#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:28:23 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266166 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158042.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_7158042
loop_
_publ_author_name
'Li, Chen'
'Ge, Min-Tong'
'Bai, Liang'
'Xia, Ai-Bao'
'Xu, Dan-Qian'
'Xu, Zhen-Yuan'
_publ_section_title
;
 Direct N-alkylation of sulfur-containing amines.
;
_journal_issue                   20
_journal_name_full               'Organic & 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       'φ and ω 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 λ/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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0383P)²+8.8982P] where P=(Fo²+2Fc²)/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 > 2σ(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
_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.
;
_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)
;
_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
Ru1 Ru 0.500000 0.32578(2) 0.750000 0.01617(13) Uani 1 2 d S T P . .
Cl1 Cl 0.55570(3) 0.35206(7) 0.91800(5) 0.03302(18) Uani 1 1 d . . . . .
P1 P 0.59318(3) 0.33151(6) 0.73042(4) 0.01615(15) Uani 1 1 d . . . . .
O2 O 0.500000 0.5502(4) 0.750000 0.0357(7) Uani 0.75 2 d S T P A 1
H2A H 0.519333 0.608450 0.799705 0.054 Uiso 0.375 1 d GR . . A 1
H2B H 0.480656 0.608450 0.700285 0.054 Uiso 0.375 1 d GR . . A 1
C1' C 0.500000 0.5502(4) 0.750000 0.0357(7) Uani 0.25 2 d S T P A 2
O1' O 0.500000 0.645(2) 0.750000 0.048(3) Uani 0.25 2 d S T P A 2
C1 C 0.500000 0.1095(5) 0.750000 0.0215(6) Uani 0.75 2 d S TU P A 1
O1 O 0.500000 0.0212(4) 0.750000 0.0233(7) Uani 0.75 2 d S TU P A 1
O2' O 0.500000 0.1095(5) 0.750000 0.0215(6) Uani 0.25 2 d S T P A 2
H2'A H 0.488060 0.071523 0.701130 0.032 Uiso 0.125 1 d R . . A 2
H2'B H 0.512020 0.071533 0.798880 0.032 Uiso 0.125 1 d R . . A 2
C2 C 0.61973(11) 0.5127(2) 0.73783(17) 0.0198(5) Uani 1 1 d . . . . .
C3 C 0.58325(12) 0.6084(3) 0.6674(2) 0.0276(5) Uani 1 1 d . . . . .
H3 H 0.547958 0.576033 0.613038 0.033 Uiso 1 1 calc R . . . .
C4 C 0.59836(14) 0.7497(3) 0.6765(2) 0.0368(6) Uani 1 1 d . . . . .
H4 H 0.573514 0.813772 0.628362 0.044 Uiso 1 1 calc R . . . .
C5 C 0.64950(16) 0.7979(3) 0.7556(2) 0.0401(7) Uani 1 1 d . . . . .
H5 H 0.659163 0.895237 0.762352 0.048 Uiso 1 1 calc R . . . .
C6 C 0.68640(15) 0.7047(3) 0.8245(2) 0.0383(7) Uani 1 1 d . . . . .
H6 H 0.722010 0.737720 0.878053 0.046 Uiso 1 1 calc R . . . .
C7 C 0.67174(12) 0.5620(3) 0.81600(18) 0.0274(5) Uani 1 1 d . . . . .
H7 H 0.697395 0.498325 0.863794 0.033 Uiso 1 1 calc R . . . .
C8 C 0.66029(10) 0.2327(2) 0.81390(16) 0.0198(5) Uani 1 1 d . . . . .
C9 C 0.71491(12) 0.2334(3) 0.80402(19) 0.0318(6) Uani 1 1 d . . . . .
H9 H 0.717132 0.287037 0.754945 0.038 Uiso 1 1 calc R . . . .
C10 C 0.76575(14) 0.1566(3) 0.8650(2) 0.0388(7) Uani 1 1 d . . . . .
H10 H 0.802899 0.158791 0.858295 0.047 Uiso 1 1 calc R . . . .
C11 C 0.76256(12) 0.0766(3) 0.93587(19) 0.0318(6) Uani 1 1 d . . . . .
H11 H 0.797510 0.023895 0.977805 0.038 Uiso 1 1 calc R . . . .
C12 C 0.70878(12) 0.0735(3) 0.94552(18) 0.0268(5) Uani 1 1 d . . . . .
H12 H 0.706590 0.017570 0.993730 0.032 Uiso 1 1 calc R . . . .
C13 C 0.65758(11) 0.1515(2) 0.88520(17) 0.0217(5) Uani 1 1 d . . . . .
H13 H 0.620706 0.149372 0.892663 0.026 Uiso 1 1 calc R . . . .
C14 C 0.58885(10) 0.2664(2) 0.61856(16) 0.0191(5) Uani 1 1 d . . . . .
C15 C 0.60572(14) 0.3457(3) 0.56032(19) 0.0295(6) Uani 1 1 d . . . . .
H15 H 0.617985 0.440741 0.575968 0.035 Uiso 1 1 calc R . . . .
C16 C 0.60480(15) 0.2870(3) 0.4791(2) 0.0346(6) Uani 1 1 d . . . . .
H16 H 0.616039 0.342907 0.439435 0.042 Uiso 1 1 calc R . . . .
