#------------------------------------------------------------------------------
#$Date: 2023-09-05 21:57:17 +0200 (Tue 05 de Sep de 2023) $
#$Revision: 286141 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/70/7247075.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_7247075
loop_
_publ_author_name
'Pal, Nilay Kumar'
'Singh, Kuldeep'
'Patra, Moumita'
'Yadav, Suman'
'Pandey, Prabhakar K.'
'Bera, Jitendra K.'
_publ_section_title
;
 Ni(ii)-catalyzed oxidative deamination of benzyl amines with water
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              6212
_journal_page_last               6217
_journal_paper_doi               10.1039/D3GC00672G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C16 H16 N3 Ni0.5 O3 S, C H4 O'
_chemical_formula_sum            'C18 H20 N3 Ni O4 S'
_chemical_formula_weight         433.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-24 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.6180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6620(4)
_cell_length_b                   22.8698(9)
_cell_length_c                   14.5817(5)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.43
_cell_volume                     3538.5(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26661
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         2.641
_exptl_absorpt_coefficient_mu    1.246
_exptl_absorpt_correction_T_max  0.9460
_exptl_absorpt_correction_T_min  0.8753
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1778 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.9253.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       block
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.999
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0318
_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)+(0.0411P)²+6.8573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3915
_reflns_number_total             4399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc00672g2.cif
_cod_data_source_block           Nickel_1
_cod_depositor_comments
'Adding full bibliography for 7247074--7247077.cif.'
_cod_database_code               7247075
_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   0.961
_shelx_estimated_absorpt_t_min   0.369
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B), C14(H14A,H14B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C4(H4), C10(H10), C11(H11), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Ni1 Ni 0.500000 0.14556(2) 0.250000 0.01088(8) Uani 1 2 d S T P . .
S1 S 0.31013(4) 0.35751(2) 0.52275(3) 0.01311(10) Uani 1 1 d . . . . .
O2 O 0.33934(12) 0.30456(5) 0.57635(8) 0.0196(3) Uani 1 1 d . . . . .
O3 O 0.41767(12) 0.39674(6) 0.52141(9) 0.0198(3) Uani 1 1 d . . . . .
O1 O 0.19766(12) 0.38720(6) 0.55036(9) 0.0194(3) Uani 1 1 d . . . . .
O1S O 0.22824(14) 0.49647(6) 0.63821(11) 0.0295(3) Uani 1 1 d . . . . .
H1S H 0.231265 0.466053 0.608744 0.044 Uiso 1 1 calc GR . . . .
N2 N 0.72330(12) 0.20258(6) 0.31401(9) 0.0117(3) Uani 1 1 d . . . . .
N1 N 0.56575(12) 0.25064(6) 0.36134(9) 0.0117(3) Uani 1 1 d . . . . .
N3 N 0.61152(13) 0.08838(6) 0.31313(9) 0.0136(3) Uani 1 1 d . . . . .
C2 C 0.67486(14) 0.28145(7) 0.39265(10) 0.0121(3) Uani 1 1 d . . . . .
C16 C 0.26872(15) 0.33580(7) 0.40552(11) 0.0142(3) Uani 1 1 d . . . . .
H16A H 0.211617 0.302744 0.404772 0.017 Uiso 1 1 calc R . . . .
H16B H 0.224094 0.367707 0.372902 0.017 Uiso 1 1 calc R . . . .
C6 C 0.89980(15) 0.27047(7) 0.37906(11) 0.0156(3) Uani 1 1 d . . . . .
H6 H 0.967260 0.249998 0.358852 0.019 Uiso 1 1 calc R . . . .
C3 C 0.69187(15) 0.33286(7) 0.44342(11) 0.0145(3) Uani 1 1 d . . . . .
H3 H 0.624685 0.352667 0.465298 0.017 Uiso 1 1 calc R . . . .
C15 C 0.38167(15) 0.31896(7) 0.35426(11) 0.0145(3) Uani 1 1 d . . . . .
H15A H 0.354494 0.313961 0.289291 0.017 Uiso 1 1 calc R . . . .
H15B H 0.443596 0.350146 0.360224 0.017 Uiso 1 1 calc R . . . .
C14 C 0.44170(14) 0.26242(7) 0.39265(11) 0.0129(3) Uani 1 1 d . . . . .
H14A H 0.450185 0.264425 0.459414 0.016 Uiso 1 1 calc R . . . .
H14B H 0.385904 0.230055 0.374520 0.016 Uiso 1 1 calc R . . . .
C5 C 0.91660(16) 0.32226(8) 0.42833(12) 0.0179(3) Uani 1 1 d . . . . .
H5 H 0.997628 0.337123 0.441031 0.021 Uiso 1 1 calc R . . . .
C7 C 0.77592(15) 0.25091(7) 0.36163(10) 0.0123(3) Uani 1 1 d . . . . .
C4 C 0.81502(16) 0.35283(7) 0.45950(12) 0.0166(3) Uani 1 1 d . . . . .
H4 H 0.830581 0.387518 0.491913 0.020 Uiso 1 1 calc R . . . .
C1 C 0.59648(15) 0.20320(7) 0.31321(11) 0.0124(3) Uani 1 1 d . . . . .
C10 C 0.81839(16) 0.05682(7) 0.37022(11) 0.0162(3) Uani 1 1 d . . . . .
H10 H 0.904992 0.063068 0.375942 0.019 Uiso 1 1 calc R . . . .
C11 C 0.76841(17) 0.00754(8) 0.40889(12) 0.0194(3) Uani 1 1 d . . . . .
H11 H 0.821113 -0.019809 0.440169 0.023 Uiso 1 1 calc R . . . .
