Direct <i>N</i>-alkylation of sulfur-containing amines.
Li, Chen; Ge, Min-Tong; Bai, Liang; Xia, Ai-Bao; Xu, Dan-Qian; Xu, Zhen-Yuan; Organic & biomolecular chemistry 19 (2021) 4478–4482; doi:10.1039/d1ob00368b

data_7158042
_publ_section_title
;
 Direct <i>N</i>-alkylation of sulfur-containing amines.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4478
_journal_page_last               4482
_journal_paper_doi               10.1039/d1ob00368b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C37 H32 Cl2 O2 P2 Ru'
_chemical_formula_sum            'C37 H32 Cl2 O2 P2 Ru'
_chemical_formula_weight         742.53
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc26w7kx
_audit_creation_date             2018-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2020-12-22 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.6390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.1640(5)
_cell_length_b                   9.5229(2)
_cell_length_c                   15.7986(3)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      5.372
_cell_volume                     3249.53(12)
_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      172.99
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19347
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.924
_diffrn_reflns_theta_min         6.270
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.370
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1363 before and 0.0631 after correction. The Ratio of minimum to maximum transmission is 0.7084. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       plate
_exptl_crystal_F_000             1512
_refine_diff_density_max         1.285
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.00131(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3046
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0304
_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/[\s^2^(Fo^2^)+(0.0383P)^2^+8.8982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2969
_reflns_number_total             3046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00368b2.cif
_cod_data_source_block           wmj18080_0m
_cod_depositor_comments          'Adding full bibliography for 7158042.cif.'
_cod_database_code               7158042
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Shared sites
{C1', O2}
{C1, O2'}
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O1) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C1') = Uanis(O2)
Uanis(C1) = Uanis(O2')
4. Others
 Fixed Sof: O2(0.375) H2A(0.375) H2B(0.375) C1'(0.125) O1'(0.125) C1(0.375)
 O1(0.375) O2'(0.125) H2'A(0.125) H2'B(0.125)
5.a Riding coordinates:
 O2'(H2'A,H2'B)
5.b Rotating group:
 O2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              26316
_olex2_submission_special_instructions 'No special instructions were received'