#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:52:19 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270375 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128993.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_7128993
loop_
_publ_author_name
'Singh, Hardeep'
'MacKay, Alyson'
'Sheibany, Nooshin'
'Chen, Fei'
'Mosser, Maëlle'
'Rouet, Pierre-Étienne'
'Rousseau, Frédéric'
'Askari, Mohammad S.'
'Ottenwaelder, Xavier'
_publ_section_title
;
 Intramolecular H-bond stabilization of a primary hydroxylamine in
 salen-type metal complexes.
;
_journal_issue                   80
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10403
_journal_page_last               10406
_journal_paper_doi               10.1039/d1cc03077a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C23 H31 Cu N3 O4 S'
_chemical_formula_sum            'C23 H31 Cu N3 O4 S'
_chemical_formula_weight         509.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1906(3)
_cell_length_b                   12.7306(2)
_cell_length_c                   10.9264(2)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      67.31
_cell_measurement_theta_min      2.47
_cell_volume                     2487.62(7)
_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-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22219
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.494
_diffrn_reflns_theta_min         2.471
_exptl_absorpt_coefficient_mu    2.293
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0435
_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)+(0.0766P)²+0.8887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3562
_reflns_number_total             4524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03077a2.cif
_cod_data_source_block           cu_Fei18_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7128990--7128999.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128993
_shelx_shelxl_version_number     2017/1
_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_min   0.672
_shelx_estimated_absorpt_t_max   0.798
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'
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
Cu1 Cu 0.88680(2) 0.58579(3) 0.44754(4) 0.02427(16) Uani 1 1 d . . . . .
S1 S 1.00011(4) 0.52519(5) 0.28052(7) 0.0252(2) Uani 1 1 d . . . . .
O1 O 0.83713(14) 0.37155(18) 0.4691(2) 0.0490(6) Uani 1 1 d . . . . .
H1A H 0.809286 0.414124 0.497659 0.074 Uiso 1 1 calc R U . . .
O2 O 0.79602(11) 0.56299(15) 0.50887(19) 0.0279(5) Uani 1 1 d . . . . .
O3 O 1.03863(11) 0.56515(16) 0.18652(19) 0.0309(5) Uani 1 1 d . . . . .
O4 O 1.03868(11) 0.44545(16) 0.36449(19) 0.0304(5) Uani 1 1 d . . . . .
N1 N 0.88771(14) 0.42774(17) 0.4089(2) 0.0274(6) Uani 1 1 d . . . . .
H1 H 0.939191 0.400675 0.441380 0.033 Uiso 1 1 calc R U . . .
N2 N 0.97316(13) 0.61511(17) 0.3625(2) 0.0251(5) Uani 1 1 d . . . . .
N3 N 0.87523(13) 0.73601(18) 0.4446(2) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.87191(17) 0.4107(2) 0.2762(3) 0.0274(7) Uani 1 1 d . . . . .
C2 C 0.80987(18) 0.3559(2) 0.2176(3) 0.0388(8) Uani 1 1 d . . . . .
H2 H 0.775885 0.326823 0.264888 0.047 Uiso 1 1 calc R U . . .
C3 C 0.79743(19) 0.3435(3) 0.0889(3) 0.0439(9) Uani 1 1 d . . . . .
H3 H 0.755113 0.304918 0.048772 0.053 Uiso 1 1 calc R U . . .
C4 C 0.84551(18) 0.3863(3) 0.0193(3) 0.0369(8) Uani 1 1 d . . . . .
H4 H 0.836963 0.375951 -0.068270 0.044 Uiso 1 1 calc R U . . .
C5 C 0.90609(17) 0.4441(2) 0.0763(3) 0.0296(7) Uani 1 1 d . . . . .
H5 H 0.938669 0.475156 0.027880 0.036 Uiso 1 1 calc R U . . .
C6 C 0.91955(16) 0.4570(2) 0.2045(3) 0.0254(6) Uani 1 1 d . . . . .
C7 C 0.96084(17) 0.7199(2) 0.3013(3) 0.0300(7) Uani 1 1 d . . . . .
H7A H 0.922287 0.715467 0.224788 0.036 Uiso 1 1 calc R U . . .
H7AB H 1.007776 0.746696 0.279097 0.036 Uiso 1 1 calc R U . . .
C8 C 0.93511(17) 0.7906(2) 0.3960(3) 0.0316(7) Uani 1 1 d . . . . .
H8A H 0.977305 0.806081 0.464663 0.038 Uiso 1 1 calc R U . . .
H8AB H 0.916215 0.857723 0.356670 0.038 Uiso 1 1 calc R U . . .
