?
C5 O1 S1 113.95(8) . . ?
C3 N2 S1 119.15(10) . . ?
O4 C1 C2 110.15(14) . . ?
O4 C1 H4 109.6 . . ?
C2 C1 H4 109.6 . . ?
O4 C1 H5 109.6 . . ?
C2 C1 H5 109.6 . . ?
H4 C1 H5 108.1 . . ?
C9 O4 C1 110.47(12) . . ?
N1 C2 C1 109.59(13) . . ?
N1 C2 H14 109.8 . . ?
C1 C2 H14 109.8 . . ?
N1 C2 H13 109.8 . . ?
C1 C2 H13 109.8 . . ?
H14 C2 H13 108.2 . . ?
N2 C3 N1 117.97(12) . . ?
N2 C3 C4 122.03(12) . . ?
N1 C3 C4 119.98(12) . . ?
C5 C4 C10 117.33(13) . . ?
C5 C4 C3 118.63(12) . . ?
C10 C4 C3 123.87(12) . . ?
C6 C5 C4 122.57(14) . . ?
C6 C5 O1 118.02(13) . . ?
C4 C5 O1 119.41(12) . . ?
C5 C6 C7 118.72(14) . . ?
C5 C6 H12 120.6 . . ?
C7 C6 H12 120.6 . . ?
C6 C7 C11 120.42(14) . . ?
C6 C7 H2 119.8 . . ?
C11 C7 H2 119.8 . . ?
N1 C8 C9 108.57(13) . . ?
N1 C8 H9 110.0 . . ?
C9 C8 H9 110.0 . . ?
N1 C8 H6 110.0 . . ?
C9 C8 H6 110.0 . . ?
H9 C8 H6 108.4 . . ?
O4 C9 C8 112.05(14) . . ?
O4 C9 H7 109.2 . . ?
C8 C9 H7 109.2 . . ?
O4 C9 H8 109.2 . . ?
C8 C9 H8 109.2 . . ?
H7 C9 H8 107.9 . . ?
C11 C10 C4 120.68(14) . . ?
C11 C10 H10 119.7 . . ?
C4 C10 H10 119.7 . . ?
C10 C11 C7 120.06(15) . . ?
C10 C11 H11 120.0 . . ?
C7 C11 H11 120.0 . . ?
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
S1 O2 1.4191(12) . ?
S1 O3 1.4230(12) . ?
S1 N2 1.6024(12) . ?
S1 O1 1.6163(11) . ?
N1 C3 1.3460(17) . ?
N1 C8 1.4671(18) . ?
N1 C2 1.4708(18) . ?
O1 C5 1.3984(17) . ?
N2 C3 1.3199(18) . ?
C1 O4 1.422(2) . ?
C1 C2 1.506(2) . ?
C1 H4 0.9700 . ?
C1 H5 0.9700 . ?
O4 C9 1.422(2) . ?
C2 H14 0.9700 . ?
C2 H13 0.9700 . ?
C3 C4 1.4747(18) . ?
C4 C5 1.3908(19) . ?
C4 C10 1.3999(19) . ?
C5 C6 1.378(2) . ?
C6 C7 1.379(2) . ?
C6 H12 0.9300 . ?
C7 C11 1.389(2) . ?
C7 H2 0.9300 . ?
C8 C9 1.513(2) . ?
C8 H9 0.9700 . ?
C8 H6 0.9700 . ?
C9 H7 0.9700 . ?
C9 H8 0.9700 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
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
O2 S1 O1 C5 167.05(10) . . . . ?
O3 S1 O1 C5 -66.25(11) . . . . ?
N2 S1 O1 C5 52.87(11) . . . . ?
O2 S1 N2 C3 -144.72(12) . . . . ?
O3 S1 N2 C3 82.01(13) . . . . ?
O1 S1 N2 C3 -34.35(13) . . . . ?
C2 C1 O4 C9 60.3(2) . . . . ?
C3 N1 C2 C1 -148.84(14) . . . . ?
C8 N1 C2 C1 56.42(18) . . . . ?
O4 C1 C2 N1 -58.31(19) . . . . ?
S1 N2 C3 N1 -177.72(10) . . . . ?
S1 N2 C3 C4 0.39(19) . . . . ?
C8 N1 C3 N2 11.2(2) . . . . ?
C2 N1 C3 N2 -141.49(15) . . . . ?
C8 N1 C3 C4 -166.93(13) . . . . ?
C2 N1 C3 C4 40.4(2) . . . . ?
N2 C3 C4 C5 21.3(2) . . . . ?
N1 C3 C4 C5 -160.64(13) . . . . ?
N2 C3 C4 C10 -153.87(14) . . . . ?
N1 C3 C4 C10 24.2(2) . . . . ?
C10 C4 C5 C6 -5.4(2) . . . . ?
C3 C4 C5 C6 179.13(13) . . . . ?
C10 C4 C5 O1 175.20(12) . . . . ?
C3 C4 C5 O1 -0.27(19) . . . . ?
S1 O1 C5 C6 142.37(12) . . . . ?
S1 O1 C5 C4 -38.21(16) . . . . ?
C4 C5 C6 C7 2.5(2) . . . . ?
O1 C5 C6 C7 -178.06(13) . . . . ?
C5 C6 C7 C11 1.5(2) . . . . ?
C3 N1 C8 C9 149.86(14) . . . . ?
C2 N1 C8 C9 -54.49(18) . . . . ?
C1 O4 C9 C8 -60.0(2) . . . . ?
N1 C8 C9 O4 56.19(19) . . . . ?
C5 C4 C10 C11 4.3(2) . . . . ?
C3 C4 C10 C11 179.55(13) . . . . ?
C4 C10 C11 C7 -0.5(2) . . . . ?
C6 C7 C11 C10 -2.5(2) . . . . ?