C17 C 0.58793(13) 0.1499(3) 0.45554(19) 0.0294(6) Uani 1 1 d . . . . .
H17 H 0.587667 0.110498 0.400115 0.035 Uiso 1 1 calc R . . . .
C18 C 0.57134(16) 0.0697(3) 0.5131(2) 0.0400(7) Uani 1 1 d . . . . .
H18 H 0.560047 -0.025847 0.497747 0.048 Uiso 1 1 calc R . . . .
C19 C 0.57107(15) 0.1280(3) 0.5933(2) 0.0354(6) Uani 1 1 d . . . . .
H19 H 0.558531 0.072327 0.631633 0.043 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 0.0148 0.0070 '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'
Cl Cl 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2596 0.3354 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -0.0765 2.5657 '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
Cl1 Ru1 Cl1 167.99(4) 2_656 . ?
Cl1 Ru1 P1 87.05(2) . 2_656 ?
Cl1 Ru1 P1 92.68(2) 2_656 2_656 ?
Cl1 Ru1 P1 92.68(2) . . ?
Cl1 Ru1 P1 87.05(2) 2_656 . ?
P1 Ru1 P1 177.40(3) 2_656 . ?
O2 Ru1 Cl1 83.993(18) . . ?
O2 Ru1 Cl1 83.994(18) . 2_656 ?
O2 Ru1 P1 88.702(13) . . ?
O2 Ru1 P1 88.702(13) . 2_656 ?
C1' Ru1 Cl1 83.993(18) . . ?
C1' Ru1 P1 88.702(13) . . ?
C1 Ru1 Cl1 96.007(18) . . ?
C1 Ru1 Cl1 96.006(18) . 2_656 ?
C1 Ru1 P1 91.298(13) . . ?
C1 Ru1 P1 91.298(14) . 2_656 ?
C1 Ru1 O2 180.0 . . ?
O2' Ru1 Cl1 96.007(18) . . ?
O2' Ru1 P1 91.298(13) . . ?
O2' Ru1 C1' 180.0 . . ?
C2 P1 Ru1 109.58(7) . . ?
C2 P1 C14 104.36(10) . . ?
C8 P1 Ru1 118.33(8) . . ?
C8 P1 C2 105.53(11) . . ?
C8 P1 C14 99.82(10) . . ?
C14 P1 Ru1 117.68(8) . . ?
Ru1 O2 H2A 127.9 . . ?
Ru1 O2 H2B 127.9 . . ?
H2A O2 H2B 104.1 . . ?
Ru1 C1' H2A 127.937(2) . 2_656 ?
Ru1 C1' H2B 127.928(5) . 2_656 ?
H2A C1' H2B 104.1 2_656 2_656 ?
O1' C1' Ru1 180.0 . . ?
H2A O1' H2B 127.6 2_656 2_656 ?
Ru1 C1 H2'A 117.6(3) . 2_656 ?
Ru1 C1 H2'B 117.6(3) . 2_656 ?
O1 C1 Ru1 180.0 . . ?
O1 C1 H2'A 62.4(3) . 2_656 ?
O1 C1 H2'B 62.4(3) . 2_656 ?
H2'A C1 H2'B 124.9 2_656 2_656 ?
C1 O1 H2'A 55.3(2) . 2_656 ?
C1 O1 H2'B 55.3(2) . 2_656 ?
H2'A O1 H2'B 110.7 2_656 2_656 ?
Ru1 O2' H2'A 117.6 . . ?
Ru1 O2' H2'B 117.6 . . ?
H2'A O2' H2'B 124.9 . . ?
C3 C2 P1 119.02(19) . . ?
C7 C2 P1 121.83(19) . . ?
C7 C2 C3 118.8(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.2(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 P1 119.65(18) . . ?
C13 C8 P1 121.45(18) . . ?
C13 C8 C9 118.8(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C15 C14 P1 123.39(18) . . ?
C15 C14 C19 118.2(2) . . ?
C19 C14 P1 118.33(18) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.2(2) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H19 119.5 . . ?
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
Ru1 Cl1 2.3907(7) 2_656 ?
Ru1 Cl1 2.3907(7) . ?
Ru1 P1 2.4067(6) . ?
Ru1 P1 2.4066(6) 2_656 ?
Ru1 O2 2.137(3) . ?
Ru1 C1' 2.137(3) . ?
Ru1 C1 2.060(4) . ?
Ru1 O2' 2.060(4) . ?
P1 C2 1.827(2) . ?
P1 C8 1.826(2) . ?
P1 C14 1.831(2) . ?
O2 H2A 0.9018 . ?
O2 H2B 0.9020 . ?
C1' O1' 0.905(17) . ?
C1 O1 0.841(4) . ?
C1 H2'A 0.781(2) 2_656 ?
C1 H2'B 0.781(2) 2_656 ?
O1 H2'A 0.842(2) 2_656 ?
O1 H2'B 0.842(2) 2_656 ?
O2' H2'A 0.7813 . ?
O2' H2'B 0.7812 . ?
C2 C3 1.402(3) . ?
C2 C7 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(3) . ?
C8 C13 1.392(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.375(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 C19 1.389(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.369(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(4) . ?
C19 H19 0.9500 . ?