C9 C 0.82104(16) 0.7865(2) 0.4771(3) 0.0281(7) Uani 1 1 d . . . . .
H9 H 0.820679 0.860515 0.465748 0.034 Uiso 1 1 calc R U . . .
C10 C 0.76069(16) 0.7427(2) 0.5289(3) 0.0287(7) Uani 1 1 d . . . . .
C11 C 0.75091(15) 0.6336(2) 0.5446(3) 0.0269(6) Uani 1 1 d . . . . .
C12 C 0.68866(17) 0.6000(2) 0.5986(3) 0.0324(7) Uani 1 1 d . . . . .
C13 C 0.64163(17) 0.6771(3) 0.6310(3) 0.0368(8) Uani 1 1 d . . . . .
H13 H 0.600277 0.654596 0.666339 0.044 Uiso 1 1 calc R U . . .
C14 C 0.65045(17) 0.7853(3) 0.6157(3) 0.0335(7) Uani 1 1 d . . . . .
C15 C 0.71032(17) 0.8161(2) 0.5652(3) 0.0333(7) Uani 1 1 d . . . . .
H15 H 0.718408 0.888930 0.554102 0.040 Uiso 1 1 calc R U . . .
C16 C 0.67436(18) 0.4837(3) 0.6216(3) 0.0401(8) Uani 1 1 d . . . . .
C17 C 0.7419(2) 0.4386(3) 0.7116(3) 0.0434(9) Uani 1 1 d . . . . .
H17A H 0.746184 0.473237 0.792743 0.065 Uiso 1 1 calc R U . . .
H17B H 0.787540 0.450932 0.678077 0.065 Uiso 1 1 calc R U . . .
H17C H 0.734917 0.362964 0.721457 0.065 Uiso 1 1 calc R U . . .
C18 C 0.6588(2) 0.4227(3) 0.4977(4) 0.0486(10) Uani 1 1 d . . . . .
H18A H 0.655247 0.347494 0.514831 0.073 Uiso 1 1 calc R U . . .
H18B H 0.699699 0.434780 0.452107 0.073 Uiso 1 1 calc R U . . .
H18C H 0.611681 0.447024 0.447534 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6059(2) 0.4669(3) 0.6842(5) 0.0667(13) Uani 1 1 d . . . . .
H19A H 0.599311 0.391619 0.697573 0.100 Uiso 1 1 calc R U . . .
H19B H 0.561149 0.494863 0.630451 0.100 Uiso 1 1 calc R U . . .
H19C H 0.613811 0.503472 0.764477 0.100 Uiso 1 1 calc R U . . .
C20 C 0.59317(19) 0.8614(3) 0.6538(3) 0.0413(8) Uani 1 1 d . . . . .
C21 C 0.6202(2) 0.9758(3) 0.6518(4) 0.0578(11) Uani 1 1 d . . . . .
H21A H 0.583897 1.022421 0.680417 0.087 Uiso 1 1 calc R U . . .
H21B H 0.624944 0.995030 0.566742 0.087 Uiso 1 1 calc R U . . .
H21C H 0.668849 0.982921 0.706953 0.087 Uiso 1 1 calc R U . . .
C22 C 0.5815(2) 0.8362(3) 0.7863(3) 0.0483(9) Uani 1 1 d . . . . .
H22A H 0.629400 0.840824 0.844019 0.072 Uiso 1 1 calc R U . . .
H22B H 0.561285 0.764957 0.788506 0.072 Uiso 1 1 calc R U . . .
H22C H 0.546207 0.886662 0.811026 0.072 Uiso 1 1 calc R U . . .
C23 C 0.5190(2) 0.8500(3) 0.5628(4) 0.0568(11) Uani 1 1 d . . . . .
H23A H 0.501567 0.777160 0.563279 0.085 Uiso 1 1 calc R U . . .
H23B H 0.526119 0.868671 0.478728 0.085 Uiso 1 1 calc R U . . .
H23C H 0.481669 0.896840 0.588001 0.085 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 0.0181 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'
Cu Cu -1.9646 0.5888 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 Cu1 N3 93.31(9) . . ?
O2 Cu1 N2 172.50(9) . . ?
N3 Cu1 N2 84.25(9) . . ?
O2 Cu1 N1 87.90(9) . . ?
N3 Cu1 N1 166.97(10) . . ?
N2 Cu1 N1 92.90(9) . . ?
O2 Cu1 O4 93.84(8) . 3_766 ?
N3 Cu1 O4 103.51(9) . 3_766 ?
N2 Cu1 O4 93.62(9) . 3_766 ?