C9 C 0.73795(15) 0.09652(7) 0.32310(11) 0.0135(3) Uani 1 1 d . . . . .
C13 C 0.56354(16) 0.04068(7) 0.35207(12) 0.0167(3) Uani 1 1 d . . . . .
H13 H 0.476680 0.035262 0.346250 0.020 Uiso 1 1 calc R . . . .
C8 C 0.78885(15) 0.15118(7) 0.28221(11) 0.0143(3) Uani 1 1 d . . . . .
H8A H 0.878471 0.154465 0.300667 0.017 Uiso 1 1 calc R . . . .
H8B H 0.776806 0.149040 0.215490 0.017 Uiso 1 1 calc R . . . .
C12 C 0.63926(18) -0.00023(8) 0.40019(12) 0.0197(3) Uani 1 1 d . . . . .
H12 H 0.603773 -0.032591 0.426380 0.024 Uiso 1 1 calc R . . . .
C1S C 0.3509(2) 0.51886(9) 0.65816(15) 0.0295(4) Uani 1 1 d . . . . .
H1SA H 0.384546 0.529597 0.601810 0.044 Uiso 1 1 calc GR . . . .
H1SB H 0.403666 0.489574 0.689345 0.044 Uiso 1 1 calc GR . . . .
H1SC H 0.348184 0.552677 0.696920 0.044 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 0.0033 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'
Ni Ni 0.3393 1.1124 '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
N3 Ni1 N3 95.14(8) . 2_655 ?
C1 Ni1 N3 175.76(6) . 2_655 ?
C1 Ni1 N3 87.65(6) . . ?
C1 Ni1 N3 175.76(6) 2_655 . ?
C1 Ni1 N3 87.65(6) 2_655 2_655 ?
C1 Ni1 C1 89.74(10) . 2_655 ?
O2 S1 O1 111.99(8) . . ?
O2 S1 C16 107.50(8) . . ?
O3 S1 O2 113.03(8) . . ?
O3 S1 O1 112.57(8) . . ?
O3 S1 C16 106.16(8) . . ?
O1 S1 C16 104.95(7) . . ?
C1S O1S H1S 109.5 . . ?
C7 N2 C8 127.77(13) . . ?
C1 N2 C7 110.47(13) . . ?
C1 N2 C8 120.89(13) . . ?
C2 N1 C14 123.58(13) . . ?
C1 N1 C2 109.78(13) . . ?
C1 N1 C14 125.59(13) . . ?
C9 N3 Ni1 121.07(11) . . ?
C13 N3 Ni1 120.24(11) . . ?
C13 N3 C9 118.61(14) . . ?
C3 C2 N1 131.33(15) . . ?
C3 C2 C7 122.03(14) . . ?
C7 C2 N1 106.63(13) . . ?
S1 C16 H16A 108.8 . . ?
S1 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C15 C16 S1 113.82(11) . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C5 C6 H6 121.9 . . ?
C5 C6 C7 116.12(15) . . ?
C7 C6 H6 121.9 . . ?
C2 C3 H3 122.0 . . ?
C4 C3 C2 116.08(15) . . ?
C4 C3 H3 122.0 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C14 C15 C16 110.91(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
N1 C14 C15 113.62(13) . . ?
N1 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C6 C5 H5 119.0 . . ?
C6 C5 C4 121.93(15) . . ?
C4 C5 H5 119.0 . . ?
N2 C7 C2 105.80(13) . . ?
N2 C7 C6 132.33(15) . . ?
C6 C7 C2 121.87(15) . . ?
C3 C4 C5 121.95(15) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
N2 C1 Ni1 120.08(12) . . ?
N1 C1 Ni1 132.59(12) . . ?
N1 C1 N2 107.31(13) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.33(16) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.04(16) . . ?
C12 C11 H11 120.5 . . ?
N3 C9 C10 121.65(15) . . ?
N3 C9 C8 117.66(14) . . ?
C10 C9 C8 120.68(15) . . ?
N3 C13 H13 118.9 . . ?
N3 C13 C12 122.21(16) . . ?
C12 C13 H13 118.9 . . ?
N2 C8 C9 109.78(13) . . ?
N2 C8 H8A 109.7 . . ?
N2 C8 H8B 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.14(16) . . ?
C13 C12 H12 120.4 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 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
Ni1 N3 1.9382(14) . ?
Ni1 N3 1.9382(14) 2_655 ?
Ni1 C1 1.8600(16) . ?
Ni1 C1 1.8600(16) 2_655 ?
S1 O2 1.4583(12) . ?
S1 O3 1.4576(13) . ?
S1 O1 1.4682(12) . ?
S1 C16 1.7933(16) . ?
O1S H1S 0.8200 . ?
O1S C1S 1.408(2) . ?
N2 C7 1.394(2) . ?
N2 C1 1.351(2) . ?
N2 C8 1.466(2) . ?
N1 C2 1.3978(19) . ?
N1 C14 1.466(2) . ?
N1 C1 1.350(2) . ?
N3 C9 1.354(2) . ?
N3 C13 1.353(2) . ?
C2 C3 1.392(2) . ?
C2 C7 1.396(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.528(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(2) . ?
C6 C7 1.394(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.525(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.402(2) . ?
C4 H4 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.389(2) . ?
C10 C9 1.385(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C9 C8 1.508(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.382(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12 0.9300 . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.399 0.250 42.5 16.1 ?
2 0.000 0.601 0.750 42.5 15.6 ?
3 0.500 0.101 0.750 42.5 15.6 ?
4 0.500 0.899 0.250 42.5 16.1 ?