N1 Cu1 O4 89.34(9) . 3_766 ?
O3 S1 O4 117.01(12) . . ?
O3 S1 N2 112.92(12) . . ?
O4 S1 N2 108.07(12) . . ?
O3 S1 C6 107.90(13) . . ?
O4 S1 C6 102.42(13) . . ?
N2 S1 C6 107.68(13) . . ?
N1 O1 H1A 109.5 . . ?
C11 O2 Cu1 128.43(18) . . ?
S1 O4 Cu1 145.72(13) . 3_766 ?
O1 N1 C1 111.3(2) . . ?
O1 N1 Cu1 111.59(17) . . ?
C1 N1 Cu1 110.26(17) . . ?
O1 N1 H1 107.8 . . ?
C1 N1 H1 107.8 . . ?
Cu1 N1 H1 107.8 . . ?
C7 N2 S1 115.47(19) . . ?
C7 N2 Cu1 107.98(17) . . ?
S1 N2 Cu1 118.54(13) . . ?
C9 N3 C8 121.4(2) . . ?
C9 N3 Cu1 125.6(2) . . ?
C8 N3 Cu1 112.92(17) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 N1 122.5(3) . . ?
C6 C1 N1 118.0(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 S1 120.6(2) . . ?
C1 C6 S1 119.1(2) . . ?
N2 C7 C8 105.5(2) . . ?
N2 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
N2 C7 H7AB 110.7 . . ?
C8 C7 H7AB 110.7 . . ?
H7A C7 H7AB 108.8 . . ?
N3 C8 C7 108.0(2) . . ?
N3 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
N3 C8 H8AB 110.1 . . ?
C7 C8 H8AB 110.1 . . ?
H8A C8 H8AB 108.4 . . ?
N3 C9 C10 126.6(3) . . ?
N3 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
C11 C10 C15 120.8(3) . . ?
C11 C10 C9 123.4(3) . . ?
C15 C10 C9 115.7(3) . . ?
O2 C11 C10 122.2(3) . . ?
O2 C11 C12 119.9(3) . . ?
C10 C11 C12 117.9(3) . . ?
C13 C12 C11 117.6(3) . . ?
C13 C12 C16 120.6(3) . . ?
C11 C12 C16 121.7(3) . . ?
C12 C13 C14 125.1(3) . . ?
C12 C13 H13 117.5 . . ?
C14 C13 H13 117.5 . . ?
C15 C14 C13 116.6(3) . . ?
C15 C14 C20 124.0(3) . . ?
C13 C14 C20 119.3(3) . . ?
C14 C15 C10 121.9(3) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
C12 C16 C17 109.0(3) . . ?
C12 C16 C18 110.7(3) . . ?
C17 C16 C18 111.7(3) . . ?
C12 C16 C19 112.5(3) . . ?
C17 C16 C19 106.2(3) . . ?
C18 C16 C19 106.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C20 C14 109.0(3) . . ?
C23 C20 C22 109.6(3) . . ?
C14 C20 C22 110.0(3) . . ?
C23 C20 C21 109.1(3) . . ?
C14 C20 C21 111.1(3) . . ?
C22 C20 C21 108.1(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Cu1 O2 1.915(2) . ?
Cu1 N3 1.924(2) . ?
Cu1 N2 2.001(2) . ?
Cu1 N1 2.057(2) . ?
Cu1 O4 2.279(2) 3_766 ?
S1 O3 1.438(2) . ?
S1 O4 1.459(2) . ?
S1 N2 1.585(2) . ?
S1 C6 1.774(3) . ?
O1 N1 1.418(3) . ?
O1 H1A 0.8400 . ?
O2 C11 1.323(3) . ?
N1 C1 1.442(4) . ?
N1 H1 1.0000 . ?
N2 C7 1.490(4) . ?
N3 C9 1.280(4) . ?
N3 C8 1.470(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.392(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.509(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.437(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(4) . ?
C10 C15 1.415(4) . ?
C11 C12 1.435(4) . ?
C12 C13 1.390(4) . ?
C12 C16 1.531(4) . ?
C13 C14 1.401(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.365(4) . ?
C14 C20 1.535(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.538(5) . ?
C16 C18 1.541(5) . ?
C16 C19 1.542(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C23 1.530(5) . ?
C20 C22 1.536(5) . ?
C20 C21 1.539(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
_geom_hbond_publ_flag
N1 H1 N2 1.00 2.43 3.261(4) 139.5 3_766 yes
N1 H1 O4 1.00 2.21 2.884(3) 123.8 . yes
O1 H1A O2 0.84 1.92 2.609(3) 138.9 . yes
